Isolation and identification of three new 5-Alkenyl-3,3(2H)-furanones from two Streptomyces species using a genomic screening approach

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DOIResolve DOI: http://doi.org/10.1038/ja.2006.24
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TypeArticle
ISSN0021-8820
1881-1469
Volume59
Issue3
Pages168176; # of pages: 9
SubjectStreptomyces aculeolatus; Streptomyces sp.; E-837; E-492; E-975; Baeyer-Villiger monooxygenase
AbstractAnalyses of biosynthetic gene clusters derived from Streptomyces aculeolatus NRRL 18422 and Streptomyces sp. Eco86 indicated that both microorganisms have similar type I polyketide synthase (PKS) gene clusters with relatively few genes encoding post-PKS elaborative enzymes. However both gene clusters included a sequence coding for a relatively uncommon oxidative enzyme related to Baeyer-Villiger, flavin-type monooxygenases. Screening of culture extracts for compounds with the predicted physicochemical properties of the end products from these loci, led to the isolation of three 5-alkenyl-3,3(2H)-furanones, one (E-837, 1) from the former and two (E-492, 2, E-975, 3) from the latter strain. The structures, confirmed by spectral analyses including MS, and 1D and 2D NMR experiments, were in accord with those predicted by genomic analyses. Baeyer-Villiger type oxidation is postulated to be involved in the formation of the furanone moieties in these molecules. All three new compounds were tested for their electron transport inhibitory activities. They had IC50 values of 1approx4 microg/ml against Ascaris suum NADH-fumarate reductase and 1approx12 microg/ml against bovine heart NADH oxidase.
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LanguageEnglish
Peer reviewedYes
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NPARC number21274266
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Record created2015-03-06
Record modified2016-05-09
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