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Insights into the Biosynthesis of Cyclic Guanidine Alkaloids from Crambeidae Marine Sponges
Author(s) -
Silva Siguara B. L.,
Oberhänsli François,
Tribalat MarieAude,
GentaJouve Grégory,
Teyssié JeanLouis,
DechraouiBottein MarieYasmine,
Gallard JeanFrançois,
Evanno Laurent,
Poupon Erwan,
Thomas Olivier P.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201809539
Subject(s) - guanidine , sponge , metabolic pathway , biomimetic synthesis , chemistry , crambe , biochemistry , biology , metabolism , botany
Among the outstanding chemical diversity found in marine sponges, cyclic guanidine alkaloids, present in species of the family Crambeidae, are particularly attractive, not only because of their unique chemical features, but also due to a broad range of biological activities. Despite a growing interest in these natural products as therapeutic agents, their metabolic pathway has not been experimentally investigated. Ex situ feeding experiments using radiolabeled precursors performed on the Mediterranean sponge Crambe crambe suggest arginine and fatty acids as precursors in the metabolic pathway of crambescins. A subsequent bio‐inspired approach supported the change of paradigm in the metabolic pathway of cyclic guanidine alkaloids. A large part of the chemical diversity of this family would therefore originate from a tethered Biginelli‐like reaction between C‐2/C‐3 activated fatty acids and a central guanidinylated pyrrolinium.