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25 pages, 11008 KiB

Open AccessArticle

Enrichment Extraction and Activity Study of the Different Varieties of Hericium erinaceus against HCT-8 Colon Cancer Cells

by Zhongrui Cao, Zhijun Zhang, Dongsheng Wei, Mingyu Guo, Shufang Li, Hanyuan Cui, Yue Zhang, Yuwei Zhang and Xiaoming Chen

Molecules 2023, 28(17), 6288; https://doi.org/10.3390/molecules28176288 - 28 Aug 2023

Cited by 1 | Viewed by 2082

Abstract

Hericium erinaceus (HE), a widely utilized natural remedy and dietary source, has garnered significant attention for its therapeutic potential in various diseases. In this study, we employed supercritical fluid extraction (SFE) technology to isolate the bioactive compounds from HE’s fruiting body. Comprehensive assessments [...] Read more.

Hericium erinaceus (HE), a widely utilized natural remedy and dietary source, has garnered significant attention for its therapeutic potential in various diseases. In this study, we employed supercritical fluid extraction (SFE) technology to isolate the bioactive compounds from HE’s fruiting body. Comprehensive assessments of the antioxidant and antibacterial activities were conducted, along with in vitro investigations on the human colon cancer cell line (HCT-8). The SFE rate served as the evaluation metric, while the variables of extraction time, pressure, and temperature were systematically examined. By integrating the response surface center composite design, we successfully optimized the extraction process, yielding optimal parameters of 80 min, 30 MPa, and 35 °C, thus resulting in an extraction rate of 2.51%. These optimized conditions exhibited considerable antioxidant capacity, anticancer activity, and antibacterial potential. Furthermore, we employed graded alcohol extraction to refine the crude extracts, thereby confirming superior anticancer effects under a 70% alcohol precipitation. To elucidate the composition, Fourier-transform infrared spectroscopy (FT-IR) and gas chromatography-mass spectrometry (GC-MS) were employed to analyze the crude extracts and isolates of HE, facilitating a comparative analysis of six HE varieties. Our findings suggest that sterol derivatives hold promise as the active component against the colon cancer HCT-8 cell line. In conclusion, this study underscores the potential of HE SFE in the development of functional foods or alternative drugs for colon cancer treatment, thus opening new avenues for therapeutic interventions. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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10 pages, 651 KiB

Open AccessArticle

Two New Compounds from Allii Macrostemonis Bulbus and Their In Vitro Antioxidant Activities

by Jianfa Wu, Lei Li, Chang Liu, Chunyi Li, Ying Cui, Weixing Ding, Jing Zhang and Leiling Shi

Molecules 2023, 28(17), 6176; https://doi.org/10.3390/molecules28176176 - 22 Aug 2023

Cited by 3 | Viewed by 1275

Abstract

Two new compounds named 4,4′-bis(β-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, [...] Read more.

Two new compounds named 4,4′-bis(β-D-glucopyranosyloxy)biphenyl (1) and spirostane-25(27)-en-2α,3β-diol-3-O-β-D-xylopyranosyl(1→3)-β-D-glucopyranosyl(1→4)-β-D-galactopyranoside (2) were isolated from n-butanol extraction part of 80% ethanol extract of Allii Macrostemonis Bulbus. Alongside these, ten known compounds (3–12) were also identified, including a flavonoid glycoside (3), seven steroids (4–10), a nucleoside (11), and a phenylpropanoid glycoside (12) were found. Notably, compounds 3–6 were isolated from this plant for the first time. The structures of all compounds were confirmed using high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), 1D, and 2D NMR spectroscopy. Some of these compounds showed strong antioxidant activity, and compound 1 demonstrated the most potent reduction of ferric ions (Fe³⁺) with an IC₅₀ value of 0.59 ± 0.18 mg/mL. Compounds 2 and 3 exhibited the highest scavenging activity against superoxide anion radicals (O₂⁻·) with an IC₅₀ value of 0.02 ± 0.01 mg/mL. Additionally, compound 3 displayed substantial scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) with IC₅₀ values of 0.21 ± 0.17 mg/mL and 0.02 ± 0.01 mg/mL, respectively. The discovery of these two new compounds is a reference for identifying Allii Macrostemonis Bulbus quality markers. Moreover, their exceptional antioxidant activity offers a promising avenue for uncovering novel natural antioxidants. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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13 pages, 1898 KiB

Open AccessArticle

Cytoprotective Effect of Bambusae caulis in Liquamen by Blocking Oxidative Stress in Hepatocytes

by Ji Hye Yang

Molecules 2023, 28(15), 5862; https://doi.org/10.3390/molecules28155862 - 3 Aug 2023

Cited by 2 | Viewed by 1209

Abstract

Bambusae caulis in Liquamen (BCL), which is extracted from heat-treated fresh bamboo stems, is a traditional herbal medicine widely used in Eastern countries. Recently, it has been reported to have anti-inflammatory and whitening effects. However, the protective effect of BCL on hepatocytes has [...] Read more.

Bambusae caulis in Liquamen (BCL), which is extracted from heat-treated fresh bamboo stems, is a traditional herbal medicine widely used in Eastern countries. Recently, it has been reported to have anti-inflammatory and whitening effects. However, the protective effect of BCL on hepatocytes has not yet been elucidated. The present study aimed to determine whether BCL prevents oxidative stress induced by tert-butyl hydroperoxide (t-BHP) and exerts cytoprotective effects on hepatocytes. High-performance liquid chromatography and liquid chromatography with tandem mass spectroscopy were performed to analyze the type of polyphenols present in BCL. The activities of antioxidant enzymes and hepatocyte viability were assessed. The benzoic acid content was the highest among polyphenols present in BCL. Benzoic acid acts as a scavenger of free radicals, including reactive oxygen species. BCL increased the expression of antioxidant enzymes (glutamate–cysteine ligase and NADPH quinone dehydrogenase (1)) by activating nuclear factor erythroid 2-related factor 2 and reduced tBHP-induced cell death by inhibiting oxidative stress. BCL inhibited tBHP-induced phosphorylation of p38 and c-Jun N-terminal kinase but not that of extracellular signal-regulated kinase. In conclusion, BCL is a promising therapeutic candidate for treating oxidative-stress-induced hepatocyte damage. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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18 pages, 2454 KiB

Open AccessArticle

Phanerosides A–X, Phenylpropanoid Esters of Sucrose from the Rattans of Phanera championii Benth

by Ya-Jie Hu, Qian Lan, Bao-Jun Su and Dong Liang

Molecules 2023, 28(12), 4767; https://doi.org/10.3390/molecules28124767 - 14 Jun 2023

Cited by 5 | Viewed by 1152

Abstract

Twenty-four new phenylpropanoid esters of sucrose, phanerosides A–X (1–24), were isolated from an EtOH extract of the rattans of Phanera championii Benth. (Fabaceae). Their structures were elucidated on the basis of comprehensive spectroscopic data analysis. A wide range of [...] Read more.

Twenty-four new phenylpropanoid esters of sucrose, phanerosides A–X (1–24), were isolated from an EtOH extract of the rattans of Phanera championii Benth. (Fabaceae). Their structures were elucidated on the basis of comprehensive spectroscopic data analysis. A wide range of structural analogues were presented due to the different numbers and positions of acetyl substituents and the structures of phenylpropanoid moieties. Phenylpropanoid esters of sucrose were isolated from the Fabaceae family for the first time. Biologically, the inhibitory effects of compounds 6 and 21 on NO production in LPS-induced BV-2 microglial cells were better than that of the positive control, with IC₅₀ values of 6.7 and 5.2 μM, respectively. The antioxidant activity assay showed that compounds 5, 15, 17, and 24 displayed moderate DPPH radical scavenging activity, with IC₅₀ values ranging from 34.9 to 43.9 μM. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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12 pages, 1477 KiB

Open AccessArticle

Separation of Flavonoids and Purification of Chlorogenic Acid from Bamboo Leaves Extraction Residues by Combination of Macroporous Resin and High-Speed Counter-Current Chromatography

by Yifeng Zhou, Meixu Chen, Xinyi Huo, Qilin Xu, Linlin Wu and Liling Wang

Molecules 2023, 28(11), 4443; https://doi.org/10.3390/molecules28114443 - 30 May 2023

Cited by 4 | Viewed by 2267

Abstract

Flavonoids are major active small-molecule compounds in bamboo leaves, which can be easily obtained from the bamboo leaves extraction residues (BLER) after the polysaccharides extraction. Six macroporous resins with different properties were screened to prepare and enrich isoorientin (IOR), orientin (OR), vitexin (VI), [...] Read more.

Flavonoids are major active small-molecule compounds in bamboo leaves, which can be easily obtained from the bamboo leaves extraction residues (BLER) after the polysaccharides extraction. Six macroporous resins with different properties were screened to prepare and enrich isoorientin (IOR), orientin (OR), vitexin (VI), and isovitexin (IVI) from BLER, and the XAD-7HP resin with the best adsorption and desorption performance was selected for further evaluation. Based on the static adsorption experiments, the experimental results showed that the adsorption isotherm fitted well with the Langmuir isotherm model, and the adsorption process was better explained by the pseudo-second-order kinetic model. After the dynamic trial of resin column chromatography, 20 bed volume (BV) of upload sample and 60% ethanol as eluting solvent was used in a lab scale-up separation, and the results demonstrated that the content of four flavonoids could be increased by 4.5-fold, with recoveries between 72.86 and 88.21%. In addition, chlorogenic acid (CA) with purity of 95.1% was obtained in water-eluted parts during dynamic resin separation and further purified by high-speed countercurrent chromatography (HSCCC). In conclusion, this rapid and efficient method can provide a reference to utilize BLER to produce high-value-added food and pharmaceutical products. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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17 pages, 4320 KiB

Open AccessArticle

Tandem LC-MS Identification of Antitubercular Compounds in Zones of Growth Inhibition Produced by South African Filamentous Actinobacteria

by Daniel J. Watson, Lubbe Wiesner, Tlhalefo Matimela, Denzil Beukes and Paul R. Meyers

Molecules 2023, 28(11), 4276; https://doi.org/10.3390/molecules28114276 - 23 May 2023

Viewed by 2557

Abstract

Novel antitubercular compounds are urgently needed to combat drug-resistant Mycobacterium tuberculosis (Mtb). Filamentous actinobacteria have historically been an excellent source of antitubercular drugs. Despite this, drug discovery from these microorganisms has fallen out of favour due to the continual rediscovery of known compounds. [...] Read more.

