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Abstract

Background

Anthriscus caucalis is a non-native plant in North America with invasive potential. As part of our interests in essential oils of the Great Basin, a wild-growing sample of A. caucalis was collected in southwestern Idaho.

Methods

The essential of A. caucalis was obtained by hydrodistillation and analyzed by gas chromatographic methods (GC–MS, GC–FID, and chiral GC–MS).

Results

The major components in the essential oil were cis-chrysanthenyl acetate (42.3%), myrcene (20.4%), cis-chrysanthenol (6.7%), α-pinene (4.2%), and (E)-β-farnesene (4.2%). (+)-α-Thujene, (+)-α-pinene, (+)-sabinene, (+)-limonene, (−)-β-phellandrene, (−)-bornyl acetate, (−)-(E)-β-caryophyllene, and (−)-germacrene D were the predominant enantiomers in the essential oil.

Conclusion

The essential oil composition of A. caucalis from Idaho is similar to those from Europe, but markedly different from A. caucalis from China. The enantiomeric distributions are comparable to those reported in other essential oils of the Apiaceae.

Keywords

essential oils chemical composition enantiomeric distribution chiral

Introduction

Anthriscus caucalis M. Bieb. (Apiaceae), bur chervil, is native to Europe, the Mediterranean region, northwest Africa and, apparently, northeastern Argentina, but has been introduced and naturalized into North America, Chile, Kirgizstan, Tajikistan, Japan, Korea, New Zealand, and Tasmania.¹ The plant was introduced to the Snake River grasslands by 1965.² The leaves of A. caucalis are triangular in shape, pinnately dissected, beset with little bristles. The inflorescences are umbels of flowers with 3–5 white rays (Figure 1). There is a high potential for invasiveness of A. caucalis where it has been introduced outside its natural range.^2‐5 The purpose of this study is to examine the essential oil composition of A. caucalis growing in the wild in the Great Basin region of Idaho.

Figure 1.

Anthriscus caucalis M. Bieb. (Apiaceae) from southwestern Idaho. Photograph by K. Swor.

Results and Discussion

The colorless aerial parts essential oil of A. caucalis was obtained in 1.414% yield by hydrodistillation. The essential oil was analyzed by GC‐MS and GC‐FID (Table 1). A total of 51 compounds were identified, accounting for 98.8% of the total composition. The major components in the essential oil were cis-chrysanthenyl acetate (42.3%), myrcene (20.4%), cis-chrysanthenol (6.7%), α-pinene (4.2%), and (E)-β-farnesene (4.2%).

Table 1.

Chemical Composition (%) of the Aerial Parts Essential Oil of Anthriscus caucalis from Southwestern Idaho.

RI_calc	RI_db	Compound	%	RI_calc	RI_db	Compound	%
849	849	(2E)-Hexenal	0.2	1297	1293	3-Thujanyl acetate	0.3
900	900	Nonane	0.4	1372	1369	(2E)-Undecenol	0.1
925	925	α-Thujene	0.3	1373	1371	α-Ylangene	tr
933	932	α-Pinene	4.2	1378	1378	Geranyl acetate	1.7
949	950	Camphene	0.1	1409	1409	Dodecanal	3.0
972	971	Sabinene	0.2	1418	1417	(E)-β-Caryophyllene	1.6
977	978	β-Pinene	0.1	1452	1451	(E)-β-Farnesene	4.2
989	989	Myrcene	20.4	1453	1453	α-Humulene	0.1
1007	1006	α-Phellandrene	tr	1479	1480	Germacrene D	1.0
1024	1025	p-Cymene	0.4	1493	1497	Bicyclogermacrene	0.2
1029	1030	Limonene	2.4	1503	1504	(E,E)-α-Farnesene	1.1
1030	1031	β-Phellandrene	0.3	1574	1576	Spathulenol	0.1
1035	1034	(Z)-β-Ocimene	3.0	1579	1577	Caryophyllene oxide	0.2
1045	1045	(E)-β-Ocimene	0.1	1612	1613	Tetradecanal	0.1
1057	1057	γ-Terpinene	0.3	1815	1817	Hexadecanal	0.1
1084	1086	Terpinolene	0.1	1996	1995	(9Z)-Octadecenal	0.1
1100	1100	Undecane	0.3	2037	2037	(Z)-Falcarinol	0.2
1127	1127	allo-Ocimene	0.1	2300	2300	Tricosane	tr
1145	1145	trans-Verbenol	0.1	2500	2500	Pentacosane	tr
1155	1152	Eucarvone	0.1	2528	2527	Methyl docosanoate	0.5
1162	1162	cis-Chrysanthenol	6.7	2700	2700	Heptacosane	0.2
1171	1170	Borneol	tr	2728	2730	Methyl tetracosanoate	0.3
1180	1180	Terpinen-4-ol	0.1			Monoterpene hydrocarbons	32.2
1197	1197	Methyl chavicol (= Estragole)	0.1			Oxygenated monoterpenoids	51.7
1206	1206	Decanal	0.8			Sesquiterpene hydrocarbons	8.3
1251	1249	Geraniol	0.1			Oxygenated sesquiterpenoids	0.3
1257	1257	cis-Chrysanthenyl acetate	42.3			Benzenoid aromatics	0.1
1277	1276	(2E)-Decen-1-ol	0.1			Others	6.2
1283	1282	Bornyl acetate	0.4			Total identified	98.8

