Molecules

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20 pages, 676 KiB

Open AccessArticle

Characterization of Triadica sebifera (L.) Small Extracts, Antifeedant Activities of Extracts, Fractions, Seed Oil and Isolated Compounds against Plutella xylostella (L.) and Their Effect on Detoxification Enzymes

by Shudh Kirti Dolma and S. G. Eswara Reddy

Molecules 2022, 27(19), 6239; https://doi.org/10.3390/molecules27196239 - 22 Sep 2022

Cited by 4 | Viewed by 1967

Abstract

Plutella xylostella L. is one of the world’s major pests of cruciferous crops. The indiscriminate use of synthetic insecticides has led to insecticide resistance and resurgence, and has been harmful to non-target organisms and the environment. Botanical insecticides are the best alternatives to [...] Read more.

Plutella xylostella L. is one of the world’s major pests of cruciferous crops. The indiscriminate use of synthetic insecticides has led to insecticide resistance and resurgence, and has been harmful to non-target organisms and the environment. Botanical insecticides are the best alternatives to synthetic pesticides for the management of pests in organic agriculture and integrated management. T. sebifera is an invasive species and has good potential as an insecticide due to the availability of plant material in some parts of India. The antifeedant activities of T. sebifera have not been reported against P. xylostella and other lepidopteron insects to date. Therefore, the current study targeted the characterization of leaf and bark extracts, feeding deterrence, synergistic and detoxification enzyme activities of leaf/bark ethanolic extracts/fractions, seed oil, and isolated compounds. UHPLC-QTOF-IMS analysis showed that shikimic acid, xanthoxylin, quercetin, kaempferol, methyl gallate, and stigmasterol are common metabolites identified in leaf and bark extracts. The combination of seed oil with bark extract showed higher deterrence (DC₅₀ = 317.10 mg/L) as compared to leaf/bark extracts alone. Gallic acid showed higher deterrence (67.48%) than kaempferol and quercetin. The n-butanol fraction of bark was more repellent (RC₅₀ = 414.61 mg/L). Based on DC₅₀, the seed oil with leaf extract (1:1 ratio) alone with choice and seed oil with leaf and bark extract without choice showed synergistic interaction, but seed oil with bark extract with choice showed additive interaction. The ethanol extract of leaf, bark, and seed oil inhibited GST and AChE in P. xylostella. The leaf extract and seed oil or their combinations may be recommended as antifeedants to reduce damage by P. xylostella based on persistence, antifeedant, phytotoxicity, safety to predators/parasitoids, etc., under field conditions. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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9 pages, 922 KiB

Open AccessArticle

Simultaneous UHPLC-MS Quantification of Catechins and Untargeted Metabolomic Profiling for Proof-of-Concept Authenticity Determination of Maytenus ssp. Samples

by Rodolfo Santos Duarte, Elisa Ribeiro Miranda Antunes and Alexandra Christine Helena Frankland Sawaya

Molecules 2022, 27(17), 5520; https://doi.org/10.3390/molecules27175520 - 27 Aug 2022

Viewed by 1425

Abstract

Due to the widespread use of Maytenus ilicifolia leaves in the treatment of gastric ulcers, herbal medicines derived from such species are distributed by the national health system in Brazil. A related species, Maytenus aquifolium, is also used for the same disorders, [...] Read more.

Due to the widespread use of Maytenus ilicifolia leaves in the treatment of gastric ulcers, herbal medicines derived from such species are distributed by the national health system in Brazil. A related species, Maytenus aquifolium, is also used for the same disorders, and both are popularly known as Espinheira-santa. Due to their popular use, the quality and efficiency of the herbal medicines derived from these species is an important public health issue. The purpose of this study was to develop and test an analytical method that could quantify the content of catechin and epicatechin in dry Maytenus spp. leaves and simultaneously obtain their chemical profile to determine authenticity of the leaf samples. Ultra-high performance liquid chromatography coupled to mass spectrometry (UHPLC-MS) was used to quantify these isomers, in the selected ion monitoring (SIM) mode, while simultaneously analyzing the extract in full-scan mode. This approach was successfully applied to the analysis of commercial and authentic samples of Maytenus spp. Fewer than half the samples presented the minimum epicatechin content of 2.8 mg per g of dry leaf mass, as specified in the 6th Brazilian Pharmacopoeia (2019) for M. ilicifolia. Furthermore, by using untargeted metabolomics, it was observed that the chemical profile of most the samples was not compatible with M. ilicifolia leaves, indicating the need for stricter quality control of this material. The method described herein could be used for this control; moreover, its concept could be adapted and used for an ample variety of medicinal plant products. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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18 pages, 12745 KiB

