Three 1-thio-beta-D-glucopyranosides from the seeds of Afrostyrax lepidophyllus Mildbr

Annie Ngono Ngane; Marie Lavault; Denis Séraphin; Anne Landreau; Pascal Richomme

doi:10.1016/j.carres.2006.09.021

Three 1-thio-beta-D-glucopyranosides from the seeds of Afrostyrax lepidophyllus Mildbr

Carbohydr Res. 2006 Dec 11;341(17):2799-802. doi: 10.1016/j.carres.2006.09.021. Epub 2006 Oct 4.

Authors

Annie Ngono Ngane¹, Marie Lavault, Denis Séraphin, Anne Landreau, Pascal Richomme

Affiliation

¹ SONAS, UFR des Sciences Pharmaceutiques, 16, Bd Daviers, F-49100 Angers, France.

PMID: 17054924
DOI: 10.1016/j.carres.2006.09.021

Abstract

Three new 1-thioglycosides namely methylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside A), methylsulfonylmethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside B) and methylsulfonylmethylthiomethyl 1-thio-beta-D-glucopyranoside (Afrostyraxthioside C) were isolated from the seeds of Afrostyrax lepidophyllus Mildbr. Their structures were mainly elucidated by using one- and two-dimensional NMR and mass spectroscopies and also by an efficient one-step synthesis. Moreover, Afrostyraxthiosides A, B and C constitute a new subclass of 1-thioglycosides isolated from natural sources.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antifungal Agents / isolation & purification*
Antifungal Agents / pharmacology
Candida albicans / drug effects
Candida glabrata / drug effects
Chromatography / methods
Magnetic Resonance Spectroscopy / methods
Magnoliopsida / chemistry*
Seeds / chemistry*
Spectrometry, Mass, Fast Atom Bombardment / methods
Thioglucosides / isolation & purification*
Thioglucosides / pharmacology

Substances

Antifungal Agents
Thioglucosides
methylsulfonylmethyl 1-thioglucopyranoside
methylsulfonylmethylthiomethyl 1-thioglucopyranoside
methylthiomethyl 1-thioglucopyranoside