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Rhizosphere microorganisms interact with plant roots by producing chemical signals that regulate root development. However, the distinct bioactive compounds and signal transduction pathways remain to be identified. Here, we showed that sesquiterpenes are the main volatile compounds produced by plant-beneficial Trichoderma guizhouense NJAU4742. Inhibition of sesquiterpene biosynthesis eliminated the promoting effect of this strain on root growth, indicating its involvement in plant-fungus cross-kingdom signalling. Sesquiterpene component analysis identified cedrene, a highly abundant sesquiterpene in strain NJAU4742, to stimulate plant growth and root development. Genetic analysis and auxin transport inhibition showed that the TIR1 and AFB2 auxin receptors, IAA14 auxin-responsive protein, and ARF7 and ARF19 transcription factors affected the response of lateral roots to cedrene. Moreover, the AUX1 auxin influx carrier and PIN2 efflux carrier were also found to be indispensable for cedrene-induced lateral root formation. Confocal imaging showed that cedrene affected the expression of pPIN2:PIN2:GFP and pPIN3:PIN3:GFP, which might be related to the effect of cedrene on root morphology. These results suggested that a novel sesquiterpene molecule from plant-beneficial T. guizhouense regulates plant root development through the transport and signalling of auxin.

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.

The naturally occurring (−)-α-cedrene exhibits a weak woody and cedarlike odor. In contrast, cis-cedrene acetonide, which is a derivative of cedrene, is an extremely powerful semisynthetic aroma mo...

The main objective of this study was to extract the essential oils from Clerodendrum formicarum and Syzygium cordatum in order to determine the anticancer activity and establish the chemical constituents of that kind of essential oils. Hence, we have used hydrodistillation method to obtain the desired extracts or samples of essential oils. Indeed, the assessment of the anticancer activities showed that, at 100 µg/mL, the essential oils from S. cordatum inhibited the proliferation (98.2%) of breast cancer (MCF-7) cells. In the same context, the essential oils from C. formicarum also inhibited the proliferation (98.9%) of breast cancer (MCF-7) cells. We have additionally determined the chemical composition of the essential oils by GC-MS and identified 17 compounds in C. formicarum including caryophyllene (18.6%), (E)-3,7-dimethylocta1,3,6-triene (7.6%), β-Myrcene (6.2%), and [1S-(1α, 7α, 8α)]-1,8a-dimethyl-7-(1-methylethenyl)- 1,2,3,5,6,7,8,8a-octahydronaphthalene (5.6%) as major compounds. We have observed an unknown compound (25%) in the essential oils from C. formicarum (H-12) The chemical analysis showed 28 compounds in S. cordatum (HE-9) essential oils such as caryophyllene (7.2%) and cedrene (6.7%) as major compounds

The objective of this work was to analyze four essential oils (EOs) from Rhododendron species in China and evaluate their repellent activity against Tribolium castaneum, Lasioderma serricorne, and Liposcelis bostrychophila adults. These four EOs from Rhododendron species, including R. capitatum, R. przewalskii, R. mucronulatum, and R. micranthum, were obtained by hydrodistillation. Major components of four EOs were identified as sesquiterpenoids by GC-MS. The relatively high components included cedrene (22.20%), borneol (36.64%), 4-(2,3,4,6-tetramethylphenyl)-3-buten-2-one (27.74%), and germacrene D (27.60%). Repellent activity of EOs from Rhododendron species was investigated against T. castaneum, L. serricorne, and L. bostrychophila adults for the first time. In this study, EOs had demonstrated their repellent activities against three stored-product insects in 2- and 4-h exposure. The above results can not only provide comprehensive utilization of plant resources of Rhododendron genus but also establish a very good perspective of novel application to control stored-product insects.

Volatile constituents from waterlogged cypress wood were investigated by means of GC–MS to examine the alteration of terpenoids during anaerobic conditions. The results were evaluated by comparison with the terpenoid composition of recent cypress wood Cupressus sempervirens. The essential oils contained largely monoterpenoids (carvacrol, carvacrol methyl ether, p-cymene), sesquiterpenoids (α-cedrol, cedrene) and a diterpenoid (manool). The terpenoid characteristics strongly supported the relationship to the C. sempervirens wood. While sesquiterpenoids, i.e. α-cedrol, remained almost intact in archaeological wood, in particular monoterpenoids but also the diterpenoid underwent considerable alteration. The same compounds in archaeological- and extant woods allow the conclusion that the diagenetic transformations took place in monoterpenoid moiety in waterlogged wood. A novel degradation of carvacrol methyl ether and carvacrol was detected, and an alteration pathway was suggested in this study. Sesquiterpenoids were detected in higher amounts as unaltered forms in archaeological samples, and it was shown that these compounds were very resistant and stable. Moreover, because of a remarkable decrease in its amount, the diterpenoid manool experienced degradation or chemical changes in archeological samples. It can be concluded that alteration of Cupressus wood compounds probably occurred under waterlogged anaerobic conditions leading to reductive reactions, demethylation and dehydroxlylation of monoterpenoids forming monoterpene- and aromatic compounds. The volatile constituents of archeological wood can serve as valuable chemo-systematic markers for waterlogged archaeological softwoods adequately buried in an anaerobic environment.

