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Article

Gymnosperms of Idaho: Chemical Compositions and Enantiomeric Distributions of Essential Oils of Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata

by
Kathy Swor
1,
Prabodh Satyal
2,
Ambika Poudel
2 and
William N. Setzer
2,3,*
1
Independent Researcher, 1432 W. Heartland Dr., Kuna, ID 83634, USA
2
Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA
3
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
*
Author to whom correspondence should be addressed.
Molecules 2023, 28(6), 2477; https://doi.org/10.3390/molecules28062477
Submission received: 8 February 2023 / Revised: 24 February 2023 / Accepted: 4 March 2023 / Published: 8 March 2023
(This article belongs to the Special Issue Essential Oils II)
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Abstract

:
Conifers are of great economic value in terms of lumber production, important for construction and other uses such as pulp and paper. They are also important sources of essential oils. Conifer species have been vital to the ethnobotany and traditional herbal medicine of many different Native American groups. The objective of this work was to obtain and analyze the essential oils of several conifer species (Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata) growing in Idaho. The foliar essential oils were obtained by hydrodistillation and then analyzed by gas chromatographic methods, including GC-MS, GC-FID, and chiral GC-MS. The essential oils were obtained in varying yields from 0.66% up to 4.70%. The essential oil compositions were largely dominated by monoterpene hydrocarbons and oxygenated monoterpenoids. The chiral monoterpenoids were generally rich in the (−)-enantiomers for members of the Pinaceae, but the (+)-enantiomers predominated in the Cupressaceae. The essential oil compositions obtained in this work are qualitatively similar, but quantitatively different, to previously reported compositions and confirm and complement the previous reports. However, this is the first comprehensive analysis of the chiral terpenoid components in these conifer species. Additional research on essential oils of the Pinaceae and Cupressaceae is needed to describe the chemical profiles, chemical compositions, and enantiomeric distributions more reliably in the various species and infraspecific taxa of these two families.

Graphical Abstract

1. Introduction

Idaho, and western North America in general, is home to great habitat diversity, including mountains, canyons, and Great Basin deserts, and is also home to a large number of conifer species. Many of these trees are important sources of timber and other forest products; they have been important in Native American cultures in traditional medicine, and in addition to wood and wood products, are sources of essential oils. As part of our ongoing investigation into the essential oils of Idaho, we have collected samples of Rocky Mountain subalpine fir (Abies lasiocarpa var. lasiocarpa) (Pinaceae), Engelmann spruce (Picea engelmannii subsp. engelmannii) (Pinaceae), Rocky Mountain lodgepole pine (Pinus contorta subsp. latifolia) (Pinaceae), Rocky Mountain Douglas fir (Pseudotsuga menziesii var. glauca) (Pinaceae), and western red cedar (Thuja plicata) (Cupressaceae) growing in Idaho. The foliar essential oils have been obtained by hydrodistillation and the essential oils analyzed by gas chromatographic (GC-MS and GC-FID) methods. The enantiomeric distributions of monoterpenoid components have also been examined using chiral GC-MS.
Abies lasiocarpa (Hook.) Nutt. (subalpine fir, Pinaceae) is native to the mountains of western North America (Figure 1) [1]. On young trees, the bark is smooth and gray with resin blisters, but appears rough and fissured on older trees. The leaves are flat needles, 1.5–3 cm long (Figure 2). The infraspecific taxonomy of A. lasiocarpa has been debated and three varieties have been suggested: Abies lasiocarpa (Hook.) Nutt. var. lasiocarpa (coastal subalpine fir, ranging from British Columbia south through the Cascade Mountains of Washington and Oregon); Abies lasiocarpa var. bifolia (A. Murray bis) Eckenw. (Rocky Mountain subalpine fir, ranging from British Columbia south through the Rocky Mountains of Idaho, Montana and Colorado); and Abies lasiocarpa var. arizonica (Merriam) Lemmon (corkbark fir, found in high mountains of Arizona and New Mexico) based on morphological and monoterpenoid profiles [2,3]. However, based on DNA data, there is little support for the recognition of A. l. var. bifolia as a distinct variety, but rather a chemotype of A. l. var. lasiocarpa due to geographical selection differences [2]. The foliar essential oil compositions of the three varieties have been investigated previously by Hunt and von Rudloff [4] and by Adams and co-authors [2]. The essential oil of coastal subalpine fir has been characterized by relatively high concentrations of β-phellandrene (36.8–58.8%), while Rocky Mountain subalpine fir essential oil is rich in camphene (7.3–16.2%) and bornyl acetate (13.0–31.6%) [4]. Corkbark fir also has high concentrations of camphene (15.2%) and bornyl acetate (34.4%) [2]. The Shoshoni people took an infusion of the needles of A. lasiocarpa to treat colds [5].
Picea engelmannii Engelm. (Engelmann spruce, Pinaceae) is widely distributed in western North America and ranges from British Columbia and Alberta, Canada, south through the Cascade Mountains of Washington and Oregon, and through the Rocky Mountains of Idaho, Montana, Wyoming, Colorado, and New Mexico, as well as Utah and Arizona (Figure 3) [7]. Two subspecies of P. engelmannii have been recognized [8], P. engelmannii subsp. engelmanii and Picea engelmannii subsp. mexicana (Martínex) P.A. Schmidt, which is found on the high mountains of northern Mexico [9]. The bark of P. engelmannii is thin and flaky; the needles are 15–30 mm long (Figure 4).
Pinus contorta Douglas ex Loudon subsp. latifolia (Engelm. ex S. Watson) Critchf. (Rocky Mountain lodgepole pine, Pinaceae) is found in the Rocky Mountains of western North America, from the Yukon, south through Colorado (Figure 5). There are two other subspecies of P. contorta, P. contorta subsp. contorta Douglas ex Loudon (the shore pine), which ranges along the Pacific coast from southern Alaska, south to northwestern California, and P. contorta subsp. murrayana (Balf.) Engelm. (the Sierra lodgepole pine), which ranges in the Cascade Range in Washington and Oregon, south into northern California and the Sierra Nevada Range (Figure 5) [10,11]. The gray-brown bark of P. contorta subsp. latifolia is thin and scaly, while the needles are 4–8 cm long and in pairs (Figure 6).
Pseudotsuga menziesii (Mirb.) Franco (syn. Abies menziesii Mirb.) (Rocky Mountain Douglas fir, Pinaceae) is an important timber tree native to western North America [12]. The tree has been introduced to many temperate regions throughout the world. There are two varieties of Douglas fir, P. menziesii var. menziesii (coastal Douglas fir), which ranges from coastal British Columbia south through the Cascades into the Coastal and Sierra Nevada mountains of northern California, and P. menziesii var. glauca (Mayr) Franco (Rocky Mountain Douglas fir), which ranges from central British Columbia south into Arizona and New Mexico (Figure 7) [13]. There are populations of P. menziesii in Mexico that are morphologically similar to P. menziesii var. glauca that have been referred to as Pseudotsuga menziesii var. oaxacana Debreczy & I. Rácz [14], but there is little support for this particular taxon [15]. The bark on young trees is thin, smooth, gray, and covered with resin blisters. On mature trees, it is thicker (3–6 cm) and furrowed. The leaves are needles (2–3 cm long) spirally arranged around the branch (Figure 8).
The essential oils of both varieties (menziesii and glauca) have been extensively investigated by von Rudloff [16] and by Adams and co-workers [15]. The coastal Douglas fir has been characterized by relatively high concentrations of β-pinene (20–35%), terpinolene (5–20%), and terpinen-4-ol (5–15%), while the Rocky Mountain Douglas fir has shown large concentrations of camphene (20–30%), bornyl acetate (20–30%), and α-pinene (15–20%) [16]. In this work, the leaf essential oils from three individuals collected in southern Idaho have been obtained and the essential oil compositions determined using gas chromatographic methods. A comparison with Douglas fir essential oils from coastal, Rocky Mountain, and samples cultivated outside North America has also been carried out.
Thuja plicata Donn ex D. Don (western red cedar, Cupressaceae) is a large to very large evergreen tree native to western North America, ranging along the Cascade-Coastal Mountain Ranges from southeastern Alaska to northern California, and inland in the Rocky Mountains from British Columbia to the panhandle of northern Idaho (Figure 9) [17]. Western red cedar is an important timber-producing tree and has been introduced to other temperate zone locations, including Europe, Great Britain, Australia, and New Zealand [18,19,20,21,22,23,24,25]. The thin, gray-brown bark forms vertical bands of fissures; the branch termini form flat boughs with scale-like leaves; the cones are 10–18 mm long and 4–5 mm wide with overlapping scales (Figure 10). The Nez Perce people used an infusion of the foliage to treat colds and coughs [5].

