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Article

Leaf Essential Oil Compositions and Enantiomeric Distributions of Monoterpenoids in Pinus Species: Pinus albicaulis, Pinus flexilis, Pinus lambertiana, Pinus monticola, and Pinus sabiniana

by
Alicia Moore
1,
Elizabeth Ankney
2,
Kathy Swor
3,
Ambika Poudel
4,
Prabodh Satyal
4 and
William N. Setzer
4,5,*
1
Independent Researcher, 6346 Pentz Rd., Paradise, CA 95969, USA
2
Independent Researcher, 141 W. 17th St., Lafayette, OR 97127, USA
3
Independent Researcher, 1432 W. Heartland Dr., Kuna, ID 83634, USA
4
Aromatic Plant Research Center, 230 N 1200 E, Suite 100, Lehi, UT 84043, USA
5
Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA
*
Author to whom correspondence should be addressed.
Molecules 2025, 30(2), 244; https://doi.org/10.3390/molecules30020244
Submission received: 16 December 2024 / Revised: 6 January 2025 / Accepted: 8 January 2025 / Published: 9 January 2025
(This article belongs to the Special Issue Chemical Analyses and Applications of Essential Oils)
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Abstract

:
Members of the Pinus genus are well known for their medicinal properties, which can be attributed to their essential oils. In this work, we have examined the leaf essential oils of five understudied Pinus species collected from various locations in western North America. The essential oils were obtained by hydrodistillation and analyzed by gas chromatographic methods, including enantioselective gas chromatography. Pinus albicaulis was dominated by (+)-δ-3-carene; Pinus flexilis was dominated by α-pinene (mostly (+)-α-pinene) and (−)-β-pinene; Pinus lambertiana was dominated by (−)-β-pinene; Pinus monticola was dominated by (−)-β-pinene, (+)-δ-3-carene, and (−)-α-pinene; and Pinus sabiniana was rich in (−)-α-pinene and limonene. While this work adds to our knowledge of Pinus essential oils, additional research is needed to more fully appreciate the geographic and altitudinal variations in the volatile compositions of these Pinus species.

1. Introduction

The genus Pinus L. is composed of around 134 species, distributed throughout the northern hemisphere, and introduced to several locations in the southern hemisphere [1]. Members of the Pinus genus are valued for their medicinal properties [2,3,4], which can be largely attributed to their essential oils. Common components in pine essential oils include α-pinene, β-pinene, myrcene, δ-3-carene, camphene, limonene, and β-phellandrene, among others [2]. In this study, several unstudied or understudied Pinus species from western North America have been obtained and analyzed using gas chromatographic methods.
Pinus albicaulis Engelm. (whitebark pine) is an evergreen monoecious tree found in Alpine habitats in western North America, including the Cascade, Rocky Mountain, and Sierra Nevada ranges (Figure 1) [5]. The trees grow up to 21 m tall, the bark is gray, and the leaves (needles) are five per fascicle (Figure 2). Whitebark pine is considered to be a keystone species, providing food for birds and mammals, slowing snowmelt runoff, and reducing soil erosion. Whitebark pine has co-evolved with Clark’s nutcracker (Nucifraga columbiana (A. Wilson)), which disperse the seeds of the tree [6]. Unfortunately, the population of this tree species has been declining at an alarming rate due to the invasive pathogen Cronarium ribicola J.C. Fisch., which causes blister rust, large-scale outbreaks of the mountain pine beetle (Dendroctonus ponderosae Hopkins), altered fire regimes from fire exclusion, and more frequent and severe fires due to climate change [7,8]. Whitebark pine deaths have increased from 43% to 54% from 2010 to 2019 [9]. Whitebark pine has recently (2022) been classified by the Endangered Species Act as a “threatened species” [10]. As far as we are aware, there have been no previous reports on the essential oil composition of P. albicaulis; identification of the volatile phytochemicals in whitebark pine may be useful in identifying potential bark beetle repellents or antifungal agents.
Pinus flexilis E. James (limber pine) is a five-needle pine species [9]. The tree is found in the Rocky Mountains of western North America, from southeastern British Columbia to southwestern Alberta, and south through Colorado and New Mexico. Limber pine is also found in the mountains of Utah, Idaho, Nevada, and California [12] (Figure 3). The tree grows up to 26 m tall, with gray bark and five needles per fascicle (Figure 4). The Navajo people used P. flexilis as a febrifuge, emetic, and cough medicine [13]. There has been one previous report on the leaf essential oil of P. flexilis from Idaho [14].
Pinus lambertiana Douglas (sugar pine) is found in montane dry to moist forests in western North America from Oregon, south through California, and into Baja California (Figure 5) [15]. These are very large trees, growing up to 75 m tall; the bark is cinnamon- to gray-brown in color and deeply furrowed. There are five leaves (needles) per fascicle; the seed cones are large (25–50 cm), yellow-brown, and resinous (Figure 6) [16]. The Mendocino Native Americans used P. lambertiana as a cathartic [17]. As far as we are aware, there have been no previous reports on the essential oil of P. lambertiana.
Pinus monticola Douglas ex D. Don (western white pine) is a large tree that is found in western North America from British Columbia; south through Washington, Montana, Idaho, Nevada, and Oregon; and into California (Figure 7) [18]. The tree is 30–50 m, up to 70 m tall; the bark is grey and smooth, becoming furrowed into hexagonal scaly plates in large individuals. There are five needles per fascicle; the seed cones are 10–25 cm long, creamy brown to yellowish (Figure 8) [18]. The Mahuna Native Americans of California took the plant internally to treat rheumatism [19]. There has been one previous report on the leaf essential oil of cultivated P. monticola from Argentina [20].
Pinus sabiniana Douglas (gray pine, foothill pine) is endemic to the dry foothills of the coast range and the Sierra Nevada Range in California, essentially encircling the Central Valley (Figure 9) [21]. The trees grow to 25 m tall, the bark is brown to near black and deeply furrowed, there are generally three needles per fascicle (15–32 cm long), and the seed cones are large (15–25 cm) (Figure 10) [22]. The Yuki people of California used the burning twigs and leaves of P. sabiniana as a sweat bath for rheumatism and bruises [17]. There has been one previous report on the leaf and wood essential oils of P. sabiniana [23].

2. Results and Discussion

2.1. Pinus albicaulis Engelm

Leaf essential oils of P. albicaulis were obtained from sites in Wyoming and California in yields ranging from 2.96% to 3.51%. The essential oil compositions of P. albicaulis are presented in Table 1. A total of 106 components were identified in the P. albicaulis essential oils, accounting for more than 99% of the compositions. The major components were δ-3-carene (22.0–37.3%), α-pinene (7.8–12.6%), limonene (6.8–9.7%), β-phellandrene (2.0–11.3%), myrcene (3.0–7.1%), α-terpinyl acetate (0.2–14.4%), and terpinolene (3.3–5.1%). The essential oils from the Wyoming trees and the California trees are qualitatively similar and show only minor quantitative differences. That is, agglomerative hierarchical cluster analysis (HCA) shows 84% similarity between the two collection sites (Figure 11). Furthermore, two-sample t-test comparisons between the major components are not significantly different (Table 2).

2.2. Pinus flexilis E. James

Leaf essential oils were obtained from three individual trees growing in southern Utah in yields of 4.51%, 3.99%, and 5.02%. A total of 86 components were identified in the leaf essential oils of P. flexilis, which accounted for 99.6%, 99.9%, and 99.9% of the compositions. The leaf essential oil compositions of P. flexilis are listed in Table 3. The essential oils were dominated by β-pinene (11.1–54.8%) and α-pinene (19.8–37.5%), with lesser percentages of limonene (2.7–7.4%), β-phellandrene (1.8–5.1%), α-terpineol (1.5–4.9%), and α-cadinol (1.9–8.3%). The chemical compositions of the samples from southern Utah are qualitatively similar to a P. flexilis sample from southwestern Idaho, which showed α-pinene (37.1%) and β-pinene (21.9%) as the major components [14].

2.3. Pinus lambertiana Douglas

Leaves of P. lambertiana were collected near Butte Meadows, California, and hydrodistilled to give colorless essential oils in yields ranging from 2.01% to 2.26%. The gas chromatographic analysis revealed compositions of 126 total identified components (Table 4). The major components in the essential oils were β-pinene (28.9–46.4%), α-pinene (11.4–20.3%), (E)-β caryophyllene (2.5–16.6%), germacrene D (4.4–13.0%), and α-terpineol (2.6–6.9%).

