Long-Chain Acyl-Homoserine Lactones from Methylobacterium mesophilicum: Synthesis and Absolute Configuration

被引：27

作者：

Pomini, Armando M. ^{[1
]}

Cruz, Pedro L. R. ^{[1
]}

Gai, Claudia ^{[2
]}

Araujo, Welington L. ^{[2
]}

Marsaioli, Anita J. ^{[1
]}

机构：

[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP, Brazil

[2] Univ Sao Paulo, ESALQ, Dept Genet, BR-13400970 Piracicaba, SP, Brazil

来源：

JOURNAL OF NATURAL PRODUCTS | 2009年 / 72卷 / 12期

基金：

巴西圣保罗研究基金会;

关键词：

DOUBLE-BOND POSITION; GRAM-NEGATIVE BACTERIA; QUORUM-SENSING SIGNALS; XYLELLA-FASTIDIOSA; MASS-SPECTROMETRY; ACYLHOMOSERINE LACTONES; EXTORQUENS AM1; CITRUS PLANTS; ANALOGS; CHROMATOGRAPHY;

D O I：

10.1021/np900043j

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

The acyl-homoserine lactones (acyl-HSLs) produced by Methylobacterium mesophilicum isolated from orange trees infected with the citrus variegated chlorosis (CVC) disease have been studied, revealing the occurrence of six long-chain acyl-HSLs, i.e., the saturated homologues (S)-N-dodecanoyl (1) and (S)-N-tetradecanoyl-HSL (5), the uncommon odd-chain N-tridecanoyl-HSL (3), the new natural product (S)-N-(2E)-dodecenoyl-HSL (2), and the rare unsaturated homologues (S)-N-(7Z)-tetradecenoyl (4) and (S)-N-(2E,7Z)-tetradecadienyl-HSL (6). The absolute configurations of all HSLs were determined as 3S. Compounds 2 and 6 were synthesized for the first time. Antimicrobial assays with synthetic acyl-HSLs against Gram-positive bacterial endophytes co-isolated with M. mesophilicum from CVC-infected trees revealed low or no antibacterial activity.

引用

页码：2125 / 2129

页数：5

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