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Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

ABSTRACT: Five new antibacterial ambiguine K-O isonitriles (1-5) and eight previously described indole alkaloids were isolated from the cultured cyanobacterium Fischerella ambigua (UTEX 1903) by bioassay-guided fractionation. The planar structures of the new compounds were determined by spectroscopic analysis including MS and 1D and 2D NMR. X-ray crystallography was used to determine the absolute stereoconfiguration of ambiguine K isonitrile. The isolates were evaluated for their antibacterial activities against a set of bacterial targets, including Mycobacterium tuberculosis and Bacillus anthracis. Ambiguine K and M isonitriles showed the most potent activity against M. tuberculosis, with MIC values of 6.6 and 7.5 microM, respectively. Ambiguine A isonitrile showed the most potent activity against B. anthracis, with a MIC of 1.0 microM.

SUBMITTER: Mo S

PROVIDER: S-EPMC2765494 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua.

Mo Shunyan S Krunic Aleksej A Chlipala George G Orjala Jimmy J

Journal of natural products 20090501 5

Five new antibacterial ambiguine K-O isonitriles (1-5) and eight previously described indole alkaloids were isolated from the cultured cyanobacterium Fischerella ambigua (UTEX 1903) by bioassay-guided fractionation. The planar structures of the new compounds were determined by spectroscopic analysis including MS and 1D and 2D NMR. X-ray crystallography was used to determine the absolute stereoconfiguration of ambiguine K isonitrile. The isolates were evaluated for their antibacterial activities ...[more]

PMID: 19371071

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