Early and non-destructive identification of fertile (F) eggs is a difficult task in the process of breeding laying hens. The odors emitted from unfertilized (UF), infertile (IF), and fertile (F) eggs were characterized by solid-phase microextraction / gas chromatograph-mass spectrometry (SPME/GC-MS) and electronic nose (E-nose) to determine their differences by principal component, partial least squares, and canonical discriminant analyses. RESULTS A total of 14 volatiles were identified in unhatched shell white Leghorn eggs, such as nonanal, decanal, 6-methyl-5-hepten-2-one, and 6,10-dimethyl-5,9-undecadien-2-one. Cedrene and decanal contributed greatly to the classification of UF and fertilized (Fd)/IF eggs; cedrene, decanal, 1-octanol and hexanal contributed greatly to the distinction between UF and IF eggs; heptanal might be the potential marker to determine F/IF eggs. P40/1, P10/2, P10/1, TA/2, T40/2 and T30/1, P30/1, P40/2, PA/2, T40/2 mostly contributed to the distinction between UF and Fd eggs and between F and IF eggs, respectively. Canonical discriminant analysis presented superior differentiating efficiency for almost all groups, and the odor differences between UF and Fd eggs were significantly larger than the differences between F and IF eggs. CONCLUSION Solid-phase microextraction / gas chromatograph-mass spectrometer combined with E-nose may have the potential to non-destructively distinguish UF, F, and IF eggs, which will provide a new perspective to understand the differences among them. ? 2018 Society of Chemical Industry

Rhizosphere microorganisms interact with plant roots by producing chemical signals to regulate root development. However, the involved distinct bioactive compounds and the signal transduction pathways are remaining to be identified. Here, we show that sesquiterpenes (SQTs) are the main volatile compounds produced by plant beneficialTrichoderma guizhouenseNJAU 4742, inhibition of SQTs synthesis in this strain indicated their involvement in plant-fungus cross-kingdom signaling. SQTs component analysis further identified the cedrene, a high abundant SQT in strain NJAU 4742, could stimulate plant growth and root development. Genetic analysis and auxin transport inhibition showed that auxin receptor TIR1, AFB2, auxin-responsive protein IAA14, and transcription factor ARF7, ARF19 affect the response of lateral roots to cedrene. Moreover, auxin influx carrier AUX1, efflux carrier PIN2 were also indispensable for cedrene-induced lateral root formation. Confocal imaging showed that cedrene affected the expression ofpPIN2:PIN2:GFPandpPIN3:PIN3:GFP, which may be related to the effect of cedrene on root morphology. These results suggest that a novel SQT molecule from plant beneficialT. guizhouensecan regulate plant root development through auxin transport and signaling.One-sentence SummaryCedrene, a high- abundance sesquiterpenes produced by plant beneficialTrichoderma guizhouenseNJAU 4742, stimulatesArabidopsislateral root formation and primary root elongation by relying on auxin signaling pathway and auxin transporter PIN2 and AUX1.

Temperature stress is becoming the major concern for plant scientists worldwide due to climate change. Temperature stress has devastating effects on plant growth and metabolism. The aim of the study was to investigate the effect of climatic seasonal change on the yield and composition of essential oil of the plant, Achillea fragrantissima. The gas chromatography-mass spectrometry (GC-MS) used to analyze the essential oil collected during dry and wet seasons revealed it has 25 compounds. The major compounds were santolina alcohol (5.31), camphor (4.3), and cedrene (9.01) during winter months, while the percentages of α-cubebene (17.1%), spathulenol (1.54) and globulol (5.2) were highest during summer season. The analysis of essential oil in the two seasons revealed that there are different amounts and composition of essential oils. The antioxidant activity of the essential oil of the plant shows higher activity of IC50 0.11±0.01g/L and Ec50 0.25±0.02 g/L during winter than in summer. However, the reducing capacity of standard substances used (ascorbic acid and α-Tecopherol) were 0.033±0.001 and 0.93±0.07 g/L for DPPH and 0.091±0.002 and 0.026±0.002 g/L for FRAP method, respectively. These results showed that A. fragrantissima is a natural source of active compounds, and antioxidant properties, and the difference in chemical composition leads to changes in the antioxidant activity of the plant, which contributes to seasonal change. Key words: Achillea fragrantissima, antioxidant, seasonal vibration, essential oil.

The seminal synthesis of the sesquiterpene (±)-α-cedrene reported by Wender in 1981 offers a uniquely short and elegant access to the bridged-tricyclic target compound by exploiting an intramolecular arene-olefin photocycloaddition. However, the synthesis was performed only in the racemic series so far. This synthesis was now re-investigated and the catalytic methods for the enantioselective preparation of the chiral key intermediate were evaluated. It was found that Cu-catalyzed allylic substitution of a cinnamyl chloride with MeMgBr in the presence of a Taddol-derived chiral phosphine-phosphite ligand affords the corresponding (1-methylallyl)arene with high enantioselectivity (94% ee). Hydroboration and subsequent Suzuki coupling gave (R)-curcuphenol methyl ether from which (–)-α-cedrene was prepared along the route paved by Wender.