2.4. Pinus monticola Douglas ex D. Don

Needles of P. monticola were collected from three individual trees located on a lahar slope of Mt. St. Helens, Washington, and three individual trees located near Priest Lake, Idaho. Hydrodistillation gave colorless essential oils ranging from 1.71% to 2.03%. The gas chromatographic analysis led to the identification of a total of 114 components (Table 5). The major leaf oil components were β-pinene (16.7–25.6%), α-pinene (9.8–15.7%), δ-3-carene (8.2–12.9%), limonene (3.7–8.2%), β-phellandrene (3.4–6.2%), myrcene (3.9–4.9%), α-terpineol (2.1–7.8%), α-cadinol (0.7–6.9%), and trans-β-elemene (0.7–15.2%). A previous examination of P. monticola, cultivated in Valle Chico, Argentina, was found to show β-pinene (22.8%), α-pinene (21.0%), limonene (14.0%), isobornyl formate (5.7%), terpinolene (5.1%), myrcene (4.2%), and δ-3-carene (4.2%) as major components [20].
Pinus albicaulis, P. flexilis, P. lambertiana, and P, monticola are all members of the subgenus Strobus, section Quinquefoliae, subsection Strobus (the five-needle white pine group). In order to investigate the similarities and differences in volatile phytochemicals in these species, a hierarchical cluster analysis (HCA) and a principal component analysis (PCA) were carried out. The HCA shows three well-defined clusters based on the essential oil compositions (Figure 12): (a) a cluster dominated by β-pinene and α-pinene and made up of samples of P. flexilis and P. lambertiana; (b) a cluster dominated by δ-3-carene and made up of P. albicaulis samples from northern Wyoming and from northern California; and (c) a cluster defined by relatively large percentages of β-pinene, α-pinene, and δ-3-carene, composed largely by samples of P. monticola from Idaho and from Washington. The PCA further delineates the species based on essential oil compositions (Figure 13). The P. albicaulis samples all strongly correlate with δ-3-carene; P. lambertiana and P. flexilis essential oil samples correlate strongly with β-pinene; and P. monticola samples positively correlate with β-pinene, α-pinene, and δ-3-carene. Unless cones are present, it is generally difficult to distinguish P. flexilis from P. albicaulis [6]. However, the leaf volatile compositions readily distinguish the P. albicaulis from the other members of the Strobus group. Pinus albicaulis essential oils are dominated by δ-3-carene, while the other Pinus essential oils are rich in α- and β-pinenes. Thus, based on essential oil compositions, it may be possible to more confidently identify members of the Strobus subgenus.

2.5. Pinus sabiniana Douglas

Leaves of P. sabiniana were collected from three individual trees growing near Paradise, California. Hydrodistillation gave colorless essential oils in yields of 2.33 to 2.45%. The gas chromatographic analysis of the leaf essential oils resulted in the identification of 96 components, accounting for 99.6%, 99.6%, and 99.8% of the total compositions (Table 6). The leaf essential oils showed notable variation in compositions, depending on the elevation of the collection site, whether in Butte Creek Canyon (samples #1 and #2) or on the top of the butte in Paradise (sample #3). Thus, for example, the major component in samples #1 and #2 was α-pinene (65.0% and 61.2%) but only 15.8% in sample #3, while the major component in sample #3 was limonene (54.9%) but only 1.5% and 1.4% in samples #1 and #2. Other major components in the leaf essential oils were (Z)-β-ocimene (7.9%, 11.3%, and 9.6%), β-pinene (6.6%, 6.6%, and 2.0%), and myrcene (3.8%, 4.9%, and 5.7%). The leaf essential oil compositions in this study are in qualitative agreement with a previous study on P. sabiniana from Placerville, California, that showed α-pinene (39.1%), limonene (10.5%), β-phellandrene (10.4%), thunbergol (4.7%), (Z)-β-ocimene (4.6%), methyl chavicol (4.5%), myrcene (3.6%), and β-pinene (3.3%) to be the major components [23]. Note that in addition to elevation, a recent wildfire episode (the so-called Camp Fire, 8 November 2018 [29]) may also have affected the trees in this study.

2.6. Enantiomeric Distributions

The leaf essential oils of P. albicaulis, P. flexilis, P. lambertiana, P. monticola, and P. sabiniana were analyzed by enantioselective gas chromatography in order to determine the enantiomeric distributions of chiral monoterpenoid components. The enantiomeric distributions of chiral monoterpenoid components found in the Pinus species are compiled in Table 7, Table 8, Table 9, Table 10 and Table 11, respectively.
Only one enantiomer of α-thujene was observed in P. albicaulis or P. flexilis. Unfortunately, the RI values for (+)- and (−)-α-thujene are very similar, so the assignment of (−)-α-thujene is tentative. Interestingly, the enantiomeric distribution for α-pinene showed (+)-α-pinene to be dominant in P. flexilis from southern Utah, whereas (−)-α-pinene dominated P. albicaulis. It would be tempting to suggest that the enantiomeric distribution of α-pinene could serve to differentiate P. albicaulis from P. flexilis, but (−)-α-pinene dominated P. flexilis from southern Idaho [14]. Indeed, the enantiomeric distribution of α-pinene in Pinus species is variable both between species and within species [14,30]. Nevertheless, (−)-α-pinene was dominant in P. lambertiana, P. monticola, and P. sabiniana.
(−)-Limonene often dominates the essential oils of Pinus species [14], but there are exceptions (e.g., Pinus mugo Turra [31], Pinus sylvestris L. [31], and Pinus uncinata subsp. uliginosa (G.E.Neumann ex Wimm.) Businský [32]). In this work, (−)-limonene was dominant in P. albicaulis, P. flexilis, and P. lambertiana, but the limonene distribution was variable in P. monticola and P. sabiniana.
Similarly, (−)-β-phellandrene was dominant in P. albicaulis, P. flexilis, P. lambertiana, and P. sabiniana, consistent with observations in Pinus ponderosa Douglas ex C. Lawson var. ponderosa, Pinus contorta Douglas ex Loudon subsp. contorta, P. flexilis from Idaho [14], and Pinus contorta subsp. murrayana (Balf.) Engelm. [33]. In contrast, however, β-phellandrene was virtually racemic in P. monticola. The (−)-enantiomers dominated camphene, β-pinene, terpinen-4-ol, and α-terpineol in P. albicaulis, P. flexilis, P. lambertiana, P. monticola, and P. sabiniana. (−)-Sabinene was dominant in the leaf essential oils of P. albicaulis and P. flexilis. Only one enantiomer was observed for δ-3-carene in P. albicaulis, P. flexilis, and P. monticola. The observed RI value is consistent with (+)-δ-3-carene, but a reference for (−)-δ-3-carene was not available for comparison. The only enantiomer of borneol was (−)-borneol in the essential oils of P. monticola, which is consistent with those observed in the essential oils of P. contorta latifolia [33], P. flexilis from Idaho [14], Pinus edulis Engelm., and Pinus monophylla Torr. & Frém. [30].

3. Materials and Methods

3.1. Collection and Identification

The collection details are summarized in Table 12. Leaves (needles) were collected from individual trees at the locations indicated. Several branch tips from each individual tree were collected. Voucher specimens were deposited with the University of Alabama in Huntsville herbarium. Identification in the field was carried out by W.N. Setzer and later verified by comparison with herbarium samples from the C.V. Starr Virtual Herbarium, New York Botanical Garden (https://sweetgum.nybg.org/science/vh/, accessed on 12 December 2024). The leaves were stored frozen (−20 °C) until hydrodistillation.

3.2. Essential Oils

The leaf essential oils of the Pinus species were obtained by hydrodistillation of each tree sample using a Likens–Nickerson apparatus for four hours with continuous extraction of the distillate with dichloromethane to give colorless essential oils. The hydrodistillation yields are summarized in Table 12.

3.3. Gas Chromatographic Analyses

The Pinus leaf essential oils were subjected to gas chromatographic analyses (GC-FID, GC-MS, and enantioselective GC-MS) as previously described [14,33]. One replicate was carried out for each essential oil.

3.4. Statistical Analyses

The agglomerative hierarchical cluster analyses (HCA) and principal component analyses (PCA) were carried out using XLSTAT v. 2018.1.1.62926 (Addinsoft, Paris, France). In the case of HCA on P. albicaulis, the percentages of the major components (δ-3-carene, α-pinene, β-pinene, limonene, myrcene, β-phellandrene, α-terpinyl acetate, α-cadinol, terpinolene, camphene, α-terpineol, and germacrene D) were used, Pearson correlation was used to measure similarity, and the unweighted pair group method with arithmetic average (UPGMA) was used for cluster definition. For the HCA on the Strobus group, the concentrations of the most abundant components (β-pinene, α-pinene, δ-3-carene, limonene, α-terpineol, β-phellandrene, myrcene, α-cadinol, germacrene D, (E)-β-caryophyllene, terpinolene, camphene, α-terpinyl acetate, and trans-β-elemene) were used. Dissimilarity was used to determine clusters considering Euclidean distance, and Ward’s method was used to define agglomeration. A PCA, type Pearson correlation, was carried out to verify the results of the HCA using the same major components. Student’s t-test [34] was used to compare the major components in the P. albicaulis samples using Minitab® 18 (Minitab Inc., State College, PA, USA). Differences of p < 0.05 were considered to be statistically significant.

