Antimycobacterial serratamolides and diacyl peptoglucosamine derivatives from Serratia sp.
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.
Dwivedi
Deepti
D
Department of Structural Biology, Helmholtz Centre for Infection Research, Inhoffenstrasse 7, D-38124, Braunschweig, Germany.
Jansen
Rolf
R
Molinari
Gabriella
G
Nimtz
Manfred
M
Johri
Bhavdish N
BN
Wray
Victor
V
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D047630:Depsipeptides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D005227:Fatty Acids / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects*; D012705:Serratia
D000900:Anti-Bacterial Agents; D047630:Depsipeptides; D005227:Fatty Acids; C529471:serratamolide A