caryophyllene-oxide and bornyl-acetate

Bioassay guided fractionation of Cinnamon tamala leaf extracts yielded bornyl acetate (1), caryophylene oxide (2), p-coumaric acid (3) and vanillic acid (4) using A-2780 human ovarian cancer cell lines. The structures of the isolated compounds were confirmed through spectroscopic techniques (EIMS, (1)H and (13)C NMR). Compound 1 exhibited highest cytotoxicity with 90.16 ± 1.06% inhibition (IC50=5.30 x 10(-4) mg/ml) followed by compound 2 (84.40±1.53% inhibition; IC50=8.94 x 10(-3)mg/ml), while compounds 3 and 4 were inactive in the bioassay.

Topics: Animals; Antineoplastic Agents, Phytogenic; Camphanes; Carcinoma; Cell Line, Tumor; Cell Proliferation; Cell Survival; Cinnamomum; Coumaric Acids; Cricetinae; Drug Screening Assays, Antitumor; Female; Humans; Ovarian Neoplasms; Plant Extracts; Plant Leaves; Polycyclic Sesquiterpenes; Propionates; Sesquiterpenes; Vanillic Acid

The aim of this research was to determine chemical composition and insecticidal activity of the essential oil of Illicium pachyphyllum fruits against two grain storage insects, Sitophilus zeamais and Tribolium castaneum, and to isolate any insecticidal constituents from the essential oil. The essential oil of I. pachyphyllum fruits was obtained by hydrodistillation and analyzed by GC-MS. A total of 36 components of the essential oil were identified, with the principal compounds in the essential oil being trans-ρ-mentha-1(7),8-dien-2-ol (24.56%), D-limonene (9.79%), caryophyllene oxide (9.32%), and cis-carveol (5.26%) followed by β-caryophyllene (4.63%) and bornyl acetate. Based on bioactivity-guided fractionation, the three active constituents were isolated and identified as trans-ρ-mentha-1(7),8-dien-2-ol, D-limonene and caryophyllene oxide. The essential oil of I. pachyphyllum fruits exhibited contact toxicity against S. zeamais and T. castaneum adults, with LD(50) values of 17.33 μg/adult and 28.94 μg/adult, respectively. trans-p-Mentha-1(7),8-dien-2-ol (LD(50) = 8.66 μg/adult and 13.66 μg/adult, respectively) exhibited stronger acute toxicity against S. zeamais and T. castaneum adults than either caryophyllene oxide (LD(50) = 34.09 μg/adult and 45.56 μg/adult) and D-limonene (LD(50) = 29.86 μg/adult and 20.14 μg/adult). The essential oil of I. pachyphyllum possessed fumigant toxicity against S. zeamais and T. castaneum adults with LC(50) values of 11.49 mg/L and 15.08 mg/L, respectively. trans-p-Mentha-1(7),8-dien-2-ol exhibited stronger fumigant toxicity against S. zeamais and T. castaneum adults, respectively, with LC(50) values of 6.01 mg/L and 8.14 mg/L, than caryophyllene oxide (LC(50) = 17.02 mg/L and 15.98 mg/L) and D-limonene (LC(50) = 33.71 mg/L and 21.24 mg/L). The results indicate that the essential oil of I. pachyphyllum fruits and its constituent compounds have potential for development into natural insecticides or fumigants for the control of insects in stored grains.

Topics: Animals; Camphanes; Cyclohexane Monoterpenes; Cyclohexenes; Edible Grain; Food Preservation; Food Storage; Fruit; Gas Chromatography-Mass Spectrometry; Illicium; Inhibitory Concentration 50; Insecticides; Limonene; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Tribolium; Weevils

To analyze the chemical components of the essential oil extracted from six cultivars' Juhua (Zaogongju, Wangongju, Huangyaoju, Chuju, Xiaoboju and Daboju) produced in Anhui province of China, which were breed from Chrysanthemum morifolium, and to provide scientific basis for quality control.. The essential oils of the six cultivars'Juhua were extracted by water-steam distillation and separated by GC capillary column chromatography. The components were quantitatively determined with normalization method, and identified by GC-MS.. From Zaogongju, Wangongju, Huangyaoju, Chuju, Xiaoboju and Daboju, 247, 226, 246, 182, 216 and 122 chromatographic peaks were detected, among them 75, 54, 78, 50, 53 and 43 components were identified,which were composed of 85.67%, 82.80%, 81.38%, 73.22%, 71.51% and 72.87% of the total essential oil, respectively.. Monoterpenoid compounds were higher more than sesquiterpenoid compounds in the five juhua except for Chuju. There was no difference in the constituents of essential oil of Zaogongju and Wangongju. And verbenyl acetate was the main chemical constituent and composed of 32.10% and 37.85% of the total essential oil, respectively. (1R)-Camphor and bisabolol oxide A were the main chemical constituents in Huangyaoju, which were composed of 28.70% and 12.58% of the total essential oil, respectively. beta-Selinene and borneol were the main chemical constituents in Chuju, which were composed of 17.85% and 12.84% of the total essential oil, respectively. Eucalyptol was the main chemical constituent in Xiaoboju, which were composed of 21.33%. Verbene oxides and chrysanthenone were composed of 25.32% and 8.26% of the total essential oil, respectively, in the Daboju. The common chemical constituents were camphene, borneol, bornyl aceate, (1R)-camphor, (-)-4-terpineol, alpha-terpineol, eucalyptol, cis-caryophyllene, caryophyllene oxide, juniper camphor, beta-sesquiphellandrene, alpha-curcumene and beta-farnesene in the six cultivars' Juhua produced in Anhui province of China. The resultant data provided the further evidences to distinguish Juhua' cultivars and scientific basis for quality control of Juhua.

Topics: Bicyclic Monoterpenes; Boranes; Camphanes; Camphor; China; Chrysanthemum; Cyclohexanols; Eucalyptol; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Eudesmane; Terpenes; Tetrahydronaphthalenes