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Antifungal Diterpene Alkaloids from the Caribbean Sponge Agelas citrina : Unified Configurational Assignments of Agelasidines and Agelasines
Author(s) -
Stout E. Paige,
Yu Lily C.,
Molinski Tadeusz F.
Publication year - 2012
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.201200572
Subject(s) - diterpene , chemistry , sponge , antifungal , stereochemistry , botany , microbiology and biotechnology , biology
Three new diterpene alkaloids – the hypotaurocyamines, (–)‐agelasidines E and F ( 5 , 6 ), and an adeninium salt, agelasine N ( 9 ) – were isolated from the Caribbean sponge Agelas citrina along with six known natural products: agelasines B–E ( 7 , 10 – 12 ), 2‐oxo‐agelasine B ( 8 ), and (–)‐agelasidine C ( 3 ). The chemical structures of 5 , 6 , and 9 were elucidated by NMR spectroscopy and mass spectrometry. This represents the first report of natural products from the sponge A. citrina . Unified assignment of the absolute configurations of the new compounds and known compounds was achieved by chemical correlation, quantitative measurements of molar rotations, and comparative analysis by van't Hoff's principle of optical superposition. (–)‐Agelasidine C ( 3 ) exhibited potent antifungal and modest cytotoxic activity against human chronic lymphocytic leukemia (CLL) cells.