title: Antiparasitic compounds from Cupania cinerea with activities against Plasmodium falciparum and Trypanosoma brucei rhodesiense.
abstract: In a survey of plants from Ecuador with antiprotozoal activity, Cupania cinerea was found to show significant in vitro activity against the Plasmodium falciparum K1 strain and Trypanosoma brucei rhodesiense. Subsequently, activity-guided isolation of the n-hexane and dichloromethane extracts from the bark of C. cinerea afforded two diterpene glycosides (1 and 2), named cupacinoside and 6'-de-O-acetylcupacinoside, and a lactonized triterpene bearing an oxepin moiety named cupacinoxepin (3), together with the known compounds scopoletin (4), caryophyllene oxide (5), two bisabolane sesquiterpenes (6 and 7), lichexanthone (8), gustastatin (9), lupenone (10), betulone (11), 17β,21β-epoxyhopan-3-one (12), taraxerol (13), and taraxerone (14). For compound 3, X-ray crystallography was employed to elucidate the relative configuration. For cupacinosides (1) and (2) and cupacinoxepin (3), in vitro activities against the P. falciparum K1 strain (IC(50)1, 1.3; 2, 1.8; and 3, 8.7 μM) and T. b. rhodesiense (IC(50)1, 4.5; 2, 15.8; and 3, 71.6 μM) were found. Cytotoxicity toward L-6 cells is discussed for all the compounds isolated.
authors: Institute of Pharmaceutical Sciences, Department of Pharmacognosy, Karl-Franzens-University Graz, Universitätsplatz 4, 8010 Graz, Austria.
authors: M Salomé
authors: MS
authors: Gachet
authors: Olaf
authors: O
authors: Kunert
authors: Marcel
authors: M
authors: Kaiser
authors: Reto
authors: R
authors: Brun
authors: Martin
authors: M
authors: Zehl
authors: Walter
authors: W
authors: Keller
authors: Ricardo A
authors: RA
authors: Muñoz
authors: Rudolf
authors: R
authors: Bauer
authors: Wolfgang
authors: W
authors: Schuehly
mesh_terms: D000818:Animals; D000981:Antiprotozoal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D002478:Cells, Cultured; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D004484:Ecuador; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D006586:Hexanes; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects*; D000081223:Polycyclic Sesquiterpenes; D051381:Rats; D029631:Sapindaceae / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016833:Trypanosoma brucei rhodesiense / Q000187:drug effects*
chemical_list: C558966:6'-de-O-acetylcupacinoside; D000981:Antiprotozoal Agents; D004224:Diterpenes; D006027:Glycosides; D006586:Hexanes; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; D014315:Triterpenes; C558965:cupacinoside; C558967:cupacinoxepin; C026385:n-hexane; C515179:caryophyllene oxide