Novel antitubercular compounds are urgently needed to combat drug-resistant Mycobacterium tuberculosis (Mtb). Filamentous actinobacteria have historically been an excellent source of antitubercular drugs. Despite this, drug discovery from these microorganisms has fallen out of favour due to the continual rediscovery of known compounds. To increase the chance of discovering novel antibiotics, biodiverse and rare strains should be prioritised. Subsequently, active samples need to be dereplicated as early as possible to focus efforts on truly novel compounds. In this study, 42 South African filamentous actinobacteria were screened for antimycobacterial activity using the agar overlay method against the Mtb indicator Mycolicibacterium aurum under six different nutrient growth conditions. Known compounds were subsequently identified through extraction and high-resolution mass spectrometric analysis of the zones of growth inhibition produced by active strains. This allowed the dereplication of 15 hits from six strains that were found to be producing puromycin, actinomycin D and valinomycin. The remaining active strains were grown in liquid cultures, extracted and submitted for screening against Mtb in vitro. Actinomadura napierensis B60^T was the most active sample and was selected for bioassay-guided purification. This resulted in the identification of tetromadurin, a known compound, but which we show for the first time to have potent antitubercular activity, with the MIC₉₀s within the range of 73.7–151.6 nM against M. tuberculosis H37Rv^T in vitro under different test conditions. This shows that South African actinobacteria are a good source of novel antitubercular compounds and warrant further screening. It is also revealed that active hits can be dereplicated by HPLC-MS/MS analysis of the zones of growth inhibition produced by the agar overlay technique. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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18 pages, 2438 KiB

Open AccessArticle

Characterization of the Key Compounds of Bell Pepper by Spectrophotometry and Gas Chromatography on the Effects of Induced Stress on the Concentration of Secondary Metabolite

by Sandra N. Jimenez-García, Lina Garcia-Mier, Xóchitl S. Ramirez-Gomez, Ramon G. Guevara-Gonzalez, Humberto Aguirre-Becerra, Alexandro Escobar-Ortiz, Luis M. Contreras-Medina, Juan F. Garcia-Trejo, Moises A. Vazquez-Cruz and Ana A. Feregrino-Perez

Molecules 2023, 28(9), 3830; https://doi.org/10.3390/molecules28093830 - 30 Apr 2023

Cited by 2 | Viewed by 2342

Abstract

Sweet peppers are consumed worldwide, and traditional uses have sparked interest in their applications as dietary antioxidants, which can be enhanced in plants using elicitors. These are endowed with phytochemicals with potential health benefits such as antioxidants, bioavailability, and bioaccessibility. The trend in [...] Read more.

Sweet peppers are consumed worldwide, and traditional uses have sparked interest in their applications as dietary antioxidants, which can be enhanced in plants using elicitors. These are endowed with phytochemicals with potential health benefits such as antioxidants, bioavailability, and bioaccessibility. The trend in metabolomics shows us chemical fingerprints linking metabolomics, innovative analytical form, and bioinformatics tools. The objective was to evaluate the impact of multiple stress interactions, elicitor concentrations, and electrical conductivity on the concentration of secondary metabolites to relate their response to metabolic pathways through the foliar application of a cocktail of said elicitors in pepper crops under greenhouse conditions. The extracts were analyzed by spectrophotometry and gas chromatography, and it was shown that the PCA analysis identified phenolic compounds and low molecular weight metabolites, confirming this as a metabolomic fingerprint in the hierarchical analysis. These compounds were also integrated by simultaneous gene and metabolite simulants to obtain effect information on different metabolic pathways. Showing changes in metabolite levels at T6 (36 mM H₂O₂ and 3.6 dS/m) and T7 (0.1 mM SA and 3.6 dS/m) but showing statistically significant changes at T5 (3.6 dS/m) and T8 (0.1 mM SA, 36 mM H₂O₂, and 3.6 dS/m) compared to T1 (32 dS/m) or control. Six pathways changed significantly (p < 0.05) in stress-induced treatments: aminoacyl t-RNA and valine-leucine-isoleucine biosynthesis, and alanine-aspartate-glutamate metabolism, glycoxylate-dicarboxylate cycle, arginine-proline, and citrate. This research provided a complete profile for the characterization of metabolomic fingerprint of bell pepper under multiple stress conditions. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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14 pages, 4291 KiB

Open AccessArticle

Acetogenins-Rich Fractions of Annona coriacea Suppress Human Glioblastoma Viability and Migration by Regulating Necroptosis and MMP-2 Activity In Vitro

by Lorena R. Sousa, Ana Gabriela S. Oliveira, Antônio Arantes, João Gabriel M. Junqueira, Gerso P. Alexandre, Vanessa G. P. Severino, Rui Manuel Reis, Bonglee Kim and Rosy I. M. A. Ribeiro

Molecules 2023, 28(9), 3809; https://doi.org/10.3390/molecules28093809 - 29 Apr 2023

Cited by 2 | Viewed by 2711

Abstract

Glioblastoma (GBM) is an incurable primary brain tumor with a poor prognosis. Resection, radiation therapy, and temozolomide (TMZ) are insufficient to increase survival, making the treatment limited. Thus, the search for more effective and specific treatments is essential, making plants a promising source [...] Read more.

Glioblastoma (GBM) is an incurable primary brain tumor with a poor prognosis. Resection, radiation therapy, and temozolomide (TMZ) are insufficient to increase survival, making the treatment limited. Thus, the search for more effective and specific treatments is essential, making plants a promising source for elucidating new anti-glioblastoma compounds. Accordingly, this study investigated the effects of four fractions of hexane and ethyl acetate extract of Annona coriacea Mart., enriched with acetogenins, against GBM cell lines. All four fractions were selectively cytotoxic to GBM cells when compared to TMZ. Moreover, A. coriacea fractions delayed cell migration; reduced cytoplasmic projections, the metalloproteinase 2 (MMP-2) activity; and induced morphological changes characteristic of necroptosis, possibly correlated with the increase in receptor-interacting protein kinase 1 and 3 (RIP-1 and RIP-3), apoptosis-inducing factor (AIF), and the non-activation of cleaved caspase 8. The present findings reinforce that fractions of A. coriacea Mart. should be considered for more studies focusing treatment of GBM. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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17 pages, 995 KiB

Open AccessArticle

Phytochemical Analysis of Anastatica hierochuntica and Aerva javanica Grown in Qatar: Their Biological Activities and Identification of Some Active Ingredients

by Vandana Thotathil, Naheed Sidiq, Ameena Fakhroo and Lakshmaiah Sreerama

Molecules 2023, 28(8), 3364; https://doi.org/10.3390/molecules28083364 - 11 Apr 2023

Cited by 4 | Viewed by 2284

Abstract

Plant-derived compounds and their extracts are known to exhibit chemo preventive (antimicrobial, antioxidant and other) activities. The levels of such chemo preventive compounds vary depending on environmental factors, including the regions where they grow. Described in this study are: (i) a phytochemical analysis [...] Read more.

Plant-derived compounds and their extracts are known to exhibit chemo preventive (antimicrobial, antioxidant and other) activities. The levels of such chemo preventive compounds vary depending on environmental factors, including the regions where they grow. Described in this study are: (i) a phytochemical analysis of the two plants grown in the desert environment of Qatar, viz., Anastatica hierochuntica and Aerva javanica; (ii) the antibacterial, antifungal and antioxidant activities of various solvent extracts of these plants; (iii) a report on the isolation of several pure compounds from these plants. The phytochemical screening indicated the presence of glycosides, tannins, flavonoids, terpenoids, saponins, phenol and anthraquinones in various extracts of each of the plants. Antibacterial and antioxidant activities were studied using agar diffusion and DPPH methods, respectively. The extracts of Anastatica hierochuntica as well as Aerva javanica inhibit the growth of both gram-positive and gram-negative bacterial species. Various extracts of the two plants also exhibited higher or similar antioxidant activities as those of the standard antioxidants, α-tocopherol and ascorbic acid. The extracts of these plants were further purified by HPLC and characterized by IR and NMR techniques. This process has led to identification of β-sitosterol, campesterol and methyl-9-(4-(3,4-dihydroxy-1′-methyl-5′-oxocyclohexyl)-2-hydroxycyclohexyl)nonanoate from Anastatica hierochuntica, and lupenone, betulinic acid, lupeol acetate and persinoside A and B from Aerva javanica. The results reported herein suggests that Anastatica hierochuntica and Aerva javanica are potent sources of phytomedicines. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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22 pages, 60570 KiB

Open AccessArticle

Valorization of Pumpkin Peel as a Source of Bioactive Compounds: Optimization of Heat- and Ultrasound-Assisted Extraction

by Maria G. Leichtweis, Adriana K. Molina, Spyridon A. Petropoulos, Márcio Carocho, Tânia C. S. P. Pires, Maria Inês Dias, Ricardo Calhelha, M. Beatriz P. P. Oliveira, Carla Pereira and Lillian Barros

Molecules 2023, 28(7), 3168; https://doi.org/10.3390/molecules28073168 - 2 Apr 2023

Cited by 9 | Viewed by 2507

Abstract

The peels from three pumpkin genotypes cultivated in Greece were assessed for their phenolic content and bioactive properties to obtain extracts with a high preservative capacity. The optimization of the extraction was performed through response surface methodology (RSM) based on a Box–Behnken experimental [...] Read more.

The peels from three pumpkin genotypes cultivated in Greece were assessed for their phenolic content and bioactive properties to obtain extracts with a high preservative capacity. The optimization of the extraction was performed through response surface methodology (RSM) based on a Box–Behnken experimental design after applying two extraction techniques: heat-assisted (HAE) and ultrasound-assisted (UAE) extraction. The implemented independent variables were time, solvent concentration, and temperature/power (for HAE/UAE), while as dependent variables the dry residue (DR), reducing power (RP), and total phenolic content (TP) were considered. In general, HAE was the most effective technique for ‘TL’ (75 min; 30 °C; 24% ethanol) and ‘Voutirato’ (15 min; 30 °C; 10% ethanol), while UAE was more effective for ‘Leuka Melitis’ (5 min; 400 W; 0% ethanol). The extracts obtained in the global optimum conditions for each genotype peel were then assessed for their phenolic profile, by HPLC-DAD-ESI/MS, and bioactive potential. Seven phenolic compounds were detected, including four flavonoids, two phenolic acids, and one flavan-3-ol. The extracts presented high antioxidant, antibacterial, and antifungal potential, with no cytotoxicity for non-tumor cells. The optimized conditions for the extraction of preservative compounds from bioresidues were defined, allowing the acquisition of antioxidant and antimicrobial extracts and proving their potential for food application. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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15 pages, 581 KiB

Open AccessArticle

Bio-Prospecting of Crude Leaf Extracts from Thirteen Plants of Brazilian Cerrado Biome on Human Glioma Cell Lines

by Viviane A. O. Silva, Marcela N. Rosa, Izabela N. F. Gomes, Patrik da Silva Vital, Ana Laura V. Alves, Adriane F. Evangelista, Giovanna B. Longato, Adriana C. Carloni, Bruno G. Oliveira, Fernanda E. Pinto, Wanderson Romão, Allisson R. Rezende, Arali A. C. Araújo, Lohanna S. F. M. Oliveira, Alessandra A. M. Souza, Stephanie C. Oliveira, Rosy Iara Maciel A. Ribeiro and Rui M. Reis

Molecules 2023, 28(3), 1394; https://doi.org/10.3390/molecules28031394 - 1 Feb 2023

Cited by 1 | Viewed by 2296

Abstract

(1) Background: Malignant gliomas are aggressive tumors characterized by fast cellular growth and highly invasive properties. Despite all biological and clinical advances in therapy, the standard treatment remains essentially palliative. Therefore, searching for alternative therapies that minimize adverse symptoms and improve glioblastoma patients’ [...] Read more.

