Dichapetalins from Dichapetalum species and their cytotoxic properties

• Published in: Phytochemistry (Oxford) Vol. 94; pp. 184 - 191
• Main Authors: Long, Christophe, Aussagues, Yannick, Molinier, Nicolas, Marcourt, Laurence, Vendier, Laure, Samson, Arnaud, Poughon, Valérie, Chalo Mutiso, Patrick B., Ausseil, Frédéric, Sautel, François, Arimondo, Paola B., Massiot, Georges
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.10.2013; Elsevier
• Subjects: Antineoplastic Agents, Phytogenic - chemistry; Antineoplastic Agents, Phytogenic - isolation & purification; Antineoplastic Agents, Phytogenic - pharmacology; Biochemistry & Molecular Biology; Cell Line, Tumor; Cell Survival - drug effects; Chemical Sciences; Coordination chemistry; Crystallography, X-Ray; Cytotoxicity; Dammarane; Dichapetalaceae; Dichapetalum; Dichapetalum eickii; Dichapetalum leucosia; Dichapetalum mombuttense; Dichapetalum ruhlandii; Dichapetalum zenkeri; Dose-Response Relationship, Drug; HCT116 Cells; Heterocyclic Compounds, 4 or More Rings - chemistry; Heterocyclic Compounds, 4 or More Rings - pharmacology; HL-60 Cells; Humans; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy - methods; Magnoliopsida - chemistry; Magnoliopsida - classification; mass spectrometry; Molecular Structure; nuclear magnetic resonance spectroscopy; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Plant Roots - chemistry; Plant Sciences; Science & Technology; skeleton; Species Specificity; Spiro Compounds - chemistry; Spiro Compounds - pharmacology; Structure-Activity Relationship; ODSGGSFTIXWGOT-ILCGMRMXSA-N; Dichapetalaceae; WUKNHKDYWDDNMW-VTTQRWLYSA-N; Dichapetalum leucosia; ZUKJRORKNJQHBC-LRVWOOFFSA-N; Dichapetalum eickii; Dammarane; Cytotoxicity; AFPMYCKJJGHSPC-ZTVUMPOSSA-N; Dichapetalum mombuttense; Dichapetalum zenkeri; Dichapetalum ruhlandii; CONSTITUENTS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2013.03.023

Six dichapetalins named dichapetalins N–S were isolated from Dichapetalum mombuttense, D. zenkeri and D. leucosia. •Six new dichapetalins (N, O, P, Q, R and S) isolated from Dichapetalum mombuttense, D. zenkeri and D. leucosia.•Hemiketals isolated for the first time in D. zenkeri and D. leucosia.•First natural dichapetalins without the cyclopropane ring.•Dichapetalin P more potent than dichapetalin A on HCT-116 and WM 266-4 cell lines.•Corrected sign of optical rotatory power of dichapetalin A. 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 10–8M range.