Disease relevance of BETA-CARYOPHYLLENE

• Fragrances are common causes of allergic contact dermatitis. beta-Caryophyllene is a sesquiterpene that is used as a fragrance chemical [1].
• Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis [2].

High impact information on BETA-CARYOPHYLLENE

• A locus on chromosome 6, Sesquiterpene synthase1 (Sst1), was identified for which the L. esculentum allele is associated with the biosynthesis of beta-caryophyllene and alpha-humulene [3].
• Germacrene C was found by GC-MS and NMR analysis to be the most abundant sesquiterpene in the leaf oil of Lycopersicon esculentum cv. VFNT Cherry, with lesser amounts of germacrene A, guaia-6,9-diene, germacrene B, beta-caryophyllene, alpha-humulene, and germacrene D [4].
• Both the N219A and N219L mutants of pentalenene synthase were completely inactive, while the corresponding N219D mutant had a k(cat)/K(m) which was 3300-fold lower than that of the wild-type synthase, and produced a mixture of pentalenene (2) (91%) and the aberrant cyclization product beta-caryophyllene (9) (9%) [5].
• Effects of inhibition of calcium and potassium currents in guinea-pig cardiac contraction: comparison of beta-caryophyllene oxide, eugenol, and nifedipine [6].
• Ab initio and density functional evaluations of the molecular conformations of beta-caryophyllene and 6-hydroxycaryophyllene [7].

Biological context of BETA-CARYOPHYLLENE

• 7. The inhibition of the potassium current by beta-caryophyllene oxide obviously prevents a shortening of the action potential due to the diminution of the I(Ca) [6].
• Gastric cytoprotection of the non-steroidal anti-inflammatory sesquiterpene, beta-caryophyllene [8].
• Among these, the compounds, namely, isocroctylhydrazine, 4-methyl-2-heptanone and auzulene were specific to proestrus stage and the compounds, 1-H-cyclopop-e.auzulene, caryophyllene, copanene were specific to estrus stage [9].

Anatomical context of BETA-CARYOPHYLLENE

• 1. To investigate the effects of the clove oil constituents beta-caryophyllene oxide and eugenol on the heart muscle, experiments were performed on isolated papillary muscles and on ventricular myocytes of the guinea-pig [6].
• We also tested the cytotoxicity of caryophyllene oxide, which proved inactive, and gamma-caryophyllene which was found to be active against all solid tumor cell lines tested [10].
• Both caryophyllene and alpha-terpineol showed important antiproliferative effects on K562 cells [11].
• It is concluded that alpha-pinene needs the integrity of the adrenal glands to exert its anti-inflammatory activity, as opposed to beta-caryophyllene which was also active in adrenolectomized animals [12].

Associations of BETA-CARYOPHYLLENE with other chemical compounds

• AGASTACHE FOENICULUM contains 0.1-0.3% essential oil and the main components are limonene, beta-caryophyllene, methylchavicol, and germacrene B (92% altogether) [13].
• The gas-chromatographic analyses of thyme EO indicated that carvacrol was present at 81 to 83%, p-cymene at 4.5 to 5%, gamma-terpinene at 2.6 to 3.3%, caryophyllene at 1.5 to 1.6%, beta-myrcene at 1.6%, and linalool at 1.1 to 1.2% [14].
• In the essential oil obtained from common chickweed, thin layer chromatography (TLC) revealed the well-known contact allergens borneol, menthol, linalool, 1,8-cineole, and other terpenes such as epoxy-dehydro-caryophyllene, monoterpene alcohol-ester and caryophyllene [15].
• Profiling of sesquiterpene hydrocarbons in extracts of goldenrod, Solidago canadensis, by GC-MS revealed the presence of both enantiomers of germacrene D and lesser amounts of germacrene A, alpha-humulene, and beta-caryophyllene [16].
• Gas chromatography analysis of volatiles extracted from leaves and flowers of L. camara coupled to electroantennograme recordings show that 1-octen-3-ol and beta-caryophyllene are the major chemostimuli for the antennal receptor cells of the three tsetse spp. studied [17].

Gene context of BETA-CARYOPHYLLENE

• The four conformations of beta-caryophyllene (alphaalpha, alphabeta, betaalpha, and betabeta) were investigated ab initio at the 6-31G/HF and MP2 levels and additionally with density functional methods (B3LYP/6-31G), as it concerns their relative thermodynamic stabilities [7].

Analytical, diagnostic and therapeutic context of BETA-CARYOPHYLLENE

• Caryophyllene oxide was shown to be an allergen of moderate strength and beta-caryophyllene air exposed for 10 weeks showed a weak sensitizing capacity in the local lymph node assay [1].
• This fraction had similar HPLC and GC retention times to caryophyllene oxide, suggesting comparable polarity and molecular weight [18].

References