| 1. |
- Zare, Somayeh, et al.
(författare)
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Anti-COVID-19 and antidiabetic activities of new oleanane and ursane-type triterpenoids from Salvia grossheimii : an in-silico approach
- 2022
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Ingår i: Journal of Receptor and Signal Transduction Research. - : Taylor & Francis Group. - 1079-9893 .- 1532-4281. ; 42:6, s. 540-548
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Tidskriftsartikel (refereegranskat)abstract
- Salvia grossheimii is a perennial herb with antidiabetic and cytotoxic constituents. In continuation of our study on S. grosshiemii to identify the bioactive phytochemicals, we have reported the characterization of seven undescribed triterpenoids. The aerial parts of the plant were extracted in dichloromethane and its constituents were isolated using chromatography techniques. The structures of compounds were identified using 1D, 2D NMR, and ESI-MS spectral data. Seven new oleanane- and ursane-type triterpenoids (1-7) were identified in S. grossheimii. The structures of 1-7 were characterized as; 2 alpha-hydroxy-3 beta-acetoxy-olean-9(11),12-diene (1), 2 alpha-acetoxy-3 beta-hydroxy-olean-9(11),12-diene (2), 3 beta-acetoxy-olean-18-ene,2 alpha,11 alpha-diol (3), 2 alpha-hydroxy-3 beta-acetoxy-urs-9(11),12-diene (4), 2 alpha-acetoxy-3 beta-hydroxy-urs-9(11),12-diene (5), 2 alpha,3 beta-diacetoxy-urs-12-ene-11 alpha,20 beta-diol (6), 2 alpha,3 beta-diacetoxy-urs-9(11),12-diene-20 beta-ol (7). Triterpenoids (2, 5, and 7) were intramolecular transesterification or dehydration products of their corresponding isomers or allylic alcohol in the C rings, respectively, produced in-situ during NMR spectroscopy. Virtual screening of 1-7 was performed with molecular docking analysis to identify the potential SARS-CoV-2 and alpha-glucosidase inhibitors using the smina molecular docking algorithm. The best binding energy values (kcal/mol) against COVID-19 main protease M-pro were calculated for 6 (-8.77) and 7 (-8.68), and the higher binding affinities toward human alpha-glucosidase were obtained for 2 (-9.39) and 6 (-8.63). This study suggests S. grossheimii as a rich source of bioactive triterpenoids and introduces new natural compounds. Considering the high binding energy values of 2, 6, and 7, these structures could be candidates for anti-COVID-19 and antidiabetic drug development in the future.
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| 2. |
- Zare, Somayeh, et al.
(författare)
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Antidiabetic and cytotoxic polyhydroxylated oleanane and ursane type triterpenoids from Salvia grossheimii
- 2020
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Ingår i: Bioorganic chemistry. - : Elsevier BV. - 0045-2068. ; 104
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Tidskriftsartikel (refereegranskat)abstract
- Two polyhydroxylated oleanane and seven ursane triterpenoids were isolated from aerial parts of Salvia grossheimii. The chemical structures of the undescribed triterpenoids (1–6) were characterized using 1 and 2 D NMR and ESI-MS spectral data as; 2α, 3β, 11α –trihydroxy-olean-12- ene (1), 2α, 3β, 11α-trihydroxy-olean-18-ene (2), 2α- acetoxy-urs-12-ene-3β, 11α, 20β-triol (3), 3-keto-urs-12-ene-1β, 11α, 20β -triol (4), 2α, 3β-diacetoxy-urs-12-ene-1β, 11α, 20β -triol (5), and 3β-acetoxy-urs-12-ene-1β, 11α, 20β –triol (6). All compounds were evaluated for the in vitro α-glucosidase inhibitory and cytotoxic activities against MCF-7 human cancer cell line. Compounds 1, 2, 4, and 6 showed in vitro α-glucosidase inhibitory activity with IC50 = 43.6–198.4 µM, which were more potent than the antidiabetic medicine, acarbose. The remaining compounds; 3, and 7–9 showed potent cytotoxic activity (IC50 = 6.2–31.9 µM) against the cancerous cell line, while the potent α-glucosidase inhibitors were inactive. Molecular docking analysis and kinetic studies were applied to investigate the structure activity relationships and mechanisms of the human and Saccharomyces cerevisiae α-glucosidase inhibitory of the purified compounds. Comparing the high cytotoxicity and α-glucosidase inhibitory of the oleanane and ursane type triterpenoids suggest them as potential lead compounds for further research in anticancer and antidiabetic research.
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| 3. |
- Jassbi, Amir Reza, et al.
(författare)
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Ecological Roles and Biological Activities of Specialized Metabolites from the Genus Nicotiana
- 2017
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Ingår i: Chemical Reviews. - : American Chemical Society (ACS). - 0009-2665 .- 1520-6890. ; 117:19, s. 12227-12280
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Forskningsöversikt (refereegranskat)abstract
- Species of Nicotiana grow naturally in different parts of the world and have long been used both medicinally and recreationally by human societies. More recently in our history, Nicotiana tabacum has attracted interest as one of the most economically important industrial crops. Nicotiana species are frequently investigated for their bioactive natural products, and the ecological role of their specialized metabolites in responses to abiotic stress or biotic stress factors like pathogens and herbivores. The interest of tobacco companies in genetic information as well as the success of a few wild tobacco species as experimental model organisms have resulted in growing knowledge about the molecular biology and ecology of these plants and functional studies of the plant’s natural products. Although a large number of reviews and books on biologically active natural products already exists, mostly from N. tabacum, we focus our attention on the ecological roles and biological activity of natural products, versus products from cured and processed material, in this Review. The studied compounds include alkaloids, aromatic compounds, flavonoids, volatiles, sesquiterpenoids, diterpenes alcohols, and sugar esters from trichomes of the plants, and recently characterized acyclic hydroxygeranyllinalool diterpene glycosides (HGL-DTGs). In this Review (1800s–2017), we describe the above-mentioned classes of natural products, emphasizing their biological activities and functions as they have been determined either in bioassay-guided purification approaches or in bioassays with plants in which the expression of specific biosynthetic genes has been genetically manipulated. Additionally, a review on the history, taxonomy, ecology, and medicinal application of different Nicotiana species growing around the globe presented in this Review may be of interest for pharmacognosists, natural products, and ecological chemists.
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