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Pachymoside A - A novel glycolipid isolated from the marine sponge Pachymatisma johnstonia

TitlePachymoside A - A novel glycolipid isolated from the marine sponge Pachymatisma johnstonia
Publication TypeJournal Article
Year of Publication2004
AuthorsWarabi, K, Zimmerman, WT, Shen, JK, Gauthier, A, Robertson, M, Finlay, BB, Van Soest, R, Andersen, RJ
JournalCanadian Journal of Chemistry-Revue Canadienne De Chimie
Volume82
Pagination102-112
Date PublishedFeb
Type of ArticleArticle
ISBN Number0008-4042
KeywordsBACTERIAL VIRULENCE, ENTEROPATHOGENIC ESCHERICHIA-COLI, glycolipid, GLYCOSPHINGOLIPIDS, HOST-CELLS, III SECRETION, inhibitors, marine sponge, NATURAL-PRODUCTS, Pachymatisma johnstonia, pachymoside, PLAKORTIS-SIMPLEX, PLAKOSIDE, PRENYLATED, RECEPTOR
Abstract

Crude extracts of the North Sea marine sponge Pachymatisma johnstonia showed promising activity in a new assay for inhibitors of bacterial type III secretion. Bioassay-guided fractionation resulted in the isolation of the pachymosides, a new family of sponge glycolipids. A major part of the structural diversity in this family of glycolipids involves increasing degrees of acetylation and differing positions of acetylation on a common pachymoside glycolipid template. All of the metabolites with these variations in acetylation pattern were converted into the same peracetylpachymoside methyl ester (2) for purification and spectroscopic analysis. Pachymoside A (1) is the component of the mixture that has natural acetylation at the eight galactose hydroxyls and at the C-6 hydroxyls of glucose-B and glucose-D. Chemical degradation and transformation in conjunction with extensive analysis of 800 MHz NMR data was used to elucidate the structure of pachymoside A (1).

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