Citrus reticulata Leaves Essential Oil as an Antiaging Agent: A Comparative Study between Different Cultivars and Correlation with Their Chemical Compositions
Abstract
:1. Introduction
2. Results and Discussion
2.1. Extraction and Distillation of the Essential Oils
2.2. Metabolic Profile of the Essential Oils
2.3. Chemometric Analysis Based on GC-MS Analysis
2.4. In Vitro Antiaging Activity
2.5. In Silico Molecular Docking Studies on the Target Enzymes
3. Materials and Methods
3.1. Plant Material
3.2. Hydro-Distillation of the Essential Oil and GC-MS Analysis
3.3. Multivariate Analysis
3.4. In Vitro Antiaging Activity
3.4.1. Hyaluronidase Inhibition Assay
3.4.2. Collagenase Inhibition Assay
3.4.3. Elastase Inhibition Assay
3.5. Statistical Analysis
3.6. In Silico Molecular Docking Study
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Citrus reticulata Cultivar | Cultivar Code | Yield % (w/w) |
---|---|---|
Avana Apriena mandarin | Am | 0.232 |
Balady mandarin | Bm | 0.220 |
Cara mandarin | Cm | 0.124 |
Willow leaf mandarin | Wm | 0.078 |
Sunburst mandarin | Sm | 0.130 |
Kishu mandarin | Km | 0.151 |
No. | Rt | Compound Name | KIexp a | KIrep b | Content% | Molecular Formula | |||||
---|---|---|---|---|---|---|---|---|---|---|---|
Am | Bm | Cm | Wm | Sm | Km | ||||||
1. | 7.19 | α-Thujene | 911 | 911 | 0.97 ± 0.05 | 0.67 ± 0.17 | 1.37 ± 0.03 | 1.55 ± 0.63 | 0.73 ± 0.12 | 1.08 ± 0.07 | C10H16 |
2. | 7.38 | α-Pinene | 918 | 918 | 2.54 ± 0.12 | 1.85 ± 0.49 | 3.76 ± 0.07 | 3.72 ± 0.98 | 2.93 ± 0.65 | 3.77 ± 0.17 | C10H16 |
3. | 7.82 | Camphene | 933 | 933 | 0.03 ± 0.01 | 0.01 ± 0.02 | 0.06 ± 0.01 | 0.05 ± 0.01 | 0.09 ± 0.01 | 0.18 ± 0.01 | C10H16 |
4. | 8.61 | β-Thujene | 962 | 962 | - | - | - | - | - | 3.34 ± 0.10 | C10H16 |
5. | 8.68 | β-Pinene | 965 | 965 | 2.48 ± 0.11 | 1.80 ± 0.38 | 6.34 ± 0.06 | 3.53 ± 0.68 | 34.24 ± 3.50 | 19.62 ± 0.37 | C10H16 |
6. | 9.13 | β-Myrcene | 981 | 981 | 0.44 ± 0.02 | 0.16 ± 0.15 | 1.13 ± 0.07 | 1.10 ± 0.21 | 5.16 ± 0.21 | 0.89 ± 0.11 | C10H16 |
7. | 9.52 | α-Phellandrene | 995 | 995 | 0.06 ± 0.00 | 0.02 ± 0.03 | 0.13 ± 0.04 | 0.04 ± 0.00 | 0.20 ± 0.00 | 0.13 ± 0.09 | C10H16 |
8. | 9.72 | 3-Carene | 1002 | 1002 | 0.06 ± 0.00 | 0.04 ± 0.01 | 0.03 ± 0.03 | 0.01 ± 0.01 | 0.02 ± 0.01 | - | C10H16 |
9. | 9.90 | 2-Carene | 1008 | 1008 | 0.28 ± 0.01 | 0.20 ± 0.04 | 1.03 ± 0.04 | 0.45 ± 0.03 | 3.54 ± 0.16 | 0.69 ± 0.04 | C10H16 |
10. | 10.08 | p-Cymene | 1014 | 1014 | 2.45 ± 0.10 | 1.74 ± 0.31 | 2.29 ± 0.08 | 3.11 ± 0.02 | - | 2.29 ± 0.09 | C10H14 |
