Sage Journals: Discover world-class research

Abstract

Background/Objective: Larix occidentalis (Pinaceae) is a tree native to the mountains of northwestern United States and southwestern Canada. Indigenous peoples used this tree as part of their traditional medicine to treat various ailments, including coughs, colds, arthritis, and wounds. As part of our interest in essential oils of coniferous tree species and the potential utilization as fragrances, we have obtained the foliar essential oil of L. occidentalis from Idaho, USA, which complements previous reports from Canada. Methods: The foliage from three individual trees growing on Brundage Mountain, Idaho, were collected; the essential oils obtained by hydrodistillation, and the essential oils characterized by gas chromatographic methods, including enantioselective gas chromatography – mass spectrometry. Results: The yellow essential oils were obtained in yields of 1.25-1.77%. The major components in the essential oils were α-pinene (26.5 ± 5.4%), β-pinene (14.9 ± 2.5%), α-terpineol (8.3 ± 1.2%), and δ-3-carene (6.6 ± 2.9%). The (−)-enantiomers were dominant for camphene (84.1 ± 6.6%), β-pinene (97.7 ± 0.4%), β-phellandrene (80.6 ± 3.2%), borneol (86.2 ± 0.9%), and α-terpineol (85.4 ± 4.6%); the (+)-enantiomer was the only enantiomer observed for δ-3-carene. Conclusions: This is the first investigation of L. occidentalis essential oil from Idaho. The major components are consistent with ethnopharmacological uses of the plant. Additional work is needed to more clearly define the essential oil compositions of North American, European, and Asian Larix species.

Keywords

Western larch chemical composition gas chromatography enantioselective chiral monoterpenoids

Introduction

Larix occidentalis Nutt. (western larch, Pinaceae) is found naturally in the mountains of southwestern Canada (Alberta and British Columbia) and northwestern United States (Idaho, Montana, Oregon, and Washington) (Figure 1). The tree grows up to 50 m in height; the leaves (needles) are 2-5 cm long and 0.6-0.8 mm wide; the bark is reddish brown, scaly, with deep furrows between flat, flaky, cinnamon-colored plates; the seed cones are 2-3 cm × 1.3-1.6 cm (Figure 2).¹

Figure 1.

Range of Larix occidentalis Nutt.²

Figure 2.

Larix occidentalis Nutt. A: Branches with Leaves (Needles) and Seed Cones. B: Bark. C: Scan of Pressed Plant Material.

Several Native American tribes used L. occidentalis as part of their traditional herbal medicine.³ The Nez Perce Native Americans used infusions of the bark of L. occidentalis to treat coughs and colds.³ The Okanagan-Colville people used a decoction of the plant (both externally and internally) treat arthritis and externally to wash cuts and sores.³ The Thompson people used a decoction of the branches to treat coughs.³ Similarly, Larix decidua (L.) Mill. has been used in traditional herbal medicine in Europe to treat the common cold,^4,5 coughs,⁶ wounds,^7,8 and sore joints.⁹

Essential oils are complex mixtures of volatile, hydrophobic compounds that are typically obtained by hydrodistillation or steam distillation of plant materials, but may also be obtained by cold pressing or enfleurage.¹⁰ The compositions of essential oils are very complex and may contain more than 200 individual components. The compound classes making up essential oils are typically monoterpenoids, sesquiterpenoids, diterpenoids, fatty acid derivatives, and phenylpropanoids.^11,12 Essential oils have shown various biological activities including antibacterial, antifungal,¹³ allelopathic,¹⁴ and pesticidal.¹⁵ Due to these attributes, essential oils have demonstrated valuable applications in various fields including agriculture,¹⁶ the food industry,^17,18 the flavor and fragrance industry,¹⁹ cosmetics,²⁰ aromatherapy,²¹ and drug discovery.²² As part of our ongoing interest in aromatic and medicinal plants as well as gymnosperm essential oils, this report presents the essential oil composition and the enantiomeric distribution of chiral monoterpenoids of L. occidentalis growing in Idaho. This present work complements previous older examinations of L. occidentalis^23,24 and includes enantioselective gas chromatographic evaluation, which broadens our understanding of the volatile composition of this species.

Materials and Methods

Plant Material

Foliage of L. occidentialis was collected from three individual trees located on Brundage Mountain, Idaho, on 31 May 2024. Twigs from several sites on the tree were obtained and pooled for each individual tree. The trees were identified in the field by W.N. Setzer and confirmed by comparison with samples from the C.V. Starr Virtual Herbarium.²⁵ A voucher specimen (WNS-Locc-5826) was deposited with the University of Alabama in Huntsville herbarium. The plant material was stored frozen (–20 °C) until processing. The foliage was hydrodistilled for 4 h using a Likens-Nickerson apparatus as previously described²⁶ to give yellow essential oils (Table 1).

