Long-Chain Acyl-Homoserine Lactones from Methylobacterium mesophilicum: Synthesis and Absolute Configuration
Long-Chain Acyl-Homoserine Lactones from Methylobacterium mesophilicum: Synthesis and Absolute Configuration
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DOI：
10.1021/np900043j
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发表时间：
2009-12-01
影响因子：
5.1
通讯作者：
Marsaioli, Anita J.
中科院分区：
文献类型：
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作者：
Pomini, Armando M.;Cruz, Pedro L. R.;Marsaioli, Anita J.
研究人员对从感染柑橘杂色失绿症 (CVC) 病的橙树中分离的嗜温甲基杆菌产生的酰基高丝氨酸内酯 (酰基-HSL) 进行了研究，揭示了六种长链酰基-HSL 的存在，即饱和同系物 (S)-N-十二烷酰基 (1) 和 (S)-N-十四烷酰基-HSL (5)，罕见的奇数链 N-十三烷酰基-HSL (3)、新的天然产物 (S)-N-(2E)-十二烯酰基-HSL (2) 以及罕见的不饱和同系物 (S)-N-(7Z)-十四烯酰基 (4) 和 (S)-N-(2E,7Z)-十四碳烯酰基-HSL (6)。所有HSL的绝对构型被确定为3S。化合物2和6为首次合成。使用合成酰基-HSL 对与 CVC 感染树中的嗜温分枝杆菌共分离的革兰氏阳性细菌内生菌进行抗菌测定，结果显示抗菌活性较低或无抗菌活性。
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.