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

From National Research Council Canada

DOI	Resolve DOI: https://doi.org/10.1038/ja.2006.24
Author	Search for: Banskota, Arjun H.; Search for: McAlpine, James B.; Search for: Sørensen, Dan; Search for: Aouidate, Mustapha; Search for: Piraee, Mahmood; Search for: Alarco, Anne-Marie; Search for: Omura, Satoshi; Search for: Shiomi, Kazuro; Search for: Farnet, Chris M.; Search for: Zazopoulos, Emmanuel
Format	Text, Article
Subject	Streptomyces aculeolatus; Streptomyces sp.; E-837; E-492; E-975; Baeyer-Villiger monooxygenase
Abstract	Analyses 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.
Publication date	2006-03-01
Language	English
Peer reviewed	Yes
NRC publication	This is a non-NRC publication "Non-NRC publications" are publications authored by NRC employees prior to their employment by NRC.
NPARC number	21274266
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Record identifier	d3a12ca0-b14c-4f6f-9cf5-13f7c866cb35
Record created	2015-03-06
Record modified	2020-04-22

Date modified:: 2024-07-17