Table 1.

Collection and Hydrodistillation Details for Larix occidentalis Individual Trees.

Sample	Location	Mass Plant Material (g)	Mass Essential Oil (g)	% Yield
L. occidentalis A	45°00′39ʺ N, 116°09′09ʺ W, 1928 m asl	160.37	2.8441	1.773
L. occidentalis B	45°00′40ʺ N, 116°09′10ʺ W, 1926 m asl	149.30	2.0959	1.404
L. occidentalis C	45°01′03ʺ N, 116°08′57ʺ W, 1986 m asl	136.46	1.7097	1.253

Gas Chromatographic Analyses

The L. occidentalis foliar essential oils were subjected to gas chromatographic analyses (GC-FID, GC-MS, and enantioselective GC-MS) as previously described.²⁶ The chromatographic details are provided as Supplemental material (Supplemental Table S1).

Hierarchical Cluster Analysis

Hierarchical cluster analysis (HCA) was carried out using XLSTAT v. 2018.1.1.62926 (Addinsoft, Paris, France). The percentages of the fifteen most abundant components (α-pinene, camphene, sabinene, β-pinene, myrcene, δ-3-carene, limonene, β-phellandrene, 1,8-cineole, β-ocimene, terpinolene, α-terpineol, bornyl acetate, germacrene D, and (E)-nerolidol) from this study and the compositions from other Larix species previously reported^23,24,27-32 were used for the analysis. Dissimilarity was used to determine clusters considering Euclidean distance and Ward's method was used to define agglomeration.

Results

Essential Oil Composition

Foliage (terminal twigs and leaves) from three individual trees growing on Brundage Mountain, Idaho, were collected. Hydrodistillation of the foliage of L. occidentalis gave yellow essential oils in yields of 1.253-1.773% (Table 1). Gas chromatographic analysis of the essential oils allowed for identification of a total of 117 chemical components collected from three individual trees, which accounted for 98.2-99.6% of the total essential oil compositions (Table 2, Supplemental Figure S1). Monoterpene hydrocarbons (55.0-65.9%) and oxygenated monoterpenoids (17.0-24.1%) dominated the foliar essential oils of L. occidentalis. Sesquiterpene hydrocarbons (4.1-10.3%), oxygenated sesquiterpenoids (3.4-6.1%), and diterpenoids (2.3-3.6%) were minor constituents. The major components in the essential oils were α-pinene (26.5 ± 5.4%), β-pinene (14.9 ± 2.5%), α-terpineol (8.3 ± 1.2%), and δ-3-carene (6.6 ± 2.9%).

Table 2.

Chemical Composition (Percentage) of the Foliar Essential Oil of Larix occidentalis.

