Essential Oil Composition of Grindelia squarrosa from Southern Idaho
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Plant Material
3.2. Gas Chromatographic Analysis
3.3. Antibacterial and Antifungal Screening
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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RIcalc | RIdb | Compounds | % | RIcalc | RIdb | Compounds | % |
---|---|---|---|---|---|---|---|
788 | 780 | 3-Methyl-2 butenal | 0.1 | 1392 | 1392 | (Z)-Jasmone | 0.1 |
849 | 849 | (2E)-Hexenal | 0.2 | 1429 | 1427 | γ-Elemene | 1.6 |
923 | 923 | Tricyclene | 0.1 | 1447 | 1447 | Geranylacetone | 0.1 |
926 | 925 | α-Thujene | 0.1 | 1454 | 1454 | α-Humulene | 0.2 |
934 | 933 | α-Pinene | 21.9 | 1474 | 1475 | γ-Muurolene | 0.1 |
950 | 950 | Camphene | 1.7 | 1480 | 1480 | Germacrene D | 2.4 |
953 | 953 | Thuja-2,4(10)-diene | 0.2 | 1487 | 1487 | β-Selinene | 0.3 |
972 | 971 | Sabinene | 0.2 | 1494 | 1497 | Bicyclogermacrene | 0.2 |
978 | 978 | β-Pinene | 4.2 | 1497 | 1500 | α-Muurolene | 0.1 |
989 | 989 | Myrcene | 1.0 | 1501 | 1504 | epi-Zonarene | 0.1 |
1007 | 1006 | α-Phellandrene | 0.7 | 1504 | 1503 | Bornyl isovalerate | 0.1 |
1010 | 1009 | δ-3-Carene | 0.1 | 1511 | 1510 | 1,11-Oxidocalamenene | 0.4 |
1017 | 1017 | α-Terpinene | 0.3 | 1516 | 1518 | δ-Cadinene | 0.3 |
1025 | 1025 | p-Cymene | 0.2 | 1535 | 1540 | Selina-4(15),7(11)-diene | 0.2 |
1030 | 1026 | Limonene | 17.1 | 1539 | 1542 | Selina-3,7(11)-diene | 0.1 |
1032 | 1031 | β-Phellandrene | 0.1 | 1557 | 1557 | Germacrene B | 3.5 |
1033 | 1032 | 1,8-Cineole | 0.1 | 1569 | 1571 | (3Z)-Hexenyl benzoate | 0.1 |
1035 | 1034 | 2,2,6-Trimethylcyclohexanone | 0.1 | 1574 | 1576 | Spathulenol | 0.1 |
1035 | 1034 | (Z)-β-Ocimene | tr | 1577 | 1581 | Hexyl benzoate | 0.1 |
1046 | 1046 | (E)-β-Ocimene | 1.7 | 1583 | 1582 | epi-Globulol | 0.1 |
1057 | 1057 | γ-Terpinene | 0.1 | 1624 | 1624 | Selina-6-en-4β-ol | 0.1 |
1086 | 1086 | Terpinolene | 10.6 | 1626 | 1627 | 1-epi-Cubenol | 0.1 |
1090 | 1093 | p-Cymenene | 0.1 | 1640 | 1638 | τ-Cadinol | 0.1 |
1113 | 1113 | (E)-4,8-Dimethylnona-1,3,7-triene | 0.2 | 1642 | 1640 | τ-Muurolol | 0.2 |
1121 | 1122 | Chrysanthenone | 0.2 | 1645 | 1644 | α-Muurolol (=δ-Cadinol) | 0.1 |
1127 | 1127 | α-Campholenal | 0.5 | 1653 | 1649 | β-Eudesmol | 1.4 |
1129 | 1129 | 1,3,8-p-Menthatriene | 0.2 | 1695 | 1696 | Juniper camphor | 0.2 |
1141 | 1141 | trans-Pinocarveol | 1.0 | 1765 | 1769 | Benzyl benzoate | 0.2 |
1142 | 1140 | cis-Verbenol | 0.5 | 1990 | 1994 | Manoyl oxide | 1.3 |
1146 | 1145 | trans-Verbenol | 2.2 | 2226 | a | Methyl grindelate | 0.2 |
1147 | 1145 | Camphor | 0.4 | 2300 | 2300 | Tricosane | 0.3 |
1150 | 1150 | α-Phellandren-8-ol | 0.2 | 2356 | 2355 | Grindelic acid | 1.5 |
1162 | 1164 | Pinocarvone | 0.6 | 2400 | 2400 | Tetracosane | 0.2 |
1172 | 1170 | Borneol | 6.5 | 2500 | 2500 | Pentacosane | 1.4 |
1176 | 1176 | cis-Pinocamphone | 0.3 | 2600 | 2600 | Hexacosane | 0.2 |
1180 | 1180 | Terpinen-4-ol | 0.2 | 2700 | 2700 | Heptacosane | 1.0 |
