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

  • J Nat Prod. 2017 May 26;80(5):1339-1346. doi: 10.1021/acs.jnatprod.6b00941.
Marianna Carbone  1 ,  M Letizia Ciavatta  1 ,  Véronique Mathieu  2 ,  Aude Ingels  2 ,  Robert Kiss  2 ,  Paola Pascale  1 ,  Ernesto Mollo  1 ,  Nicon Ungur  3 ,  Yue-Wei Guo  4 ,  Margherita Gavagnin  1
Affiliations
  • 1. Consiglio Nazionale delle Ricerche (CNR), Istituto di Chimica Biomolecolare (ICB) , Via Campi Flegrei, 34, 80078 Pozzuoli (Na), Italy.
  • 2. Laboratoire de Cancérologie et de Toxicologie Expérimentale, Faculté de Pharmacie, Université Libre de Bruxelles (ULB) , Campus de la Plaine, Boulevard du Triomphe, 1050 Brussels, Belgium.
  • 3. Institute of Chemistry, Moldova Academy of Sciences , Academiei str. 3, MD-2028 Chisinau, Republic of Moldova.
  • 4. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences , Shanghai 201203, P.R. China.
PMID: 28406636 DOI: 10.1021/acs.jnatprod.6b00941
Abstract

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.