A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships

Vokatsoa C Rakotondramasy; Christine Mouriès; Xavier Cachet; Abdelhak Neghra; Missam El Mourabet; François Tillequin; Michel Koch; Brigitte Deguin

doi:10.1016/j.ejmech.2010.02.007

A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships

Eur J Med Chem. 2010 Jun;45(6):2314-20. doi: 10.1016/j.ejmech.2010.02.007. Epub 2010 Feb 16.

Authors

Vokatsoa C Rakotondramasy¹, Christine Mouriès, Xavier Cachet, Abdelhak Neghra, Missam El Mourabet, François Tillequin, Michel Koch, Brigitte Deguin

Affiliation

¹ Laboratoire de Pharmacognosie de l'Université Paris Descartes, U.M.R./C.N.R.S. n degrees 8638, Faculté des Sciences Pharmaceutiques et Biologiques, 4, Avenue de l'Observatoire, F-75006 Paris, France.

PMID: 20227146
DOI: 10.1016/j.ejmech.2010.02.007

Abstract

Five new unsaturated iridolactones 3-7 related to natural cytotoxic oxylipins, Tei 9826, and iridolactone 2, were prepared by parallel synthesis from natural aucubin. It was found that perpivaloyl iridoid glucosides 2, 3, and 4 were markedly cytotoxic against both L1210 and KB-3-1 cell lines.

MeSH terms

Animals
Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry*
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cyclopentanes / chemistry
Drug Design*
Glucosides / chemical synthesis
Glucosides / chemistry*
Glucosides / pharmacology*
Humans
Inhibitory Concentration 50
Iridoid Glucosides
Iridoids / chemical synthesis
Iridoids / chemistry*
Iridoids / pharmacology*
Mice
Structure-Activity Relationship

Substances

Antineoplastic Agents
Cyclopentanes
Glucosides
Iridoid Glucosides
Iridoids
aucubin
cyclopentenone