Chemical Variability of the Berry Essential Oil of Two Subspecies of Juniperus Oxycedrus L. from Northwestern Algeria.

The chemical composition of 33 oil samples isolated from the berries of individual trees of two subspecies of Juniperus oxycedrus L., collected in four locations in Tlemcen and Aïn Temouchent provinces, was investigated by GC-FID, GC/MS and 13CNMR. In total, 83 compounds were identified, accounting for 85.9 % to 98.6 % of the total composition. Yields ranged between 0.02 and 0.40 % (w/w). All compositions were submitted to statistical analysis. Combination of hierarchical clustering dendrogram and principal component analysis suggested the existence of two groups, the second group being sub-divided into two sub-groups. Groups and sub-groups were distinguished with respect to their contents of α-pinene, germacrene D, myrcene and, to a lesser extent, of manoyl oxide. The chemical composition of the oils belonging to subsp. oxycedrus was largely dominated by monoterpenes. α-Pinene (23.7-63.2 %) and germacrene D (4.5-25.4 %) were the major components, followed by myrcene (3.1-16.7 %). Conversely, samples oils of subsp. macrocarpa were largely dominated by germacrene D (4.4-30.0 %), followed by a lower content of α-pinene (10.0-24.3 %) and myrcene (1.0-4.3 %) and a significant content of manoyl oxide (4.3-9.9 %).

Chemical Variability and Anti-Inflammatory Activity of Rosmarinus officinalis L. Leaf Essential Oil from Algerian Sahara.

The chemical composition of 71 oil samples from the leaves of Rosmarinus officinalis L., harvested in three provinces: Naâma (Western Algeria), Béchar and Adrar (Algerian Sahara), was investigated by GC-FID, GC/MS and 13CNMR. In total, 52 compounds were identified accounting for 88.8 % to 99.9 % of the total composition. The chemical composition of the oils was largely dominated by monoterpenes, with 1,8-cineole (9.7-70.2 %), camphor (0.3-31.0 %) being the major compounds followed by borneol (0.3-21.0 %), α-pinene (4.5-14.5 %), ß-pinene (0.1-12.0 %), linalool (0.7-9.9 %) and verbenone (up to 11.1 %) which was present only in the samples harvested in Adrar. All compositions (71 samples) were submitted to statistical analysis. Combination of hierarchical clustering dendrogram and principal component analysis suggested the existence of three groups (one of these being subdivided into two sub-groups) which were distinguished on the basis of 1,8-cineole, camphor and verbenone contents. Four essential oil samples, containing 1,8-cineole and/or camphor as main components, exhibited anti-inflammatory activity against lipoxygenase, with IC50 values in the range 93 to 155 µg/mL.

Composition and Chemical Variability of the Essential Oil from Aerial Parts of Cladanthus scariosus, an Endemic Species to the Moroccan High Atlas.

Cladanthus scariosus (Ball) Oberpr. & Vogt is endemic to Moroccan High Atlas. It is known under the vernacular names Irezghi or Irezgui. Three essential oil samples have been isolated from aerial parts and analyzed by combination of chromatographic and spectroscopic techniques [gas chromatography (GC) in combination with retention indices (RI), gas chromatography-mass spectrometry (GC/MS) and 13 C-NMR spectroscopy]. The compositions of oil samples were dominated by monoterpenes: α-pinene sabinene, and terpinen-4-ol. Chamazulene and dihydrochamazulene isomers as well as various hemiterpene esters and analogs have been identified. To evidence a chemical variability, statistical analysis performed on 13 oil sample compositions allowed partitioning into three groups, mainly differentiated by their contents of sabinene, camphor, borneol, terpinen-4-ol, and germacrene D.

Neuropeltis acuminata (P. Beauv.): Investigation of the Chemical Variability and In Vitro Anti-inflammatory Activity of the Leaf Essential Oil from the Ivorian Species.