1188 | 1188 | p-Cymen-8-ol | 0.2 | 2800 | 2800 | Octacosane | tr |
1196 | 1196 | Myrtenal | 0.7 | Monoterpene hydrocarbons | 60.4 | ||
1197 | 1194 | Myrtenol | 0.4 | Oxygenated monoterpenoids | 18.6 | ||
1208 | 1205 | Verbenone | 0.9 | Sesquiterpene hydrocarbons | 9.5 | ||
1217 | 1217 | Coumaran | 0.5 | Oxygenated sesquiterpenoids | 4.0 | ||
1220 | 1218 | trans-Carveol | 0.3 | Diterpenoids | 1.7 | ||
1285 | 1285 | Bornyl acetate | 3.3 | Benzenoid aromatics | 1.0 | ||
1308 | 1309 | 4-Vinylguaicol | 0.2 | n-Alkanes | 3.2 | ||
1322 | 1322 | Myrtenyl acetate | 0.1 | Others | 1.0 | ||
1332 | 1334 | Bicycloelemene | 0.2 | Total identified | 99.3 | ||
1335 | 1336 | δ-Elemene | 0.3 |
Grindelia Species | Geographical Origin | Major Components (>4%) | Ref. |
---|---|---|---|
Grindelia discoidea Hook. & Arn. (syn. G. pulchella var. pulchella) | Argentina | (Z,E)-Farnesol (18.2–34.9%), (E,E)-farnesol (9.0–16.8%), γ-cadinene (9.4–15.6%), globulol (6.2–10.5%), (E)-β-caryophyllene (trace-8.6%), δ-cadinene (3.2–6.1%) | [12] |
Grindelia hirsutula Hook. & Arn. | Romania | Limonene (7.0%), α-pinene (6.2%), germacrene D (4.2%), spathulenol (5.5%), 10,11-epoxycalamenene (4.1%) | [17] |
Grindelia humilis Hook. & Arn. (syn. G. hirsutula Hook. & Arn.) | Egypt | Polyacetylene isomer (22.1%), germacrene D (11.9%), polyacetylene isomer (10.5%), bornyl acetate (5.1%), α-pinene (4.9%), (E)-lachnophyllol acetate (4.1%) | [13] |
Grindelia integrifolia DC. | Poland | Myrcene (16.9%), spathulenol (12.3%), β-eudesmol (11.9%), limonene (10.1%), α-cadinene (6.4%), α-pinene (4.6%), germacrene D (4.5%), humulene epoxide I (4.1%) | [18] |
Grindelia robusta Nutt. (syn. G. hirsutula Hook. & Arn.) | Germany | Germacrene D (23.3%), α-pinene (13.4%), germacrene B (8.3%), myrcene (7.2%), (E)-β-caryophyllene (4.1%) | [16] |
Commercial a | Borneol (14.8%), α-pinene (8.8%), trans-pinocarveol (6.1%), bornyl acetate (5.4%), limonene (4.1%), p-cymen-8-ol (4.1%) | [13] | |
Italy | Borneol (15.2%), α-pinene (10.3%), trans-pinocarveol (7.0%), bornyl acetate (4.5%), limonene (4.3%), β-eudesmol (4.1%) | [14] | |
Italy | Borneol (15.0%), α-pinene (11.0%), trans-pinocarveol (8.2%), β-eudesmol (5.5%), bornyl acetate (4.4%), β-selinene (4.3%), limonene (4.2%), | [15] | |
Grindelia squarrosa (Pursh) Dunal | Germany | Limonene (16.2%), germacrene B (13.2%), α-pinene (10.4%), phytone (6.5%), bornyl isovalerate (4.3%) | [16] |
Commercial a | Limonene (16.8%), α-pinene (16.1%), germacrene D (6.8%), β-pinene (5.2%), borneol (4.5%) | [13] | |
Romania | Bornyl acetate (10.8%), α-pinene (8.3%), limonene (8.1%), spathulenol (5.4%), caryophyllene oxide (4.9%) | [17] | |
Montana, USA | α-Pinene (23.2%), borneol (16.6%), limonene (14.7%), p-cymen-8-ol (5.8%), bornyl acetate (5.1%) | [19] | |
Idaho, USA | α-Pinene (21.9%), limonene (17.1%), terpinolene (10.6%), borneol (6.5%), β-pinene (4.2%) | this work |
Compounds | RTstd | RTEO | % |
---|---|---|---|