Sesquiterpenes are an important class of biogenic volatile organic compounds (BVOCs) and have a high secondary organic aerosol (SOA) forming potential. However, SOA formation from sesquiterpene oxidation has received less attention compared to other BVOCs such as monoterpenes, and the underlying mechanisms remain poorly understood. In this work, we present a comprehensive experimental investigation of the ozonolysis of α-cedrene both in a glass flow reactor (27–44 s reaction times) and in static Teflon chambers (30–60 min reaction times). The SOA was collected by impaction or filters, followed by analysis using attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy and electrospray ionization mass spectrometry (ESI-MS), or measured online using direct analysis in real-time mass spectrometry (DART-MS) and aerosol mass spectrometry (AMS). The slow evaporation of 2-ethylhexyl nitrate that was incorporated into the SOA during its formation and growth gives an estimated diffusion coefficient of 3 × 10−15 cm2 s−1 and shows that SOA is a highly viscous semisolid. Possible structures of four newly observed low molecular weight (MW ≤ 300 Da) reaction products with higher oxygen content than those previously reported were identified. High molecular weight (HMW) products formed in the early stages of the oxidation have structures consistent with aldol condensation products, peroxyhemiacetals, and esters. The size-dependent distributions of HMW products in the SOA, as well as the effects of stabilized Criegee intermediate (SCI) scavengers on HMW products and particle formation, confirm that HMW products and reactions of SCI play a crucial role in early stages of particle formation. Our studies provide new insights into mechanisms of SOA formation and growth in α-cedrene ozonolysis and the important role of sesquiterpenes in new particle formation as suggested by field measurements.

Quantities of waste solar cells have been produced due to their widespread sustainable energy applications. Due to the complicated composition of waste solar cells, the disposal of waste solar cells has been the hot spot of sustainable development and environmental protection research. To our knowledge, little information has been reported about the disposal of waste solar cells. For the safe disposal of waste solar cells, and to produce economic benefits, the present study applied the density functional theory to design the transformation pathways of organics in waste solar cells. The ethylene-vinyl acetate copolymer and polyethylene terephthalate of waste solar cells were transformed to 3,6,8,8-tetramethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulene (cedrene). It is the precursor of precious wound-healing medicine. The transformation pathways exhibited a total energy barrier of 58.79 kcal/mol, and thermodynamic calculations indicated the temperature required for breaking this energy barrier was 777.50 K. 3,6,8,8-Tetramethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulene was produced by vacuum heating at a temperature of 778.15 K, and the material had the most substantial proportion that accounted for 19.85 wt% in the products of vacuum heating. This paper provides insight into preparing the raw materials of medicine from the nonmetallic material of waste solar cells.

Soybean, Glycine max (L.), in the field is very susceptible to infestation by sweetpotato whitefly, Bemisia tabaci (Gennadius). Preference for oviposition by whitefly in two soybean genotypes was evaluated, and a profile of volatile compounds in healthy plants was obtained. The average number of eggs per square centimeter was 4.1 to 13.7 in ‘Nainari’ variety and 15.1 to 28.4 in an experimental line. Trichome averaged 6.5 per square centimeter in Nainari and 6.8 in the experimental line. The average length of trichomes of Nainari was 311 microns and in the experimental line was 342. Solid-phase microextraction and gas chromatography-mass spectrometry were used to obtain the profile of volatile compounds in two Nainari soybean genotypes and one experimental line: cis-3-hexenyl acetate; cis-3-methyl-1,3-pentadiene; 4-methyl-1,3-pentadiene; cis-3-hexenyl valerate; cis-2-hexen-1-ol; 9-ethyl-9-heptyloctadecane; tetradecane; tridecane; and 2,6-bis(1,1-dimethylethyl)-4-(1-oxopropyl) phenol. In plants infested with whitefly eggs and nymphs, eight compounds were identified in Nainari and seven in the experimental line: M-xylene; 1-octen-3-ol; d-limonene; cedrene; propanoic acid, 2-methyl-, 2-methyl propyl ester; 3-methylnonane; longifolene; caryophyllene; 2,5-cyclohexadiene-1,4-dione, 2,6-bis (1,1-dimethylethyl)-; alpha-farnesene; pentanoic acid, 2,2,4-trimethyl-3-carboxyisopropyl, isobutyl ester, and 2,6-bis(1,1-dimethylethyl)-4-(1-oxopropyl) phenol. Differences in the profile of volatile compounds in healthy Nainari plants might explain oviposition repellency.