11. | 10.17 | m-Mentha-6,8-diene | 1017 | 1019 | - | - | - | - | 4.12 ± 0.18 | - | C10H16 |
12. | 10.29 | D-Limonene | 1020 | 1021 | 10.22 ± 0.18 | 7.85 ± 1.50 | 10.03 ± 0.27 | 12.49 ± 0.21 | - | 6.34 ± 0.04 | C10H16 |
13. | 10.59 | trans-β-Ocimene | 1030 | 1031 | 0.06 ± 0.01 | 0.10 ± 0.06 | 0.12 ± 0.01 | 0.41 ± 0.02 | 0.31 ± 0.01 | 0.06 ± 0.01 | C10H16 |
14. | 10.92 | cis-β-Ocimene | 1041 | 1041 | 0.36 ± 0.02 | 0.27 ± 0.02 | 8.29 ± 0.25 | 1.99 ± 0.01 | 11.31 ± 0.62 | 2.81 ± 0.10 | C10H16 |
15. | 11.23 | γ-Terpinene | 1051 | 1052 | 19.37 ± 0.3 | 21.04 ± 0.36 | 48.56 ± 1.01 | 19.42 ± 0.50 | 6.19 ± 0.31 | 17.92 ± 0.26 | C10H16 |
16. | 11.53 | trans-Sabinenehydrate | 1060 | 1062 | - | - | - | - | 0.22 ± 0.02 | 0.03 ± 0.01 | C10H18O |
17. | 12.15 | α-Terpinolene | 1080 | 1082 | 0.61 ± 0.05 | 0.63 ± 0.03 | 3.31 ± 0.14 | 1.20 ± 0.14 | 1.12 ± 0.09 | 1.78 ± 0.07 | C10H16 |
18. | 12.28 | p-Cymenene | 1085 | 1085 | - | - | - | - | - | 0.41 ± 0.14 | C10H12 |
19. | 12.54 | Linalool | 1093 | 1093 | - | - | 5.18 ± 0.34 | 0.53 ± 0.06 | 16.8 ± 1.49 | 22.20 ± 0.43 | C10H18O |
20. | 13.22 | Cis-Sabinenehydrate | 1115 | 1116 | - | - | - | - | 0.40 ± 0.05 | 0.02 ± 0.00 | C10H18O |
21. | 14.85 | Isocamphopinone | 1167 | 1168 | - | - | - | - | - | 0.03 ± 0,00 | C10H16O |
22. | 14.95 | Terpinen-4-ol | 1170 | 1171 | 0.24 ± 0.02 | - | 0.08 ± 0.13 | 0.19 ± 0.03 | 10.91 ± 1.35 | 0.81 ± 0.01 | C10H18O |
23. | 15.38 | α-Terpineol | 1184 | 1184 | - | - | - | 0.17 ± 0.04 | 0.50 ± 0.05 | 0.79 ± 0.01 | C10H18O |
24. | 16.64 | Anisole | 1227 | 1227 | - | - | - | 0.20 ± 0.02 | - | 1.11 ± 0.01 | C7H8O |
25. | 18.38 | Thymol | 1288 | 1288 | - | - | - | - | - | 10.98 ± 0.27 | C10H14O |
26. | 18.50 | Carvacrol | 1292 | 1292 | - | - | - | 0.36 ± 0.04 | - | - | C10H14O |
27. | 19.59 | σ-Elemene | 1330 | 1330 | - | - | - | 0.01 ± 0.01 | - | 0.07 ± 0.01 | C15H24 |
28. | 21.12 | β-Elemene | 1384 | 1385 | 0.28 ± 0.01 | 0.24 ± 0.02 | 5.54 ± 0.10 | 0.11 ± 0.01 | 0.64 ± 0.06 | 0.06 ± 0.01 | C15H24 |
29. | 21.62 | Dimethyl anthranilate | 1401 | 1402 | 56.51 ± 1.06 | 58.77 ± 2.04 | 0.02 ± 0.02 | 49.06 ± 1.94 | - | - | C9H11NO2 |
30. | 21.90 | β-Caryophyllene | 1412 | 1413 | 2.90 ± 0.09 | 4.38 ± 0.51 | 1.36 ± 0.01 | - | 0.30 ± 0.03 | 0.82 ± 0.01 | C15H24 |
31. | 22.82 | α-Caryophyllene | 1448 | 1448 | 0.09 ± 0.01 | 0.19 ± 0.09 | 0.60 ± 0.01 | 0.19 ± 0.01 | 0.07 ± 0.01 | 0.09 ± 0.01 | C15H24 |
32. | 23.37 | β-Chamigren | 1470 | 1473 | - | - | 0.03 ± 0.00 | - | - | - | C15H24 |