(1) Background: Malignant gliomas are aggressive tumors characterized by fast cellular growth and highly invasive properties. Despite all biological and clinical advances in therapy, the standard treatment remains essentially palliative. Therefore, searching for alternative therapies that minimize adverse symptoms and improve glioblastoma patients’ outcomes is imperative. Natural products represent an essential source in the discovery of such new drugs. Plants from the cerrado biome have been receiving increased attention due to the presence of secondary metabolites with significant therapeutic potential. (2) Aim: This study provides data on the cytotoxic potential of 13 leaf extracts obtained from plants of 5 families (Anacardiaceae, Annonaceae, Fabaceae, Melastomataceae e Siparunaceae) found in the Brazilian cerrado biome on a panel of 5 glioma cell lines and one normal astrocyte. (3) Methods: The effect of crude extracts on cell viability was evaluated by MTS assay. Mass spectrometry (ESI FT-ICR MS) was performed to identify the secondary metabolites classes presented in the crude extracts and partitions. (4) Results: Our results revealed the cytotoxic potential of Melastomataceae species Miconia cuspidata, Miconia albicans, and Miconia chamissois. Additionally, comparing the four partitions obtained from M. chamissois crude extract indicates that the chloroform partition had the greatest cytotoxic activity against the glioma cell lines. The partitions also showed a mean IC₅₀ close to chemotherapy, temozolomide; nevertheless, lower toxicity against normal astrocytes. Analysis of secondary metabolites classes presented in these crude extracts and partitions indicates the presence of phenolic compounds. (5) Conclusions: These findings highlight M. chamissois chloroform partition as a promising component and may guide the search for the development of additional new anticancer therapies. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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10 pages, 518 KiB

Open AccessArticle

Chemical Characterization and Antimicrobial Properties of the Hydroalcoholic Solution of Echinacea purpurea (L.) Moench. and Propolis from Northern Italy

by Stefania Garzoli, Francesca Maggio, Vittorio Vinciguerra, Chiara Rossi, Matthew Gavino Donadu and Annalisa Serio

Molecules 2023, 28(3), 1380; https://doi.org/10.3390/molecules28031380 - 1 Feb 2023

Cited by 9 | Viewed by 2104

Abstract

In this study, for the first time, the chemical composition of Echinacea purpurea (L.) Moench. and propolis (EAP) hydroalcoholic solution from the Trentino Alto Adige region of northern Italy was investigated by using SPME-GC-MS to describe the volatile content and GC-MS after silylation [...] Read more.

In this study, for the first time, the chemical composition of Echinacea purpurea (L.) Moench. and propolis (EAP) hydroalcoholic solution from the Trentino Alto Adige region of northern Italy was investigated by using SPME-GC-MS to describe the volatile content and GC-MS after silylation to detect the non-volatile compounds in the extractable organic matter. The antimicrobial activity of EAP hydroalcoholic solution was evaluated by Minimum Inhibitory Concentration (MIC) determination on 13 type strains, food and clinical isolates. Time Kill Kinetics (TKK) assays and the determination on swimming and swarming motility for 48 h gave more details on the mode of action of EAP solution. The results highlighted the presence of some terpenes and a large number of compounds belonging to different chemical classes. Among these, sugars and organic acids excelled. The EAP hydroalcoholic solution exhibited a strong antimicrobial activity in terms of MIC, with a clear decrease in the cellular load after 48 h. However, the bacterial motility may not be affected by the EAP treatment, displaying a dynamic swarming and swimming motility capacity over time. Given the complexity of chemical profile and the strong antimicrobial effectiveness, the EAP hydroalcoholic solution can be considered a source of bioactive molecules, deserving further investigation for the versatility of application. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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11 pages, 3318 KiB

Open AccessArticle

Immunomodulatory Effects of Cinnamaldehyde in Staphylococcus aureus-Infected Wounds

by Cristiane Santos Silva e Silva Figueiredo, Patrícia Vieira de Oliveira, Warlison Felipe da Silva Saminez, Roseana Muniz Diniz, Juliana Silva Pereira Mendonça, Lucas dos Santos Silva, Miria Yasmim Miranda Paiva, Mayara de Santana do Nascimento, Amanda Silva dos Santos Aliança, Adrielle Zagmignan, João Francisco Silva Rodrigues, Joicy Cortêz de Sá Souza, Marcos Augusto Grigolin Grisotto and Luís Cláudio Nascimento da Silva

Molecules 2023, 28(3), 1204; https://doi.org/10.3390/molecules28031204 - 26 Jan 2023

Cited by 2 | Viewed by 1988

Abstract

Cinnamaldehyde (CNM) is an essential-oil component with reported anti-infective, anti-inflammatory, and healing effects, making it an interesting compound for the treatment of wound infection. Herein, we evaluated the effects of topical administration of CNM in experimental wounds infected by Staphylococcus aureus. Swiss mice [...] Read more.

Cinnamaldehyde (CNM) is an essential-oil component with reported anti-infective, anti-inflammatory, and healing effects, making it an interesting compound for the treatment of wound infection. Herein, we evaluated the effects of topical administration of CNM in experimental wounds infected by Staphylococcus aureus. Swiss mice (n = 12/group) were randomly allocated into three groups (CON: animals with uninfected lesions; Sa: animals with untreated infected lesions; Sa + CNM: animals with infected wounds and treated with CNM). Excisional lesions (64 mm²) were induced at the dorsal area followed by the addition of S. aureus (80 μL of a 1.5 × 10⁸ CFU/mL bacterial suspension). The wounds were treated with CNM (200 μg/wound/day) or vehicle (2% DMSO) for 10 days. Skin samples were taken on the 3^rd or 10^th treatment day for quantification of inflammatory mediators, bacterial load, immunophenotyping, and histological analysis. The treatment with CNM improved the healing process and attenuated the severity of skin lesions infected by S. aureus. These effects were associated with significant decreases in bacterial loads in CNM-treated wounds. The levels of neutrophils, TNF-α, IL-6, NO, and VEGF were decreased in the lesions treated with CNM. Taken together, these data provide further evidence of the effectiveness of CNM for the treatment of skin infections. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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15 pages, 2251 KiB

Open AccessArticle

Identifications of Surfactin-Type Biosurfactants Produced by Bacillus Species Isolated from Rhizosphere of Vegetables

by Attila Bartal, Thu Huynh, Anita Kecskeméti, Mónika Vörös, Orsolya Kedves, Henrietta Allaga, Mónika Varga, László Kredics, Csaba Vágvölgyi and András Szekeres

Molecules 2023, 28(3), 1172; https://doi.org/10.3390/molecules28031172 - 25 Jan 2023

Cited by 6 | Viewed by 2552

Abstract

Surfactins are cyclic lipopeptides consisting of a β-hydroxy fatty acid of variable chain length and a peptide ring of seven amino acids linked together by a lactone bridge, forming the cyclic structure of the peptide chain. These compounds are produced mainly by Bacillus [...] Read more.

Surfactins are cyclic lipopeptides consisting of a β-hydroxy fatty acid of variable chain length and a peptide ring of seven amino acids linked together by a lactone bridge, forming the cyclic structure of the peptide chain. These compounds are produced mainly by Bacillus species and are well regarded for their antibacterial, antifungal, and antiviral activities. For their surfactin production profiling, several Bacillus strains isolated from vegetable rhizospheres were identified by their fatty acid methyl ester profiles and were tested against phytopathogen bacteria and fungi. The isolates showed significant inhibition against of E. amylovora, X. campestris, B. cinerea, and F. culmorum and caused moderate effects on P. syringae, E. carotovora, A. tumefaciens, F. graminearum, F. solani, and C. gloeosporioides. Then, an HPLC-HESI-MS/MS method was applied to simultaneously carry out the quantitative and in-depth qualitative characterisations on the extracted ferment broths. More than half of the examined Bacillus strains produced surfactin, and the MS/MS spectra analyses of their sodiated precursor ions revealed a total of 29 surfactin variants and homologues, some of them with an extremely large number of peaks with different retention times, suggesting a large number of variations in the branching of their fatty acid chains. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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11 pages, 1949 KiB

Open AccessArticle

Synergistic Inhibiting Effect of Phytochemicals in Rheum palmatum on Tyrosinase Based on Metabolomics and Isobologram Analyses

by Yin Xiong, Hye Kyong Kim, Övgü Çelikler Özer, Bert van Duijn, Henrie A. A. J. Korthout, Lihong Zi and Ang Cai

Molecules 2023, 28(3), 944; https://doi.org/10.3390/molecules28030944 - 17 Jan 2023

Cited by 4 | Viewed by 2129

Abstract

Tyrosinase (TYR) plays a key role in the enzymatic reaction that is responsible for a range of unwanted discoloration effects, such as food browning and skin hyperpigmentation. TYR inhibitors could, therefore, be candidates for skin care products that aim to repair pigmentation problems. [...] Read more.

Tyrosinase (TYR) plays a key role in the enzymatic reaction that is responsible for a range of unwanted discoloration effects, such as food browning and skin hyperpigmentation. TYR inhibitors could, therefore, be candidates for skin care products that aim to repair pigmentation problems. In this study, we used a metabolomics approach combined with the isobologram analysis to identify anti-TYR compounds within natural resources, and evaluate their possible synergism with each other. Rheum palmatum was determined to be a model plant for observing the effect, of which seven extracts with diverse phytochemicals were prepared by way of pressurized solvent extraction. Each Rheum palmatum extract (RPE) was profiled using nuclear magnetic resonance spectroscopy and its activity of tyrosinase inhibition was evaluated. According to the orthogonal partial least square analysis used to correlate phytochemicals in RPE with the corresponding activity, the goodness of fit of the model (R₂ = 0.838) and its predictive ability (Q₂ = 0.711) were high. Gallic acid and catechin were identified as the active compounds most relevant to the anti-TYR effect of RPE. Subsequently, the activity of gallic acid and catechin were evaluated individually, and when combined in various ratios by using isobologram analysis. The results showed that gallic acid and catechin in the molar ratios of 9:5 and 9:1 exhibited a synergistic inhibition on TYR, with a combination index lower than 0.77, suggesting that certain combinations of these compounds may prove effective for use in cosmetic, pharmaceutical, and food industries. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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18 pages, 2493 KiB

Open AccessArticle

Triterpenoid and Steroid Content of Lipophilic Extracts of Selected Medicinal Plants of the Mediterranean Region

by Leila Gadouche, Abdulwadood Shakir Mahmood Alsoufi, Dominika Pacholska, Anna Skotarek, Cezary Pączkowski and Anna Szakiel

Molecules 2023, 28(2), 697; https://doi.org/10.3390/molecules28020697 - 10 Jan 2023

Cited by 6 | Viewed by 2826

Abstract

The available phytochemical characteristics of the medicinal plants and derived herbal material often lack data concerning the content of steroids (including phytosterols) and triterpenoids, that can be responsible for various beneficial properties and therapeutic effects, either directly, or as a result of synergistic [...] Read more.

