Marine Terpenoid Diacylguanidines: Structure, Synthesis, and Biological Evaluation of Naturally Occurring Actinofide and Synthetic Analogues

A new diacylguanidine, actinofide (1), has been isolated from the marine mollusk Actinocyclus papillatus. The structure, exhibiting a guanidine moiety acylated by two terpenoid acid units, has been established by spectroscopic methods and secured by synthesis. Following this, a series of structural...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2017-05, Vol.80 (5), p.1339-1346
Main Authors: Carbone, Marianna, Ciavatta, M. Letizia, Mathieu, Véronique, Ingels, Aude, Kiss, Robert, Pascale, Paola, Mollo, Ernesto, Ungur, Nicon, Guo, Yue-Wei, Gavagnin, Margherita
Format: Article
Language:English
Subjects:
Animals
Cell Line, Tumor
Drug Screening Assays, Antitumor
Guanidine - chemistry
Humans
Molecular Structure
Mollusca - chemistry
Structure-Activity Relationship
Terpenes - chemical synthesis
Terpenes - chemistry
Terpenes - isolation & purification
Terpenes - pharmacology
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Summary:A new diacylguanidine, actinofide (1), has been isolated from the marine mollusk Actinocyclus papillatus. The structure, exhibiting a guanidine moiety acylated by two terpenoid acid units, has been established by spectroscopic methods and secured by synthesis. Following this, a series of structural analogues have been synthesized using the same procedure. All of the compounds have been evaluated in vitro for the growth inhibitory activity against a variety of cancer cell lines.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00941