Essential Oil Yield, Composition, Antioxidant and Microbial Activity of Wild Fennel (Foeniculum vulgare Mill.) from Monte Negro Coast
Abstract
:1. Introduction
2. Material and Methods
2.1. Plant Material
2.2. Clevenger-Hydrodistillation
2.3. Gas Chromatography/Mass Spectrometry (GC/MS) and Gas Chromatography/Flame Ionization Detection (GC/FID)Analysis
2.4. Antioxidant Activity (DPPH Assay)
2.5. Antimicrobial Activity
3. Results and Discussion
3.1. Essential Oil Content
3.2. Essential Oil Composition
3.3. Antioxidant Activity
3.4. Antimicrobial Activity
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Fennel (Foeniculum vulgare Mill.) | Essential Oil Yield, mL/100 g p.m. * |
---|---|
Stems | 0.21 ± 0.0091 |
Leaves | 0.83 ± 0.0183 |
N° | tret., min | Compound | RIexp | RIlit | Method of Identification | c % |
---|---|---|---|---|---|---|
1. | 6.70 | α-Thujene | 914 | 924 | RI, MS | tr |
2. | 6.92 | α-Pinene | 922 | 932 | RI, MS | 0.9 |
3. | 7.40 | Camphene | 937 | 946 | RI, MS, Co-I | tr |
4. | 8.15 | Sabinene | 962 | 969 | RI, MS | tr |
5. | 8.28 | β-Pinene | 967 | 974 | RI, MS, Co-I | tr |
6. | 8.70 | Myrcene | 980 | 988 | RI, MS | 0.5 |
7. | 9.26 | α-Phellandrene | 998 | 1002 | RI, MS | 1.7 |
8. | 9.40 | δ-3-Carene | 1003 | 1008 | RI, MS | 1.0 |
9. | 10.06 | p-Cymene | 1020 | 1020 | RI, MS | 3.9 |
10. | 10.19 | β-Phellandrene | 1024 | 1025 | RI, MS | 2.2 |
11. | 11.28 | γ-Terpinene | 1052 | 1054 | RI, MS, Co-I | tr |
12. | 12.45 | Fenchone | 1083 | 1083 | RI, MS | 2.0 |
13. | 13.24 | cis-Thujone | 1104 | 1101 | RI, MS | 3.7 |
14. | 13.68 | trans-Thujone | 1114 | 1112 | RI, MS | 0.5 |
15. | 14.85 | Camphor | 1142 | 1141 | RI, MS, Co-I | 2.6 |
16. | 15.63 | Pinocarvone | 1161 | 1160 | RI, MS | tr |
17. | 16.01 | δ-Terpineol | 1169 | 1162 | RI, MS | 0.4 |
18. | 16.15 | Borneol | 1173 | 1165 | RI, MS, Co-I | tr |
19. | 16.29 | p-Mentha-1,5-dien-8-ol | 1176 | 1166 | RI, MS | tr |
20. | 16.52 | Terpinen-4-ol | 1182 | 1174 | RI, MS, Co-I | tr |
21. | 17.06 | p-Cymen-9-ol | 1195 | 1204 | RI, MS | tr |
22. | 17.36 | Methyl chavicol | 1202 | 1195 | RI, MS | 7.8 |
23. | 17.79 | α-Phellandrene epoxide | 1200 | - | MS | 2.9 |
24. | 17.91 | endo-Fenchyl acetate | 1215 | 1218 | RI, MS | tr |
25. | 18.52 | exo-Fenchyl acetate | 1230 | 1229 | RI, MS | 2.4 |
26. | 19.26 | Carvone | 1247 | 1239 | RI, MS | tr |
27. | 19.61 | cis-Piperitone epoxide | 1256 | 1250 | RI, MS | tr |
28. | 19.71 | trans-Piperitone epoxide | 1258 | 1252 | RI, MS | tr |
29. | 19.97 | p-Anisaldehyde | 1265 | 1270 | RI, MS | 0.9 |
30. | 20.74 | Isobornyl acetate | 1283 | 1283 | RI, MS | 0.4 |
31. | 21.40 | (E)-Anethole | 1292 | 1282 | RI, MS | 55.7 |
32. | 22.19 | 6-hydroxy-Carvotanacetone | 1317 | 1309 | RI, MS | tr |
33. | 22.89 | Methyl o-anisate | 1334 | 1334 | RI, MS | 1.4 |
34. | 24.15 | (2E)-Undecenal | 1364 | 1357 | RI, MS | tr |
35. | 24.50 | Piperitenone oxide | 1373 | 1366 | RI, MS | tr |
36. | 24.61 | α-Copaene | 1375 | 1374 | RI, MS | tr |
37. | 26.49 | (E)-Caryophyllene | 1421 | 1417 | RI, MS | 0.7 |