The variability of chemical composition of the leaf essential oil (EO) from Neuropeltis acuminata, a climbing liana growing wild in Ivory Coast, was investigated for the first time. The in vitro anti-inflammatory activity was also evaluated. Thirty oil samples were isolated from leaves collected in three forests of the country and analyzed using a combination of Column Chromatography (CC), Gas Chromatography with Retention Indices (GC(FID)), Gas Chromatography-Mass Spectrometry (GC-MS), and 13Carbon-Nuclear Magnetic Resonance (13C-NMR). Fractionation by CC led to the first-time isolation from natural source of δ-cadinen-11-ol, whose structural elucidation by one dimension (1D) and 2D-NMR spectroscopy is reported here. Finally, 103 constituents accounting for 95.7 to 99.6% of the samples' compositions were identified. As significant variations of the major constituents were observed, the 30 oil compositions were submitted to hierarchical cluster and principal components analyses. Five distinct groups were evidenced: Group I, dominated by (E)-ß-caryophyllene, kessane, and δ-cadinene, while the main constituents of Group II were germacrene B, ledol, α-humulene, (E)-γ-bisabolen-12-ol, and γ-elemene. Group III exhibited guaiol, germacrene D, atractylone, (E)-γ-bisabolen-12-ol, δ-cadinene and bulnesol as main compounds. Group IV was dominated by (E)-nerolidol, guaiol, selina-4(15),7(11)-diene and bulnesol, whereas (E)-ß-caryophyllene, α-humulene and α-muurolene were the prevalent compounds of Group V. As the harvest took place in the same dry season in the three forests, the observed chemical variability could be related to harvest sites, which includes climatic and pedologic factors, although genetic factors could not be excluded. The leaf oil sample S24 behaved as a high inhibitor of LipOXygenase (LOX) activity (half maximum Inhibitory Concentration, IC50: 0.059 ± 0.001 mg mL-1), suggesting an anti-inflammatory potential.

13C NMR Dereplication Using MixONat Software: A Practical Guide to Decipher Natural Products Mixtures.

The growing use of herbal medicines worldwide requires ensuring their quality, safety, and efficiency to consumers and patients. Quality controls of vegetal extracts are usually undertaken according to pharmacopeial monographs. Analyses may range from simple chemical experiments to more sophisticated but more accurate methods. Nowadays, metabolomic analyses allow a fast characterization of complex mixtures. In the field, besides mass spectrometry (MS), nuclear magnetic resonance spectroscopy (NMR) has gained importance in the direct identification of natural products in complex herbal extracts. For a decade, automated dereplication processes based on 13C-NMR have been emerging to efficiently identify known major compounds in mixtures. Though less sensitive than MS, 13C-NMR has the advantage of being appropriate to discriminate stereoisomers. Since NMR spectrometers nowadays provide useful datasets in a reasonable time frame, we have recently made available MixONat, a software that processes 13C as well as distortionless enhancement by polarization transfer (DEPT)-135 and -90 data, allowing carbon multiplicity (i.e., CH3, CH2, CH, and C) filtering as a critical step. MixONat requires experimental or predicted chemical shifts (δ C) databases and displays interactive results that can be refined based on the user's phytochemical knowledge. The present article provides step-by-step instructions to use MixONat starting from database creation with freely available and/or marketed δ C datasets. Then, for training purposes, the reader is led through a 30 - 60 min procedure consisting of the 13C-NMR based dereplication of a peppermint essential oil.

Chemical Variability of Moroccan Myrtle Oil.

Thirty-three oil samples isolated from aerial parts of Myrtus communis L. harvested in seven localities, from Northern to Central Morocco, have been analyzed by combination of chromatographic and spectroscopic techniques. The 33 compositions have been subjected to statistical analysis, hierarchical cluster analysis (HCA) and principal component analysis (PCA). Two groups have been differentiated on the basis of their myrtenyl acetate and α-pinene contents and each one was sub-divided in two sub-groups according to the contents of 1,8-cineole and linalool. The compositions of our 33 myrtle oil samples may be named as follow by their main components: sub-group IA (13/33): α-pinene/1,8-cineole/linalool; sub-group IB (6/33): 1,8-cineole/α-pinene; sub-group IIA (10/33): 1,8-cineole/myrtenyl acetate; sub-group IIB (4/33): myrtenyl acetate.

Chemical Variability and In Vitro Anti-Inflammatory Activity of Leaf Essential Oil from Ivorian Isolona dewevrei (De Wild. & T. Durand) Engl. & Diels.

