Β-caryophyllene Alcohol Research Articles

Pharmacokinetic evaluation of β-caryophyllene alcohol in rats and beagle dogs

1. β-caryophyllene alcohol (BCPA) has shown therapeutic promise in the treatment of asthma and inflammation with low toxicity. The aim of the current study was to report the pharmacokinetic profiles of BCPA in rats and dogs.2. Following intravenous administration, BCPA exhibited moderate volumes of distribution (Vz) ranging from 5.63 to 8.97 L/kg in rats and low Vz (2.89 ± 1.12 L/kg) in dogs. Systemic plasma clearance was high in both species, resulting in a short elimination half-life ranging from 29.6 to 48.3 min. In rats, the intravenous pharmacokinetics was dose dependent. The measured oral bioavailability was low in rats for BCPA solution (1.17 ± 0.78%), suspension (1.21 ± 0.33%) and PEG formulation (6.22 ± 2.63%). The bioavailability was lower in dogs for BCPA solution (0.12 ± 0.05%) and PEG formulation (0.25 ± 0.07%), indicating significant species difference. However, treatment of plasma samples with β-glucuronidase increased the systematic exposure of BCPA as assessed from AUC (0-∞) by 24.7- or 2.62-fold in rats and dogs, respectively, which suggested glucuronidation was a significant metabolic pathway for BCPA possibly due to first-pass metabolism.3. In summary, this was the first preclinical pharmacokinetic investigation of BCPA in animals, providing vital knowledge for further preclinical research and subsequent clinical trials.

Chemical Composition of the Essential Oil from Cirsium setidens, a Korean Medicinal Plant

The objective of the present study was to investigate the chemical composition of the essential oil from Cirsium setidens. C. setidens (koryoungungqwui in Korea) is a perennial plant belonging to the Compositae family, and it is an endemic species of Korea. The essential oil obtained by hydro distillation Clevenger method from the aerial part of C. setidens was analyzed by GC and GC-MS. Ninety-two volatile flavor components, constituting 94.0 % of the total volatile composition of the essential oil, were identified in the essential oil of C. setidens. The oil was composed mainly of alcohols, ketones, esters, terpenes, carboxylic acid and hydrocarbons. Phytol (38.67 %) was the most abundant compound, followed by 6,10,14-trimethyl-2-pentadecanone (16.74 %), hexadecanoic acid (8.37 %), 1,2,15,16-diepoxyhexadecane (2.30 %), and β-caryophyllene alcohol (2.28 %).

우산나물 정유의 테르펜 화합물 분석 및 수확 연도에 따른 Sesquiterpene 화합물 변화 조사

Abstract This study was investigated the chemical composition from Syneilesis palmata essential oil and the tendency of variation of the sesquiterpene compounds according to the harvesting time. The essential oils obtained by hydro distillation from the aerial parts of Syneilesis palmata were analyzed by GC and GC-MS. Ninety-eight compounds consisting of 9 aliphatic hydrocarbons, 17 sesquiterpene hydrocarbons, 11 aliphatic aldehydes, 1 terpene aldehyde, 8 aliphatic alcohols, 4 monoterpene alcohols, 16 sesquiterpene alcohols, 3 diterpene alcohols, 6 ketones, 11 esters, 8 oxides and epoxides, 3 acids and 1 miscellaneous one were identified from the oil. Spathulenol (22.33%) was the most abundant compound, followed by β- caryophyllene (6.23%), germacrene D (5.57%), longipinane (4.10%), and epiglobulol (3.65%). The volatile composition of Syneilesis palmata was characterized by higher contents of sesquiterpene compounds, especially sesquiterpene alcohols. The total content of 13 sesquiterpene compounds was decreased significantly from 2010 to 2012. α-Caryophyllene, β-bisabolene, elemol, germacrene D, β-zingiberene, longipinane, and β-caryophyllene alcohol contents decreased, while β-bisabolol content increased during 3 years. The ecological responses to recent climate change may be influenced in the chemical components of natural plant terpenoids.Key words: Syneilesis palmata, essential oil composition, sesquiterpene compound, spathulenol, harvesting time

