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Isolation of Plakinamine I: A New Steroidal Alkaloid from the Marine Sponge Corticium sp. and Synthesis of an Analogue Model Compound
Author(s) -
Zampella Angela,
D'Orsi Rosa,
Sepe Valentina,
De Marino Simona,
Borbone Nicola,
Valentin Alexis,
Debitus Cécile,
Zollo Franco,
Valeria D'Auria Maria
Publication year - 2005
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/ejoc.200500364
Subject(s) - sponge , chemistry , alkaloid , stereochemistry , cytotoxicity , cytotoxic t cell , botany , biochemistry , in vitro , biology
A new cytotoxic steroidal alkaloid, plakinamine I, with an unprecedented 3α‐amino‐19‐acetoxy nucleus was isolated from a Corticium sp. sponge. The structure has been elucidated by spectroscopic analysis and secured by the synthesis of the model 19‐acetoxy‐3α‐aminocholestane. The evaluation of the cytotoxic activities of several synthetic derivatives, intermediates of the above synthesis, allowed us to explore the influence of the different functions on the cytotoxicity observed for natural plakinamine I. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)