RI_calc	RI_db	Compounds	Tree A	Tree B	Tree C
922	923	Tricyclene	0.2	0.2	0.2
924	925	α-Thujene	0.1	0.1	0.1
932	932	α-Pinene	32.8	23.4	23.3
946	948	α-Fenchene	0.1	0.1	0.1
948	950	Camphene	2.0	1.7	1.0
952	953	Thuja-2,4(10)-diene	0.2	0.3	0.2
970	970	3,7,7-Trimethyl-1,3,5-cycloheptatriene	0.1	0.1	0.1
971	971	Sabinene	0.3	0.7	0.8
977	978	β-Pinene	17.1	12.1	15.6
988	989	Myrcene	2.1	2.4	2.7
990	990	Dehydro-1,8-cineole	0.1	0.2	0.1
1006	1006	3-Ethenyl-1,2-dimethylcyclohexa-1,4-diene	0.1	0.1	0.1
1007	1007	α-Phellandrene	0.2	0.2	0.2
1008	1009	δ-3-Carene	4.6	5.3	9.9
1017	1018	α-Terpinene	0.4	0.6	0.8
1025	1025	p-Cymene	0.5	0.9	0.9
1029	1030	Limonene	2.0	2.1	2.4
1030	1031	β-Phellandrene	0.8	0.7	1.0
1031	1032	1,8-Cineole	0.2	0.2	0.1
1034	1034	(Z)-β-Ocimene	0.2	0.4	0.3
1045	1045	(E)-β-Ocimene	tr	tr	tr
1057	1057	γ-Terpinene	0.5	1.0	1.3
1072	1072	Pinol	0.2	0.3	0.2
1084	1086	Terpinolene	1.6	2.3	2.3
1091	1093	p-Cymenene	0.2	0.4	0.3
1100	1101	Linalool	0.1	0.1	0.1
1120	1119	endo-Fenchol	0.3	0.3	0.3
1128	1127	α-Campholenal	0.3	0.4	0.3
1141	1141	Nopinone	0.2	0.4	0.4
1141	1141	trans-Pinocarveol	0.9	1.0	0.7
1148	1149	Camphor	0.1	0.1	0.1
1156	1156	Camphene hydrate	0.2	0.2	0.2
1160	1157	Sabina ketone	–	0.1	0.1
1162	1161	trans-Pinocamphone	0.1	0.2	0.1
1164	1164	Pinocarvone	0.4	0.5	0.6
1173	1171	p-Mentha-1,5-dien-8-ol	0.5	1.3	1.0
1173	1173	Borneol	0.5	0.5	0.2
1181	1180	Terpinen-4-ol	1.5	3.4	4.2
1189	1189	p-Cymen-8-ol	0.3	0.8	0.6
1196	1195	α-Terpineol	7.2	8.1	9.6
1200	1201	Estragol (= Methylchavicol)	–	0.2	–
1209	1208	Verbenone	0.7	1.5	1.0
1220	1218	trans-Carveol	0.1	0.2	0.1
1227	1228	Citronellol	–	0.1	0.2
1229	1229	Thymyl methyl ether	0.1	0.1	0.1
1245	1242	Cuminal	–	tr	tr
1246	1246	Carvone	tr	0.1	tr
1256	1254	Piperitone	tr	0.1	0.1
1275	1276	2,3-Pinanediol	tr	0.1	0.1
1278	1278	Perillaldehyde	tr	tr	tr
1280	1280	Phellandral	tr	0.1	0.1
1283	1282	Bornyl acetate	2.7	3.0	2.1
1295	1294	trans-Pinocarvyl acetate	0.1	0.1	0.1
1345	1346	α-Terpinyl acetate	0.1	0.5	0.6
1348	1349	Citronellyl acetate	0.1	0.2	0.4
1376	1375	α-Copaene	0.1	0.1	0.1
1380	1380	Geranyl acetate	0.1	0.2	0.2
1390	1390	trans-β-Elemene	0.3	0.3	0.2
1419	1417	(E)-β-Caryophyllene	2.0	2.0	0.5
1429	1430	γ-Elemene	–	–	0.1
1430	1430	β-Copaene	0.1	0.1	–
1453	1452	(E)-β-Farnesene	0.1	0.1	0.1
1456	1454	α-Humulene	0.3	0.6	0.2
1472	1472	trans-Cadina-1(6),4-diene	0.1	0.1	tr
1475	1475	γ-Muurolene	0.3	0.3	0.1
1479	1479	α-Amorphene	0.2	0.3	0.2
1482	1480	Germacrene D	3.7	3.1	1.2
1490	1489	β-Selinene	0.1	0.1	0.1
1492	1492	trans-Muurola-4(14),5-diene	0.1	0.1	tr
1496	1497	α-Selinene	0.2	0.2	0.1
1499	1497	α-Muurolene	0.3	0.4	0.2
1502	1504	epi-Zonarene	0.1	0.1	tr
1507	1508	β-Bisabolene	0.1	tr	tr
1509	1509	β-Curcumene	0.1	0.1	0.1
1513	1514	γ-Cadinene	0.3	0.5	0.2
1518	1518	δ-Cadinene	1.1	1.5	0.7
1523	1521	Zonarene	0.1	0.1	tr
1533	1533	trans-Cadina-1,4-diene	0.1	0.1	–
1537	1538	α-Cadinene	0.1	0.1	tr
1542	1541	α-Calacorene	0.1	tr	tr
1550	1551	Elemicin	0.1	0.2	0.1
1560	1560	Germacrene B	–	–	0.1
1561	1560	(E)-Nerolidol	0.1	0.2	0.1
1583	1587	Caryophyllene oxide	0.1	0.1	0.1
1611	1611	Humulene epoxide II	tr	0.1	0.1
1616	1616	1,10-di-epi-Cubenol	0.1	0.1	tr
1623	1623	Humulane-1,6-dien-3-ol	0.2	0.2	0.1
1625	1624	Selina-6-en-4β-ol	–	–	0.1
1629	1628	1-epi-Cubenol	0.2	0.1	tr
1643	1643	τ-Cadinol	0.3	0.6	0.3
1646	1644	τ-Muurolol	0.4	0.6	0.4
1648	1643	α-Muurolol	0.2	0.2	0.2
1657	1655	α-Cadinol	1.1	2.1	1.3
1660	1661	neo-Intermedeol	0.1	0.2	0.2
1671	1671	β-Bisabolol	0.1	0.2	0.2
1687	1686	epi-α-Bisabolol	0.2	0.1	0.1
1689	1688	α-Bisabolol	0.1	0.1	0.1
1710	1710	(E)-Apitone	-	0.2	-
1716	1714	(2E,6Z)-Farnesal	-	0.3	0.1
1720	1720	(2Z,6E)-Farnesal	-	0.2	0.2
1736	1735	Oplopanone	0.1	0.6	0.9
1922	1923	Cembrene	0.6	0.3	0.6
1937	1934	(3Z)-Cembrene A	0.1	0.1	0.1
1995	1994	Manoyl oxide	0.1	0.1	0.1
1999	2000	9β-Isopimara-7,15-diene	0.2	0.2	0.2
2012	2012	Verticilla 4(20),7,11-triene	0.1	0.1	0.1
2017	2007	18-Norabieta-8,11,13-triene	0.1	0.2	0.1
2043	2038	Thunbergol A	0.5	–	–
2054	2053	Manool	0.7	0.4	0.2
2087	2089	Abietadiene	0.2	0.1	0.1
2226	—	iso-Pimarinal^a	0.2	0.2	0.3
2234	2245	Palustral	0.2	0.1	0.2
2295	2297	Methyl isopimarate	0.1	0.1	0.2
2298	2305	Methyl levopimarate	0.1	0.1	0.2
2312	2312	Abietal	0.2	0.2	0.2
2334	2341	Methyl dehydroabietate	0.1	tr	0.1
2371	2366	neo-Abietic acid	0.1	tr	0.1
		Monoterpene hydrocarbons	65.9	55.0	63.5
		Oxygenated monoterpenoids	17.0	24.1	23.6
		Sesquiterpene hydrocarbons	9.6	10.3	4.1
		Oxygenated sesquiterpenoids	3.4	6.1	4.3
		Diterpenoids	3.6	2.3	2.8
		Benzenoid aromatics	0.1	0.4	0.1
		Total identified	99.6	98.2	98.5

