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Axinellins A and B: New Proline‐Containing Antiproliferative Cyclopeptides from the Vanuatu Sponge Axinella carteri
Author(s) -
Randazzo Antonio,
Dal Piaz Fabrizio,
Orrù Stefania,
Debitus Cécile,
Roussakis Christos,
Pucci Piero,
GomezPaloma Luigi
Publication year - 1998
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199811)1998:11<2659::aid-ejoc2659>3.0.co;2-h
Subject(s) - chemistry , stereochemistry , amino acid , sponge , two dimensional nuclear magnetic resonance spectroscopy , tandem mass spectrometry , in vitro , mass spectrometry , biochemistry , botany , chromatography , biology
Two new bioactive cyclopeptides, named axinellins A ( 1 ) and B ( 2 ) have been isolated from the marine sponge Axinella carteri . Their structure elucidation was based on two‐dimensional (2D) NMR (500 MHz) as well as HRFABMS and ESMS/MS data. All amino acid residues derived from axinellins A and B were found to possess L configuration at Cα by HPLC analysis of their FDAA derivatives (Marfey's method). The amino acid sequence of 1 and 2 was established on the basis of tandem mass spectrometry data (ESMS/MS) and on 1 H‐ 1 H through‐space connectivities observed in NOESY and ROESY spectra. Axinellins A ( 1 ) and B ( 2 ) exhibited moderate in vitro antitumor activity against human broncopulmonary non‐small‐cell‐lung‐carcinoma lines (NSCLC‐N6) with IC 50 values of 3.0 and 7.3 μg/ml, respectively.