2. Results and Discussion

2.1. Essential Oil Composition

Essential oils of the conifer species were obtained by hydrodistillation and the essential oil compositions determined using gas chromatography (GC-MS and GC-FID).

2.1.1. Abies lasiocarpa var. lasiocarpa

The foliage (branch tips and leaves, no cones) from two individual mature A. lasiocarpa var. lasiocarpa trees (A.l.l. #1 and A.l.l. #2) from southern Idaho were hydrodistilled to give colorless essential oils in 1.611% and 1.857% yield based on masses of fresh/frozen plant material). Gas chromatographic analysis of the essential oils was carried out to assess the chemical compositions (Table 1).
The major components in A. lasiocarpa essential oils were limonene (20.3% and 34.6%), bornyl acetate (24.7% and 18.5%), β-pinene (13.6% and 9.3%), camphene (10.9% and 7.4%), and α-pinene (5.0% and 4.5%). The compositions are consistent with those reported by Adams and co-authors for Rocky Mountain subalpine fir from Montana and Utah [2].

2.1.2. Picea engelmannii subsp. engelmannii

Hydrodistillation of the branch tips and leaves of P. engelmannii subsp. engelmannii (P.e.e.) gave a yellow essential oil in 0.912% yield based on mass of fresh/frozen plant material. The essential oil composition is listed in Table 2. The essential oil was rich in oxygenated monoterpenoids (50.2%), including camphor (22.8%), borneol (8.3%), and camphene hydrate (6.0%), as well as monoterpene hydrocarbons, (38.2%) myrcene (11.7%) and camphene (6.0%). There have been previous examinations of P. engelmannii from Arizona [31] and from Poland [32].
An agglomerative hierarchical cluster (AHC) analysis was carried out to reveal the similarities between these essential oil samples (Figure 11). The samples from Arizona (sampled on 6 June, 20 June, and 25 July of 1984) showed wide variation in essential oil composition (<70% similarity) for the three dates. Mardarowicz and co-workers sampled a mature tree and saplings of cultivated trees in Poland [32]. The juvenile and mature foliar essential oils were very different in composition, but the composition of the mature foliar essential oil is similar (>80% similarity) to the P. engelmannii essential oil from Idaho. Thus, for example, the major components in the mature foliar essential oil from Poland were camphor (14.9%), borneol (5.2%), camphene hydrate (5.0%), myrcene (12.2%), and camphene (3.5%). Interestingly, the Poland sample had 5.6% benzaldehyde, which was not observed in the Idaho sample.

2.1.3. Pinus contorta subsp. latifolia

Leaves (needles) of P. contorta subsp. latifolia from two mature trees (P.c.l. #1 and P.c.l. #2) were hydrodistilled to give colorless essential oils in 3.105% and 1.702% yield based on masses of fresh/frozen plant material. The gas chromatographic results are summarized in Table 3. The major components in the essential oils were β-pinene (27.0% and 20.3%), β-phellandrene (21.8% and 20.9%), δ-3-carene (3.6% and 11.0%), (2E)-hexenal (7.1% and 5.3%), α-pinene (5.0% and 4.0%), and α-terpineol (6.7% and 5.7%).
In order to compare and contrast the essential oil compositions of P. contorta subsp. latifolia from Idaho with P. contorta subsp. latifolia from Alberta, Canada [33], P. contorta subsp. murrayana from Oregon [10], and P. contorta subsp. contorta from Oregon [11], an AHC analysis was carried out (Figure 12). The three P. contorta subsp. latifolia samples show > 90% similarity, while P. contorta subsp. murrayana shows 87% similarity to the latifolia subspecies. The least similar in essential oil composition is P. contorta subsp. contorta with only 45% similarity. Although β-phellandrene was the major component in all of the P. contorta essential oils, β-pinene was only a minor component (0.5%) in P. contorta subsp. contorta, but terpinen-4-ol was a major component (11.0%) in P. contorta subsp. contorta, which account for the lack of similarity of this essential oil.

2.1.4. Pseudotsuga menziesii var. glauca

Hydrodistillation of the leaves (needles) of P. menziesii from three individual trees (P.m.g. #1, P.m.g. #2, and P.m.g. #3) from southern Idaho gave pale-yellow essential oils in 0.658–1.462% yield based on masses of fresh/frozen plant material. The chemical compositions of the three P. menziesii samples are compiled in Table 4.
The major components in the essential oils were bornyl acetate (38.7–41.1%), camphene (15.0–19.5%), α-pinene (6.3–11.2%), and limonene (3.9–5.4%), confirming the identification of these samples as Rocky Mountain Douglas fir (P. menziesii var. glauca) [15,16]. In order to complement the volatile phytochemical differences between P. menziesii var. menziesii [15,34] and P. menziesii var. glauca as well as place samples from outside North America [31,35,36,37,38,39] into chemical context, both agglomerative hierarchical cluster (AHC) analysis (Figure 13) and principal component analysis (PCA, Figure 14) were carried out using the percent compositions of the major components (Supplementary Table S1).
There are two well-defined clusters based on the AHC. Cluster 1 is a cluster made up of samples from Idaho (this work), Yellowstone, Arizona, and New Mexico; dominated by bornyl acetate and camphene; and is clearly P. menziesii var. glauca based on the volatile phytochemicals and the geographical locations. Cluster 2 is made up of samples from Washington state (P. menziesii var. menziesii) as well as cultivated samples from Serbia, Romania, Austria, Bulgaria, Argentina, and New Zealand, and is defined by large concentrations of β-pinene, terpinolene, and sabinene. The chemical compositions of the non-North American cultivated samples are consistent with the menziesii variety and are likely derived from P. menziesii var. menziesii parents. There is one sample from Arizona [31] that does not fit into either the glauca or the menziesii varieties, and likely represents an “Interior Intermediate” chemotype [16].
The PCA verifies the AHC with the P. menziesii var. glauca group positively correlating with bornyl acetate and camphene. The P. menziesii var. menziesii group, on the other hand, positively correlates with β-pinene, terpinolene, and sabinene. The “Interior Intermediate” sample from Arizona correlates most strongly with camphene, α-pinene, β-pinene, and limonene.

2.1.5. Thuja plicata

Hydrodistillation of T. plicata foliage from five different trees (T.p. #1–T.p. #5) growing near Coeur d’Alene, Idaho, gave pale-yellow essential oils in yields ranging from 0.99% to 4.70% based on masses of fresh/frozen plant material. The essential oils were analyzed by gas chromatographic methods (GC-MS and GC-FID, Table 5).
The essential oils were dominated by α-thujone (72.5–77.8%) and β-thujone (5.2–8.2%), with notable quantities of sabinene (1.4–3.0%) and terpinene-4-ol (2.2–3.1%). The compositions observed are very similar to those previously reported by von Rudloff et al. (both coastal and interior populations of western North America) [40], Nikolić et al. (Serbia) [25], Tsiri et al. (Poland) [23], and Lis et al. (Poland) [24]. That is, the foliar essential oils of T. plicata, regardless of geographical location, have been dominated by α-thujone, with lesser amounts of β-thujone, sabinene, and terpinen-4-ol [40]. Samples from Poland, however, showed relatively high concentrations of fenchone (7.1–11.3%), which were not reported in the samples from Serbia or from Idaho. Thuja plicata has shown low genetic diversity [41], which is consistent with the low variation in essential oil composition.
The foliar essential oil of T. plicata has shown insecticidal [42], insect antifeedant [25], as well as antibacterial and antifungal [25,43] activities. The biological activities of T. plicata essential oil can be attributed to the major component, α-thujone. The toxicity of α-thujone has been determined to be due to modulation of the γ-aminobutyric acid (GABA) type A receptor [44]. α-Thujone, and to a lesser extent, β-thujone have shown antinociceptive activities in a rodent model [45]. In addition, thujone has shown anti-inflammatory activity due to inhibition of induced interleukin (IL-6 and IL-8) release [46]. Thus, the biological properties of α-thujone are consistent with the Native American herbal medicinal uses of the plant.
A comparison of essential oil compositions between the five species of conifers in this study (see Supplementary Table S2) shows that A. lasiocarpa var. lasiocarpa and P. menziesii var. glauca have similar compositions, both species are rich in bornyl acetate, camphene, and limonene. On the other hand, P. engelmanii var. engelmanii (dominated by camphor and myrcene), Pinus contorta subsp. latifolia (rich in β-pinene and β-phellandrene), and Thuja plicata (dominated by thujones), are completely dissimilar in composition with all of the other species.