(–)-α-Pinene | 15.92 | 15.19 | 99.3 |
(+)-α-Pinene | 16.40 | 16.38 | 0.7 |
(–)-Camphene | 17.73 | 17.86 | 99.0 |
(+)-Camphene | 18.30 | 18.40 | 1.0 |
(+)-Sabinene | 19.74 | 19.78 | 100.0 |
(–)-Sabinene | 20.60 | nd | 0.0 |
(+)-β-Pinene | 20.27 | 20.28 | 10.7 |
(–)-β-Pinene | 20.62 | 20.62 | 89.3 |
(–)-α-Phellandrene | 22.59 | nd | 0.0 |
(+)-α-Phellandrene | 22.81 | 22.85 | 100.0 |
(–)-Limonene | 25.06 | 25.09 | 2.8 |
(+)-Limonene | 25.99 | 25.39 | 97.2 |
(–)-β-Phellandrene | 26.15 | 26.50 | 29.4 |
(+)-β-Phellandrene | 26.88 | 27.06 | 70.6 |
(–)-Camphor | 49.84 | 50.12 | 100.0 |
(+)-Camphor | 50.34 | nd | 0.0 |
(–)-Borneol | 58.59 | 58.31 | 100.0 |
(+)-Borneol | 59.11 | nd | 0.0 |
(–)-Bornyl acetate | 59.46 | 59.48 | 100.0 |
(+)-Bornyl acetate | na | nd | 0.0 |
(–)-α-Terpineol | 59.73 | 59.79 | 80.2 |
(+)-α-Terpineol | 60.58 | 60.62 | 19.8 |
(–)-Verbenone | 61.70 | 61.84 | 100.0 |
(+)-Verbenone | na | nd | 0.0 |
(+)-Germacrene D | 73.48 | 73.52 | 78.5 |
(–)-Germacrene D | 73.73 | 73.78 | 21.5 |
Bacteria | |||||
---|---|---|---|---|---|
Compound | Cutibacterium acnes | Staphylococcus aureus | Staphylococcus epidermidis | Streptococcus pneumoniae | Streptococcus pyogenes |
(+)-α-Pinene | 625 | 625 | 312.5 | 78.1 | 625 |
(–)-α-Pinene a | 625 | 312.5 | 312.5 | 78.1 | 312.5 |
(–)-β-Pinene a | 312.5 | 156.3 | 312.5 | 39.1 | 625 |
(+)-Limonene a | 625 | 312.5 | 312.5 | 78.1 | 312.5 |
(–)-Limonene | 39.1 | 312.5 | 78.1 | 78.1 | 625 |
(–)-Borneol a | 312.5 | 78.1 | 312.5 | 625 | 625 |
(–)-Bornyl acetate a | 312.5 | 312.5 | 312.5 | 312.5 | 625 |
Gentamicin b | <19.5 | 0.61 | <19.5 | <19.5 | <19.5 |
DMSO c | 1250 | 1250 | 1250 | 1250 | 1250 |
Fungi | |||||
Microsporum canis | Microsporum gypseum | Serratia marcescens | Trichophyton mentagrophytes | Trichophyton rubrum | |
(+)-α-Pinene | 312.5 | 156.3 | 312.5 | 156.3 | 312.5 |
(–)-α-Pinene a | 312.5 | 312.5 | 312.5 | 312.5 | 312.5 |
(–)-β-Pinene a | 312.5 | 312.5 | 312.5 | 156.3 | 312.5 |
(+)-Limonene a | 312.5 | 312.5 | 625 | 312.5 | 312.5 |
(–)-Limonene | 312.5 | 156.3 | 312.5 | 156.3 | 312.5 |
(–)-Borneol a | 312.5 | 312.5 | 625 | 156.3 | 312.5 |
(–)-Bornyl acetate a | 312.5 | 312.5 | 625 | 156.3 | 312.5 |
Amphotericin B b | <19.5 | <19.5 | <19.5 | <19.5 | <19.5 |
DMSO c | 1250 | 1250 | 1250 | 1250 | 1250 |
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Poudel, A.; Dosoky, N.S.; Satyal, P.; Swor, K.; Setzer, W.N. Essential Oil Composition of Grindelia squarrosa from Southern Idaho. Molecules 2023, 28, 3854. https://doi.org/10.3390/molecules28093854
Poudel A, Dosoky NS, Satyal P, Swor K, Setzer WN. Essential Oil Composition of Grindelia squarrosa from Southern Idaho. Molecules. 2023; 28(9):3854. https://doi.org/10.3390/molecules28093854
Chicago/Turabian StylePoudel, Ambika, Noura S. Dosoky, Prabodh Satyal, Kathy Swor, and William N. Setzer. 2023. "Essential Oil Composition of Grindelia squarrosa from Southern Idaho" Molecules 28, no. 9: 3854. https://doi.org/10.3390/molecules28093854