Cytotoxic sesquiterpenes from Aplysia dactylomela.
Three new chamigrenes, compound 1, acetyldeschloroelatol 2 (2-bromo-1,1,9-trimethyl-5-methylenespiro[5.5]undec-8-en-3-yl acetate), and acetylelatol 4 (2-bromo-8-chloro-1,1,9-trimethyl-5-methylenespiro[5.5]undec-8-en-3-yl acetate), and the known metabolites deschloroelatol 3, elatol 5, 8-acetylcaespitol 6, and caespitol 7 have been isolated from the sea hare Aplysia dactylomela. The structures of 1, 2, and 4 were determined on the basis of spectroscopic evidences. The in vitro cytotoxicity of six of these compounds against two cancer cell lines (HeLa and Hep-2) and nontumoral Vero cells was evaluated. The results support the hypothesis that the acetate derivatives decrease the toxicity of the corresponding alcohols in a strategy to store toxic metabolites acquired through the diet.
Dias
Teresa
T
Instituto de Productos Naturales y Agrobiología del CSIC, Avenida Astrofísico F. Sánchez, 3, Apartado 195, 38206 La Laguna, Spain.
Brito
Inmaculada
I
Moujir
Laila
L
Paiz
Nuria
N
Darias
José
J
Cueto
Mercedes
M
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001048:Aplysia / Q000737:chemistry*; D004032:Diet; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013030:Spain; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
C506504:2-bromo-1,1,9-trimethyl-5-methylenespiro(5.5)undec-8-en-3-yl acetate; D000970:Antineoplastic Agents; D012717:Sesquiterpenes; C506503:acetyldeschloroelatol; C506505:deschloroelatol