RI_calc = Retention index determined with respect to a homologous series of n-alkanes on a ZB-5 ms column. RI_db = Reference retention index obtained from the databases.^6‐9 tr = trace (<0.05%).

The stem, leaf, and fruit essential oils of A. caucalis from two locations in Vienna, Austria, have been reported.¹⁰ The compositions of the Austrian samples are comparable to the Idaho sample. cis-Chrysanthenyl acetate dominated the tissues of the Austrian samples (52.8‐73.6%), followed by cis-chrysanthenol (2.1‐16.1%), (E)-β-farnesene (1.6‐9.7%), dodecanal (0.9‐5.2%), myrcene (0.0‐5.0%), and α-pinene (0.0‐3.7%). Interestingly, the compositions of the essential oil samples from Idaho and Austria essential oils are very different from a sample from Guizhou province, China.¹¹ The sample from China was devoid of cis-chrysanthenyl acetate, cis-chrysanthenol, dodecanal, myrcene, and α-pinene, and (E)-β-farnesene was found in a small amount (0.5%). In contrast, sesquiterpene hydrocarbons dominated the A. caucalis essential oil from China with β-bisabolene (28.4%), germacrene D (18.9%), (Z,E)-α-farnesene (16.7%), and γ-muurolene (7.3%). While germacrene D was observed in the essential oils from Idaho and Austria, neither β-bisabolene, (Z,E)-α-farnesene, nor γ-muurolene were detected. (E,E)-α-Farnesene, however, was found in both the essential oil samples from Idaho and Austria. The Flora of China lists only one species of Anthriscus in China (Anthriscus sylvestris (L.) Hoffm.).¹² There have been reports on the essential oil composition of A. sylvestris from the Netherlands,¹³ Türkiye,¹⁴ and Iran,¹⁵ and the chemical compositions of these essential oils are also very different from the A. caucalis essential oil from China. It is difficult to rationalize the very different compositions of A. caucalis essential oil of the Idaho and Austria samples compared to the China sample. It may be that they are very different chemotypes.

The enantiomeric distributions of chiral terpenoid compounds in A. caucalis essential oil have been determined using chiral GC‐MS (Table 2). The chiral gas chromatogram is available as Supplemental material (Supplementary Figure S1). The dextrorotatory enantiomers were dominant for α-thujene, α-pinene, camphene, sabinene, and limonene, whereas the levorotatory enantiomers were the exclusive stereoisomers for β-phellandrene, bornyl acetate, (E)-β-caryophyllene, and germacrene D.

Table 2.

Enantiomeric Distributions (% Enantiomer) of Chiral Terpenoid Components in the Aerial Parts Essential Oil of Anthriscus caucalis from Southwestern Idaho.

Compounds	RT_std	RT_EO	%
(+)-α-Thujene	13.92	13.91	80.7
(−)-α-Thujene	13.99	13.99	19.3
(−)-α-Pinene	15.92	16.06	4.1
(+)-α-Pinene	16.40	16.37	95.9
(−)-Camphene	17.73	18.01	17.8
(+)-Camphene	18.30	18.38	82.2
(+)-Sabinene	19.74	19.78	100.0
(−)-Sabinene	20.60	nd	0.0
(−)-Limonene	25.06	25.25	18.5
(+)-Limonene	25.99	26.03	81.5
(−)-β-Phellandrene	26.15	26.46	100.0
(+)-β-Phellandrene	26.88	nd	0.0
(−)-Bornyl acetate	59.46	59.43	100.0
(+)-Bornyl acetate	na	nd	0.0
(−)-(E)-β-Caryophyllene	69.33	69.37	100.0
(+)-(E)-β-Caryophyllene	na	nd	0.0
(+)-Germacrene D	73.48	nd	0.0
(−)-Germacrene D	73.73	73.73	100.0

RT_std = Retention time (min) of standard enantiomers. RT_EO = Retention time (min) of essential oil components. nd = enantiomer not detected. na = enantiomer not available.

