Sesquiterpenes from the sponge Axinyssa isabela.
Further research on the constituents of the sponge Axinyssa isabela collected in the Gulf of California has led to the isolation of nine new sesquiterpenes, the eudesmanes axinisothiocyanates M and N (1, 2), the bisabolane axinythiocyanate A (3), and the aristolane derivatives axinysones A-E (4-8) and axinynitrile A (9), together with four known sesquiterpenoids (10-13). The structures of the new metabolites have been established by spectroscopic techniques.The absolute configuration of axinysones A (4) and B (5) has been assigned after esterification with (R)- and (S)-MPA acids. In addition, the unusual nitrile-containing sesquiterpene 9 has been synthesized from (+)-aristolone (14). The cytotoxic activity of the compounds isolated has been tested against three human tumor cell lines.
Zubía
Eva
E
Departamento de Química Orgánica, Facultad de Ciencias del Mar y Ambientales, Universidad de Cádiz, Apartado 40, 11510-Puerto Real (Cádiz), Spain. eva.zubia@uca.es
Ortega
María J
MJ
Carballo
J Luis
JL
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002140:California; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D017879:Isothiocyanates / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D009792:Oceans and Seas; D011161:Porifera / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D000970:Antineoplastic Agents; D017879:Isothiocyanates; D012717:Sesquiterpenes; C037152:isothiocyanic acid