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11 pages, 1527 KiB

Open AccessArticle

Cytotoxic and Antibacterial Activity of Koninginins Isolated from the Mangrove-Derived Endophytic Fungus Trichoderma sp.

by Gisele da Costa Ramos, Ingryd Nayara de Farias Ramos, Luciano Almeida Watanabe, Luciana Almeida Watanabe Castro, Alessandra Jackeline Guedes de Moraes, Gleiciane Rodrigues dos Santos, José Edson de Sousa Siqueira, André Salim Khayat, Andrey Moacir do Rosario Marinho and Patrícia Santana Barbosa Marinho

Molecules 2024, 29(22), 5278; https://doi.org/10.3390/molecules29225278 - 8 Nov 2024

Viewed by 537

Abstract

The search for bioactive compounds for the treatment of several diseases has led to the study of endophytic fungi. Neoplastic diseases are among the most significant health concerns due to their high mortality rate, and there is a dearth of efficacious pharmaceutical agents [...] Read more.

The search for bioactive compounds for the treatment of several diseases has led to the study of endophytic fungi. Neoplastic diseases are among the most significant health concerns due to their high mortality rate, and there is a dearth of efficacious pharmaceutical agents for the treatment of cancer. Gastric cancer is one of the most aggressive forms of cancer and is among those with the highest mortality rates in Brazil. Accordingly, the objective of this study was to identify compounds with cytotoxic activity from the mangrove-derived endophytic fungus Trichoderma sp. Isolation of the chemical compounds was conducted using chromatographic methods, while structural elucidation was achieved through the application of spectroscopic (NMR and UV) and spectrometric (MS) techniques. The fungus Trichoderma sp. was found to produce five distinct koninginins (A, B, C, E, and J). The organic phases of the extracts and isolated compounds were evaluated for their antimicrobial and cytotoxic potentials, respectively, through microdilution testing and the MTT method. In the cytotoxicity assay, both the AF extract and koninginin A demonstrated favorable outcomes, indicating their potential as promising anticancer therapeutic agents. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 919 KiB

Open AccessArticle

Essential Oil-Based Soap with Clove and Oregano: A Promising Antifungal and Antibacterial Alternative against Multidrug-Resistant Microorganisms

by Ana Paula Merino Cruz, Felipe Garcia Nishimura, Vinícius Cristian Oti dos Santos, Eliana Guedes Steling, Marcia Regina Von Zeska Kress, Mozart Marins and Ana Lucia Fachin

Molecules 2024, 29(19), 4682; https://doi.org/10.3390/molecules29194682 - 2 Oct 2024

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Abstract

The transmission of microorganisms via hands is a critical factor in healthcare-associated infections (HAIs), underscoring the importance of rigorous hand hygiene. The rise of antimicrobial-resistant microorganisms, driven in part by the overuse of antibiotics in clinical medicine, presents a significant global health challenge. [...] Read more.

The transmission of microorganisms via hands is a critical factor in healthcare-associated infections (HAIs), underscoring the importance of rigorous hand hygiene. The rise of antimicrobial-resistant microorganisms, driven in part by the overuse of antibiotics in clinical medicine, presents a significant global health challenge. Antimicrobial soaps, although commonly used, may exacerbate bacterial resistance and disrupt skin microbiota, posing additional health risks and environmental hazards. Essential oils, with their broad-spectrum antimicrobial properties, offer a promising alternative. This study evaluates the antimicrobial activity of essential oils against various bacterial and fungal strains, including multidrug-resistant isolates. Using a range of in vitro and in vivo antimicrobial assays, including minimal inhibitory concentration (MIC), minimal bactericidal concentration (MBC), and minimal fungicidal concentration (MFC), the essential oils were tested against a broad spectrum of pathogens. Additionally, the chemical composition of the oils was analyzed in detail using gas chromatography–mass spectrometry (CG–MS). Clove, oregano, and thyme oils demonstrated potent inhibition of all tested ATCC bacterial strains, with MIC values ranging from 3.125 to 50 μL/mL. These oils also showed significant activity against multidrug-resistant Escherichia coli and Pseudomonas aeruginosa strains. Notably, clove oil exhibited remarkable efficacy against fungal strains such as Aspergillus fumigatus and Trichophyton rubrum, with MIC values as low as 1.56 μL/mL. Synergy tests revealed that combinations of clove, oregano, and thyme oils yielded significantly lower MIC values than individual oils, indicating additive or synergistic effects. The formulation of a soap incorporating clove and oregano oils demonstrated efficacy comparable to synthetic antiseptics in vivo. These findings highlight the exceptional antimicrobial potential of essential oils, mainly clove and oregano, against resistant microorganisms, offering a viable alternative to conventional antimicrobial agents. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 1343 KiB

Open AccessArticle

Activity of Common Thyme (Thymus vulgaris L.), Greek Oregano (Origanum vulgare L. ssp. hirtum), and Common Oregano (Origanum vulgare L. ssp. vulgare) Essential Oils against Selected Phytopathogens

by Olga Kosakowska, Zenon Węglarz, Sylwia Styczyńska, Alicja Synowiec, Małgorzata Gniewosz and Katarzyna Bączek

Molecules 2024, 29(19), 4617; https://doi.org/10.3390/molecules29194617 - 29 Sep 2024

Viewed by 1029

Abstract

The aim of this study was to determine the activity of common thyme (Thymus vulgare L.), Greek oregano (Origanum vulgare L. ssp. hirtum), and common oregano (Origanum vulgare L. ssp. vulgare) essential oils (EOs) against selected phytopathogenic microorganisms [...] Read more.

The aim of this study was to determine the activity of common thyme (Thymus vulgare L.), Greek oregano (Origanum vulgare L. ssp. hirtum), and common oregano (Origanum vulgare L. ssp. vulgare) essential oils (EOs) against selected phytopathogenic microorganisms in relation to their chemical profile. The EOs were obtained from the herbs of 2-year-old plants cultivated in the organic farming system in a temperate climate in Central Europe. The EOs’ composition was determined by GC/MS and GC/FID. The investigated species were represented by the following three chemotypes: ‘thymol’ for common thyme, ‘carvacrol’ for Greek oregano, and mixed ‘caryophyllene oxide + β-caryophyllene’ for common oregano. The antimicrobial activity of the EOs was assessed based on minimum inhibitory concentration (MIC) and minimum bactericidal/fungicidal concentration (MBC/MFC) values. The plant pathogenic bacteria Pseudomonas syringae, Xanthomonas hortorum, Erwinia carotovora, and fungi: Fusarium culmorum, Alternaria alternata, Botrytis cinerea, Epicoccum purpurascens, Cladosporium cladosporioides, Phoma strasseri, and Pythium debaryanum were tested. The EOs revealed a stronger inhibitory effect against fungal growth in comparison to bacterial growth (MIC: 0.016–2 µL/mL for fungi and 0.125–4 µL/mL for bacteria). Common thyme and Greek oregano EOs indicated stronger antimicrobial power than common oregano EO. These results were associated with the chemical profile of the analysed EOs. The growth of examined bacteria and fungi strains (in particular, X. hortorum, F. culmorum, and P. debaryanum) were negatively correlated with the content of phenolic monoterpenes and monoterpene hydrocarbons. Among the tested strains, P. strasseri turned out to be the most sensitive (MIC 0.016 µL/mL) and E. carotovora the most resistant (MIC 0.250–4 µL/mL) to all investigated EOs. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 903 KiB

Open AccessArticle

Cytotoxic Natural Products from the Jurassic Relict Osmunda regalis L.

by Andrea Estefania Carpinteyro Diaz, Lars Herfindal, Bjarte Holmelid, Cato Brede, Heidi Lie Andersen, Anni Vedeler and Torgils Fossen

Molecules 2024, 29(17), 4247; https://doi.org/10.3390/molecules29174247 - 7 Sep 2024

Viewed by 1007

Abstract

The Jurassic relict Royal fern, Osmunda regalis L., is widely distributed across temperate zones in the Northern and Southern hemispheres. Even though this species has been utilised for centuries as a medicinal plant, its phytochemical composition mainly remains unknown. As part of our [...] Read more.

The Jurassic relict Royal fern, Osmunda regalis L., is widely distributed across temperate zones in the Northern and Southern hemispheres. Even though this species has been utilised for centuries as a medicinal plant, its phytochemical composition mainly remains unknown. As part of our ongoing research to identify potential lead compounds for future anticancer drugs, 17 natural products were characterised from the aerial parts of Osmunda regalis L. Fifteen of these compounds were identified in this species for the first time, including the six previously undescribed compounds kaempferol 3-O-(2’’-O-(2’’’-α-rhamnopyranosyl)-β-glucopyranosyl)-β-glucopyranoside, quercetin 3-O-(2’’-O-(2’’’-α-rhamnopyranosyl)-β-glucopyranosyl)-β-glucopyranoside, kaempferol 3-O-(2’’-O-(2’’’-α-rhamnopyranosyl-6’’’-O-(E)-caffeoyl-)-β-glucopyranosyl)-β-glucopyranoside, 3-methoxy-5-hydroxy-4-olide, 4-hydroxy-3-(3’-hydroxy-4’-(hydroxyethyl)-oxotetrafuranone-5-methyl tetrahydropyranone, and 4-O-(5-hydroxy-4-oxohexanoyl) osmundalactone. The molecular structures were determined by combining several 1D and 2D NMR experiments, circular dichroism spectroscopy, and HRMS. Determination of cytotoxicity against AML MOLM-13, H9c2, and NRK cell lines showed that two isolated lactones exhibited significant cytotoxic activity. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 2880 KiB

Open AccessArticle

In Vitro Antiproliferative Activity of Echinulin Derivatives from Endolichenic Fungus Aspergillus sp. against Colorectal Cancer

by Hind Makhloufi, Aline Pinon, Yves Champavier, Jennifer Saliba, Marion Millot, Ingrid Fruitier-Arnaudin, Bertrand Liagre, Guillaume Chemin and Lengo Mambu

Molecules 2024, 29(17), 4117; https://doi.org/10.3390/molecules29174117 - 30 Aug 2024

Viewed by 850

Abstract

The endolichenic fungus Aspergillus sp. was isolated from the lichen Xanthoparmelia conspersa harvested in France. Aspergillus sp. was grown on a solid culture medium to ensure the large-scale production of the fungus with a sufficient mass of secondary metabolites. The molecular network analysis [...] Read more.

The endolichenic fungus Aspergillus sp. was isolated from the lichen Xanthoparmelia conspersa harvested in France. Aspergillus sp. was grown on a solid culture medium to ensure the large-scale production of the fungus with a sufficient mass of secondary metabolites. The molecular network analysis of extracts and subfractions enabled the annotation of 22 molecules, guiding the purification process. The EtOAc extract displayed an antiproliferative activity of 3.2 ± 0.4 µg/mL at 48 h against human colorectal cancer cells (HT-29) and no toxicity at 30 µg/mL against human triple-negative breast cancer (TNBC) cells (MDA-MB-231) and human embryonic kidney (HEK293) non-cancerous cells. Among the five prenylated compounds isolated, of which four are echinulin derivatives, compounds 1 and 2 showed the most important activity, with IC₅₀ values of 1.73 µM and 8.8 µM, respectively, against HT-29 cells. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 1411 KiB

Open AccessArticle

Antioxidant and Anti-Inflammatory Profiles of Two Mexican Heteropterys Species and Their Relevance for the Treatment of Mental Diseases: H. brachiata (L.) DC. and H. cotinifolia A. Juss. (Malpighiaceae)

by Antonio Nieto Camacho, Itzel Isaura Baca Ibarra and Maira Huerta-Reyes

Molecules 2024, 29(13), 3053; https://doi.org/10.3390/molecules29133053 - 27 Jun 2024

Viewed by 770

Abstract

Depression and anxiety are recognized as the most common mental diseases worldwide. New approaches have considered different therapeutic targets, such as oxidative stress and the inflammation process, due to their close association with the establishment and progression of mental diseases. In the present [...] Read more.

Depression and anxiety are recognized as the most common mental diseases worldwide. New approaches have considered different therapeutic targets, such as oxidative stress and the inflammation process, due to their close association with the establishment and progression of mental diseases. In the present study, we evaluated the antioxidant and anti-inflammatory activities of the methanolic extracts of the plant species Heteropterys brachiata and Heteropterys cotinifolia and their main compounds, chlorogenic acid and rutin, as potential complementary therapeutic tools for the treatment of anxiety and depression, since the antidepressant and anxiolytic activities of these methanolic extracts have been shown previously. Additionally, we also evaluated their inhibitory activity on the enzyme acetylcholinesterase (AChE). Our results revealed that both species exhibited potent antioxidant activity (>90%) through the TBARS assay, while by means of the DPPH assay, only H. cotinifolia exerted potent antioxidant activity (>90%); additionally, low metal chelating activity (<40%) was detected for all samples tested in the ferrozine assay. The methanolic extracts of H. brachiata and H. cotinifolia exhibited significant anti-inflammatory activities in the TPA-induced ear edema, while only H. cotinifolia exerted significant anti-inflammatory activities in the MPO assay (>45%) and also exhibited a higher percentage of inhibition on AChE of even twice (>80%) as high as the control in concentrations of 100 and 1000 µg/mL. Thus, the potent antioxidant and inflammatory properties and the inhibition of AChE may be involved in the antidepressant activities of the species H. cotinifolia, which would be positioned as a candidate for study in drug development as an alternative in the treatment of depression. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 1744 KiB

Open AccessArticle

Optimization of Extraction Conditions for Water-Soluble Polysaccharides from the Roots of Adenophora tetraphylla (Thunb.) Fisch. and Its Effects on Glucose Consumption on HepG2 Cells

by Junkai Wu, Xiaohang Zhou, Huifeng Sun and Dan Yu

Molecules 2024, 29(13), 3049; https://doi.org/10.3390/molecules29133049 - 27 Jun 2024

Cited by 1 | Viewed by 851

Abstract

The root of Adenophora tetraphylla (Thunb.) Fisch. is a common Chinese materia medica and the polysaccharides which have been isolated from the plant are important active components for medicinal purposes. The objective of the current study was to optimize the extraction parameters and [...] Read more.

The root of Adenophora tetraphylla (Thunb.) Fisch. is a common Chinese materia medica and the polysaccharides which have been isolated from the plant are important active components for medicinal purposes. The objective of the current study was to optimize the extraction parameters and evaluate the glucose consumption activity for Adenophorae root polysaccharides (ARPs). The optimization of ARP extraction was evaluated with preliminary experiments and using response surface methodology (RSM). The conditions investigated were 35–45 °C extraction temperature, 20–30 (v/w) water-to-solid ratio, and 3–5 h extraction time. The antidiabetic effects of ARPs for the glucose consumption activity were evaluated in HepG2 cells. The statistical analyses of the experiments indicated that temperature, water-to-solid ratio, and extraction time significantly affected ARP yield (p < 0.01). The correlation analysis revealed that the experimental data were well-aligned with a quadratic polynomial model, as evidenced by the mathematical regression model’s fit. The optimal conditions for maximum ARP yield were 45 °C extraction temperature and 28.47:1 (mL/g) water-to-solid ratio with a 4.60 h extraction time. Extracts from these conditions showed significant activity of promoting cell proliferation from 11.26% (p < 0.001) to 32.47% (p < 0.001) at a dose of 50 μg/mL to 800 μg/mL and increasing glucose consumption to 75.86% (p < 0.001) at 250 μg/mL on HepG2 cells. This study provides a sustainable alternative for the industry since it allowed simplified handling and a specific quantity of ARPs. Furthermore, ARPs might directly stimulate the glucose consumption in the liver and showed no cytotoxicity; therefore, ARPs probably could be taken as a potential natural source of antidiabetic materials. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 2156 KiB

Open AccessArticle

Supercritical Carbon Dioxide Extraction of Coumarins from the Aerial Parts of Pterocaulon polystachyum

by Júlia M. Scopel, Bruna Medeiros-Neves, Helder Ferreira Teixeira, Nathalya T. Brazil, Sérgio A. L. Bordignon, Fernando Mendonça Diz, Fernanda Bueno Morrone, Rafael N. Almeida, Eduardo Cassel, Gilsane L. von Poser and Rubem M. F. Vargas

Molecules 2024, 29(12), 2741; https://doi.org/10.3390/molecules29122741 - 8 Jun 2024

Cited by 2 | Viewed by 1489

Abstract

Pterocaulon polystachyum is a species of pharmacological interest for providing volatile and non-volatile extracts with antifungal and amebicidal properties. The biological activities of non-volatile extracts may be related to the presence of coumarins, a promising group of secondary metabolites. In the present study, [...] Read more.

Pterocaulon polystachyum is a species of pharmacological interest for providing volatile and non-volatile extracts with antifungal and amebicidal properties. The biological activities of non-volatile extracts may be related to the presence of coumarins, a promising group of secondary metabolites. In the present study, leaves and inflorescences previously used for the extraction of essential oils instead of being disposed of were subjected to extraction with supercritical CO₂ after pretreatment with microwaves. An experimental design was followed to seek the best extraction condition with the objective function being the maximum total extract. Pressure and temperature were statistically significant factors, and the optimal extraction condition was 240 bar, 60 °C, and pretreatment at 30 °C. The applied mathematical models showed good adherence to the experimental data. The extracts obtained by supercritical CO₂ were analyzed and the presence of coumarins was confirmed. The extract investigated for cytotoxicity against bladder tumor cells (T24) exhibited significant reduction in cell viability at concentrations between 6 and 12 μg/mL. The introduction of green technology, supercritical extraction, in the exploration of P. polystachyum as a source of coumarins represents a paradigm shift with regard to previous studies carried out with this species, which used organic solvents. Furthermore, the concept of circular bioeconomy was applied, i.e., the raw material used was the residue of a steam-distillation process. Therefore, the approach used here is in line with the sustainable exploitation of native plants to obtain extracts rich in coumarins with cytotoxic potential against cancer cells. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 4684 KiB

Open AccessArticle

L-Theanine Prolongs the Lifespan by Activating Multiple Molecular Pathways in Ultraviolet C-Exposed Caenorhabditis elegans

by Liangwen Chen, Guijie Chen, Tingting Gai, Xiuhong Zhou, Jinchi Zhu, Ruiyi Wang, Xuemei Wang, Yujie Guo, Yun Wang and Zhongwen Xie

Molecules 2024, 29(11), 2691; https://doi.org/10.3390/molecules29112691 - 6 Jun 2024

Viewed by 1616

Abstract

L-theanine, a unique non-protein amino acid, is an important bioactive component of green tea. Previous studies have shown that L-theanine has many potent health benefits, such as anti-anxiety effects, regulation of the immune response, relaxing neural tension, and reducing oxidative damage. However, little [...] Read more.

L-theanine, a unique non-protein amino acid, is an important bioactive component of green tea. Previous studies have shown that L-theanine has many potent health benefits, such as anti-anxiety effects, regulation of the immune response, relaxing neural tension, and reducing oxidative damage. However, little is known concerning whether L-theanine can improve the clearance of mitochondrial DNA (mtDNA) damage in organisms. Here, we reported that L-theanine treatment increased ATP production and improved mitochondrial morphology to extend the lifespan of UVC-exposed nematodes. Mechanistic investigations showed that L-theanine treatment enhanced the removal of mtDNA damage and extended lifespan by activating autophagy, mitophagy, mitochondrial dynamics, and mitochondrial unfolded protein response (UPR^mt) in UVC-exposed nematodes. In addition, L-theanine treatment also upregulated the expression of genes related to mitochondrial energy metabolism in UVC-exposed nematodes. Our study provides a theoretical basis for the possibility that tea drinking may prevent mitochondrial-related diseases. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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16 pages, 2317 KiB

Open AccessArticle

Chamaecyparis lawsoniana and Its Active Compound Quercetin as Ca²⁺ Inhibitors in the Contraction of Airway Smooth Muscle

by Edgar Flores-Soto, Bianca S. Romero-Martínez, Héctor Solís-Chagoyán, Edgar A. Estrella-Parra, Jose G. Avila-Acevedo, Juan C. Gomez-Verjan, Jorge Reyes-García, María F. Casas-Hernández, Bettina Sommer and Luis M. Montaño

Molecules 2024, 29(10), 2284; https://doi.org/10.3390/molecules29102284 - 12 May 2024

Cited by 1 | Viewed by 1239

Abstract

The Cupressaceae family includes species considered to be medicinal. Their essential oil is used for headaches, colds, cough, and bronchitis. Cedar trees like Chamaecyparis lawsoniana (C. lawsoniana) are commonly found in urban areas. We investigated whether C. lawsoniana exerts some of [...] Read more.

The Cupressaceae family includes species considered to be medicinal. Their essential oil is used for headaches, colds, cough, and bronchitis. Cedar trees like Chamaecyparis lawsoniana (C. lawsoniana) are commonly found in urban areas. We investigated whether C. lawsoniana exerts some of its effects by modifying airway smooth muscle (ASM) contractility. The leaves of C. lawsoniana (363 g) were pulverized mechanically, and extracts were obtained by successive maceration 1:10 (w:w) with methanol/CHCl₃. Guinea pig tracheal rings were contracted with KCl, tetraethylammonium (TEA), histamine (HIS), or carbachol (Cch) in organ baths. In the Cch experiments, tissues were pre-incubated with D-600, an antagonist of L-type voltage-dependent Ca²⁺ channels (L-VDCC) before the addition of C. lawsoniana. Interestingly, at different concentrations, C. lawsoniana diminished the tracheal contractions induced by KCl, TEA, HIS, and Cch. In ASM cells, C. lawsoniana significantly diminished L-type Ca²⁺ currents. ASM cells stimulated with Cch produced a transient Ca²⁺ peak followed by a sustained plateau maintained by L-VDCC and store-operated Ca²⁺ channels (SOCC). C. lawsoniana almost abolished this last response. These results show that C. lawsoniana, and its active metabolite quercetin, relax the ASM by inhibiting the L-VDCC and SOCC; further studies must be performed to obtain the complete set of metabolites of the extract and study at length their pharmacological properties. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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14 pages, 7076 KiB

Open AccessArticle

Antimicrobial Activity and Phytochemical Characterization of Baccharis concava Pers., a Native Plant of the Central Chilean Coast

by Maité Rodríguez-Díaz, Fabián E. Pérez, Paloma M. Manosalva, Juan I. Cerda, Consuelo F. Martínez-Contreras, Aracely Y. Mora, Nicolás A. Villagra, Sergio A. Bucarey, Andrés Barriga, Jorge Escobar, José L. Martínez and Alejandro A. Hidalgo

Molecules 2024, 29(7), 1654; https://doi.org/10.3390/molecules29071654 - 7 Apr 2024

Cited by 3 | Viewed by 1487

Abstract

Few sclerophyllous plants from the central coast of Chile have been systematically studied. This work describes the phytochemical composition and antimicrobial properties of Baccharis concava Pers. (sin. B. macraei), a shrub found in the first line and near the Pacific coast. B. [...] Read more.

