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

Autor(es)

Pomini, Armando M. ^[1] ; Cruz, Pedro L. R. ^[1] ; Gai, Claudia ^[2] ; Araujo, Welington L. ^[2] ; Marsaioli, Anita J. ^[1]

Afiliação do(s) autor(es)

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

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

• Tipo de documento: Artigo Científico
• Fonte: Journal of Natural Products; v. 72, n. 12, p. 2125-2129, DEC 2009.
• Citações Web of Science: 23

Resumo

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)

• Processo FAPESP: 05/02934-4 - Estudo químico das substâncias sinalizadoras produzidas por bactérias e eucariotos superiores
• Beneficiário: Armando Mateus Pomini
• Modalidade de apoio: Bolsas no Brasil - Doutorado