The chemical variability and the in vitro anti-inflammatory activity of the leaf essential oil from Ivorian Isolona dewevrei were investigated for the first time. Forty-seven oil samples were analyzed using a combination of CC, GC(RI), GC-MS and 13C-NMR, thus leading to the identification of 113 constituents (90.8-98.9%). As the main components varied drastically from sample to sample, the 47 oil compositions were submitted to hierarchical cluster and principal components analyses. Three distinct groups, each divided into two subgroups, were evidenced. Subgroup I-A was dominated by (Z)-ß-ocimene, ß-eudesmol, germacrene D and (E)-ß-ocimene, while (10ßH)-1ß,8ß-oxido-cadina-4-ene, santalenone, trans-α-bergamotene and trans-ß-bergamotene were the main compounds of Subgroup I-B. The prevalent constituents of Subgroup II-A were germacrene B, (E)-ß-caryophyllene, (5αH,10ßMe)-6,12-oxido-elema-1,3,6,11(12)-tetraene and γ-elemene. Subgroup II-B displayed germacrene B, germacrene D and (Z)-ß-ocimene as the majority compounds. Germacrene D was the most abundant constituent of Group III, followed in Subgroup III-A by (E)-ß-caryophyllene, (10ßH)-1ß,8ß-oxido-cadina-4-ene, germacrene D-8-one, and then in Subgroup III-B by (Z)-ß-ocimene and (E)-ß-ocimene. The observed qualitative and quantitative chemical variability was probably due to combined factors, mostly phenology and season, then harvest site to a lesser extent. The lipoxygenase inhibition by a leaf oil sample was also evaluated. The oil IC50 (0.020 ± 0.005 mg/mL) was slightly higher than the non-competitive lipoxygenase inhibitor NDGA IC50 (0.013 ± 0.003 mg/mL), suggesting a significant in vitro anti-inflammatory potential.

Composition, Chemical Variability and Biological Activity of Cymbopogon schoenanthus Essential Oil from Central Algeria.

Cymbopogon schoenanthus (L.) Spreng. (Poaceae) is an aromatic plant whose aerial parts and rhizome produced an essential oil with pleasant odor. A chemical variability has been observed depending of the countries where the plant grows wild, including Algeria. The chemical compositions of 24 oil samples isolated from plants harvested in Central Algeria have been investigated, to evidence homogeneity or chemical variability within a given area of harvest. Twenty of these were dominated by cis- and trans-p-menth-2-en-1-ols (22.6 %±3.6 and 14.3 %±1.7, resp.) beside four atypical compositions. Otherwise, aerial parts and rhizomes produced similar essential oils. Lastly, a fair antimicrobial activity was measured against Staphylococcus aureus strain, while the antioxidant potential was low.

Composition and Intraspecific Chemical Variability of Leaf Essential Oil of Laggera pterodonta from Côte d'Ivoire.

The chemical composition of 44 leaf oil samples of Laggera pterodonta (DC.) Sch.Bip. ex Oliv. (Asteraceae) from Côte d'Ivoire was investigated, using combination of chromatographic (GC-FID) and spectroscopic (GC/MS, 13 C-NMR) techniques. Two oil samples chosen according to their chromatographic profiles were submitted to column chromatography and all fractions of CC were analyzed by GC-FID, GC/MS and 13 C-NMR. In total, 83 components accounting for 96.5 to 99.4 % of the whole chemical composition were identified. Significant variations were observed within terpene classes: monoterpene hydrocarbons (0.4-22.7 %), oxygenated monoterpenes (32.9-54.9 %), sesquiterpene hydrocarbons (18.6-38.3 %) and oxygenated sesquiterpenes (3.5-38.4 %). Thus, the 44 compositions were subjected to hierarchical cluster analysis (HCA) and principal component analysis (PCA). Two groups were differentiated according to their composition. All the samples contained 2,5-dimethoxy-p-cymene, α-humulene and (E)-ß-caryophyllene among the main components. Other components were present at appreciable contents and allowed differentiation of two groups: sabinene and germacrene D for Group I; 10-epi-γ-eudesmol and eudesm-7(11)-en-4α-ol for Group II. All the samples collected in Eastern Côte d'Ivoire constituted Group I, while samples collected in the Central area of the country constituted Group II.

New Natural Oxygenated Sesquiterpenes and Chemical Composition of Leaf Essential Oil from Ivoirian Isolona dewevrei (De Wild. & T. Durand) Engl. & Diels.

