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Virginian cedarwood (Juniperus virginiana L.) essential oil is an important component of a very large number of fragrances, used in cosmetics or household products. Clary sage (Salvia sclarea L.) essential oil is well known in aromatherapy for its sedative property. The essential oils of Virginian cedarwood’s crushed barks and clary sage’s leaves were analyzed by GC/MS. Respectively, seven and seventeen compounds; representing 78% and 94.13% of the essential oils, were identified. The main components of the cedar oil are cedrene alpha (25%) and cedrol (20%). The main components of the clary sage oil are linalyl acetate (69.4%) and linalool (11.9%). Cedarwood oil exhibits significant relaxing activity, influencing physiological and biochemical parameters in human. This shows repercussions on situational stress. Virginian Cedarwood essential oil activity is compared with clary sage essential oil, which proved to be less efficient on stress relief.

This paper presents the results of the analysis investigation of the lamp oil remains from a Tang Dynasty tomb (901 AD) in Lin An County, Zhejiang Province of China. The techniques applied include direct pyrolysis gas chromatography and mass spectrometry (Py-GC/MS), Py-GC/MS with in-situ hydrolysis and methylation, as well as Py-GC/MS with double-shot method. Through the analysis, plant oil—most likely perilla oil was identified in the sample. The detection of the aromatic compounds (such as calamene, calamenene, cycloisolongifolene, 8,9-dehydro-neoisolongifolene, cadalene, cedrene, ylangene, cuparene and cedrol) indicates the presence of cedar oil and other essential oils in the lamp remains. Unexpectedly, the marker compounds of urushi including methyl 7-(2,3-dimethoxyphenyl) heptanoate, methyl 9-(2,3-dimethoxyphenyl) nonanoate and 1,2-dimethoxy-3-pentadecylbenzene were also detected in the sample.

Essential oil from Juniperus virginiana L. (eastern red cedarwood essential oil, CWO) has been used to relax mind and enhance comfort for medical purposes. Few reports showed its effect on anxiety behaviors in animal models. The present study investigated the anxiolytic effect of CWO using two anxiety tests in mice, then determined the major active constituents, examined the change of neurotransmitters after intraperitoneal (i.p.) administration. Analysis using GC/MS revealed that the CWO contained (-)-α-cedrene (28.11%), (+)-β-cedrene (7.81%), (-)-thujopsene (17.71%) and (+)-cedrol (24.58%). CWO at 400-800mg/kg increased the percentage of open arm entries and the percentage of the time spent in open arms in the elevated plus maze (EPM), suggesting that the oil has anxiolytic effect. However, it didn't show anxiolytic effect in the light-dark box (LDB) test. Tests of the cedrene did not show anxiolytic effect in either test, but rather induced anxiety-related behaviors and inhibited the locomotor activity in EPM and LDB. Cedrol produced significant anxiolytic effect in both EPM and LDB tests at 400-1600mg/kg and 800-1600mg/kg, respectively. A more significant increase in locomotor activity was observed in cedrol at 200-1600mg/kg administration than CWO. CWO increased the 5-hydroxytryptamine (5-HT) concentration at 800mg/kg, whereas it didn't affect the dopamine (DA) concentration. Cedrol significantly reduced the DA level at 100-200mg/kg and elevated the 5-HT level at 1200-1600mg/kg. Moreover, it changed the ratio of 5-hydroxyindoleacetic acid/5-HT and 3, 4-dihydroxyphenyl acetic acid/DA at 1200-1600mg/kg. CWO and cedrol, in particular might act in an anxiolytic effect through the 5-HTnergic and DAnergic pathways.

Cedrol, β-cedrene, and thujopsene are bioactive sesquiterpenes found in cedar essential oil and exert antiseptic, anti-inflammatory, antispasmodic, tonic, astringent, diuretic, sedative, insecticidal, and antifungal activities. These compounds are used globally in traditional medicine and cosmetics. The aim of this study was to investigate the inhibitory effects of cedrol, β-cedrene, and thujopsene on the activities of eight major human cytochrome P-450 (CYP) enzymes using human liver microsomes to assess potential β-cedrene-, cedrol-, and thujopsene-drug interactions. Cedrol, β-cedrene, and thujopsene were found to be potent competitive inhibitors of CYP2B6-mediated bupropion hydroxylase with inhibition constant (Ki) values of 0.9, 1.6, and 0.8 μM, respectively, comparable with that of a selective CYP2B6 inhibitor, thioTEPA (Ki, 2.9 μM). Cedrol also markedly inhibited CYP3A4-mediated midazolam hydroxylation with a Ki value of 3.4 μM, whereas β-cedrene and thujopsene moderately blocked CYP3A4. Cedrol, β-cedrene, and thujopsene at 100 μM negligibly inhibited CYP1A2, CYP2A6, and CYP2D6 activities. Only thujopsene was found to be a mechanism-based inhibitor of CYP2C8, CYP2C9, and CYP2C19. Cedrol and thujopsene weakly inhibited CYP2C8, CYP2C9, and CYP2C19 activities, but β-cedrene did not. These in vitro results indicate that cedrol, β-cedrene, and thujopsene need to be examined for potential pharmacokinetic drug interactions in vivo due to their potent inhibition of CYP2B6 and CYP3A4.

