caryophyllene and estragole

The essential oils (EOs) from the Brazilian species Croton zehntneri, Pterodon emarginatus and Schinopsis brasiliensis were examined for their chemical constituents, and antioxidant and antimicrobial activities. The composition of EOs was determined by using gas chromatography coupled with mass spectrometry analysis, while the antioxidant activity was evaluated through the 1,1-diphenyl-2-picrylhydrazyl (DPPH) and oxygen radical absorbance capacity (ORAC) assays. Furthermore, the antimicrobial activity was investigated against Escherichia coli and Pseudomonas aeruginosa (both Gram-negative), Staphylococcus aureus (Gram-positive) and Candida parapsilosis (fungus). The main components of C. zehntneri, P. emarginatus and S. brasiliensis were identified as estragole, trans-anethole, β-caryophyllene and myrcene. Among the EOs, P. emarginatus showed the highest antioxidant activity, with an IC50 of 7.36 mg/mL and a Trolox equivalent antioxidant capacity of 3748 μmol/g determined by DPPH and ORAC assays, respectively. All EOs showed low activities against the bacterial strains tested, whereas the C. zehntneri oil and its main constituent estragole exhibited an appreciable antifungal activity against C. parapsilosis.

Topics: Acyclic Monoterpenes; Alkenes; Allylbenzene Derivatives; Anacardiaceae; Anisoles; Anti-Bacterial Agents; Antifungal Agents; Candida; Croton; Escherichia coli; Fabaceae; Free Radical Scavengers; Mass Spectrometry; Microbial Sensitivity Tests; Monoterpenes; Oils, Volatile; Polycyclic Sesquiterpenes; Pseudomonas aeruginosa; Sesquiterpenes; Staphylococcus aureus

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 the chemical composition and nematicidal activity of essential oil of Agastache rugosa flowering aerial parts against the root knot nematode, Meloidogyne incognita, and to isolate and identify any nematicidal constituents from the essential oil. The essential oil of A. rugosa aerial parts was obtained by hydrodistillation and analyzed by GC-FID and GC-MS. A total of 37 components of the essential oil were identified, with the principal compounds being methyleugenol (50.51%), estragole (8.55%), and eugenol (7.54%), followed by thymol (3.62%), pulegone (2.56%), limonene (2.49%) and caryophyllene (2.38%). Based on bioactivity-guided fractionation, the three active constituents were isolated from the essential oil and identified as methyleugenol, estragole and eugenol. The essential oil of A. rugosa exhibited strong nematicidal activity against M. incognita, with a LC50 value of 47.3 μg/mL. The components eugenol (LC50 = 66.6 μg/mL) and methyleugenol (LC50 = 89.4 μg/mL) exhibited stronger nematicidal activity against M. incognita (LC50 = 185.9 μg/mL). The results indicate that the essential oil of A. rugosa aerial parts and its constituent compounds have potential for development into natural nematicides for control of the root knot nematode.

Topics: Agastache; Allylbenzene Derivatives; Animals; Anisoles; Antinematodal Agents; Cyclohexane Monoterpenes; Cyclohexenes; Eugenol; Gas Chromatography-Mass Spectrometry; Lethal Dose 50; Limonene; Monoterpenes; Oils, Volatile; Plant Oils; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes; Thymol; Tylenchoidea

The essential oil composition of Feronia elephantum Correa (family: Rutaceae) was examined by capillary gas chromatography (GC) and gas chromatography-mass spectroscopy (GC-MS). The analysis revealed the presence of 24 constituents, of which 18 constituents were identified. Trans-anethole (57.73%) and methyl chavicol (37.48%) were the major compounds, while cis-anethole, p-anisaldehyde, (E)-jasmone, methyl eugenol, β-caryophyllene, linalool and (E)-methyl isoeugenol were also present as the minor constituents.

Topics: Acyclic Monoterpenes; Allylbenzene Derivatives; Anisoles; Benzaldehydes; Chromatography, Gas; Cyclopentanes; Eugenol; Gas Chromatography-Mass Spectrometry; Monoterpenes; Oils, Volatile; Oxylipins; Polycyclic Sesquiterpenes; Rutaceae; Sesquiterpenes

The chemical components and their relative contents of essential oil in different parts (stems, leaves and flowers) of Agastache rugosa have been analyzed by GC-MS technique, and 32 kinds of chemical structures in these three kinds of oils have been identified. Among which, it included 24 kinds in leaf-oil, 27 in stem-oil and 22 in flower-oil. The principal components in all these three kinds of oils were methylchavicol (60.01-88.43%), and other important components were d-limonene, caryophyllene, hexadecanoic acid, linoleic acid, octahydro-7-methyl-methylene-4-(1-methylethyl)-1H-cyclopenta [1, 3] cyclopropa [1, 2] benzene, etc.

Topics: Agastache; Allylbenzene Derivatives; Anisoles; Cyclohexenes; Flowers; Limonene; Oils, Volatile; Plant Leaves; Plant Stems; Plants, Medicinal; Polycyclic Sesquiterpenes; Sesquiterpenes; Terpenes