RI_calc= Calculated retention index determined with respect to a homologous series of n-alkanes on a ZB-5 ms column.³³ RI_db= Retention index values obtained from the databases.^34-37 tr = trace (< 0.05%). ^a A reference RI value was not available, but the MS showed a 94% match.

Enantiomeric Distribution

The L. occidentalis essential oils were subjected to enantioselective GC-MS. The enantiomeric distributions of the monoterpenoid components are listed in Table 3. The enantiomeric distributions for α-pinene and verbenone were variable (virtually racemic). Sabinene was also variable, but (–)-sabinene was dominant in two of the three samples. The (–)-enantiomers were slightly dominant for limonene (58.8 ± 1.2%) and terpinen-4-ol (58.5 ± 1.4%), and (–)-enantiomers were dominant for camphene (84.1 ± 6.6%), β-pinene (97.7 ± 0.4%), β-phellandrene (80.6 ± 3.2%), borneol (86.2 ± 0.9%), and α-terpineol (85.4 ± 4.6%). (+)-δ-3-Carene was the only enantiomer observed.

Table 3.

Enantiomeric Distributions (Percent) of Monoterpenoid Components in Larix occidentalis.

Enantiomers	RI_calc	RI_db	Tree A	Tree B	Tree C
(−)-α-Pinene	975	976	61.9	54.7	48.5
(+)-α-Pinene	981	982	38.1	45.3	51.5
(−)-Camphene	1002	998	89.0	86.7	76.6
(+)-Camphene	1007	1005	11.0	13.3	23.4
(+)-Sabinene	1022	1021	51.0	17.2	18.5
(−)-Sabinene	1029	1030	49.0	82.8	81.5
(+)-β-Pinene	1027	1027	2.2	2.0	2.7
(−)-β-Pinene	1029	1031	97.8	98.0	97.3
(+)-δ-3-Carene	1049	1052	100.0	100.0	100.0
(−)-δ-3-Carene	n.d.	n.a.	0.0	0.0	0.0
(−)-Limonene	1075	1073	59.5	57.4	59.5
(+)-Limonene	1081	1081	40.5	42.6	40.5
(−)-β-Phellandrene	1084	1083	83.9	80.4	77.5
(+)-β-Phellandrene	1088	1089	16.1	19.6	22.5
(+)-Terpinen-4-ol	1298	1297	42.8	41.3	40.1
(−)-Terpinen-4-ol	1300	1300	57.2	58.7	59.9
(−)-Borneol	1335	1335	86.8	85.2	86.7
(+)-Borneol	1342	1340	13.2	14.8	13.3
(−)-α-Terpineol	1345	1347	90.7	82.0	83.5
(+)-α-Terpineol	1355	1356	9.3	18.0	16.5
(−)-Verbenone	1371	1368	67.4	54.8	43.1
(+)-Verbenone	1375	1380	32.6	45.2	56.9

RI_calc= Calculated retention index determined with respect to a homologous series of n-alkanes on a B-Dex 325 chiral capillary column. RI_db= Retention index values obtained from our own database using available reference compounds. n.d. = compound not detected. n.a. = reference compound not available.