Direct Hydration of β-Caryophyllene

This study of β-caryophyllene hydration to produce β-caryophyllene alcohol was carried out catalyzed by strong acidic cation exchange resin NKC-9. The effects of different parameters such as agitation speed, catalyst type, catalyst loading, mass ratio of the reactants, temperature, and reaction time on the conversion of β-caryophyllene and yield of β-caryophyllene alcohol in a stirred-tank reactor have been investigated to obtain the optimal conditions. Under the optimal conditions (catalyst loading 20%(w/w), nβ-caryophyllene/nwater 1/1, reaction temperature 363.15 K, reaction time 30–40 min), the experiment was then carried out in a pilot-scale stirred tank reactor and in a novel pilot-scale jet reactor respectively to achieve excellent performance. The β-caryophyllene alcohol has been purified by rectifying column and recrystallized. A pseudohomogeneous (PH) model was used to correlate the kinetic data in the temperature range from 333.15 to 363.15 K. The estimated kinetic parameters make the calculated...

Fragrance material review on β-caryophyllene alcohol

A toxicologic and dermatologic review of β-caryophyllene alcohol when used as a fragrance ingredient is presented.

Sesquiterpenes From a New Zealand Sponge of the Genus Eurypon

A cytotoxic sesquiterpene (1) with a tricyclo [6.3.1.0.2,5] dodecane skeleton has been isolated from the extract of a New Zealand Eurypon sp. of sponge. Two derivatives, (2) and (3), of this sesquiterpene have also been isolated, probably as artefacts arising during the isolation procedure. The structure of a spiro sesquiterpene (4), also obtained from the sponge extract, has been determined. Previously published n.m.r. assignments for β-caryophyllene alcohol (5) have been revised.

テルペン類の合成ゼオライトを触媒として用いる水和反応 ＩＩ 単環および鎖状テルペン炭化水素類の合成ゼオライト触媒存在下，クロロ酢酸類による水和反応

The hydration of 1-p-menthene [1], 3-p-menthene [2], 1, 8-p-menthadiene [3], isoprene [4] mycrene [5], dihydromycrene [6], longifolene C7J and p-caryophyllene C8D with mono-, di- and trichloroacetic acids in the presence of synthetic zeolites (A-3, A-4, A-5, F-9 and TSZ-301) was investigated. The hydration of[1], [2] and [3]gave cis-1-p-menthanol [1 0 ], trans-4-p-menthanol [13] and a-terpineol [ 14 ], respectively as a main product with high conversion (89-400%, at best) and high selectivity. Hydration of C 4 J gave geraniol [15] as a major product. Linalool C. /8 J and myrcenol [19] were obtained as major two products from C 5 J. Under particular conditions, the [18]/[19] ratio was 57: 28 or 46: 42. Dihydromyrcenol [20]was obtained from [6] as a main product, amounting to 80% of the hydration products under the best conditions. Longicamphene hydrate [21]was obtained in high selectivity (86% and 92%) from [7]. β-Caryophyllene alcohol [24] was obtained from [8] as a main product, amounting to 84% of the hydration products under the best conditions.

Hydration Products of Nine Sesquiterpene Hydrocarbons

The homogeneous mixtures of sesquiterpene hydrocarbons as β-caryophyllene (1), humulene (2), β-and γ-elemenes [(3) and (4)], α- and β-selinenes [(5) and (6)], thujopsene (7), longifolene (8) or α cedrene (9), and acetic acid were passed through in glass tube packed with cation exchange resin at room temperature. The hydration of (1) took place to give β-caryophyllene alcohol (10), dihydroneocloven-4β-ol, and dihydrocloven-9β-ol (12), along with isomerization products, neoclovene (1a) and clovene (1b). Humulol (13), was obtained by hydration of (2) in high selectivity. Only elemol (14) was obtained from (3) and (4). A similar hydration of (5) and (6) was found to afford three products, γ-eudesmol (15), α-eudesmol (16), and β-eudesmol (17). And also, the hydration of (7) gave widdrol (18), along with widdrene (7a), isowiddrene (7b), and β-chamigrene (7c). Compound (8) or (9) has no reaction to an offer. * Stadies on the Hydration of Terpenes. XVI.

Sesquiterpenes from three Senecio species

Three succulent Senecio species afforded, in addition to known compounds, two further bisabolene derivatives, a norsesquiterpene and a diol related to β-caryophyllene alcohol, which, however, has a different stereochemistry. Structures were elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomic relevance of the results is discussed briefly.

X-ray studies in the caryophyllene series. The chloride and bromide from β-caryophyllene alcohol

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Clovene and β-caryophyllene alcohol

Clovene and β-caryophyllene alcohol