Planta Med 2016; 82(11/12): 967-972
DOI: 10.1055/s-0042-107797
Biological and Pharmacological Activity
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

A Ring-D-Seco-Tetranortriterpenoid from Seeds of Carapa procera Active against Breast Cancer Cell Lines

Mbaye Diaw Dioum
1  Laboratoire de Chimie Organique et Thérapeutique, Faculté de Médecine, de Pharmacie et dʼOdontologie, Université Cheikh Anta Diop de Dakar, Fann, Dakar, Sénégal
2  EBSI team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
,
Matar Seck
1  Laboratoire de Chimie Organique et Thérapeutique, Faculté de Médecine, de Pharmacie et dʼOdontologie, Université Cheikh Anta Diop de Dakar, Fann, Dakar, Sénégal
,
Virginie Silvestre
2  EBSI team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
,
Aurélien Planchat
3  IMF team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
,
Denis Loquet
2  EBSI team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
,
Steven Lohard
4  CRCNA, UMR INSERM U892/CNRS 6299/Team 8 “Cell survival and tumor escape in breast cancers”, Institut de Recherche en Santé, University of Nantes, Nantes, France
,
Sophie Barille-Nion
4  CRCNA, UMR INSERM U892/CNRS 6299/Team 8 “Cell survival and tumor escape in breast cancers”, Institut de Recherche en Santé, University of Nantes, Nantes, France
,
Gerald S Remaud
2  EBSI team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
,
Richard J Robins
2  EBSI team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
,
Illa Tea
2  EBSI team, CEISAM, University of Nantes – CNRS UMR 6230, Nantes, France
› Author Affiliations
Further Information

Publication History

received 21 December 2015
revised 18 April 2016

accepted 18 April 2016

Publication Date:
25 May 2016 (eFirst)

Abstract

The seeds of Carapa procera are exploited extensively in West African ethnopharmacy for the treatment of several pathologies, including inflammation. They also are effective as insect antifeedants and as a mosquito repellent. With the aim of identifying bioactive principles, an ethyl acetate extract of the defatted seeds was made and fractionated. Two principle compounds were isolated. One of these, 5,6-dehydro-7-deacetoxy-7-oxogedunin (1), while known from another genus of the Meliaceae, is newly identified from the genus Carapa and its X-ray structure is described for the first time. In addition, 1 displayed strong anti-clonogenic activity at 10 µM. The other compound, mexicanolide (2), is known from this species and showed neither cytotoxicity nor anti-clonogenicity. These differences in efficacy are discussed in relation to known structure-activity relationships of limonoids.

Supporting Information