Open AccessArticle

Molecular Dereplication and In Vitro and In Silico Pharmacological Evaluation of Coriandrum sativum against Neuroblastoma Cells

by Maria Cristina Marcucci, Carlos Rocha Oliveira, Daniel Spindola, Alyne A. Antunes, Leila Y. K. Santana, Victor Cavalaro, Isabelle B. Costa, Ana C. de Carvalho, Thiago A. M. Veiga, Livia S. Medeiros, Lucas dos Santos Zamarioli, Carolina P. Gonçalves, Milena F. Santos, Simone S. Grecco, Vanessa Y. Suzuki, Lydia Masako Ferreira and Daniel M. Garcia

Molecules 2022, 27(17), 5389; https://doi.org/10.3390/molecules27175389 - 24 Aug 2022

Cited by 2 | Viewed by 2315

Abstract

The aim of this study was to investigate the cytotoxic activity of the Coriandrum sativum (C. sativum) ethanolic extract (CSEE) in neuroblastoma cells, chemically characterize the compounds present in the CSEE, and predict the molecular interactions and properties of ADME. Thus, [...] Read more.

The aim of this study was to investigate the cytotoxic activity of the Coriandrum sativum (C. sativum) ethanolic extract (CSEE) in neuroblastoma cells, chemically characterize the compounds present in the CSEE, and predict the molecular interactions and properties of ADME. Thus, after obtaining the CSEE and performing its chemical characterization through dereplication methods using UPLC/DAD-ESI/HRMS/MS, PM6 methods and the SwissADME drug design platform were used in order to predict molecular interactions and ADME properties. The CSEE was tested for 24 h in neuroblastoma cells to the establishment of the IC50 dose. Then, the cell death was evaluated, using annexin-PI, as well as the activity of the effector caspase 3, and the protein and mRNA levels of Bax and Bcl-2 were analyzed by ELISA and RT-PCR, respectively. By UHPLC/DAD/HRMS-MS/MS analysis, the CSEE showed a high content of isocoumarins-dihydrocoriandrin, coriandrin, and coriandrones A and B, as well as nitrogenated compounds (adenine, adenosine, and tryptophan). Flavonoids (apigenin, hyperoside, and rutin), phospholipids (PAF C-16 and LysoPC (16:0)), and acylglicerol were also identified in lower amount as important compounds with antioxidant activity. The in silico approach results showed that the compounds 1 to 6, which are found mostly in the C. sativum extract, obey the “Five Rules” of Lipinski, suggesting a good pharmacokinetic activity of these compounds when administered orally. The IC50 dose of CSEE (20 µg/mL) inhibited cell proliferation and promoted cell death by the accumulation of cleaved caspase-3 and the externalization of phosphatidylserine. Furthermore, CSEE decreased Bcl-2 and increased Bax, both protein and mRNA levels, suggesting an apoptotic mechanism. CSEE presents cytotoxic effects, promoting cell death. In addition to the promising results predicted through the in silico approach for all compounds, the compound 6 showed the best results in relation to stability due to its GAP value. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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26 pages, 3701 KiB

