| Full text | |
| Author(s): Show less - |
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 |