Few sclerophyllous plants from the central coast of Chile have been systematically studied. This work describes the phytochemical composition and antimicrobial properties of Baccharis concava Pers. (sin. B. macraei), a shrub found in the first line and near the Pacific coast. B. concava has been traditionally used by indigenous inhabitants of today’s central Chile for its medicinal properties. Few reports exist regarding the phytochemistry characterization and biological activities of B. concava. A hydroalcoholic extract of B. concava was prepared from leaves and small branches. Qualitative phytochemical characterization indicated the presence of alkaloids, steroids, terpenoids, flavonoids, phenolic, and tannin compounds. The antimicrobial activity of this extract was assessed in a panel of microorganisms including Gram-positive bacteria, Gram-negative bacteria, and pathogenic yeasts. The extract displayed an important antimicrobial effect against Gram-positive bacteria, Candida albicans, and Cryptococcus neoformans but not against Gram-negatives, for which an intact Lipopolysaccharide is apparently the determinant of resistance to B. concava extracts. The hydroalcoholic extract was then fractionated through a Sephadex LH-20/methanol–ethyl acetate column. Afterward, the fractions were pooled according to a similar pattern visualized by TLC/UV analysis. Fractions obtained by this criterion were assessed for their antimicrobial activity against Staphylococcus aureus. The fraction presenting the most antimicrobial activity was HPLC-ESI-MS/MS, obtaining molecules related to caffeoylquinic acid, dicaffeoylquinic acid, and quercetin, among others. In conclusion, the extracts of B. concava showed strong antimicrobial activity, probably due to the presence of metabolites derived from phenolic acids, such as caffeoylquinic acid, and flavonoids, such as quercetin, which in turn could be responsible for helping with wound healing. In addition, the development of antimicrobial therapies based on the molecules found in B. concava could help to combat infection caused by pathogenic yeasts and Gram-positive bacteria, without affecting the Gram-negative microbiota. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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11 pages, 4961 KiB

Open AccessArticle

Anticancer Potential and Safety Profile of β-Lapachone In Vitro

by Karina Motta Melo Lima, Luana França Calandrini de Azevedo, Jorge Dores Rissino, Valdicley Vieira Vale, Erica Vanessa Souza Costa, Maria Fani Dolabela, Cleusa Yoshiko Nagamachi and Julio Cesar Pieczarka

Molecules 2024, 29(6), 1395; https://doi.org/10.3390/molecules29061395 - 21 Mar 2024

Cited by 1 | Viewed by 1523

Abstract

Ipê is a plant of the Bignoniaceae family. Among the compounds extracted from this tree, lapachol is notable because its structural modification allows the production of β-lapachone, which has anticancer properties. The objective of this work was to test this hypothesis at a [...] Read more.

Ipê is a plant of the Bignoniaceae family. Among the compounds extracted from this tree, lapachol is notable because its structural modification allows the production of β-lapachone, which has anticancer properties. The objective of this work was to test this hypothesis at a cellular level in vitro and assess its potential safety for use. The following tests were performed: MTT cell viability assay, apoptotic index determination, comet assay, and micronucleus test. The results showed that β-lapachone had a high cytotoxic capacity for all cell lines tested: ACP02 (gastric adenocarcinoma cells), MCF7 (breast carcinoma cells), HCT116 (colon cancer cells) and HEPG2 (hepatocellular carcinoma cells). Regarding genotoxicity, the exposure of cells to sublethal doses of β-lapachone induced DNA damage (assessed by the comet assay) and nuclear abnormalities, such as nucleoplasmic bridges and nuclear buds (assessed by the micronucleus test). All tested cell lines responded similarly to β-lapachone, except for ACP02 cells, which were relatively resistant to the cytotoxic effects of the compound in the MTT test. Our results collectively indicate that although β-lapachone showed antiproliferative activity against cancer cell lines, it also caused harmful effects in these cells, suggesting that the use of β-lapachone in treating cancer should be carried out with caution. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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20 pages, 12477 KiB

Open AccessArticle

Anti-Psoriatic Activity of Black, Green and White Tea Extracts from Southeastern China

by Lanyue Zhang, Zeting Huang, Jie Xuan, Lu Yang, Tiantian Zhao and Weihua Peng

Molecules 2024, 29(6), 1279; https://doi.org/10.3390/molecules29061279 - 13 Mar 2024

Cited by 1 | Viewed by 1794

Abstract

Psoriasis is a common chronic inflammatory disease, but most of its current treatments come with a high risk of side effects. As one of the world’s top three beverages, tea has a traditional history of being used as a treatment for skin conditions [...] Read more.

Psoriasis is a common chronic inflammatory disease, but most of its current treatments come with a high risk of side effects. As one of the world’s top three beverages, tea has a traditional history of being used as a treatment for skin conditions due to its high safety profile, anti-inflammatory and other properties. In this study, we investigated the anti-psoriasis effects of ethanol extracts of black tea, green tea and white tea from southeastern China. The compositions of the tea extracts (TEs) were first determined by UPLC-Q-Exactive-Orbitrap MS and then genetic analysis, antibacterial, anti-inflammatory, and immunocompetence assays were performed. Imiquimod was used to establish a mouse model of psoriasis-like dermatitis and treating with the extracts to examine their efficacy. A total of 88 chemical components, mainly phenols and organic acids, were identified from the TEs. These TEs ameliorated skin damage and they all reduced the expression of cytokines IL-17 and TNF-α. By analyzing the genes, TEs may affect the inflammatory signaling pathway by regulating the metabolic changes. In addition, TEs can significantly scavenge ROS, NO, and inhibit cellular inflammation. In conclusion, this study examined the inhibitory effects of three TEs on psoriasis and their potential as nutritional supplements for the treatment of skin inflammation. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 13944 KiB

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Atractylenolide II Suppresses Glycolysis and Induces Apoptosis by Blocking the PADI3-ERK Signaling Pathway in Endometrial Cancer Cells

by Shuang Tian, Lili Ren, Chao Liu and Zhe Wang

Molecules 2024, 29(5), 939; https://doi.org/10.3390/molecules29050939 - 21 Feb 2024

Cited by 1 | Viewed by 1427

Abstract

Atractylenolide II (AT-II), the major bioactive compound of Atractylodes macrocephala, exhibits anti-cancer activity against many types of tumors, but the roles and the potential mechanisms in endometrial cancer remain unclear. In the present study, AT-II treatment was found to significantly suppress RL95-2 [...] Read more.

Atractylenolide II (AT-II), the major bioactive compound of Atractylodes macrocephala, exhibits anti-cancer activity against many types of tumors, but the roles and the potential mechanisms in endometrial cancer remain unclear. In the present study, AT-II treatment was found to significantly suppress RL95-2 and AN3CA cell proliferation and glycolysis, and induced their apoptosis by inactivating the ERK signaling pathway, accompanied by the changing expression of the glycolytic key enzymes and apoptotic-related proteins. Peptidyl arginine deiminase 3 (PADI3), as the candidate target gene of AT-II, was highly expressed in the endometrial cancer tissues and associated with a poor prognosis according to bioinformatics analysis. PADI3 knockdown inhibited proliferation and glycolysis in endometrial cancer cells and induced cell apoptosis. Furthermore, AT-II negatively regulated the expression of PADI3, and PADI3 overexpression reversed the effects of AT-II on endometrial cancer cells. Our findings suggested that the anti-cancer function of AT-II is associated with the suppression of glycolysis and induction of apoptosis by blocking the PADI3-ERK signaling pathway. Thus, AT-II represents a novel therapeutic target for endometrial cancer and targeting AT-II may serve as a potential strategy for the clinical therapy of endometrial cancer. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 2498 KiB

Open AccessArticle

Naphthoquinone Derivatives from Angustimassarina populi CF-097565 Display Anti-Tumour Activity in 3D Cultures of Breast Cancer Cells

by Thomas A. Mackenzie, Fernando Reyes, Marta Martínez, Víctor González-Menéndez, Isabel Sánchez, Olga Genilloud, José R. Tormo and María C. Ramos

Molecules 2024, 29(2), 425; https://doi.org/10.3390/molecules29020425 - 15 Jan 2024

Cited by 3 | Viewed by 1692

Abstract

Cancer is one of the leading causes of death worldwide, with breast cancer being the second cause of cancer-related mortality among women. Natural Products (NPs) are one of the main sources for drug discovery. During a screening campaign focused on the identification of [...] Read more.

Cancer is one of the leading causes of death worldwide, with breast cancer being the second cause of cancer-related mortality among women. Natural Products (NPs) are one of the main sources for drug discovery. During a screening campaign focused on the identification of extracts from Fundación MEDINA’s library inhibiting the proliferation of cancer cell lines, a significant bioactivity was observed in extracts from cultures of the fungus Angustimassarina populi CF-097565. Bioassay-guided fractionation of this extract led to the identification and isolation of herbarin (1), 1-hydroxydehydroherbarin (4) plus other three naphthoquinone derivatives of which 3 and 5 are new natural products and 2 is herein described from a natural source for the first time. Four of these compounds (1, 3, 4 and 5) confirmed a specific cytotoxic effect against the human breast cancer cell line MCF-7. To evaluate the therapeutic potential of the compounds isolated, their efficacy was validated in 3D cultures, a cancer model of higher functionality. Additionally, an in-depth study was carried out to test the effect of the compounds in terms of cell mortality, sphere disaggregation, shrinkage, and morphology. The cell profile of the compounds was also compared to that of known cytotoxic compounds with the aim to distinguish the drug mode of action (MoA). The profiles of 1, 3 and 4 showed more biosimilarity between them, different to 5, and even more different to other known cytotoxic agents, suggesting an alternative MoA responsible for their cytotoxicity in 3D cultures. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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10 pages, 1372 KiB

Open AccessArticle

Isolation and Characterization of Antimicrobial Metabolites from the Sophora tonkinensis-Associated Fungus Penicillium sp. GDGJ-N37

by Lili Huang, Yongxia Li, Jing Pang, Liuxia Lv, Jiatong Zhou, Liqi Liang, Xianhua He, Jun Li, Weifeng Xu and Ruiyun Yang

Molecules 2024, 29(2), 348; https://doi.org/10.3390/molecules29020348 - 10 Jan 2024

Cited by 3 | Viewed by 23238

Abstract

Chemical investigation of Penicillium sp. GDGJ-N37, a Sophora tonkinensis-associated fungus, yielded two new azaphilone derivatives, N-isoamylsclerotiorinamine (1) and 7-methoxyl-N-isoamylsclerotiorinamine (2), and four known azaphilones (3–6), together with two new chromone derivatives, penithochromones [...] Read more.

Chemical investigation of Penicillium sp. GDGJ-N37, a Sophora tonkinensis-associated fungus, yielded two new azaphilone derivatives, N-isoamylsclerotiorinamine (1) and 7-methoxyl-N-isoamylsclerotiorinamine (2), and four known azaphilones (3–6), together with two new chromone derivatives, penithochromones X and Y (7 and 8). Their structures were elucidated based on spectroscopic data, CD spectrum, and semi-synthesis. Sclerotioramine (3) showed significant antibacterial activities against B. subtilis and S. dysentery, and it also showed most potent anti-plant pathogenic fungi activities against P. theae, C. miyabeanus, and E. turcicum. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 2576 KiB

Open AccessArticle

Benzofuran Derivatives from Cortex Mori Radicis and Their Cholinesterase-Inhibitory Activity

by Xiang Cui, Zehong Huang, Shanshan Deng, Yunxia Zhang, Guoyin Li, Lining Wang, Yanru Deng and Changjing Wu

Molecules 2024, 29(2), 315; https://doi.org/10.3390/molecules29020315 - 8 Jan 2024

Viewed by 1252

Abstract

The phytochemical investigation of Cortex Mori Radicis led to the isolation and identification of a new prenylated benzofuranone (1) and four ring-opening derivatives (2–5) named albaphenol A–E, as well as nigranol A (6), together with [...] Read more.

The phytochemical investigation of Cortex Mori Radicis led to the isolation and identification of a new prenylated benzofuranone (1) and four ring-opening derivatives (2–5) named albaphenol A–E, as well as nigranol A (6), together with ten 2-arylbenzofuran derivatives (7–16). The characterization of the structures of the new compounds and the structural revision of nigranol A (6) were conducted using the comprehensive analysis of spectroscopic data (1D/2D NMR, HRESIMS, CD, and XRD). Compounds 1–16 were tested for their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Compounds 1 and 4 showed weak BChE-inhibitory activity (IC₅₀ 45.5 and 61.0 μM); six 2-arylbenzofuran derivatives showed more-potent BChE-inhibitory activity (IC₅₀ 2.5–32.8 μM) than the positive control galantamine (IC₅₀ 35.3 μM), while being inactive or weakly inhibitory toward AChE. Cathafuran C (14) exhibited the most potent and selective inhibitory activity against BChE in a competitive manner, with a Ki value of 1.7 μM. The structure–activity relationships of the benzofuran-type stilbenes were discussed. Furthermore, molecular docking and dynamic simulations were performed to clarify the interactions of the inhibitor–enzyme complex. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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16 pages, 3225 KiB

Open AccessArticle

In Vitro and In Silico Activities of E. radiata and E. cinerea as an Enhancer of Antibacterial, Antioxidant, and Anti-Inflammatory Agents

by Hayet Elkolli, Meriem Elkolli, Farid S. Ataya, Mounir M. Salem-Bekhit, Sami Al Zahrani, Mostafa W. M. Abdelmageed, Barbara Ernst and Yacine Benguerba

Molecules 2023, 28(20), 7153; https://doi.org/10.3390/molecules28207153 - 18 Oct 2023

Viewed by 1970

Abstract

Eucalyptus, a therapeutic plant mentioned in the ancient Algerian pharmacopeia, specifically two species belonging to the Myrtaceae family, E. radiata and E. cinerea, were investigated in this study for their antibacterial, antioxidant, and anti-inflammatory properties. The study used aqueous [...] Read more.

Eucalyptus, a therapeutic plant mentioned in the ancient Algerian pharmacopeia, specifically two species belonging to the Myrtaceae family, E. radiata and E. cinerea, were investigated in this study for their antibacterial, antioxidant, and anti-inflammatory properties. The study used aqueous extracts (AE) obtained from these plants, and the extraction yields were found to be different. The in vitro antibacterial activity was evaluated using a disc diffusion assay against three typical bacterial strains. The results showed that the two extracts were effective against all three strains. Both extracts displayed significant antioxidant activity compared to BHT. The anti-inflammatory impact was evaluated using a protein (BSA) inhibition denaturation test. The E. radiata extract was found to inhibit inflammation by 85% at a concentration of 250 µg/mL, significantly higher than the Aspirin. All phytoconstituents present good pharmacokinetic characteristics without toxicity except very slight toxicity of terpineol and cineol and a maximum binding energy of −7.53 kcal/mol for its anti-TyrRS activity in silico. The study suggests that the extracts and their primary phytochemicals could enhance the efficacy of antibiotics, antioxidants, and non-steroidal anti-inflammatory drugs (NSAIDs). As pharmaceutical engineering experts, we believe this research contributes to developing natural-based drugs with potential therapeutic benefits. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 4152 KiB

Open AccessArticle

Total Flavonoids from Camellia oleifera Alleviated Mycoplasma pneumoniae-Induced Lung Injury via Inhibition of the TLR2-Mediated NF-κB and MAPK Pathways

by Nan Ding, Aihua Lei, Zhisheng Shi, Lin Xiang, Bo Wei and Yimou Wu

Molecules 2023, 28(20), 7077; https://doi.org/10.3390/molecules28207077 - 13 Oct 2023

Cited by 1 | Viewed by 2389

Abstract

Mycoplasma pneumoniae (M. pneumoniae) is an atypical bacterial pathogen responsible for community-acquired pneumonia primarily among school-aged children and young adults. Camellia oleifera (C. oleifera) has been used as a medicinal and edible plant in China for centuries, the constituents [...] Read more.

Mycoplasma pneumoniae (M. pneumoniae) is an atypical bacterial pathogen responsible for community-acquired pneumonia primarily among school-aged children and young adults. Camellia oleifera (C. oleifera) has been used as a medicinal and edible plant in China for centuries, the constituents from which possessed various bioactivities. Notably, flavonoids existing in residues of C. oleifera defatted seeds exhibited significant anti-inflammatory activities. In the present study, we investigated the impact of total flavonoids from C. oleifera (TFCO) seed extract on M. pneumoniae pneumonia. TFCO was obtained using multiple column chromatography methods and identified as kaempferol glycosides via UPLC-HRESIMS. In a M. pneumoniae pneumonia mouse model, TFCO significantly reduced the lung damage, suppressed IL-1β, IL-6, and TNF-α production, and curbed TLR2 activation triggered by M. pneumoniae. Similarly, in RAW264.7 macrophage cells stimulated by lipid-associated membrane proteins (LAMPs), TFCO suppressed the generation of proinflammatory cytokines and TLR2 expression. Moreover, TFCO diminished the phosphorylation of IκBα, JNK, ERK, p38, and p65 nuclear translocation in vitro. In conclusion, TFCO alleviated M. pneumoniae-induced lung damage via inhibition of TLR2-mediated NF-κB and MAPK pathways, suggesting its potential therapeutic application in M. pneumoniae-triggered lung inflammation. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 704 KiB

Open AccessArticle

Effect of Industrial Pollution in Puchuncaví Valley on the Medicinal Properties of Senecio fistulosus Poepp. ex Les (Asteraceae): Content of Phytoconstituents and Their Antioxidant and Cytotoxic Activities

by Manuel Martínez-Lobos, Estela Tapia-Venegas, Paula Celis-Plá, Joan Villena, Carlos Jara-Gutiérrez, Alexandra Lobos Pessini and Alejandro Madrid-Villegas

Molecules 2023, 28(20), 7038; https://doi.org/10.3390/molecules28207038 - 12 Oct 2023

Cited by 1 | Viewed by 1213

Abstract

Senecio fistulosus, an endemic plant in Chile, is highly regarded for its medicinal properties and is popular in alternative medicine. It thrives even in polluted areas, like Puchuncaví Valley, Chile. Therefore, the study aimed to assess the impact of industrial pollution in [...] Read more.

Senecio fistulosus, an endemic plant in Chile, is highly regarded for its medicinal properties and is popular in alternative medicine. It thrives even in polluted areas, like Puchuncaví Valley, Chile. Therefore, the study aimed to assess the impact of industrial pollution in Puchuncaví Valley, Chile, on the phytoconstituent content, as well as the antioxidant and cytotoxic activities, of S. fistulosus. Phenols, flavonoids, and anthraquinones content were measured, alongside the assessment of antioxidant activities. Additionally, a GC-MS analysis was conducted to profile the phytoconstituents, while the cytotoxic potential was evaluated in HT-29 and MCF-7 and cell line non-tumorigenic MCF-10. The Wild sample exhibited a greater concentration of phytoconstituents (0 to 169.48 mg·L⁻¹) compared to the Commercial control (0 to 95.38 mg·L⁻¹), directly correlating with its antioxidant activity. While the Wild species showed cytotoxic activity, the Commercial control demonstrated cytotoxic effects on MCF-10 and MCF-7. Noteworthy compounds identified were hexadecanoic acid (12.76 to 19.57% relative area) and (Z,Z,Z)-9,12,15-octadecatrienoic acid (18.36% relative area), with anticancer properties. In conclusion, the abiotic stress experienced by S. fistulosus led to higher phytoconstituent content and improved antioxidant activity when contrasted with the Commercial control. The Commercial species showed increased cytotoxic activity against both tumorigenic and non-tumorigenic cell lines. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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25 pages, 2790 KiB

Open AccessArticle

Optimized Extraction of Polyphenols from Unconventional Edible Plants: LC-MS/MS Profiling of Polyphenols, Biological Functions, Molecular Docking, and Pharmacokinetics Study

by Hafiza Sehrish Kiani, Waheed Ahmad, Sana Nawaz, Mohammad Abul Farah and Akhtar Ali

Molecules 2023, 28(18), 6703; https://doi.org/10.3390/molecules28186703 - 19 Sep 2023

Cited by 9 | Viewed by 2890

Abstract

Plant bioactive phenolic metabolites have recently attracted the attention of researchers due to their numerous health advantages. Therefore, this study aimed to investigate with advanced techniques the bioactive metabolites and antioxidant and antidiabetic capacity of four unconventional edible plant leaves: lemongrass (Cymbopogon [...] Read more.

Plant bioactive phenolic metabolites have recently attracted the attention of researchers due to their numerous health advantages. Therefore, this study aimed to investigate with advanced techniques the bioactive metabolites and antioxidant and antidiabetic capacity of four unconventional edible plant leaves: lemongrass (Cymbopogon citratus (DC.) Stapf), chicory (Cichorium intybus L.), moringa (Moringa oleifera Lam.), and ryegrass (Lolium perenne L.). The extraction process was optimized using different solvents. These plants’ phenolic composition, identification, and characterization have been determined herein using LCESI-QTOF-MS/MS. This research identified 85 phenolic compounds, including 24 phenolic acids, 31 flavonoids, 7 stilbenes and lignans, and 17 other metabolites. Moreover, the study determined that moringa has the highest total phenolic content (TPC; 18.5 ± 1.01 mg GAE/g), whereas ryegrass has the lowest (3.54 ± 0.08 mg GAE/g) among the selected plants. It seems that, compared to other plants, moringa was found to have the highest antioxidant potential and antidiabetic potential. In addition, twenty-two phenolic compounds were quantified in these chosen edible plants. Rosmarinic acid, chlorogenic acid, chicoric acid, ferulic acid, protocatechuic acid, and caffeic acid were the most abundant phenolic acids. In silico molecular docking was also conducted to investigate the structure–function relationship of phenolic compounds to inhibit the alpha-glucosidase. Finally, the simulated pharmacokinetic characteristics of the most common substances were also predicted. In short, this investigation opens the way for further study into these plants’ pharmaceutical and dietary potential. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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14 pages, 1828 KiB

Open AccessArticle

Immunomodulatory Activity of Polysaccharides Isolated from Saussurea salicifolia L. and Saussurea frolovii Ledeb

by Igor A. Schepetkin, Marina G. Danilets, Anastasia A. Ligacheva, Evgenia S. Trofimova, Natalia S. Selivanova, Evgenii Yu. Sherstoboev, Sergei V. Krivoshchekov, Ekaterina I. Gulina, Konstantin S. Brazovskii, Liliya N. Kirpotina, Mark T. Quinn and Mikhail V. Belousov

Molecules 2023, 28(18), 6655; https://doi.org/10.3390/molecules28186655 - 16 Sep 2023

Cited by 3 | Viewed by 2015

Abstract

The genus Saussurea has been used in the preparation of therapies for a number of medical problems, yet not much is known about the therapeutic high-molecular-weight compounds present in extracts from these plants. Since polysaccharides are important in immune modulation, we investigated the [...] Read more.