2.2. Terpenoid Enantiomeric Distributions

Chiral gas chromatographic–mass spectral analyses were carried out on the essential oils of Abies lasiocarpa var. lasiocarpa, Picea engelmannii subsp. engelmannii, Pinus contorta subsp. latifolia, Pseudotsuga menziesii var. glauca, and Thuja plicata to discern the enantiomeric distribution of chiral monoterpenoids (see Table 6). Interestingly, the (−)-enantiomers were the predominant stereoisomers for α-pinene, camphene, sabinene, β-pinene, limonene, β-phellandrene, linalool, terpinen-4-ol, borneol, and α-terpineol for essential oils of the Pinaceae. In contrast, the (+)-enantiomers of α-thujene, α-pinene, sabinene, β-pinene, limonene, cis-sabinene hydrate, β-thujone, terpinen-4-ol, and α-terpineol were dominant in T. plicata (Cupressaceae) essential oils.
Consistent with these findings, the (−)-enantiomers predominate for camphene, β-pinene, limonene, β-phellandrene, and α-terpineol in the Pinaceae essential oils of Abies concolor, Abies balsamea [47], Picea pungens [48], Pinus ponderosa, Pinus contorta, and Pinus flexilis [11]. Likewise, while (+)-α-thujene was the exclusive enantiomer in T. plicata, (−)-α-thujene was dominant in A. concolor and A. balsamea [47]. Furthermore, in the wood essential oils of Sequoia sempervirens (Cupressaceae), (+)-α-pinene, (+)-limonene, and (+)-α-terpineol predominated [49]. In Juniperus (Cupressaceae) essential oils from southwestern Idaho, (+)-α-thujene, (+)-α-pinene, (+)-limonene, and (+)-cis-sabinene hydrate predominated [50].

3. Materials and Methods

3.1. Plant Material

Samples of A. lasiocarpa var. lasiocarpa, P. engelmannii subsp. engelmannii, P. contorta subsp. latifolia, and P. menziesii var glauca were collected from individual trees near Featherville, Boise National Forest, Idaho, on 25 August 2022 (Table 7). Several subsamples were collected from each individual tree. Voucher specimens (A. lasiocarpa var. lasiocarpa, WNS-All-5856; P. engelmannii subsp. engelmannii, WNS-Pee-5881; P. contorta subsp. latifolia, WNS-Pcl-5852; and P. menziesii var glauca, WNS-Pmg-5845) have been deposited in the University of Alabama in Huntsville herbarium. The trees were identified in the field by K. Swor and W.N. Setzer and later verified by comparison with samples from the New York Botanical Garden Virtual Herbarium (https://sweetgum.nybg.org/science/vh/, accessed on 26 September 2022). The samples were freshly frozen (−20 °C) until distilled. The foliage from each individual was hydrodistilled for 4 h using a Likens-Nickerson apparatus to give the essential oils (Table 7). The foliage of T. plicata was collected from several trees near Coeur d’Alene, Idaho on 21 September 2022. A voucher specimen of T. plicata (WNS-Tp-6050) has been deposited in the University of Alabama in Huntsville herbarium. The fresh foliage was stored frozen (−20 °C) until distilled. The T. plicata foliage from each tree was hydrodistilled using a Likens-Nickerson apparatus for 4 h to give pale-yellow essential oils with pungent odors (see Table 7).

3.2. Gas Chromatographic Analyses

Gas chromatography–mass spectrometry (GC-MS) was carried out using the instrumentation and conditions previously reported [51]: Shimadzu GC-MS-QP2010 Ultra (Shimadzu Scientific Instruments, Columbia, MD, USA), ZB-5ms GC column (5% phenyl polydimethylsiloxane, 60 m × 0.25 mm × 0.25 μm film thickness) (Phenomenex, Torrance, CA, USA), injector and detector temperatures = 260 °C, helium carrier gas (column head pressure = 208.5 kPa, flow rate = 2.00 mL/min), GC oven temperature program = 50 °C start, ramp to 260 °C at 2 °C/min. For each essential oil sample, 1.0 μL of a 5% (w/v) solution in CH2Cl2 was injected (splitting mode of 24.5:1). Retention index (RI) values were determined using a homologous series of n-alkanes [26]. The essential oil compositions were ascertained by comparison of their RI values and MS fragmentation patterns with those reported in the databases [27,28,29,30] using the LabSolutions GCMS solution software version 4.45 (Shimadzu Scientific Instruments, Columbia, MD, USA).
Gas chromatography with flame-ionization detection (GC-FID) was carried out as previously reported [51]: Shimadzu GC 2010 instrument with FID detector (Shimadzu Scientific Instruments, Columbia, MD, USA), ZB-5 GC column (60 m × 0.25 mm × 0.25 μm film thickness) (Phenomenex, Torrance, CA, USA), using the same operating conditions as above for GC-MS. The percent compositions were determined from raw peak areas without standardization.
Chiral GC-MS was carried out as previously reported [51]: Shimadzu GC-MS-QP2010S instrument (Shimadzu Scientific Instruments), Restek B-Dex 325 column (30 m × 0.25 mm diameter × 0.25 μm film thickness) (Restek Corp., Bellefonte, PA, USA), injector and detector temperatures = 240 °C. Helium carrier gas (column head pressure = 53.6 kPa, flow rate of 2.00 mL/min), GC oven program = 50 °C start, hold for 5 min, increased to 100 °C at 1.0 °C/min, then increased to 220 °C at 2 °C/min. For each essential oil sample, 0.3 μL of a 5% (w/v) solution in CH2Cl2 was injected (splitting mode = 24.0:1). The enantiomers were determined by comparison of retention times with authentic samples obtained from Sigma-Aldrich (Milwaukee, WI, USA). The enantiomer percentages were determined from raw peak areas.

3.3. Multivariate Analyses

For the agglomerative hierarchical cluster (AHC) analyses, the essential oil compositions for each species were treated as operational taxonomic units (OTUs), and the percentages of the most abundant essential oil components were used to delineate the chemical associations between the essential oil samples (P. engelmannii: tricyclene, α-pinene, camphene, benzaldehyde, β-pinene, myrcene, δ-3-carene, limonene, β-phellandrene, 1,8-cineole, fenchone, linalool, camphor, camphene hydrate, borneol, terpinen-4-ol, α-terpineol, piperitone, bornyl acetate, longifolene, (E)-β-caryophyllene, and α-cadinol; Pinus contorta: (2E)-hexenal, α-pinene, β-pinene, myrcene, δ-3-carene, 1,4-cineole, α-terpinene, limonene, β-phellandrene, γ-terpinene, terpinolene, terpinen-4-ol, α-terpineol, chavicol, thymol; Pseudotsuga menziesii: santene, tricyclene, α-pinene, camphene, sabinene, β-pinene, δ-3-carene, limonene, β-phellandrene, (Z)-β-ocimene, (E)-β-ocimene, γ-terpinene, terpinolene, camphene hydrate, borneol, terpinen-4-ol, α-terpineol, bornyl acetate, citronellyl acetate, geranyl acetate). Pearson correlation was used to measure similarity, and the unweighted pair group method with arithmetic average (UPGMA) was used for cluster definition. Principal component analysis (PCA) was performed for the visual verification of the essential oil inter-relationships of the different infraspecific taxa of P. menziesii using the major components as variables with a Pearson correlation matrix. The AHC and PCA analyses were performed using XLSTAT v. 2018.1.1.62926 (Addinsoft, Paris, France).