Antrodia cinnamomea is a precious edible mushroom endemic to Taiwan that has been claimed to have significant health promotion activities. Antrodia salmonea is a new species of the genus Antrodia . In this study, we compared the metabolites and bioactivity of A. cinnamomea and A. salmonea fruiting bodies. The volatiles of A. cinnamomea and A. salmonea were characterized and 3,4,5-trimethoxybenzaldehyde was found to be the most abundant compound in A. cinnamomea ; the other abundant compounds were δ -guaiene, isolongifolene, 1-octen-3-ol, 4-terpinenol, α -guaiene, and p-cymene. In A. salmonea , the main volatiles were α -cedrene, 1-octen-3-ol, D-limonene, cadinadiene, germacrene D, isolongifolene, and α -muurolene. Furthermore, five ergostane-type triterpenoids and two lanostane-type triterpenoids were selected as index compounds characterizing A. cinnamomea and A. salmonea extracts. The content of each compound varied between the two species. (R,S)-antcin B was the most abundant compound in A. cinnamomea fruiting bodies (75.18 ± 0.11 µg/mg). However, ( R,S )-antcin C (184.85 ± 0.96 µg/mg) was the major triterpenoid in the A. salmonea fruiting body. Furthermore, two compounds, antcin M and methyl antcinate K, were only present in the A. salmonea fingerprint; therefore, antcin M and methyl antcinate K may be important for distinguishing between A. cinnamomea and A. salmonea fruiting bodies. Finally, examination of anti-inflammation activity and cytotoxicity showed that A. salmonea had more anti-inflammatory activity than A. cinnamomea ; however, A. salmonea was more cytotoxic than A. cinnamomea . In conclusion, the composition and bioactivity of the fruiting bodies of A. cinnamomea and A. salmonea varies. Therefore, it is recommended that further toxicological evaluation and investigation of the biological activity of A. salmonea is carried out to ensure its safe and efficacious use as an alternative to A. cinnamomea .

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.

The growth-inhibiting activities of the essential oils extracted from Platycladus orientalis leaves and stems were examined against intestinal bacteria. The leaf oil exhibited a strong response against Clostridium difficile and C. perfringens at 5.0 mg/disc, but the stem oil showed no inhibitory activity against intestinal bacteria. The oils from P. orientalis leaves and stems were analyzed by GC-Mass spectroscopy. The main constituents of the essential oil in P. orientalis leaves: α-pinene (18.5%), cedrene (13.6%), α-cedrol (11.3%), β-caryophyllene (10.2%), 3-carene (8.2%), and α-terpinyl acetate (5.1%), and in the stems: α-pinene (17.7%), 3-carene (16.3%), β-caryophyllene (13.4%), β-phellandrene (9.5%), β-selinene (6.5%), and α-cedrol (6.1%). The cedrene isomers showed significant (33.1–34.7 mm) inhibitory effect against C. difficile and C. perfringens and moderate inhibitory effect against Escherichia coli at 2.0 mg/disc. The oil of P. orientalis leaves, in which cedrene isomers are the major component, could be used as a selective inhibitor against harmful bacteria.

This study aimed to evaluate the potential of α-cedrene as a new anti-obesity drug by characterizing absorption, metabolism and pharmacokinetics in rats. α-Cedrene was administered intravenously (10 and 20 mg/kg) and orally (50 and 100 mg/kg) to female and male Sprague-Dawley rats. Blood, tissues, urine, and feces were collected at predetermined times. α-Cedrene concentrations were determined by a validated gas chromatography-tandem mass spectrometry (GC-MS/MS). A gas chromatography-mass selective detection (GC-MSD) method was used to identify the major metabolite. After i.v. injection, α-cedrene exhibited a rapid clearance (98.4-120.3 ml/min/kg), a large distribution volume (35.9-56.5 l/kg), and a relatively long half-life (4.0-6.4 h). Upon oral administration, it was slowly absorbed (Tmax = 4.4 h) with bioavailability of 48.7-84.8%. No gender differences were found in its pharmacokinetics. Upon oral administration, α-cedrene was highly distributed to tissues, with the tissue-to-plasma partition coefficients (Kp) far greater than unity for all tissues. In particular, its distribution to lipid was notably high (Kp = 132.0) compared to other tissues. A mono-hydroxylated metabolite was identified as a preliminary metabolite in rat plasma. These results suggest that α-cedrene has the favorable pharmacokinetic characteristics to be further tested as an anti-obesity drug in clinical studies.

The rate coefficients of the reaction of ozone with the four atmospherically relevant sesquiterpenes β-caryophyllene, α-humulene, α-cedrene and isolongifolene were investigated at 295 ± 2 K and atmospheric pressure by at least two independent experimental investigations for each reaction. Relative rate experiments were carried out in a flow tube using two different experimental approaches with GC-MS detection (RR 1) and PTR-MS analysis (RR 2) as the analytical techniques. Absolute rate coefficients were determined in a stopped-flow experiment following the ozone depletion by means of UV spectroscopy. The average rate coefficients from the combined investigations representing the mean values of the different experimental methods are (unit: cm(3) molecule(-1) s(-1)): k(O3+β-caryophyllene) = (1.1 ± 0.3) × 10(-14) (methods: RR 1, RR 2, absolute), k(O3+α-humulene) = (1.2 ± 0.3) × 10(-14) (RR 1, RR 2), k(O3+α-cedrene) = (1.7 ± 0.5) × 10(-16) (RR 2, absolute) and k(O3+isolongifolene) = (1.1 ± 0.5) × 10(-17) (RR 2, absolute). The high ozonolysis rate coefficients for β-caryophyllene and α-humulene agree well with the results by Shu and Atkinson (Int. J. Chem. Kinet., 1994, 26) and lead to short atmospheric lifetimes of about two minutes with respect to the ozone reaction. The relatively small rate coefficients for α-cedrene and isolongifolene differ from the available literature values by a factor of about 2.5-6. Possible reasons for the deviations are discussed. Finally, calibrated sesquiterpene FT-IR spectra were recorded for the first time.