The genus Saussurea has been used in the preparation of therapies for a number of medical problems, yet not much is known about the therapeutic high-molecular-weight compounds present in extracts from these plants. Since polysaccharides are important in immune modulation, we investigated the chemical composition and immunomodulatory activity of Saussurea salicifolia L. and Saussurea frolovii Ledeb polysaccharides. Water-soluble polysaccharides from the aerial parts of these plants were extracted using water at pHs of 2 and 6 and subsequently precipitated in ethanol to obtain fractions SSP2 and SSP6 from S. salicifolia and fractions SSF2 and SSF6 from S. frolovii. The molecular weights of fractions SSP2, SSP6, SFP2, and SFP6 were estimated to be 143.7, 113.2, 75.3, and 64.3 kDa, respectively. The polysaccharides from S. frolovii contained xylose (67.1–71.7%) and glucose (28.3–32.9%), whereas the polysaccharides from S. frolovii contained xylose (63.1–76.7%), glucose (11.8–19.2%), galactose (4.7–8.3%), and rhamnose (6.8–9.4%). Fractions SSP2, SSP6, and SFP2 stimulated nitric oxide (NO) production by murine macrophages, and NO production induced by SSP2, SSP6, and SFP2 was not inhibited by polymyxin B treatment of the fractions, whereaspolymyxin B treatment diminished the effects of SFP6, suggesting that SFP6 could contain lipopolysaccharide (LPS). The LPS-free fractions SSP2, SSP6, and SFP2 had potent immunomodulatory activity, induced NO production, and activated transcription factors NF-κB/AP-1 in human monocytic THP-1 cells and cytokine production by human MonoMac-6 monocytic cells, including interleukin (IL)-1α, IL-1β, IL-6, granulocyte macrophage colony-stimulating factor (GM-CSF), interferon-γ, monocyte chemotactic protein 1 (MCP-1), and tumor necrosis factor (TNF). These data suggest that at least part of the beneficial therapeutic effects reported for water extracts of the Saussurea species are due to the modulation of leukocyte functions by polysaccharides. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 4974 KiB

Open AccessArticle

Analysis of the Antibacterial Properties of Compound Essential Oil and the Main Antibacterial Components of Unilateral Essential Oils

by Anjiu Zhao, You Zhang, Feng Li, Lin Chen and Xingyan Huang

Molecules 2023, 28(17), 6304; https://doi.org/10.3390/molecules28176304 - 28 Aug 2023

Cited by 5 | Viewed by 2385

Abstract

Plant essential oils are widely used in food, medicine, cosmetics, and other fields because of their bacteriostatic properties and natural sources. However, the bacteriostatic range of unilateral essential oils is limited, and compound essential oil has become an effective way to improve the [...] Read more.

Plant essential oils are widely used in food, medicine, cosmetics, and other fields because of their bacteriostatic properties and natural sources. However, the bacteriostatic range of unilateral essential oils is limited, and compound essential oil has become an effective way to improve the antibacterial properties of unilateral essential oils. In this study, based on the analysis of the antibacterial properties of Chinese cinnamon bark oil and oregano oil, the proportion and concentration of the compound essential oil were optimized and designed, and the antibacterial activity of the compound essential oil was studied. The results showed that the antibacterial activity of Chinese cinnamon bark oil was higher than that of oregano oil. The compound essential oil prepared by a 1:1 ratio of Chinese cinnamon bark oil and oregano oil with a concentration of 156.25 ppm showed an excellent antibacterial activity against Escherichia coli and Staphylococcus aureus. The GC-MS results showed that cinnamaldehyde was the main antibacterial component of Chinese cinnamon bark essential oil, and carvacrol and thymol in oregano oil were the main antibacterial components. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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21 pages, 4295 KiB

Open AccessArticle

Marine Natural Compound (Neviotin A) Displays Anticancer Efficacy by Triggering Transcriptomic Alterations and Cell Death in MCF-7 Cells

by Quaiser Saquib, Stefan Schwaiger, Mostafa Alilou, Sarfaraz Ahmed, Maqsood A. Siddiqui, Javed Ahmad, Mohammad Faisal, Eslam M. Abdel-Salam, Rizwan Wahab, Adnan J. Al-Rehaily, Hermann Stuppner and Abdulaziz A. Al-Khedhairy

Molecules 2023, 28(17), 6289; https://doi.org/10.3390/molecules28176289 - 28 Aug 2023

Cited by 2 | Viewed by 1753

Abstract

We investigated the anticancer mechanism of a chloroform extract of marine sponge (Haliclona fascigera) (sample C) in human breast adenocarcinoma (MCF-7) cells. Viability analysis using MTT and neutral red uptake (NRU) assays showed that sample C exposure decreased the proliferation of [...] Read more.

We investigated the anticancer mechanism of a chloroform extract of marine sponge (Haliclona fascigera) (sample C) in human breast adenocarcinoma (MCF-7) cells. Viability analysis using MTT and neutral red uptake (NRU) assays showed that sample C exposure decreased the proliferation of cells. Flow cytometric data exhibited reactive oxygen species (ROS), nitric oxide (NO), dysfunction of mitochondrial potential, and apoptosis in sample C-treated MCF-7 cells. A qPCR array of sample C-treated MCF-7 cells showed crosstalk between different pathways of apoptosis, especially BIRC5, BCL2L2, and TNFRSF1A genes. Immunofluorescence analysis affirmed the localization of p53, bax, bcl2, MAPKPK2, PARP-1, and caspase-3 proteins in exposed cells. Bioassay-guided fractionation of sample C revealed Neviotin A as the most active compound triggering maximum cell death in MCF-7, indicating its pharmacological potency for the development of a drug for the treatment of human breast cancer. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 2618 KiB

Open AccessArticle

New Phenolic Lipids from the Leaves of Clausena harmandiana Inhibit SARS-CoV-2 Entry into Host Cells

by Marion Chambon, Charline Herrscher, Dana Al Halabi, Nathan François, Sandrine Belouzard, Stéphanie Boutet, Van Cuong Pham, Thi Mai Huong Doan, Karin Séron, Patrick Mavingui, Marc Litaudon, Chaker El Kalamouni and Cécile Apel

Molecules 2023, 28(14), 5414; https://doi.org/10.3390/molecules28145414 - 14 Jul 2023

Cited by 2 | Viewed by 1634

Abstract

Induced by the spread of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the COVID-19 pandemic underlined the clear need for antivirals against coronaviruses. In an effort to identify new inhibitors of SARS-CoV-2, a screening of 824 extracts prepared from various parts of 400 [...] Read more.

Induced by the spread of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2), the COVID-19 pandemic underlined the clear need for antivirals against coronaviruses. In an effort to identify new inhibitors of SARS-CoV-2, a screening of 824 extracts prepared from various parts of 400 plant species belonging to the Rutaceae and Annonaceae families was conducted using a cell-based HCoV-229E inhibition assay. Due to its significant activity, the ethyl acetate extract of the leaves of Clausena harmandiana was selected for further chemical and biological investigations. Mass spectrometry-guided fractionation afforded three undescribed phenolic lipids (1–3), whose structures were determined via spectroscopic analysis. The absolute configurations of 1 and 2 were determined by analyzing Mosher ester derivatives. The antiviral activity against SARS-CoV-2 was subsequently shown, with IC₅₀ values of 0.20 and 0.05 µM for 2 and 3, respectively. The mechanism of action was further assessed, showing that both 2 and 3 are inhibitors of coronavirus entry by acting directly on the viral particle. Phenolic lipids from Clausena harmandiana might be a source of new antiviral agents against human coronaviruses. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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16 pages, 6068 KiB

Open AccessArticle

A Novel Bromophenol Compound from Leathesia nana Inhibits Breast Cancer in a Direct Tumor Killing and Immunotherapy Manner

by Ruochen Sun, Mi Zhang, Bufan Li, Shan Jiang, Wanpeng Yu, Lina Yang, Yantao Han, Zhangfeng Zhong and Wenwen Zhao

Molecules 2023, 28(14), 5349; https://doi.org/10.3390/molecules28145349 - 12 Jul 2023

Cited by 3 | Viewed by 2193

Abstract

Considering the resistance and toxicity of traditional chemotherapeutic drugs, seeking potential candidate for treating breast cancer effectively is a clinical problem that should be solved urgently. Natural products have attracted extensive attention, owing to their multi-target advantages and low toxicity. In the current [...] Read more.

Considering the resistance and toxicity of traditional chemotherapeutic drugs, seeking potential candidate for treating breast cancer effectively is a clinical problem that should be solved urgently. Natural products have attracted extensive attention, owing to their multi-target advantages and low toxicity. In the current study, the effects of XK-81, a novel bromophenol compound extracted from Leathesia nana, on breast cancer, and its underlying mechanisms, were explored. Firstly, data from in vitro experiments indicated that 4T-1, one of common mouse breast cancer cell lines, was a XK-81-susceptible cell line, and ferroptosis was the major death manner in response to XK-81 treatment, which was evidenced by increasing intracellular Fe²⁺ and ROS level with condensed mitochondrial membrane densities, as well as decreasing the protein expressions of SLC7A11 and GPX4. In vivo, XK-81 suppressed the growth of 4T-1 breast-tumor in both BALB/C mice and zebrafish. Obviously, XK-81 decreased the protein expression of SLC7A11 and GPX4 in tumor tissues, hinting at the occurrence of ferroptosis. Moreover, XK-81 increased CD8+ T cells and NK cells numbers and regulated M1/M2 macrophage ratio in tumor tissues, indicating XK-81’s immunotherapeutic effect. Additionally, the secretions of immune-related cytokines, including TNF-α, IL-1β, and IL-12, were elevated with XK-81 stimulation in RAW 264.7 cells. Intriguingly, compared with doxorubicin-induced heart damage, XK-81 demonstrated the therapeutic advantage of little cardiotoxicity on the heart. XK-81 demonstrated potential antitumor advantage by both directly inducing ferroptosis-mediated death of tumor cells and immunization. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 3024 KiB

Open AccessArticle

Potency of Xanthone Derivatives from Garcinia mangostana L. for COVID-19 Treatment through Angiotensin-Converting Enzyme 2 and Main Protease Blockade: A Computational Study

by Cecep Suhandi, Siti Sarah Alfathonah and Aliya Nur Hasanah

Molecules 2023, 28(13), 5187; https://doi.org/10.3390/molecules28135187 - 4 Jul 2023

Cited by 11 | Viewed by 1885

Abstract

ACE2 and Mpro in the pathology of SARS-CoV-2 show great potential in developing COVID-19 drugs as therapeutic targets, due to their roles as the “gate” of viral entry and viral reproduction. Of the many potential compounds for ACE2 and Mpro inhibition, α-mangostin is [...] Read more.

ACE2 and Mpro in the pathology of SARS-CoV-2 show great potential in developing COVID-19 drugs as therapeutic targets, due to their roles as the “gate” of viral entry and viral reproduction. Of the many potential compounds for ACE2 and Mpro inhibition, α-mangostin is a promising candidate. Unfortunately, the potential of α-mangostin as a secondary metabolite with the anti-SARS-CoV-2 activity is hindered due to its low solubility in water. Other xanthone isolates, which also possess the xanthone core structure like α-mangostin, are predicted to be potential alternatives to α-mangostin in COVID-19 treatment, addressing the low drug-likeness of α-mangostin. This study aims to assess the potential of xanthone derivative compounds in the pericarp of mangosteen (Garcinia mangostana L.) through computational study. The study was conducted through screening activity using molecular docking study, drug-likeness prediction using Lipinski’s rule of five filtration, pharmacokinetic and toxicity prediction to evaluate the safety profile, and molecular dynamic study to evaluate the stability of formed interactions. The research results showed that there were 11 compounds with high potential to inhibit ACE2 and 12 compounds to inhibit Mpro. However, only garcinone B, in addition to being indicated as active, also possesses a drug-likeness, pharmacokinetic, and toxicity profile that was suitable. The molecular dynamic study exhibited proper stability interaction between garcinone B with ACE2 and Mpro. Therefore, garcinone B, as a xanthone derivative isolate compound, has promising potential for further study as a COVID-19 treatment as an ACE2 and Mpro inhibitor. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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13 pages, 3777 KiB

Open AccessArticle

Study of Salidroside and Its Inflammation Targeting Emulsion Gel for Wound Repair

by Xiaojie Wang, Jun Yang, Shuai Luo, Hucheng Zhang, Bo Liu and Zhiquan Pan

Molecules 2023, 28(13), 5151; https://doi.org/10.3390/molecules28135151 - 30 Jun 2023

Cited by 2 | Viewed by 1474

Abstract

Salidroside has been widely used in anti-tumor, cardiovascular, and cerebrovascular protection. However, there are few reports of its use for wound repair. Herein, salidroside inflammation-targeted emulsion gel and non-targeted emulsion gel were developed for wound repair. The inflammation-targeted emulsion gels showed an overall [...] Read more.

Salidroside has been widely used in anti-tumor, cardiovascular, and cerebrovascular protection. However, there are few reports of its use for wound repair. Herein, salidroside inflammation-targeted emulsion gel and non-targeted emulsion gel were developed for wound repair. The inflammation-targeted emulsion gels showed an overall trend of better transdermal penetration and lower potential than non-targeted emulsion gels (−58.7 mV and −1.6 mV, respectively). The apparent improvement of the trauma surface was significant in each administration group. There was a significant difference in the rate of wound healing of the rats between each administration group and the model group at days 7 and 14. Pathological tissue sections showed that inflammatory cells in the epidermis, dermis, and basal layer were significantly reduced, and the granulation tissue was proliferated in the inflammation-targeted emulsion gel group and the non-targeted emulsion gel group. Regarding the expressions of EGF and bFGF, the expressions of bFGF and EGF in the tissues of the inflammation-targeted group at days 7, 14, or 21 were significantly higher than that of the non-targeted emulsion gel group and the model group, both of which were statistically significant compared with the model group (p < 0.05). These results demonstrated that salidroside has the potential as an alternative drug for wound repair. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 4676 KiB

Open AccessArticle

Quercetin and Ferulic Acid Elicit Estrogenic Activities In Vivo and In Silico

by Meryem Slighoua, Fatima Ez-Zahra Amrati, Mohamed Chebaibi, Ismail Mahdi, Omkulthom Al Kamaly, Khadija El Ouahdani, Aziz Drioiche, Asmaa Saleh and Dalila Bousta

Molecules 2023, 28(13), 5112; https://doi.org/10.3390/molecules28135112 - 29 Jun 2023

Cited by 7 | Viewed by 2271

Abstract

In this study, we examined the sub-acute toxicity of quercetin and ferulic acid and evaluated their effects on protein, cholesterol, and estrogen levels in vivo. Six groups of female Wistar rats were fed by gavage. The first and second groups represent the positive [...] Read more.

In this study, we examined the sub-acute toxicity of quercetin and ferulic acid and evaluated their effects on protein, cholesterol, and estrogen levels in vivo. Six groups of female Wistar rats were fed by gavage. The first and second groups represent the positive (Clomiphene citrate 10 mg/kg) and negative (NaCl 0.9%) control groups, while the other groups received quercetin and ferulic acid at doses of 5 and 10 mg/kg/day for 28 days. The sub-acute toxicity was monitored by examining the weights, biochemical parameters (AST, ALT, ALP, urea, and CREA), and histological changes in the kidneys and liver of the treated animals. Furthermore, the in vivo estrogenic effects were studied in terms of the serum and ovarian cholesterol levels, serum estradiol, and uterine proteins. Finally, Docking studies were conducted to evaluate the binding affinity of quercetin and ferulic acid for alpha and beta estrogen receptors. Results showed that both compounds were devoid of any signs of nephrotoxicity or hepatotoxicity. Additionally, quercetin and ferulic acid caused significant estrogenic effects evidenced by an increase of 8.7 to 22.48% in serum estradiol, though to a lesser amount than in the reference drug-treated group (64.21%). Moreover, the two compounds decreased the serum cholesterol levels (12.26–32.75%) as well as the ovarian cholesterol level (11.9% to 41.50%) compared to the negative control. The molecular docking in estrogen alpha and estrogen beta active sites showed high affinity of quercetin (−10.444 kcal/mol for estrogen alpha and −10.662 kcal/mol for estrogen beta) and ferulic acid (−6.377 kcal/mol for estrogen alpha and −6.3 kcal/mol for estrogen beta) to these receptors. This study provides promising insights into the potential use of quercetin as a therapeutic agent for the management of female fertility issues. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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10 pages, 1200 KiB

Open AccessArticle

Enhancement of the Bioactive Compound Content and Antibacterial Activities in Curcuma Longa Using Zinc Oxide Nanoparticles

by Munirah F. Aldayel

Molecules 2023, 28(13), 4935; https://doi.org/10.3390/molecules28134935 - 23 Jun 2023

Cited by 2 | Viewed by 1518

Abstract

Incorporating nanoparticles into plant cultivation has been shown to improve growth parameters and alter the bioactive component compositions of many plant species, including Curcumin longa. The aim of the current study was to investigate the effects of foliar application of zinc oxide [...] Read more.

Incorporating nanoparticles into plant cultivation has been shown to improve growth parameters and alter the bioactive component compositions of many plant species, including Curcumin longa. The aim of the current study was to investigate the effects of foliar application of zinc oxide nanoparticles on the content of bioactive compounds and their antibacterial activities against potential bacterial pathogens. To this end, C. longa leaves were treated with different doses of ZnO NPs to see how this affected their bioactive component composition. The effect of different doses of ZnO NPs on the accumulation of bisdemethoxycurcumin, demethoxycurcumin, and curcumin in ethanolic extracts of C. longa rhizomes was evaluated using high-performance liquid chromatography (HPLC). When compared to the control treatment, foliar spraying with (5 and 40 mgL⁻¹) of ZnO NPs increased bisdemethoxycurcumin, demethoxycurcumin, and curcumin levels approximately (2.69 and 2.84)-, (2.61 and 3.22)-, and (2.90 and 3.45)-fold, respectively. We then checked whether the ethanolic extracts produced from the plantlets changed in terms of their phytochemical makeup and antibacterial properties. Furthermore, the results revealed that C. long-ZnO NPs displayed antibacterial activity against the tested S. aureus and P. aeruginosa bacterium strains, but had a few effect against E. coli. The MIC for P. aeruginosa was 100 g/mL. The time–kill studies also revealed that ZnO NPs at 4 MIC killed P. aeruginosa, Actinobacteria baumannii, and Bacillus sp. after 2 h, while S. aureus did not grow when treated with 4 × MIC of the extract for 6 h. The strongest antibacterial activity was seen in the extract from plantlets grown without nanoparticles for P. aeruginosa, whereas it was seen in the extract from plantlets grown in the presence of 5 mg/L ZnO NPs for E. coli, S. aureus, and P. aeruginosa. These findings show that ZnO NPs are powerful enhancers of bioactive compound production in C. longa, a trait that can be used to combat antibiotic resistance in pathogenic bacterial species. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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21 pages, 1244 KiB

Open AccessArticle

Phytochemical Composition and Antioxidant Activity of Various Extracts of Fibre Hemp (Cannabis sativa L.) Cultivated in Lithuania

by Asta Judžentienė, Rasa Garjonytė and Jurga Būdienė

Molecules 2023, 28(13), 4928; https://doi.org/10.3390/molecules28134928 - 22 Jun 2023

Cited by 11 | Viewed by 4182

Abstract

The phytochemistry of fibre hemp (Cannabis sativa L., cv. Futura 75 and Felina 32) cultivated in Lithuania was investigated. The soil characteristics (conductivity, pH and major elements) of the cultivation field were determined. The chemical composition of hemp extracts and essential oils [...] Read more.

The phytochemistry of fibre hemp (Cannabis sativa L., cv. Futura 75 and Felina 32) cultivated in Lithuania was investigated. The soil characteristics (conductivity, pH and major elements) of the cultivation field were determined. The chemical composition of hemp extracts and essential oils (EOs) from different plant parts was determined by the HPLC/DAD/TOF and GC/MS techniques. Among the major constituents, β-caryophyllene (≤46.64%) and its oxide (≤14.53%), α-pinene (≤20.25%) or α-humulene (≤11.48) were determined in EOs. Cannabidiol (CBD) was a predominant compound (≤64.56%) among the volatile constituents of the methanolic extracts of hemp leaves and inflorescences. Appreciable quantities of 2-monolinolein (11.31%), methyl eicosatetraenoate (9.70%) and γ-sitosterol (8.99%) were detected in hemp seed extracts. The octadecenyl ester of hexadecenoic acid (≤31.27%), friedelan-3-one (≤21.49%), dihydrobenzofuran (≤17.07%) and γ-sitosterol (14.03%) were major constituents of the methanolic extracts of hemp roots, collected during various growth stages. The CBD quantity was the highest in hemp flower extracts in pentane (32.73%). The amounts of cannabidiolic acid (CBDA) were up to 24.21% in hemp leaf extracts. The total content of tetrahydrocannabinol (THC) isomers was the highest in hemp flower pentane extracts (≤22.43%). The total phenolic content (TPC) varied from 187.9 to 924.7 (average means, mg/L of gallic acid equivalent (GAE)) in aqueous unshelled hemp seed and flower extracts, respectively. The TPC was determined to be up to 321.0 (mg/L GAE) in root extracts. The antioxidant activity (AA) of hemp extracts and Eos was tested by the spectrophotometric DPPH^● scavenging activity method. The highest AA was recorded for hemp leaf EOs (from 15.034 to 35.036 mmol/L, TROLOX equivalent). In the case of roots, the highest AA (1.556 mmol/L, TROLOX) was found in the extracts of roots collected at the seed maturation stage. The electrochemical (cyclic and square wave voltammetry) assays correlated with the TPC. The hydrogen-peroxide-scavenging activity of extracts was independent of the TPC. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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26 pages, 4441 KiB

Open AccessArticle

Novel Oleanolic Acid-Phtalimidines Tethered 1,2,3 Triazole Hybrids as Promising Antibacterial Agents: Design, Synthesis, In Vitro Experiments and In Silico Docking Studies

by Ghofrane Lahmadi, Mabrouk Horchani, Amal Dbeibia, Abdelkarim Mahdhi, Anis Romdhane, Ata Martin Lawson, Adam Daïch, Abdel Halim Harrath, Hichem Ben Jannet and Mohamed Othman

Molecules 2023, 28(12), 4655; https://doi.org/10.3390/molecules28124655 - 8 Jun 2023

Cited by 5 | Viewed by 1844

Abstract

As part of the valorization of agricultural waste into bioactive compounds, a series of structurally novel oleanolic acid ((3β-hydroxyolean-12-en-28-oic acid, OA-1)-phtalimidines (isoindolinones) conjugates 18a–u bearing 1,2,3-triazole moieties were designed and synthesized by treating an azide 4 previously prepared from OA-1 [...] Read more.

