caryophyllene and carveol

Transient receptor potential ankyrin1 (TRPA1) and transient receptor potential vanilloid 1 (TRPV1) are members of the TRP superfamily of structurally related, nonselective cation channels and mediators of several signaling pathways. Previously, we identified methyl syringate as an hTRPA1 agonist with efficacy against gastric emptying. The aim of this study was to find hTRPA1 and/or hTRPV1 activators in Agastache rugosa (Fisch. et Meyer) O. Kuntze (A.rugosa), commonly known as Korean mint to improve hTRPA1-related phenomena. An extract of the stem and leaves of A.rugosa (Labiatae) selectively activated hTRPA1 and hTRPV1. We next investigated the effects of commercially available compounds found in A.rugosa (acacetin, 4-allylanisole, p-anisaldehyde, apigenin 7-glucoside, L-carveol, β-caryophyllene, trans-p-methoxycinnamaldehyde, methyl eugenol, pachypodol, and rosmarinic acid) on cultured hTRPA1- and hTRPV1-expressing cells. Of the ten compounds, L-carveol, trans-p-methoxycinnamaldehyde, methyl eugenol, 4-allylanisole, and p-anisaldehyde selectively activated hTRPA1, with EC50 values of 189.1±26.8, 29.8±14.9, 160.2±21.9, 1535±315.7, and 546.5±73.0 μM, respectively. The activities of these compounds were effectively inhibited by the hTRPA1 antagonists, ruthenium red and HC-030031. Although the five active compounds showed weaker calcium responses than allyl isothiocyanate (EC50=7.2±1.4 μM), our results suggest that these compounds from the stem and leaves of A.rugosa are specific and selective agonists of hTRPA1.

Topics: Acetanilides; Agastache; Allylbenzene Derivatives; Anisoles; Benzaldehydes; Calcium Channels; Cell Line; Cyclohexane Monoterpenes; Eugenol; HEK293 Cells; Humans; Monoterpenes; Nerve Tissue Proteins; Plant Extracts; Plant Leaves; Plant Stems; Polycyclic Sesquiterpenes; Purines; Ruthenium Red; Sesquiterpenes; Transient Receptor Potential Channels; TRPA1 Cation Channel; TRPV Cation Channels

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