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|Title:||Condensation Of Macrocyclic Polyketides Produced By Penicillium Sp. Drf2 With Mercaptopyruvate Represents A New Fungal Detoxification Pathway|
|Author:||De Castro M.V.|
De Jesus K.
Pereira Filho E.R.
|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|
|Citation:||Journal Of Natural Products. American Chemical Society, v. 79, n. 6, p. 1668 - 1678, 2016.|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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