4. Conclusions

This report, for the first time, presents the leaf essential oil compositions, including enantiomeric distributions, for P. albicaulis and P. lambertiana. In addition, the enantiomeric distributions have been determined for P. monticola and P. sabiniana. The pine essential oils examined in this study reveal high concentrations of α-pinene and β-pinene, typical for pine species. There are, however, interspecific variations in compounds such as δ-3-carene, (E)-β-caryophyllene, and germacrene D. The enantiomeric distributions are, in general, inconsistent throughout the genus. However, the differences observed may be useful in identifying species, hybrids, or essential oil adulteration. An obvious limitation of this study is that samples were obtained opportunistically, with only a few samples of each species obtained from limited geographical locations. While this work does provide additional insight into the essential oil compositions of several understudied Pinus species in western North America, additional research is needed to confirm these observations. For example, are the leaf essential oil compositions of P. albicaulis and P. flexilis relatively consistent throughout their range? Additional collections and analyses of the Pinus species from other locations in their respective ranges would provide additional information regarding the volatile phytochemistry of these pine trees. Depending on availability (e.g., Pinus albicaulis is a threatened species), the essential oils may be useful in pharmaceuticals, cosmetics, or aromatherapy.

Author Contributions

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

Funding

This study received no external funding.

Institutional Review Board Statement

Not applicable.

Informed Consent Statement

Not applicable.

Data Availability Statement

All data are available within this manuscript.

Acknowledgments

We are grateful to James Moore and Dewey Ankney for help with the collection of plant material. This work was carried out as part of the activities of the Aromatic Plant Research Center (APRC, https://aromaticplant.org/).

Conflicts of Interest

The authors declare no conflicts of interest.

