Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 May 22;72(5):894-9.
doi: 10.1021/np800751j.

Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua

Shunyan Mo  1 , Aleksej Krunic, George Chlipala, Jimmy Orjala
Affiliations

Antimicrobial ambiguine isonitriles from the cyanobacterium Fischerella ambigua

Shunyan Mo et al. J Nat Prod. .

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.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Key HMBC and COSY correlations of ambiguine K isonitrile (1)
Figure 2
Figure 2
The ORTEP diagram of ambiguine K isonitrile (1)
Figure 3
Figure 3
Structure and key HMBC correlations of the 1-hydroxy-3, 3-dimethyl-2-propanone moiety
None
See this image and copyright information in PMC

References

    1. Mundt S, Kreitlow S, Nowotny A, Effmert U. Int. J. Hyg. Envir. Heal. 2001;203:327–334. - PubMed
    1. Kreitlow S, Mundt S, Lindequist U. J. Biotechnol. 1999;70:61–63. - PubMed
    1. Muller D, Krick A, Kehraus S, Mehner C, Hart M, Kupper FC, Saxena K, Prinz H, Schwalbe H, Janning P, Waldmann H, Konig GM. J. Med. Chem. 2006;49:4871–4878. - PubMed
    1. Luesch H, Pangilinan R, Yoshida WY, Moore RE, Paul VJ. J. Nat. Prod. 2001;64:304–307. - PubMed
    1. Singh S, Kate BN, Banerjee UC. Crit. Rev. Biotechnol. 2005;25:73–95. - PubMed

Publication types

MeSH terms