Discussion

Essential Oil Composition

This is the first report on the essential oil of L. occidentalis from Idaho, USA. Interestingly, the sesquiterpene hydrocarbon concentration was lower in tree C (4.1%) than those in trees A and B (9.6% and 10.3%), which is attributed to the lower concentrations of (E)-β-caryophyllene, germacrene D, and δ-cadinene in tree C. It is not clear why the sesquiterpenes were lower in tree C; the samples were collected from similar locations on the same day. There have been older reports on L. occidentalis from Canada²³ and chloroform extracts from Montana.²⁴ In addition, there have been several reports on other Larix species, namely L. decidua,^27-30 Larix kaempferi (Lamb.) Carrière,³¹ Larix laricina (Du Roi) K.Koch,²³ Larix leptolepis (Siebold & Zucc.) Gordon (syn. Larix kaempferi (Lamb.) Carrière),²⁹ and Larix sibirica Ledeb.^29,32 The major essential oil components of the previously published Larix essential oils are summarized in Table 4. In order to visually compare the essential oil compositions, a hierarchical cluster analysis (HCA) was carried out using the major components (Figure 3). The dendrogram from the HCA can be divided into four clusters: (1) an α-pinene/β-pinene group, (2) a sabinene/α-pinene group (one sample), a group dominated by α-pinene, and a δ-3-carene/α-pinene group. The HCA clearly shows that the three L. occidentalis essential oil samples from Idaho are very similar to each other as well as to the L. occidentalis sample from British Columbia, and fall into the α-pinene/β-pinene group. The major components observed in L. occidentalis are consistent with those found in other Larix essential oils. That is, α-pinene and β-pinene are major components in Larix essential oils.

Figure 3.

Dendrogram Obtained by Hierarchical Cluster Analysis (HCA) of Major Volatile Components of Larix Species. L. occidentalis (Idaho) this Work, L. occidentalis (British Columbia),²³ L. lyallii (Alberta),²³ L. leptolepis (Finland),²⁹ L. decidua (Finland),²⁹ L. kaempferi (Korea),³¹ L. laricina (Yukon),²³ L. occidentalis (Montana),²⁴ L. decidua (Corsica),²⁷ L. lyallii (Montana),²⁴ L. decidua (Italy),²⁸ L. decidua (Italy, commercial),³⁰ L. sibirica (Finland),²⁹ L. sibirica (Siberia).³²

Table 4.

Major Essential Oil Components from Larix Species.

Essential Oil	Origin	Major Components	Ref.
Larix decidua leaf	Corsica	α-Pinene (30.8%), germacrene D (17.0%), β-pinene (16.1%), β-phellandrene (4.9%)	Garcia et al²⁷
Larix decidua oleoresin	South Tirol, Italy	α-Pinene (54.1%), β-pinene (6.3%), limonene^a (5.6%), α-terpineol (2.4%), δ-3-carene (2.0%)	Batista et al²⁸
Larix decidua leaf	Commercial (Italy)	α-Pinene (51.0%), myrcene (9.7%), β-ocimene^b (10.2%), 1,8-cineole (3.2%), β-pinene (2.3%)	Vitalini et al³⁰
Larix decidua leaf	Finland	α-Pinene (24.3%), δ-3-carene (21.6%), β-pinene (7.7%), β-phellandrene (6.1%), terpinolene (5.2%)	Holm and Hiltunen²⁹
Larix kaempferi leaf	Korea	α-Pinene (19.9%), β-pinene (17.4%), bornyl acetate (15.3%), limonene (7.6%), β-phellandrene (7.4%)^c	Yun et al³¹
Larix laricina twig	Yukon, Canada	δ-3-Carene (21.3%), α-pinene (20.8%), β-pinene (15.4%), bornyl acetate (14.2%), (E)-nerolidol (5.0%)	von Rudloff²³
Larix leptolepis leaf	Finland	α-Pinene (28.8%), myrcene (11.8%), δ-3-carene (10.2%), β-pinene (6.8%)	Holm and Hiltunen²⁹
Larix lyallii twig	Alberta, Canada	α-Pinene (39.2%), β-pinene (14.1%), sabinene (7.5%), δ-3-carene (6.7%)	von Rudloff²³
Larix lyallii foliage^d	Carlton Ridge, Montana, USA	Sabinene (39.3%), α-pinene (16.1%), β-pinene (14.0%), germacrene D^e (6.1%)	Carlson et al²⁴
Larix occidentalis twig	British Columbia, Canada	β-Pinene (24.1%), α-pinene (23.9%), δ-3-carene (13.6%)	von Rudloff²³
Larix occidentalis foliage^d	Carlton Ridge, Montana, USA	α-Pinene (26.0%), germacrene D^e (22.1%), β-pinene (15.5%), (E)-β-caryophyllene (7.6%)	Carlson et al²⁴
Larix sibirica litter	Krasnoyarsk, Siberia	δ-3-Carene (53.1%), α-pinene (12.6%), β-pinene (8.6%), β-phellandrene (4,5%), limonene (5.0%), bornyl acetate (4.7%)	Gornostaeva et al³²
Larix sibirica leaf	Finland	δ-3-Carene (31.9%), α-pinene (11.4%), myrcene (8.8%), β-pinene (6.3%), β-phellandrene (4,5%)	Holm and Hiltunen²⁹

^aReported as D-limonene, but an enantioselective GC column was not used.

