期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 2, 页码 520-525出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201809539
关键词
biomimetic synthesis; biosynthesis; cyclic guanidine alkaloids; feeding experiments; marine sponges
资金
- Brazilian Foundation Capes [99999.010184/2013-09]
- French Ministry of Higher Education and Research
- CNRS initiative Projets Exploratoires Premier Soutien (PEPS ExoMod)
- Marine Institute [PBA/MB/16/01]
- Marine Research Programme of the Irish Government
- Government of the Principality of Monaco
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.
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