Antimycobacterial serratamolides and diacyl peptoglucosamine derivatives from Serratia sp.

Basic Information

ID: ALA1149852

Journal: J Nat Prod

Title: Antimycobacterial serratamolides and diacyl peptoglucosamine derivatives from Serratia sp.

Authors: Dwivedi D, Jansen R, Molinari G, Nimtz M, Johri BN, Wray V.

Abstract: The cyclodepsipeptide serratamolide A ( 1) and five closely related compounds together with three new glucosamine derivatives were isolated by bioactivity-guided chromatography from the XAD adsorber resin extract of a Serratia sp. The structures of the compounds were elucidated by 2D NMR and MS analyses. In addition to the known serratamolide A ( 1) with two C 10 alkyl chains, its derivatives always contained one C 10 chain combined with either C 12:1, C 12, C 11, C 9, or C 8 chains. The glucosamine derivatives contained a common core consisting of an N-butyl-alpha-glucopyranosylamide, which was acylated at the C-1 oxygen with valine. The differences between the derivatives arise from the nature of the acyl groups attached to the N-terminus of valine, which were identified as the linear fatty acid moieties C 16:1, C 15, or C 14. Each compound was present in two isomeric forms arising from racemization of the valine moiety. All compounds showed antibiotic activity against Mycobacterium diernhoferi and other rapidly growing mycobacteria.

CiteXplore: 18303848

DOI: 10.1021/np7007126

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