Open AccessArticle

Bridging the Chemical Profiles and Biological Effects of Spathodea campanulata Extracts: A New Contribution on the Road from Natural Treasure to Pharmacy Shelves

by Łukasz Świątek, Elwira Sieniawska, Kouadio Ibrahime Sinan, Gokhan Zengin, Abdullahi Ibrahim Uba, Kouadio Bene, Magdalena Maciejewska-Turska, Barbara Rajtar, Małgorzata Polz-Dacewicz and Abdurrahman Aktumsek

Molecules 2022, 27(15), 4694; https://doi.org/10.3390/molecules27154694 - 22 Jul 2022

Cited by 5 | Viewed by 2815

Abstract

Spathodea campanulata is an important medicinal plant with traditional uses in the tropical zone. In the current work, we aimed to determine the chemical profiles and biological effects of extracts (methanolic and infusion (water)) from the leaves and stem bark of S. campanulata [...] Read more.

Spathodea campanulata is an important medicinal plant with traditional uses in the tropical zone. In the current work, we aimed to determine the chemical profiles and biological effects of extracts (methanolic and infusion (water)) from the leaves and stem bark of S. campanulata. The chemical components of the tested extracts were identified using LC-ESI-QTOF-MS. Biological effects were tested in terms of antioxidant (radical scavenging, reducing power, and metal chelating), enzyme inhibitory (cholinesterase, amylase, glucosidase, and tyrosinase), antineoplastic, and antiviral activities. Fifty-seven components were identified in the tested extracts, including iridoids, flavonoids, and phenolic acids as the main constituents. In general, the leaves-MeOH extract was the most active in the antioxidant assays (DPPH, ABTS, CUPRAC, FRAP, metal chelating, and phosphomolybdenum). Antineoplastic effects were tested in normal (VERO cell line) and cancer cell lines (FaDu, HeLa, and RKO). The leaf infusion, as well as the extracts obtained from stem bark, showed antineoplastic activity (CC₅₀ 119.03–222.07 µg/mL). Antiviral effects were tested against HHV-1 and CVB3, and the leaf methanolic extract (500 µg/mL) exerted antiviral activity towards HHV-1, inhibiting the viral-induced cytopathic effect and reducing the viral infectious titre by 5.11 log and viral load by 1.45 log. In addition, molecular docking was performed to understand the interactions between selected chemical components and viral targets (HSV-1 DNA polymerase, HSV-1 protease, and HSV-1 thymidine kinase). The results presented suggest that S. campanulata may be a bright spot in moving from natural sources to industrial applications, including novel drugs, cosmeceuticals, and nutraceuticals. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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10 pages, 760 KiB

Open AccessArticle

Effects of Plant Elicitors on Growth and Gypenosides Biosynthesis in Cell Culture of Giao co lam (Gynostemma pentaphyllum)

by Hoang Tan Quang, Pham Thi Diem Thi, Dang Ngoc Sang, Tran Thi Ngoc Tram, Nguyen Duc Huy, Tran Quoc Dung and Quach Thi Thu The

Molecules 2022, 27(9), 2972; https://doi.org/10.3390/molecules27092972 - 6 May 2022

Cited by 5 | Viewed by 2959

Abstract

Giao co lam (Gynostemma pentaphyllum (Thunb.) Makino) is used in Northeast and Southeast Asia countries for the treatment of various diseases, including hepatitis, diabetes, and cardiovascular disease. G. pentaphyllum saponins (gypenosides) are the major components responsible for the pharmacological activities. In this [...] Read more.