As part of the valorization of agricultural waste into bioactive compounds, a series of structurally novel oleanolic acid ((3β-hydroxyolean-12-en-28-oic acid, OA-1)-phtalimidines (isoindolinones) conjugates 18a–u bearing 1,2,3-triazole moieties were designed and synthesized by treating an azide 4 previously prepared from OA-1 isolated from olive pomace (Olea europaea L.) with a wide range of propargylated phtalimidines using the Cu(I)-catalyzed click chemistry approach. OA-1 and its newly prepared analogues, 18a–u, were screened in vitro for their antibacterial activity against two Gram-positive bacteria, Staphylococcus aureus and Listeria monocytogenes, and two Gram-negative bacteria, Salmonella thyphimurium and Pseudomonas aeruginosa. Attractive results were obtained, notably against L. monocytogenes. Compounds 18d, 18g, and 18h exhibited the highest antibacterial activity when compared with OA-1 and other compounds in the series against tested pathogenic bacterial strains. A molecular docking study was performed to explore the binding mode of the most active derivatives into the active site of the ABC substrate-binding protein Lmo0181 from L. monocytogenes. Results showed the importance of both hydrogen bonding and hydrophobic interactions with the target protein and are in favor of the experimental data. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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27 pages, 6449 KiB

Open AccessArticle

Pro-Apoptotic Activity and Cell Cycle Arrest of Caulerpa sertularioides against SKLU-1 Cancer Cell in 2D and 3D Cultures

by Rosette Agena, Alejandro De Jesús Cortés-Sánchez, Humberto Hernández-Sánchez, Luis Marat Álvarez-Salas, Oswaldo Pablo Martínez-Rodríguez, Víctor Hugo Rosales García and María Eugenia Jaramillo Flores

Molecules 2023, 28(11), 4361; https://doi.org/10.3390/molecules28114361 - 26 May 2023

Cited by 1 | Viewed by 2144

Abstract

Cancer is a disease with the highest mortality and morbidity rate worldwide. First-line drugs induce several side effects that drastically reduce the quality of life of people with this disease. Finding molecules to prevent it or generate less aggressiveness or no side effects [...] Read more.

Cancer is a disease with the highest mortality and morbidity rate worldwide. First-line drugs induce several side effects that drastically reduce the quality of life of people with this disease. Finding molecules to prevent it or generate less aggressiveness or no side effects is significant to counteract this problem. Therefore, this work searched for bioactive compounds of marine macroalgae as an alternative treatment. An 80% ethanol extract of dried Caulerpa sertularioides (CSE) was analyzed by HPLS-MS to identify the chemical components. CSE was utilized through a comparative 2D versus 3D culture model. Cisplatin (Cis) was used as a standard drug. The effects on cell viability, apoptosis, cell cycle, and tumor invasion were evaluated. The IC₅₀ of CSE for the 2D model was 80.28 μg/mL versus 530 μg/mL for the 3D model after 24 h of treatment exposure. These results confirmed that the 3D model is more resistant to treatments and complex than the 2D model. CSE generated a loss of mitochondrial membrane potential, induced apoptosis by extrinsic and intrinsic pathways, upregulated caspases-3 and -7, and significantly decreased tumor invasion of a 3D SKLU-1 lung adenocarcinoma cell line. CSE generates biochemical and morphological changes in the plasma membrane and causes cell cycle arrest at the S and G2/M phases. These findings conclude that C. sertularioides is a potential candidate for alternative treatment against lung cancer. This work reinforced the use of complex models for drug screening and suggested using CSE’s primary component, caulerpin, to determine its effect and mechanism of action on SKLU-1 in the future. A multi-approach with molecular and histological analysis and combination with first-line drugs must be included. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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18 pages, 6663 KiB

Open AccessArticle

UPLC-QE-Orbitrap-Based Cell Metabolomics and Network Pharmacology to Reveal the Mechanism of N-Benzylhexadecanamide Isolated from Maca (Lepidium meyenii Walp.) against Testicular Dysfunction

by Kai-Yue Zhang, Chun-Nan Li, Nan-Xi Zhang, Xiao-Chen Gao, Jia-Ming Shen, Duan-Duan Cheng, Yue-Long Wang, Hui Zhang, Jing-Wei Lv and Jia-Ming Sun

Molecules 2023, 28(10), 4064; https://doi.org/10.3390/molecules28104064 - 12 May 2023

Cited by 8 | Viewed by 1889

Abstract

Testicular dysfunction (TDF) is characterized by testosterone deficiency and is caused by oxidative stress injury in Leydig cells. A natural fatty amide named N-benzylhexadecanamide (NBH), derived from cruciferous maca, has been shown to promote testosterone production. Our study aims to reveal the anti-TDF [...] Read more.

Testicular dysfunction (TDF) is characterized by testosterone deficiency and is caused by oxidative stress injury in Leydig cells. A natural fatty amide named N-benzylhexadecanamide (NBH), derived from cruciferous maca, has been shown to promote testosterone production. Our study aims to reveal the anti-TDF effect of NBH and explore its potential mechanism in vitro. This study examined the effects of H₂O₂ on cell viability and testosterone levels in mouse Leydig cells (TM3) under oxidative stress. In addition, cell metabolomics analysis based on UPLC-Q-Exactive-MS/MS showed that NBH was mainly involved in arginine biosynthesis, aminoacyl-tRNA biosynthesis, phenylalanine, tyrosine and tryptophan biosynthesis, the TCA cycle and other metabolic pathways by affecting 23 differential metabolites, including arginine and phenylalanine. Furthermore, we also performed network pharmacological analysis to observe the key protein targets in NBH treatment. The results showed that its role was to up-regulate ALOX5, down-regulate CYP1A2, and play a role in promoting testicular activity by participating in the steroid hormone biosynthesis pathway. In summary, our study not only provides new insights into the biochemical mechanisms of natural compounds in the treatment of TDF, but also provides a research strategy that integrates cell metabolomics and network pharmacology in order to promote the screening of new drugs for the treatment of TDF. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 685 KiB

Open AccessArticle

Seven New Phenylhexanoids with Antioxidant Activity from Saxifraga umbellulata var. pectinata

by Jiao Huang, Donglin Chen, Mengying Liu, Yarui Yu, Yi Zhang and Jing Huang

Molecules 2023, 28(9), 3928; https://doi.org/10.3390/molecules28093928 - 6 May 2023

Cited by 1 | Viewed by 1182

Abstract

Seven new phenylhexanoids, (S)-(+)-3,4-dihydroxy-11-methoxyphenylhex-9-one (1), (E) 3,4-dihydroxy-phenylhex-10-en-9-one (2), (E)-4-hydroxyphenylhex-10-en-9-one (3), (R)-(−)-3,4,11-trihydroxyphenylhex-9-one 11-O-β-d-glucopyranoside (4), (R)-(−)-4,11-dihydroxyphenylhex-9-one 11-O-β- [...] Read more.

Seven new phenylhexanoids, (S)-(+)-3,4-dihydroxy-11-methoxyphenylhex-9-one (1), (E) 3,4-dihydroxy-phenylhex-10-en-9-one (2), (E)-4-hydroxyphenylhex-10-en-9-one (3), (R)-(−)-3,4,11-trihydroxyphenylhex-9-one 11-O-β-d-glucopyranoside (4), (R)-(−)-4,11-dihydroxyphenylhex-9-one 11-O-β-d-glucopyranoside (5), phenylhex-4,9,11-triol 11-O-β-d-glucopyranoside (6), and 9-O-acetyl-phenylhex-4,9,11-triol 11-O-β-d-glucopyranoside (7), were isolated and identified from Tibetan medicine Saxifraga umbellulata var. pectinate. The antioxidant activities of these compounds were evaluated using the DPPH and ABTS radical scavenging experiments. In the ABTS experiment, compounds 1 (IC₅₀ 13.99 ± 2.53 μM) and 2 (IC₅₀ 13.11 ± 0.94 μM) exhibited significantly better antioxidant activity than L-ascorbic acid (IC₅₀ 23.51 ± 0.44 μM). Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 2527 KiB

Open AccessArticle

Protocatechuic Acid Alleviates Dextran-Sulfate-Sodium-Induced Ulcerative Colitis in Mice via the Regulation of Intestinal Flora and Ferroptosis

by Xuebin Yang, Xin Sun, Feng Zhou, Shuiping Xiao, Lulu Zhong, Shian Hu, Zhe Zhou, Ling Li and Yang Tan

Molecules 2023, 28(9), 3775; https://doi.org/10.3390/molecules28093775 - 27 Apr 2023

Cited by 18 | Viewed by 2284

Abstract

Protocatechuic acid (PCA) is a natural component with multiple biological activities. However, the underlying mechanisms of the effects of PCA on anti-ulcerative colitis (UC) are unclear. A UC mouse model was established by allowing the mice to freely drink a dextran sulfate sodium [...] Read more.

Protocatechuic acid (PCA) is a natural component with multiple biological activities. However, the underlying mechanisms of the effects of PCA on anti-ulcerative colitis (UC) are unclear. A UC mouse model was established by allowing the mice to freely drink a dextran sulfate sodium solution. The mice were administered PCA intragastrically for 7 days. Histological pathology, intestinal flora, and ferroptosis regulators were determined in vivo. Additionally, ferroptotic Caco-2 cells were modeled to investigate the role of PCA in ferroptosis. Our results showed that PCA reduced the levels of the disease activity index, inflammatory factors, and histological damage in UC mice. We also found that the regulation of intestinal flora, especially Bacteroidetes, was one of the potential mechanisms underlying the protective effects of PCA anti-UC. Moreover, PCA downregulated the level of ferroptosis in the colon tissue, as evidenced by a reduced iron overload, decreased glutathione depletion, and a lower level of malondialdehyde production compared with the model group. Similar effects of PCA on ferroptosis were observed in Erastin-treated Caco-2 cells. The results obtained using reactive oxygen species assays and the changes in mitochondrial structure observed via scanning electron microscopy also support these results. Our findings suggested that PCA protected against UC by regulating intestinal flora and ferroptosis. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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10 pages, 951 KiB

Open AccessArticle

The Mosquito Larvicidal Activity of Lignans from Branches of Cinnamomum camphora chvar. Borneol

by Zhiyong Xu, Junhui Chen, Ruifeng Shang, Fan Yang, Chuanqi Xie, Yunfei Liu, Xuefang Wen, Jianping Fu, Wei Xiong and Lei Wu

Molecules 2023, 28(9), 3769; https://doi.org/10.3390/molecules28093769 - 27 Apr 2023

Cited by 3 | Viewed by 1620

Abstract

The chemical investigation of branches of Cinnamomum camphora chvar. Borneol guided by mosquito larvicidal activity led to the isolation of fourteen known lignans (1–14). Their structures were elucidated unambiguously based on comprehensive spectroscopic analysis and comparison with the literature [...] Read more.

The chemical investigation of branches of Cinnamomum camphora chvar. Borneol guided by mosquito larvicidal activity led to the isolation of fourteen known lignans (1–14). Their structures were elucidated unambiguously based on comprehensive spectroscopic analysis and comparison with the literature data. This is the first report of these compounds being isolated from branches of Cinnamomum camphora chvar. Borneol. Compounds 3–5 and 8–14 were isolated from this plant for the first time. All compounds isolated were subjected to anti-inflammatory, mosquito larvicidal activity and cytotoxic activity evaluation. Compounds (1–14) showed significant mosquito larvicidal activity against Culex pipiens quinquefasciatus with lethal mortality in 50% (LC₅₀), with values ranging from 0.009 to 0.24 μg/mL. Among them, furofuran lignans(1–8) exhibited potent mosquito larvicidal activity against Cx. p. quinquefasciatus, with LC₅₀ values of 0.009–0.021 μg/mL. From the perspective of a structure–activity relationship, compounds with a dioxolane group showed high mosquito larvicidal activity and have potential to be developed into a mosquitocide. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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18 pages, 2394 KiB

Open AccessArticle

Horse Chestnut Saponins–Escins, Isoescins, Transescins, and Desacylescins

by Philippe Savarino, Emmanuel Colson, Julien André and Pascal Gerbaux

Molecules 2023, 28(5), 2087; https://doi.org/10.3390/molecules28052087 - 23 Feb 2023

Cited by 2 | Viewed by 2721

Abstract

Escins constitute an abundant family of saponins (saponosides) and are the most active components in Aesculum hippocastanum (horse chestnut—HC) seeds. They are of great pharmaceutical interest as a short-term treatment for venous insufficiency. Numerous escin congeners (slightly different compositions), as well as numerous [...] Read more.

Escins constitute an abundant family of saponins (saponosides) and are the most active components in Aesculum hippocastanum (horse chestnut—HC) seeds. They are of great pharmaceutical interest as a short-term treatment for venous insufficiency. Numerous escin congeners (slightly different compositions), as well as numerous regio-and stereo-isomers, are extractable from HC seeds, making quality control trials mandatory, especially since the structure–activity relationship (SAR) of the escin molecules remains poorly described. In the present study, mass spectrometry, microwave activation, and hemolytic activity assays were used to characterize escin extracts (including a complete quantitative description of the escin congeners and isomers), modify the natural saponins (hydrolysis and transesterification) and measure their cytotoxicity (natural vs. modified escins). The aglycone ester groups characterizing the escin isomers were targeted. A complete quantitative analysis, isomer per isomer, of the weight content in the saponin extracts as well as in the seed dry powder is reported for the first time. An impressive 13% in weight of escins in the dry seeds was measured, confirming that the HC escins must be absolutely considered for high-added value applications, provided that their SAR is established. One of the objectives of this study was to contribute to this development by demonstrating that the aglycone ester functions are mandatory for the toxicity of the escin derivative, and that the cytotoxicity also depends on the relative position of the ester functions on the aglycone. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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14 pages, 2645 KiB

Open AccessArticle

Two Ferulic Acid Derivatives Inhibit Neuroinflammatory Response in Human HMC3 Microglial Cells via NF-κB Signaling Pathway

by Pei-Lin Li, Xiao-Xue Zhai, Jun Wang, Xiang Zhu, Lin Zhao, Shuang You, Chun-Yan Sang and Jun-Li Yang

Molecules 2023, 28(5), 2080; https://doi.org/10.3390/molecules28052080 - 22 Feb 2023

Cited by 5 | Viewed by 2370

Abstract

Various physiological and pathological changes are related to the occurrence and development of neurodegenerative diseases. Neuroinflammation is a major trigger and exacerbation of neurodegenerative diseases. One of the main symptoms of neuritis is the activation of microglia. Thus, to alleviate the occurrence of [...] Read more.

Various physiological and pathological changes are related to the occurrence and development of neurodegenerative diseases. Neuroinflammation is a major trigger and exacerbation of neurodegenerative diseases. One of the main symptoms of neuritis is the activation of microglia. Thus, to alleviate the occurrence of neuroinflammatory diseases, an important method is to inhibit the abnormal activation of microglia. This research evaluated the inhibitory effect of trans-ferulic acid (TJZ-1) and methyl ferulate (TJZ-2), isolated from Zanthoxylum armatum, on neuroinflammation, by establishing the human HMC3 microglial cell neuroinflammation model induced by lipopolysaccharide (LPS). The results showed both compounds significantly inhibited the production and expression of nitric oxide (NO), tumor necrosis factor-α (TNF-α), and interleukin-1β (IL-1β) contents, and increased the level of anti-inflammatory factor β-endorphin (β-EP). Furthermore, TJZ-1 and TJZ-2 can inhibit LPS-induced activation of nuclear factor kappa B (NF-κB). It was found that of two ferulic acid derivatives, both had anti-neuroinflammatory effects by inhibiting the NF-κB signaling pathway and regulating the release of inflammatory mediators, such as NO, TNF-α, IL-1β, and β-EP. This is the first report that demonstrates that TJZ-1 and TJZ-2 had inhibitory effects on LPS-induced neuroinflammation in human HMC3 microglial cells, which indicates that two ferulic acid derivates from Z. armatum could be used as potential anti-neuroinflammatory agents. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 6159 KiB

Open AccessArticle

Antibacterial Activity and Mechanism of Madecassic Acid against Staphylococcus aureus

by Chunling Wei, Peiwu Cui and Xiangqian Liu

Molecules 2023, 28(4), 1895; https://doi.org/10.3390/molecules28041895 - 16 Feb 2023

Cited by 15 | Viewed by 3274

Abstract

Antibacterial resistance has become one of the most serious problems threating global health. To overcome this urgent problem, many scientists have paid great attention to developing new antibacterial drugs from natural products. Hence, for exploring new antibacterial drugs from Chinese medicine, a series [...] Read more.

Antibacterial resistance has become one of the most serious problems threating global health. To overcome this urgent problem, many scientists have paid great attention to developing new antibacterial drugs from natural products. Hence, for exploring new antibacterial drugs from Chinese medicine, a series of experiments were carried out for verifying and elucidating the antibacterial activity and mechanisms of madecassic acid (MA), which is an active triterpenoid compound isolated from the traditional Chinese medicine, Centella asiatica. The antibacterial activity was investigated through measuring the diameter of the inhibition zone, the minimum inhibitory concentration (MIC), the growth curve, and the effect on the bacterial biofilm, respectively. Meanwhile, the antibacterial mechanism was also discussed from the aspects of cell wall integrity variation, cell membrane permeability, and the activities of related enzymes in the respiratory metabolic pathway before and after the intervention by MA. The results showed that MA had an inhibitory effect on eight kinds of pathogenic bacteria, and the MIC values for Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis, and Bacillus megaterium were 31.25, 62.5, 250, 125, 62.5, and 62.5 µg/mL, respectively. For instance, 31.25 µg/mL MA could inhibit the growth of Staphylococcus aureus within 28 h. The antibacterial mechanism experiments confirmed that MA could destroy the integrity of the cell membrane and cell wall of Staphylococcus aureus, causing the leakage of macromolecular substances, inhibiting the synthesis of soluble proteins, reducing the activities of succinate dehydrogenase and malate dehydrogenase, and interacting with DNA, leading to the relaxation and ring opening of supercoiled DNA. Besides, the activities of DNA topoisomerase I and II were both inhibited by MA, which led to the cell growth of Staphylococcus aureus being repressed. This study provides a theoretical basis and reference for the application of MA in the control and inhibition of food-borne Staphylococcus aureus. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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10 pages, 1488 KiB

Open AccessFeature PaperArticle

Isolation and Bioassay of a New Terminalone A from Terminalia arjuna

by Bushra, Khalil ur Rehman, Dilfaraz Khan, Abdulrahman A. Almehizia, Ahmed M. Naglah, Asma S. Al-Wasidi, Moamen S. Refat, Mohamed Y. El-Sayed, Hamid Ullah and Shafiullah Khan

Molecules 2023, 28(3), 1015; https://doi.org/10.3390/molecules28031015 - 19 Jan 2023

Cited by 1 | Viewed by 1931

Abstract

Terminalia arjuna possesses significant cardioprotective, antidiabetic and antioxidant properties as these properties are described in Ayurveda. In the present study, three flavonoids were isolated through the separation and chromatographic purification of the whole plant material of T. arjuna. Spectroscopic characterization identified one [...] Read more.

Terminalia arjuna possesses significant cardioprotective, antidiabetic and antioxidant properties as these properties are described in Ayurveda. In the present study, three flavonoids were isolated through the separation and chromatographic purification of the whole plant material of T. arjuna. Spectroscopic characterization identified one of them as a new flavonoid “Terminalone A (1)” and two known flavonoids i.e., 6-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one (2) and 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one (3). The bioactivity studies showed considerable antibacterial and antioxidant (DPPH radical scavenging) potential for all the three compounds 1–3 where the compound 1 showed strong antibacterial and antioxidant activity. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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22 pages, 4742 KiB

Open AccessArticle

Biological Properties, Phenolic Profile, and Botanical Aspect of Nigella sativa L. and Nigella damascena L. Seeds: A Comparative Study

by Leila Benazzouz-Smail, Sabiha Achat, Fatiha Brahmi, Mostapha Bachir-Bey, Radia Arab, José Manuel Lorenzo, Aicha Benbouriche, Kahina Boudiab, Didier Hauchard, Lila Boulekbache and Khodir Madani

Molecules 2023, 28(2), 571; https://doi.org/10.3390/molecules28020571 - 6 Jan 2023

Cited by 15 | Viewed by 6656

Abstract

The use of Nigella seeds in the food, pharmaceutical, and cosmetic fields is common, since the iniquity and the virtues of these plants are directly related to their characteristic phytochemical composition. This investigation focused on the comparative study of the botanical aspect, phenolic [...] Read more.

The use of Nigella seeds in the food, pharmaceutical, and cosmetic fields is common, since the iniquity and the virtues of these plants are directly related to their characteristic phytochemical composition. This investigation focused on the comparative study of the botanical aspect, phenolic profile, and in vitro and in vivo biological activities of Nigella sativa L. (NS) and Nigella damascena L. (ND) seeds. The macro- and micro-morphological properties of these seeds were studied, and the key dissimilarities between them were clearly illustrated. The phytochemical contents and phenolic profiles were determined, and the in vitro antioxidant activity was assessed using four methods. The in vivo antioxidant and biochemical parameters of the blood of supplemented mice were determined. The results of the macro- and micro-structure analysis revealed differences between the two plants. Here, ND is characterized by higher phytochemical contents and the best antioxidant activities. The HPLC analysis indicated the presence of nine compounds, namely seven phenolic acids, particularly hydroxybenzoic and caffeic acids, and two flavonoids. The administration of ND extract to mice for 21 days at a concentration of 500 mg/kg allowed a substantial amelioration of plasma antioxidant properties. In addition, the extracts ameliorate blood parameters (cholesterol, triglycerides, glycemia, and urea). Furthermore, the antimicrobial activity of extracts demonstrated their effects on Staphylococcus and Aspergillus. Nigella seeds, in particular ND, expressed considerable in vitro antioxidant properties and demonstrated significant amelioration of mice blood properties. Consequently, these species can serve as a valuable source of compounds with various applications. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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14 pages, 1622 KiB

Open AccessArticle

UPLC-MS-ESI-QTOF Analysis and Antifungal Activity of Aqueous Extracts of Spondias tuberosa

by Antonia Thassya Lucas dos Santos, Joara Nályda Pereira Carneiro, Rafael Pereira da Cruz, Débora Lima Sales, Jacqueline Cosmo Andrade-Pinheiro, Maria Audilene de Freitas, Marta Regina Kerntopf, Gyllyandeson de Araújo Delmondes, Paulo Riceli Vasconcelos Ribeiro, Edy Sousa de Brito, Francisco Lucas Alves Batista, Francisco Ernani Alves Magalhães, Ivo C. Pita Neto, Maria Flaviana Bezerra Morais-Braga, Radosław Kowalski, Grazyna Kowalska, Aleksandra Szopa, Tomasz Baj and Henrique Douglas Melo Coutinho

Molecules 2023, 28(1), 305; https://doi.org/10.3390/molecules28010305 - 30 Dec 2022

Cited by 2 | Viewed by 2592

Abstract

This study aimed to identify the chemical composition of the Spondias tuberosa aqueous leaf and root extracts (EALST and EARST) and to evaluate their effect, comparatively, against opportunistic pathogenic fungi. Ultra-Performance Liquid Chromatography Coupled to a Quadrupole/Time of Flight System (UPLC-MS-ESI-QTOF) was employed [...] Read more.

