Clavaminols A-F, novel cytotoxic 2-amino-3-alkanols from the ascidian Clavelina phlegraea.
The chemical investigation of the Mediterranean ascidian Clavelina phlegraea has led to the isolation of six new 2-amino-3-alkanol derivatives, clavaminols A-F (1-6). Their stereostructures were established by analysis of spectroscopic data and chemical conversion. Clavaminols A, B, C, and F were tested for their cytotoxic and pro-apoptotic properties and clavaminol A was shown to be the more potent cytotoxic compound of this series inducing cell death through activation of the apoptotic machinery.
Aiello
Anna
A
Dipartimento di Chimica delle Sostanze Naturali, Università degli Studi di Napoli Federico II, Via D. Montesano 49, 80131 Napoli, Italy.
Fattorusso
Ernesto
E
Giordano
Antonella
A
Menna
Marialuisa
M
Navarrete
Carmen
C
Muñoz
Eduardo
E
D000605:Amino Alcohols / Q000302:isolation & purification* / Q000494:pharmacology*; D000818:Animals; D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004249:DNA Damage / Q000187:drug effects; D005452:Fluoresceins / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D014561:Urochordata / Q000737:chemistry*
D000605:Amino Alcohols; D000970:Antineoplastic Agents; D005452:Fluoresceins; C007740:fluorexon