4. Conclusions

The essential oils of Rocky Mountain subalpine fir (Abies lasiocarpa var. lasiocarpa) (Pinaceae), Engelmann spruce (Picea engelmannii subsp. engelmannii) (Pinaceae), Rocky Mountain lodgepole pine (Pinus contorta subsp. latifolia) (Pinaceae), Rocky Mountain Douglas fir (Pseudotsuga menziesii var. glauca) (Pinaceae), and Western red cedar (Thuja plicata) (Cupressaceae) from Idaho have been obtained and analyzed by gas chromatographic methods. The essential oil compositions obtained in this work are qualitatively similar, but quantitatively different, to previously reported compositions and confirm and complement the previous reports. The quantitative similarities or differences in essential oil compositions are important; any commercial, cosmetic, fragrance, or medicinal uses of the essential oils derived from these plant species may depend on differences due to geographical, edaphic, climatic, or genetic differences. As far as we are aware, this report presents the first comprehensive analysis of the chiral terpenoid components in Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata. The (−)-enantiomers seem to predominate for many monoterpenoid constituents in the Pinaceae, but the (+)-enantiomers are favored in the Cupressaceae. Nevertheless, additional research on essential oils of the Pinaceae and Cupressaceae is needed (e.g., higher sampling variability and different geographical locations) to describe the chemical profiles, chemical compositions and enantiomeric distributions more reliably in the various species and infraspecific taxa of these two families.

Supplementary Materials

The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/molecules28062477/s1, Table S1: Major components of Pseudotsuga menziesii from different geographical locations; Table S2: Comparison of the major components in the essential oils of Abies lasiocarpa var. lasiocarpa (A.l.l.), Picea engelmanii var. engelmanii (P.e.e.), Pinus contorta subsp. latifolia (P.c.l.), Pseudotsuga menziesii var. glauca (P.m.g.), and Thuja plicata (T.p.).

Author Contributions

Conceptualization, W.N.S.; methodology, P.S. and W.N.S.; validation, P.S. and W.N.S.; formal analysis, P.S., A.P. and W.N.S.; investigation, K.S., P.S., A.P. and W.N.S.; data curation, P.S. and W.N.S.; writing—original draft preparation, W.N.S.; writing—review and editing, K.S., P.S. and W.N.S.; supervision, W.N.S.; project administration, W.N.S. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

All data are included in the article.

Acknowledgments

This work was carried out as part of the activities of the Aromatic Plant Research Center (APRC, https://aromaticplant.org/, accessed on 1 March 2023).

Conflicts of Interest

The authors declare no conflict of interest.

Sample Availability

Samples of the essential oils are not available from the authors.