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Molecules 30 00244 g001
Figure 1. Range of Pinus albicaulis Engelm. [11].
Figure 1. Range of Pinus albicaulis Engelm. [11].
Molecules 30 00244 g001
Molecules 30 00244 g002
Figure 2. Pinus albicaulis Engelm. (A): The tree habit. (B): Bark. (C): Leaves. (D): A scan of a twig with leaves. Photographs by K. Swor at the time of collection.
Figure 2. Pinus albicaulis Engelm. (A): The tree habit. (B): Bark. (C): Leaves. (D): A scan of a twig with leaves. Photographs by K. Swor at the time of collection.
Molecules 30 00244 g002
Molecules 30 00244 g003
Figure 3. Natural range of Pinus flexilis E. James [11].
Figure 3. Natural range of Pinus flexilis E. James [11].
Molecules 30 00244 g003
Molecules 30 00244 g004
Figure 4. Pinus flexilis E. James. (A): A branch with leaves (needles). (B): Bark. Photographs by K. Swor at the time of collection.
Figure 4. Pinus flexilis E. James. (A): A branch with leaves (needles). (B): Bark. Photographs by K. Swor at the time of collection.
Molecules 30 00244 g004
Molecules 30 00244 g005
Figure 5. Natural range of Pinus lambertiana Douglas [11].
Figure 5. Natural range of Pinus lambertiana Douglas [11].
Molecules 30 00244 g005
Molecules 30 00244 g006
Figure 6. Pinus lambertiana Douglas. (A): The tree habit. (B): Bark. (C): Leaves (needles). (D): A scan of a twig with leaves. Photographs by A. Moore at the time of collection.
Figure 6. Pinus lambertiana Douglas. (A): The tree habit. (B): Bark. (C): Leaves (needles). (D): A scan of a twig with leaves. Photographs by A. Moore at the time of collection.
Molecules 30 00244 g006
Molecules 30 00244 g007
Figure 7. Natural range of Pinus monticola Douglas ex. D. Don. [11].
Figure 7. Natural range of Pinus monticola Douglas ex. D. Don. [11].
Molecules 30 00244 g007
Molecules 30 00244 g008aMolecules 30 00244 g008b
Figure 8. Pinus monticola Douglas ex. D. Don. (A): The tree habit. (B): The bark of a young tree. (C): Leaves (needles). (D): A scan of leaves. Photographs by K. Swor at the time of collection.
Figure 8. Pinus monticola Douglas ex. D. Don. (A): The tree habit. (B): The bark of a young tree. (C): Leaves (needles). (D): A scan of leaves. Photographs by K. Swor at the time of collection.
Molecules 30 00244 g008aMolecules 30 00244 g008b
Molecules 30 00244 g009
Figure 9. Natural range of Pinus sabiniana Douglas in California [11].
Figure 9. Natural range of Pinus sabiniana Douglas in California [11].
Molecules 30 00244 g009
Molecules 30 00244 g010aMolecules 30 00244 g010b
Figure 10. Pinus sabiniana Douglas. (A): The habit of the tree. (B): Bark. (C): Leaves (needles). (D): A pressed sample of leaves. Photographs by A. Moore at the time of collection.
Figure 10. Pinus sabiniana Douglas. (A): The habit of the tree. (B): Bark. (C): Leaves (needles). (D): A pressed sample of leaves. Photographs by A. Moore at the time of collection.
Molecules 30 00244 g010aMolecules 30 00244 g010b
Molecules 30 00244 g011
Figure 11. A dendrogram based on an agglomerative hierarchical cluster analysis of the major components (δ-3-carene, α-pinene, β-pinene, limonene, myrcene, β-phellandrene, α-terpinyl acetate, α-cadinol, terpinolene, camphene, α-terpineol, and germacrene D) in the leaf essential oils of Pinus albicaulis.
Figure 11. A dendrogram based on an agglomerative hierarchical cluster analysis of the major components (δ-3-carene, α-pinene, β-pinene, limonene, myrcene, β-phellandrene, α-terpinyl acetate, α-cadinol, terpinolene, camphene, α-terpineol, and germacrene D) in the leaf essential oils of Pinus albicaulis.
Molecules 30 00244 g011
Molecules 30 00244 g012
Figure 12. Dendrogram based on hierarchical cluster analysis of leaf essential oil compositions of Pinus albicaulis, Pinus flexilis, Pinus lambertiana, and Pinus monticola.
Figure 12. Dendrogram based on hierarchical cluster analysis of leaf essential oil compositions of Pinus albicaulis, Pinus flexilis, Pinus lambertiana, and Pinus monticola.
Molecules 30 00244 g012
Molecules 30 00244 g013
Figure 13. Biplot based on principal component analysis of Pinus albicaulis, Pinus flexilis, Pinus lambertiana, and Pinus monticola leaf essential oil compositions.
Figure 13. Biplot based on principal component analysis of Pinus albicaulis, Pinus flexilis, Pinus lambertiana, and Pinus monticola leaf essential oil compositions.
Molecules 30 00244 g013
Table 1. Leaf essential oil compositions (percentages) of Pinus albicaulis Engelm. from Wyoming and from California.
Table 1. Leaf essential oil compositions (percentages) of Pinus albicaulis Engelm. from Wyoming and from California.
RIcalcRIdbCompoundsP. alb. WY#1P. alb. WY#2P. alb. CA#1P. alb. CA#2
779773Prenoltr0.1trtr
788797(3Z)-Hexenaltr0.1trtr
798801Hexanal0.20.30.10.2
850849(2E)-Hexenal1.11.60.60.7
851847(3E)-Hexenol0.51.31.91.7
861864(2E)-Hexenoltr0.1trtr
8648671-Hexanol0.10.20.10.1
879880Santene0.20.10.10.1
922923Tricyclene0.30.20.10.2
925925α-Thujene1.10.60.50.5
933933α-Pinene12.412.68.97.8
947948α-Fenchenetrtrtrtr
949950Camphene3.81.91.41.5
9689703,7,7-Trimethylcyclohepta-1,3,5-triene0.10.1trtr
971971Sabinene1.30.80.50.8
977978β-Pinene2.85.23.32.4
988989Myrcene3.04.27.16.7
10051005(3Z)-Hexenyl acetate--0.10.2
10071007α-Phellandrene0.10.70.70.4
10091009δ-3-Carene37.332.922.028.3
10171018α-Terpinene0.50.40.40.5
10191022m-Cymenetrtrtrtr
10251025p-Cymene0.20.40.40.3
10291030Limonene8.79.78.46.8
10311031β-Phellandrene2.011.32.92.0
103210321,8-Cineoletrtr--
10351035(Z)-β-Ocimenetrtrtrtr
103710412-Heptyl acetate0.30.30.30.5
10451045(E)-β-Ocimene0.10.20.30.2
10571057γ-Terpinene0.90.70.60.8
10841086Terpinolene5.13.63.34.1
109010902-Nonanone--0.10.1
10911091p-Cymenene0.10.1--
10991101Linalooltrtrtrtr
11061107Nonanaltrtrtrtr
11251124cis-p-Menth-2-en-1-ol0.20.30.20.1
11281127α-Campholenal0.10.1tr0.1
11431142trans-p-Menth-2-en-1-ol0.10.20.10.1
11551156Camphene hydrate0.10.1trtr
11721171p-Mentha-1,5-dien-8-ol0.10.1trtr
11811180Terpinen-4-ol1.71.51.61.7
11861187Cryptone-0.1--
11881188p-Cymen-8-ol0.10.20.10.1
11961195α-Terpineol0.50.71.20.6
11981198Estragole (=Methyl chavicol)tr0.31.60.7
12291229Thymyl methyl ether0.10.2--
123312332-Nonyl acetate0.1---
12721274Cyclooctyl acetate0.1-0.10.2
12831285Bornyl acetate3.41.41.81.6
129112932-Undecanonetr-0.10.1
133213324-Terpinyl acetate0.3tr0.30.3
13341335δ-Elemenetrtr-tr
13421346α-Terpinyl acetate1.20.214.49.4
13461346α-Cubebene-0.1--
135713572-Methylundecanaltrtr--
13581361Neryl acetatetrtr--
13741375α-Copaenetr0.10.1tr
13781378Geranyl acetate0.10.10.10.2
13811383cis-β-Elemenetr-trtr
13821382β-Bourbonenetr0.1trtr
13861387β-Cubebene--trtr
13881390trans-β-Elemene0.3tr0.30.4
14171417(E)-β-Caryophyllenetr0.30.70.2
14281430β-Copaenetrtrtrtr
14321432trans-α-Bergamotene-tr--
14391440(Z)-β-Farnesene-0.1--
14471446cis-Muurola-3,5-dienetrtrtrtr
14511451(E)-β-Farnesenetrtrtrtr
14541454α-Humulene-tr0.20.1
14611463cis-Cadina-1(6),4-dienetr-trtr
14701472trans-Cadina-1(6),4-dienetrtr0.10.1
14731475γ-Muurolene0.1tr0.10.2
14801480Germacrene D0.60.71.41.9
14881489β-Selinene0.1---
14901492trans-Muurola-4(14),5-diene0.1tr0.10.1
14941497Bicyclogermacrene0.30.10.20.3
14961497Valencene--0.10.1
14971497α-Muurolene0.20.10.30.5
15061508β-Bisabolene0.10.1-0.1
15111512γ-Cadinene0.30.10.40.6
15161518δ-Cadinene0.90.31.52.3
15201519trans-Calamenene--0.1tr
15211521Zonarene0.10.10.10.1
15311533trans-Cadina-1,4-diene--tr0.1
15351538α-Cadinenetrtr0.10.1
15611561(E)-Nerolidol0.10.1--
15621560Dodecanoic acidtr0.1trtr
15741574Germacra-1(10),5-dien-4β-ol0.40.10.30.4
15761576Spathulenol0.20.20.20.2
15801587Caryophyllene oxide--0.1tr
15921593Ethyl laurate-0.1--
16001600α-Oplopenone0.1-0.20.2
161416141,10-di-epi-Cubenol---0.1
162616281-epi-Cubenol0.1tr0.20.2
16411640τ-Cadinol0.50.10.91.3
16441644τ-Muurolol0.80.21.31.8
16461643α-Muurolol (=δ-Cadinol)0.40.10.50.7
16561655α-Cadinol2.20.53.44.4
16861688α-Bisabolol0.20.2-0.1
17641769Benzyl benzoate--0.10.1
18141817Hexadecanaltrtr0.1tr
19881989Manoyl oxide0.30.30.40.3
20372038Thunbergol A0.20.2tr0.2
20532053Manool0.50.10.1-
2217---iso-Pimarinal a0.10.10.10.1
22252245Palustral0.20.20.10.1
Monoterpene hydrocarbons79.985.660.863.3
Oxygenated monoterpenoids8.05.119.814.3
Sesquiterpene hydrocarbons3.02.15.77.2
Oxygenated sesquiterpenoids5.01.47.19.2
Diterpenoids1.20.90.70.6
Benzenoid aromaticstr0.31.60.8
Others2.54.23.53.8
Total identified99.599.699.299.3
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a ZB-5ms column [24]. RIdb = Retention index values obtained from the databases [25,26,27,28]. a A reference RI value was not available, but the MS showed a 94% match. WY = Wyoming. CA = California. Percentages were determined based on peak areas.