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.

A solvent-dependent oxidative dearomatization-induced divergent [5+2] cascade approach to bicyclo[3.2.1]octanes was described. This novel protocol enables a facile synthesis of a series of diversely functionalized ent-kaurene and cedrene-type skeletons in good yields and excellent diastereoselectivities.

Background Genome mining facilitated by heterologous systems is an emerging approach to access the chemical diversity encoded in basidiomycete genomes. In this study, three sesquiterpene synthase genes, GME3634, GME3638, and GME9210, which were highly expressed in the sclerotium of the medicinal mushroom Lignosus rhinocerotis, were cloned and heterologously expressed in a yeast system. Results Metabolite profile analysis of the yeast culture extracts by GC–MS showed the production of several sesquiterpene alcohols (C15H26O), including cadinols and germacrene D-4-ol as major products. Other detected sesquiterpenes include selina-6-en-4-ol, β-elemene, β-cubebene, and cedrene. Two purified major compounds namely (+)-torreyol and α-cadinol synthesised by GME3638 and GME3634 respectively, are stereoisomers and their chemical structures were confirmed by 1H and 13C NMR. Phylogenetic analysis revealed that GME3638 and GME3634 are a pair of orthologues, and are grouped together with terpene synthases that synthesise cadinenes and related sesquiterpenes. (+)-Torreyol and α-cadinol were tested against a panel of human cancer cell lines and the latter was found to exhibit selective potent cytotoxicity in breast adenocarcinoma cells (MCF7) with IC50 value of 3.5 ± 0.58 μg/ml while α-cadinol is less active (IC50 = 18.0 ± 3.27 μg/ml). Conclusions This demonstrates that yeast-based genome mining, guided by transcriptomics, is a promising approach for uncovering bioactive compounds from medicinal mushrooms. Electronic supplementary material The online version of this article (doi:10.1186/s12934-017-0713-x) contains supplementary material, which is available to authorized users.

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.

Atmospheric ozonolysis of sesquiterpenes is an important source of secondary organic aerosols (SOA). The mechanisms by which Criegee Intermediates (CIs) react to form SOA precursors and the influence of environmental conditions, however, remain unclear. On the basis of environmental chamber experiments coupled with detailed characterization of gas-phase and particle-phase products, we present evidence that a significant fraction of CIs from ozonolysis of α-cedrene are stabilized and bimolecular reactions of these stabilized CIs (SCIs) play a key role in the formation of SOA precursors. Ozonolysis experiments were conducted in a 4.5 m3 collapsible fluoropolymer chamber under various conditions in the presence of the OH radical and SCI scavengers. The size and mass of SOA particles produced during ozonolysis were measured directly and used for calculation of particle effective density and mass yield. Gaseous and particulate products were analyzed by several mass spectrometry methods. A total of 14 compounds in gas phase and 17 compounds in particle phase were tentatively identified. The major gas-phase products are secondary ozonides (SOZ) from intramolecular reactions of SCIs. Multifunctional organic acids are dominant particle-phase products. The measured density of aerosol particles is 1.04 ± 0.03 to 1.38 ± 0.03 g/cm3, and the aerosol mass yield is (23.7 ± 0.4)% to (46.4 ± 6.5)%, depending on reaction conditions. The presence of acetic acid, an SCI scavenger, inhibits new particle formation, but leads to increased aerosol mass yield. In contrast, the addition of SO2 dramatically enhances new particle formation and total aerosol yield. The calculated OH formation yield decreases from (62.4 ± 4.9)% to (9.0 ± 1.6)% upon addition of SCI scavengers CH3COOH and SO2, indicating that a large fraction of excited CIs are collisionally stabilized and unimolecular decomposition of SCIs via the hydroperoxide channel can be suppressed by bimolecular reactions. The reaction of SCIs with SO2 leads to the formation of sulfuric acid, an important nucleation precursor. From the consumption of SO2 added as SCI scavenger, a lower-limit yield of SCIs from α-cedrene ozonolysis is estimated at ∼88%. Our work underscores the key role of SCIs in SOA formation and observed composition of gas- and particle-phase products from α-cedrene ozonolysis. Bimolecular reactions of sesquiterpene CIs with atmospherically relevant species (e.g. SO2, H2O) need to be considered when assessing the atmospheric relevance of ozonolysis of sesquiterpenes.