A concise entry into the bicyclic cyclopropyl ketone derivatives 5 and 6 by way of a gold-catalyzed Ohloff-Rautenstrauch-type enyne cycloisomerization is described. The required substrates were prepared by an asymmetric addition of the branched allylzinc reagent 21 to the alkynyl aldehyde 17 mediated by the deprotonated bisoxazoline (BOX) ligand 22. Compounds 5 and 6 were then converted into a host of different members of the sesquisabina- and sesquithuja families of terpenoids, inter alia with the aid of iron-catalyzed cross-coupling reactions. As the relative and absolute configuration of 5 and 6 could be unambiguously established, the synthetic samples allowed the previously unknown stereostructures of various such terpenoids to be unraveled, including cis-sesquisabinene hydrate (33), 7-epi-sesquithujene (36), sesquisabinene B (37) and epoxy-sesquithujene (45). Moreover, the preparation of 6 also constitutes a formal total synthesis of cedrene (11) and cedrol (12).

Cones/berries of Juniperus excelsa from three provenances in Balochistan, Pakistan were collected and essential oil was extracted by solvent method. Oil contents were analyzed on gas chromatographymass spectrometry (GCMS). Identification and quantification was made by using Wiley and NIST spectral library and HP Chemstation software. Quantitatively the mean cone oil yield was 5.8, 6.5 and 4.5% for Ziarat, Zarghoon Ghar and Harboi District Kalat, respectively. Ziarat being the richest in number of compounds while Harboi in compound diversity. Quantitative and qualitative similarities were found among three locations. Ziarat was found to be rich in α-pinene, cedrol, camphene, copaene, phyllocladene, ferruginol, podocarp-7-en-3-one, and pimara-8(14) 15-dien. Zarghoon Ghar was found to be rich in α-pinene, limonene, germacrene d, widdrol, phyllocladene, ferruginol, androst-4-ene-3,6-dione and Harboi was represented by α-pinene, β-myrcene, limonene, cedrene, clovene, cadinene, patchoulene, cedrol, spathulenol, abietatriene, norkaur, pimaric acid and neoabietic acid. In all, 99 compounds were reported for the first time from the oil of cones of J. excelsa in Balochistan. Keywords: Juniperus excelsa, essential oils, GCMS, Balochistan

The extraction of cedarwood oil (CWO) using liquid carbon dioxide (LC-CO(2)) was investigated and compared to supercritical fluid extraction, including the effects of extraction pressure and length of extraction. The chemical composition of the extracts was monitored over the course of the extraction as well. The cumulative yields of CWO from cedarwood chips using 80 L of carbon dioxide varied very little treatment to treatment, with all temperature/pressure combinations yielding between 3.55 and 3.88% CWO, and the cumulative yields were statistically equivalent. The rate of extraction was highest under the supercritical extraction conditions (i.e., 100 degrees C and 6000 psi). Under the liquid CO(2) conditions (i.e., 25 degrees C), the extraction rates did not vary significantly with extraction pressure. However, there were differences in the chemical composition of the collected CWO. Extractions at 100 degrees C gave a much lower ratio of cedrol/cedrene than extractions at 25 degrees C. The highest ratio of cedrol/cedrene was obtained using 25 degrees C and 1500 psi. The use of subcritical water was also investigated for the extraction of CWO as well. Although some CWO was extracted using this method, the temperature/pressure combinations that gave the highest weight percentage yields also gave oils with an off odor while those combinations that gave a higher quality oil had very low yields. It appears that the high temperatures and acidic conditions cause a dehydration of the tertiary alcohol, cedrol, to its hydrocarbon analogue, cedrene, during CO(2) or pressurized water extractions of cedarwood.

(2000). DEHYDRATION OF CEDROL TO α-CEDRENE USING COPPER(II) SULFATE AND OTHER ACIDIC SALTS. Organic Preparations and Procedures International: Vol. 32, No. 6, pp. 557-561.

Thin layer chromatography (TLC) analysis revealed that destructive distillation of Juniperus procera tree gave ten major components, whereas Croton megalocarpus tree yielded five components. This was confirmed by gas chromatography (GC). The components were isolated by column chromatography and analysed using infrared, ultra-violet, visible and mass spectroscopy (MS) techniques. The whole extract was about 30.3% of the starting material (sawdust) and consisted of 77.5% water and 22.5% oily reddish-brown layer. The extracts had alcoholic and phenolic compounds together with acids. Cedrol, a tertiary tricyclic alcohol, was found to be in the greatest proportion in the oily layer. IR spectra with a peak beyond 3000 cm −1 , UV-VIS absorption maxima at 230 nm and mass spectra with m/e 204 suggested the presence of cedrene in the extract.

