Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/319507
Type: Artigo de periódico
Title: Condensation Of Macrocyclic Polyketides Produced By Penicillium Sp. Drf2 With Mercaptopyruvate Represents A New Fungal Detoxification Pathway
Abstract: Application of a refined procedure of experimental design and chemometric analysis to improve the production of curvularin-related polyketides by a marine-derived Penicillium sp. DRF2 resulted in the isolation and identification of cyclothiocurvularins 6-8 and cyclosulfoxicurvularins 10 and 11, novel curvularins condensed with a mercaptolactate residue. Two additional new curvularins, 3 and 4, are also reported. The structures of the sulfur-bearing curvularins were unambiguously established by analysis of spectroscopic data and by X-ray diffraction analysis. Analysis of stable isotope feeding experiments with [U-13C3 15N]-l-cysteine confirmed the presence of the 2-hydroxy-3-mercaptopropanoic acid residue in 6-8 and the oxidized sulfoxide in 10 and 11. Cyclothiocurvularins A (6) and B (7) are formed by spontaneous reaction between 10,11-dehydrocurvularin (2) and mercaptopyruvate (12) obtained by transamination of cysteine. High ratios of [U-13C3 15N]-l-cysteine incorporation into cyclothiocurvularin B (7), the isolation of two diastereomers of cyclothiocurvularins, the lack of cytotoxicity of cyclothiocurvularin B (7) and its methyl ester (8), and the spontaneous formation of cyclothiocurvularins from 10,11-dehydrocurvularin and mercaptopyruvate provide evidence that the formation of cyclothiocurvularins may well correspond to a 10,11-dehydrocurvularin detoxification process by Penicillium sp. DRF2. © 2016 The American Chemical Society and American Society of Pharmacognosy.
Editor: American Chemical Society
Rights: fechado
Identifier DOI: 10.1021/acs.jnatprod.6b00295
Address: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84976416033&partnerID=40&md5=05775612caf66f3439dd50d1b63787a4
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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