This study aimed to identify the chemical composition of the Spondias tuberosa aqueous leaf and root extracts (EALST and EARST) and to evaluate their effect, comparatively, against opportunistic pathogenic fungi. Ultra-Performance Liquid Chromatography Coupled to a Quadrupole/Time of Flight System (UPLC-MS-ESI-QTOF) was employed for chemical analysis. Candida albicans and C. tropicalis standard strains and clinical isolates were used (CA INCQS 40006, CT INCQS 40042, CA URM 5974, and CT URM 4262). The 50% Inhibitory Concentration for the fungal population (IC₅₀) was determined for both the intrinsic action of the extracts and the extract/fluconazole (FCZ) associations. The determination of the Minimum Fungicidal Concentration (MFC) and the verification of effects over fungal morphological transitions were performed by subculture in Petri dishes and humid chambers, respectively, both based on micro-dilution. UPLC-MS-ESI-QTOF analysis revealed the presence of phenolic and flavonoid compounds. The association of the extracts with fluconazole, resulted in IC₅₀ values from 2.62 µg/mL to 308.96 µg/mL. The MFC of the extracts was ≥16,384 µg/mL for all tested strains, while fluconazole obtained an MFC of 8192 µg/mL against C. albicans strains. A reduction in MFC against CA URM 5974 (EALST: 2048 µg/mL and EARST: 1024 µg/mL) occurred in the extract/fluconazole association. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 1575 KiB

Open AccessArticle

Antifungal Effect and Inhibition of the Virulence Mechanism of D-Limonene against Candida parapsilosis

by Melyna Chaves Leite-Andrade, Luiz Nascimento de Araújo Neto, Maria Daniela Silva Buonafina-Paz, Franz de Assis Graciano dos Santos, Adryelle Idalina da Silva Alves, Maria Carolina Accioly Brelaz de Castro, Edna Mori, Bruna Caroline Gonçalves Vasconcelos de Lacerda, Isaac Moura Araújo, Henrique Douglas Melo Coutinho, Grażyna Kowalska, Radosław Kowalski, Tomasz Baj and Rejane Pereira Neves

Molecules 2022, 27(24), 8884; https://doi.org/10.3390/molecules27248884 - 14 Dec 2022

Cited by 10 | Viewed by 2394

Abstract

Yeasts from the Candida parapsilosis complex are clinically relevant due to their high virulence and pathogenicity potential, such as adherence to epithelial cells and emission of filamentous structures, as well as their low susceptibility to antifungals. D-limonene, a natural compound, emerges as a [...] Read more.

Yeasts from the Candida parapsilosis complex are clinically relevant due to their high virulence and pathogenicity potential, such as adherence to epithelial cells and emission of filamentous structures, as well as their low susceptibility to antifungals. D-limonene, a natural compound, emerges as a promising alternative with previously described antibacterial, antiparasitic, and antifungal activity; however, its mechanisms of action and antivirulence activity against C. parapsilosis complex species have not been elucidated. Therefore, in the present study, we aimed to evaluate the antifungal and antivirulence action, as well as the mechanism of action of D-limonene against isolates from this complex. D-limonene exhibited relevant antifungal activity against C. parapsilosis complex yeasts, as well as excellent antivirulence activity by inhibiting yeast morphogenesis and adherence to the human epithelium. Furthermore, the apoptotic mechanism induced by this compound, which is not induced by oxidative stress, represents an important target for the development of new antifungal drugs. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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7 pages, 1318 KiB

Open AccessArticle

Asperphenyltones A and B: New Phenylfuropyridinone Skeleton from an Endophytic Aspergillus sp. GXNU-A1

by Jiguo Huang, Xianglong Bo, Furong Wu, Meijing Tan, Youquan Wei, Lixia Wang, Junqiang Zhou, Guiming Wu and Xishan Huang

Molecules 2022, 27(23), 8160; https://doi.org/10.3390/molecules27238160 - 23 Nov 2022

Cited by 3 | Viewed by 1573

Abstract

Chemical investigation of the fermentation extract of the mangrove endophytic fungus Aspergillus sp. GXNU-A1, isolated from Acanthus ilicifolius L., discovered an undescribed pair of enantiomers (asperphenyltones A and B (±1)), together with four previously described metabolites: nodulisporol (2), isosclerone [...] Read more.

Chemical investigation of the fermentation extract of the mangrove endophytic fungus Aspergillus sp. GXNU-A1, isolated from Acanthus ilicifolius L., discovered an undescribed pair of enantiomers (asperphenyltones A and B (±1)), together with four previously described metabolites: nodulisporol (2), isosclerone (3), 2,3,4-trihydroxy-6-(hydroxymethyl)-5-methylbenzyl alcohol (4), and 4,6-dihydroxy-5-methoxy-7-methyl-1,3-dihydroisobenzofuran (5). Analyses of the 1D and 2D NMR spectroscopic data of the compounds supported their structural assignments. The presence of the asperphenyltones A and B, which are a pair of enantiomers, was established by HR-ESI-MS, 1D and 2D NMR data and confirmed by single-crystal X-ray diffraction analysis. Metabolites 1–5 were evaluated for their anti-inflammatory effects on the production of nitric oxide (NO), and 1, 3, and 4 showed significant potential inhibitory activities against NO production in activated macrophages with IC₅₀ values of 26–40 μM, respectively. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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20 pages, 2228 KiB

Open AccessArticle

Beyond Traditional Use of Alchemilla vulgaris: Genoprotective and Antitumor Activity In Vitro

by Sanja Jelača, Zora Dajić-Stevanović, Nenad Vuković, Stefan Kolašinac, Antoaneta Trendafilova, Paraskev Nedialkov, Miroslava Stanković, Nasta Tanić, Nikola T. Tanić, Aleksandar Acović, Sanja Mijatović and Danijela Maksimović-Ivanić

Molecules 2022, 27(23), 8113; https://doi.org/10.3390/molecules27238113 - 22 Nov 2022

Cited by 9 | Viewed by 2772

Abstract

Alchemilla vulgaris L. (lady’s mantle) was used for centuries in Europe and Balkan countries for treatments of numerous conditions and diseases of the reproductive system, yet some of the biological activities of lady’s mantle have been poorly studied and neglected. The present study [...] Read more.

Alchemilla vulgaris L. (lady’s mantle) was used for centuries in Europe and Balkan countries for treatments of numerous conditions and diseases of the reproductive system, yet some of the biological activities of lady’s mantle have been poorly studied and neglected. The present study aimed to estimate the potential of A. vulgaris ethanolic extract from Southeast Serbia to prevent and suppress tumor development in vitro, validated by antioxidant, genoprotective, and cytotoxic properties. A total of 45 compounds were detected by UHPLC–HRMS analysis in A. vulgaris ethanolic extract. Measurement of antioxidant activity revealed the significant potential of the tested extract to scavenge free radicals. In addition, the analysis of micronuclei showed an in vitro protective effect on chromosome aberrations in peripheral human lymphocytes. A. vulgaris extract strongly suppressed the growth of human cell lines derived from different types of tumors (MCF-7, A375, A549, and HCT116). The observed antitumor effect is realized through the blockade of cell division, caspase-dependent apoptosis, and autophagic cell death. Our study has shown that Alchemilla vulgaris L. is a valuable source of bioactive compounds able to protect the subcellular structure from damage, thus preventing tumorigenesis as well as suppressing tumor cell growth. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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22 pages, 5671 KiB

Open AccessArticle

Cellular Antioxidant Properties of Ischnoderma Resinosum Polysaccharide

by Caiyu Liao, Liyan Wu, Wenting Zhong, Qinhua Zheng, Weijian Tan, Kexin Feng, Xiaolin Feng and Fanxin Meng

Molecules 2022, 27(22), 7717; https://doi.org/10.3390/molecules27227717 - 9 Nov 2022

Cited by 10 | Viewed by 1945

Abstract

A predominant polysaccharide isolated from Ischnoderma resinosum underwent evaluation for its capacity to scavenge free radicals and its potential antioxidant properties at a cellular-oriented level. This proved that Ischnoderma resinosum polysaccharide (IRP) remarkably curtailed AAPH-induced erythrocyte hemolysis through the inhibition of the generation [...] Read more.

A predominant polysaccharide isolated from Ischnoderma resinosum underwent evaluation for its capacity to scavenge free radicals and its potential antioxidant properties at a cellular-oriented level. This proved that Ischnoderma resinosum polysaccharide (IRP) remarkably curtailed AAPH-induced erythrocyte hemolysis through the inhibition of the generation of ROS (p < 0.05). Rather, it caused the restoration of intracellular antioxidant enzyme (SOD, GSH-Px, and CAT) activities at an acceptable pace and the silencing of intracellular MDA formation, as well as the rescaling of LDH leakage. Furthermore, a model of oxidative stress in HepG2 cells was established by adopting 400 μM of hydrogen peroxide, which suggested that IRP manifests promising antioxidant activity. Notably, after the intervention of IRP in the H₂O₂-induced HepG2 cells, there was a statistical elevation in cell survivability (p < 0.05). IRP diminished the morphological alterations in the nucleus and decreased the secretion of ROS (p < 0.05), with a dose-dependent abrogation of apoptosis (p < 0.05). Consequently, IRP, which was isolated and purified, was able to scavenge free radicals and possessed favorable antioxidant activity that could dampen the occurrence of oxidative stimulation and effectively alleviate the AAPH-induced erythrocyte hemolysis and H₂O₂-induced oxidative damage in HepG2 cells. This provides a basis and theoretical reference for the development and utilization of IRP as a natural antioxidant, with emphasis on the exploitation of environmentally friendly and cost-effective antioxidants. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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19 pages, 2937 KiB

Open AccessArticle

Comprehensive Biological Potential, Phytochemical Profiling Using GC-MS and LC-ESI-MS, and In-Silico Assessment of Strobilanthes glutinosus Nees: An Important Medicinal Plant

by Marya Aziz, Saeed Ahmad, Umair Khurshid, Irfan Pervaiz, Arslan Hussain Lodhi, Nasrullah Jan, Sameera Khurshid, Muhammad Adeel Arshad, Mohamed M. Ibrahim, Gaber A. M. Mersal, Fahaad S. Alenazi, Ahmed Awadh Saleh Alamri, Juwairiya Butt, Hammad Saleem and Zeinhom M. El-Bahy

Molecules 2022, 27(20), 6885; https://doi.org/10.3390/molecules27206885 - 14 Oct 2022

Cited by 7 | Viewed by 2516

Abstract

Plants of the genus Strobilanthes have notable use in folklore medicines as well as being used for pharmacological purposes. The present work explored the biological predispositions of Strobilanthes glutinosus and attempted to accomplish a comprehensive chemical profile through GC-MS of different fractions concerning [...] Read more.

Plants of the genus Strobilanthes have notable use in folklore medicines as well as being used for pharmacological purposes. The present work explored the biological predispositions of Strobilanthes glutinosus and attempted to accomplish a comprehensive chemical profile through GC-MS of different fractions concerning polarity (chloroform and n-butanol) and LC-ESI-MS of methanolic extract by both positive and negative ionization modes. The biological characteristics such as antioxidant potential were assessed by applying six different methods. The potential for clinically relevant enzyme (α-amylase, α-glucosidase, and tyrosinase) inhibition was examined. The DPPH, ABTS, CUPRAC, and FRAP results revealed that the methanol fraction presented efficient results. The phosphomolybdenum assay revealed that the n-hexane fraction showed the most efficient results, while maximum metal chelation potential was observed for the chloroform fraction. The GC-MS profiling of n-butanol and chloroform fractions revealed the existence of several (110) important compounds presenting different classes (fatty acids, phenols, alkanes, monoterpenes, diterpenes, sesquiterpenoids, and sterols), while LC-ESI-MS tentatively identified the presence of 44 clinically important secondary metabolites. The n-hexane fraction exhibited the highest potential against α-amylase (497.98 mm ACAE/g extract) and α-glucosidase (605.85 mm ACAE/g extract). Significant inhibitory activity against tyrosinase enzyme was displayed by fraction. Six of the prevailing compounds from the GC-MS study (lupeol, beta-amyrin, stigmasterol, gamma sitosterol, 9,12-octadecadienoic acid, and n-hexadecanoic acid) were modelled against α-glucosidase and α-amylase enzymes along with a comparison of binding affinity to standard acarbose, while three compounds identified through LC-ESI-MS were docked to the mushroom tyrosinase enzyme and presented with significant biding affinities. Thus, it is assumed that S. glutinosus demonstrated effective antioxidant and enzyme inhibition prospects with effective bioactive molecules, potentially opening the door to a new application in the field of medicine. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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24 pages, 4094 KiB

Open AccessArticle

Natural Phytocompounds from Common Indian Spices for Identification of Three Potential Inhibitors of Breast Cancer: A Molecular Modelling Approach

by Samik Hazra, Anindya Sundar Ray and Chowdhury Habibur Rahaman

Molecules 2022, 27(19), 6590; https://doi.org/10.3390/molecules27196590 - 5 Oct 2022

Cited by 4 | Viewed by 2985

Abstract

Breast cancer is the second most common cancer-related cause of death for women throughout the globe. In spite of some effective measures, the main concerns with traditional anti-cancer chemotherapy are its low bioavailability, physical side effects, acquired resistance of cancer cells and non-specific [...] Read more.

Breast cancer is the second most common cancer-related cause of death for women throughout the globe. In spite of some effective measures, the main concerns with traditional anti-cancer chemotherapy are its low bioavailability, physical side effects, acquired resistance of cancer cells and non-specific targeting. Now researchers have taken the initiative to establish natural product-based therapy methods and to identify viable hits for future lead optimization in the development of breast cancer medication. Our study aims to identify the potent phytocompounds from five very popular Indian spices (Zingiber officinale Roscoe, Cuminum cyminum L., Piper nigrum L., Curcuma longa L., and Allium sativum L.). From these spices, a total of 200 phytocompounds were identified and screened against three target genes, namely, cyclin-dependent kinase 8 (CDK 8), progesterone receptor (PR) and epidermal growth factor receptor (EGFR), through structure-based virtual screening using iGEMDOCK 2.1 software. Based on the binding affinity score, the top three phytocompounds against each target protein (cynaroside (−149.66 Kcal/mol), apigetrin (−139.527 Kcal/mol) and curcumin (−138.149 Kcal/mol) against CDK8; apigetrin (−123.298 Kcal/mol), cynaroside (−118.635 Kcal/mol) and xyloglucan (−113.788 Kcal/mol) against PR; cynaroside (−119.18 Kcal/mol), apigetrin (−105.185 Kcal/mol) and xyloglucan (−105.106 Kcal/mol) against EGFR) were selected. Apigetrin, cynaroside, curcumin, and xyloglucan were finally identified for further docking analysis with the respective three target proteins. Autodock 4.2 was applied to screen the optimal binding position and to assess the relative intensity of binding interactions. In addition, the ADME/T property checks and bioactivity scores analysis of were performed to understand the suitability of these four phytocompounds to be potential candidates for developing effective and non-toxic anticancer agents. Based on this in silico analysis, we believe this study could contribute to current efforts to develop new drugs for treating breast cancer. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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11 pages, 2354 KiB

Open AccessArticle

Chemical Profile and Biological Activities of Essential Oil from Piper arboreum for Development and Improvement of Mouthwash

by Edinardo Fagner Ferreira Matias, Ana Paula Dantas Pereira, Ana Valéria de Oliveira Braz, Mariana Carvalho Rodrigues, Jussara de Lima Silva, Philippe Alencar Araujo Maia, Sarah Castro dos Santos, Ricardo Andrade Rebelo, Ieda Maria Begnini, Luiz Everson da Silva, Wanderlei do Amaral, Grażyna Kowalska, Rafał Rowiński, Joanna Hawlena, Radosław Kowalski, Henrique Douglas Melo Coutinho and Vilson Rocha Cortez Teles de Alencar

Molecules 2022, 27(19), 6408; https://doi.org/10.3390/molecules27196408 - 28 Sep 2022

Cited by 2 | Viewed by 2011

Abstract

Studies show that more consumers are using natural health products in the modern world. We have noticed a growing demand in markets and the professional community for mouthwashes that contain natural compounds. The objective of this study was to assess the chemical characterization [...] Read more.

Studies show that more consumers are using natural health products in the modern world. We have noticed a growing demand in markets and the professional community for mouthwashes that contain natural compounds. The objective of this study was to assess the chemical characterization and microbiological potential of the essential oil Piper arboreum (EOPa) to provide data to enable the development of a low-cost mouthwash. The evaluation of the antibacterial and bacterial resistance modulating activity was performed by the microdilution method to determine the minimum inhibitory concentration. The chemical components were characterized by gas chromatography coupled with mass spectrometry, which identified 20 chemical constituents, with caryophyllene oxide being one of the major compounds. The EOPa showed an MIC ≥ 1024 µg/mL for all bacterial strains used in the tests. When evaluating the modulating activity of EOPa combined with chlorhexidine, mouthwash and antibiotics against the bacterial resistance, the oil limited synergistic activity between the MIC of the products tested in combination (37% to 87.5%). Therefore, we recommend expanding the tests with greater variation in the EOPa concentration and the products used, as well as toxicity assessments and in vivo testing, with the purpose of the development of a possible low-cost mouthwash base that is accessible to the most vulnerable populations. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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13 pages, 1592 KiB

Open AccessArticle

Essential Oil Variability in Iranian Populations of Heracleum persicum Desf. ex Fischer: A Rich Source of Hexyl Butyrate and Octyl Acetate

by Seyed Hamid Mustafavi, Amin Abbasi, Mohammad Reza Morshedloo, Mirian Pateiro and Jose M. Lorenzo

Molecules 2022, 27(19), 6296; https://doi.org/10.3390/molecules27196296 - 23 Sep 2022

Cited by 5 | Viewed by 1758

Abstract

Heracleum persicum Desf. ex Fischer seeds are a rich source of essential oils (EOs) with high antimicrobial and antioxidant effects. In order to determine the phytochemical variability in various Iranian H. persicum populations, seed samples were collected from 10 different climatic locations. The [...] Read more.

Heracleum persicum Desf. ex Fischer seeds are a rich source of essential oils (EOs) with high antimicrobial and antioxidant effects. In order to determine the phytochemical variability in various Iranian H. persicum populations, seed samples were collected from 10 different climatic locations. The current study indicated that hexyl butyrate (20.9–44.7%), octyl acetate (11.2–20.3%), hexyl-2-methylbutyrate (4.81–8.64%), and octyl 2-methyl butyrate (3.41–8.91%) were the major components of the EOs. The maximum (44.7%) and the minimum (20.9%) content of hexyl butyrate were obtained from Kaleibar and Sari populations, respectively. Moreover, the octyl acetate content ranged from 2% (in Mahdasht) to 20.3% in Torghabeh population. The CA and PCA analysis divided the 10 Iranian H. persicum populations into three major groups. Populations from Khanghah, Kaleibar, Shebeilo, Showt, Mahdasht, and Amin Abbad showed a distinct separation in comparison with the other populations, having high contents of hexyl butyrate (39.8%) and low contents of octyl acetate (13.5%) (Chemotype II). According to correlation analysis, the highest correlation coefficient was among habitat elevation and hexyl butyrate content. In addition, the mean annual precipitation was negatively correlated with the content of hexyl butyrate. Although octyl acetate content showed high correlation with soil EC and mean annual temperature, it was not statistically significant. In general, in order to have plants with a high content of hexyl butyrate, it is recommended to harvest these plants from regions with high altitude and low rainfall such as Kaleibar. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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11 pages, 3347 KiB

Open AccessArticle

GC-MS Chemical Characterization and Antibacterial Effect of the Essential oil of Piper mosenii

by Ana Valéria de Oliveira Braz, Mariana Carvalho Rodrigues, Philippe Alencar Araújo Maia, Ana Paula Dantas Pereira, Jussara de Lima Silva, Francisco Antonio Vieira dos Santos, Luiz Everson da Silva, Wanderley do Amaral, Maura Lins dos Santos, Henrique Douglas Melo Coutinho, Tomasz Baj, Grażyna Kowalska, Radosław Kowalski and Edinardo Fagner Ferreira Matias

Molecules 2022, 27(18), 5911; https://doi.org/10.3390/molecules27185911 - 12 Sep 2022

Cited by 1 | Viewed by 1915

Abstract

Commercialized mouthwashes are generally expensive for the most financially vulnerable populations. Thus, several studies evaluate the antimicrobial potential of herbal products, such as essential oils, to reduce the activity of microorganisms in the mouth. The objective of this research was to carry out [...] Read more.

Commercialized mouthwashes are generally expensive for the most financially vulnerable populations. Thus, several studies evaluate the antimicrobial potential of herbal products, such as essential oils, to reduce the activity of microorganisms in the mouth. The objective of this research was to carry out the chemical characterization and antibacterial activity of the essential oil of Piper mosenii (EOPm), providing data that enable the development of a low-cost mouthwash formulation aimed at vulnerable communities. The analysis of the antibacterial potential and modulator of bacterial resistance was verified by the microdilution method to determine the minimum inhibitory concentration-MIC. The chemical components were characterized by gas chromatography coupled to mass spectrometry, where 23 chemical constituents were detected, with α-pinene, being the major compound. The EOPm showed a MIC ≥ 1024 µg/mL for all bacterial strains used in the tests. When the EOPm modulating activity was evaluated together with chlorhexidine, mouthwash and antibiotics against bacterial resistance, the oil showed a significant synergistic effect, reducing the MIC of the products tested in combination, in percentages between 20.6% to 96.3%. Therefore, it is recommended to expand the tests with greater variation of EOPm concentration and the products used in this research, in addition to the evaluation of toxicity and in vivo tests, seeking the development of a possible formulation of mouthwash accessible to the vulnerable population. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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18 pages, 3441 KiB

Open AccessArticle

Multifaced Assessment of Antioxidant Power, Phytochemical Metabolomics, In-Vitro Biological Potential and In-Silico Studies of Neurada procumbens L.: An Important Medicinal Plant

by Umair Khurshid, Saeed Ahmad, Hammad Saleem, Arslan Hussain LodhI, Irfan Pervaiz, Mohsin Abbas Khan, Haroon Khan, Abdulwahab AlamrI, Mukhtar AnsarI, Marcello LocatellI, Muhammad Adeel Arshad, Muhammad Asif Wazir, Juwairiya Butt and Sirajudheen Anwar

Molecules 2022, 27(18), 5849; https://doi.org/10.3390/molecules27185849 - 9 Sep 2022

Cited by 2 | Viewed by 2192

Abstract

This work was undertaken to explore the phytochemical composition, antioxidant, and enzyme-inhibiting properties of Neurada procumbens L. extracts/fractions of varying polarity (methanol extract and its fractions including n-hexane, chloroform, n-butanol, and aqueous fractions). A preliminary phytochemical study of all extracts/fractions, HPLC-PDA [...] Read more.