Table 2. Comparison (t-test) of concentrations of major components of Pinus albicaulis leaf essential oils collected from Wyoming and California.
Table 2. Comparison (t-test) of concentrations of major components of Pinus albicaulis leaf essential oils collected from Wyoming and California.
CompoundsAverage Concentration ± Standard Deviation (%)p-Value
WyomingCalifornia
δ-3-Carene35.10 ± 3.1125.15 ± 4.450.235
α-Pinene12.50 ± 0.148.35 ± 0.780.085
β-Pinene4.00 ± 1.702.85 ± 0.640.534
Limonene9.20 ± 0.717.60 ± 1.130.339
Myrcene3.60 ± 0.856.90 ± 0.280.121
β-Phellandrene6.65 ± 6.582.45 ± 0.640.534
α-Terpinyl acetate0.70 ± 0.7111.90 ± 3.540.142
Terpinolene4.35 ± 1.063.70 ± 0.570.584
Table 3. Leaf essential oil compositions (percentages) of Pinus flexilis E. James collected in southern Utah.
Table 3. Leaf essential oil compositions (percentages) of Pinus flexilis E. James collected in southern Utah.
RIcalcRIdbCompoundsP.flex. UT#1P.flex. UT#2P.flex. UT#3
779773Prenol0.20.1tr
788797(3Z)-Hexenal--0.1
798801Hexanal0.10.10.1
850849(2E)-Hexenal--0.8
851847(3E)-Hexenol2.41.10.5
879880Santenetrtr-
922923Tricyclene0.20.40.1
925925α-Thujene0.40.50.1
933933α-Pinene22.937.519.8
947948α-Fenchenetrtrtr
949950Camphene2.04.80.5
952953Thuja-2,4(10)-dienetrtrtr
971971Sabinene2.40.10.1
977978β-Pinene11.134.954.8
988989Myrcene4.02.02.9
10051005(3Z)-Hexenyl acetate0.50.10.1
10071007α-Phellandrene0.10.10.1
10091009δ-3-Carene0.10.90.7
10121012Hexyl acetatetr-tr
10171018α-Terpinene0.60.10.1
10251025p-Cymene0.20.1tr
10291030Limonene7.42.72.7
10311031β-Phellandrene5.11.82.3
10351035(Z)-β-Ocimenetrtrtr
10451045(E)-β-Ocimene0.1trtr
10571057γ-Terpinene1.00.20.1
10841086Terpinolene2.41.30.8
10911091p-Cymenene0.1-tr
109710996-Camphenonetrtr-
10991101Linalool0.40.10.1
11001100Undecane--tr
11061107Nonanal0.1trtr
11201119endo-Fenchol-0.1-
11251124cis-p-Menth-2-en-1-ol0.2trtr
11281127α-Campholenal0.10.10.1
11411141trans-Pinocarveol-0.1-
11431142trans-p-Menth-2-en-1-ol0.1tr0.1
11551156Camphene hydrate0.20.20.1
11631164Pinocarvone-trtr
11721171p-Mentha-1,5-dien-8-oltr0.1tr
11811180Terpinen-4-ol2.50.30.3
11881188p-Cymen-8-ol0.1--
11961195α-Terpineol1.52.64.9
12081208Verbenone-0.1tr
12291229Thymyl methyl ether0.10.10.1
12521252Chavicol1.00.70.2
125512576-Undecanonetrtr0.2
12721274Cyclooctyl acetate--0.1
12831285Bornyl acetate0.10.20.2
129112932-Undecanone0.70.50.5
135713572-Methylundecanal0.20.20.1
13741375α-Copaene0.1trtr
13781378Geranyl acetate0.1-0.1
13821382β-Bourbonene0.4trtr
13881390trans-β-Elemene0.1-tr
139413932-Dodecanone0.1trtr
14101410Dodecanal0.1--
14281430β-Copaene0.1tr-
14471446cis-Muurola-3,5-diene0.1--
14611463cis-Cadina-1(6),4-diene0.1-tr
14701472trans-Cadina-1(6),4-diene0.1trtr
14731475γ-Muurolene0.40.10.1
14801480Germacrene D4.60.60.8
14901492trans-Muurola-4(14),5-diene0.2trtr
14941497Bicyclogermacrene0.60.1tr
149414942-Tridecanone-0.10.1
14971497α-Muurolene0.50.10.1
15111512γ-Cadinene0.70.10.1
15161518δ-Cadinene2.50.50.5
15211521Zonarene0.1trtr
15351538α-Cadinene0.1trtr
15621560Dodecanoic acid0.3-0.4
15761576Spathulenol1.80.30.4
15921593Ethyl laurate0.2--
161416141,10-di-epi-Cubenol0.1tr-
16251624Muurola-4,10(14)-dien-1β-ol0.1--
162616281-epi-Cubenol0.40.10.1
16411640τ-Cadinol2.30.60.4
16441644τ-Muurolol2.80.71.1
16461643α-Muurolol (=δ-Cadinol)1.20.3-
16561655α-Cadinol8.32.01.9
18141817Hexadecanal0.2--
19161923Cembrene-tr0.1
19881989Manoyl oxide0.20.1-
20372038Thunbergol A0.2-0.2
22252245Palustral0.40.10.1
Monoterpene hydrocarbons60.187.485.0
Oxygenated monoterpenoids5.23.95.9
Sesquiterpene hydrocarbons10.71.61.5
Oxygenated sesquiterpenoids16.94.03.9
Diterpenoids0.70.20.3
Benzenoid aromatics1.00.70.2
Others4.92.13.0
Total identified99.699.999.9
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a ZB-5ms column [24]. RIdb = Retention index values obtained from the databases [25,26,27,28]. UT = Utah. Percentages were determined based on peak areas.
Table 4. Leaf essential oil compositions (percentages) of Pinus lambertiana from northern California.
Table 4. Leaf essential oil compositions (percentages) of Pinus lambertiana from northern California.
RIcalcRIdbCompoundsP.lamb. #1P.lamb. #2P.lamb. #3P.lamb. #4
800801Hexanal0.1trtrtr
830831Furfuraltr0.1trtr
849849(2E)-Hexenal0.30.20.20.1
852853(3Z)-Hexenol---0.1
857---3-Methyl-3-butenoic acid0.10.40.1tr
8798783-Methyl-2-butenoid acid (=Crotonic acid)0.10.30.10.1
923923Tricyclene0.10.10.2tr
925925α-Thujenetrtrtrtr
933933α-Pinene13.214.520.311.4
947948α-Fenchenetrtr0.1tr
949950Camphene1.21.41.60.3
953953Thuja-2,4(10)-dienetrtrtrtr
972972Sabinene0.20.10.10.1
978978β-Pinene41.536.746.428.9
989989Myrcene1.71.81.81.0
10051004p-Mentha-1(7),8-dienetrtrtrtr
10071007α-Phellandrene0.10.10.10.1
10091009δ-3-Carene0.10.50.10.2
101510151,4-Cineoletrtr0.1tr
10171017α-Terpinene0.10.10.20.1
10251025p-Cymenetrtr0.1tr
10291030Limonene2.52.73.21.6
10311031β-Phellandrene3.11.62.32.3
10351034(Z)-β-Ocimenetrtrtrtr
10441045Phenylacetaldehydetrtrtrtr
10461046(E)-β-Ocimene0.2trtrtr
10581058γ-Terpinene0.10.10.30.1
10701069cis-Linalool oxide (furanoid)--trtr
10721072Pinoltrtr0.10.1
10851086Terpinolene1.01.31.40.6
10901091p-Cymenene-0.10.1tr
11001101Linalool--0.20.1
11001100Undecane0.20.2-0.1
11051104Nonanaltrtrtrtr
11191120endo-Fencholtr-tr-
11251124cis-p-Menth-2-en-1-oltrtrtrtr
11271127α-Campholenal0.10.30.1tr
11301131Terpin-3-en-1-oltrtrtrtr
11381137Nopinonetrtrtrtr
11561156Camphene hydrate0.10.10.10.1
11601160trans-Pinocamphonetrtr0.1tr
11631164Pinocarvonetrtrtrtr
11721171p-Mentha-1,5-dien-8-oltrtr0.10.1
11771176cis-Pinocamphonetr0.1tr0.1
11811180Terpinen-4-ol0.20.10.40.1
11881188p-Cymen-8-oltrtrtrtr
11961195α-Terpineol5.14.26.92.6
11981198Methyl chavicol (=Estragole)tr-1.10.3
12071206Decanaltrtrtrtr
12291229Thymyl methyl ethertrtr--
12521252Chavicol-0.10.1-
129212932-Undecanonetrtr--
13001300Tridecane0.20.1-0.1
13321330Bicycloelemene--trtr
13351335δ-Elemene--0.20.1
13471348α-Cubebenetrtrtrtr
13501348α-Longipinenetr--tr
13691370α-Ylangenetrtrtrtr
13761375α-Copaene0.10.1tr0.2
13841385β-Bourbonene0.10.30.10.1
13871385α-Bourbonene-trtr-
13881387β-Cubebenetrtrtrtr
13891390trans-β-Elemene0.10.30.10.3
14091411Longifolene0.1tr0.10.4
14101410Dodecanal0.20.10.10.2
14191417(E)-β Caryophyllene10.010.12.516.6
14301430β-Copaene0.10.20.10.1
14401440(Z)-β-Farnesene-0.1-0.1
14411442Guaia-6,9-diene--trtr
14491450trans-Muurola-3,5-dienetrtr--
14521452(E)-β-Farnesenetr0.10.10.1
14551454α-Humulene1.71.70.42.9
14621463cis-Muurola-4(14),5-dienetrtr-0.1
146814679-epi-(E)-Caryophyllenetr0.1tr0.1
14721472cis-Cadina-1(6),4-diene0.1trtr0.1
14751475γ-Muurolene0.30.40.20.5
14811480Germacrene D4.413.04.89.4
14891490Prenyl benzoate0.10.1tr-
14891490Aristolochene---0.1
14911492trans-Muurola-4(14),5-diene0.10.1tr0.1
14951497Bicyclogermacrenetr--0.1
149514952-Tridecanone-trtr-
14961501epi-Zonarene0.1---
14961497α-Selinene-trtr0.1
14981500α-Muurolene0.60.30.10.9
15021503β-Himachalenetr0.1trtr
15031504(E,E)-α-Farnesenetr0.10.10.1
15101511(Z)-γ-Bisabolene-0.1-0.1
15141514γ-Cadinene0.80.30.11.0
15181518δ-Cadinene2.91.00.33.9
15231521Zonarene0.1trtr0.1
15331533trans-Cadine-1,4-diene0.1trtr0.1
15371538α-Cadinene0.1trtr0.2
15411541(E)-α-Bisabolene-tr0.50.2
15611560Dodecanoic acid0.10.2tr0.1
15621561(E)-Nerolidol0.20.30.60.2
15781574Germacra-1(10),5-dien-4β-ol 0.40.1tr0.7
15831587Caryophyllene oxide0.20.20.10.4
16101611Humulene epoxide IItrtrtrtr
161616161,10-di-epi-Cubenol---0.1
162816281-epi-Cubenol0.1trtr0.1
16321629iso-Spathulenol--0.1-
16431643τ-Cadinol0.70.20.10.9
16451645τ-Muurolol1.00.20.11.4
16481651α-Muurolol (=δ-Cadinol)0.50.20.10.6
16571655α-Cadinol3.00.80.33.9
18171817Hexadecanal0.10.20.10.1
18321832(2E,6E)-Farnesyl acetate--0.3tr
19221930Cembrene0.10.1tr0.1
19641966Pimaradiene-0.4tr1.1
19871997(Z)-9,17-Octadecadienal-0.1trtr
19921989Manoyl oxidetr0.10.10.1
19941995(9Z)-Octadecenal-0.20.1tr
199620009β-iso-Pimara-7,15-diene--0.10.1
20102012Verticilla 4(20),7,11-trienetrtrtr0.1
2013200718-Norabieta-8,11,13-triene--0.10.1
20532053Manool-0.20.10.1
20842086Abietadienetrtrtrtr
21812180Sandaracopimarinal-0.4tr1.1
22212204iso-Pimarinal--0.10.1
22292243Palustral0.10.10.10.1
22332265Levopimarinaltrtrtrtr
22452257Methyl sandaracopimarate-0.2tr0.1
22612266Dehydroabietaltrtrtrtr
23062312Abietaltrtrtrtr
23122325Methyl daniellate0.20.20.10.1
Monoterpene hydrocarbons65.061.178.246.6
Oxygenated monoterpenoids5.44.88.13.0
Sesquiterpene hydrocarbons21.728.39.638.1
Oxygenated sesquiterpenoids6.12.01.68.1
Diterpenoids0.41.50.73.1
Benzenoid aromatics0.10.21.20.3
Others1.32.20.70.8
Total identified100.0100.099.999.9