^b(E)/(Z)-Isomer not indicated. Based on the retention index, this may be β-phellandrene.

^cIndividual enantiomers of α-pinene, β-pinene, limonene, and bornyl acetate were indicated, but an enantioselective GC column was not used.

^dThis was a chloroform extract and not an essential oil.

^eLabeled as β-cubebene, but more likely this is germacrene D.

The biological activities of the major L. occidentalis essential oil components, α-pinene,^38,39 β-pinene,³⁸ and α-terpineol^40,41 have been reviewed. α-Pinene has shown antibacterial, antifungal, anti-inflammatory, analgesic,^38,39 and wound-healing⁴² activities. β-Pinene has shown antimicrobial activity³⁸; and α-terpineol has shown anti-nociceptive, anti-bronchitis, antimicrobial, and anti-inflammatory effects.^40,41 Thus, the biological activities of the major components are consistent with the traditional uses of L. occidentalis to treat coughs, arthritis, and cuts and sores.

Enantiomeric Distribution

Holm and Hiltunen have carried out enantioselective GC-MS analysis of L. decidua, L. leptolepis, and L. sibirica leaf essential oils.²⁹ In that study, the enantiomeric distribution in α-pinene was variable, but the (–)-enantiomers were dominant for camphene, β-pinene, limonene, and β-phellandrene, while the (+)-enantiomers dominated in sabinene and δ-3-carene. Thus, the enantiomeric distributions of monoterpenoids in Larix species are relatively consistent.

Conclusions

This work reports, for the first time, the essential oil composition of Larix occidentalis collected from Brundage Mountain, Idaho. The essential oils were dominated by monoterpenoids, including α-pinene (26.5 ± 5.4%), β-pinene (14.9 ± 2.5%), α-terpineol (8.3 ± 1.2%), and δ-3-carene (6.6 ± 2.9%). The limitation of this current work is that only three samples of foliage were collected from one general area (Brundage Mountain, Idaho). Furthermore, previous investigations of Larix essential oils are either old, incomplete, or sparse. Additional work is needed to more clearly define the essential oil compositions of these species, including essential oils from the leaves and from the bark. In addition, more modern biological screening of the essential oils, their major components, and mixtures of components would help to corroborate the traditional uses of Larix species.

Supplemental Material

sj-docx-1-npx-10.1177_1934578X251334214 - Supplemental material for Chemical Composition and Enantiomeric Distribution of the Essential oil of Larix occidentalis Nutt

Supplemental material, sj-docx-1-npx-10.1177_1934578X251334214 for Chemical Composition and Enantiomeric Distribution of the Essential oil of Larix occidentalis Nutt by Ambika Poudel, Prabodh Satyal, Kathy Swor and William N Setzer in Natural Product Communications

Supplemental Material

sj-docx-2-npx-10.1177_1934578X251334214 - Supplemental material for Chemical Composition and Enantiomeric Distribution of the Essential oil of Larix occidentalis Nutt

Supplemental material, sj-docx-2-npx-10.1177_1934578X251334214 for Chemical Composition and Enantiomeric Distribution of the Essential oil of Larix occidentalis Nutt by Ambika Poudel, Prabodh Satyal, Kathy Swor and William N Setzer in Natural Product Communications

Footnotes

Acknowledgments

This work was carried out as part of the activities of the Aromatic Plant Research Center (APRC, ).

Statement of Human and Animal Rights

This article does not contain any studies with human or animal subjects.

ORCID iDs

Prabodh Satyal

William N Setzer

Ethical Considerations

Ethical approval is not applicable for this article.

Informed Consent

There are no human subjects in this article and informed consent is not applicable.

Funding

The author(s) received no financial support for the research, authorship, and/or publication of this article.

Conflicting Interests

The author(s) declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Data Availability

All the data for this study are available in the manuscript.

Supplemental Material

Supplemental material for this article is available online.

References

World Flora Online WFO. Larix occidentalis Nutt. The World Flora Online. http://www.worldfloraonline.org/taxon/wfo-0000443274. Published 2024. Accessed June 1, 2024.

