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Angew Chem Int Ed Engl. 2014 Oct 20;53(43):11583-6. doi: 10.1002/anie.201405990. Epub 2014 Sep 4.

Forazoline A: marine-derived polyketide with antifungal in vivo efficacy.

Author information

1
Pharmaceutical Sciences Division, University of Wisconsin-Madison, Madison, WI 53705 (USA).

Abstract

Forazoline A, a novel antifungal polyketide with in vivo efficacy against Candida albicans, was discovered using LCMS-based metabolomics to investigate marine-invertebrate-associated bacteria. Forazoline A had a highly unusual and unprecedented skeleton. Acquisition of (13)C-(13)C gCOSY and (13)C-(15)N HMQC NMR data provided the direct carbon-carbon and carbon-nitrogen connectivity, respectively. This approach represents the first example of determining direct (13)C-(15)N connectivity for a natural product. Using yeast chemical genomics, we propose that forazoline A operated through a new mechanism of action with a phenotypic outcome of disrupting membrane integrity.

KEYWORDS:

NMR spectroscopy; antifungal agents; genomics; natural products; structure elucidation

PMID:
25197007
PMCID:
PMC4215405
DOI:
10.1002/anie.201405990
[Indexed for MEDLINE]
Free PMC Article

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