This work was undertaken to explore the phytochemical composition, antioxidant, and enzyme-inhibiting properties of Neurada procumbens L. extracts/fractions of varying polarity (methanol extract and its fractions including n-hexane, chloroform, n-butanol, and aqueous fractions). A preliminary phytochemical study of all extracts/fractions, HPLC-PDA polyphenolic quantification, and GC-MS analysis of the n-hexane fraction were used to identify the phytochemical makeup. Antioxidant (DPPH), enzyme inhibition (against xanthine oxidase, carbonic anhydrase, and urease enzymes), and antibacterial activities against seven bacterial strains were performed for biological investigation. The GC-MS analysis revealed the tentative identification of 22 distinct phytochemicals in the n-hexane fraction, the majority of which belonged to the phenol, flavonoid, sesquiterpenoid, terpene, fatty acid, sterol, and triterpenoid classes of secondary metabolites. HPLC-PDA analysis quantified syringic acid, 3-OH benzoic acid, t-ferullic acid, naringin, and epicatechin in a significant amount. All of the studied extracts/fractions displayed significant antioxidant capability, with methanol extract exhibiting the highest radical-scavenging activity, as measured by an inhibitory percentage of 81.4 ± 0.7 and an IC₅₀ value of 1.3 ± 0.3. For enzyme inhibition experiments, the n-hexane fraction was shown to be highly potent against xanthine oxidase and urease enzymes, with respective IC₅₀ values of 2.3 ± 0.5 and 1.1 ± 0.4 mg/mL. Similarly, the methanol extract demonstrated the strongest activity against the carbonic anhydrase enzyme, with an IC₅₀ value of 2.2 ± 0.4 mg/mL. Moreover, all the studied extracts/fractions presented moderate antibacterial potential against seven bacterial strains. Molecular docking of the five molecules β-amyrin, campesterol, ergosta-4,6,22-trien-3β-ol, stigmasterol, and caryophyllene revealed the interaction of these ligands with the investigated enzyme (xanthine oxidase). The results of the present study suggested that the N. procumbens plant may be evaluated as a possible source of bioactive compounds with multifunctional therapeutic applications. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 34217 KiB

Open AccessArticle

Evaluation of the In Vitro Wound-Healing Potential of Ayahuasca

by Joana Gonçalves, Ângelo Luís, Eugenia Gallardo and Ana Paula Duarte

Molecules 2022, 27(18), 5760; https://doi.org/10.3390/molecules27185760 - 6 Sep 2022

Cited by 2 | Viewed by 2528

Abstract

Ayahuasca is an Amazonian drink, which contains β-carboline alkaloids and N,N-dimethyltryptamine. The aim of this study was to evaluate the healing potential of decoctions of a commercial mixture, four individual plants and four mixtures of two plants used in the [...] Read more.

Ayahuasca is an Amazonian drink, which contains β-carboline alkaloids and N,N-dimethyltryptamine. The aim of this study was to evaluate the healing potential of decoctions of a commercial mixture, four individual plants and four mixtures of two plants used in the ayahuasca preparation. Thus, the cytotoxic potential of the samples was evaluated and a wound-healing assay was performed with a NHDF cell line. Subsequently, a parallel artificial membrane permeability assay was also performed, to verify if any psychoactive compound could be absorbed by skin fibroblasts. The integrity and permeability of the cell layer were also evaluated, using the transepithelial electrical resistance assay and Lucifer yellow permeability assay, respectively. The compounds absorbed by the cell layer were quantified by high-performance liquid chromatography coupled to a diode array detector. The results showed that only one sample showed cytotoxicity and all the others promoted the migration of skin fibroblasts. Additionally, it was also verified that β-carbolynic alkaloids and N,N-dimethyltriptamine were not absorbed by the cell layer, and in general, did not interfere with its permeability and integrity. To the best of our knowledge, this is the first study where ayahuasca’s wound-healing potential was evaluated. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

13 pages, 1472 KiB

Open AccessArticle

Optimization of Flavonoid Extraction from Salix babylonica L. Buds, and the Antioxidant and Antibacterial Activities of the Extract

by Peng Zhang, Yuwen Song, Hongling Wang, Yujie Fu, Yingying Zhang and Korotkova Irina Pavlovna

Molecules 2022, 27(17), 5695; https://doi.org/10.3390/molecules27175695 - 3 Sep 2022

Cited by 10 | Viewed by 2195

Abstract

The present study was designed to evaluate the chemical extraction, chemical composition, and antioxidant and antibacterial properties of the total flavonoids in Willow Buds (TFW). We investigated the optimal extraction of TFW using response surface methodology (RSM). Chemical compounds were analyzed using Q-Orbitrap [...] Read more.

The present study was designed to evaluate the chemical extraction, chemical composition, and antioxidant and antibacterial properties of the total flavonoids in Willow Buds (TFW). We investigated the optimal extraction of TFW using response surface methodology (RSM). Chemical compounds were analyzed using Q-Orbitrap LC–MS/MS. The DPPH radical scavenging capacity, hydroxy radical inhibitory ability, and superoxide anion radical inhibitory ability were explored to determine the antioxidant properties of flavonoid extractions. The antibacterial effect was assessed via minimal inhibitory concentration. The results demonstrated that the optimal extraction conditions were an ethanol concentration of 50%, a time of 35 min, and a liquid/material ratio of 70:1 mL/g. Under these conditions, the yield of TFW was 7.57%. Eight flavonoids, a phenolic glycoside, and an alkaloid were enriched in the Willow Buds. The TFW exhibited significant antioxidant activity, with IC₅₀ values of 0.18-0.24 mg/mL and antimicrobial activity against Escherichia coli, Salmonella enterica, Staphylococcus aureus, and Streptococcus pneumoniae. TFW may be explored as potential and natural compounds in food and pharmacological applications. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 5403 KiB

Open AccessArticle

Optimization of Polyphenols’ Recovery from Purple Corn Cobs Assisted by Infrared Technology and Use of Extracted Anthocyanins as a Natural Colorant in Pickled Turnip

by Francisco J. Barba, Hiba N. Rajha, Espérance Debs, Anna-Maria Abi-Khattar, Stéphanie Khabbaz, Basharat Nabi Dar, Mario J. Simirgiotis, Juan Manuel Castagnini, Richard G. Maroun and Nicolas Louka

Molecules 2022, 27(16), 5222; https://doi.org/10.3390/molecules27165222 - 16 Aug 2022

Cited by 14 | Viewed by 2654

Abstract

An ecofriendly extraction technology using infrared (IR) irradiation Ired-Irrad^® was applied to purple corn cobs to enhance polyphenol recovery for the first time. The IR extraction efficiency was compared to that of the water bath (WB) method. Response surface methodology (RSM) using [...] Read more.

An ecofriendly extraction technology using infrared (IR) irradiation Ired-Irrad^® was applied to purple corn cobs to enhance polyphenol recovery for the first time. The IR extraction efficiency was compared to that of the water bath (WB) method. Response surface methodology (RSM) using a central composite design was conducted to determine the effect of the experimental conditions (extraction time and treatment temperature) and their interactions on the total polyphenol and anthocyanin yields. Optimal extraction of total phenolic compounds (37 mg GAE/g DM) and total monomeric anthocyanins (14 mg C3G/g DM) were obtained at 63 °C for 77 min using IR as an extraction technique and water as a solvent. HPLC revealed that the recovery of peonidin 3-O-glucoside and cyanidin 3-O-glucoside was enhanced by 26% and 34%, respectively, when using IR. Finally, purple corn cobs’ spray-dried extract was proven to be an important natural colorant of pickled turnip. It offers great potential for use as a healthy alternative to the carcinogenic rhodamine B synthetic dye, which was banned. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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21 pages, 2931 KiB

Open AccessArticle

Which Extraction Solvents and Methods Are More Effective in Terms of Chemical Composition and Biological Activity of Alcea fasciculiflora from Turkey?

by Refiye Beyza Ozturk, Gokhan Zengin, Kouadio Ibrahime Sinan, Domenico Montesano, Dimitrina Zheleva-Dimitrova, Reneta Gevrenova, Abdullahi Ibrahim Uba, Uğur Çakılcıoğlu, Alevcan Kaplan, Sharmeen Jugreet, Stefano Dall’Acqua and Mohamad Fawzi Mahomoodally

Molecules 2022, 27(15), 5011; https://doi.org/10.3390/molecules27155011 - 6 Aug 2022

Cited by 9 | Viewed by 2880

Abstract

The bioactive content, antioxidant properties, and enzyme inhibition properties of extracts of Alcea fasciculiflora from Turkey prepared with different solvents (water, methanol, ethyl acetate) and extraction methods (maceration, soxhlet, homogenizer assisted extraction, and ultrasound assisted extraction) were examined in this study. UHPLC-HRMS analysis [...] Read more.

The bioactive content, antioxidant properties, and enzyme inhibition properties of extracts of Alcea fasciculiflora from Turkey prepared with different solvents (water, methanol, ethyl acetate) and extraction methods (maceration, soxhlet, homogenizer assisted extraction, and ultrasound assisted extraction) were examined in this study. UHPLC-HRMS analysis detected or annotated a total of 50 compounds in A. fasciculiflora extracts, including 18 hydroxybenzoic and hydroxycinnamic acids, 7 Hexaric acids, 7 Coumarins, 15 Flavonoids, and 3 hydroxycinnamic acid amides. The extracts had phenolic and flavonoid levels ranging from 14.25 to 24.87 mg GAE/g and 1.68 to 25.26 mg RE/g, respectively, in the analysis. Both DPPH and ABTS tests revealed radical scavenging capabilities (between 2.63 and 35.33 mg TE/g and between 13.46 and 76.27 mg TE/g, respectively). The extracts had reducing properties (CUPRAC: 40.38–78 TE/g and FRAP: 17.51–42.58 TE/g). The extracts showed metal chelating activity (18.28–46.71 mg EDTAE/g) as well as total antioxidant capacity (phosphomolybdenum test) (0.90–2.12 mmol TE/g). DPPH, ABTS, FRAP, and metal chelating tests indicated the water extracts to be the best antioxidants, while the ethyl acetate extracts had the highest overall antioxidant capacity regardless of the extraction technique. Furthermore, anti-acetylcholinesterase activity was identified in all extracts (0.17–2.80 mg GALAE/g). The water extracts and the ultrasound-assisted ethyl acetate extract were inert against butyrylcholinesterase, but the other extracts showed anti-butyrylcholinesterase activity (1.17–5.80 mg GALAE/g). Tyrosine inhibitory action was identified in all extracts (1.79–58.93 mg KAE/g), with the most effective methanolic extracts. Only the ethyl acetate and methanolic extracts produced by maceration and homogenizer aided extraction showed glucosidase inhibition (0.11–1.11 mmol ACAE/g). These findings showed the overall bioactivity of the different extracts of A. fasciculiflora and provided an overview of the combination of solvent type and extraction method that could yield bioactive profile and pharmacological properties of interest and hence, could be a useful reference for future studies on this species. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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19 pages, 3434 KiB

Open AccessArticle

Formulation, Optimization, and Evaluation of Moringa oleifera Leaf Polyphenol-Loaded Phytosome Delivery System against Breast Cancer Cell Lines

by Jecinta Wanjiru, Jeremiah Gathirwa, Elingarami Sauli and Hulda Shaid Swai

Molecules 2022, 27(14), 4430; https://doi.org/10.3390/molecules27144430 - 11 Jul 2022

Cited by 18 | Viewed by 4252

Abstract

Moringa oleifera leaf polyphenols (Mopp) were encapsulated with phytosomes to enhance their efficacy on 4T1 cancer cell lines. The Mopp were extracted via microwave-assisted extraction. Moringa oleifera polyphenol-loaded phytosomes (MoP) were prepared with the nanoprecipitation method and characterized using the dynamic light scattering [...] Read more.

Moringa oleifera leaf polyphenols (Mopp) were encapsulated with phytosomes to enhance their efficacy on 4T1 cancer cell lines. The Mopp were extracted via microwave-assisted extraction. Moringa oleifera polyphenol-loaded phytosomes (MoP) were prepared with the nanoprecipitation method and characterized using the dynamic light scattering and dialysis membrane techniques. The in vitro cytotoxic and antiproliferative activity were investigated with the (3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazole) MTT assay. Acute toxicity was assessed using Swiss albino mice. An MoP particle size of 296 ± 0.29 nm, −40.1 ± 1.19 mV zeta potential, and polydispersity index of 0.106 ± 0.002 were obtained. The total phenolic content was 50.81 ± 0.02 mg GAE/g, while encapsulation efficiency was 90.32 ± 0.11%. The drug release profiles demonstrated biphasic and prolonged subsequent sustained release. In vitro assays indicated MoP had a low cytotoxicity effect of 98.84 ± 0.53 μg/mL, doxorubicin was 68.35 ± 3.508, and Mopp was 212.9 ± 1.30 μg/mL. Moreover, MoP exhibited the highest antiproliferative effect on 4T1 cancer cells with an inhibitory concentration of 7.73 ± 2.87 μg/mL and selectivity index > 3. The results indicated a significant difference (p ≤ 0.001) in MoP when compared to Mopp and doxorubicin. The in vivo investigation showed the safety of MoP at a dose below 2000 mg/kg. The present findings suggest that MoP may serve as an effective and promising formulation for breast cancer drug delivery and therapy. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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29 pages, 5684 KiB

Open AccessArticle

Membrane Permeabilization and Antimicrobial Activity of Recombinant Defensin-d2 and Actifensin against Multidrug-Resistant Pseudomonas aeruginosa and Candida albicans

by Ifeoluwa D. Gbala, Rosaline W. Macharia, Joel L. Bargul and Gabriel Magoma

Molecules 2022, 27(14), 4325; https://doi.org/10.3390/molecules27144325 - 6 Jul 2022

Cited by 9 | Viewed by 3181

Abstract

Antimicrobial resistance requires urgent efforts towards the discovery of active antimicrobials, and the development of strategies to sustainably produce them. Defensin and defensin-like antimicrobial peptides (AMPs) are increasingly gaining pharmacological interest because of their potency against pathogens. In this study, we expressed two [...] Read more.

Antimicrobial resistance requires urgent efforts towards the discovery of active antimicrobials, and the development of strategies to sustainably produce them. Defensin and defensin-like antimicrobial peptides (AMPs) are increasingly gaining pharmacological interest because of their potency against pathogens. In this study, we expressed two AMPs: defensin-d2 derived from spinach, and defensin-like actifensin from Actinomyces ruminicola. Recombinant pTXB1 plasmids carrying the target genes encoding defensin-d2 and actifensin were generated by the MEGAWHOP cloning strategy. Each AMP was first expressed as a fusion protein in Escherichia coli, purified by affinity chromatography, and was thereafter assayed for antimicrobial activity against multidrug-resistant (MDR) pathogens. Approximately 985 µg/mL and 2895 µg/mL of recombinant defensin-d2 and actifensin, respectively, were recovered with high purity. An analysis by MALDI-TOF MS showed distinct peaks corresponding to molecular weights of approximately 4.1 kDa for actifensin and 5.8 kDa for defensin-d2. An in vitro antimicrobial assay showed that MDR Pseudomonas aeruginosa and Candida albicans were inhibited at minimum concentrations of 7.5 µg/mL and 23 µg/mL for recombinant defensin-d2 and actifensin, respectively. The inhibitory kinetics of the peptides revealed cidal activity within 4 h of the contact time. Furthermore, both peptides exhibited an antagonistic interaction, which could be attributed to their affinities for similar ligands, as deduced by peptide–ligand profiling. Moreover, both peptides inhibited biofilm formation, and they exhibited no resistance potential and low hemolytic activity. The peptides also possess the ability to permeate and disrupt the cell membranes of MDR P. aeruginosa and C. albicans. Therefore, recombinant actifensin and defensin-d2 exhibit broad-spectrum antimicrobial activity and have the potential to be used as therapy against MDR pathogens. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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Review

Jump to: Research, Other

37 pages, 9496 KiB

Open AccessReview

Cajaninstilbene Acid and Its Derivative as Multi-Therapeutic Agents: A Comprehensive Review

by Wen Hou, Lejun Huang, Jinyang Wang, Walter Luyten, Jia Lai, Zhinuo Zhou, Sishuang Kang, Ping Dai, Yanzhu Wang, Hao Huang and Jinxia Lan

Molecules 2024, 29(22), 5440; https://doi.org/10.3390/molecules29225440 - 18 Nov 2024

Viewed by 349

Abstract

Pigeon pea (Cajanus cajan (L.) Millsp.) is a traditional Chinese medicinal plant widely utilized in folk medicine due to its significant pharmacological and nutritional properties. Cajaninstilbene acid (CSA), a stilbene compound derived from pigeon pea leaves, has been extensively investigated since the [...] Read more.

Pigeon pea (Cajanus cajan (L.) Millsp.) is a traditional Chinese medicinal plant widely utilized in folk medicine due to its significant pharmacological and nutritional properties. Cajaninstilbene acid (CSA), a stilbene compound derived from pigeon pea leaves, has been extensively investigated since the 1980s. A thorough understanding of CSA’s mechanisms of action and its therapeutic effects on various diseases is crucial for developing novel therapeutic approaches. This paper presents an overview of recent research advancements concerning the biological activities and mechanisms of CSA and its derivatives up to February 2024. The review encompasses discussions on the in vivo metabolism of CSA and its derivatives, including antipathogenic micro-organisms activity, anti-tumor activity, systematic and organ protection activity (such as bone protection, cardiovascular protection, neuroprotection), anti-inflammatory activity, antioxidant activity, immune regulation as well as action mechanism of CSA and its derivatives. The most studied activities are antipathogenic micro-organisms activities. Additionally, the structure–activity relationships of CSA and its derivatives as well as the total synthesis of CSA are explored, highlighting the potential for developing new pharmaceutical agents. This review aims to provide a foundation for future clinical applications of CSA and its derivatives. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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34 pages, 2722 KiB

Open AccessReview

Antimicrobial Properties and Therapeutic Potential of Bioactive Compounds in Nigella sativa: A Review

by Munawar Abbas, Mayank Anand Gururani, Amjad Ali, Sakeena Bajwa, Rafia Hassan, Syeda Wajiha Batool, Mahreen Imam and Dongqing Wei

Molecules 2024, 29(20), 4914; https://doi.org/10.3390/molecules29204914 - 17 Oct 2024

Viewed by 2263

Abstract

Nigella sativa (N. sativa; Ranunculaceae), commonly referred to as black cumin, is one of the most widely used medicinal plants worldwide, with its seeds having numerous applications in the pharmaceutical and food industries. With the emergence of antibiotic resistance in pathogens [...] Read more.

Nigella sativa (N. sativa; Ranunculaceae), commonly referred to as black cumin, is one of the most widely used medicinal plants worldwide, with its seeds having numerous applications in the pharmaceutical and food industries. With the emergence of antibiotic resistance in pathogens as an important health challenge, the need for alternative microbe-inhibitory agents is on the rise, whereby black cumin has gained considerable attention from researchers for its strong antimicrobial characteristics owing to its high content in a wide range of bioactive compounds, including thymoquinone, nigellimine, nigellidine, quercetin, and O-cymene. Particularly, thymoquinone increases the levels of antioxidant enzymes that counter oxidative stress in the liver. Additionally, the essential oil in N. sativa seeds effectively inhibits intestinal parasites and shows moderate activity against some bacteria, including Bacillus subtilis and Staphylococcus aureus. Thymoquinone exhibits minimum inhibitory concentrations (MICs) of 8–16 μg/mL against methicillin-resistant Staphylococcus aureus (MRSA) and exhibits MIC 0.25 µg/mL against drug-resistant mycobacteria. Similarly, quercetin shows a MIC of 2 mg/mL against oral pathogens, such as Streptococcus mutans and Lactobacillus acidophilus. Furthermore, endophytic fungi isolated from N. sativa have demonstrated antibacterial activity. Therefore, N. sativa is a valuable medicinal plant with potential for medicinal and food-related applications. In-depth exploration of the corresponding therapeutic potential and scope of industrial application warrants further research. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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25 pages, 3666 KiB

Open AccessReview

Natural Products with Potential Effects on Hemorrhoids: A Review

by Yicheng Liang, Tankun Ren, Ruyi Li, Zhonghui Yu, Yu Wang, Xin Zhang, Zonglin Qin, Jinlong Li, Jing Hu and Chuanhong Luo

Molecules 2024, 29(11), 2673; https://doi.org/10.3390/molecules29112673 - 5 Jun 2024

Viewed by 5748

Abstract

Hemorrhoid disease is a common anorectal disorder affecting populations worldwide, with high prevalence, treatment difficulties, and considerable treatment costs. Compared to other treatment options, medical therapy for hemorrhoids offers minimal harm, more dignity to patients, and is more economical. Unfortunately, there are few [...] Read more.

Hemorrhoid disease is a common anorectal disorder affecting populations worldwide, with high prevalence, treatment difficulties, and considerable treatment costs. Compared to other treatment options, medical therapy for hemorrhoids offers minimal harm, more dignity to patients, and is more economical. Unfortunately, there are few chemical hemorrhoid medications available clinically, which makes the search for efficacious, cost-effective, and environmentally friendly new medication classes a focal point of research. In this context, searching for available natural products to improve hemorrhoids exhibits tremendous potential. These products are derived from nature, predominantly from plants, with a minor portion coming from animals, fungi, and algae. They have excellent coagulation pathway regulation, anti-inflammatory, antibacterial, and tissue regeneration activities. Therefore, we take the view that they are a class of potential hemorrhoid drugs, prevention products, and medication add-on ingredients. This article first reviews the factors contributing to the development of hemorrhoids, types, primary symptoms, and the mechanisms of natural products for hemorrhoids. Building on this foundation, we screened natural products with potential hemorrhoid improvement activity, including polyphenols and flavonoids, terpenes, polysaccharides, and other types. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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15 pages, 3648 KiB

Open AccessReview

Exploring the Pharmacological Potential of Lithospermum officinale L.: A Review of Phytochemicals and Ethnomedicinal Uses

by Gulzhanat Barkizatova, Aknur Turgumbayeva, Kairat Zhakipbekov, Kuralay Bekesheva, Zhalgaskali Arystanov, Tanagul Arystanova, Farida Kayupova, Klara Zhumalina, Zhanat Toxanbayeva, Aigul Ibragimova, Olga Blinova, Gulnara Utegenova, Nurzhan Iztileu and Zhanserik Shynykul

Molecules 2024, 29(8), 1856; https://doi.org/10.3390/molecules29081856 - 19 Apr 2024

Viewed by 1202

Abstract

Exploring phytochemicals from ethnomedicinal plants for pharmacological applications is a promising research area. By studying ethnomedicine, researchers can identify plants used for centuries to treat ailments and investigate their phytochemicals. Consequently, phytochemicals can be isolated, characterized, and tested for pharmacological activities, leading to [...] Read more.