α-Cedrene is a pharmacologically active ingredient isolated from the essential oil of cedar. A selective and sensitive GC-MS/MS method was developed for the quantification of α-cedrene in rat plasma for the first time. α-Cedrene was extracted from rat plasma using ethyl acetate at neutral pH. The analytes were determined in selective reaction monitoring mode using MS/MS: m/z 204.3→119.0 for α-cedrene and m/z 146.0→111.0 for 1,4-dichlorobenzene (internal standard). The standard curve was linear (r(2) ≥ 0.995) over the concentration ranges of 5-800 ng/mL. The lower limit of quantification was 5 ng/mL using 50 μL of rat plasma. The coefficient of variation and relative error for intra- and interassays at four quality control levels were 3.1-13.9% and -4.0-2.6%, respectively. The stability of processing (freeze-thaw, long-term storage at -80°C, and short-term storage at room temperature) and chromatography (reinjection) was shown to be of insignificant effect. The present method was applied successfully to the pharmacokinetic study of α-cedrene after its intravenous (10 mg/kg) and oral (25 mg/kg) administration in male Sprague-Dawley rats.

In this work the first systematic study on the composition and the antibacterial properties of the extracts from the stems and the leaves of Ginja cherry are reported. This native Portuguese cherry ( Prunus cerasus , L. Rosaceae) is used to make a liquor (Ginjinha); both stems and leaves are a by-product of this process. The extracts from stems and leaves were prepared using different solvents (ethyl acetate, ethanol, acetone and water); their analysis was performed with GC–MS. Thirty-six volatile compounds were identified; terpenes – both hydrocarbons and oxygenated – were the main class of compounds. The extracts made from the stems with ethyl acetate were particularly rich in these species; compounds such as linalool, α-pinene, 4-terpineol and cedrene were present in concentration more than 10 times higher than in the other extracts. The antibacterial properties of all the extracts were tested against eight bacterial strains; the values of the minimum inhibitory concentration and minimum bactericidal concentration were determined. The stem extracts in ethyl acetate were the most active, showing bacteriostatic and bactericidal activity towards Gram-positive and Gram-negative microorganisms. This study showed that these by-products can be successfully valorized with solvent extraction of valuable compounds. The antibacterial properties of these extracts, combined with their antioxidant activity, make them suitable to be employed in areas like cosmetics and food packaging.

PurposeThe cowpea plant, being affordable and protein‐rich, is considered poor man's meat. The aim of this paper is to undertake a detailed investigation regardingin vitrototal antioxidant capacity (TAC) and chemical constituents of the vegetable oils from seeds of this plant, taking its nutritional value into consideration.Design/methodology/approachVegetable oils of different indigenous cowpea varieties were obtained using soxhelt extraction assembly and subjected to GC‐MS analyses and various antioxidant assays including 2,2′‐azinobis(3‐ethylbenzothiazoline‐6‐sulpohonic acid) (ABTS) radical cation scavenging, ferr, 2.2′‐diphenyl‐1‐picrylhydrazil (DPPH) radical scavenging, total phenolic contents (TPC), lipid peroxidation inhibition, and iron chelation activity.FindingsVarious chemical constituents including different hydrocarbons, tocopherols, ketones, fatty esters, estragole and cedrene were identified. TPCs were found to be 5.439, 5.7279, 7.6126, 6.7573 and 10.0591 mg/L gallic acid equivalent for S.A. Dandy, Elite, White Star, CP‐386 and FBD Rawan varieties, respectively. Employing ABTS radical decoloration assay a significant linear correlation (R2=0.997, 0.996, 0.997, 0.996 and 0.997 for S.A. Dandy, Elite, White Star, CP‐386 and FBD Rawan varieties, respectively) was found between the percent inhibition of ABTS radical cation and the amount of vegetable oils. The percent inhibition of the Fe(II)‐Ferrozine complex formation was found to be 29.45, 53.76, 82.91, 86.59 and 57.87 for the same varieties, respectively.Originality/valueGC‐MS and standardin vitroantioxidative capacity analyses data clearly demonstrated the potency of the cowpea as antioxidant and radical scavenger plant which may be used as a good source of natural antioxidants. The plant seeds may prove a better and cost‐effective substitute of expensive food items.

Fragrance is one of the most important and valued quality characters in sorghum and other foods and attracts a premium price in local and global trade. The allele of the SbBADH2 gene in fragrant sorghum cultivar E228 was characterized. A 1441 bp deletion extending from exon 13 to 15 was found rather than a deletion from exon 12 to 15 as had been reported earlier. This allowed the development and validation of a new perfect PCR-based marker for identification of fragrant sorghum accessions in breeding. The concentration of 2-acetyl-1-pyrroline (2AP) in the grain of this cultivar was estimated to be 6.5 ± 0.4 ppb using headspace solid-phase microextraction (HS-SPME) coupled with GC-MS. Flavor components of fragrant sorghum accession E228 (IC 568489) were analyzed and compared with the non-fragrant M35-1 cultivar. PCA analysis revealed that 2AP, benzothiazole, 2,3,5-trimethylpyridine, (1E)-1-ethylidene-1H-indene, cedrene, 2,4-bis(2-methyl-2-propanyl)phenol, 2-hexyl-1-octanol, and 2-butyl-1-octanol were among 25 compounds that were found in sorghum grain that may be contributing toward the aroma of fragrant sorghum. Proline and methylglyoxal contents were found to be higher in E228 than in M35-1, while SbBADH2 expression in E228 was half that in M35-1, suggesting a similar 2AP biosynthetic mechanism to that found in fragrant rice and soybean.

