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DOI | 10.1021/acs.jnatprod.6b00295 |
Condensation of Macrocyclic Polyketides Produced by Penicillium sp DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway | |
de Castro, Marcos V.1; Ioca, Laura P.1; Williams, David E.2,3; Costa, Bruna Z.4; Mizuno, Carolina M.1,5,9; Santos, Mario F. C.1; de Jesus, Karen1; Ferreira, Everton L. F.1; Seleghim, Mirna H. R.5; Sette, Lara D.6; Pereira Filho, Edenir R.7; Ferreira, Antonio G.7; Goncalves, Natalia S.8; Santos, Raquel A.8; Patrick, Brian O.2; Andersen, Raymond J.2,3; Berlinck, Roberto G. S.1 | |
通讯作者 | Berlinck, Roberto G. S. |
来源期刊 | JOURNAL OF NATURAL PRODUCTS |
ISSN | 0163-3864 |
EISSN | 1520-6025 |
出版年 | 2016 |
卷号 | 79期号:6页码:1668-1678 |
英文摘要 | 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. |
类型 | Article |
语种 | 英语 |
国家 | Brazil ; Canada ; France |
收录类别 | SCI-E |
WOS记录号 | WOS:000378758200023 |
WOS关键词 | CURVULARIN-TYPE METABOLITES ; CITREO-VIRIDE-B ; SECONDARY METABOLITES ; ALTERNARIA-CINERARIAE ; ASPERGILLUS-NIDULANS ; DEGRADATION PRODUCT ; SONORAN DESERT ; IFO 6200 ; DEHYDROCURVULARIN ; BIOSYNTHESIS |
WOS类目 | Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy |
WOS研究方向 | Plant Sciences ; Pharmacology & Pharmacy |
资源类型 | 期刊论文 |
条目标识符 | http://119.78.100.177/qdio/handle/2XILL650/194649 |
作者单位 | 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.Univ Estadual Paulista, Inst Biociencias, Dept Bioquim & Microbiol, Campus Rio Claro,Ave 24-A, BR-1515 Rio Claro, SP, Brazil; 7.Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP, Brazil; 8.Univ Franca, Lab Genet & Biol Mol, Ave Dr Armando Salles Oliveira,201 Pq Univ, Franca, SP, Brazil; 9.Inst Pasteur, Dept Microbiol, Unit Mol Biol Gene Extremophiles, F-75015 Paris, France |
推荐引用方式 GB/T 7714 | de Castro, Marcos V.,Ioca, Laura P.,Williams, David E.,et al. Condensation of Macrocyclic Polyketides Produced by Penicillium sp DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway[J],2016,79(6):1668-1678. |
APA | de Castro, Marcos V..,Ioca, Laura P..,Williams, David E..,Costa, Bruna Z..,Mizuno, Carolina M..,...&Berlinck, Roberto G. S..(2016).Condensation of Macrocyclic Polyketides Produced by Penicillium sp DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway.JOURNAL OF NATURAL PRODUCTS,79(6),1668-1678. |
MLA | de Castro, Marcos V.,et al."Condensation of Macrocyclic Polyketides Produced by Penicillium sp DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway".JOURNAL OF NATURAL PRODUCTS 79.6(2016):1668-1678. |
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