title: A Ring-D-Seco-Tetranortriterpenoid from Seeds of Carapa procera Active against Breast Cancer Cell Lines.
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.
authors.affiliation: Laboratoire de Chimie Organique et Thérapeutique, Faculté de Médecine, de Pharmacie et d'Odontologie, Université Cheikh Anta Diop de Dakar, Fann, Dakar, Sénégal.
authors.forename: Mbaye Diaw
authors.initials: MD
authors.lastname: Dioum
authors.affiliation: Laboratoire de Chimie Organique et Thérapeutique, Faculté de Médecine, de Pharmacie et d'Odontologie, Université Cheikh Anta Diop de Dakar, Fann, Dakar, Sénégal.
authors.forename: Matar
authors.initials: M
authors.lastname: Seck
authors.affiliation: EBSI team, CEISAM, University of Nantes - CNRS UMR 6230, Nantes, France.
authors.forename: Virginie
authors.initials: V
authors.lastname: Silvestre
authors.affiliation: IMF team, CEISAM, University of Nantes - CNRS UMR 6230, Nantes, France.
authors.forename: Aurélien
authors.initials: A
authors.lastname: Planchat
authors.affiliation: EBSI team, CEISAM, University of Nantes - CNRS UMR 6230, Nantes, France.
authors.forename: Denis
authors.initials: D
authors.lastname: Loquet
authors.affiliation: 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.
authors.forename: Steven
authors.initials: S
authors.lastname: Lohard
authors.affiliation: 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.
authors.forename: Sophie
authors.initials: S
authors.lastname: Barille-Nion
authors.affiliation: EBSI team, CEISAM, University of Nantes - CNRS UMR 6230, Nantes, France.
authors.forename: Gerald S
authors.initials: GS
authors.lastname: Remaud
authors.affiliation: EBSI team, CEISAM, University of Nantes - CNRS UMR 6230, Nantes, France.
authors.forename: Richard J
authors.initials: RJ
authors.lastname: Robins
authors.affiliation: EBSI team, CEISAM, University of Nantes - CNRS UMR 6230, Nantes, France.
authors.forename: Illa
authors.initials: I
authors.lastname: Tea
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001943:Breast Neoplasms; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C000614934:5,6-dehydro-7-deacetoxy-7-oxogedunin; D000972:Antineoplastic Agents, Phytogenic; D036701:Limonins; D010936:Plant Extracts; D014315:Triterpenes; C554989:mexicanolide