The essential oil from Filifolium sibiricum (L.) Kitam were extracted using hydrodistillation and GC-MS was used to analyse the essential oil. The main components were espatulenol (8.55%), geranyl acetate (8.03%), caryophyllene oxide (5.47%), calamenene (4.79%), geraniol (4.28%), calamenene (4.53%), geraniol (4.06%), cedrene epoxide (3.23%), myrtenol (3.18%), transgeranylgeranio (3.13%), etc. The essential oil showed intensive inhibitory effects against MCF-7 with IC50 level of 0.78 mg/mL, HepG-2 with IC50 level of 0.44 mg/mL, SKOV-3 with IC50 level of 0.27 mg/mL, BGC-823 with IC50 level of 0.34 mg/mL. In the antibacterial test, the essential oil showed the significant antibacterial activities. The MIC and MBC values were 5.20 and 5.20 mg/mL against Staphylococcus aureus.

Efficient syntheses of α-cedrene (1), α-pipitzol (2), and sec-cedrenol (3) were carried out using a new method, which was inspired by the proposed biosynthesis of the tricyclic skeleton of cedrol (12). The key transformation begins with the oxidative dearomatization of curcuphenol (5a) followed by an intramolecular [5 + 2] cycloaddition of the respective phenoxonium intermediate across the tethered olefin. The benzylic stereocenter effectively guides the formation of the first two stereocenters during the [5 + 2] reaction. The cascade then terminates with the selective incorporation of acetic acid to generate a third stereocenter, setting it apart from other previous cationic [5 + 2] reactions. The phenolic precursors (5a-h) are constructed from readily available salicylaldehydes, either as the racemate (one pot) or as a specific enantiomer (four pots) by a modification to our method for the generation of ortho-quinone methides (o-QMs).

哺乳動物はフェロモンのような特異的な化学シグナルや代謝中間体など、様々な化学物質を環境中に放出する。哺乳動物の化学コミュニケーションに関する最近の研究成果を紹介した。内容は、1)マウスの老臭と加齢ホルモンの正体ならびにその作用、2)ラットの思春期に現れるフェロモンの正体と異性に対する誘因作用、3)主要組織適合性抗原複合体(MHC)の突然変異とその揮発性シグナルの変化、4)化学シグナルに対する食物など外因性化合物摂取の影響、である。

The composition and the antibacterial activity of the essential oil, isolated by hydrodistillation from the wood burl parts of Tetraclinis articulata from Morocco, were analyzed by GC and GC/MS. Fifteen compounds accounting for about 96% of the oil were positively identified. Cedrene (23%), thymol (22%), 3-tert-butyl-4-methoxyphenol (19%), cedrenol (9.6%), muurolene (5.4%), and sclarene (3%) were found to be the main constituents. The essential oil was tested for antimicrobial activity against four different genera of bacteria: Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae and Streptococcus D. and exhibited considerable inhibitory effects against all bacteria tested with MIC and MIB close to 1.25 μl/mL. The findings of the present study suggest that Tetraclinis articulata oil from hydro-distillation of sawdust from burl wood collected from artisans, has a potential to be used as bactericide.

The effects of the ratio of the electric field strength to the buffer gas number density ( E / N ) in the drift tubeof a proton transfer reaction mass spectrometer on the product ion distributions of the sesquiterpenes -caryophyllene, -humulene, -cedreneandlongifolenehavebeeninvestigated.Chemicalionizationofthesesquiterpenes resulted in important fragmentation of the nascent excited ion/molecule complex at thehighest E / N values. The most important fragment ions were common to all sesquiterpenes and thereforecannot be used as fingerprints for specific isomers. The yield of the protonated molecule increased onaverage by a factor 1.6 by decreasing E / N from 140 to 80 Td. Taking into account the influence of E / N onthe reaction time and on the reactant ion mobility, it is estimated that this decrease in E / N may lead toan overall increase in the PTR-MS detection sensitivity of sesquiterpenes (based on the ion signal at m / z 205) by a factor 3.5.Product ion distributions of -cedrene and longifolene have also been determined atdifferent water vapour pressures. No substantial influence of the water vapour pressure on the production yields was observed, which is an advantage when quantifying sesquiterpenes by PTR-MS in samplesof varying relative humidity.© 2008 Elsevier B.V. All rights reserved.