38. | 27.92 | α-Humulene | 1457 | 1452 | RI, MS | 0.9 |
39. | 28.17 | (E)-β-Farnesene | 1464 | 1454 | RI, MS | tr |
40. | 29.03 | Germacrene D | 1485 | 1484 | RI, MS | 0.5 |
41. | 29.51 | Phenyl ethyl 3-methylbutanoate | 1497 | 1490 | RI, MS | tr |
42. | 30.66 | δ-Cadinene | 1527 | 1522 | RI, MS | tr |
43. | 30.98 | Myristicin | 1535 | 1525 | RI, MS | tr |
44. | 33.13 | Caryophyllene oxide | 1592 | 1582 | RI, MS | 1.3 |
45. | 33.67 | Ledol | 1606 | 1602 | RI, MS | 3.0 |
46. | 34.17 | Humulene epoxide II | 1618 | 1608 | RI, MS | tr |
47. | 46.90 | Hexadecanoic acid | 1969 | 1959 | RI, MS | 1.7 |
48. | 49.36 | 13-epi-Manool | 2069 | 2059 | RI, MS | 1.0 |
Total identified | 100.0 | |||||
Grouped components (%) | ||||||
Monoterpene hydrocarbons (1–8, 10, 11) | 6.3 | |||||
Oxygen-containing monoterpenes (12–20, 23–28, 30, 32, 35) | 14.9 | |||||
Sesquiterpene hydrocarbons (36–40, 42) | 2.1 | |||||
Oxygenated sesquiterpenes (44–46) | 4.8 | |||||
Diterpenes (47) | 1.0 | |||||
Aromatic compounds (9, 21, 22 *, 29, 31 *, 33, 41, 43) * Phenolics (22, 31) | 69.7 * 63.5 | |||||
Others (34, 47) | 1.7 |
N° | tret., min | Compound | RIexp | RIlit | Method of Identification | c, % |
---|---|---|---|---|---|---|
1. | 6.70 | α-Thujene | 914 | 924 | RI, MS | tr |
2. | 6.92 | α-Pinene | 922 | 932 | RI, MS | 1.9 |
3. | 7.40 | Camphene | 937 | 946 | RI, MS, Co-I | tr |
4. | 8.15 | Sabinene | 962 | 969 | RI, MS | 0.3 |
5. | 8.28 | β-Pinene | 967 | 974 | RI, MS, Co-I | 0.4 |
6. | 8.70 | Myrcene | 980 | 988 | RI, MS | 1.3 |
7. | 9.12 | 3-Octanol | 994 | 988 | RI, MS | tr |
8. | 9.26 | α-Phellandrene | 998 | 1002 | RI, MS | 5.9 |
9. | 9.40 | δ-3-Carene | 1003 | 1008 | RI, MS | 1.7 |
10. | 10.06 | p-Cymene | 1020 | 1020 | RI, MS | 6.5 |
11. | 10.14 | Limonene | 1022 | 1024 | RI, MS, Co-I | tr |
12. | 10.19 | β-Phellandrene | 1024 | 1025 | RI, MS | 4.9 |
13. | 10.42 | (Z)-β-Ocimene | 1030 | 1032 | RI, MS | tr |
14. | 10.96 | Benzene acetaldehyde | 1044 | 1036 | RI, MS | tr |
15. | 11.28 | γ-Terpinene | 1052 | 1054 | RI, MS, Co-I | 1.4 |
16. | 12.45 | Fenchone | 1083 | 1083 | RI, MS | 3.2 |
17. | 13.24 | cis-Thujone | 1104 | 1101 | RI, MS | 0.7 |
18. | 13.68 | trans-Thujone | 1114 | 1112 | RI, MS | tr |
19. | 14.85 | Camphor | 1142 | 1141 | RI, MS, Co-I | 1.0 |
20. | 15.63 | Pinocarvone | 1161 | 1160 | RI, MS | tr |
21. | 16.01 | δ-Terpineol | 1169 | 1162 | RI, MS | tr |
22. | 16.29 | p-Mentha-1,5-dien-8-ol | 1176 | 1166 | RI, MS | tr |
23. | 16.52 | Terpinen-4-ol | 1182 | 1174 | RI, MS, Co-I | tr |
24. | 17.06 | p-Cymen-9-ol | 1195 | 1204 | RI, MS | tr |
25. | 17.36 | Methyl chavicol | 1202 | 1195 | RI, MS | 9.3 |
26. | 17.79 | α-Phellandrene epoxide | 1200 | - | MS | 1.2 |
27. | 17.91 | endo-Fenchyl acetate | 1215 | 1218 | RI, MS | 0.5 |
28. | 18.52 | exo-Fenchyl acetate | 1230 | 1229 | RI, MS | 1.0 |
29. | 19.26 | Carvone | 1247 | 1239 | RI, MS | tr |
30. | 19.61 | cis-Piperitone epoxide | 1256 | 1250 | RI, MS | 1.2 |
31. | 19.71 | trans-Piperitone epoxide | 1258 | 1252 | RI, MS | 1.8 |
32. | 19.97 | p-Anisaldehyde | 1265 | 1270 | RI, MS | tr |