References

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Molecules 28 02477 g001 550
Figure 1. Natural range of Abies lasiocarpa [6].
Figure 1. Natural range of Abies lasiocarpa [6].
Molecules 28 02477 g001
Molecules 28 02477 g002 550
Figure 2. Abies lasiocarpa var. lasiocarpa from southern Idaho. (A): bark of young tree. (B): bark of old tree. (C): foliage. Photographs by K. Swor.
Figure 2. Abies lasiocarpa var. lasiocarpa from southern Idaho. (A): bark of young tree. (B): bark of old tree. (C): foliage. Photographs by K. Swor.
Molecules 28 02477 g002
Molecules 28 02477 g003 550
Figure 3. Natural range of Picea engelmannii [6].
Figure 3. Natural range of Picea engelmannii [6].
Molecules 28 02477 g003
Molecules 28 02477 g004 550
Figure 4. Picea engelmannii subsp. engelmannii from southern Idaho. (A): bark. (B): foliage. Photographs by K. Swor.
Figure 4. Picea engelmannii subsp. engelmannii from southern Idaho. (A): bark. (B): foliage. Photographs by K. Swor.
Molecules 28 02477 g004
Molecules 28 02477 g005 550
Figure 5. Natural range of Pinus contorta. Molecules 28 02477 i001 P. contorta subsp. contorta. Molecules 28 02477 i002 P. contorta subsp. murrayana. Molecules 28 02477 i003 P. contorta subsp. latifolia [6].
Figure 5. Natural range of Pinus contorta. Molecules 28 02477 i001 P. contorta subsp. contorta. Molecules 28 02477 i002 P. contorta subsp. murrayana. Molecules 28 02477 i003 P. contorta subsp. latifolia [6].
Molecules 28 02477 g005
Molecules 28 02477 g006 550
Figure 6. Pinus contorta subsp. latifolia from southern Idaho. (A): bark. (B): leaves and cones. Photographs by K. Swor.
Figure 6. Pinus contorta subsp. latifolia from southern Idaho. (A): bark. (B): leaves and cones. Photographs by K. Swor.
Molecules 28 02477 g006
Molecules 28 02477 g007 550
Figure 7. Natural range of Pseudotsuga menziesii. Molecules 28 02477 i004 P. menziesii var. menziesii. Molecules 28 02477 i005 P. menziesii var. glauca [6].
Figure 7. Natural range of Pseudotsuga menziesii. Molecules 28 02477 i004 P. menziesii var. menziesii. Molecules 28 02477 i005 P. menziesii var. glauca [6].
Molecules 28 02477 g007
Molecules 28 02477 g008 550
Figure 8. Pseudotsuga menziesii var. glauca from southern Idaho. (A): bark of young tree. (B): bark of old tree. (C): leaves and cones. Photographs by K. Swor.
Figure 8. Pseudotsuga menziesii var. glauca from southern Idaho. (A): bark of young tree. (B): bark of old tree. (C): leaves and cones. Photographs by K. Swor.
Molecules 28 02477 g008
Molecules 28 02477 g009 550
Figure 9. Native range of Thuja plicata [6].
Figure 9. Native range of Thuja plicata [6].
Molecules 28 02477 g009
Molecules 28 02477 g010 550
Figure 10. Thuja plicata from northern Idaho. (A): bark. (B): foliage and cones. (C): scan of foliage and cones. Photographs by K. Swor.
Figure 10. Thuja plicata from northern Idaho. (A): bark. (B): foliage and cones. (C): scan of foliage and cones. Photographs by K. Swor.
Molecules 28 02477 g010
Molecules 28 02477 g011 550
Figure 11. Dendrogram based on hierarchical cluster analysis of Picea engelmannii foliar essential oil compositions. a Wagner et al., 1989 [31]. b Mardarowicz et al., 2004 [32].
Figure 11. Dendrogram based on hierarchical cluster analysis of Picea engelmannii foliar essential oil compositions. a Wagner et al., 1989 [31]. b Mardarowicz et al., 2004 [32].
Molecules 28 02477 g011
Molecules 28 02477 g012 550
Figure 12. Dendrogram based on hierarchical cluster analysis of Pinus contorta leaf essential oil compositions. P.c.l. = Pinus contorta subsp. latifolia, P.c.m. = Pinus contorta subsp. murrayana, P.c.c. = Pinus contorta subsp. contorta. a Pauly and von Rudloff, 1971 [33]. b Ankney et al., 2021 [10]. c Ankney et al., 2022 [11].
Figure 12. Dendrogram based on hierarchical cluster analysis of Pinus contorta leaf essential oil compositions. P.c.l. = Pinus contorta subsp. latifolia, P.c.m. = Pinus contorta subsp. murrayana, P.c.c. = Pinus contorta subsp. contorta. a Pauly and von Rudloff, 1971 [33]. b Ankney et al., 2021 [10]. c Ankney et al., 2022 [11].
Molecules 28 02477 g012
Molecules 28 02477 g013 550
Figure 13. Dendrogram based on hierarchical cluster analysis of Pseudotsuga menziesii chemical compositions. P.m.g. = Pseudotsuga menziesii var. glauca. APRC = Commercial essential oil samples from the Aromatic Plant Research Center collection. a Von Rudloff, 1973 [16]. b Wagner et al., 1989 [31]. c Mitić et al., 2021 [39]. d Pădure et al., 2008 [38]. e Buchbauer et al., 1994 [35]. f Adams, 2012 [34]. g Jirovetz et al., 2000 [36]. h Jirovetz et al., 2000 [37].
Figure 13. Dendrogram based on hierarchical cluster analysis of Pseudotsuga menziesii chemical compositions. P.m.g. = Pseudotsuga menziesii var. glauca. APRC = Commercial essential oil samples from the Aromatic Plant Research Center collection. a Von Rudloff, 1973 [16]. b Wagner et al., 1989 [31]. c Mitić et al., 2021 [39]. d Pădure et al., 2008 [38]. e Buchbauer et al., 1994 [35]. f Adams, 2012 [34]. g Jirovetz et al., 2000 [36]. h Jirovetz et al., 2000 [37].
Molecules 28 02477 g013
Molecules 28 02477 g014 550
Figure 14. Biplot based on principal component analysis of Pseudotsuga menziesii chemical compositions. P.m.g. = Pseudotsuga menziesii var. glauca. APRC = Commercial essential oil samples from the Aromatic Plant Research Center collection.
Figure 14. Biplot based on principal component analysis of Pseudotsuga menziesii chemical compositions. P.m.g. = Pseudotsuga menziesii var. glauca. APRC = Commercial essential oil samples from the Aromatic Plant Research Center collection.
Molecules 28 02477 g014
Table
Table 1. Chemical compositions (percent) of the foliar essential oils of Abies lasiocarpa var. lasiocarpa (Rocky Mountain subalpine fir) from southern Idaho.
Table 1. Chemical compositions (percent) of the foliar essential oils of Abies lasiocarpa var. lasiocarpa (Rocky Mountain subalpine fir) from southern Idaho.
RIcalcRIdbCompoundA.l.l. #1A.l.l. #2
881880Santene1.21.5
923923Tricyclene1.10.7
926925α-Thujene0.10.1
934933α-Pinene5.04.5
950950Camphene10.97.4
966969Methyl 2-methyl-3-hexenoatetrtr
972972Sabinenetr0.1
978978β-Pinene13.69.3
989989Myrcene1.11.5
10051004p-Mentha-1(7),8-dienetrtr
10071007α-Phellandrene0.20.3
10101009δ-3-Carenetr0.3
10171017α-Terpinene0.10.1
10251025p-Cymene0.10.2
10311030Limonene20.334.6
10351031β-Phellandrene6.77.1
10361034(Z)-β-Ocimene---0.1
103810412-Heptyl acetate0.2---
10461046(E)-β-Ocimene---0.7
10571057γ-Terpinene0.20.1
10691069cis-Sabinene hydratetrtr
10861086Terpinolene0.70.4
10891090Fenchone0.1tr
10911093p-Cymenenetr0.1
11011101Linalool0.50.4
11071108Maltoltr---
11131113(E)-4,8-Dimethylnona-1,3,7-trienetrtr
11181119endo-Fencholtrtr
11251124cis-p-Menth-2-en-1-ol0.40.3
11271126α-Campholenaltr---
11421142trans-p-Menth-2-en-1-ol0.30.2
11471145Camphor0.2tr
11511151Citronellaltrtr
11551156Camphene hydrate0.1tr
11581157iso-Isopulegoltrtr
11641165iso-Borneoltr---
11721173Borneol0.20.2
117911792-Isopropenyl-5-methyl-4-hexenal0.10.2
11801180Terpinen-4-ol0.20.2