Giao co lam (Gynostemma pentaphyllum (Thunb.) Makino) is used in Northeast and Southeast Asia countries for the treatment of various diseases, including hepatitis, diabetes, and cardiovascular disease. G. pentaphyllum saponins (gypenosides) are the major components responsible for the pharmacological activities. In this study, different concentrations of abiotic (25–200 μM methyl jasmonate-MeJA and salicylic acid-SA) or biotic elicitors (1–5 g/L yeast extract-YE and Fusarium biomass) were used as plant elicitors, in order to investigate their influences on cell growth and gypenosides accumulation in G. pentaphyllum suspension cells. Suspension cells were grown on a MS medium containing 2.0 mg/L KIN and 0.5 mg/L IBA, with initial inoculum sizes of 3 g and shaking speeds of 120 rpm for 18 days. Gypenoside and Rb1 contents were measured by colorimetric and HPLC methods. Among three elicitors, SA was suitable for gypenosides accumulation in individual treatment. The cell biomass had the same values in elicitated and control suspension cells. Gypenosides content in cells treated with 100 μM salicylic acid after 6 days of culture reached a maximum value of 79.721 mg gypenoside/g dry biomass (including 0.093 mg ginsenoside Rb1/mg dry weight), which was 2.18-folds higher than that of the natural product. The elicitation promises an efficiency strategy for the production gypenosides in Gynostemma pentaphyllum suspension cells. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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12 pages, 881 KiB

Open AccessArticle

Powerful Antioxidants and Cytotoxic Activities of the Methanol Extracts from Eight Soybean Cultivars

by Mohamed A. Abd Elhamid, Abd Elrahman S. Mandour, Tarek A. Ismail, Ahmed M. Al-Zohairy, Sanaa Almowallad, Leena S. Alqahtani and Ali Osman

Molecules 2022, 27(9), 2895; https://doi.org/10.3390/molecules27092895 - 1 May 2022

Cited by 6 | Viewed by 2370

Abstract

In the present study, the chemical composition and total phenolic (TPC) and total flavonoid contents (TFC) of eight soybean cultivars (Giza 21, Giza 22, Giza 35, Giza 111, Giza 82, Giza 83, Crawford, and Holliday) were estimated. Moreover, antioxidant activity and in vitro [...] Read more.

In the present study, the chemical composition and total phenolic (TPC) and total flavonoid contents (TFC) of eight soybean cultivars (Giza 21, Giza 22, Giza 35, Giza 111, Giza 82, Giza 83, Crawford, and Holliday) were estimated. Moreover, antioxidant activity and in vitro cytotoxic activities against HepG-2 and MCF-7 were evaluated. Giza 21, Giza 111, and Crawford cultivars recorded higher than 40% crude protein. The analysis revealed that TPC values in seed extracts ranged from 10.5 mg GAE/g extract in Giza 35 to 6.4 mg GAE/g extract in Giza 22. TFC varied from 1.20 mg QE/g extract in Giza 111 to 0.55 mg QE/g extract in Crawford. Giza 35 exhibited the highest content of genistein and daidzein and the highest free radical scavenging activity (61.833%). The results of the MTT assay demonstrated that the soybean methanolic extracts inhibited the proliferation of HepG-2 and MCF-7 cells in a dose-dependent manner. Giza 35 exhibited the highest cytotoxic activity. In conclusion, Giza 35 cultivar recorded the highest TPC and TFC values and antioxidant and cytotoxic activities. Therefore, this cultivar can be used as a source for the production of pharmaceutical and medicinal products rather than as a nutritional source of protein. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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15 pages, 1316 KiB

Open AccessArticle

Aloe arborescens: In Vitro Screening of Genotoxicity, Effective Inhibition of Enzyme Characteristics for Disease Etiology, and Microbiological Activity

by Kamil Pawłowicz, Szymon Sip, Tomasz Plech, Barbara Kaproń, Joanna Kobus-Cisowska and Judyta Cielecka-Piontek

Molecules 2022, 27(7), 2323; https://doi.org/10.3390/molecules27072323 - 3 Apr 2022

Cited by 5 | Viewed by 2900

Abstract

The present study assessed the genotoxicity, the possibility of inhibiting selected enzymes, and the microbial activity of lyophilisate from 3-year-old A. arborescens leaves obtained from controlled crops. The lyophilisate from 3-year-old A. arborescens leaves was standardized for aloin A and aloenin A content. [...] Read more.