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a ZB-5ms column [24]. RIdb = Retention index values obtained from the databases [25,26,27,28]. Percentages were determined based on peak areas.
Table 5. Leaf essential oil compositions (percentages) of Pinus monticola from Mt. St. Helens, Washington, and Priest Lake, Idaho.
Table 5. Leaf essential oil compositions (percentages) of Pinus monticola from Mt. St. Helens, Washington, and Priest Lake, Idaho.
RIcalcRIdbCompoundsP. mont. WA#1P. mont.WA#2P. mont. WA#3P. mont.ID#1P. mont.ID#2P. mont.ID#3
799797(3Z)-Hexenal0.10.10.1tr0.1tr
800801Hexanal0.20.20.10.10.10.1
848849(2E)-Hexenal2.92.82.81.42.71.3
850853(3Z)-Hexenol0.1-0.1-0.10.1
860860Tiglic acid--0.1---
8838833-Methyl-2-butenoic acid0.1----0.2
896904Angelic acid-0.40.5---
923923Tricyclene0.10.10.10.10.10.1
925925α-Thujene0.10.1trtrtrtr
933932α-Pinene15.712.114.49.812.311.3
947948α-Fenchene0.10.10.10.10.10.1
949950Camphene2.01.31.40.91.11.2
973971Sabinene0.30.40.30.20.20.3
978978β-Pinene21.218.724.123.125.616.7
990989Myrcene4.94.54.44.64.33.9
10071006α-Phellandrene2.40.41.40.30.50.7
10101008δ-3-Carene10.810.68.212.910.312.6
10171018α-Terpinene0.40.10.2tr0.10.1
10251025p-Cymene0.31.30.61.30.90.6
10311030Limonene6.56.18.26.35.23.7
10321031β-Phellandrene6.24.25.03.94.03.4
10351034(Z)-β-Ocimenetrtrtrtrtrtr
103810412-Heptyl acetate0.1trtrtrtrtr
10461045(E)-β-Ocimenetrtrtrtrtrtr
10581057γ-Terpinene0.60.10.30.10.10.2
10811082p-Mentha-2,4(8)-diene0.1tr0.10.10.10.1
10851086Terpinolene3.51.42.61.31.61.6
10901091p-Cymenenetrtrtr0.1trtr
109010902-Nonanonetr0.1tr0.1trtr
10991097α-Pinene oxide--0.10.10.1tr
11001101Linalool---0.10.1tr
11051104Nonanaltrtrtrtrtrtr
11071105α-Thujone0.1tr----
11191120endo-Fenchol----0.1-
11241124cis-p-Menth-2-en-1-ol0.20.20.20.20.10.1
11271127α-Campholenal0.10.1---tr
11321132cis-Limonene oxide-tr-0.1trtr
11381139Nopinone-tr-trtrtr
11421142trans-p-Menth-2-en-1-ol0.20.40.20.40.30.1
11471145Camphor0.1-----
11551156Camphene hydrate0.10.20.20.40.20.1
11601160trans-Pinocamphone0.10.20.10.20.10.1
11621164Pinocarvone---0.1trtr
11771176cis-Pinocamphone----0.1-
11821180Terpinen-4-ol0.71.00.71.00.70.4
11851184p-Methylacetophenone-0.1tr0.10.1tr
11881185Cryptone-0.40.10.40.1tr
11891186p-Cymen-8-ol0.10.40.20.60.40.2
11981195α-Terpineol4.16.15.27.87.72.1
12761274Cyclooctyl acetate0.10.1tr0.10.1tr
12851285Bornyl acetate2.92.61.41.71.11.6
129312932-Undecanone0.50.30.20.50.30.2
13471346α-Terpinyl acetate0.10.10.10.10.10.1
13501349Citronellyl acetatetr0.1tr0.20.10.1
13581361Neryl acetate0.10.10.10.20.1tr
135813572-Methylundecanaltr----tr
13631366Linalyl isobutyrate-0.2-0.30.1tr
13781378Geranyl acetate0.10.2tr0.30.40.1
13831383cis-β-Elemene0.10.1trtrtr1.0
13841382β-Bourbonene-----0.1
13901390trans-β-Elemene1.81.51.10.90.715.2
139413932-Dodecanone0.1trtr0.1trtr
14181422β-Ylangene-----0.1
14191417(E)-β-Caryophyllene0.60.20.10.10.10.3
14451451Prenyl benzoate-0.1tr---
14531452(E)-β-Farnesenetrtrtr--0.1
14561454α-Humulene0.1trtr--0.1
14621458allo-Aromadendrene-----0.1
14731475Selina-4,11-diene0.10.20.10.10.10.7
14751478γ-Muurolene-0.10.10.1tr0.1
14811480Germacrene D0.30.10.10.10.13.6
14891487β-Selinene0.40.40.30.30.22.0
14921492trans-Muurola-4(14),5-diene-trtr--0.1
149514942-Tridecanone0.30.20.10.20.20.4
14951497α-Selinene0.20.20.20.10.11.5
14981500α-Muurolenetr0.20.10.20.20.3
15071508β-Bisabolene0.20.10.10.10.1-
15071504Germacrene A-----0.5
15131512γ-Cadinene0.10.20.10.20.10.4
15181518δ-Cadinene0.20.80.60.60.61.4
15211519trans-Calamenene-0.1tr---
15221521Zonarene-trtr---
15371538α-Cadinene0.1-tr--0.1
15631560Dodecanoic acid (=Lauric acid)0.20.30.30.20.10.3
15771574Germacra-1(10),5-dien-4β-ol-----0.1
15771578Spathulenol-0.10.2-0.2-
15811587Caryophyllene oxide0.10.1tr---
15931593Ethyl laurate--0.1---
161516141,10-di-epi-Cubenol-0.10.10.10.1-
162716281-epi-Cubenol-0.20.20.30.2-
16391644allo-Aromadendrene epoxide-----0.2
16431643τ-Cadinol0.32.01.41.61.80.6
16451644τ-Muurolol0.42.41.82.32.30.9
16471651α-Muurolol (=δ-Cadinol)0.21.00.90.91.20.3
16511650Pogostol-0.2---0.4
16571655α-Cadinol0.77.45.16.66.92.2
16601660Selin-11-en-4α-ol1.51.31.41.31.32.6
16621661neo-Intermedeol0.30.40.20.30.20.2
16871688α-Bisabolol0.60.20.30.10.1-
17581758Myristic acid--0.1---
18161817Hexadecanal0.1-tr---
19581958Palmitic acid-0.20.10.10.1-
19911989Manoyl oxide0.20.10.10.10.10.1
20092012Verticilla 4(20),7,11-triene0.10.1tr---
21462143Serratol0.1-0.1---
21802180Sandaracopimarinal0.10.10.1-0.1-
2209---(1R,4aR,5S)-5-((E)-5-Methoxy-3-methylpent-3-en-1-yl)-1,4a-dimethyl-6-methylenedecahydro-naphthalene-1-carbaldehyde a0.10.2----
22282245Palustrinal0.50.20.40.10.10.2
22602266Dehydroabietal0.10.30.10.20.10.1
22942302Methyl levopimarate0.2-----
23052312Abietal0.1-----
2317---15-Beyeren-19-yl acetate b1.1-----
23292324Methyl dehydroabietate0.1trtr--0.3
Monoterpene hydrocarbons75.261.471.264.966.456.4
Oxygenated monoterpenoids9.011.88.513.811.94.9
Sesquiterpene hydrocarbons4.34.12.92.62.227.4
Oxygenated sesquiterpenoids4.115.411.513.514.37.5
Diterpenoids2.61.00.80.30.40.6
Benzenoid aromatics0.00.1tr0.10.1tr
Others4.74.84.73.33.92.7
Total identified99.898.899.598.699.299.5
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a ZB-5ms column [24]. RIdb = Retention index values obtained from the databases [25,26,27,28]. a A reference RI value was not available, but the MS showed an 85% match. b A reference RI value was not available, but the MS showed a 94% match. WA = Washington. ID = Idaho. Percentages were determined based on peak areas.
Table 6. Leaf essential oil compositions (percentages) of Pinus sabiniana collected in Paradise, California.
Table 6. Leaf essential oil compositions (percentages) of Pinus sabiniana collected in Paradise, California.
RIcalcRIdbCompoundsP.sab. #1P.sab. #2P.sab. #3
783773Prenol0.10.1tr
801801Hexanal0.1trtr
831831Furfural0.10.10.1
851850(2E)-Hexenal-tr0.1
851853(3Z)-Hexenol0.10.10.1
923923Tricyclene0.10.1tr
925925α-Thujenetrtrtr
933933α-Pinene65.061.215.8
948948α-Fenchenetrtrtr
949950Camphene1.11.00.2
953953Thuja-2,4(10)-diene0.1trtr
961960Benzaldehydetrtrtr
972972Sabinenetrtrtr
978978β-Pinene6.66.62.0
9849846-Methyl-5-hepten-2-onetrtrtr
989989Myrcene3.84.95.7
10041005Octanaltr0.10.3
100610063-Ethenyl-1,2-dimethylcyclohexa-1,4-dienetrtrtr
10071007α-Phellandrene0.10.1tr
10091009δ-3-Carenetrtrtr
10171018α-Terpinenetrtrtr
10261025p-Cymene0.10.10.1
10291030Limonene1.51.454.9
10311031β-Phellandrene1.71.70.3
10351035(Z)-β-Ocimene7.911.39.6
10431043Phenylacetaldehydetrtrtr
10451045(E)-β-Ocimene0.50.60.6
10581058γ-Terpinene0.1trtr
10721072Pinoltrtrtr
10851086Terpinolene0.50.40.2
10891091p-Cymenenetr-tr
10921091Rosefuran-tr-
10981097α-Pinene oxide0.1tr-
11001101Linalool-0.10.1
11001100Undecane0.1--
11041104Nonanal0.10.10.1
11181119endo-Fencholtrtrtr
11221122trans-p-Mentha-2,8-dien-1-ol--tr
11271127α-Campholenal0.20.1tr
11281128(4E,6Z)-allo-Ocimene0.30.40.3
11361137cis-p-Mentha-2,8-dien-1-ol--tr
11381139Nopinonetrtr-
11401141trans-Pinocarveol0.10.1-
11461145Camphortrtr-
11521152Citronellal--0.1
11541156Camphene hydrate0.1tr-
11591160trans-Pinocamphone0.10.1-
11621164Pinocarvone0.10.1tr
11711171p-Mentha-1,5-dien-8-ol0.30.2tr
11751176cis-Pinocamphonetr0.1-
11751177(3E,5Z)-Undeca-1,3,5-triene0.30.80.4
11801180Terpinen-4-ol0.10.1tr
11851185(3E,5E)-Undeca-1,3,5-triene0.10.10.1
11861186p-Cymen-8-ol0.1tr-
11951195α-Terpineol3.11.60.4
11971197Methyl chavicol (=Estragole)0.60.93.5
12061206Decanal0.30.50.8
12071208Verbenone0.20.1-
12291229Thymyl methyl ether-tr-
12441246Carvone--0.1
12541254Phenylethyl acetate--tr
13511356Eugenol--tr
13891390trans-β-Elemene0.20.30.1
13991403Methyl eugenol-0.1tr
14091410Dodecanal0.60.50.5
14181417(E)-β-Caryophyllene0.20.20.4
143614372-Phenylethyl butanoate0.6--
14461447Geranylacetone0.1trtr
14521452(E)-β-Farnesene0.10.1tr
14541454α-Humulene--0.1
14801480Germacrene D0.10.20.1
14881487β-Selinenetr0.10.1
14891489(Z,E)-α-Farnesenetrtrtr
14951497α-Selinene0.10.10.1
15031503(E,E)-α-Farnesene0.10.30.1
15171518δ-Cadinenetr0.1tr
15601560Dodecanoic acid0.40.10.1
15601560(E)-Nerolidol-0.10.3
16371639Phenylethyl hexanoate0.1--
16551655α-Cadinol0.20.1tr
17661769Benzyl benzoate-tr0.2
18161817Hexadecanaltrtrtr
18541856Phenylethyl benzoate0.20.4tr
19931994Manoyl oxide0.30.40.5
2009200718-nor-Abieta-8,11,13-triene0.10.10.1
2010---Biformene a--0.1
21462147(Z)-Abienol0.10.2tr
21782180Sandaracopimarinaltr--
22272245Palustral0.10.10.1
22322265Levopimarinaltr0.1tr
22462257Methyl sandaracopimarate--0.1
22912297Methyl isopimarate--tr
22962302Methyl levopimarate0.1tr0.1
23302350(1R,4aR,5S)-5-[(E)-5-Hydroxy-3-methylpent-3-enyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carbaldehyde1.01.21.0
23652366Neoabietic acid 0.10.20.1
24282441Methyl neoabietate0.1tr0.1