11871187Cryptonetrtr
11881188p-Cymen-8-oltrtr
11911192Methyl salicylate0.1tr
11951195α-Terpineol0.40.3
11971196cis-Piperitoltr0.1
12091208trans-Piperitol0.20.1
12171217endo-Fenchyl acetatetr0.1
12281227Citronellol0.2tr
12291229Thymyl methyl ether3.5tr
12321231trans-Chrysanthyl acetatetrtr
12501252Isopentyl hexanoatetr---
12511255Geranioltr---
12541254Piperitone2.83.0
12571257Methyl citronellatetrtr
12861285Bornyl acetate24.718.5
12881287iso-Bornyl acetate0.2tr
12911289Thymoltr1.5
129212932-Undecanonetrtr
13141314Carvenolide0.10.1
13341335cis-Piperityl acetate0.1tr
13501350Citronellyl acetate1.00.7
13581361Neryl acetatetr0.1
13781378Geranyl acetate0.40.6
13901390trans-β-Elemenetrtr
14091408Acora-3,7(14)-diene---tr
14101411Longifolenetr0.1
14181414α-Cedrene---0.1
14511452α-Himachalenetr0.1
14521452(E)-β-Farnesenetrtr
14651465Bornyl butyratetrtr
14741475Selina-4,11-dienetrtr
14821483Citronellol isobutyrate---tr
14891489β-Selinene0.10.3
14951494δ-Decalactone0.3---
14961494α-Selinene0.10.5
15041504(E,E)-α-Farnesenetrtr
15081508β-Bisabolene0.30.9
15111511(Z)-γ-Bisabolene0.10.1
15261525Citronellyl butyrate0.10.1
15411541(E)-α-Bisabolenetr0.1
15551555Geranyl butyrate0.10.1
15601560(E)-Nerolidol0.30.1
15671564Citronellyl 2-methylbutanoate0.10.1
15721572Citronellyl isovaleratetrtr
15961596Geranyl 2-methylbutanoate0.1tr
16031604Geranyl isovaleratetrtr
16851686epi-α-Bisabololtrtr
16881688α-Bisabolol0.81.8
17151716Citronellyl hexanoatetrtr
17471748Geranyl hexanoatetrtr
18311832(2Z,6E)-Farnesyl acetatetrtr
19901989Manoyl oxidetrtr
20502049Abietatrienetrtr
20842086Abietadienetrtr
21432147Abienoltr0.1
Monoterpene hydrocarbons61.269.1
Oxygenated monoterpenoids35.826.8
Sesquiterpene hydrocarbons0.52.0
Oxygenated sesquiterpenoids1.11.9
Diterpenoidstraces0.2
Benzenoid aromatics0.1traces
Others0.4traces
Total identified99.2100.0
RIcalc = Retention index values determined using the method of van den Dool and Kratz [26]. RIdb = Reference retention index values from the databases [27,28,29,30]. A.l.l. = Abies lasiocarpa var. lasiocarpa. tr = trace (<0.05%).
Table
Table 2. Chemical composition (percent) of the foliar essential oil of Picea engelmannii subsp. engelmannii from southern Idaho.
Table 2. Chemical composition (percent) of the foliar essential oil of Picea engelmannii subsp. engelmannii from southern Idaho.
RIcalcRIdbCompound%
777769(2Z)-Penten-1-ol0.1
780772Prenol0.1
797797(3Z)-Hexenaltr
803801Hexanaltr
849849(2E)-Hexenal0.4
851853(3Z)-Hexenol0.2
8658601-Hexanoltr
881880Santene0.2
923923Tricyclene0.4
926925α-Thujene0.1
934932α-Pinene3.6
948948α-Fenchenetr
950950Camphene6.0
972971Sabinene0.3
978978β-Pinene2.4
990989Myrcene11.7
10081006α-Phellandrene0.1
10101008δ-3-Carene3.7
10171017α-Terpinene0.1
10251024p-Cymene0.2
10301030Limonene4.4
10321031β-Phellandrene4.3
103310321,8-Cineole2.4
10351034(Z)-β-Ocimenetr
10451045(E)-β-Ocimenetr
10551056Isoamyl butyratetr
10571057γ-Terpinene0.2
106310643-Methyl-2-butenyl butyrate0.1
10711069cis-Linalool oxide (furanoid)0.1
10811082p-Mentha-2,4(8)-dienetr
10851086Terpinolene0.7
10861086trans-Linalool oxide (furanoid)0.1
10881090Fenchone0.2
10901093p-Cymenene0.1
10941094Methyl benzoate0.1
11011101Linalool1.2
11211123endo-Fenchol0.1
11261124cis-p-Menth-2-en-1-ol0.2
11491145Camphor22.8
11531151Citronellaltr
11561156Camphene hydrate6.0
11631165Isoborneol0.2
11741173Borneol8.3
117911792-Isopropenyl-5-methyl-4-hexenal0.1
11811180Terpinen-4-ol0.6
11871186p-Cymen-8-ol0.5
11961195α-Terpineol2.8
11981197Estragole (=Methyl chavicol)0.1
12071205Verbenone0.1
12191218trans-Carveol0.1
12271227Citronellol0.7
12291229Thymyl methyl ether0.2
12501249Geraniol0.1
12541254Piperitone0.8
12841285Bornyl acetate2.4
13121314Carvenolide0.1
13481348α-Longipinene0.3
13721372Longicyclene0.1
13771378Geranyl acetate0.2
13901390trans-β-Elemene0.1
14091411Longifolene0.8
14191417(E)-β-Caryophyllene0.1
14381439Isoamyl benzoate0.1
14451443Prenyl benzoate0.1
14531452(E)-β-Farnesene0.1
14881487β-Selinenetr
14911490γ-Amorphenetr
14951497α-Selinene0.1
14981497α-Muurolene0.1
15071508β-Bisabolenetr
15091511β-Curcumenetr
15101511(Z)-γ-Bisabolenetr
15101512γ-Cadinene0.2
15181518δ-Cadinene0.5
15261528(E)-γ-Bisabolene0.1
15361538α-Cadinenetr
15401541(E)-α-Bisabolene0.1
15611561(E)-Nerolidol0.1
15751575Germacra-1(10),5-dien-4β-ol0.3
16011600α-Oplopenone0.1
161316161,10-di-epi-Cubenoltr
162616281-epi-Cubenol0.1
16411640τ-Cadinol0.4
16431644τ-Muurolol0.4
16451643α-Muurolol (=δ-Cadinol)0.1
16551655α-Cadinol1.2
16571660neo-Intermedeol0.1
16861686epi-α-Bisabolol0.2
17311735Oplopanone0.5
19271934Cembrene0.6
19391931Musk ambrette a0.1
19411947(3E)-Cembrene A0.2
19521947α-Springene0.1
19571961(3Z)-Cembrene A0.1
19971994Manoyl oxide0.1
200120009β-Isopimara-7,15-diene0.1
20462038Thunbergol A1.0
20562058Abietatriene0.1
20882086Abietadienetr
21492147cis-Abienol0.3
22332245Palustral0.8
22652266Dehydroabietal0.2
22952297Methyl isopimaratetr
22992302Methyl levopimaratetr
23002300Tricosane0.1
23092312Abietaltr
24002400Tetracosanetr
Monoterpene hydrocarbons38.2
Oxygenated monoterpenoids50.2
Sesquiterpene hydrocarbons2.5
Oxygenated sesquiterpenoids3.3
Diterpenoids3.4
Benzenoid aromatics0.4
Others1.0
Total identified99.1
RIcalc = Retention index values determined using the method of van den Dool and Kratz [26]. RIdb = Reference retention index values from the databases [27,28,29,30]. tr = trace (<0.05%). a May be a contaminant.
Table
Table 3. Leaf essential oil compositions (percent) of Pinus contorta subsp. latifolia from southern Idaho.
Table 3. Leaf essential oil compositions (percent) of Pinus contorta subsp. latifolia from southern Idaho.
RIcalcRIdbCompoundP.c.l. #1P.c.l. #2
782782Prenol0.10.1
797797(3Z)-Hexenal1.00.7
799801Hexanal1.41.0
8268282-Furfural---0.1
845849(2E)-Hexenal7.15.3
847853(3Z)-Hexenol0.50.5
923923Tricyclene0.10.1
926927α-Thujene0.10.1
933932α-Pinene5.04.0
947948α-Fenchenetr0.1
949950Camphene0.40.4
9709703,7,7-Trimethylcyclohepta-1,3,5-trienetr0.1
972971Sabinene0.30.4
978978β-Pinene27.020.3
989989Myrcene4.23.0
10071006α-Phellandrene0.90.7
10081008δ-3-Carene3.611.0
101510151,4-Cineole0.10.2
10171017α-Terpinene0.40.5
10191022m-Cymene---tr
10241024p-Cymene0.20.5
10291030Limonene3.33.7
10311031β-Phellandrene21.820.9
10351034(Z)-β-Ocimene2.13.2
10451045(E)-β-Ocimene0.10.6
10571057γ-Terpinene0.40.7
10701069cis-Linalool oxide (furanoid)0.20.5
10801082p-Mentha-2,4(8)-diene---0.1
10851086Terpinolene2.02.4
10861086trans-Linalool oxide (furanoid)0.30.6
10901091p-Cymenenetr0.2
10991099Linalool0.61.1
11051104Nonanal---0.1
11121113p-Mentha-1,3,8-triene---0.1
11191119endo-Fenchol0.20.2
11241124cis-p-Menth-2-en-1-ol0.50.6
11271127allo-Ocimene0.10.1
113411352-Vinylanisole---0.1
11351136Terpin-3-en-1-ol 0.10.1
11401140trans-Pinocarveol0.10.1
11421142trans-p-Menth-2-en-1-ol0.40.4
11461145Camphortr0.1
11541156Camphene hydrate0.20.1
11711170Borneol0.30.3
117811792-Isopropenyl-5-methyl-4-hexenal---0.1
11801180Terpinen-4-ol0.81.3
11861186p-Cymen-8-ol0.20.7
11941195α-Terpineol6.75.7
11961196cis-Piperitol0.10.2