This study aimed to investigate the chemical composition of the leaf essential oil from Ivoirian Isolona dewevrei. A combination of chromatographic and spectroscopic techniques (GC(RI), GC-MS and 13C-NMR) was used to analyze two oil samples (S1 and S2). Detailed analysis by repetitive column chromatography (CC) of essential oil sample S2 was performed, leading to the isolation of four compounds. Their structures were elucidated by QTOF-MS, 1D and 2D-NMR as (10ßH)-1ß,8ß-oxido-cadin-4-ene (38), 4-methylene-(7αH)-germacra-1(10),5-dien-8ß-ol (cis-germacrene D-8-ol) (52), 4-methylene-(7αH)-germacra-1(10),5-dien-8α-ol (trans-germacrene D-8-ol) (53) and cadina-1(10),4-dien-8ß-ol (56). Compounds 38, 52 and 53 are new, whereas NMR data of 56 are reported for the first time. Lastly, 57 constituents accounting for 95.5% (S1) and 97.1% (S2) of the whole compositions were identified. Samples S1 and S2 were dominated by germacrene D (23.6 and 20.5%, respectively), followed by germacrene D-8-one (8.9 and 8.7%), (10ßH)-1ß,8ß-oxido-cadin-4-ene (7.3 and 8.7), 4-methylene-(7αH)-germacra-1(10),5-dien-8ß-ol (7.8 and 7.4%) and cadina-1(10),4-dien-8ß-ol (7.6 and 7.2%). Leaves from I. dewevrei produced sesquiterpene-rich essential oil with an original chemical composition, involving various compounds reported for the first time among the main components. Integrated analysis by GC(RI), GC-MS and 13C-NMR appeared fruitful for the knowledge of such a complex essential oil.

Composition, Seasonal Variation, and Biological Activities of Lantana camara Essential Oils from Côte d'Ivoire.

This work aims to study the variations in the composition of Lantana camara leaf, flower, and stem essential oils over two years. L. camara organs were harvested in Bregbo (East Côte d'Ivoire) each month from June 2015 to June 2017. The essential oils were obtained by hydrodistillation and characterized by GC-MS and 13C NMR. Eighty-four compounds accounting for 84.4-99.1% of the essential oils have been identified. The essential oils hydrodistillated from L. camara are dominated by sesquiterpenes such as (E)-ß-caryophyllene and α-humulene, which were found in all samples. Some monoterpenes such as thymol, sabinene, and α-pinene were also present. Statistical analysis (principal component analysis and clustering) revealed a high variability in essential oil composition between the different organs and also within the studied periods, as the thymol proportion was higher during flowering and fruiting months. In addition, the stem, flower, and fruit essential oils were more concentrated in thymol than the leaf essential oils. The proportions of (E)-ß-caryophyllene and α-humulene were strictly inverted with the thymol proportion throughout the harvest period or vegetative cycle. The antioxidant, anti-inflammatory and insecticidal activities of leaves and flowers essential oils were also studied. Results showed that L. camara leaf and flower essential oils displayed high antioxidant, anti-inflammatory and insecticidal activities.

Identification and Quantitative Determination of Resin Acids from Corsican Pinus pinaster Aiton Oleoresin Using 13 C-NMR Spectroscopy.

Twenty-three resin samples have been obtained by tapping from individual Pinus pinaster adult trees grown in Corsica and submitted to acido-basic partition. Identification and quantitative determination of resin acids has been carried out using 13 C-NMR spectroscopy following a method developed by our group. The main components were dehydroabietic acid (up to 37.6 %), levopimaric acid (up to 35.5 %) and abietic acid (up to 24.7 %). A lignan, pinoresinol, has been identified in some samples. Within the 23 compositions, submitted to k-means analysis and Principal Component Analysis, two clusters have been perfectly differentiated, whose compositions were dominated by dehydroabietic acid (Group I, M=23.5 %, SD=6.3) and levopimaric acid (Group II, M=21.2 %; SD=6.2), respectively. Both compositions have been observed in the three locations of harvest.

Biological Activities and Chemical Composition of Santolina africana Jord. et Fourr. Aerial Part Essential Oil from Algeria: Occurrence of Polyacetylene Derivatives.

The chemical composition of 18 oil samples of Santolina africana isolated from aerial parts at full flowering, collected in three locations in eastern Algeria was determined by GC(RI), GC/MS and 13C-NMR analysis. The major components were: germacrene D, myrcene, spathulenol, α-bisabolol, ß-pinene, 1,8-cineole, cis-chrysanthenol, capillene, santolina alcohol, camphor, terpinen-4-ol and lyratol. The chemical composition appeared homogeneous and characterized by the occurrence of four derivatives which exhibited a conjugated alkene dialkyne moiety. They were identified for the first time in an essential oil from S. africana. The collective oil sample exhibited moderate antimicrobial and antioxidant activities whereas the anti-inflammatory activity presented a real potential. IC50 value of Santolina africana essential oil (0.065 ± 0.004 mg/mL) is 5-fold higher than IC50 value of NDGA used as positive control.

