Isolation, structure elucidation and biological activity of metabolites from Sch-642305-producing endophytic fungus Phomopsis sp CMU-LMA

被引：27

作者：

Adelin, Emilie ^{[1
]}

Servy, Claudine ^{[1
]}

Cortial, Sylvie ^{[1
]}

Levaique, Helene ^{[1
]}

Martin, Marie-Therese ^{[1
]}

Retailleau, Pascal ^{[1
]}

Le Goff, Geraldine ^{[1
]}

Bussaban, Boonsom ^{[2
]}

Lumyong, Saisamorn ^{[2
]}

Ouazzani, Jamal ^{[1
]}

机构：

[1] Ctr Natl Rech Sci, Ctr Rech Gif, ICSN, F-91198 Gif Sur Yvette, France

[2] Chiang Mai Univ, Dept Biol, Fac Sci, Chiang Mai 50200, Thailand

来源：

PHYTOCHEMISTRY | 2011年 / 72卷 / 18期

关键词：

Secondary metabolites; Phomopsis; Polyketides; Antimicrobial; Anticancer; BACTERIAL-DNA PRIMASE; HYDROXYTETRADECATRIENOIC ACID; STEREOSELECTIVE-SYNTHESIS; MYCOSPHAERELLA-RUBELLA; CONCISE SYNTHESIS; (+)-SCH 642305; INHIBITOR; METHODOLOGY; LACTONE;

D O I：

10.1016/j.phytochem.2011.08.010

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Eight polyketide compounds were isolated from the cultivation broth of Phomopsis sp. CMU-LMA. We have recently described LMA-P1, a bicyclic 10-membered macrolide, obtained as a bioconversion derivative of Sch-642305, the major compound isolated in this study. Benquinol is the ethyl ester derivative of the 13-dihydroxytetradeca-2,4,8-trienoic acid produced by Valsa ambiens. This compound is concomitantly produced with the 6,13-dihydroxytetradeca-2,4,8-trienoic acid (DHTTA) previously isolated from Mycosphaerella rubella. The absolute configuration of the new compound, (2R,3R,45,5R)-3-hydroxy-2, 4-dimethyl-5-[(S,Z)-3-methylpentenyl]-tetrahydro-pyranone LMA-P2 was confirmed by X-ray crystallography. The delta-lactone 2,3-dihydroxytetradecan-5-olide (DHTO) was previously isolated from Seiridium unicorne. This compound may form through the cyclization of the methyl-2,3,5-trihydroxytridecanoate LMA-P3, a new linear polyketide isolated in this study. Benquoine, a new 14-membered lactone generated from the cyclization of benquinol, is proposed as the key precursor for the biosynthesis of Sch-642305. Antimicrobial activity and cancer cell viability inhibition by the new compounds were investigated. Benquoine exhibits antimicrobial activity against Gram positive bacteria, and cytotoxicity against HCT-116 cancer cell line. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2406 / 2412

页数：7

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