caryophyllene-oxide and n-hexane

The essential oil extracted from Desfontaine's rupturewort, Herniaria fontanesii J. Gay subsp. fontanesii growing wildly in Tunisia, was analyzed using GC and GC-MS techniques. The free radical scavenging capacity and total phenol contents of three crude extracts having different polarities (n-hexane, ethyl acetate and methanol) were examined. Thus, a total of 35 constituents were identified in the Desfontaine's rupturewort essential oil representing 89.8% of the whole constituents. The oil was dominated by hexadecanoic acid, caryophyllene oxide, terpin-4-ol, khusimone and trans-sabinene hydrate. The total phenolic contents ranged from 16.91 to 92.27 mg of gallic acid/g of dry weight and they were found to be significantly higher in methanol than in polar ethyl acetate and hexane extracts. Correlations were observed between the phenolic contents and the antioxidant properties. Thus, the antioxidant activity of the methanol extract was superior to that of all samples tested (IC50 = 0.21 ± 0.04 mg/mL).

Topics: Acetates; Bicyclic Monoterpenes; Biphenyl Compounds; Caryophyllaceae; Free Radical Scavengers; Gallic Acid; Gas Chromatography-Mass Spectrometry; Hexanes; Methanol; Monoterpenes; Oils, Volatile; Palmitic Acid; Picrates; Plant Components, Aerial; Plant Extracts; Polycyclic Sesquiterpenes; Sesquiterpenes; Solvents; Terpenes; Tunisia

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.

Topics: Animals; Antiprotozoal Agents; Cells, Cultured; Crystallography, X-Ray; Diterpenes; Ecuador; Glycosides; Hexanes; Molecular Structure; Parasitic Sensitivity Tests; Plasmodium falciparum; Polycyclic Sesquiterpenes; Rats; Sapindaceae; Sesquiterpenes; Triterpenes; Trypanosoma brucei rhodesiense