Halogenated C15 Acetogenin Analogues of Obtusallene III from a Laurenciella sp. Collected in Corsica.

NMR chemical profiling of a Laurenciella sp. using a computerized method developed in our laboratory resulted in the identification of five new compounds (1-5) and 17 known compounds, among which 3-(E)-laurenyne represented by far the most abundant metabolite. Compounds 1 to 5 were isolated and fully characterized by detailed spectroscopic analysis. The absolute configuration and structural features of compound 1 were determined by single-crystal X-ray diffraction analysis. Compounds 1 to 4 are 12-membered cyclic ether acetogenins that are present in solution as interconverting conformers exhibiting an (aR) configuration of the bromoallene unit together with an S configuration at C-4. Among these, compound 3 is the first obtusallene derivative with bromine substituents at both the C-7 and C-12 positions. Compound 5 is an acetogenin bearing a [5.5.1]bicyclotridecane ring system. A plausible biosynthetic route to 1-4 is proposed.

Composition and Chemical Variability of Enantia polycarpa Engl. & Diels Leaf Essential Oil from Côte d'Ivoire.

The composition of Enantia polycarpa Engl. & Diels leaf essential oil has been investigated for the first time using a combination of chromatographic and spectroscopic techniques. The compositions of 52 leaf essential oil samples have been subjected to statistical analysis, hierarchical cluster analysis (HCA) and principal component analysis (PCA). Four groups were differentiated, of which the compositions were dominated by ß-elemene and germacrene B (Group III, 22/52 samples); germacrene D (Group I, 16/52 samples); ß-cubebene (Group IV, 8/52 samples) and by germacrene B and germacrene D (Group II, 6/52 samples). A special attention was brought to the quantification of the thermolabile components, germacrene A, germacrene B and germacrene C, as well as that of their rearranged compounds, ß-elemene, γ-elemene and δ-elemene. 13 C-NMR data of ß-cubebene have been provided.

Chemical Variability of the Essential Oil of Pituranthos scoparius from Algeria.

The chemical composition of 93 oil samples from the aerial parts of Pituranthos scoparius, harvested in three regions of Algeria, was investigated by GC-FID, GC/MS and 13 C-NMR. Monoterpene hydrocarbons dominated in association with phenylpropanoids and a chemical variability was found highlighting three clusters. The composition of group I (36 samples) exhibited an atypical composition characterized by a very high contents of 6-methoxyelemicine (13.0 - 59.6%), followed by sabinene (1.1 - 43.0%) and limonene (6.6 - 39.0%), while the samples of group II (12 samples) contained a high content of limonene (9.2 - 44.0%), followed by myristicine (0.0 - 29.4%) and a lower amount of sabinene (0.8 - 2.3%). Group III (45 samples) could be divided in two subgroups. Subgroup SGIIIA was characterized by a very high content of sabinene (28.0 - 55.6%), followed by elemicine (0.0 - 29.1%), while the samples belonging to SGIIIB were characterized by the lower content of sabinene (6.2 - 35.5%) and a significant content of myristicine (1.5 - 32.4%), α-pinene (4.2 - 31.0%) and dill apiole (0.1 - 31.4%). Each harvested region was characterized by a different chemical composition.

New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica.

The chemical investigation of an ethyl acetate extract (EtOAc) obtained from Laurencia obtusa, collected in Corsica, allowed for the identification of three new compounds (1, 2, and 4) and six known compounds. Compounds 1 to 4 were isolated and fully characterized by a detailed spectroscopic analysis. Compounds 1 and 2 are two C15-acetogenins sharing the same ring system: a tetrahydropyran linked by a methylene to a tetrahydrofuran ring. Compound 1 exhibits a bromoallene unit whereas compound 2 possesses an uncommon α-bromo-α,ß-unsaturated aldehyde terminal unit. Compound 4 is the first diterpene exhibiting a 19(4 → 3)abeo-labdane skeleton isolated from a Laurencia species. Isolation of concinndiol (compound 3) together with compound 4 suggests a common biosynthetic origin. Additionally, five known compounds, namely sagonenyne, laurene, α-bromocuparene, microcladallene A, and ß-snyderol were identified in chromatographic fractions by NMR analysis using a computerized method that was developed in our laboratory.

