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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Pomini, Armando M. [1] ; Cruz, Pedro L. R. [1] ; Gai, Claudia [2] ; Araujo, Welington L. [2] ; Marsaioli, Anita J. [1]
Total Authors: 5
Affiliation:
[1] Univ Estadual Campinas, Inst Chem, BR-13083970 Campinas, SP - Brazil
[2] Univ Sao Paulo, ESALQ, Dept Genet, BR-13400970 Piracicaba, SP - Brazil
Total Affiliations: 2
Document type: Journal article
Source: Journal of Natural Products; v. 72, n. 12, p. 2125-2129, DEC 2009.
Web of Science Citations: 23
Abstract

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. (AU)

FAPESP's process: 05/02934-4 - Chemical study of signaling substances produced by higher bacteria and eukaryotes
Grantee:Armando Mateus Pomini
Support Opportunities: Scholarships in Brazil - Doctorate