11971197Methyl chavicol (=Estragole)0.20.3
12081208trans-Piperitol0.10.2
12501250Chavicol0.10.1
12531254Piperitone0.10.1
125612576-Undecanone0.10.1
12771277Phellandraltr0.1
12841285Bornyl acetate0.10.5
12901289Thymoltrtr
129312932-Undecanone0.10.2
15111512γ-Cadinene0.10.1
15171518δ-Cadinene0.20.2
15601562(E)-Nerolidol0.30.1
15611560Dodecanoic acid0.10.1
15751576Spathulenol0.10.2
16211582Selin-6-en-4β-ol0.20.1
162616281-epi-Cubenol0.10.1
16421640τ-Cadinol0.40.3
16441644τ-Muurolol0.40.3
16471651α-Muurolol (=δ-Cadinol)0.10.1
16561655α-Cadinol0.80.7
16581658Selin-11-en-4α-ol (=Kongol)0.10.1
17661769Benzyl benzoate0.20.1
18701869Benzyl salicylate0.30.1
19621958Palmitic acid0.2---
19961997Isopimaradiene---0.2
2013200718-nor-Abieta-8,11,13-triene0.20.2
20412047Thunbergol0.40.1
21782180Sandaracopimarinal0.10.2
22372243Isomiparinal0.30.5
22452250Palustral0.30.1
22492253Levopimarinal0.50.2
22772274Dehydroabietal0.20.1
23222314Abietal0.20.1
23802372Neoabietinal0.1tr
Monoterpene hydrocarbons71.873.3
Oxygenated monoterpenoids11.113.2
Sesquiterpene hydrocarbons0.30.2
Oxygenated sesquiterpenoids2.52.0
Diterpenoids2.41.6
Benzenoid aromatics0.80.7
Others10.88.3
Total identified99.799.2
RIcalc = Retention index values determined using the method of van den Dool and Kratz [26]. RIdb = Reference retention index values from the databases [27,28,29,30]. P.c.l. = Pinus contorta subsp. latifolia. tr = trace (<0.05%).
Table
Table 4. Chemical composition (percent) of the leaf essential oils of Pseudotsuga menziesii var. glauca from southern Idaho.
Table 4. Chemical composition (percent) of the leaf essential oils of Pseudotsuga menziesii var. glauca from southern Idaho.
RIcalcRIdbCompoundP.m.g. #1P.m.g. #2P.m.g. #3
883884Santene1.01.31.7
916918Prenyl acetatetrtrtr
921923Tricyclene1.21.81.8
924927α-Thujenetrtr0.1
933933α-Pinene6.39.111.2
952953Camphene15.015.219.5
973972Sabinene0.50.20.5
980978β-Pinene3.02.63.7
989991Myrcene0.81.20.8
998997Ethyl hexanoate------tr
10061007α-Phellandrene0.10.10.1
10091009δ-3-Carene0.50.3tr
101510151,4-Cineoletrtrtr
10171018α-Terpinene0.20.10.1
10241025p-Cymene0.20.10.1
10301030Limonene3.95.44.0
10311031β-Phellandrene0.40.40.4
103310321,8-Cineoletrtrtr
10351034(Z)-β-Ocimene0.1trtr
10471046(E)-β-Ocimene5.42.30.7
10581058γ-Terpinene0.40.20.2
10871086Terpinolene1.51.11.0
10901090Fenchonetrtrtr
10911093p-Cymenenetrtrtr
10951094Methyl benzoate0.1tr---
11011101Linalool1.61.44.0
11081108Maltol0.1------
11201120endo-Fencholtr0.1tr
11241125Methyl octanoate---trtr
11251124cis-p-Menth-2-en-1-ol0.10.1tr
11271127α-Campholenaltrtr0.1
11411142trans-p-Menth-2-en-1-ol0.10.1tr
11461145Camphortr0.10.1
11491149iso-Pulegol0.1trtr
11521152Citronellal1.00.40.1
11561156Camphene hydrate0.82.00.7
11641165iso-Borneoltr0.1tr
11701170Umbellulonetrtrtr
11721173Borneol0.70.81.0
117911792-Isopropenyl-5-methyl-4-hexenal tr0.10.1
11811180Terpinen-4-ol1.40.70.8
11891189p-Cymen-8-oltrtrtr
11921192Methyl salicylate0.8trtr
11951195α-Terpineol0.81.00.9
12061206Decanal0.10.10.1
12091209trans-Piperitoltr0.1tr
12181219endo-Fenchyl acetate0.20.10.2
12301232Citronellol1.91.00.2
12311229Thymyl methyl ether------tr
12381238Neral0.1tr---
12491248Carvotanacetone0.1------
12541255Geraniol0.1---tr
12551254Piperitone1.44.13.2
12701268Geranial0.10.1---
12871285Bornyl acetate40.241.138.7
12911287Isobornyl acetate0.30.10.2
12961296trans-Pinocarvyl acetatetrtrtr
13241326Myrtenyl acetatetrtrtr
132713274-Terpinenyl acetate0.10.10.1
13351335δ-Elemene---trtr
13501350Citronellyl acetate2.31.10.5
13521352α-Longipinenetr---0.1
13591361Neryl acetatetrtrtr
13761372Longicyclene------tr
13771377α-Copaene------tr
13801380Geranyl acetate2.70.50.2
13911390trans-β-Elemene0.10.10.1
14101411Longifolene0.10.20.3
14221424(E)-β-Caryophyllenetrtrtr
14341433trans-α-Bergamotenetr0.1tr
14561454α-Humulenetr0.10.1
14621463Tuberolactone---0.2---
14721471Massoia lactone---tr---
14771478γ-Muurolene------tr
14801482α-Amorphenetr0.1tr
14821483Germacrene Dtrtrtr
14831482γ-Himachalenetr0.1tr
14901490Prenyl benzoate0.10.1tr
14981497α-Muurolene------tr
15051505(E,E)-α-Farnesenetr---tr
15181518δ-Cadinene---trtr
15411541(E)-α-Bisabolenetr0.10.1
15631564(E)-Nerolidoltrtrtr
16071601Longiborneol (=Juniperol)0.10.1tr
16121613Humulene epoxide IItrtrtr
16301629iso-Spathulenol0.30.40.3
16531652β-Himachalol---0.20.1
16551655α-Cadinol0.10.1---
17731772Benzyl benzoate0.40.10.1
18741872Benzyl salicylate0.40.10.1
19301934Cembrene---0.10.2
19981994Manoyl oxide---trtr
20462038Thunbergol---0.10.1
20592062Manool0.10.40.3
21502152Abienol---0.10.1
Monoterpene hydrocarbons40.541.546.0
Oxygenated monoterpenoids56.055.051.1
Sesquiterpene hydrocarbons0.20.60.6
Oxygenated sesquiterpenoids0.50.70.4
Diterpenoids0.10.80.6
Benzenoid aromatics1.80.20.1
Others0.10.30.1
Total identified99.299.098.9
RIcalc = Retention index values determined using the method of van den Dool and Kratz [26]. RIdb = Reference retention index values from the databases [27,28,29,30]. P.m.g. = Pseudotsuga menziesii var. glauca. tr = trace (<0.05%).
Table
Table 5. Chemical composition (percent) of the foliar essential oils of Thuja plicata from northern Idaho.
Table 5. Chemical composition (percent) of the foliar essential oils of Thuja plicata from northern Idaho.
RIcalcRIdbCompoundT.p. #1T.p. #2T.p. #3T.p. #4T.p. #5
799801Hexanaltrtrtrtrtr
844842Ethyl 2-methylbutyrate0.20.10.20.30.2
847846(Z)-Salvenetrtrtrtrtr
850849(2E)-Hexenal0.10.10.10.10.1
851853(3Z)-Hexenol0.1tr0.1trtr
922923Tricyclenetrtrtrtrtr
925927α-Thujene0.40.10.30.20.2
933933α-Pinene1.70.61.40.80.8
948948α-Fenchenetrtrtrtrtr
950950Camphenetrtrtrtrtr
972972Sabinene3.01.72.42.21.4
978978β-Pinene0.10.10.10.10.1
989991Myrcene1.01.11.31.00.7
10161018α-Terpinene0.50.30.50.50.4
10231025p-Cymene0.60.40.50.40.6
10281030Limonene0.60.60.80.60.5
10301031β-Phellandrenetrtrtrtrtr
103410375-Methyl-(5E)-octen-2-one0.10.10.10.10.2
10571058γ-Terpinene0.90.70.80.80.7
10701069cis-Sabinene hydrate0.40.30.30.30.3
10851086Terpinolene0.20.20.20.20.2
10941093Ethyl sorbate---0.3-
10991098Perillenetrtrtrtrtr
11051101trans-Sabinene hydrate0.3----
11071105α-Thujone72.573.974.776.377.8
11191118β-Thujone7.48.26.16.65.2
11251124cis-p-Menth-2-en-1-ol0.20.20.20.20.1
11271126α-Campholenaltrtrtrtrtr
11431142trans-p-Menth-2-en-1-ol0.10.10.10.10.1
11461145trans-Verbenol0.10.10.10.10.1
11531153neo-3-Thujanol0.10.10.10.10.1
11581157Sabina ketone0.20.10.10.20.2
11761176trans-Isopulegonetr0.1trtr0.1
11821180Terpinen-4-ol3.12.73.12.92.2
11881186p-Cymen-8-ol0.20.20.20.20.3
11951195α-Terpineol0.30.30.30.20.2
11981197Methyl chavicol (=Estragole)0.30.50.40.60.3
120212134-Hydroxy-α-thujone0.60.40.40.51.0
12081208Verbenone0.10.10.10.10.2
12091209trans-Piperitol0.1trtrtrtr
12191218trans-Carveol0.1trtrtr0.1
12381238Carvacryl methyl ethertrtr0.1trtr
12431242Cuminaltrtrtrtr0.1
12441246Carvonetrtrtr0.10.1
12471250Ethyl oct-(2E)-enoate0.1trtrtrtr
12491249Carvotanacetone0.10.10.10.10.1
12611260trans-Sabinene hydrate acetate0.10.10.10.10.1
12691259Linalyl acetate0.20.20.30.20.2
12881286trans-Sabinyl acetate0.10.10.10.10.1
