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Nat Prod Res. 2014;28(12):861-7. doi: 10.1080/14786419.2014.886210. Epub 2014 Feb 25.

Two novel amphomycin analogues from Streptomyces canus strain FIM-0916.

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1
a Department of Pharmaceutical Microbiology, Fujian Institute of Microbiology , Fuzhou 350007 , P.R. China.

Abstract

Three lipopeptides, the known compound amphomycin, together with two novel compounds named aspartocin D (1) and aspartocin E (2) were obtained from the fermentation broth extraction of Streptomyces canus strain FIM0916 by using various column chromatography techniques. Their structures were elucidated by using spectroscopic methods, mainly by an extensive NMR analysis. It was demonstrated that compounds 1 and 2 are novel analogues of amphomycin, whose structures are similar to aspartocins. Compounds 1 and 2 share the same cyclic decapeptide core of cyclo (Dab2-Pip3-MeAsp4-Asp5-Gly6-Asp7-Gly8-Dab9-Val10-Pro11-), differing only in the side-chain moiety corresponding to Asp1-△3-isohendecenoic acid and Asp1-△3-isododecenoic acid, for aspartocin D and aspartocin E. In bioassays, compounds 1 and 2 exhibited antimicrobial activities against Gram-positive bacteria in the presence of Ca(2+) (1.25 mM); particularly, the activities were enhanced with higher concentrations of calcium.

KEYWORDS:

NMR spectroscopy; amphomycins; aspartocins; lipopeptide antibiotics; structure elucidation

PMID:
24568288
DOI:
10.1080/14786419.2014.886210
[Indexed for MEDLINE]
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