Monoterpene hydrocarbons88.989.389.3
Oxygenated monoterpenoids4.53.01.1
Sesquiterpene hydrocarbons0.61.30.9
Oxygenated sesquiterpenoids0.20.20.3
Diterpenoids0.80.91.0
Benzenoid aromatics1.51.33.6
Others2.12.42.5
Total identified99.699.699.8
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a ZB-5ms column [24]. RIdb = Retention index values obtained from the databases [25,26,27,28]. a A reference RI value was not available, but the MS showed an 86% match. Percentages were determined based on peak areas.
Table 7. Enantiomeric distribution of chiral monoterpenoids in Pinus albicaulis.
Table 7. Enantiomeric distribution of chiral monoterpenoids in Pinus albicaulis.
EnantiomersRIcalcRIdbWY#1WY#2CA#1CA#2
(+)-α-Thujenen.d.9500.00.00.00.0
(−)-α-Thujene952951100.0100.0100.0100.0
(−)-α-Pinene97497694.485.080.286.4
(+)-α-Pinene9809825.615.019.813.6
(−)-Camphene100199897.997.396.097.0
(+)-Camphene100610052.12.74.03.0
(+)-Sabinene102210213.27.08.74.2
(−)-Sabinene1030103096.893.091.395.8
(+)-β-Pinene102710276.35.99.77.9
(−)-β-Pinene1031103193.794.190.392.1
(+)-δ-3-Carene10491052100.0100.0100.0100.0
(−)-δ-3-Carenen.d.n.a.0.00.00.00.0
(−)-Limonene1074107396.093.985.087.4
(+)-Limonene108110814.06.115.012.6
(−)-β-Phellandrene1083108398.595.559.671.3
(+)-β-Phellandrene108610891.54.540.428.7
(+)-Terpinen-4-ol1295129727.429.630.529.1
(−)-Terpinen-4-ol1298130072.670.469.570.9
(−)-α-Terpineol13491347-80.085.784.3
(+)-α-Terpineol13581356-20.014.315.7
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a B-Dex 325 chiral capillary column. RIdb = Retention index values obtained from our own database using available reference compounds. n.d. = Compound not detected. n.a. = Reference compound not available. Percentages were determined based on peak areas.
Table 8. Enantiomeric distribution of chiral monoterpenoids in Pinus flexilis.
Table 8. Enantiomeric distribution of chiral monoterpenoids in Pinus flexilis.
EnantiomersRIcalcRIdbP.flex. UT#1P.flex. UT#2P.flex. UT#3
(+)-α-Thujenen.d.9500.00.0-
(−)-α-Thujene952951100.0100.0-
(−)-α-Pinene97497627.831.225.1
(+)-α-Pinene98098272.268.874.9
(−)-Camphene100199888.593.170.8
(+)-Camphene1006100511.56.929.2
(+)-Sabinene102210211.6--
(−)-Sabinene1030103098.4--
(+)-β-Pinene102710272.92.01.6
(−)-β-Pinene1031103197.198.098.4
(+)-δ-3-Carene10491052-100.0100.0
(−)-δ-3-Carenen.d.n.a.-0.00.0
(−)-Limonene1074107392.369.267.0
(+)-Limonene108110817.730.833.0
(−)-β-Phellandrene1083108398.798.299.0
(+)-β-Phellandrene108610891.31.81.0
(+)-Terpinen-4-ol1295129726.531.429.7
(−)-Terpinen-4-ol1298130073.568.670.3
(−)-α-Terpineol1349134767.385.593.6
(+)-α-Terpineol1358135632.714.56.4
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a B-Dex 325 chiral capillary column. RIdb = Retention index values obtained from our own database using available reference compounds. n.d. = Compound not detected. n.a. = Reference compound not available. Percentages were determined based on peak areas.
Table 9. Enantiomeric distribution of chiral monoterpenoids in Pinus lambertiana.
Table 9. Enantiomeric distribution of chiral monoterpenoids in Pinus lambertiana.
EnantiomersRIcalcRIdbP.lamb. #1P.lamb. #2P.lamb. #3P.lamb. #4
(−)-α-Pinene97597668.871.561.761.0
(+)-α-Pinene98298231.228.538.339.0
(−)-Camphene100299893.793.790.981.2
(+)-Camphene100710056.36.39.118.8
(+)-β-Pinene102610271.81.81.81.7
(−)-β-Pinene1027103198.298.298.298.3
(−)-Limonene1075107370.271.562.666.8
(+)-Limonene1081108129.828.537.433.2
(−)-β-Phellandrene1083108398.998.198.598.7
(+)-β-Phellandrene108810891.11.91.51.3
(+)-Terpinen-4-ol1293129735.239.942.338.1
(−)-Terpinen-4-ol1296130064.864.157.761.9
(−)-α-Terpineol1345134795.595.493.794.4
(+)-α-Terpineol135713564.54.66.35.6
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a B-Dex 325 chiral capillary column. RIdb = Retention index values obtained from our own database using available reference compounds. Percentages were determined based on peak areas.
Table 10. Enantiomeric distribution of chiral monoterpenoids in Pinus monticola.
Table 10. Enantiomeric distribution of chiral monoterpenoids in Pinus monticola.
EnantiomersRIcalcRIdbWA#1WA#2WA#3ID#1ID#2ID#3
(−)-α-Pinene97597663.162.361.359.267.763.2
(+)-α-Pinene98198236.937.738.740.832.336.8
(−)-Camphene100299894.692.691.990.292.194.1
(+)-Camphene100710055.47.48.19.87.95.9
(+)-β-Pinene102610274.44.33.73.33.23.9
(−)-β-Pinene1027103195.695.796.396.796.896.1
(+)-δ-3-Carene10491052100.0100.0100.0100.0100.0100.0
(−)-δ-3-Carenen.d.n.a.0.00.00.00.00.00.0
(−)-α-Phellandrenen.d.10500.00.00.00.00.00.0
(+)-α-Phellandrene10541053100.0100.0100.0100.0100.0100.0
(−)-Limonene1075107346.742.060.543.544.541.2
(+)-Limonene1081108153.358.039.556.555.558.8
(−)-β-Phellandrene1084108347.442.348.044.952.851.4
(+)-β-Phellandrene1088108952.657.752.055.147.248.6
(+)-Terpinen-4-ol1300129745.140.340.840.740.939.1
(−)-Terpinen-4-ol1303130054.959.759.259.359.160.9
(−)-Borneol13361335100.0100.0100.0100.0100.0100.0
(+)-Borneoln.d.13400.00.00.00.00.00.0
(−)-α-Terpineol1344134789.789.690.591.892.789.5
(+)-α-Terpineol1354135610.310.49.58.27.310.5
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a B-Dex 325 chiral capillary column. RIdb = Retention index values obtained from our own database using available reference compounds. n.d. = Compound not detected. n.a. = Reference compound not available. Percentages were determined based on peak areas.
Table 11. Enantiomeric distribution of chiral monoterpenoids in Pinus sabiniana.
Table 11. Enantiomeric distribution of chiral monoterpenoids in Pinus sabiniana.
EnantiomersRIcalcRIdbP.sab. #1P.sab. #2P.sab. #3
(−)-α-Pinene97597690.693.067.4
(+)-α-Pinene9839829.47.032.6
(−)-Camphene100199888.289.776.4
(+)-Camphene1005100511.810.323.6
(+)-β-Pinene102610277.06.88.1
(−)-β-Pinene1030103193.093.291.9
(−)-Limonene1073107344.245.498.8
(+)-Limonene1082108155.854.61.2
(−)-β-Phellandrene10851083100.0100.0100.0
(+)-β-Phellandrenen.d.10890.00.00.0
(−)-α-Terpineol1347134788.388.277.1
(+)-α-Terpineol1356135611.711.822.9
RIcalc = The calculated retention index determined with respect to a homologous series of n-alkanes on a B-Dex 325 chiral capillary column. RIdb = Retention index values obtained from our own database using available reference compounds. n.d. = Compound not detected. Percentages were determined based on peak areas.
Table 12. Collection and hydrodistillation details for Pinus species (P. albicaulis, P. flexilis, P. lambertiana, P. monticola, and P. sabiniana).
Table 12. Collection and hydrodistillation details for Pinus species (P. albicaulis, P. flexilis, P. lambertiana, P. monticola, and P. sabiniana).
SampleVoucherCollection DateCollection LocationMass Leaves (g)Mass Essential Oil (g)% Yield
Pinus albicaulis WY#1WNS-Palb-067118 July 202444°56′59″ N, 109°37′60″ W, 2901 m asl150.905.29363.508
Pinus albicaulis WY#2 18 July 202444°56′59″ N, 109°37′59″ W, 2909 m asl178.165.26392.955
Pinus albicaulis CA#1WNS-Palb-543124 October 202440°28′32″ N, 121°28′53″ W, 2478 m asl122.094.19843.439
Pinus albicaulis CA#2 24 October 202440°28′32″ N, 121°28′53″ W, 2478 m asl140.824.89433.476
Pinus flexilis UT#1WNS-Pflex-803313 September 202337°36′56″ N, 112°10′16″ W, 2492 m asl43.571.96584.512
Pinus flexilis UT#2 13 September 202337°36′56″ N, 112°10′16″ W, 2492 m asl92.133.67713.991
Pinus flexilis UT#3 13 September 202337°36′56″ N, 112°10′16″ W, 2492 m asl42.022.11045.022
Pinus lambertiana CA#1 26 August 202440°01′10″ N, 121°31′59″ W, 1597 m asl148.433.29782.222
Pinus lambertiana CA#2 26 August 202440°01′12″ N, 121°31′56″ W, 1607 m asl107.512.36742.202
Pinus lambertiana CA#3 26 August 202440°01′07″ N, 121°32′01″ W, 1598 m asl114.762.30392.008
Pinus lambertiana CA#4WNS-Plamb-540326 August 202440°06′28″ N, 121°35′03″ W, 1281 m asl120.582.72952.264
Pinus monticola WA#1WNS-Pmont-033830 June 202446°09′37″ N, 122°05′42″ W, 897 m asl72.931.42181.950
Pinus monticola WA#2 30 June 202446°09′38″ N, 122°05′42″ W, 888 m asl93.101.51311.625
Pinus monticola WA#3 30 June 202446°09′42″ N, 122°05′51″ W, 892 m asl122.432.48822.032
Pinus monticola ID#1WNS-Pmont-074619 August 202448°33′41″ N, 116°47′56″ W, 1086 m asl97.011.27601.315
Pinus monticola ID#2 19 August 202448°33′37″ N, 116°48′06″ W, 1089 m asl113.741.94081.706
Pinus monticola ID#3 19 August 202448°33′28″ N, 116°48′20″ W, 1064 m asl120.662.29881.905
Pinus sabiniana #1WNS-Psab-54381 September 202439°42′57″ N, 121°43′17″ W, 98 m asl134.793.30302.450
Pinus sabiniana #2 1 September 202439°44′39″ N, 121°40′28″ W, 168 m asl120.682.86082.371
Pinus sabiniana #3 1 September 202439°44′35″ N, 121°39′20″ W, 421 m asl162.753.79482.332
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MDPI and ACS Style