Little

. Digital representations of tree species range maps. Atlas of United States Trees. https://commons.wikimedia.org/wiki/Flora_distribution_maps_of_North_America#Artemisia. Published 1971. Accessed February 24, 2024.

Moerman

. Native American Ethnobotany. Timber Press, Inc.; 1998.

Vitalini

Iriti

Puricelli

Ciuchi

Segale

Fico

. Traditional knowledge on medicinal and food plants used in Val San Giacomo (Sondrio, Italy) - An alpine ethnobotanical study. J Ethnopharmacol. 2013;145(2):517-529. doi:https://doi.org/10.1016/j.jep.2012.11.024

Mammari

Albert

Devocelle

, et al. Natural products for the prevention and treatment of common cold and viral respiratory infections. Pharmaceuticals. 2023;16(5):662. doi:https://doi.org/10.3390/ph16050662

Cornara

La Rocca

Terrizzano

Dente

Mariotti

. Ethnobotanical and phytomedical knowledge in the North-Western Ligurian Alps. J Ethnopharmacol. 2014;155(1):463-484. doi:https://doi.org/10.1016/j.jep.2014.05.046

Jarić

Kostić

Mataruga

, et al. Traditional wound-healing plants used in the Balkan region (Southeast Europe). J Ethnopharmacol. 2018;211:311-328. doi: https://doi.org/10.1016/j.jep.2017.09.018

Batista

JVC

Uecker

Holandino

, et al. A scoping review on the therapeutic potential of resin from the species Larix decidua mill. [Pinaceae] to treat ulcerating wounds. Front Pharmacol. 2022;13:895838. doi:https://doi.org/10.3389/fphar.2022.895838

Adams

Berset

Kessler

Hamburger

. Medicinal herbs for the treatment of rheumatic disorders-A survey of European herbals from the 16th and 17th century. J Ethnopharmacol. 2009;121(3):343-359. doi:https://doi.org/10.1016/j.jep.2008.11.010

10.

Schmidt

. Production of essential oils. In: Başer

KHC

Buchbauer

, eds. Handbook of Essential Oils. CRC Press; 2010:83-119.

11.

Brielmann

Setzer

Kaufman

Kirakosyan

Cseke

. Phytochemicals: the chemical components of plants. In: Cseke

Kirakosyan

Kaufman

Warber

Duke

Brielmann

, eds. Second Edi. Natural Products from Plants. CRC Press; 2006:1-49. doi:https://doi.org/10.1201/9780849331343.ch1

12.

Sell

. Chemistry of essential oils. In: Başer

KHC

Buchbauer

, eds. Handbook of Essential Oils. CRC Press; 2010:121-150.

13.

Kalemba

Kunicka

. Antibacterial and antifungal properties of essential oils. Curr Med Chem. 2003;10(10):813-829. doi: https://doi.org/10.2174/0929867033457719

14.

Abd-Elgawad

El Gendy

AE-NG

Assaeed

, et al. Phytotoxic effects of plant essential oils: a systematic review and structure-activity relationship based on chemometric analyses. Plants. 2021;10(1):36. doi:https://doi.org/10.3390/plants10010036

15.

Gupta

Singh

Muthusamy

, et al. Plant essential oils as biopesticides: applications, mechanisms, innovations, and constraints. Plants. 2023;12(16):2916. doi:https://doi.org/10.3390/plants12162916

16.

Catani

Grassi

Cocozza di Montanara

, et al. Essential oils and their applications in agriculture and agricultural products: a literature analysis through VOSviewer. Biocatal Agric Biotechnol. 2022;45:102502. doi:https://doi.org/10.1016/j.bcab.2022.102502

17.

Angane

Swift

Huang

Butts

Quek

. Essential oils and their major components: an updated review on antimicrobial activities, mechanism of action and their potential application in the food industry. Foods. 2022;11(3):464. doi:https://doi.org/10.3390/foods11030464

18.

Salanţă

Croptova

. An update on effectiveness and practicability of plant essential oils in the food industry. Plants. 2022;11(19):2488. doi:https://doi.org/10.3390/plants11192488

19.

Samakradhamrongthai

. Aroma and Flavor in Product Development: Characterization, Perception, and Application. Springer; 2024.

20.

Guzmán

Lucia

. Essential oils and their individual components in cosmetic products. Cosmetics. 2021;8(4):114. doi:https://doi.org/10.3390/cosmetics8040114

21.

Rhind

. Essential Oils: A Comprehensive Handbook for Aromatic Therapy. Singing Dragon; 2020.

22.

Pinto

Corrêa

AdR

da Silva

GNC

da Costa

Figueiredo

PLB

. Drug development from essential oils: new discoveries and perspectives. In: Cruz

, ed. Drug Discovery and Design Using Natural Products. Springer; 2023:79-101.