The available phytochemical characteristics of the medicinal plants and derived herbal material often lack data concerning the content of steroids (including phytosterols) and triterpenoids, that can be responsible for various beneficial properties and therapeutic effects, either directly, or as a result of synergistic action with other bioactive constituents. The aim of the present work was the analysis of the content of these compounds in herbal material (leaves, aerial parts) derived from selected medicinal plants (Cistus ladanifer, Cistus monspeliensis, Erica arborea, Globularia alypum, Pistacia lentiscus, Rhamnus alaternus), widely used in folk medicine in the Mediterranean region. Results obtained by gas chromatography-mass spectrometry (GC-MS)-targeted profiling revealed the diversity in the profiles and contents of steroids and triterpenoids in the analyzed plant material, ranging from 5.7% d.w. in E. arborea to 0.1% in G. alypum. The obtained results supplement the existing phytochemical data of the investigated medicinal plants, pointing to the E. arborea aerial parts and P. lentiscus leaves as valuable resources of phytosterols and bioactive triterpenoids. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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13 pages, 1247 KiB

Open AccessArticle

Identification of Secondary Metabolites of Interest in Pleurotus djamor Using Agave tequilana Bagasse

by Byanka A. Cruz-Moreno, Ana Angélica Feregrino Pérez, Juan Fernando García-Trejo, Sergio Alfonso Pérez-García and Claudia Gutiérrez-Antonio

Molecules 2023, 28(2), 557; https://doi.org/10.3390/molecules28020557 - 5 Jan 2023

Cited by 4 | Viewed by 2338

Abstract

Agro-industrial residues represent more than 60% of organic wastes worldwide, which could be used to generate other by-products or to be incorporated into other production chains. For example, bagasse is a waste from the tequila industry in Mexico that could be implemented for [...] Read more.

Agro-industrial residues represent more than 60% of organic wastes worldwide, which could be used to generate other by-products or to be incorporated into other production chains. For example, bagasse is a waste from the tequila industry in Mexico that could be implemented for mushroom cultivation. Additionally, the substrate influences the growth, development, and production of secondary metabolites of fungi. This work presents a comparative experiment that studies the metabolite production in Pleurotus djamor mushrooms on agave bagasse and barley straw (traditional substrate). The biological efficiency (BE), yield, phenolics and flavonoids, antioxidant capacity, tannins, and the identification of low molecular weight metabolites were evaluated. Five treatments were proposed according to the following mixtures of agave bagasse: barley straw: T1 (1:0), T2 (3:1), T3 (1:1), T4 (1:3), and T5 (0:1). T2 had the highest yield (13.39 ± 3.23%), BE (56.7 ± 13.71%), and flavonoids (44.25 mg rutin equivalent (RE)/g); T3 obtained the highest phenol content (230.27 mg GAE/g); and T1 the highest tannins content (0.23 mg (+) catechin equivalent (CE)/g). Finally, T1 and T5 are the ones that present the greatest number of primary metabolites, including hydroxycitric acid, 2-deoxy-D-galactose, D-mannose, paromomycin, palmitic acid, pyrrole, mannitol, and DL arabinose, while in T2, T3, and T4 only two chemical compounds were found present (palmitic acid and pyrrole in T2, silicic acid and pyrrole in T3 and 2-deoxy-D-galactose and quinoline in T4). The cultivation substrate influences the concentration of bioactive molecules in the fruiting bodies of P. djamor. Additionally, P. djamor’s degradation of agave bagasse residue generates a potential application for agro-industrial residue management at a low cost. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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12 pages, 1194 KiB

Open AccessArticle

Essential Oil Composition Analysis of Cymbopogon Species from Eastern Nepal by GC-MS and Chiral GC-MS, and Antimicrobial Activity of Some Major Compounds

by Sabita Dangol, Darbin Kumar Poudel, Pawan Kumar Ojha, Salina Maharjan, Ambika Poudel, Rakesh Satyal, Anil Rokaya, Sujan Timsina, Noura S. Dosoky, Prabodh Satyal and William N. Setzer

Molecules 2023, 28(2), 543; https://doi.org/10.3390/molecules28020543 - 5 Jan 2023

Cited by 21 | Viewed by 4698

Abstract

Cymbopogon species essential oil (EO) carries significant importance in pharmaceuticals, aromatherapy, food, etc. The chemical compositions of Cymbopogon spp. Viz. Cymbopogon winterianus (citronella) Cymbopogon citratus (lemongrass), and Cymbopogon martini (palmarosa) were analyzed by gas chromatography–mass spectrometry (GC-MS), enantiomeric distribution by chiral GC-MS, and antimicrobial [...] Read more.

Cymbopogon species essential oil (EO) carries significant importance in pharmaceuticals, aromatherapy, food, etc. The chemical compositions of Cymbopogon spp. Viz. Cymbopogon winterianus (citronella) Cymbopogon citratus (lemongrass), and Cymbopogon martini (palmarosa) were analyzed by gas chromatography–mass spectrometry (GC-MS), enantiomeric distribution by chiral GC-MS, and antimicrobial activities of some selected pure major compound and root and leaves EOs of citronella. The EO of leaves of Cymbopogon spp. showed comparatively higher yield than roots or other parts. Contrary to citral (neral and geranial) being a predominant compound of Cymbopogon spp., α-elemol (53.1%), α-elemol (29.5%), geraniol (37.1%), and citral (90.4%) were detected as major compounds of the root, root hair with stalk, leaf, and root stalk with shoot of citronella EO, respectively. Palmarosa leaves’ EO contains neral (36.1%) and geranial (53.1) as the major compounds. In the roots of palmarosa EO, the prime components were α-elemol (31.5%), geranial (25.0%), and neral (16.6%). Similarly, lemongrass leaves’ EO contains geraniol (76.6%) and geranyl acetate (15.2%) as major compounds, while the root EO contains a higher amount of geraniol (87.9%) and lower amount of geranyl acetate (4.4%). This study reports for the first time chiral terpenoids from Cymbopogon spp. EOs. Chiral GC-MS gave specific enantiomeric distributions of nine, six, and five chiral terpenoids in the root, root stalk with a shoot, and leaves of citronella EOs, respectively. Likewise, four and three chiral terpenoids in the root and leaves of lemongrass oil followed by two chiral terpenoids in the leaves and root of palmarosa EOs each. Additionally, the root and leaves’ EOs of citronella exhibit noticeable activity on bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes and fungus such as Candida albicans, Microsporum canis, and Trichophyton mentagrophytes. So, geranial-, neral-, geraniol-, and citronellal-rich EOs can be used as an alternative antimicrobial agent. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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10 pages, 6935 KiB

Open AccessArticle

Comparative Study of the Efficiency of Additives in the Extraction of Phycocyanin-C from Arthrospira maxima Using Ultrasonication

by Jorge Eugenio Martínez-Vega, Erika Villafaña-Estarrón and Froylán M. E. Escalante

Molecules 2023, 28(1), 334; https://doi.org/10.3390/molecules28010334 - 31 Dec 2022

Cited by 5 | Viewed by 1706

Abstract

Several phycocyanin extraction methods have been proposed, however, most of them present economical or productive barriers. One of the most promising methods that has been suggested is ultrasonication. We have analyzed here the effect of operational conditions and additives on the extraction and [...] Read more.

Several phycocyanin extraction methods have been proposed, however, most of them present economical or productive barriers. One of the most promising methods that has been suggested is ultrasonication. We have analyzed here the effect of operational conditions and additives on the extraction and purity of phycocyanin from Arthrospira maxima. We followed three experimental designs to determine the best combination of buffered pH solutions, additives, fresh and lyophilized biomass. We have found that additives such as citric acid and/or disaccharides could be beneficial to the extraction process. We concluded that the biomass–solvent ratio is a determining factor to obtain high extraction and purity ratios with short ultrasonication times. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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20 pages, 4101 KiB

Open AccessArticle

Modeling and Optimization of the Isolation of Blackcurrant and Black Cumin Seeds Oils Using Supercritical Fluid Extraction

by Barbara Mazurek, Magdalena Wójciak, Dorota Kostrzewa and Małgorzata Kondracka

Molecules 2022, 27(24), 8921; https://doi.org/10.3390/molecules27248921 - 15 Dec 2022

Cited by 2 | Viewed by 1915

Abstract

Supercritical fluid extraction is a powerful analytical tool and it is willingly used by researchers for the isolation of various components from different matrices. In our study, the carbon dioxide in the supercritical state was used for the extraction of oils from blackcurrant [...] Read more.

Supercritical fluid extraction is a powerful analytical tool and it is willingly used by researchers for the isolation of various components from different matrices. In our study, the carbon dioxide in the supercritical state was used for the extraction of oils from blackcurrant and black cumin seeds. To determine the optimal conditions for the process (temperature, pressure and time), the method of statistical experiment planning and the Box–Behnken design was applied and the yield of the oils and the content of fatty acids (FAs) were taken into consideration. It has been found that an increase in pressure causes an increase in extraction yield (W), and an increase in temperature, both at constant pressure and time, does not significantly change the yield value. Optimal yield values were obtained for both materials under almost similar extraction parameters: 306 bar/ 43 min/ 50 °C (blackcurrant) and 282 bar/ 40 min/ 50 °C (black cumin). The influence of the above parameters (T, p, t) on the content of FAs in the extracts has a slightly different trend. The use of supercritical carbon dioxide for the extraction of blackcurrant and black cumin seeds allowed for high process yield and high-quality, rich in polyunsaturated fatty acids oils which can be used as a substrate or final product for industry. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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11 pages, 2036 KiB

Open AccessArticle

Meroterpenoids and Steroids from the Marine-Derived Fungus Trametes sp. ZYX-Z-16

by Ziming Ren, Li Yang, Qingyun Ma, Qingyi Xie, Haofu Dai, Kunlai Sun and Youxing Zhao

Molecules 2022, 27(24), 8782; https://doi.org/10.3390/molecules27248782 - 11 Dec 2022

Cited by 10 | Viewed by 1863

Abstract

Marine fungi can metabolize structurally diverse active components, and have become an important source of drug lead molecules. In the present study, the chemical investigation on the EtOAc extract of the fermentation broth of the marine-derived fungus Trametes sp. ZYX-Z-16 led to the [...] Read more.

Marine fungi can metabolize structurally diverse active components, and have become an important source of drug lead molecules. In the present study, the chemical investigation on the EtOAc extract of the fermentation broth of the marine-derived fungus Trametes sp. ZYX-Z-16 led to the isolation of eight meroterpenoids (1–8), including two undescribed ones, together with ten ergostane steroid analogues (9–18). The structures of two new spiromeroterpenoids, asnovolin H (1) and asnovolin I (2), were determined based on 1D, 2D NMR, and HRESIMS spectroscopic data along with ECD spectra calculations. All compounds were tested for antibacterial and α-glucosidase inhibitory activity. Among them, compound 12 showed definite antibacterial activities against Staphylococcus aureus ATCC 6538 (MIC 32 μg/mL) and Bacillus subtilis ATCC 6633 (MIC 16 μg/mL). In addition, compounds 9 and 10 showed superior inhibitory activity, with IC₅₀ values of 104.1 and 111.3 μM, respectively, to the positive control acarbose (304.6 μM). Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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15 pages, 2915 KiB

Open AccessArticle

Cardioprotective Effects of 6-Gingerol against Alcohol-Induced ROS-Mediated Tissue Injury and Apoptosis in Rats

by Venkata Subbaiah Ganjikunta, Ramana Reddy Maddula, Shanmugam Bhasha, Ravi Sahukari, Shanmugam Kondeti Ramudu, Venkatrayulu Chenji, Sathyavelu Reddy Kesireddy, Zhe Zheng and Mallikarjuna Korivi

Molecules 2022, 27(23), 8606; https://doi.org/10.3390/molecules27238606 - 6 Dec 2022

Cited by 7 | Viewed by 1870

Abstract

The present study investigated the cardioprotective properties of 6-gingerol against alcohol-induced ROS-mediated cardiac tissue damage in rats. Experiments were conducted on 4 groups of rats, orally treated with control, 6-gingerol (10 mg/kg body weight), alcohol (6 g/kg body weight) and combination of 6-gingerol [...] Read more.

