title: Dichapetalins from Dichapetalum species and their cytotoxic properties.
abstract: Six dichapetalins named dichapetalins N-S were isolated from Dichapetalum mombuttense, Dichapetalum zenkeri and Dichapetalum leucosia. They were accompanied in the same plants by the known dichapetalins A, B, C, I, L and M. The structures of the compounds were elucidated by 1D and 2D NMR experiments and mass spectrometry. They all possessed the dammarane skeleton substituted at position C-3 by a C6-C2 unit forming a 2-phenylpyran moiety. All contained a lactone ring in the side chain except dichapetalins O, Q and R, in which this ring was replaced by a lactol. Dichapetalin Q and R were also the first dichapetalins bearing a tertiary methyl and a double bond instead of the cyclopropane of the dammaranes. All these compounds were assayed against cancer cell lines HCT116 and WM 266-4 and displayed cytotoxic and anti-proliferative activities in the 10(-6) to 10(-8)M range.
authors.affiliation: USR CNRS-Pierre Fabre No. 3388 ETaC, Centre de Recherche et Développement Pierre Fabre, 3 avenue Hubert Curien, 31035 Toulouse Cedex 01, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Long
authors.forename: Yannick
authors.initials: Y
authors.lastname: Aussagues
authors.forename: Nicolas
authors.initials: N
authors.lastname: Molinier
authors.forename: Laurence
authors.initials: L
authors.lastname: Marcourt
authors.forename: Laure
authors.initials: L
authors.lastname: Vendier
authors.forename: Arnaud
authors.initials: A
authors.lastname: Samson
authors.forename: Valérie
authors.initials: V
authors.lastname: Poughon
authors.forename: Patrick B
authors.initials: PB
authors.lastname: Chalo Mutiso
authors.forename: Frédéric
authors.initials: F
authors.lastname: Ausseil
authors.forename: François
authors.initials: F
authors.lastname: Sautel
authors.forename: Paola B
authors.initials: PB
authors.lastname: Arimondo
authors.forename: Georges
authors.initials: G
authors.lastname: Massiot
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D018360:Crystallography, X-Ray; D004305:Dose-Response Relationship, Drug; D045325:HCT116 Cells; D018922:HL-60 Cells; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D019684:Magnoliopsida / Q000737:chemistry* / Q000145:classification; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry*; D013045:Species Specificity; D013141:Spiro Compounds / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D006576:Heterocyclic Compounds, 4 or More Rings; D010936:Plant Extracts; D013141:Spiro Compounds; C587556:dichapetalin A; C587554:dichapetalin N; C587555:dichapetalin P
keywords: AFPMYCKJJGHSPC-ZTVUMPOSSA-N; Cytotoxicity; Dammarane; Dichapetalaceae; Dichapetalum eickii; Dichapetalum leucosia; Dichapetalum mombuttense; Dichapetalum ruhlandii; Dichapetalum zenkeri; ODSGGSFTIXWGOT-ILCGMRMXSA-N; WUKNHKDYWDDNMW-VTTQRWLYSA-N; ZUKJRORKNJQHBC-LRVWOOFFSA-N