The extraction of cedarwood oil (CWO) using supercritical carbon dioxide (SC-CO2) has been investigated with respect to the effects of extraction temperature and pressure, length of extraction, and age of cedarwood chips. Steam distilled and SC-CO2 derived CWOs were compared by gas chromatography and sensory evaluation. The extraction of CWO increased with extraction temperature, except at the lowest pressure utilised. The highest percentage contribution of thujopsene to the SC-CO2 derived CWO occurred with the combination of 1500 psi and 70°C or 100°C. Essentially all of the CWO was extracted from the wood matrix in the first 10 min, however, complete extraction of water required ca. 25 min. The amount of CWO extracted decreased with increasing age of the cedarwood chips. This decrease was greatest for the more volatile hydrocarbon components, thujopsene and cedrene. The mean weight percentage yields of CWO for steam distillation and SC-CO2 extraction were 1.3 and 4.4%, respectively. An experienced analytical sensory panel selected the SC-CO2 derived CWO as being more similar to the original cedarwood chips than the steam distilled CWO. Volatile collections performed on SC-CO2 extracted, steam distilled and unextracted cedarwood chips indicated that the SC-CO2 extracted chips released almost no volatiles, whereas the unextracted chips released a higher amount of volatiles. The steam distilled cedarwood chips released an intermediate level of volatiles. Copyright © 2000 John Wiley & Sons, Ltd.

The volatile leaf oil of Juniperus chinensis L., gown as ornamental tree in the plains of northern India, was examined by GC and GC-MS. Thirty-three components representing 94.8% of the oil were characterized with sabinene (19.8%), elemol (18.6%), bornyl acetate (17.5%) and limonene (14.2%) as major constituents. The oil was found to be polymorphic neither for cedrene/thujopsene/cedrol (typical juniper wood oil components) nor for phenolics such as methyl chavicol, safrole, methyl eugenol and elemicin, derived from phenyl propanoid pathway. Copyright © 2004 John Wiley & Sons, Ltd.

The volatile leaf oils of Juniperus chinensis (sensu stricto) are found to be polymorphic for cedrene, thujopsene, and cedrol as well as aromatic compounds derived from the phenyl propanoid pathway. Reports on the oil of putative J. chinensis in the literature did not correspond to the oil from China which suggests that the cultivated J. chinensis may be a selection from the species and not typical. The oil of cvltivai pyramidalis possessed some similarities to the oil of one of the J. chinensis samples, whereas die oil of var. kaizuca was very different, supporting the continued recognition of the variety status.

(2000). DEHYDRATION OF CEDROL TO α-CEDRENE USING COPPER(II) SULFATE AND OTHER ACIDIC SALTS. Organic Preparations and Procedures International: Vol. 32, No. 6, pp. 557-561.

The biohydroxylation of alpha-cedrene and of cedrol have been studied. These lead to products resulting from hydroxylation of non-activated carbon atoms, thus providing a rapid access to a potentially interesting minor component of Virginia Cedarwood Oil, which does display odoriferous properties.

Biotransformation of cedrol with 5 different strains afforded 8 previously undescribed hydroxy-cedrols. The attack came from a hemisphere centered at C-12 approximately. At two positions epimeric pairs were formed, which could be avoided by using different strains. Contrary to previous studies of other groups we found the 2-and 12-hydroxylations as main reactions. Cedrene needed prolonged fermentation and gave lower yields than cedrol. Apart from allylic hydroxylations the oxidation pattern by Corynespora cassiicola DSM 62474 of cedrene and cedrol was the same. The structures of the metabolites were elucidated by 2D NMR techniques.

A total synthesis of racemic cedrol and cedrene is described in which a key step is the intramolecular Diels–Alder reaction of alkyl cyclopentadiene 3 to give the tricyclic olefin 4. Oxidation of t...

A total synthesis of racemic cedrol and cedrene is described in which a key step is the intramolecular Diels–Alder reaction of alkyl cyclopentadiene 3 to give the tricyclic olefin 4. Oxidation of t...

1. (1) Shavings from the Eastern Red Cedar (Junuperus virginiana) were examined for three diverse biological properties, i.e. enzyme induction, procarcinogenicity and insecticidal activity. 2. (2) The ability of a cedar environment to stimulate liver drug-metabolizing enzymes in mice was confirmed by lowered values for barbiturate sleeping time. 3. (3) In susceptible strains of mice (C3H-Avy, C3H-AvyfB and CBA/J) the use of cedar shavings as bedding increased significantly the incidence of spontaneous tumors of the liver and mammary gland, and also reduced the average time at which tumors appeared. 4. (4) Cedar and some of its derivatives (Oil of Cedarwood, cedrene, cedrol) disrupted the reproductive and developmental cycle of a number of insects, including the Peanut Trash Bug (Elasmolomus sordidus), the Indian Meal Moth (Plodia interpunctella) and the Forage Mite (Tyrophagus putrescentiae).