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Isolation and Structural Elucidation of Crellastatins B–H: Cytotoxic Bis(steroid) Derivatives from the Vanuatu Marine Sponge Crella sp.
Author(s) -
Zampella Angela,
Giannini Clelia,
Debitus Cécile,
Roussakis Christos,
V. D'Auria Maria
Publication year - 1999
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(199904)1999:4<949::aid-ejoc949>3.0.co;2-s
Subject(s) - chemistry , sponge , stereochemistry , steroid , hydroxylation , cytotoxic t cell , in vitro , carcinoma cell , cell culture , monomer , cytotoxicity , two dimensional nuclear magnetic resonance spectroscopy , enzyme , biochemistry , organic chemistry , botany , genetics , hormone , biology , polymer
Seven new cytotoxic dimeric steroids, namely crellastatins B–H ( 2 – 8 ), have been isolated from the Vanuatu sponge Crella sp. They have been structurally characterized on the basis of 2D‐NMR (500 MHz) and FAB‐MS data. All the new compounds show the same unprecedented junction between the monomeric units, formed via their side‐chains, whereas they differ from A ( 1 ) in the hydroxylation pattern of the two tetracyclic cores. Like crellastatin A ( 1 ), crellastatins B–H ( 2 – 8 ) exhibit in vitro antitumor activity against human bronchopulmonary non‐small‐cell lung carcinoma cell lines (NSCLC) with IC 50 values in the range of 2–10 μg/mL.