Chemistry of the nudibranch Aldisa andersoni: structure and biological activity of phorbazole metabolites

• Published in: Marine drugs Vol. 10; no. 8; pp. 1799 - 1811
• Main Authors: Nuzzo, Genoveffa, Ciavatta, Maria Letizia, Kiss, Robert, Mathieu, Véronique, Leclercqz, Helene, Manzo, Emiliano, Villani, Guido, Mollo, Ernesto, Lefranc, Florence, D'Souza, Lisette, Gavagnin, Margherita, Cimino, Guido
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 20.08.2012; MDPI
• Subjects: Animals; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Cell Line, Tumor; Gastropoda - chemistry; Humans; Indian Ocean; Magnetic Resonance Spectroscopy; Mass Spectrometry; Oxazoles - chemistry; Oxazoles - isolation & purification; Oxazoles - pharmacology; Structure-Activity Relationship; Indian Ocean; structural elucidation; feeding-deterrence; Aldisa andersoni; growth inhibitory assays; nudibranch mollusc
• ISSN: 1660-3397; 1660-3397
• DOI: 10.3390/md10081799

The first chemical study of the Indo-Pacific dorid nudibranch Aldisa andersoni resulted in the isolation of five chlorinated phenyl-pyrrolyloxazoles belonging to the phorbazole series. Two new molecules, 9-chloro-phorbazole D and N1-methyl-phorbazole A, co-occurring with known phorbazoles A, B and D, have been characterized. Phorbazoles were found to be present mainly in the external part of the mollusc. The structures of the new compounds were determined by interpretation of spectroscopic data, mainly NMR and mass spectrometry and by comparison with the literature data. Evaluation of feeding-deterrence activity as well as in vitro growth inhibitory properties in human cancer cells was also carried out.