23.

von Rudloff

. The volatile twig and leaf oil terpene compositions of three western North American larches, Larix laricina, Larix occidentalis, and Larix lyallii. J Nat Prod. 1987;50(2):317-321. doi:https://doi.org/10.1021/np50050a051

24.

Carlson

Cates

Spencer

. Foliar terpenes of a putative hybrid swarm (Larix occidentalis ( Larix lyallii) in western Montana. Can J For Res. 1991;21(6):876-881. doi: https://doi.org/10.1139/x91-122

25.

New York Botanical Garden NYBG. C. V. Starr Virtual Herbarium. https://sweetgum.nybg.org/science/vh/. Accessed June 24, 2023.

26.

Swor

Satyal

Poudel

Setzer

. The essential oils of Wyethia species: wyethia amplexicaulis (nutt.) nutt. And Wyethia helianthoides nutt. Nat Prod Commun. 2024;19(4):1934578X-241248081. doi:https://doi.org/10.1177/1934578X241248081

27.

Garcia

Gibernau

Bighelli

Tomi

. Chemical compositions of essential oils of five introduced conifers in Corsica. Nat Prod Res. 2017;31(14):1697-1703. doi:https://doi.org/10.1080/14786419.2017.1285299

28.

Batista

JVC

Melo

MdO

Holandino

, et al. Characterization of Larix decidua Mill. (Pinaceae) oleoresin’s essential oils composition using GC-MS. Front Plant Sci. 2023;14:1331894. doi:https://doi.org/10.3389/fpls.2023.1331894

29.

Holm

Hiltunen

. Variation and inheritance of monoterpenes in Larix species. Flavour Fragr J. 1997;12(5):335-339. doi:https://doi.org/10.1002/(SICI)1099-1026(199709/10)12:5<335::AID-FFJ664>3.0.CO;2-I

30.

Vitalini

Iriti

Vaglia

Garzoli

. Chemical investigation and dose-response phytotoxic effect of essential oils from two gymnosperm species (Juniperus communis var. saxatilis Pall. and Larix decidua Mill.). Plants. 2022;11(11):1510. doi:https://doi.org/10.3390/plants11111510

31.

Yun

Cho

Yeon

B-R

Choi

Kim

. Herbicidal activities of essential oils from pine, nut pine, larch and Khingan fir in Korea. Weed Turfgrass Sci. 2013;2(1):30-37. doi:https://doi.org/10.5660/wts.2013.2.1.030

32.

Gornostaeva

Golikova

Repyakh

. Composition of the essential oil of Larix sibirica. Chem Nat Compd. 1982;18(3):287-290. doi:https://doi.org/10.1007/BF00580452

33.

van den Dool

Kratz

. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr A. 1963;11:463-471. doi:https://doi.org/10.1016/S0021-9673(01)80947-X

34.

Adams

. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. 4th ed. Allured Publishing; 2007.

35.

Mondello

. FFNSC 3. Shimadzu Scientific Instruments; 2016.

36.

NIST20. Maryland National Institute of Standards and Technology; 2020.

37.

Satyal

Development of GC-MS Database of Essential Oil Components by the Analysis of Natural Essential Oils and Synthetic Compounds and Discovery of Biologically Active Novel Chemotypes in Essential Oils , Ph.D. dissertation. 2015.

38.

Salehi

Upadhyay

Orhan

, et al. Therapeutic potential of α-and β-pinene: a miracle gift of nature. Biomolecules. 2019;9(11):738. doi:https://doi.org/10.3390/biom9110738

39.

Allenspach

Steuer

. α-Pinene: a never-ending story. Phytochemistry. 2021;190:112857. doi:https://doi.org/10.1016/j.phytochem.2021.112857

40.

Khaleel

Tabanca

Buchbauer

. α-Terpineol, a natural monoterpene: a review of its biological properties. Open Chem. 2018;16(2):349-361. doi:https://doi.org/10.1515/chem-2018-0040

41.

Sales

Felipe

LdO

Lemos

. Production, properties, and applications of α-terpineol. Food Bioprocess Technol. 2020;13:1261-1279. doi:https://doi.org/10.1007/s11947-020-02461-6

42.

Salas-Oropeza

Jimenez-Estrada

Perez-Torres

, et al. Wound healing activity of α-pinene and α-phellandrene. Molecules. 2021;26(9):2488. doi:https://doi.org/10.3390/molecules26092488

Supplementary Material

Please find the following supplemental material available below.

For Open Access articles published under a Creative Commons License, all supplemental material carries the same license as the article it is associated with.

For non-Open Access articles published, all supplemental material carries a non-exclusive license, and permission requests for re-use of supplemental material or any part of supplemental material shall be sent directly to the copyright owner as specified in the copyright notice associated with the article.

0.00 MB

0.01 MB

0.47 MB