The present study investigated the cardioprotective properties of 6-gingerol against alcohol-induced ROS-mediated cardiac tissue damage in rats. Experiments were conducted on 4 groups of rats, orally treated with control, 6-gingerol (10 mg/kg body weight), alcohol (6 g/kg body weight) and combination of 6-gingerol plus alcohol for two-month. In the results, we found 6-ginger treatment to alcohol-fed rats substantially suppressed ROS production in cardiac tissue. Alcohol-induced elevated 8-OHDG and protein carbonyls which represent oxidative modification of DNA and proteins were completely reversed by 6-gingerol. This was further endorsed by restored superoxide dismutase and catalase activities with 6-gingerol against alcohol-induced loss. The elevated cardiac biomarkers (CK-MB, cTn-T, cTn-I) and dyslipidemia in alcohol-intoxicated rats was significantly reversed by 6-gingerol. Furthermore, alcohol-induced apoptosis characterized by overexpression of cytochrome C, caspase-8 and caspase-9 was diminished with 6-gingerol treatment. Transmission electron microscope images conferred the cardioprotective properties of 6-gingerol as we have seen less structural derangements in mitochondria and reappearance of myofilaments. Our findings conclude that 6-ginger effectively protect alcohol-induced ROS-mediated cardiac tissue damage, which may be due to its potent antioxidant efficacy. Therefore, 6-gingerol could be a potential therapeutic molecule that can be used in the treatment of alcohol-induced myocardial injury. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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18 pages, 4202 KiB

Open AccessArticle

Transcriptional Responses for Biosynthesis of Triterpenoids in Exogenous Inducers Treated Inonotus Hispidus Using RNA-Seq

by Yonghong Huo, Dongchao Liu, Qin Yang, Changyan Sun, Zhanbin Wang and Dehai Li

Molecules 2022, 27(23), 8541; https://doi.org/10.3390/molecules27238541 - 4 Dec 2022

Cited by 1 | Viewed by 1527

Abstract

Inonotus hispidus is a traditional medicinal that grows in Northeast China and produces various economically important compounds, including polysaccharide compounds and terpenoids; triterpenoid saponins is the main bioactive component. Our research group has found that the accumulation of triterpenoid was affected by exogenous [...] Read more.

Inonotus hispidus is a traditional medicinal that grows in Northeast China and produces various economically important compounds, including polysaccharide compounds and terpenoids; triterpenoid saponins is the main bioactive component. Our research group has found that the accumulation of triterpenoid was affected by exogenous inducers. Experimental results showed that treatment with methyl jasmonate (MeJA) and oleic acid significantly increased the triterpenoid content of I. hispidus. However, how exogenous inducers enhance production of secondary metabolites in I. hispidus is not well understood. In this study, metabolite changes were further investigated with UPLC-TOF/MS following exogenous inducer treatment. As a result, a total of eight types of triterpenoids in I. hispidus were identified. The RNA-seq analysis was used to evaluate the effects of exogenous inducers on the expression of triterpenoid-synthesis-related genes in I. hispidus in liquid fermentation. This study is the first exploration to profile the transcriptome of I. hispidus after adding exogenous inducers; the generated data and gene will facilitate further molecular studies on the physiology and metabolism in this fungi. By comparative transcriptomic analysis, a series of candidate genes involved in the biosynthetic pathway of triterpenoids are identified, providing new insights into their biosynthesis at the transcriptome level. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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12 pages, 11148 KiB

Open AccessArticle

Synthesis and Anti-Inflammatory Activity of 1-Methylhydantoin Cinnamoyl Imides

by Shihan Wang, Li Ji, Dongxue Zhang, Hongye Guo, Yongsheng Wang and Wei Li

Molecules 2022, 27(23), 8481; https://doi.org/10.3390/molecules27238481 - 2 Dec 2022

Cited by 4 | Viewed by 1619

Abstract

In this study, 1-methylhydantoin cinnamic imides were synthesized from 1-methylhydantoin and trans-cinnamic acid, and their anti-inflammatory activity was investigated. The anti-inflammatory activity in vitro was evaluated by measuring the contents of NO, TNF-α and IL-1β in the supernatant of RAW264.7 cells stimulated [...] Read more.

In this study, 1-methylhydantoin cinnamic imides were synthesized from 1-methylhydantoin and trans-cinnamic acid, and their anti-inflammatory activity was investigated. The anti-inflammatory activity in vitro was evaluated by measuring the contents of NO, TNF-α and IL-1β in the supernatant of RAW264.7 cells stimulated by LPS. The cytotoxicity of 1-methylhydantoin cinnamoyl imides on RAW264.7 cells was detected using the CCK-8 method. The results showed that compounds 2 and 4 can significantly inhibit the release of NO and reduce the secretion of TNF-α and IL-1β. Compound 3 inhibited the production of TNF-α. The inhibition rate of COX was evaluated in vitro. The in vivo anti-inflammatory activities of the five compounds were evaluated by establishing an animal model of xylene ear swelling. The results showed that 1-methylhydantoin cinnamic imides could alleviate xylene-induced ear edema in mice in a dose-dependent manner. Among them, the effect of compound 5 was the most significant. Under the action of high dosage, its ear swelling inhibition rate was as high as 52.08%. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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26 pages, 15867 KiB

Open AccessArticle

Purification and Characterization of Novel Anti-MRSA Peptides Produced by Brevibacillus sp. SPR-20

by Nuttapon Songnaka, Monthon Lertcanawanichakul, Albert M. Hutapea, Sucheewin Krobthong, Yodying Yingchutrakul and Apichart Atipairin

Molecules 2022, 27(23), 8452; https://doi.org/10.3390/molecules27238452 - 2 Dec 2022

Cited by 7 | Viewed by 2342

Abstract

Methicillin-resistant Staphylococcus aureus (MRSA) is listed as a high-priority pathogen because its infection is associated with a high mortality rate. It is urgent to search for new agents to treat such an infection. Our previous study isolated a soil bacterium (Brevibacillus sp. [...] Read more.

Methicillin-resistant Staphylococcus aureus (MRSA) is listed as a high-priority pathogen because its infection is associated with a high mortality rate. It is urgent to search for new agents to treat such an infection. Our previous study isolated a soil bacterium (Brevibacillus sp. SPR-20), showing the highest antimicrobial activity against S. aureus TISTR 517 and MRSA strains. The present study aimed to purify and characterize anti-MRSA substances produced by SPR-20. The result showed that five active substances (P1–P5) were found, and they were identified by LC-MS/MS that provided the peptide sequences of 14–15 residues. Circular dichroism showed that all peptides contained β-strand and disordered conformations as the major secondary structures. Only P1–P4 adopted more α-helix conformations when incubated with 50 mM SDS. These anti-MRSA peptides could inhibit S. aureus and MRSA in concentrations of 2–32 μg/mL. P1 (NH₂-VVVNVLVKVLPPPVV-COOH) had the highest activity and was identified as a novel antimicrobial peptide (AMP). The stability study revealed that P1 was stable in response to temperature, proteolytic enzymes, surfactant, and pH. The electron micrograph showed that P1 induced bacterial membrane damage when treated at 1× MIC in the first hour of incubation. The killing kinetics of P1 was dependent on concentration and time. Mechanisms of P1 on tested pathogens involved membrane permeability, leakage of genetic material, and cell lysis. The P1 peptide at a concentration up to 32 μg/mL showed hemolysis of less than 10%, supporting its safety for human erythrocytes. This study provides promising anti-MRSA peptides that might be developed for effective antibiotics in the post-antibiotic era. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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15 pages, 883 KiB

Open AccessArticle

Partial Characterization of Lectins Purified from the Surco and Vara (Furrow and Rod) Varieties of Black Phaseolus vulgaris

by Carmen Valadez-Vega, Olivia Lugo-Magaña, Gabriel Betanzos-Cabrera and José Roberto Villagómez-Ibarra

Molecules 2022, 27(23), 8436; https://doi.org/10.3390/molecules27238436 - 2 Dec 2022

Cited by 3 | Viewed by 1693

Abstract

As they manifest specifically and reversibly, lectins are proteins or glycoproteins with the characteristic of agglutinating erythrocytes. Given that grain legume lectins can represent 10% of protein content and can have various biological functions, they are extensively studied. The objective of this work [...] Read more.

As they manifest specifically and reversibly, lectins are proteins or glycoproteins with the characteristic of agglutinating erythrocytes. Given that grain legume lectins can represent 10% of protein content and can have various biological functions, they are extensively studied. The objective of this work was to purify and partially characterize the lectins of Phaseolus vulgaris black, var surco and vara (LBBS and LBBV). Both lectin types were purified by affinity chromatography on stroma matrix, which agglutinated human erythrocytes type A, B, and O, as well as rabbit, hamster, pig, and chicken erythrocytes. Native-PAGE was employed for molecular mass determination, yielding 109.36 and 112.68 kDa for BBS and BBV, respectively. Further analyses revealed that these lectins are tetrameric glycoproteins that require Ca⁺², Mn⁺² and Mg⁺² ions for exhibiting their hemagglutinating function, which can be inhibited by fetuin. Moreover, optimal pH was established for both lectins (10.5 for LBBS and 7−9 for LBBV), while their activity was temperature-dependent and ceased above 70 °C. Finally, the observed differences in the biochemical characteristics and bioactive functions were ascribed to the different physiological characteristics of each seed, as well as the protein itself. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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11 pages, 5196 KiB

Open AccessArticle

Triptonoterpene, a Natural Product from Celastrus orbiculatus Thunb, Has Biological Activity against the Metastasis of Gastric Cancer Cells

by Haibo Wang, Yuanyuan Luo, Yaqi Hu, Xinyi Feng, Jun Feng, Zewen Chu, Shiya Ou, Xiaojun Dai, Xiaoqing Wang and Yanqing Liu

Molecules 2022, 27(22), 8005; https://doi.org/10.3390/molecules27228005 - 18 Nov 2022

Cited by 7 | Viewed by 1883

Abstract

Cancer is one of the greatest threats to human health. Gastric cancer (GC) is the fifth most common malignant tumor in the world. Invasion and metastasis are the major difficulties in the treatment of GC. Herbal medicines and their extracts have a lengthy [...] Read more.