Anti-Quorum Sensing Activity of 12 Essential Oils on chromobacterium violaceum and Specific Action of cis-cis-p-Menthenolide from Corsican Mentha suaveolens ssp. Insularis.

Quorum sensing (QS) is a bacterial communication mechanism used to express various survival or virulence traits leading to enhanced resistance. Chromobacterium violaceum is a commonly used strain that highlights anti-QS action of bioactive substances. Here, we wanted to see if 12 selected essential oils (EO) could exert anti-QS activity. We measured the sublethal minimal QS inhibitory concentration (MQSIC) by assessing violacein production of C. violaceum along with bacterial growth. To confirm the QS disruption, we also proceed to surface bacterial observations using scanning electron microscopy (SEM). We showed that cis-cis-p-menthenolide extracted and isolated from a plant endemic to occidental Mediterranean Sea islands, Mentha suaveolens ssp. insularis, acts as an inhibitor of violacein production and biofilm formation. Measured MQSIC was much lower than the minimal inhibitory concentration (MIC): 0.10 mg·mL-1 vs. 3.00 mg·mL-1. Moreover, disturbance of QS-related traits was confirmed by the degradation of C. violaceum biofilm matrix. There is a clear structure⁻activity relationship between cis-cis-p-menthenolide and anti-QS activity. Indeed, its isomer molecule (mintlactone) exerts a poor anti-QS action. These results indicate that inhibition of violacein production and biofilm formation by cis-cis-p-menthenolide might be related to a disruption in the QS mechanism.

Discrimination and Characterization of Two Mediterranean Species from the Laurencia Complex (Rhodomelacea) Using an NMR-Based Metabolomic Approach.

Generic and specific determination among the Laurencia complex is a challenging task. DNA barcoding combined with phenotypic investigations are mandatory for species differentiation. In this study, two morphologically different members of the Laurencia complex were investigated using untargeted 1 H-NMR-based metabolomics. Twenty-one population samples were collected in order to evaluate both temporal and geographical homogeneity. Data obtained from 1 H-NMR analysis followed by statistical analysis allowed a clear separation of all the samples into two groups. DNA mitochondrial tests confirmed this pattern and identified the two species as Laurenciella sp. and Laurencia obtusa. In addition, metabolites responsible of this discrimination were investigated directly in crude extracts by 13 C-NMR using an in-house computer-assisted method. The combination of both untargeted (1 H) and targeted (13 C) NMR-based metabolomic approaches proves to be a powerful and complementary approach to discriminate species from the Laurencia complex.

Chemical Variability of Ivoirian Xylopia rubescens Leaf Oil.

Forty-two essential oil samples were isolated from leaves of Xylopia rubescens harvested in three forests of Southern Ivory Coast. All the samples have been submitted to GC-FID and the retention indices (RIs) of individual components have been measured on two capillary columns of different polarity. In addition, 20 oil samples, selected on the basis of their chromatographic profile, were also analyzed by 13 C-NMR and 24 components (78.0 - 92.4% of the whole compositions) have been identified. The content of the main components varied drastically from sample to sample: furanoguaia-1,4-diene (5.7 - 54.1%), furanoguaia-1,3-diene (1.1 - 10.5%), (8Z,11Z,14Z)-heptadeca-8,11,14-trien-2-one (4.3 - 16.0%), and (E)-ß-caryophyllene (1.7 - 17.3%). Hierarchical cluster and principal components analysis of the 42 oil compositions allowed the distinction of two well-differentiated groups of unequal importance within the oil samples. Oil samples of the main group (Group II) contained mainly furanoguaia-1,4-diene (mean [M] = 43.1%; standard deviation [SD] = 3.2%) while furanoguaia-1,3-diene (M = 8.4%; SD = 0.9%) and (8Z,11Z,14Z)-heptadeca-8,11,14-trien-2-one (M = 7.1%; SD = 1.5%) were present at appreciable contents. The composition of Group I was dominated by furanoguaia-1,4-diene (M = 17.0%; SD = 8.5%), (8Z,11Z,14Z)-heptadeca-8,11,14-trien-2-one (M = 10.2%; SD = 2.4%) and (E)-ß-caryophyllene (M = 9.5%; SD = 5.3%).