Moore, A.; Ankney, E.; Swor, K.; Poudel, A.; Satyal, P.; Setzer, W.N. Leaf Essential Oil Compositions and Enantiomeric Distributions of Monoterpenoids in Pinus Species: Pinus albicaulis, Pinus flexilis, Pinus lambertiana, Pinus monticola, and Pinus sabiniana. Molecules 2025, 30, 244. https://doi.org/10.3390/molecules30020244

AMA Style

Moore A, Ankney E, Swor K, Poudel A, Satyal P, Setzer WN. Leaf Essential Oil Compositions and Enantiomeric Distributions of Monoterpenoids in Pinus Species: Pinus albicaulis, Pinus flexilis, Pinus lambertiana, Pinus monticola, and Pinus sabiniana. Molecules. 2025; 30(2):244. https://doi.org/10.3390/molecules30020244

Chicago/Turabian Style

Moore, Alicia, Elizabeth Ankney, Kathy Swor, Ambika Poudel, Prabodh Satyal, and William N. Setzer. 2025. "Leaf Essential Oil Compositions and Enantiomeric Distributions of Monoterpenoids in Pinus Species: Pinus albicaulis, Pinus flexilis, Pinus lambertiana, Pinus monticola, and Pinus sabiniana" Molecules 30, no. 2: 244. https://doi.org/10.3390/molecules30020244

APA Style

Moore, A., Ankney, E., Swor, K., Poudel, A., Satyal, P., & Setzer, W. N. (2025). Leaf Essential Oil Compositions and Enantiomeric Distributions of Monoterpenoids in Pinus Species: Pinus albicaulis, Pinus flexilis, Pinus lambertiana, Pinus monticola, and Pinus sabiniana. Molecules, 30(2), 244. https://doi.org/10.3390/molecules30020244

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