The present study assessed the genotoxicity, the possibility of inhibiting selected enzymes, and the microbial activity of lyophilisate from 3-year-old A. arborescens leaves obtained from controlled crops. The lyophilisate from 3-year-old A. arborescens leaves was standardized for aloin A and aloenin A content. Moreover, concentrations of polyphenolic compounds and phenolic acids were determined. The first stage of the research was to determine genotoxicity using the comet test, which confirmed the safety of A. arborescens. Assays of enzymatic inhibition were performed for hyaluronidase (IC50 = 713.24 ± 41.79 µg/mL), α-glucosidase (IC50 = 598.35 ± 12.58 µg/mL), acetylcholinesterase and butyrylcholinesterase (1.16 vs. 0.34 µM of eserine/g d.m., respectively). The next stage of the research was to determine the ability of the healing properties using the scratch test, which showed a positive response using the extract. Microbial activity was evaluated and obtained against Gram-negative and Gram-positive bacteria and yeasts. We concluded that A. arborescens leaf gel meets the important conditions for plant raw materials to obtain semi-solid forms of herbal medicinal products. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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17 pages, 2413 KiB

Open AccessArticle

Antibacterial Activity of Chinese Red Propolis against Staphylococcus aureus and MRSA

by Wenwen Zhang, Gomez Escalada Margarita, Di Wu, Wenqin Yuan, Sha Yan, Suzhen Qi, Xiaofeng Xue, Kai Wang and Liming Wu

Molecules 2022, 27(5), 1693; https://doi.org/10.3390/molecules27051693 - 4 Mar 2022

Cited by 17 | Viewed by 3891

Abstract

The antibacterial activity of propolis has long been of great interest, and the chemical composition of propolis is directly dependent on its source. We recently obtained a type of propolis from China with a red color. Firstly, the antibacterial properties of this unusual [...] Read more.

The antibacterial activity of propolis has long been of great interest, and the chemical composition of propolis is directly dependent on its source. We recently obtained a type of propolis from China with a red color. Firstly, the antibacterial properties of this unusual propolis were determined against Staphylococcus aureus and methicillin-resistant Staphylococcus aureus (MRSA). Studies on its composition identified and quantified 14 main polyphenols of Chinese red propolis extracts (RPE); quantification was carried out using liquid chromatography triple quadrupole tandem mass spectrometry (LC-QQQ-MS/MS) and RPE was found to be rich in pinobanksin, pinobanksin-3-acetate, and chrysin. In vitro investigations of its antibacterial activity revealed that its activity against S. aureus and MRSA is due to disruption of the cell wall and cell membrane, which then inhibits bacterial growth. Despite its similar antibacterial activities against S. aureus and MRSA, metabolomic analysis further revealed the effects of RPE on bacteria metabolism were different. The untargeted metabolomic results showed that a total of 7 metabolites in 12 metabolic pathways had significant changes (Fold change > 2, p < 0.05 *) after RPE treatment in S. aureus, while 11 metabolites in 9 metabolic pathways had significant changes (Fold change > 2, p < 0.05 *) after RPE treated on MRSA. Furthermore, RPE downregulated several specific genes related to bacterial biofilm formation, autolysis, cell wall synthesis, and bacterial virulence in MRSA. In conclusion, the data obtained indicate that RPE may be a promising therapeutic agent against S. aureus and MRSA. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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15 pages, 1626 KiB

Open AccessArticle

Miodesin^TM Positively Modulates the Immune Response in Endometrial and Vaginal Cells

by Carlos Rocha Oliveira, Hudson Polonini, Maria Cristina Marcucci and Rodolfo P. Vieira

Molecules 2022, 27(3), 782; https://doi.org/10.3390/molecules27030782 - 25 Jan 2022

Cited by 3 | Viewed by 3956

Abstract

Endometriosis presents high prevalence and its physiopathology involves hyperactivation of endometrial and vaginal cells, especially by bacteria. The disease has no cure and therapies aiming to inhibit its development are highly desirable. Therefore, this study investigated whether Miodesin^TM (10 µg/mL = IC [...] Read more.