Cancer is one of the greatest threats to human health. Gastric cancer (GC) is the fifth most common malignant tumor in the world. Invasion and metastasis are the major difficulties in the treatment of GC. Herbal medicines and their extracts have a lengthy history of being used to treat tumors in China. The anti-tumoral effects of the natural products derived from herbs have received a great deal of attention. Our previous studies have shown that the traditional Chinese herb Celastrus orbiculatus Thunb extract (COE) can inhibit the invasion and metastasis of GC cells, but the specific anti-cancer components of COE are still unclear. Dozens of natural products from COE have been isolated and identified by HPLC spectroscopy in our previous experiments. Triptonoterpene is one of the active ingredients in COE. In this study, we focused on revealing whether Triptonoterpene has an excellent anti-GC effect and can be used as an effective component of Celastrus orbiculatus Thunb in the treatment of tumors. We first observed that Triptonoterpene reduces GC cell proliferation through CCK-8 assays and colony formation experiments. The cell adhesion assays have shown that Triptonoterpene inhibits adhesion between cells and the cell matrix during tumor invasion. In addition, the cell migration assay has shown that Triptonoterpene inhibits the invasion and migration of GC cells. The high-connotation cell dynamic tracking experiment has also shown the same results. The effects of Triptonoterpene on epidermal mesenchymal transition (EMT)-related and matrix metalloproteinases (MMPs)-related proteins in gastric cancer cells were detected by Western blots. We found that Triptonoterpene could significantly inhibit the changes in EMT-related and invasion and metastasis-related proteins. Altogether, these results suggest that Triptonoterpene is capable of inhibiting the migration and invasion of GC cells. Triptonoterpene, as a natural product from Celastrus orbiculatus Thunb, has significant anti-gastric cancer effects, and is likely to be one of the major equivalent components of Celastrus orbiculatus Thunb. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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14 pages, 5589 KiB

Open AccessArticle

Differences in Chemical Constituents between Dalbergia oliveri Heartwood and Sapwood and Their Effect on Wood Color

by Liuming Wei, Ruoke Ma and Yunlin Fu

Molecules 2022, 27(22), 7978; https://doi.org/10.3390/molecules27227978 - 17 Nov 2022

Cited by 3 | Viewed by 2069

Abstract

The purpose of this study was to characterize and quantify the chemical constituents of heartwood and sapwood of Dalbergia oliveri extract in order to investigate the chemical components that determine the formation of heartwood’s color. In this work, the types of pigments in [...] Read more.

The purpose of this study was to characterize and quantify the chemical constituents of heartwood and sapwood of Dalbergia oliveri extract in order to investigate the chemical components that determine the formation of heartwood’s color. In this work, the types of pigments in heartwood and sapwood extract were analyzed using UV-Visible (UV) Spectrophotometer, and the main pigment components of heartwood and sapwood extract were identified and quantified using ultra-high performance liquid chromatography-mass spectrometry (UHPLC-MS). The results showed that the difference in content of the main components between heartwood and sapwood of Dalbergia oliveri was slight, and the lignin structure between heartwood and sapwood is basically identical; flavonoid pigments were found to be the primary chromophoric components of heartwood and sapwood extract. However, a total of 21 flavonoids were identified in heartwood and sapwood, of which the unique substances to heartwood were vitexin, isorhamnetin, and pelargonidin, and the content of isoliquiritigenin, formononetin, and biochanin A were 253, 37, and 583 times higher in the heartwood than in the sapwood, respectively, which could be the main pigment components affecting the significant color difference between heartwood and sapwood of Dalbergia oliveri. These results will provide a foundation for revealing the underlying mechanism of color difference between heartwood and sapwood and provide a theoretical basis for wood coloring. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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16 pages, 2718 KiB

Open AccessArticle

Standardized Pomegranate (Pomella^®) and Red Maple (Maplifa^®) Extracts and Their Phenolics Protect Type I Collagen by the Inhibition of Matrix Metalloproteinases, Collagenase, and Collagen Cross-Linking

by Huifang Li, Tithi Roy, Samuel T. Boateng, Hao He, Chang Liu, Weixi Liu, Dongli Li, Panpan Wu, Navindra P. Seeram, Jean Christopher Chamcheu and Hang Ma

Molecules 2022, 27(22), 7919; https://doi.org/10.3390/molecules27227919 - 16 Nov 2022

Cited by 3 | Viewed by 2126

Abstract

Phenolics enriched pomegranate fruit (Pomella^®) and red maple leaf (Maplifa^®) extracts and their major phenolic constituents have demonstrated beneficial skin effects through the protection of human skin keratinocytes from oxidative-stress-induced damage. However, their mechanisms of protection of cutaneous collagen [...] Read more.

Phenolics enriched pomegranate fruit (Pomella^®) and red maple leaf (Maplifa^®) extracts and their major phenolic constituents have demonstrated beneficial skin effects through the protection of human skin keratinocytes from oxidative-stress-induced damage. However, their mechanisms of protection of cutaneous collagen are still unclear. Herein, the collagen protective effects of Pomella^® and Maplifa^®, and their major bioactive phytochemicals, namely, punicalagin (PA) and ginnalin A (GA), respectively, were evaluated using enzymatic assays including collagenase, anti-glycation and cell-based models as well as computational methods. The importance of the modulatory effects was validated at the protein level for type I collagen and matrix metalloproteinases (MMPs) using human-skin-derived keratinocytes. The synergistic collagenase inhibitory effects upon combinations of Pomella^® + Maplifa^® and PA + GA at a combination ratio of 1:2 and 1:1, respectively, were evaluated using their combination index (CI; a well-established assessment of synergism). Pomella^® (50–400 µg/mL), Maplifa^® (100–800 µg/mL), PA (50–400 µM), and GA (50–400 µM) dose-dependently inhibited collagenase activity by 26.3–86.3%, 25.7–94.0%, 26.2–94.0%, and 12.0–98.0%, respectively. The CI of the anti-collagenase activity of Pomella^® and Maplifa^® ranged from 0.53–0.90, while that of PA and GA (12.5/12.5 and 25/25 µM) ranged from 0.66 and 0.69, respectively, suggesting a synergistic inhibitory effect. Interestingly, in the cell-based assays by Western blotting, Pomella^® and Maplifa^® reduced the protein expression levels of collagen degradation enzymes (MMPs), while simultaneously increasing that of type I collagen in epidermoid carcinoma A431 cells. This is the first report to show that these extracts exert synergistic collagen protective effects. Taken together, these findings provide molecular insights into the usefulness of Pomella^® and Maplifa^® or their phenolics as bioactive ingredients for skin care products to slow down aging and enhance skin tone. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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17 pages, 4100 KiB

Open AccessArticle

Analyses of Fatty Acids, Proteins, Ascorbic Acid, Bioactive Phenolic Compounds and Antioxidant Activity of Canadian Barley Cultivars and Elite Germplasm

by Champa Wijekoon, Thomas Netticadan, Ali Sabra, Liping Yu, Chamali Kodikara and Ana Badea

Molecules 2022, 27(22), 7852; https://doi.org/10.3390/molecules27227852 - 14 Nov 2022

Cited by 3 | Viewed by 1704

Abstract

Barley (Hordeum vulgare L.) grain is rich in fiber and antioxidant phytochemicals, including fatty acids, proteins, phenolic compounds, vitamins, and minerals, that offer various health benefits. Research on identifying different barley genotypes based on their health attributes is very limited. In this [...] Read more.

Barley (Hordeum vulgare L.) grain is rich in fiber and antioxidant phytochemicals, including fatty acids, proteins, phenolic compounds, vitamins, and minerals, that offer various health benefits. Research on identifying different barley genotypes based on their health attributes is very limited. In this study, we performed an analysis of fatty acids, proteins, ascorbic acid, phenolic compounds, and antioxidant activity of several Canadian barley cultivars and elite breeding lines. Linoleic acid (C18:2) was the predominant fatty acid present in the tested barley cultivars. The cultivar CDC Bold contained the highest amount of ascorbic acid, while the highest protein content was in CDC Mindon. An assessment of the free and bound phenolic compounds of barley grains showed quantitative changes among different genotypes of Canadian barley. Catechin is the most abundant molecule in free phenolics, while ferulic acid and para-coumeric acid are the most abundant in bound phenolics. Ferulic acid and vanillic acid were molecules detected in the soluble free fraction of all genotypes. Para-coumeric acid was detected only in genotypes such as CDC Copeland, CDC Bold, Lowe, and elite breeding Line 5 of both free and bound fractions of barley. Breeding Line 5 had the lowest antioxidant activity. An analysis of the above molecules and parameters of Canadian barley would help to uncover potential biomarkers in order to distinguish individual barley genotypes. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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19 pages, 1533 KiB

Open AccessArticle

Antibacterial and Antiproliferative Activities of Azadirachta indica Leaf Extract and Its Effect on Oil-in-Water Food Emulsion Stability

by Manel Ouerfelli, Isidoro Metón, Idoia Codina-Torrella and María Pilar Almajano

Molecules 2022, 27(22), 7772; https://doi.org/10.3390/molecules27227772 - 11 Nov 2022

Cited by 1 | Viewed by 1710

Abstract

The present study aims to identify and quantify the phenolic compounds of Azadirachta indica leaf extract using HPLC-MS and to evaluate the antioxidant, antibacterial (against different Gram-positive and negative bacteria) and in vitro anti-proliferative activities of this extract (against breast, human liver and [...] Read more.

The present study aims to identify and quantify the phenolic compounds of Azadirachta indica leaf extract using HPLC-MS and to evaluate the antioxidant, antibacterial (against different Gram-positive and negative bacteria) and in vitro anti-proliferative activities of this extract (against breast, human liver and cervix adenocarcinoma-derived cells). The application of this extract as a natural antioxidant for food preservation was also tested on oil-in-water food emulsions for the first time in the present work in order to determine the use of Azadirachta indica leaves as a natural additive to preserve the food against lipid oxidation and rancidity. The results obtained revealed that 50%-aqueous ethanol leaf extract showed the best extraction yield (25.14%), which was characterized by a high content in phenolic compounds and strong antioxidant activity. Moreover, this leaf extract inhibited the growth of the bacterial strains tested (Staphylococcus aureus, Escherichia coli, Salmonella paratyphi and Micrococcus luteus) and showed better anti-proliferative activity against breast and cervix adenocarcinoma-derived cells than human liver cancer cells after 48 h of treatment. Additionally, Azadirachta indica leaf extract showed almost similar effects as gallic acid solutions (0.25% and 0.5%) in preserving the oxidation of oil-in-water food emulsions and prevented the formation of secondary oxidation products (malondialdehyde) as well. The results obtained suggested that extracts of Azadirachta indica leaves are a potential source of antioxidant and antibacterial compounds and pointed to the potential of these natural extracts as therapeutic agents. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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13 pages, 2111 KiB

Open AccessArticle

Ultrasensitive Determination of Natural Flavonoid Rutin Using an Electrochemical Sensor Based on Metal-Organic Framework CAU−1/Acidified Carbon Nanotubes Composites

by Yuhong Li, Jianxiong Tang, Yueli Lin, Jiejun Li, Yaqi Yang, Pengcheng Zhao, Junjie Fei and Yixi Xie

Molecules 2022, 27(22), 7761; https://doi.org/10.3390/molecules27227761 - 11 Nov 2022

Cited by 19 | Viewed by 2159

Abstract

Rutin, a natural flavonol glycoside, is widely present in plants and foods, such as black tea and wheat tea. The antioxidant and anti-inflammatory effects of flavonoids are well known. In this study, a new electrochemical rutin sensor was developed using multiwalled carbon nanotubes/aluminum-based [...] Read more.

