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Chemistry of the Nudibranch Aldisa andersoni: Structure and Biological Activity of Phorbazole Metabolites
CNR, Instituto di Chimica Biomolecolare, Via Campi Flegrei 34, I-80078 Pozzuoli, Naples, Italy
Laboratoire de Toxicologie, Faculté de Pharmacie, Université Libre de Bruxelles (ULB), Campus de la Plaine, Boulevard du Triomphe, 1050, Brussels, Belgium
Service de Neurochirurgie, Hôpital Erasme, ULB, Route de Lennik, 1070 Brussels, Belgium
CSIR—National Institute of Oceanography, 403 004 Dona Paula, Goa, India
* Author to whom correspondence should be addressed.
Received: 25 June 2012; in revised form: 18 July 2012 / Accepted: 8 August 2012 / Published: 20 August 2012
Abstract: 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.
Keywords: Aldisa andersoni; nudibranch mollusc; structural elucidation; feeding-deterrence; growth inhibitory assays
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Nuzzo, G.; Ciavatta, M.L.; Kiss, R.; Mathieu, V.; Leclercqz, H.; Manzo, E.; Villani, G.; Mollo, E.; Lefranc, F.; D’Souza, L.; Gavagnin, M.; Cimino, G. Chemistry of the Nudibranch Aldisa andersoni: Structure and Biological Activity of Phorbazole Metabolites. Mar. Drugs 2012, 10, 1799-1811.
Nuzzo G, Ciavatta ML, Kiss R, Mathieu V, Leclercqz H, Manzo E, Villani G, Mollo E, Lefranc F, D’Souza L, Gavagnin M, Cimino G. Chemistry of the Nudibranch Aldisa andersoni: Structure and Biological Activity of Phorbazole Metabolites. Marine Drugs. 2012; 10(8):1799-1811.
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. 2012. "Chemistry of the Nudibranch Aldisa andersoni: Structure and Biological Activity of Phorbazole Metabolites." Mar. Drugs 10, no. 8: 1799-1811.