Endometriosis presents high prevalence and its physiopathology involves hyperactivation of endometrial and vaginal cells, especially by bacteria. The disease has no cure and therapies aiming to inhibit its development are highly desirable. Therefore, this study investigated whether Miodesin^TM (10 µg/mL = IC₈₀; 200 µg/mL = IC₅₀), a natural compound constituted by Uncaria tomentosa, Endopleura uchi, and astaxanthin, could exert anti-inflammatory and anti-proliferative effects against Lipopolysaccharides (LPS) stimulation in endometrial and Candida albicans vaginal cell lines. VK2 E6/E7 (vaginal) and KLE (epithelial) cell lines were stimulated with Candida albicans (1 × 10⁷ to 5 × 10⁷/mL) and LPS (1 μg/mL), respectively. Miodesin^TM inhibited mRNA expression for Nuclear factor kappa B (NF-κB), ciclo-oxigenase 1 (COX-1), and phospholipase A2 (PLA2), beyond the C–C motif chemokine ligand 2 (CCL2), CCL3, and CCL5 in VK2 E6/E7 cells (p < 0.05). In addition, the inhibitory effects of both doses of Miodesin^TM (10 µg/mL and 200 µg/mL) resulted in reduced secretion of interleukin-1β (IL-1β), IL-6, IL-8, tumor necrosis factor α (TNF-α) (24 h, 48 h, and 72 h) and CCL2, CCL3, and CLL5 (p < 0.05) by VK2 E6/E7 cells. In the same way, COX-1 Miodesin^TM inhibited LPS-induced hyperactivation of KLE cells, as demonstrated by reduced secretion of IL-1β, IL-6, IL-8, TNF-α (24 h, 48 h, and 72 h) and CCL2, CCL3, and CLL5 (p < 0.05). Furthermore, Miodesin^TM also inhibited mRNA expression and secretion of matrix metalloproteinase-2 (MMP-2), MMP-9, and vascular endothelial growth factor (VEGF), which are key regulators of invasion of endometrial cells. Thus, the study concludes that Miodesin^TM presents beneficial effects in the context of endometriosis, positively affecting the inflammatory and proliferative response. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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14 pages, 4813 KiB

Open AccessArticle

Protective Effects of L-Theanine on IPEC-J2 Cells Growth Inhibition Induced by Dextran Sulfate Sodium via p53 Signaling Pathway

by Longlin Zhang, Mengmeng Ma, Zhengyi Li, Haihan Zhang, Xi He and Zehe Song

Molecules 2021, 26(22), 7002; https://doi.org/10.3390/molecules26227002 - 19 Nov 2021

Cited by 3 | Viewed by 2311

Abstract

L-theanine is a nonprotein amino acid found in tea leaves and has been widely used as a safe food additive in beverages or foods because of its varied bioactivities. The aim of this study was to reveal the in vitro gastrointestinal protective effects [...] Read more.

L-theanine is a nonprotein amino acid found in tea leaves and has been widely used as a safe food additive in beverages or foods because of its varied bioactivities. The aim of this study was to reveal the in vitro gastrointestinal protective effects of L-theanine in DSS-induced intestinal porcine enterocyte (IPEC-J2) cell models using molecular and metabolic methods. Results showed that 2.5% dextran sulfate sodium (DSS) treatment inhibited the cell proliferation of IPEC-J2 and blocked the normal operation of the cell cycle, while L-theanine pretreatment significantly preserved these trends to exert protective effects. L-theanine pre-treatment also up-regulated the EGF, CDC2, FGF2, Rb genes and down-regulated p53, p21 proliferation-related mRNA expression in DSS-treated cells, in accompany with p53 signaling pathway inhibition. Meanwhile, metabolomics analysis revealed that L-theanine and DSS treated IPEC-J2 cells have different metabolomic profiles, with significant changes in the key metabolites involved in pyrimidine metabolism and amino acid metabolism, which play an important role in nucleotide metabolism. In summary, L-theanine has a beneficial protection in DSS-induced IPEC-J2 cells via promoting proliferation and regulating metabolism disorders. Full article

(This article belongs to the Special Issue Characterization, Properties and Applications of Natural Products)

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