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Antimycobacterial Serratamolides and Diacyl Peptoglucosamine Derivatives from Serratia sp.

Deepti Dwivedi^†^‡, Rolf Jansen^§, Gabriella Molinari, Manfred Nimtz^†, Bhavdish N Johri and Victor Wray*^†

Department of Structural Biology, Microbial Drugs Group, and Environmental Microbiology Group, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, D-38124, Braunschweig, Germany, and Department of Biotechnology and Bioinformatics, Barkatulla University, Bhopal, India

J. Nat. Prod., 2008, 71 (4), pp 637–641

DOI: 10.1021/np7007126

Publication Date (Web): February 28, 2008

†

Department of Structural Biology, Helmholtz Centre for Infection Research.

‡

Present address: Laboratory of Molecular Genetics, National Institute of Environmental Health Sciences, Research Triangle Park, NC 27709.

Microbial Drugs Group, Helmholtz Centre for Infection Research.

Environmental Microbiology Group, Helmholtz Centre for Infection Research.

Barkatulla University.

* To whom correspondence should be addressed. Tel: 0049/531-61817200 . Fax: 0049/531-6181-7099. E-mail: victor.wray@helmholtz-hzi.de.

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 C₁₀ alkyl chains, its derivatives always contained one C₁₀ chain combined with either C_12:1, C₁₂, C₁₁, C₉, or C₈ chains. The glucosamine derivatives contained a common core consisting of an N-butyl-α-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, C₁₅, or C₁₄. 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.