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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Condensation of Macrocyclic Polyketides Produced by Penicillium sp DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway

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de Castro, Marcos V. [1] ; Ioca, Laura P. [1] ; Williams, David E. [2, 3] ; Costa, Bruna Z. [4] ; Mizuno, Carolina M. [1, 5, 6] ; Santos, Mario F. C. [1] ; de Jesus, Karen [1] ; Ferreira, Everton L. F. [1] ; Seleghim, Mirna H. R. [5] ; Sette, Lara D. [7] ; Pereira Filho, Edenir R. [8] ; Ferreira, Antonio G. [8] ; Goncalves, Natalia S. [9] ; Santos, Raquel A. [9] ; Patrick, Brian O. [2] ; Andersen, Raymond J. [2, 3] ; Berlinck, Roberto G. S. [1]
Total Authors: 17
Affiliation:
[1] Univ Sao Paulo, Inst Quim Sao Carlos, CP 780, BR-13560970 Sao Carlos, SP - Brazil
[2] Univ British Columbia, Dept Chem, Vancouver, BC V6T 1Z1 - Canada
[3] Univ British Columbia, Dept Earth Ocean & Atmospher Sci, Vancouver, BC V6T 1Z1 - Canada
[4] Univ Estadual Campinas, Inst Quim, Caixa Postal 6154, BR-13083970 Campinas, SP - Brazil
[5] Univ Fed Sao Carlos, Dept Ecol & Biol Evolut, Sao Carlos, SP - Brazil
[6] Inst Pasteur, Dept Microbiol, Unit Mol Biol Gene Extremophiles, F-75015 Paris - France
[7] Univ Estadual Paulista, Inst Biociencias, Dept Bioquim & Microbiol, Campus Rio Claro, Ave 24-A, BR-1515 Rio Claro, SP - Brazil
[8] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[9] Univ Franca, Lab Genet & Biol Mol, Ave Dr Armando Salles Oliveira, 201 Pq Univ, Franca, SP - Brazil
Total Affiliations: 9
Document type: Journal article
Source: Journal of Natural Products; v. 79, n. 6, p. 1668-1678, JUN 2016.
Web of Science Citations: 11
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-(C3N)-C-13-N-15]-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-(C3N)-C-13-N-15]-L-cysteine incorporation into cyclothiocurvularin B (7), the isolation of two diastereomers of cyclothiocurvularin, 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 cyclothiocurvularin may well correspond to a 10,11-dehydrocurvularin detoxification process by Penicillium sp. DRF2. (AU)

FAPESP's process: 05/60175-2 - Discovery and development of potential chemotherapeutic agents based on marine invertebrates and associated micro-organisms
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 10/50190-2 - Investigation of metabolic and biotechnological potential of marine organisms in bioremediation processes and for the production of substances with anti-viral, anti-inflammatory and anti-Leishmania activities (Marine Biodiversity)
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 12/50026-3 - International collaboration in the chemistry of alkaloid natural product biosynthesis
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: Regular Research Grants
FAPESP's process: 13/50228-8 - Biodiversity components, and their metabolic characters, of Brazilian Islands: an integrated approach
Grantee:Roberto Gomes de Souza Berlinck
Support Opportunities: BIOTA-FAPESP Program - Thematic Grants