The enantiomeric distributions observed for A. caucalis in this study are largely consistent with enantiomeric distributions previously reported for other essential oils of the Apiaceae. Kapetanos and co-authors have carried out a broad study of several members of the Apiaceae from the Central Balkan Peninsula (Aegopodium podagraria L., Bupleurum praealtum L., Bupleurum sibthorpianum S. S. var. diversifolium (Roch.) Hay, Chaerophyllum aureum L., Chaerophyllum hirsutum L., Chaerophyllum temulum L., Cnidium silaifolium (Jacq.) Simk. ssp. orientale (Boiss.) Tutin, Laser trilobum (L.) Brokh., Laserpitium siler L., Libanotis montana Cr., Orlaya grandiflora (L.) Hoffm., Pastinaca hirsuta Pancic., Pastinaca sativa L., Peucedanum alsaticum L., Peucedanum austriacum (Jacq.) Koch, Peucedanum cervaria (L.) Cuss., Peucedanum longifolium W. et K., Peucedanum officinale L., Peucedanum oreoselinum (L.) Moench, Physospermum cornubiense (L.) DC., Pimpinella serbica (Vis.) Bentham & Hooker, Tordylium maximum L., and Torilis anthriscus (L.) Gmel.), including chiral GC‐MS.¹⁶ These workers found (+)-α-pinene and (+)-sabinene to be the predominant enantiomers in most samples, except for P. alsaticum, P. austriacum, P. cervaria, P. longifolium, P. officinale, and P. oreoselinum; limone enantiomeric distributions varied widely; borneol and bornyl acetate, when observed, were exclusively the (−)-enantiomer. Interestingly, (+)-(E)-β-caryophyllene was the exclusive enantiomer observed in 15 essential oils, while (−)-(E)-β-caryophyllene was the exclusive enantiomer in 8 samples. According to the Dictionary of Natural Products, (−)-(E)-β-caryophyllene is the common enantiomer in higher plants, while (+)-(E)-β-caryophyllene is observed in liverworts.¹⁷

An investigation of Anethum graveolens L., Apium graveolens L., Carum carvi L., Cuminum cyminum L., Petroselinum crispum (Mill.) Fuss, and Trachyspermum ammi Sprague essential oils revealed that, when observed, (+)-α-pinene and (+)-limonene were the exclusive enantiomers.¹⁸ The enantiomeric distributions of α-pinene and sabinene in Coriandrum sativum L. fruit and herb were dominated by the (+)-enantiomers, (−)-borneol was the exclusive enantiomer observed, and limonene showed a slight excess of (+)-limonene over (−)-limonene.¹⁹

Conclusions

This is the first report on the chemical characterization of the essential oil of Anthriscus caucalis growing wild in Idaho. The composition is qualitatively similar to that reported from Austria, but profoundly different from a sample from China. The enantiomeric profiles of chiral terpenoid components of A. caucalis essential oil, reported herein for the first time, are comparable to other members of the Apiaceae.

Materials and Methods

Plant Material

Aerial parts of A. caucalis were collected from a single flowering individual on 16 May 2022 near Lucky Peak Lake (43°31ʹ40ʺ N, 116°2ʹ51ʺ W, 945 m elevation). The plant was identified by W.N. Setzer by comparison with specimens in the New York Botanical Garden.²⁰ A voucher specimen (WNS-Ac-5324) has been deposited in the University of Alabama in Huntsville herbarium. The fresh aerial parts of A. caucalis (223.5 g) were hydrodistilled for 3 h using a Likens-Nickerson apparatus to give a colorless essential oil (3.161 g).

Gas Chromatographic Analysis

The A. caucalis essential oil was analyzed by GC‐MS, GC‐FID, and chiral GC‐MS as previously described.²¹ Retention indices were calculated based on a homologous series of n-alkanes on a ZB-5 ms column.²² Each essential oil component was determined by comparison of its retention index and its mass spectral fragmentation pattern (>85% reliability index), which were available in the databases.^6‐9 Enantiomers of terpenoid components were identified by comparison of retention times with standards (Sigma-Aldrich, St. Louis, MO, USA); the enantiomer percentages were calculated based on peak areas.

Supplemental Material

sj-docx-1-npx-10.1177_1934578X231187699 - Supplemental material for The Essential Oil Composition of Anthriscus caucalis M. Bieb. (Apiaceae) Growing Wild in Southwestern Idaho

Supplemental material, sj-docx-1-npx-10.1177_1934578X231187699 for The Essential Oil Composition of Anthriscus caucalis M. Bieb. (Apiaceae) Growing Wild in Southwestern Idaho by Kathy Swor, Prabodh Satyal and William N Setzer in Natural Product Communications

Footnotes

Acknowledgements

This investigation was conducted under the auspices of the Aromatic Plant Research Center (APRC, ).

Declaration of Conflicting Interests

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

Funding

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

Ethical Approval

Ethical approval is not applicable for this article.

Statement of Human and Animal Rights

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

Informed Consent

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

ORCID iDs

Prabodh Satyal

William N Setzer

Supplemental Material

Supplemental material for this article is available online.

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