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From Inactive Nortopsentin D, a Novel Bis(indole) Alkaloid Isolated from the Axinellid Sponge Dragmacidon sp. from Deep Waters South of New Caledonia, to a Strongly Cytotoxic Derivative
Author(s) -
Mancini Ines,
Guella Graziano,
Pietra Francesco,
Debitus Cécile,
Waikedre Jean
Publication year - 1996
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19960790804
Subject(s) - chemistry , stereochemistry , indole test , derivative (finance) , alkaloid , cytotoxic t cell , sponge , appendage , biochemistry , in vitro , botany , medicine , anatomy , financial economics , economics , biology
Nortopsentin D ( 5 ), a bis(indole) alkaloid unique for bearing a 2‐amino‐methylimidazole appendage at the central 1 H ‐imidazol‐5(4 H )‐one nucleus, was isolated in abundance, besides the putative biogenetic precursor 6 of its appendage, from the deep‐water axinellid sponge Dragmacidon sp. Structural elucidation of 5 by NMR and MS methods heavily relied on its N ‐methyl derivatives 8–11 . Unusually for topsentin‐type structures, natural 5 and semisynthetic methyl derivatives 8 and 10 proved inactive on KB tumoural cells, while introduction of the last three methyl groups, amazingly led to highly cytotoxic 11 .