| 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. |
- Doorandishan, Mina, et al.
(författare)
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Molecular docking and simulation studies of a novel labdane type-diterpene from Moluccella aucheri Scheen (Syn. Otostegia aucheri) as human-AChE inhibitor
- 2021
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Ingår i: Journal of Molecular Structure. - : Elsevier. - 0022-2860 .- 1872-8014. ; 1245
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Tidskriftsartikel (refereegranskat)abstract
- Moluccella aucheri Scheen belongs to Lamiaceae family and is native to Iran and Pakistan. Different chromatographic and spectroscopic analyses of a dichloromethane extract of M. aucheri's aerial parts led to the isolation of five phytochemicals. They include an undescribed labdane typediterpene; 6 beta-acetoxy-9 alpha-hydroxy-7-oxa-labd-13-ene-15, 16-olide or moluccelactone (1), and four known compounds: stigmasterol and beta-sitosterol (2, 3), 5-hydroxy-7, 4'-dimethoxyflavone (4) and genkwanin (5). Their chemical structures were determined by spectroscopic data. As a best result, these compounds are firstly reported in this genus and plant. The alpha-glucosidase and acetylcholine esterase (AChE) inhibitory activity of 1 were evaluated by the protein-ligand docking and molecular dynamics studies. Compound 1 exhibited strong binding affinities towards the active site residues of human-AChE (hAChE) enzyme, while it was not potent against alpha-glucosidase enzyme. In conclusion, compound 1 is suggested as a potential natural inhibitor of hAChE enzyme in vitro and in vivo tests. (C) 2021 Elsevier B.V. All rights reserved.
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| 4. |
- Ghoran, Salar Hafez, et al.
(författare)
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Sappanin-type homoisoflavonoids from Scilla bisotunensis Speta. : Cytotoxicity, molecular docking, and chemotaxonomic significance
- 2023
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Ingår i: Journal of Molecular Structure. - : Elsevier. - 0022-2860 .- 1872-8014. ; 1273
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Tidskriftsartikel (refereegranskat)abstract
- Phytochemical investigation of the chloroform extract of Scilla bisotunensis Speta. bulbs led to the isolation and structure elucidation of six sappinane-4-one ( 1-4, 7, 9 ) and three 3,9-dehydrosappinan-4-one ( 5, 6, 8 ) homoisoflavonoids. The structures of compounds 1 -9 were established based on extensive NMR, ESIMS, UV, and ECD spectra, and also by comparison with the previously reported spectroscopic data. The in vitro cytotoxicity of sappanin-type homoisoflavonoids 1 -9 was assayed against HT-29 human colorectal cancer cells using sulforhodamine B assay. Compounds 8 and 9 showed higher cytotoxic effects with IC50 of 5.3 and 6.1 mu g/mL, respectively, while compounds 3, 5 , and 7 exhibited moderate activity with IC50 ranging from 25 to 37 mu g/mL. Interestingly, molecular docking studies revealed that compounds 1-9 could be potential sarcoma kinase domain inhibitors with binding energies ranging from -7.37 ( 6 ) to -8.34 ( 9 ) kcal/mol when compared with the native inhibitor, purvalanol A of -7.90 kcal/mol. All homoisoflavonoids, except 1 and 5 are reported for the first time in a member of the Scilla genus, while, to the best of our knowledge this is the first phytochemical and biological study on S. bisotunensis. The plant exhibited good chemotaxonomic relationships to the genus Eucomis L'Her. on the basis of comparing their chemical constituents with those reported in the related plant families.
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| 5. |
- Jassbi, Amir Reza, et al.
(författare)
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Cytotoxic abietane-type diterpenoids from roots of Salvia spinosa and their in Silico pharmacophore modeling
- 2022
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Ingår i: Natural Product Research. - : Informa UK Limited. - 1478-6419 .- 1478-6427. ; 36:12, s. 3183-3188
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Tidskriftsartikel (refereegranskat)abstract
- The roots of Salvia spinosa L. (Lamiaceae) were extracted withhexane, dichloromethane (DCM) and ethyl acetate. The DCMextract exhibited cytotoxic activity (IC50 32.7 mg/mL) against MFC7 breast cancer cell line in MTT colorimetric bioassay. Ferruginol(1), taxodione (2), 12-deoxy-6-hydroxy-6,7-dehydroroyleanone (3),14-deoxycoleon U (4), 15-deoxyfuerstione (5) and taxodone (6)were isolated from the DCM roots extract. Their structures wereelucidated by a combination of spectroscopic analyses includingEIMS and 1H- and 13C NMR spectra. The cytotoxicity of compound3 was determined against MCF-7 and K562 cell lines and compared with the other compounds. A pharmacophore model wasbuilt based on potent input compounds to resolve importantpharmacophore features responsible for cytotoxic activity of theisolated compounds
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