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Chlorinated Withanolides from Withania somnifera.

ABSTRACT: A chlorinated withanolide, 6?-chloro-5?,17?-dihydroxywithaferin A (1), and nine known withanolides, 6?-chloro-5?-hydroxywithaferin A (2), (22R)-5?-formyl-6?,27-dihydroxy-1-oxo-4-norwith-24-enolide, withaferin A, 2,3-dihydrowithaferin A, 3-methoxy-2,3-dihydrowithaferin A, 2,3-didehydrosomnifericin, withanone, withanoside IV and withanoside X, were isolated from Withania somnifera (Solanaceae). All structures were elucidated on the basis of spectroscopic methods (IR, HRESIMS, 1D/2D NMR). X-ray crystallography confirmed the absolute configuration of 1.

SUBMITTER: Tong X

PROVIDER: S-EPMC3223914 | biostudies-literature | 2011 Dec

REPOSITORIES: biostudies-literature

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Chlorinated Withanolides from Withania somnifera.

Tong Xiaoqin X Zhang Huaping H Timmermann Barbara N BN

Phytochemistry letters 20111201 4

A chlorinated withanolide, 6α-chloro-5β,17α-dihydroxywithaferin A (1), and nine known withanolides, 6α-chloro-5β-hydroxywithaferin A (2), (22R)-5β-formyl-6β,27-dihydroxy-1-oxo-4-norwith-24-enolide, withaferin A, 2,3-dihydrowithaferin A, 3-methoxy-2,3-dihydrowithaferin A, 2,3-didehydrosomnifericin, withanone, withanoside IV and withanoside X, were isolated from Withania somnifera (Solanaceae). All structures were elucidated on the basis of spectroscopic methods (IR, HRESIMS, 1D/2D NMR). X-ray cry ...[more]

PMID: 22125584

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Comparative interactions of withanolides and sterols with two members of sterol glycosyltransferases from Withania somnifera.

Project description:BackgroundSterol glycosyltransferases (SGTs) are ubiquitous but one of the most diverse group of enzymes of glycosyltransferases family. Members of this family modulate physical and chemical properties of secondary plant products important for various physiological processes. The role of SGTs has been demonstrated in the biosynthesis of pharmaceutically important molecules of medicinal plants like Withania somnifera.ResultsAnalysis suggested conserved behaviour and high similarity in active sites of WsSGTs with other plant GTs. Substrate specificity of WsSGTs were analysed through docking performance of WsSGTs with different substrates (sterols and withanolides). Best docking results of WsSGTL1 in the form of stable enzyme-substrate complex having lowest binding energies were obtained with brassicasterol, transandrosteron and WsSGTL4 with solasodine, stigmasterol and 24-methylene cholesterol.ConclusionThis study reveals topological characters and conserved nature of two SGTs from W. somnifera (WsSGTs) i.e. WsSGTL1 and WsSGTL4. However, besides being ubiquitous in nature and with broad substrate specificity, difference between WsSGTL1 and WsSGTL4 is briefly described by difference in stability (binding energy) of enzyme-substrate complexes through comparative docking.

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Identification of anti-adipogenic withanolides from the roots of Indian ginseng (<i>Withania somnifera</i>).

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