Exploring phytochemicals from ethnomedicinal plants for pharmacological applications is a promising research area. By studying ethnomedicine, researchers can identify plants used for centuries to treat ailments and investigate their phytochemicals. Consequently, phytochemicals can be isolated, characterized, and tested for pharmacological activities, leading to new drug development. This research also helps preserve traditional knowledge and biodiversity. Lithospermum officinale L., found in Eurasia, Argentina (South), Colombia, and the United States, is valued for its medicinal properties, including anti-inflammatory, antioxidant, and antimicrobial effects. The current review emphasizes L. officinale L. as a significant reservoir of bioactive phytochemicals, with alkaloids, quinones, glucosides, phenolics, flavonoids, and lipids identified as the principal metabolites. It also unveils the unexplored potential of this plant for future research endeavors. Continued research on L. officinale L. can unlock its full potential, providing insights into its medicinal uses and contributing to biodiversity preservation. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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51 pages, 4628 KiB

Open AccessReview

Bioactivities and Mechanisms of Action of Sinomenine and Its Derivatives: A Comprehensive Review

by Wen Hou, Lejun Huang, Hao Huang, Shenglan Liu, Wei Dai, Jianhong Tang, Xiangzhao Chen, Xiaolu Lu, Qisheng Zheng, Zhinuo Zhou, Ziyun Zhang and Jinxia Lan

Molecules 2024, 29(2), 540; https://doi.org/10.3390/molecules29020540 - 22 Jan 2024

Cited by 6 | Viewed by 2944

Abstract

Sinomenine, an isoquinoline alkaloid extracted from the roots and stems of Sinomenium acutum, has been extensively studied for its derivatives as bioactive agents. This review concentrates on the research advancements in the biological activities and action mechanisms of sinomenine-related compounds until November [...] Read more.

Sinomenine, an isoquinoline alkaloid extracted from the roots and stems of Sinomenium acutum, has been extensively studied for its derivatives as bioactive agents. This review concentrates on the research advancements in the biological activities and action mechanisms of sinomenine-related compounds until November 2023. The findings indicate a broad spectrum of pharmacological effects, including antitumor, anti-inflammation, neuroprotection, and immunosuppressive properties. These compounds are notably effective against breast, lung, liver, and prostate cancers, exhibiting IC₅₀ values of approximately 121.4 nM against PC-3 and DU-145 cells, primarily through the PI3K/Akt/mTOR, NF-κB, MAPK, and JAK/STAT signaling pathways. Additionally, they manifest anti-inflammatory and analgesic effects predominantly via the NF-κB, MAPK, and Nrf2 signaling pathways. Utilized in treating rheumatic arthritis, these alkaloids also play a significant role in cardiovascular and cerebrovascular protection, as well as organ protection through the NF-κB, Nrf2, MAPK, and PI3K/Akt/mTOR signaling pathways. This review concludes with perspectives and insights on this topic, highlighting the potential of sinomenine-related compounds in clinical applications and the development of medications derived from natural products. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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19 pages, 1526 KiB

Open AccessReview

Antimicrobial and Other Pharmacological Properties of Ocimum basilicum, Lamiaceae

by Kairat Zhakipbekov, Aknur Turgumbayeva, Sholpan Akhelova, Kymbat Bekmuratova, Olga Blinova, Gulnara Utegenova, Klara Shertaeva, Nurlan Sadykov, Kuanysh Tastambek, Akzharkyn Saginbazarova, Kenzhebek Urazgaliyev, Gulbanu Tulegenova, Zere Zhalimova and Zhanylsyn Karasova

Molecules 2024, 29(2), 388; https://doi.org/10.3390/molecules29020388 - 12 Jan 2024

Cited by 8 | Viewed by 4339

Abstract

Since ancient times, various scientists and doctors have utilized different herbs to heal diseases. Due to the rise in drug resistance and the negative effects of chemosynthetic drugs, researchers and the general public around the world have become more interested in medicinal herbs [...] Read more.

Since ancient times, various scientists and doctors have utilized different herbs to heal diseases. Due to the rise in drug resistance and the negative effects of chemosynthetic drugs, researchers and the general public around the world have become more interested in medicinal herbs and plant metabolites/extracts. This is due to its non-toxicity and its several health benefits when used to treat diseases in clinical and medical settings. Ocimum basilicum is one such plant, possessing a wide range of bioactive phytochemicals including alkaloids, phenolics, flavonoids, tannins, saponins, reducing sugars, cardiac glycosides, steroids and glycosides, as well as complex pharmacological activities, including anti-inflammatory, antifungal, antibacterial, antioxidant, wound healing and antiviral properties. The results of many studies on Ocimum basilicum plant extracts are collected and presented in this review. The plant extracts have excellent potential to be used as medicinal raw materials, and exhibit an extensive variety of therapeutic capacities, including antibacterial, antioxidant, wound healing, anti-inflammatory, antifungal, and antiviral properties. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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19 pages, 2669 KiB

Open AccessReview

Potential Immunoregulatory Mechanism of Plant Saponins: A Review

by Liuhong Shen, Hao Luo, Lei Fan, Xinyu Tian, Anguo Tang, Xiaofeng Wu, Ke Dong and Zhetong Su

Molecules 2024, 29(1), 113; https://doi.org/10.3390/molecules29010113 - 23 Dec 2023

Cited by 3 | Viewed by 3131

Abstract

Saponins are extracted from different parts of plants such as seeds, roots, stems, and leaves and have a variety of biological activities including immunomodulatory, anti-inflammatory effects, and hypoglycemic properties. They demonstrate inherent low immunogenicity and possess the capacity to effectively regulate both the [...] Read more.

Saponins are extracted from different parts of plants such as seeds, roots, stems, and leaves and have a variety of biological activities including immunomodulatory, anti-inflammatory effects, and hypoglycemic properties. They demonstrate inherent low immunogenicity and possess the capacity to effectively regulate both the innate and adaptive immune responses. Plant saponins can promote the growth and development of the body’s immune organs through a variety of signaling pathways, regulate the activity of a variety of immune cells, and increase the secretion of immune-related cytokines and antigen-specific antibodies, thereby exerting the role of immune activity. However, the chemical structure of plant saponins determines its certain hemolytic and cytotoxicity. With the development of science and technology, these disadvantages can be avoided or reduced by certain technical means. In recent years, there has been a significant surge in interest surrounding the investigation of plant saponins as immunomodulators. Consequently, the objective of this review is to thoroughly examine the immunomodulatory properties of plant saponins and elucidate their potential mechanisms, with the intention of offering a valuable point of reference for subsequent research and advancement within this domain. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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23 pages, 16755 KiB

Open AccessReview

Bioactivities and Mechanisms of Action of Diphyllin and Its Derivatives: A Comprehensive Systematic Review

by Wen Hou, Le-Jun Huang, Hao Huang, Sheng-Lan Liu, Wei Dai, Zeng-Min Li, Zhen-Yu Zhang, Su-Ya Xin, Jin-Yang Wang, Zi-Yun Zhang, Xi Ouyang and Jin-Xia Lan

Molecules 2023, 28(23), 7874; https://doi.org/10.3390/molecules28237874 - 30 Nov 2023

Cited by 6 | Viewed by 1880

Abstract

Natural products are treasure houses for modern drug discovery. Diphyllin is a natural arylnaphthalene lignan lactone isolated from the leaf of Astilboides tabularis. Studies have found that it possesses plenty of bioactivity characteristics. In this paper, we reviewed the structure, bioactivity, and [...] Read more.

Natural products are treasure houses for modern drug discovery. Diphyllin is a natural arylnaphthalene lignan lactone isolated from the leaf of Astilboides tabularis. Studies have found that it possesses plenty of bioactivity characteristics. In this paper, we reviewed the structure, bioactivity, and mechanism of action of diphyllin and its derivatives. The references were obtained from PubMed, Web of Science, and Science Direct databases up to August 2023. Papers without a bio-evaluation were excluded. Diphyllin and its derivatives have demonstrated V-ATPase inhibition, anti-tumor, anti-virus, anti-biofilm, anti-inflammatory, and anti-oxidant activities. The most studied activities of diphyllin and its derivatives are V-ATPase inhibition, anti-tumor activities, and anti-virus activities. Furthermore, V-ATPase inhibition activity is the mechanism of many bioactivities, including anti-tumor, anti-virus, and anti-inflammatory activities. We also found that the galactosylated modification of diphyllin is a common phenomenon in plants, and therefore, galactosylated modification is applied by researchers in the laboratory to obtain more excellent diphyllin derivatives. This review will provide useful information for the development of diphyllin-based anti-tumor and anti-virus compounds. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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27 pages, 3878 KiB

Open AccessReview

Chemical Properties and Biological Activity of Bee Pollen

by Cristina Rodríguez-Pólit, Rebeca Gonzalez-Pastor, Jorge Heredia-Moya, Saskya E. Carrera-Pacheco, Fabián Castillo-Solis, Roberto Vallejo-Imbaquingo, Carlos Barba-Ostria and Linda P. Guamán

Molecules 2023, 28(23), 7768; https://doi.org/10.3390/molecules28237768 - 25 Nov 2023

Cited by 4 | Viewed by 4948

Abstract

Pollen, a remarkably versatile natural compound collected by bees for its abundant source of proteins and nutrients, represents a rich reservoir of diverse bioactive compounds with noteworthy chemical and therapeutic potential. Its extensive biological effects have been known and exploited since ancient times. [...] Read more.

Pollen, a remarkably versatile natural compound collected by bees for its abundant source of proteins and nutrients, represents a rich reservoir of diverse bioactive compounds with noteworthy chemical and therapeutic potential. Its extensive biological effects have been known and exploited since ancient times. Today, there is an increased interest in finding natural compounds against oxidative stress, a factor that contributes to various diseases. Recent research has unraveled a multitude of biological activities associated with bee pollen, ranging from antioxidant, anti-inflammatory, antimicrobial, and antifungal properties to potential antiviral and anticancer applications. Comprehending the extensive repertoire of biological properties across various pollen sources remains challenging. By investigating a spectrum of pollen types and their chemical composition, this review produces an updated analysis of the bioactive constituents and the therapeutic prospects they offer. This review emphasizes the necessity for further exploration and standardization of diverse pollen sources and bioactive compounds that could contribute to the development of innovative therapies. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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27 pages, 3266 KiB

Open AccessReview

The Pharmacological Implications of Flavopiridol: An Updated Overview

by Hemant Joshi, Hardeep Singh Tuli, Anuj Ranjan, Abhishek Chauhan, Shafiul Haque, Seema Ramniwas, Gurpreet Kaur Bhatia and Divya Kandari

Molecules 2023, 28(22), 7530; https://doi.org/10.3390/molecules28227530 - 10 Nov 2023

Cited by 8 | Viewed by 2263

Abstract

Flavopiridol is a flavone synthesized from the natural product rohitukine, which is derived from an Indian medicinal plant, namely Dysoxylum binectariferum Hiern. A deeper understanding of the biological mechanisms by which such molecules act may allow scientists to develop effective therapeutic strategies [...] Read more.

Flavopiridol is a flavone synthesized from the natural product rohitukine, which is derived from an Indian medicinal plant, namely Dysoxylum binectariferum Hiern. A deeper understanding of the biological mechanisms by which such molecules act may allow scientists to develop effective therapeutic strategies against a variety of life-threatening diseases, such as cancer, viruses, fungal infections, parasites, and neurodegenerative diseases. Mechanistic insight of flavopiridol reveals its potential for kinase inhibitory activity of CDKs (cyclin-dependent kinases) and other kinases, leading to the inhibition of various processes, including cell cycle progression, apoptosis, tumor proliferation, angiogenesis, tumor metastasis, and the inflammation process. The synthetic derivatives of flavopiridol have overcome a few demerits of its parent compound. Moreover, these derivatives have much improved CDK-inhibitory activity and therapeutic abilities for treating severe human diseases. It appears that flavopiridol has potential as a candidate for the formulation of an integrated strategy to combat and alleviate human diseases. This review article aims to unravel the potential therapeutic effectiveness of flavopiridol and its possible mechanism of action. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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33 pages, 2991 KiB

Open AccessReview

Bioactive Metabolites from Terrestrial and Marine Actinomycetes

by Chananan Ngamcharungchit, Nutsuda Chaimusik, Watanalai Panbangred, Jirayut Euanorasetr and Bungonsiri Intra

Molecules 2023, 28(15), 5915; https://doi.org/10.3390/molecules28155915 - 6 Aug 2023

Cited by 21 | Viewed by 9763

Abstract

Actinomycetes inhabit both terrestrial and marine ecosystems and are highly proficient in producing a wide range of natural products with diverse biological functions, including antitumor, immunosuppressive, antimicrobial, and antiviral activities. In this review, we delve into the life cycle, ecology, taxonomy, and classification [...] Read more.

Actinomycetes inhabit both terrestrial and marine ecosystems and are highly proficient in producing a wide range of natural products with diverse biological functions, including antitumor, immunosuppressive, antimicrobial, and antiviral activities. In this review, we delve into the life cycle, ecology, taxonomy, and classification of actinomycetes, as well as their varied bioactive metabolites recently discovered between 2015 and 2023. Additionally, we explore promising strategies to unveil and investigate new bioactive metabolites, encompassing genome mining, activation of silent genes through signal molecules, and co-cultivation approaches. By presenting this comprehensive and up-to-date review, we hope to offer a potential solution to uncover novel bioactive compounds with essential activities. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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30 pages, 6366 KiB

Open AccessReview

Phytochemistry and Biological Activities of Murraya Species

by Ricky Yohanes, Desi Harneti, Unang Supratman, Sofa Fajriah and Tarso Rudiana

Molecules 2023, 28(15), 5901; https://doi.org/10.3390/molecules28155901 - 5 Aug 2023

Cited by 2 | Viewed by 2782

Abstract

Murraya is a plant genus within the Rutaceae family comprising over 17 species, which are widely distributed in Asia, Australia, and the Pacific Islands. Furthermore, these species have been used in traditional medicine to treat fever, pain, and dysentery. Several reports have also [...] Read more.

Murraya is a plant genus within the Rutaceae family comprising over 17 species, which are widely distributed in Asia, Australia, and the Pacific Islands. Furthermore, these species have been used in traditional medicine to treat fever, pain, and dysentery. Several reports have also extensively studied the leaves, seeds, stembark, and bark of Murraya from 1965 to 2023 to explore their natural product composition. Various phytochemical studies have revealed the isolation of 413 compounds recorded, comprising coumarins, terpenoids, flavonoids, and aromatics, as well as alkaloids, which constitute the largest proportion (46.9%). These isolated compounds have long been known to exhibit different bioactivities, such as cytotoxic and anti-inflammatory properties. Cytotoxic activity has been observed against HCT 116, HeLa, HepG2, and other cell lines. Previous studies have also reported the presence of antifungal, hepatoprotective, antihyperlipidemic, antidiarrheal, and antioxidant effects. Therefore, this review provides a comprehensive overview of Murraya species, highlighting their phytochemistry, biological activities, and potential as a source of active natural compounds. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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19 pages, 3638 KiB

Open AccessReview

Potential Natural Products Regulation of Molecular Signaling Pathway in Dermal Papilla Stem Cells

by Zar Chi Soe, Zin Zin Ei, Kittichate Visuttijai and Pithi Chanvorachote

Molecules 2023, 28(14), 5517; https://doi.org/10.3390/molecules28145517 - 19 Jul 2023

Cited by 4 | Viewed by 2974

Abstract

Stem cells have demonstrated significant potential for tissue engineering and repair, anti-aging, and rejuvenation. Hair follicle stem cells can be found in the dermal papilla at the base of the follicle and the bulge region, and they have garnered increased attention because of [...] Read more.

Stem cells have demonstrated significant potential for tissue engineering and repair, anti-aging, and rejuvenation. Hair follicle stem cells can be found in the dermal papilla at the base of the follicle and the bulge region, and they have garnered increased attention because of their potential to regenerate hair as well as their application for tissue repair. In recent years, these cells have been shown to affect hair restoration and prevent hair loss. These stem cells are endowed with mesenchymal characteristics and exhibit self-renewal and can differentiate into diverse cell types. As research in this field continues, it is probable that insights regarding stem cell maintenance, as well as their self-renewal and differentiation abilities, will benefit the application of these cells. In addition, an in-depth discussion is required regarding the molecular basis of cellular signaling and the influence of nature-derived compounds in stimulating the stemness properties of dermal papilla stem cells. This review summarizes (i) the potential of the mesenchymal cells component of the hair follicle as a target for drug action; (ii) the molecular mechanism of dermal papilla stem cells for maintenance of their stem cell function; and (iii) the positive effects of the natural product compounds in stimulating stemness in dermal papilla stem cells. Together, these insights may help facilitate the development of novel effective hair loss prevention and treatment. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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18 pages, 1852 KiB

Open AccessReview

Scutellaria baicalensis Georgi and Their Natural Flavonoid Compounds in the Treatment of Ovarian Cancer: A Review

by Jiaying Cai, Qichao Hu, Zhelin He, Xiaoyan Chen, Jian Wang, Xiang Yin, Xiao Ma and Jinhao Zeng

Molecules 2023, 28(13), 5082; https://doi.org/10.3390/molecules28135082 - 29 Jun 2023

Cited by 10 | Viewed by 2878

Abstract

Ovarian cancer (OC) is one of the most common types of cancer in women with a high mortality rate, and the treatment of OC is prone to high recurrence rates and side effects. Scutellaria baicalensis (SB) is a herbal medicine with good anti-cancer [...] Read more.

Ovarian cancer (OC) is one of the most common types of cancer in women with a high mortality rate, and the treatment of OC is prone to high recurrence rates and side effects. Scutellaria baicalensis (SB) is a herbal medicine with good anti-cancer activity, and several studies have shown that SB and its flavonoids have some anti-OC properties. This paper elucidated the common pathogenesis of OC, including cell proliferation and cell cycle regulation, cell invasion and metastasis, apoptosis and autophagy, drug resistance and angiogenesis. The mechanisms of SB and its flavonoids, wogonin, baicalein, baicalin, Oroxylin A, and scutellarein, in the treatment of OC, are revealed, such as wogonin inhibits proliferation, induces apoptosis, inhibits invasion and metastasis, and increases the cytotoxicity of the drug. Baicalein also inhibits vascular endothelial growth factor (VEGF) expression etc. Analyzing their advantages and disadvantages in treating OC provides a new perspective on the role of SB and its flavonoids in OC treatment. It serves as a resource for future OC research and development. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 2313 KiB

Open AccessReview

The Potential of Magnolia spp. in the Production of Alternative Pest Control Substances

by Juana Valeria Hernandez-Rocha and Suria Gisela Vásquez-Morales

Molecules 2023, 28(12), 4681; https://doi.org/10.3390/molecules28124681 - 9 Jun 2023

Cited by 1 | Viewed by 2078

Abstract

The irrational use of synthetic pesticides in agriculture has had negative impacts on ecosystems and contributed to environmental pollution. Botanical pesticides offer a clean biotechnological alternative to meet the agricultural challenges posed by pests and arthropods. This article proposes the use of fruit [...] Read more.

The irrational use of synthetic pesticides in agriculture has had negative impacts on ecosystems and contributed to environmental pollution. Botanical pesticides offer a clean biotechnological alternative to meet the agricultural challenges posed by pests and arthropods. This article proposes the use of fruit structures (fruit, peel, seed, and sarcotesta) of several Magnolia species as biopesticides. The potential of extracts, essential oils, and secondary metabolites of these structures for pest control is described. From 11 Magnolia species, 277 natural compounds were obtained, 68.7% of which were terpenoids, phenolic compounds, and alkaloids. Finally, the importance of a correct management of Magnolia species to ensure their sustainable use and conservation is stressed. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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17 pages, 1451 KiB

Open AccessReview

Anticancer Potentials of the Lignan Magnolin: A Systematic Review

by Md. Shimul Bhuia, Polrat Wilairatana, Raihan Chowdhury, Asraful Islam Rakib, Hossam Kamli, Ahmad Shaikh, Henrique D. M. Coutinho and Muhammad Torequl Islam

Molecules 2023, 28(9), 3671; https://doi.org/10.3390/molecules28093671 - 23 Apr 2023

Cited by 18 | Viewed by 2598

Abstract

Magnolin is a naturally occurring, multi-bioactive lignan molecule with inherent anticancer effects. This study aims to summarize the botanical origins and anticancer properties of magnolin. For this, a recent (as of March 2023) literature review was conducted using various academic search engines, including [...] Read more.

Magnolin is a naturally occurring, multi-bioactive lignan molecule with inherent anticancer effects. This study aims to summarize the botanical origins and anticancer properties of magnolin. For this, a recent (as of March 2023) literature review was conducted using various academic search engines, including PubMed, Springer Link, Wiley Online, Web of Science, Science Direct, and Google Scholar. All the currently available information about this phytochemical and its role in various cancer types has been gathered and investigated. Magnolin is a compound found in many different plants. It has been demonstrated to have anticancer activity in numerous experimental models by inhibiting the cell cycle (G1 and G2/M phase); inducing apoptosis; and causing antiinvasion, antimetastasis, and antiproliferative effects via the modulation of several pathways. In conclusion, magnolin showed robust anticancer activity against many cancer cell lines by altering several cancer signaling pathways in various non- and pre-clinical experimental models, making it a promising plant-derived chemotherapeutic option for further clinical research. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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21 pages, 1165 KiB

Open AccessReview

Phytochemical Compounds and Nanoparticles as Phytochemical Delivery Systems for Alzheimer’s Disease Management

by Saad Bakrim, Sara Aboulaghras, Naoual El Menyiy, Nasreddine El Omari, Hamza Assaggaf, Learn-Han Lee, Domenico Montesano, Monica Gallo, Gokhan Zengin, Yusra AlDhaheri and Abdelhakim Bouyahya

Molecules 2022, 27(24), 9043; https://doi.org/10.3390/molecules27249043 - 19 Dec 2022

Cited by 9 | Viewed by 4082

Abstract

Alzheimer’s disease remains one of the most widespread neurodegenerative reasons for dementia worldwide and is associated with considerable mortality and morbidity. Therefore, it has been considered a priority for research. Indeed, several risk factors are involved in the complexity of the therapeutic ways [...] Read more.

Alzheimer’s disease remains one of the most widespread neurodegenerative reasons for dementia worldwide and is associated with considerable mortality and morbidity. Therefore, it has been considered a priority for research. Indeed, several risk factors are involved in the complexity of the therapeutic ways of this pathology, including age, traumatic brain injury, genetics, exposure to aluminum, infections, diabetes, vascular diseases, hypertension, dyslipidemia, and obesity. The pathophysiology of Alzheimer’s disease is mostly associated with hyperphosphorylated protein in the neuronal cytoplasm and extracellular plaques of the insoluble β-amyloid peptide. Therefore, the management of this pathology needs the screening of drugs targeting different pathological levels, such as acetylcholinesterase (AchE), amyloid β formation, and lipoxygenase inhibitors. Among the pharmacological strategies used for the management of Alzheimer’s disease, natural drugs are considered a promising therapeutic strategy. Indeed, bioactive compounds isolated from different natural sources exhibit important anti-Alzheimer effects by their effectiveness in promoting neuroplasticity and protecting against neurodegeneration as well as neuroinflammation and oxidative stress in the brain. These effects involve different sub-cellular, cellular, and/or molecular mechanisms, such as the inhibition of acetylcholinesterase (AchE), the modulation of signaling pathways, and the inhibition of oxidative stress. Moreover, some nanoparticles were recently used as phytochemical delivery systems to improve the effects of phytochemical compounds against Alzheimer’s disease. Therefore, the present work aims to provide a comprehensive overview of the key advances concerning nano-drug delivery applications of phytochemicals for Alzheimer’s disease management. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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32 pages, 3689 KiB

Open AccessReview

High Performance Marine and Terrestrial Bioadhesives and the Biomedical Applications They Have Inspired

by James Melrose

Molecules 2022, 27(24), 8982; https://doi.org/10.3390/molecules27248982 - 16 Dec 2022

Cited by 9 | Viewed by 4051

Abstract

This study has reviewed the naturally occurring bioadhesives produced in marine and freshwater aqueous environments and in the mucinous exudates of some terrestrial animals which have remarkable properties providing adhesion under difficult environmental conditions. These bioadhesives have inspired the development of medical bioadhesives [...] Read more.

