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

Par Conseil national de recherches du Canada

DOI	Trouver le DOI : https://doi.org/10.1038/ja.2006.24
Auteur	Rechercher : Banskota, Arjun H.; Rechercher : McAlpine, James B.; Rechercher : Sørensen, Dan; Rechercher : Aouidate, Mustapha; Rechercher : Piraee, Mahmood; Rechercher : Alarco, Anne-Marie; Rechercher : Omura, Satoshi; Rechercher : Shiomi, Kazuro; Rechercher : Farnet, Chris M.; Rechercher : Zazopoulos, Emmanuel
Format	Texte, Article
Sujet	Streptomyces aculeolatus; Streptomyces sp.; E-837; E-492; E-975; Baeyer-Villiger monooxygenase
Résumé	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.
Date de publication	2006-03-01
Langue	anglais
Publications évaluées par des pairs	Oui
Publication du CNRC	Cette publication n’est pas du CNRC Ce sont des publications qui ont été rédigées par un auteur du CNRC, mais avant que celui-ci soit employé du CNRC.
Numéro NPARC	21274266
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Identificateur de l’enregistrement	d3a12ca0-b14c-4f6f-9cf5-13f7c866cb35
Enregistrement créé	2015-03-06
Enregistrement modifié	2020-04-22

Date de modification :: 2024-07-17