Rutin, a natural flavonol glycoside, is widely present in plants and foods, such as black tea and wheat tea. The antioxidant and anti-inflammatory effects of flavonoids are well known. In this study, a new electrochemical rutin sensor was developed using multiwalled carbon nanotubes/aluminum-based metal–organic frameworks (MWCNT/CAU-1) (CAU−1, a type of Al-MOF) as the electrode modification material. The suspension of multiwalled carbon tubes was dropped on the surface of the GCE electrode to make MWCNT/GCEs, and CAU−1 was then attached to the electrode surface by electrodeposition. MWCNTs and CAU−1 were characterized using scanning electron microscopy (SEM) and X-ray photoelectron spectroscopy (XPS). Due to the synergistic effect of CAU−1 and MWCNT-COOH, the prepared sensor showed an ultrasensitive electrochemical response to rutin. Under optimized conditions, the sensor showed a linear relationship between 1.0 × 10⁻⁹~3.0 × 10⁻⁶ M with a detection limit of 6.7 × 10⁻¹⁰ M (S/N = 3). The sensor also showed satisfactory stability and accuracy in the detection of real samples. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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13 pages, 765 KiB

Open AccessArticle

Phenolic Profile, EPR Determination, and Antiproliferative Activity against Human Cancer Cell Lines of Anthyllis vulneraria Extracts

by Manel Ouerfelli, Isidoro Metón, Idoia Codina-Torrella and María Pilar Almajano

Molecules 2022, 27(21), 7495; https://doi.org/10.3390/molecules27217495 - 3 Nov 2022

Viewed by 1605

Abstract

In the current work, the leaf and flower extracts of Anthyllis vulneraria were evaluated for their chemical characterization using HPLC-MS and for their radical scavenging capacity toward methoxy radicals produced by a Fenton-type reaction using an electron paramagnetic resonance (EPR) spectroscopy assay. The [...] Read more.

In the current work, the leaf and flower extracts of Anthyllis vulneraria were evaluated for their chemical characterization using HPLC-MS and for their radical scavenging capacity toward methoxy radicals produced by a Fenton-type reaction using an electron paramagnetic resonance (EPR) spectroscopy assay. The in vitro antiproliferative activity of these extracts against several human-derived cancer cells (breast: MCF-7; cervical: HeLa; hepatocellular: HepG2) was also evaluated. The results showed that the Anthyllis vulneraria leaf extract was characterized by 17 different phenolic compounds, among which phenolic acids were the most abundant, while its flower extract exhibited higher contents of flavonoids. Furthermore, Anthyllis vulneraria extracts demonstrated a potent radical scavenging activity against methoxy radicals. Both extracts also significantly reduced the viability of the different cancer cell lines. The results of the current study suggested that Anthyllis vulneraria extracts are a promising source of antioxidant compounds with health benefits and pointed to their potential use for treating cancer and developing novel therapeutic agents. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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19 pages, 4116 KiB

Open AccessArticle

Anxiolytic-like Effect of Quercetin Possibly through GABA Receptor Interaction Pathway: In Vivo and In Silico Studies

by Md. Shahazul Islam, Rajib Hossain, Taukir Ahmed, Md. Mizanur Rahaman, Khattab Al-Khafaji, Rasel Ahmed Khan, Chandan Sarkar, Mehedi Hasan Bappi, Edlane Martins de Andrade, Isaac Moura Araújo, Henrique Douglas Melo Coutinho, Grażyna Kowalska, Radosław Kowalski, Muhammad Asif Hanif and Muhammad Torequl Islam

Molecules 2022, 27(21), 7149; https://doi.org/10.3390/molecules27217149 - 22 Oct 2022

Cited by 25 | Viewed by 5459

Abstract

Scientific evidence suggests that quercetin (QUR) has anxiolytic-like effects in experimental animals. However, the mechanism of action responsible for its anxiolytic-like effects is yet to be discovered. The goal of this research is to assess QUR’s anxiolytic effects in mouse models to explicate [...] Read more.

Scientific evidence suggests that quercetin (QUR) has anxiolytic-like effects in experimental animals. However, the mechanism of action responsible for its anxiolytic-like effects is yet to be discovered. The goal of this research is to assess QUR’s anxiolytic effects in mouse models to explicate the possible mechanism of action. After acute intraperitoneal (i.p.) treatment with QUR at a dose of 50 mg/kg (i.p.), behavioral models of open-field, hole board, swing box, and light–dark tests were performed. QUR was combined with a GABAergic agonist (diazepam) and/or antagonist (flumazenil) group. Furthermore, in silico analysis was also conducted to observe the interaction of QUR and GABA (α5), GABA (β1), and GABA (β2) receptors. In the experimental animal model, QUR had an anxiolytic-like effect. QUR, when combined with diazepam (2 mg/kg, i.p.), drastically potentiated an anxiolytic effect of diazepam. QUR is a more highly competitive ligand for the benzodiazepine recognition site that can displace flumazenil (2.5 mg/kg, i.p.). In all the test models, QUR acted similar to diazepam, with enhanced effects of the standard anxiolytic drug, which were reversed by pre-treatment with flumazenil. QUR showed the best interaction with the GABA (α5) receptor compared to the GABA (β1) and GABA (β2) receptors. In conclusion, QUR may exert an anxiolytic-like effect on mice, probably through the GABA-receptor-interacting pathway. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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14 pages, 2944 KiB

Open AccessArticle

Photoprotective Effects of Cannabidiol against Ultraviolet-B-Induced DNA Damage and Autophagy in Human Keratinocyte Cells and Mouse Skin Tissue

by Yanmei Li, Dan Hao, Danfeng Wei, Yue Xiao, Lian Liu, Xiaoxue Li, Lian Wang, Yu Gan, Wei Yan, Bowen Ke and Xian Jiang

Molecules 2022, 27(19), 6740; https://doi.org/10.3390/molecules27196740 - 10 Oct 2022

Cited by 12 | Viewed by 3884

Abstract

Cannabidiol (CBD) has emerged as a phytocannabinoid with various beneficial effects for the skin, including anti-photoaging effects, but its mechanisms of action are not fully elucidated. The study assessed CBD’s photoprotective effects against acute ultraviolet B (UVB)-induced damage in HaCaT human keratinocyte cells [...] Read more.

Cannabidiol (CBD) has emerged as a phytocannabinoid with various beneficial effects for the skin, including anti-photoaging effects, but its mechanisms of action are not fully elucidated. The study assessed CBD’s photoprotective effects against acute ultraviolet B (UVB)-induced damage in HaCaT human keratinocyte cells and murine skin tissue. CBD (8 μM) alleviated UVB-induced cytotoxicity, apoptosis, and G2/M cell cycle arrest in HaCaT cells. The contents of γH2AX and cyclobutane pyrimidine dimers were decreased after CBD treatment. CBD reduced the production of reactive oxygen species and modulated the expression of antioxidant-related proteins such as nuclear factor erythroid 2-related factor 2 in UVB-stimulated HaCaT cells. Furthermore, CBD mitigated the UVB-induced cytotoxicity by activating autophagy. In addition, a cream containing 5% CBD showed effectiveness against UVB-induced photodamage in a murine model. The CBD cream improved the skin’s condition by lowering the photodamage scores, reducing abnormal skin proliferation, and decreasing expression of the inflammation-related protein cyclooxygenase-2 in UVB-irradiated skin tissue. These findings indicate that CBD might be beneficial in alleviating UVB-induced skin damage in humans. The photoprotective effects of CBD might be attributed to its modulatory effects on redox homeostasis and autophagy. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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11 pages, 1421 KiB

Open AccessArticle

Two Novel Sesquiterpenoid Glycosides from the Rhizomes of Atractylodes lancea

by Lanying Liu, Fuqin Guan, Yu Chen, Fan Wang, Pengxu Chen, Min Yin, Bi Wang, Linwei Li, Qizhi Wang, Yonghua Gu and Xu Feng

Molecules 2022, 27(18), 5753; https://doi.org/10.3390/molecules27185753 - 6 Sep 2022

Cited by 4 | Viewed by 2212

Abstract

Secoatractylohexone A (1), an unprecedented secoguaiane lactone glycoside featuring 6/7 cores and dihydroxy-9-guaine-3-one 11-O-β-d-glucopyranoside (2), a 9,10-unsaturated guaiene-type glycoside possessing an uncommon scaffold, were isolated from the water-soluble portion of the ethanolic extract [...] Read more.

Secoatractylohexone A (1), an unprecedented secoguaiane lactone glycoside featuring 6/7 cores and dihydroxy-9-guaine-3-one 11-O-β-d-glucopyranoside (2), a 9,10-unsaturated guaiene-type glycoside possessing an uncommon scaffold, were isolated from the water-soluble portion of the ethanolic extract of Atractylodes lancea rhizomes together with five known compounds (3–7). The structures of 1 and 2 were elucidated on the basis of extensive spectroscopic data and application of the CD technique. The potential biological activities of secoatractylohexone A were predicted by network pharmacology in silico, the result of which indicated that secoatractylohexone A may be used to treat type II diabetes. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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Review

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29 pages, 4510 KiB

Open AccessReview

The Ethnopharmacological, Phytochemical, and Pharmacological Review of Euryale ferox Salisb.: A Chinese Medicine Food Homology

by Jiahui Jiang, Haiyan Ou, Ruiye Chen, Huiyun Lu, Longjian Zhou and Zhiyou Yang

Molecules 2023, 28(11), 4399; https://doi.org/10.3390/molecules28114399 - 28 May 2023

Cited by 7 | Viewed by 4041

Abstract

Euryale ferox Salisb. (prickly water lily) is the only extent of the genus Euryale that has been widely distributed in China, India, Korea, and Japan. The seeds of E. ferox (EFS) have been categorized as superior food for 2000 years in China, based [...] Read more.

Euryale ferox Salisb. (prickly water lily) is the only extent of the genus Euryale that has been widely distributed in China, India, Korea, and Japan. The seeds of E. ferox (EFS) have been categorized as superior food for 2000 years in China, based on their abundant nutrients including polysaccharides, polyphenols, sesquineolignans, tocopherols, cyclic dipeptides, glucosylsterols, cerebrosides, and triterpenoids. These constituents exert multiple pharmacological effects, such as antioxidant, hypoglycemic, cardioprotective, antibacterial, anticancer, antidepression, and hepatoprotective properties. There are very few summarized reports on E. ferox, albeit with its high nutritional value and beneficial activities. Therefore, we collected the reported literature (since 1980), medical classics, database, and pharmacopeia of E. ferox, and summarized the botanical classification, traditional uses, phytochemicals, and pharmacological effects of E. ferox, which will provide new insights for further research and development of EFS-derived functional products. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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39 pages, 17908 KiB

Open AccessReview

A Comprehensive Review on Pharmacologically Active Phyto-Constituents from Hedychium species

by Alok Pratap Singh, Havagiray Chitme, Rajeev Kumar Sharma, JB Kandpal, Ashok Behera, Basel A. Abdel-Wahab, Mohammed Abdelmalek Orabi, Masood Medleri Khateeb, Mohammed Shafiuddin Habeeb and Marwa B. Bakir

Molecules 2023, 28(7), 3278; https://doi.org/10.3390/molecules28073278 - 6 Apr 2023

Cited by 4 | Viewed by 3870

Abstract

In this review, we describe and discuss the phytoconstituents present in Hedychium species and emphasize their potential as drug candidates. Though they are widely validated in vitro and in vivo models, to date, no efforts have been made to compile in a single [...] Read more.