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 cedrene carbon skeleton was directly and efficiently assembled from a simple monocyclic precursor by the strategic use of a high yielding intramolecular Pauson–Khand cyclisation reaction. A small number of further synthetic manipulations provided a concise formal total synthesis of α- and β-cedrene. The cyclisation precursor was readily prepared, with a stereoselective ketone alkenylation selectively providing the olefin required for efficient access to the natural target.

Wender and Howbert's remarkable synthesis of alpha-cedrene in 1981 brought the attention of the synthetic community to the alkene-arene meta-photocycloaddition reaction. Here we review the natural product syntheses that have been achieved, over the last 25 years, utilising this strategic level reaction.

The gas-phase reaction of ozone with α-cedrene ( I ) in the absence and presence of an OH radical scavenger (cyclohexane) has been studied in the outdoor 25 m 3 Teflon film chambers at the UNC smog chamber facility. Twenty-two compounds were identified for the first time in this study. Important products identified and semi-quantified were α-cedronaldehyde ( VI ), α-cedronic acid ( VIII ), α-cedrinic acid ( X ), α-norcedronaldehyde ( VII ), 8-hydroxy-9-α-cedranone ( III ), and α-norcedronic acid ( IX ). Acetone, formaldehyde, and acetaldehyde also were identified in this study. On average, measured gas and particle phase products accounted for ∼56% of the reacted α-cedrene. The total yield of products bearing hydroxy groups (e.g. 8-hydroxy-9-α-cedranone ( III )) and aldehydes (e.g. α-cedronaldehyde ( VI ), α-norcedronaldehyde ( VII )) was found to be slightly dependent on the presence of an OH radical scavenger. Generally, the aldehyde yield was found to be higher when cyclohexane was present, and the hydroxy compounds yield was higher when cyclohexane was absent. All products identified in this study were found in the particle phase. α-Cedrinic acid ( X ), α-cedronic acid ( VIII ), and α-cedronaldehyde (VI) were observed in the early stage in the aerosol phase and may play an important role in the early formation of SOA. Detailed reaction schemes leading to most reaction products observed here are presented and discussed.

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.

The terpenoid composition of three fossil resins from macrofossils of Cretaceous and Tertiary conifers has been analyzed by gas chromatography–mass spectrometry (GC–MS). The mono-, sesqui- and diterpenoids which have been identified in the resin extracts are derived from precursors produced by the respective source plants and may be used as chemosystematic markers when compared with terpenoids in extant conifers. Sesquiterpenoids (cedrene, cuparene, cadinanes) and phenolic diterpenoids (ferruginol and derivatives) are the major components in Cupressospermum saxonicum Mai (Miocene). The terpenoid characteristics strongly support a relationship to the Cupressaceae s. str. The resin of Doliostrobus taxiformis (Sternberg) Kvacek (Eocene) consists of abietane and pimarane type resin acids accompanied by minor amounts of phenolic diterpenoids (ferruginol, hinokiol). According to morphological and anatomical characteristics, D. taxiformis was previously compared to both, extant Araucariaceae and Cupressaceae s.l., but the terpenoid pattern of the resin now supports a relationship to the Cupressaceae s.l. rather than to Araucariaceae. Degraded diterpenoids of the abietane type are the major compounds in the extract of Tritaenia linkii (Roemer) Magdefrau et Rudolf (Lower Cretaceous) indicating considerable oxidative alteration of the resin. Since the terpenoids in the resin of T. linkii are highly degraded or belong to the common abietane class, the leaves cannot be assigned or compared to any modern family based on their terpenoid composition. The presence of ferruginol probably excludes pinaceous affinities. Terpenoids proved to be valuable chemosystematic markers for fossil conifers once they are adequately preserved. The analysis of resin extracts by GC–MS is a suitable tool for the investigation of soluble compounds in fossil plants.

Basil (O. gratissimum L) is a aromatic and medicinal plant widely used in traditional medicine in Morocco. The aim of this work was to study the effect of three plant growth regulators gibberellic acid (GA), indole 3-acetic acid (IAA) and benzylaminopurine (BAP) on the content and composition of essential oils of this plant, especially on the main compound (methyl chavicol) and its isomer (the trans-anethole). The results showed a wide variation on yield, content and range of the molecule constituent of oil, with a balance of appearances and/or disappearances of a few molecules. GA caused a slight decrease in the oil yield (0.2%), but it increased the diversity of compounds (17 molecules) with the appearance of four new compounds (naphthalene, camphor, germacrene-D, and ledene) and disappearance of (β cedrene, azulene). This variation also caused a very important decrease in the main compound (methyl chavicol) and increases its isomer (trans-anethole). IAA and BAP caused an increase in the yield of essential oil (0.30% and 0.32% respectively) without much influence on the main compounds, but with some change in the composition such as the appearance of (germacrene-D) and the disappearance of (aristolene).

(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.

Tandem free radical cycloaddition reaction of the N-Aziridinylimine intermediate produced tricyclo[5.3.1.0 1,5 ]undecane skeleton stereoselectively. A total synthesis of α-cedrene was completed in three step sequence from the cyclization product.