Cupaniol, a New Branched Polyprenol, from Cupania latifolia

Antiparasitic Compounds from Cupania cinerea with Activities against Plasmodium falciparum and Trypanosoma bruceirhodesiense

“…8À16 Common constituents that have been identified in the genus Cupania include sterols, triterpenes, diterpene glycosides, and a polyprenol. 9,10,17 During a recent evaluation of antiprotozoal activity of plants traditionally used for medicine in Ecuador, the n-hexane and dichloromethane extracts of the bark of C. cinerea showed promising in vitro activity against Plasmodium falciparum K1 strain and Trypanosoma brucei rhodesiense. 19 To date, antiplasmodial and leishmanicidal activities have been reported from the n-hexane extract of the leaves of Cupania vernalis, which were attributed to the general cytotoxicity of the diterpene glycosides present in this plant.…”

“…19 To date, antiplasmodial and leishmanicidal activities have been reported from the n-hexane extract of the leaves of Cupania vernalis, which were attributed to the general cytotoxicity of the diterpene glycosides present in this plant. 14,15 The present article describes the bioassay-guided isolation, structure elucidation, antiprotozoal evaluation, and the assessment of cytotoxicity of three new compounds, namely, cupacinoside (1), 6 0 -de-O-acetylcupacinoside (2), and 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), Received: June 30, 2010 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 0 -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).…”

Rapid and quantitative determination of solanesol in Nicotiana tabacum by liquid chromatography–tandem mass spectrometry

“…The product ion spectrum obtained, which is shown in Fig. 4, consisted of an intense ion at m/z 69.2 and a second intense ion at m/z 81.1 when CE was 35 V. The two base ions at 69.2 and 81.1 were characteristic ions of polyprenol [47,48]. Among the product ions, that at m/z 69.2 was the most abundant and was therefore chosen for the quantitative determination of solanesol.…”

Triterpenoids

“…Cupaniol 11 is a related polyisoprenoid from Cupania latifolia. 27 The regular squalene derivatives sapelenins E 12 and F 13 have been isolated from the stem bark of Entandrophragma cylindricum. 28 Callicarpol 14 is a polyisoprenoid from the dried fruit of Callicarpa macrophylla.…”

“…30 A new triterpenoid synthase from Arabidopsis thaliana converted oxidosqualene 15 into the tricyclic triterpenoid arabidiol 16 (13aH-malabarica-17 (20),24-diene-3b,14-diol) and the corresponding 24S,25-epoxide 17. 31 Two lanosterol synthase mutants have been discovered that produce 13aH-isomalabarica-14 (27),17(20)E,24-trien-3b-ol 18, the putative precursor of isomalabaricane triterpenoids in sponges. 32 A cycloartenol synthase has been successfully converted by two mutations into a lanosterol synthase.…”