In this review, we describe and discuss the phytoconstituents present in Hedychium species and emphasize their potential as drug candidates. Though they are widely validated in vitro and in vivo models, to date, no efforts have been made to compile in a single review all the pharmacologically active phytoconstituents from Hedychium species, and their pharmacological and toxicity profile. In this study, we present a reinvestigation of the chemical constituents present in Hedychium species obtained from the essential oil and solvent extraction of the flowers, leaves and rhizomes under consideration. Key databases such as PubMed, Science Direct, Scopus, and Google Scholar amongst others were probed for a systematic search using keywords to retrieve relevant publications on this plant. An exhaustive electronic survey of the related literature on Hedychium species resulted in around 200 articles. Articles published between the years 1975–2021 were included. The studies conducted on either crude extracts, solvent fractions or isolated pure compounds from Hedychium species reported with a varied range of biological effects such as anti-inflammatory, analgesic, antidiabetic, potentially anti-asthmatic, and cytotoxic, among other related activities of the chemical constituents present in its essential oil and solvent extract deployed in this review. Traditional and herbal medication around the world that uses different parts of Hedychium species were considered for anti-inflammatory, skincare, analgesic, anti-asthmatic, anti-diabetic, antidotal uses, among others. These uses support the idea that chemical constituents obtained from solvent extraction may also exert the same action individually or in a synergistic manner. The review concluded that there is scope for computation and biological study to find out possible new targets for strengthening the potency and selectivity of the relevant compounds, and to find a commercial method for extraction of active pharmaceutical ingredients. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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46 pages, 3288 KiB

Open AccessReview

Allii Macrostemonis Bulbus: A Comprehensive Review of Ethnopharmacology, Phytochemistry and Pharmacology

by Jianfa Wu, Lulu Wang, Ying Cui, Fei Liu and Jing Zhang

Molecules 2023, 28(6), 2485; https://doi.org/10.3390/molecules28062485 - 8 Mar 2023

Cited by 12 | Viewed by 2860

Abstract

The dried bulbs of Allii Macrostemonis Bulbus (AMB) are called “薤白” in China and are mainly distributed in Asia. The plant species included in the 2020 Edition of the Chinese Pharmacopoeia (ChP) are Allium macrostemon Bunge (called xiaogensuan in Chinese, A. macrostemon) [...] Read more.

The dried bulbs of Allii Macrostemonis Bulbus (AMB) are called “薤白” in China and are mainly distributed in Asia. The plant species included in the 2020 Edition of the Chinese Pharmacopoeia (ChP) are Allium macrostemon Bunge (called xiaogensuan in Chinese, A. macrostemon) and Allium chinense G. Don (called xie in Chinese, A. chinense), respectively. In the traditional Chinese medicine (TCM) theoretical system, AMB is warm in nature, acrid-bitter taste, and attributive to the heart, lung, stomach, large intestine meridian. AMB has the function of activating Yang and removing stasis, regulating Qi and eliminating stagnation. Modern pharmacological studies have shown that AMB has anti-platelet aggregation, hypolipidemic, anti-atherosclerotic, cardiomyocyte, vascular endothelial cell protection, anti-cancer, anti-bacterial, anti-asthmatic, and anti-oxidant effects. In some Asian countries, AMB is often used to treat coronary heart disease (CHD), angina pectoris (AP), asthma, and diarrhea. This review collates the botanical background, ethnopharmacology, phytochemistry, pharmacological activities, quality control, and toxicological studies of AMB, and provides an outlook on the current research deficiencies and future research priorities of AMB, intending to provide ideas for future research directions and commercial development. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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23 pages, 2212 KiB

Open AccessReview

The Impact of Compounds Extracted from Wood on the Quality of Alcoholic Beverages

by Tomasz Tarko, Filip Krankowski and Aleksandra Duda-Chodak

Molecules 2023, 28(2), 620; https://doi.org/10.3390/molecules28020620 - 7 Jan 2023

Cited by 18 | Viewed by 4748

Abstract

The production of some alcoholic beverages very often requires the use of wood from various tree species to improve the quality parameters (smell, taste, and color) of the drink. The review discusses the types of wood used in the production of wines, beers, [...] Read more.

The production of some alcoholic beverages very often requires the use of wood from various tree species to improve the quality parameters (smell, taste, and color) of the drink. The review discusses the types of wood used in the production of wines, beers, and flavored vodkas. Changes occurring in wood during the process of toasting barrels or wood chips are described. The compounds derived from wood that shape the aroma, taste, and color of alcoholic beverages are presented. Depending on their origin, they were classified into compounds naturally occurring in wood and those formed as a result of the thermal treatment of wood. Next, the influence of the presence of wood on the quality of alcoholic beverages was described, with particular emphasis on wine, beer, whisky, and brandy. The final part of the article presents innovative techniques using wood to impart qualitative features to alcoholic beverages. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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15 pages, 601 KiB

Open AccessFeature PaperReview

The Biomedical Importance of the Missing Pathway for Farnesol and Geranylgeraniol Salvage

by Ignasi Bofill Verdaguer, Marcell Crispim, Agustín Hernández and Alejandro Miguel Katzin

Molecules 2022, 27(24), 8691; https://doi.org/10.3390/molecules27248691 - 8 Dec 2022

Cited by 11 | Viewed by 3351

Abstract

Isoprenoids are the output of the polymerization of five-carbon, branched isoprenic chains derived from isopentenyl pyrophosphate (IPP) and its isomer, dimethylallyl pyrophosphate (DMAPP). Isoprene units are consecutively condensed to form longer structures such as farnesyl and geranylgeranyl pyrophosphate (FPP and GGPP, respectively), necessary [...] Read more.

Isoprenoids are the output of the polymerization of five-carbon, branched isoprenic chains derived from isopentenyl pyrophosphate (IPP) and its isomer, dimethylallyl pyrophosphate (DMAPP). Isoprene units are consecutively condensed to form longer structures such as farnesyl and geranylgeranyl pyrophosphate (FPP and GGPP, respectively), necessary for the biosynthesis of several metabolites. Polyprenyl transferases and synthases use polyprenyl pyrophosphates as their natural substrates; however, it is known that free polyprenols, such as farnesol (FOH), and geranylgeraniol (GGOH) can be incorporated into prenylated proteins, ubiquinone, cholesterol, and dolichols. Furthermore, FOH and GGOH have been shown to block the effects of isoprenoid biosynthesis inhibitors such as fosmidomycin, bisphosphonates, or statins in several organisms. This phenomenon is the consequence of a short pathway, which was observed for the first time more than 25 years ago: the polyprenol salvage pathway, which works via the phosphorylation of FOH and GGOH. Biochemical studies in bacteria, animals, and plants suggest that this pathway can be carried out by two enzymes: a polyprenol kinase and a polyprenyl-phosphate kinase. However, to date, only a few genes have been unequivocally identified to encode these enzymes in photosynthetic organisms. Nevertheless, pieces of evidence for the importance of this pathway abound in studies related to infectious diseases, cancer, dyslipidemias, and nutrition, and to the mitigation of the secondary effects of several drugs. Furthermore, nowadays it is known that both FOH and GGOH can be incorporated via dietary sources that produce various biological effects. This review presents, in a simplified but comprehensive manner, the most important data on the FOH and GGOH salvage pathway, stressing its biomedical importance The main objective of this review is to bring to light the need to discover and characterize the kinases associated with the isoprenoid salvage pathway in animals and pathogens. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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68 pages, 7135 KiB

Open AccessReview

Resin Glycosides from Convolvulaceae Family: An Update

by Rani Maharani, Mohamad Fajar and Unang Supratman

Molecules 2022, 27(23), 8161; https://doi.org/10.3390/molecules27238161 - 23 Nov 2022

Cited by 4 | Viewed by 2638

Abstract

Resin glycoside is a type of secondary metabolite isolated commonly from the Convolvulaceae family. It consists of oligosaccharides conjugated to organic acids with a larger percentage having a macrocyclic structure. The resin glycosides reported in this review is classified mostly based on the [...] Read more.

Resin glycoside is a type of secondary metabolite isolated commonly from the Convolvulaceae family. It consists of oligosaccharides conjugated to organic acids with a larger percentage having a macrocyclic structure. The resin glycosides reported in this review is classified mostly based on the number of sugar units constructing the structure, which is correlated to the biological properties of the compounds. According to preliminary reviews, the protocols to isolate the compounds are not straightforward and require a special technique. Additionally, the structural determination of the isolated compounds needs to minimize the structure for the elucidation to become easier. Even though resin glycosides have a complicated structural skeleton, several total syntheses of the compounds have been reported in articles published from 2010 to date. This review is an update on the prior studies of the resin glycosides reported in 2010 and 2017. The review includes the classification, isolation techniques, structural determination, biological properties, and total synthesis of the resin glycosides. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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22 pages, 399 KiB

Open AccessReview

Bioactive Compounds, Pharmacological Actions, and Pharmacokinetics of Genus Acacia

by Gaber El-Saber Batiha, Nosheen Akhtar, Abdulrahman A. Alsayegh, Wafaa Fouzi Abusudah, Najlaa Hamed Almohmadi, Hazem M. Shaheen, Thakur Gurjeet Singh and Michel De Waard

Molecules 2022, 27(21), 7340; https://doi.org/10.3390/molecules27217340 - 28 Oct 2022

Cited by 21 | Viewed by 5347

Abstract

Plants are a promising source of bioactive compounds that can be used to tackle many emerging diseases both infectious and non-infectious. Among different plants, Acacia is a very large genus and exhibits a diverse array of bioactive agents with remarkable pharmacological properties against [...] Read more.

Plants are a promising source of bioactive compounds that can be used to tackle many emerging diseases both infectious and non-infectious. Among different plants, Acacia is a very large genus and exhibits a diverse array of bioactive agents with remarkable pharmacological properties against different diseases. Acacia, a herb found all over the world, contains approximately more than 1200 species of the Fabaceae family. In the present review, we have collected detailed information on biochemical as well as pharmacological properties. The data were retrieved using different databases, such as Elsevier, PubMed, Science Direct, Google Scholar, and Scopus, and an extensive literature survey was carried out. Studies have shown that Acacia possesses several secondary metabolites, including amines, cyanogenic glycosides, flavonoids, alkaloids, seed oils, cyclitols, fluoroacetate, gums, non-protein amino acids, diterpenes, fatty acids, terpenes, hydrolyzable tannins, and condensed tannins. These compounds exhibit a wide range of pharmaceutical applications such as anti-inflammatory, antioxidant, antidiarrheal, antidiabetic, anticancer, antiviral, liver protective effects, and so on. Thus, the literature shows the tremendous phytochemical impact of the genus Acacia in medicine. Overall, we recommend that more research should be conducted on the medicinal value and isolation and purification of the effective therapeutic agents from Acacia species for the treatment of various ailments. Full article

(This article belongs to the Special Issue Advances on Natural Products: Isolation, Identification and Biological Activity)

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