33. | 23.53 | Germacrene D | 1476 | 1476 | - | - | - | - | - | 0.02 ± 0.00 | C15H24 |
34. | 23.69 | β-Selinene | 1482 | 1483 | - | - | 0.07 ± 0.01 | - | - | - | C15H24 |
35. | 23.94 | δ-Guaiene | 1492 | 1493 | 0.03 ± 0.00 | 0.04 ± 0.01 | 0.30 ± 0.01 | 0.08 ± 0.01 | - | 1.06 ± 0.02 | C15H24 |
36. | 24.18 | α-Selinene | 1501 | 1501 | - | - | 0.23 ± 0.01 | - | - | - | C15H24 |
37. | 24.26 | α-Farnesene | 1505 | 1505 | - | - | - | - | - | 0.22 ± 0.02 | C15H24 |
38. | 24.59 | σ-Cadinene | 1517 | 1517 | - | - | 0.04 ± 0.00 | - | - | 0.12 ± 0.00 | C15H24 |
39. | 26.18 | Caryophyllene oxide | 1579 | 1579 | - | - | - | 0.02 ± 0.00 | - | 0.02 ± 0.02 | C15H24O |
Monoterpene hydrocarbons (%) | 39.93 | 36.38 | 86.45 | 49.07 | 69.96 | 61.31 | |||||
Oxygenated monoterpenes (%) | 0.24 | - | 5.26 | 1.25 | 28.83 | 34.86 | |||||
Sesquiterpene hydrocarbons (%) | 3.30 | 4.85 | 8.16 | 0.39 | 1.01 | 2.46 | |||||
Oxygenated sesquiterpenes (%) | - | - | - | 0.02 | - | 0.02 | |||||
Others (%) | 56.51 | 58.77 | 0.02 | 49.26 | - | 1.11 | |||||
Total identified (%) | 99.98 | 100 | 99.89 | 99.99 | 99.80 | 99.76 |
Compound Name | Docking Score with Hyaluronidase (1fcv) Kcal/mole | Docking Score with Collagenase (456c) Kcal/mole | Docking Score with Elastase (6eoq) Kcal/mole |
---|---|---|---|
α-Pinene | −7.1 | −6.8 | −5.9 |
D-Limonene | −5.8 | −7.3 | −6.8 |
cis-β-Ocimene | −6.6 | −7.3 | −7.4 |
γ-Terpinene | −7.1 | −7.1 | −6.9 |
Linalool | −8.1 | −7.9 | −9.1 |
Terpinen-4-ol | −7.3 | −7.4 | −6.7 |
Thymol | −9.8 | −10.2 | −12.3 |
Dimethyl anthranilate | −8.2 | −8.6 | −8.0 |
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Fahmy, N.M.; Elhady, S.S.; Bannan, D.F.; Malatani, R.T.; Gad, H.A. Citrus reticulata Leaves Essential Oil as an Antiaging Agent: A Comparative Study between Different Cultivars and Correlation with Their Chemical Compositions. Plants 2022, 11, 3335. https://doi.org/10.3390/plants11233335
Fahmy NM, Elhady SS, Bannan DF, Malatani RT, Gad HA. Citrus reticulata Leaves Essential Oil as an Antiaging Agent: A Comparative Study between Different Cultivars and Correlation with Their Chemical Compositions. Plants. 2022; 11(23):3335. https://doi.org/10.3390/plants11233335
Chicago/Turabian StyleFahmy, Nouran M., Sameh S. Elhady, Douha F. Bannan, Rania T. Malatani, and Haidy A. Gad. 2022. "Citrus reticulata Leaves Essential Oil as an Antiaging Agent: A Comparative Study between Different Cultivars and Correlation with Their Chemical Compositions" Plants 11, no. 23: 3335. https://doi.org/10.3390/plants11233335