33. | 20.74 | Isobornyl acetate | 1283 | 1283 | RI, MS | tr |
34. | 21.40 | (E)-Anethole | 1292 | 1282 | RI, MS | 51.4 |
35. | 22.19 | 6-hydroxy-Carvotanacetone | 1317 | 1309 | RI, MS | tr |
36. | 22.89 | Methyl o-anisate | 1334 | 1334 | RI, MS | 1.3 |
37. | 24.15 | (2E)-Undecenal | 1364 | 1357 | RI, MS | tr |
38. | 24.50 | Piperitenone oxide | 1373 | 1366 | RI, MS | 1.2 |
39. | 26.49 | (E)-Caryophyllene | 1421 | 1417 | RI, MS | 0.3 |
40. | 27.92 | α-Humulene | 1457 | 1452 | RI, MS | tr |
41. | 28.17 | (E)-β-Farnesene | 1464 | 1454 | RI, MS | tr |
42. | 29.03 | Germacrene D | 1485 | 1484 | RI, MS | 0.9 |
43. | 30.66 | δ-Cadinene | 1527 | 1522 | RI, MS | tr |
44. | 30.98 | Myristicin | 1535 | 1525 | RI, MS | tr |
45. | 33.13 | Caryophyllene oxide | 1592 | 1582 | RI, MS | 0.4 |
46. | 33.67 | Ledol | 1606 | 1602 | RI, MS | 0.4 |
Total identified | 100.0 | |||||
Grouped components (%) | ||||||
Monoterpene hydrocarbons (1–6, 8, 9, 11–13, 15) | 17.8 | |||||
Oxygen-containing monoterpenes (16–23, 26–31, 33, 35, 38) | 11.8 | |||||
Sesquiterpene hydrocarbons (39–43) | 1.2 | |||||
Oxygenated sesquiterpenes (45, 46) | 0.8 | |||||
Aromatic compounds (10, 14, 24, 25, 32, 34, 36, 44) * Phenolics (25, 34) | 68.5 * 60.7 | |||||
Others (7, 37) | tr |
Essential Oil | EC50, mg/mL | |
---|---|---|
Without Incubation | 40 min Incubation | |
Fennel stems | / | 2.58 ± 0.101 |
Fennel leaves | / | 6.91 ± 0.014 |
Inhibition Zone (mm) | |||||||||
---|---|---|---|---|---|---|---|---|---|
Escherihia coli | Pseudomonas aeruginosa | Proteus vulgaris | Bacillus subtilis | Bacillus cereus | Staphylococcus aureus | Klebsiella pneumoniae | Listeria monocytogenes | Candida albicans | |
Average | 0 | 0 | 0 | 24.0 | 0 | 0 | 0 | 0 | 45.3 |
Stan dev | 1.0 | 1.527 | |||||||
Cefalexin | n.t. | n.t. | n.t. | 48.0 | n.t. | n.t. | n.t. | n.t. | n.t. |
Nystatin | n.t. | n.t. | n.t. | n.t. | n.t. | n.t. | n.t. | n.t. | 17.0 |
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Milenković, A.; Ilić, Z.; Stanojević, L.; Milenković, L.; Šunić, L.; Lalević, D.; Stanojević, J.; Danilović, B.; Cvetković, D. Essential Oil Yield, Composition, Antioxidant and Microbial Activity of Wild Fennel (Foeniculum vulgare Mill.) from Monte Negro Coast. Horticulturae 2022, 8, 1015. https://doi.org/10.3390/horticulturae8111015
Milenković A, Ilić Z, Stanojević L, Milenković L, Šunić L, Lalević D, Stanojević J, Danilović B, Cvetković D. Essential Oil Yield, Composition, Antioxidant and Microbial Activity of Wild Fennel (Foeniculum vulgare Mill.) from Monte Negro Coast. Horticulturae. 2022; 8(11):1015. https://doi.org/10.3390/horticulturae8111015
Chicago/Turabian StyleMilenković, Aleksandra, Zoran Ilić, Ljiljana Stanojević, Lidija Milenković, Ljubomir Šunić, Dragana Lalević, Jelena Stanojević, Bojana Danilović, and Dragan Cvetković. 2022. "Essential Oil Yield, Composition, Antioxidant and Microbial Activity of Wild Fennel (Foeniculum vulgare Mill.) from Monte Negro Coast" Horticulturae 8, no. 11: 1015. https://doi.org/10.3390/horticulturae8111015