129012933-Thujanyl acetate0.20.10.20.10.1
12921290Menthyl acetate0.40.50.50.40.5
12991300Carvacrol0.10.10.10.10.1
13181322Myrtenyl acetatetr0.10.10.10.1
13301327p-Mentha-1,4-dien-7-ol0.10.10.10.10.2
133713354-Terpinenyl acetate0.10.10.10.10.1
13471346α-Terpinyl acetate0.30.30.30.20.2
13791378Geranyl acetate0.40.50.50.20.3
14011403Methyl eugenoltrtrtrtrtr
14471448(E)-Cinnamyl acetatetrtrtrtrtr
15821578Furopelargone Btr-0.1--
16081607β-Oplopenone0.10.10.1tr0.1
16611659α-Cadinoltr0.10.1trtr
17401738Oplopanone0.10.10.10.10.1
19231926Rimuene0.20.40.10.20.3
19591962Beyerene0.60.70.60.30.4
20642058Abietatrienetr0.1trtrtr
2174a15-Beyeren-19-ol methyl ethertr0.1trtrtr
2258b15-Beyeren-19-ol 0.20.70.10.20.3
23192315trans-Totaroltr0.2trtr0.1
2336c15-Beyeren-19-ol acetate1.01.31.11.11.6
Monoterpene hydrocarbons9.05.88.46.85.5
Oxygenated monoterpenoids87.789.088.189.690.2
Sesquiterpene hydrocarbons0.00.00.00.00.0
Oxygenated sesquiterpenoids0.20.30.30.10.2
Diterpenoids1.93.41.91.82.7
Benzenoid aromatics0.30.50.40.60.3
Others0.50.30.50.70.5
Total identified99.699.399.699.599.3
RIcalc = Retention index values determined using the method of van den Dool and Kratz [26]. RIdb = Reference retention index values from the databases [27,28,29,30]. T.p. = Thuja plicata. tr = trace (<0.05%). a The MS library match (NIST 20) is 91%, but a reference RI is not available. b The MS library match (NIST 20) is 87%, but a reference RI is not available. c The MS library match (NIST 20) is 92%, but a reference RI is not available.
Table
Table 6. Enantiomeric distribution of chiral terpenoid components (percentage of each enantiomer) in gymnosperm essential oils from Idaho.
Table 6. Enantiomeric distribution of chiral terpenoid components (percentage of each enantiomer) in gymnosperm essential oils from Idaho.
CompoundRT (min)A.l.l. #1A.l.l. #2P.e.e.P.c.l. #1P.c.l. #2P.m.g. #1P.m.g. #2P.m.g. #3T.p. #1T.p. #2T.p. #3T.p. #4T.p. #5
(+)-α-Thujene13.92ndndndndndndndnd100.0100.0100.0100.0100.0
(−)-α-Thujene13.990.00.00.00.00.0
(−)-α-Pinene15.9272.579.262.587.187.886.789.171.646.29.522.02.76.6
(+)-α-Pinene16.4027.520.837.512.912.213.310.928.453.890.578.097.393.4
(−)-Camphene17.7397.695.592.678.680.098.097.897.6ndndndndnd
(+)-Camphene18.302.44.57.421.420.02.02.22.4
(+)-Sabinene19.74ndndndndnd1.4nd3.2100.0100.0100.0100.0100.0
(−)-Sabinene20.6098.696.80.00.00.00.00.0
(+)-β-Pinene20.271.41.54.01.71.71.62.81.868.888.083.089.593.6
(−)-β-Pinene20.6298.698.596.098.398.498.497.298.231.212.017.010.56.4
(−)-α-Phellandrene22.5994.196.1ndndndndndndndndndndnd
(+)-α-Phellandrene22.815.93.9
(−)-Limonene25.0691.996.294.586.089.681.681.082.74.32.64.04.13.6
(+)-Limonene25.998.13.85.514.010.418.419.017.395.797.496.095.996.4
(−)-β-Phellandrene26.1599.9100.089.199.799.697.297.296.8ndndndndnd
(+)-β-Phellandrene26.880.10.010.90.30.42.82.83.2
(+)-cis-Sabinene hydrate40.70ndndndndndndndnd95.297.495.692.695.2
(−)-cis-Sabinene hydrate41.254.82.64.47.44.8
(+)-α-Thujone43.32ndndndndndndndnd0.00.00.00.00.0
(−)-α-Thujone44.88100.0100.0100.0100.0100.0
(−)-Linalool45.6971.668.268.179.580.091.992.695.0ndndndndnd
(+)-Linalool46.2428.431.831.920.520.08.17.45.0
(+)-β-Thujone46.06ndndndndndndndnd100.0100.0100.0100.0100.0
(−)-β-Thujone---0.00.00.00.00.0
(−)-Camphor49.310.0nd98.0ndndndndndndndndndnd
(+)-Camphor50.12100.02.0
(+)-Terpinen-4-ol54.64nd30.644.244.043.532.136.035.074.272.573.473.773.9
(−)-Terpinen-4-ol54.9369.455.855.056.567.964.065.025.827.526.626.326.1
(−)-Borneol58.59100.0100.0100.0nd100.097.7100.097.2ndndndndnd
(+)-Borneol59.110.00.00.00.02.30.02.8
(−)-Bornyl acetate59.46100.0100.0100.0nd100.0100.0100.0100.0ndndndndnd
(+)-Bornyl acetate---0.00.00.00.00.00.00.0
(−)-α-Terpineol59.73ndnd52.895.493.183.0nd82.829.736.130.529.132.4
(+)-α-Terpineol60.5847.24.66.917.017.270.363.969.570.967.6
(−)-Piperitone62.7479.082.3ndndnd100.0100.089.8ndndndndnd
(+)-Piperitone63.2221.017.70.00.010.2
(+)-β-Bisabolene75.3416.240.7ndndndndndndndndndndnd
(−)-β-Bisabolene75.5183.859.3
(−)-(E)-Nerolidol83.4079.3ndndndndndndndndndndndnd
(+)-(E)-Nerolidol83.5920.7
RT = retention time, A.l.l. = Abies lasiocarpa var. lasiocarpa, P.e.e. = Picea engelmannii subsp. engelmannii, P.c.l. = Pinus contorta subsp. latifolia, P.m.g. = Pseudotsuga menziesii var. glauca, T.p. = Thuja plicata, nd = not detected.
Table
Table 7. Collection and hydrodistillation details of Abies lasiocarpa var. lasiocarpa (A.l.l.) Picea engelmannii subsp. engelmannii (P.e.e.), Pinus contorta subsp. latifolia (P.c.l.), Pseudotsuga menziesii var. glauca (P.m.g.), and Thuja plicata (T.p.).
Table 7. Collection and hydrodistillation details of Abies lasiocarpa var. lasiocarpa (A.l.l.) Picea engelmannii subsp. engelmannii (P.e.e.), Pinus contorta subsp. latifolia (P.c.l.), Pseudotsuga menziesii var. glauca (P.m.g.), and Thuja plicata (T.p.).
Tree SampleTree CharacteristicsCoordinates, ElevationMass Foliage, g, Used for the DistillationEssential Oil Yield, g, (% Yield)
A.l.l. #1Mature, cone bearing43°38′11″ N, 115°21′16″ W, 1699124.942.013 (1.611%)
A.l.l. #2Mature, cone bearing43°39′26″ N, 115°24′28″ W, 2122 m231.034.291 (1.857%)
P.e.e.Mature, cone bearing43°37′22″ N, 115°25′52″ W, 2372 m200.641.830 (0.912%)
P.c.l. #1Mature, cone bearing43°37′56″ N, 115°19′30″ W, 1559 m72.022.236 (3.105%)
P.c.l. #2Mature, cone bearing43°37′52″ N, 115°23′3″ W, 1999 m88.741.510 (1.702%)
P.m.g. #1Mature, cone bearing43°36′40″ N, 115°17′2″ W, 1420 m182.911.738 (0.950%)
P.m.g. #2Mature, cone bearing43°37′33″ N, 115°18′25″ W, 1492 m208.223.045 (1.462%)
P.m.g. #3Mature, cone bearing43°37′46″ N, 115°22′0″ W, 1902 m189.211.235 (0.653%)
T.p. #1Mature, cone bearing47°36′32″ N, 116°40′12″ W, 664 m224.858.751 (3.892%)
T.p. #2Sapling47°36′32″ N, 116°40′12″ W, 664 m62.320.618 (0.992%)
T.p. #3Mature, cone bearing47°36′29″ N, 116°40′10″ W, 662 m263.266.973 (2.649%)
T.p. #4Large tree, no apparent cones47°36′1″ N, 116°39′30″ W, 722 m99.104.695 (4.738%)
T.p. #5Large tree, no apparent cones47°35′52″ N, 116°39′26″ W, 720 m89.473.960 (4.426%)
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Swor, K.; Satyal, P.; Poudel, A.; Setzer, W.N. Gymnosperms of Idaho: Chemical Compositions and Enantiomeric Distributions of Essential Oils of Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata. Molecules 2023, 28, 2477. https://doi.org/10.3390/molecules28062477

AMA Style

Swor K, Satyal P, Poudel A, Setzer WN. Gymnosperms of Idaho: Chemical Compositions and Enantiomeric Distributions of Essential Oils of Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata. Molecules. 2023; 28(6):2477. https://doi.org/10.3390/molecules28062477

Chicago/Turabian Style

Swor, Kathy, Prabodh Satyal, Ambika Poudel, and William N. Setzer. 2023. "Gymnosperms of Idaho: Chemical Compositions and Enantiomeric Distributions of Essential Oils of Abies lasiocarpa, Picea engelmannii, Pinus contorta, Pseudotsuga menziesii, and Thuja plicata" Molecules 28, no. 6: 2477. https://doi.org/10.3390/molecules28062477

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