This study has reviewed the naturally occurring bioadhesives produced in marine and freshwater aqueous environments and in the mucinous exudates of some terrestrial animals which have remarkable properties providing adhesion under difficult environmental conditions. These bioadhesives have inspired the development of medical bioadhesives with impressive properties that provide an effective alternative to suturing surgical wounds improving closure and healing of wounds in technically demanding tissues such as the heart, lung and soft tissues like the brain and intestinal mucosa. The Gecko has developed a dry-adhesive system of exceptional performance and has inspired the development of new generation re-usable tapes applicable to many medical procedures. The silk of spider webs has been equally inspiring to structural engineers and materials scientists and has revealed innovative properties which have led to new generation technologies in photonics, phononics and micro-electronics in the development of wearable biosensors. Man made products designed to emulate the performance of these natural bioadhesive molecules are improving wound closure and healing of problematic lesions such as diabetic foot ulcers which are notoriously painful and have also found application in many other areas in biomedicine. Armed with information on the mechanistic properties of these impressive biomolecules major advances are expected in biomedicine, micro-electronics, photonics, materials science, artificial intelligence and robotics technology. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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24 pages, 1865 KiB

Open AccessReview

Therapeutic Importance of Kaempferol in the Treatment of Cancer through the Modulation of Cell Signalling Pathways

by Malak Yahia Qattan, Mohammad Idreesh Khan, Shudayyed Hasham Alharbi, Amit Kumar Verma, Fatimah A. Al-Saeed, Alduwish Manal Abduallah and Azza A. Al Areefy

Molecules 2022, 27(24), 8864; https://doi.org/10.3390/molecules27248864 - 13 Dec 2022

Cited by 39 | Viewed by 3939

Abstract

Plant-derived flavonoids are considered natural nontoxic chemo-preventers and have been widely studied for cancer treatment in recent decades. Mostly all flavonoid compounds show significant anti-inflammatory, anticancer and antioxidant properties. Kaempferol (Kmp) is a well-studied compound and exhibits remarkable anticancer and antioxidant potential. Kmp [...] Read more.

Plant-derived flavonoids are considered natural nontoxic chemo-preventers and have been widely studied for cancer treatment in recent decades. Mostly all flavonoid compounds show significant anti-inflammatory, anticancer and antioxidant properties. Kaempferol (Kmp) is a well-studied compound and exhibits remarkable anticancer and antioxidant potential. Kmp can regulate various cancer-related processes and activities such as cell cycle, oxidative stress, apoptosis, proliferation, metastasis, and angiogenesis. The anti-cancer properties of Kmp primarily occur via modulation of apoptosis, MAPK/ERK1/2, P13K/Akt/mTOR, vascular endothelial growth factor (VEGF) signalling pathways. The anti-cancer property of Kmp has been recognized in several in-vivo and in-vitro studies which also includes numerous cell lines and animal models. This flavonoid possesses toxic activities against only cancer cells and have restricted toxicity on healthy cells. In this review, we present extensive research investigations about the therapeutic potential of Kmp in the management of different types of cancers. The anti-cancer properties of Kmp are discussed by concentration on its capability to target molecular-signalling pathway such as VEGF, STAT, p53, NF-κB and PI3K-AKT signalling pathways. The anti-cancer property of Kmf has gained a lot of attention, but the accurate action mechanism remains unclear. However, this natural compound has a great pharmacological capability and is now considered to be an alternative cancer treatment. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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24 pages, 2022 KiB

Open AccessReview

Pharmacological and Clinical Efficacy of Picrorhiza kurroa and Its Secondary Metabolites: A Comprehensive Review

by Tahani M. Almeleebia, Abdulrhman Alsayari and Shadma Wahab

Molecules 2022, 27(23), 8316; https://doi.org/10.3390/molecules27238316 - 29 Nov 2022

Cited by 17 | Viewed by 6797

Abstract

Traditional remedies for the treatment of various ailments are gaining popularity. Traditionally, one of the most valuable therapeutic herbs has been Picrorhiza kurroa Royle ex Benth. Traditional and folk uses of P. kurroa include chronic constipation, skin-related problems, burning sensation, chronic reoccurring fever, [...] Read more.

Traditional remedies for the treatment of various ailments are gaining popularity. Traditionally, one of the most valuable therapeutic herbs has been Picrorhiza kurroa Royle ex Benth. Traditional and folk uses of P. kurroa include chronic constipation, skin-related problems, burning sensation, chronic reoccurring fever, jaundice, heart problems, breathing, digestion, allergy, tuberculosis, blood-related problems, prediabetes and obesity, laxative, cholagogue, and liver stimulatory. Phytoconstituents such as glycosides, alkaloids, cucurbitacins, iridoids, phenolics, and terpenes in P. kurroa have shown promising pharmacological potential. In order to uncover novel compounds that may cure chronic illnesses, such as cardiovascular, diabetes, cancer, respiratory, and hepatoprotective diseases, the screening of P. kurroa is essential. This study comprehensively evaluated the ethnopharmacological efficacy, phytochemistry, pharmacological activity, dose, and toxicity of P. kurroa. This review provides comprehensive insights into this traditional medication for future research and therapeutic application. The purpose of this review article was to determine the pharmacological effects of P. kurroa on a variety of disorders. P. kurroa may be a natural alternative to the standard treatment for eradicating newly evolving diseases. This study is intended as a resource for future fundamental and clinical investigations. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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20 pages, 1066 KiB

Open AccessReview

Revisiting the Nutritional, Chemical and Biological Potential of Cajanus cajan (L.) Millsp.

by Baby Gargi, Prabhakar Semwal, Shabaaz Begum Jameel Pasha, Pooja Singh, Sakshi Painuli, Ashish Thapliyal and Natália Cruz-Martins

Molecules 2022, 27(20), 6877; https://doi.org/10.3390/molecules27206877 - 13 Oct 2022

Cited by 13 | Viewed by 4833

Abstract

The genus Cajanus (Family: Fabaceae) consists of approximately 37 species, and Cajanus cajan (C. cajan) is a significant member of the genus. It is a commercial legume crop widely grown in sub-tropical and semi-arid tropical areas of the world. C. cajan [...] Read more.

The genus Cajanus (Family: Fabaceae) consists of approximately 37 species, and Cajanus cajan (C. cajan) is a significant member of the genus. It is a commercial legume crop widely grown in sub-tropical and semi-arid tropical areas of the world. C. cajan is well known for its folk medicinal uses to treat various disorders, such as toothache, dizziness, diabetes, stomachache, female ailments and chronic infections. These properties have been linked to the presence of several value-added nutritional and bioactive components. Different solvent extracts from C.cajan (leaves, root, stem and seeds) have been evaluated for their phytochemical and biological activities, namely antioxidant, antimicrobial, antidiabetic, neuroprotective, and anti-inflammatory effects. Taken together, and considering the prominent nutraceutical and therapeutic properties of C. cajan, this review article focuses on the important details including ethnomedicinal uses, chemical composition, biological applications and some other medicinal aspects related to C.cajan nutraceutical and pharmacological applications. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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22 pages, 421 KiB

Open AccessReview

A Review of Bioactive Compounds and Antioxidant Activity Properties of Piper Species

by Nono Carsono, Sefren Geiner Tumilaar, Dikdik Kurnia, Diding Latipudin and Mieke Hermiawati Satari

Molecules 2022, 27(19), 6774; https://doi.org/10.3390/molecules27196774 - 10 Oct 2022

Cited by 18 | Viewed by 4472

Abstract

Antioxidants are compounds that are able to inhibit the negative effects that come from free radicals. The phenomenon of imbalanced antioxidant production and the accumulation of free radicals in cells and tissues can cause oxidative stress. Excessive free radicals that enter the body [...] Read more.

Antioxidants are compounds that are able to inhibit the negative effects that come from free radicals. The phenomenon of imbalanced antioxidant production and the accumulation of free radicals in cells and tissues can cause oxidative stress. Excessive free radicals that enter the body cannot be warded off by endogenous antioxidant compounds so that the required antioxidant compounds can come from the outside, which helps in the performance of endogenous antioxidants. Antioxidants that come from outside consist of synthetic and natural antioxidants; however, synthetic antioxidants are not an option because they have toxic and carcinogenic effects. Therefore, the use of natural ingredients is an alternative method that is needed to create a new natural antioxidant compound. Piper species are being considered as possible medicinal plants for the development of new sources of antioxidants. Several studies have been carried out starting from the extract levels, fractions, and compounds of the Piper species, which showed good antioxidant activity. Currently, some of these plants are being used as ingredients in traditional medicines to treat allergies, toothaches, and coughs. This review examines the distribution, botanical data, pharmacology, especially antioxidant activity, and the compounds contained in five Piper species, namely Piper amalago L., Piper betle L., Piper hispidum Sw., Piper longum L., and Piper umbellatum L. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

15 pages, 2140 KiB

Open AccessReview

The Norsesquiterpene Glycoside Ptaquiloside as a Poisonous, Carcinogenic Component of Certain Ferns

by János Vetter

Molecules 2022, 27(19), 6662; https://doi.org/10.3390/molecules27196662 - 7 Oct 2022

Cited by 5 | Viewed by 2388

Abstract

Previous studies related to the ptaquiloside molecule, a carcinogenic secondary metabolite known from the world of ferns, are summarised. Ptaquiloside (PTA) belongs to the group of norsesquiterpenes of the illudane type. The name illudane refers to the fungal taxa from which the first [...] Read more.

Previous studies related to the ptaquiloside molecule, a carcinogenic secondary metabolite known from the world of ferns, are summarised. Ptaquiloside (PTA) belongs to the group of norsesquiterpenes of the illudane type. The name illudane refers to the fungal taxa from which the first representatives of the molecular group were identified. Ptaquiloside occurs mainly in Pteridium fern species, although it is also known in other fern taxa. The species of the genus Pteridium are common, frequent invasive species on all continents, and PTA is formed in smaller or larger amounts in all organs of the affected species. The effects of PTA and of their derivatives on animals and humans are of great toxicological significance. Its basic chemical property is that the molecule can be transformed. First, with the loss of sugar moiety, ptaquilosine is formed, and then, under certain conditions, a dienone derivative (pteridienone) may arise. The latter can alkylate (through its cyclopropane groups) certain molecules, including DNA, in animal or human organisms. In this case, DNA adducts are formed, which can later have a carcinogenic effect through point mutations. The scope of the PTA is interdisciplinary in nature since, for example, molecules from plant biomass can enter the body of animals or humans in several ways (directly and indirectly). Due to its physico-chemical properties (excellent water solubility), PTA can get from the plant into the soil and then into different water layers. PTA molecules that enter the soil, but mainly water, undergo degradation (hydrolytic) processes, so it is very important to clarify the toxicological conditions of a given ecosystem and to estimate the possible risks caused by PTA. The toxicoses and diseases of the animal world (mainly for ruminant farm animals) caused by PTA are briefly described. The intake of PTA-containing plants as a feed source causes not only various syndromes but can also enter the milk (and meat) of animals. In connection with the toxicological safety of the food chain, it is important to investigate the transport of carcinogenic PTA metabolites between organisms in a reassuring manner and in detail. This is a global, interdisciplinary task. The present review aims to contribute to this. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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23 pages, 446 KiB

Open AccessReview

Ocimum Species: A Review on Chemical Constituents and Antibacterial Activity

by Hendra Dian Adhita Dharsono, Salsabila Aqila Putri, Dikdik Kurnia, Dudi Dudi and Mieke Hemiawati Satari

Molecules 2022, 27(19), 6350; https://doi.org/10.3390/molecules27196350 - 26 Sep 2022

Cited by 28 | Viewed by 5452

Abstract

Infection by bacteria is one of the main problems in health. The use of commercial antibiotics is still one of the treatments to overcome these problems. However, high levels of consumption lead to antibiotic resistance. Several types of antibiotics have been reported to [...] Read more.

Infection by bacteria is one of the main problems in health. The use of commercial antibiotics is still one of the treatments to overcome these problems. However, high levels of consumption lead to antibiotic resistance. Several types of antibiotics have been reported to experience resistance. One solution that can be given is the use of natural antibacterial products. There have been many studies reporting the potential antibacterial activity of the Ocimum plant. Ocimum is known to be one of the medicinal plants that have been used traditionally by local people. This plant contains components of secondary metabolites such as phenolics, flavonoids, steroids, terpenoids, and alkaloids. Therefore, in this paper, we will discuss five types of Ocimum species, namely O. americanum, O. basilicum, O. gratissimum, O. campechianum, and O. sanctum. The five species are known to contain many chemical constituents and have good antibacterial activity against several pathogenic bacteria. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

16 pages, 16143 KiB

Open AccessReview

Bioactive Natural Products for Chemical Control of Microorganisms: Scientific Prospecting (2001–2021) and Systematic Review

by Bruno Fonsêca Feitosa, Charlene Maria de Alcântara, Amanda Beatriz Sales de Lima, Adriano Sant’Ana Silva, Alfredina dos Santos Araújo, Mônica Tejo Cavalcanti, Edna Mori, Isaac Moura Araújo, Pablo Antonio Maia de Farias, Polrat Wilairatana and Henrique Douglas Melo Coutinho

Molecules 2022, 27(18), 5917; https://doi.org/10.3390/molecules27185917 - 12 Sep 2022

Cited by 9 | Viewed by 2697

Abstract

The inappropriate use of synthetic antibiotics has become a global public health problem. Therefore, the study of new alternatives for the treatment of infectious diseases is relevant and natural bioactive products are on the rise. This study conducted a scientific prospection of bioactive [...] Read more.

The inappropriate use of synthetic antibiotics has become a global public health problem. Therefore, the study of new alternatives for the treatment of infectious diseases is relevant and natural bioactive products are on the rise. This study conducted a scientific prospection of bioactive natural products with promising applications in the chemical control of microorganisms. A systematic review of the most recent articles was performed according to the following three steps: (i) eligibility assessment, (ii) screening, and (iii) inclusion of articles and information extraction. There has been an increase in the number of scientific publications on bioactive natural products for microbial control in the CAPES and SciELO databases (2001–2021). Seventeen relevant articles were included, most of which focused on extracts. Ascorbic acid, chlorogenic acid, chrysin, and quercetin were the most cited compounds. Natural products were shown to be effective in inhibiting more than 30 microorganisms. A discussion was presented on the research trends. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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14 pages, 1581 KiB

Open AccessReview

Stinging Nettle (Urtica dioica L.): Nutritional Composition, Bioactive Compounds, and Food Functional Properties

by Hari Prasad Devkota, Keshav Raj Paudel, Shristi Khanal, Ananda Baral, Nisha Panth, Anjana Adhikari-Devkota, Niraj Kumar Jha, Niranjan Das, Sachin Kumar Singh, Dinesh Kumar Chellappan, Kamal Dua and Philip M. Hansbro

Molecules 2022, 27(16), 5219; https://doi.org/10.3390/molecules27165219 - 16 Aug 2022

Cited by 48 | Viewed by 16166

Abstract

Stinging nettle (Urtica dioica L., Urticaceae) is commonly found in Asia, Africa, and Europe and has a long history of being used as food and traditional medicine. Recently, this plant is gaining attention as a highly nutritious food, where fresh leaves are [...] Read more.

Stinging nettle (Urtica dioica L., Urticaceae) is commonly found in Asia, Africa, and Europe and has a long history of being used as food and traditional medicine. Recently, this plant is gaining attention as a highly nutritious food, where fresh leaves are dried and used as powder or in other forms. Leaves are rich in many bioactive compounds. This review aims to cover the traditional uses in food and medicine, as well as its nutritional composition, including its bioactive chemical constituents and reported food functional activities. Various bioactive chemical constituents have been isolated from stinging nettle to date, such as flavonoids, phenolic acids, amino acid, carotenoids, and fatty acids. Stinging nettle extracts and its compounds, such as rutin, kaempferol, and vitamin A, are also used for their nutritional properties and as anti-inflammatory and antioxidant agents. Future studies should focus on the proper formulation and stability testing of the functional foods containing stinging nettle and their detailed activities in clinical studies. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 2439 KiB

Open AccessReview

A Review on the Extraction, Bioactivity, and Application of Tea Polysaccharides

by Jianmei Yao, Huifang Liu, Chiyu Ma, Lulu Pu, Wen Yang and Zhiwei Lei

Molecules 2022, 27(15), 4679; https://doi.org/10.3390/molecules27154679 - 22 Jul 2022

Cited by 8 | Viewed by 3195

Abstract

Tea is a non-alcoholic drink containing various active ingredients, including tea polysaccharides (TPSs). TPSs have various biological activities, such as antioxidant, anti-tumor, hypoglycemic, and anti-cancer activities. However, TPSs have a complex composition, which significantly limits the extraction and isolation methods, thus limiting their [...] Read more.

Tea is a non-alcoholic drink containing various active ingredients, including tea polysaccharides (TPSs). TPSs have various biological activities, such as antioxidant, anti-tumor, hypoglycemic, and anti-cancer activities. However, TPSs have a complex composition, which significantly limits the extraction and isolation methods, thus limiting their application. This paper provides insight into the composition, methodological techniques for isolation and extraction of the components, biological activities, and functions of TPSs, as well as their application prospects. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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12 pages, 840 KiB

Open AccessReview

The Genus Miconia Ruiz & Pav. (Melastomataceae): Ethnomedicinal Uses, Pharmacology, and Phytochemistry

by Viviane Bezerra da Silva, José Weverton Almeida-Bezerra, Adrielle Rodrigues Costa, Maria Flaviana Bezerra Morais-Braga, Maraiza Gregorio de Oliveira, Anderson Angel Vieira Pinheiro, Raimundo Samuel Leite Sampaio, José Walber Gonçalves Castro, Marcos Aurélio Figueiredo dos Santos, Valdilia Ribeiro de Alencar Ulisses, Maria Edilania da Silva Serafim Pereira, Dieferson Leandro de Souza, Bruno Melo de Alcântara, Maria Elizete Machado Generino, José Thyálisson da Costa Silva, Ademar Maia Filho, Sabrina Bezerra da Silva, Myunghan Moon, Bonglee Kim and José Galberto Martins da Costa

Molecules 2022, 27(13), 4132; https://doi.org/10.3390/molecules27134132 - 27 Jun 2022

Cited by 7 | Viewed by 2859

Abstract

Species of the genus Miconia are used in traditional medicine for the treatment of diseases, such as pain, throat infections, fever, and cold, and they used as depuratives, diuretics, and sedatives. This work reviewed studies carried out with Miconia species, highlighting its ethnomedicinal [...] Read more.

Species of the genus Miconia are used in traditional medicine for the treatment of diseases, such as pain, throat infections, fever, and cold, and they used as depuratives, diuretics, and sedatives. This work reviewed studies carried out with Miconia species, highlighting its ethnomedicinal uses and pharmacological and phytochemical potential. This information was collected in the main platforms of scientific research (PubMed, Scopus, and Web of Science). Our findings show that some of the traditional uses of Miconia are corroborated by biological and/or pharmacological assays, which demonstrated, among other properties, anti-inflammatory, analgesic, antimutagenic, antiparasitic, antioxidant, cytotoxic, and antimicrobial activities. A total of 148 chemical compounds were identified in Miconia species, with phenolic compounds being the main constituents found in the species of this genus. Such phytochemical investigations have demonstrated the potential of species belonging to this genus as a source of bioactive substances, thus reinforcing their medicinal and pharmacological importance. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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21 pages, 1202 KiB

Open AccessSystematic Review

Plectranthus Species with Anti-Inflammatory and Analgesic Potential: A Systematic Review on Ethnobotanical and Pharmacological Findings

by Maysa de Oliveira Barbosa, Polrat Wilairatana, Giovana Mendes de Lacerda Leite, Gyllyandeson de Araújo Delmondes, Lucas Yure Santos da Silva, Silvio Caetano Alves Júnior, Lindaiane Bezerra Rodrigues Dantas, Daniel Souza Bezerra, Izabel Cristina Santiago Lemos de Beltrão, Diógenes de Queiroz Dias, Jaime Ribeiro-Filho, Cícero Francisco Bezerra Felipe, Henrique Douglas Melo Coutinho, Irwin Rose Alencar de Menezes and Marta Regina Kerntopf Mendonça

Molecules 2023, 28(15), 5653; https://doi.org/10.3390/molecules28155653 - 26 Jul 2023

Cited by 5 | Viewed by 3127

Abstract

The use of medicinal plants to treat inflammatory conditions and painful processes has attracted the attention of scientists and health professionals due to the evidence that natural products can promote significant therapeutic benefits associated with fewer adverse effects compared to conventional anti-inflammatory drugs. [...] Read more.

The use of medicinal plants to treat inflammatory conditions and painful processes has attracted the attention of scientists and health professionals due to the evidence that natural products can promote significant therapeutic benefits associated with fewer adverse effects compared to conventional anti-inflammatory drugs. The genus Plectranthus is composed of various plants with pharmacological potential, which are used to treat various diseases in traditional communities worldwide. The present study systematically reviewed Plectranthus species with anti-inflammatory and analgesic potential. To this end, a systematic review was conducted following the Preferred Reporting Items for Systematic Reviews and Meta-Analyses (PRISMA) protocol. The search was conducted on the following databases: PubMed, ScienceDirect, SciVerse Scopus, and Web of Science. Different combinations of search terms were used to ensure more excellent article coverage. After the selection, a total of 45 articles were included in this review. This study identified twelve Plectranthus species indicated for the treatment of different inflammatory conditions, such as wounds, fever, bronchitis, abscess, asthma, hepatitis, labyrinthitis, tonsillitis, and uterine inflammation. The indications for pain conditions included headache, sore throat, heartburn, menstrual cramp, colic, toothache, stomachache, migraine, chest pain, abdominal pain, local pain, labor pain, and recurring pain. Among the listed species, ten plants were found to be used according to traditional knowledge, although only four of them have been experimentally studied. When assessing the methodological quality of preclinical in vivo assays, most items presented a risk of bias. The SR results revealed the existence of different Plectranthus species used to treat inflammation and pain. The results of this systematic review indicate that Plectranthus species have the potential to be used in the treatment of diseases with an inflammatory component, as well as in the management of pain. However, given the risk of biases, the experimental analysis of these species through preclinical testing is crucial for their safe and effective use. Full article

(This article belongs to the Special Issue Advances in Natural Products and Their Biological Activities)

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