Subcritical Extracts from Major Species of Oil-Bearing Roses—A Comparative Chemical Profiling
Abstract
:1. Introduction
- -
- -
- Very high chemical resistance—no interaction with the processed plant, its compounds and equipment walls (high quality and purity of final product) [37];
- -
- Low viscosity and surface tension of liquid solvent [37]—intensive extraction process for short extraction times, even at low temperatures;
- -
- -
- Low boiling points [37]—easy and effective separation of final product from solvent;
- -
- Low values of vaporization heat [37]—high level of energy efficiency and low energy input for micellar separation;
- -
- Absence of own smells and taste [38]—high purity of final extracts;
- -
- Safe for the human health [38] and suitable for food-grade aroma preparations;
- -
- Fire and explosion safe properties [38];
- -
2. Results and Discussion
2.1. Phenylethanoids and Phenylpropanoids
2.2. Terpenoids
2.2.1. Monoterpenes and Their Oxygenated Derivatives
2.2.2. Sesquiterpenes
2.2.3. Triterpenoids
2.3. Aliphatic Hydrocarbons (Stearopten)
2.4. Others
3. Materials and Methods
3.1. Raw Plant Material
3.2. Extraction
3.3. Analysis
3.3.1. Gas Chromatography-Mass Spectrometry (GC/MS)
3.3.2. Gas Chromatography with Flame-Ionization Detector (GC-FID)
3.3.3. Identification, Quantitative Analysis and Chemometrics
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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No | Compound | LRIexp DB-17HT | Rel.%, as Determined Using GC-FID | |||
---|---|---|---|---|---|---|
R. galica | R. damascena | R. alba | R. centifolia | |||
1. | α-Pinene | 845 | 0.24 | 0.42 | 0.12 | 0.16 |
2. | β-Pinene | 944 | n.d. | 0.08 | 0.01 | 0.02 |
3. | β-Myrcene | 968 | 0.17 | 0.09 | 0.03 | 0.02 |
4. | Limonene | 1003 | n.d. | n.d. | 0.08 | 0.01 |
5. | p-Cymene | 1026 | n.d. | n.d. | 0.01 | n.d. |
6. | Benzaldehyde | 1051 | n.d. | n.d. | n.d. | n.d. |
7. | Linalool | 1201 | 0.07 | 0.07 | 0.10 | n.d. |
8. | Rose oxide | 1205 | n.d. | 0.01 | n.d. | n.d. |
9. | Benzyl alcohol | 1223 | 0.84 | 1.48 | 4.43 | 0.27 |
10. | Octanoic acid | 1298 | 0.14 | n.d. | 0.02 | n.d. |
11. | 2-Phenyl ethyl alcohol | 1317 | 27.22 | 59.15 | 14.07 | 8.99 |
12. | β-Citronellol | 1366 | 1.72 | 5.27 | 2.84 | 2.85 |
13. | Nerol | 1374 | 2.24 | 1.49 | 6.13 | 1.26 |
14. | Phenyl ethyl formate | 1381 | 0.12 | 0.12 | 0.08 | n.d. |
15. | Geraniol | 1414 | 8.46 | 3.01 | 14.41 | 2.87 |
16. | Neral | 1392 | n.d. | 0.21 | 0.07 | 0.10 |
17. | Geranial | 1440 | 0.34 | 0.24 | 0.95 | 0.09 |
18. | Phenyl ethyl acetate | 1469 | n.d. | 0.15 | 0.04 | 0.11 |
19. | β-Elemene | 1472 | n.d. | 0.12 | 0.01 | n.d. |
20. | Cytronellyl acetate | 1475 | n.d. | n.d. | 0.08 | n.d. |
21. | Anethole (Benzene,1-methoxy-4(1-propenyl)) | 1482 | n.d. | n.d. | 0.25 | n.d. |
22. | Pentadecane(C15) | 1500 | 0.07 | 0.06 | 0.09 | n.d. |
23. | β-Caryophyllene | 1506 | 0.25 | 0.17 | 0.98 | 0.16 |
24. | Geranic acid | 1522 | 0.11 | 0.48 | 0.26 | 0.37 |
25. | β-Copaene | 1520 | n.d. | n.d. | n.d. | 0.26 |
26. | α-Guaiene | 1518 | n.d. | 0.06 | n.d. | n.d. |
27. | Geranyl acetate | 1540 | 0.17 | 0.16 | 0.03 | n.d. |
28. | α-Caryophyllene | 1552 | n.d. | n.d. | n.d. | n.d. |
29. | Hydroxy linalool | 1568 | n.d. | n.d. | 0.03 | n.d. |
30. | Eugenol | 1574 | 0.07 | 1.26 | 0.08 | n.d. |
31. | Germacrene D | 1593 | 0.09 | 0.11 | n.d. | 0.74 |
32. | β-Cubebene | 1598 | n.d. | n.d. | n.d. | n.d. |
33. | α-Muurolene | 1607 | n.d. | n.d. | n.d. | n.d. |
34. | β-Guaiene | 1611 | n.d. | 0.06 | n.d. | n.d. |
35. | β-Copaene | 1616 | n.d. | n.d. | n.d. | n.d. |
36 | β-Cadinene | 1646 | n.d. | n.d. | n.d. | 0.12 |
37. | Methyl eugenol | 1654 | n.d. | 0.49 | n.d. | n.d. |
38. | Heptadecane (C17) | 1700 | 1.48 | 0.46 | 1.65 | 0.88 |
39. | Bulnesol | 1703 | 0.81 | 0.09 | 0.25 | 1.10 |
40. | Tetradecanal(Myristyl aldehyde) | 1706 | 0.10 | n.d. | n.d. | n.d. |
41. | Heptadecene (C17:1) | 1710 | n.d. | n.d. | 0.01 | n.d. |
42. | Benzyl tiglate + Heptadecadiene (C17:2) | 1714 | 0.14 | n.d. | 0.07 | 0.27 |
43. | Octadecane(C18) | 1744 | 0.14 | 0.06 | n.d. | 0.07 |
44. | γ-Eudesmol | 1796 | n.d. | n.d. | 0.02 | 0.05 |
45. | τ-Cadinol | 1805 | n.d. | n.d. | n.d. | n.d. |
46. | α-Eudesmol | 1819 | 0.24 | n.d. | 0.02 | 0.49 |
47. | β-Eudesmol | 1826 | 0.36 | n.d. | 0.14 | 0.81 |
48. | α-Cadinol | 1833 | n.d. | n.d. | 0.09 | n.d. |
49. | Nonadecane + Nonadecene (C19 + C19:1) | 1900 | 17.97 | 5.09 | 15.66 | 12.75 |
50. | Hexadecanal | 1936 | 0.07 | n.d | 0.04 | n.d |
51. | Eicosane(C20) | 2000 | 0.98 | 0.46 | 1.50 | 0.65 |
52. | Selina-4.7-diol | 2046 | 0.08 | n.d | n.d | 0.43 |
53. | Unknown sesquiterpene | 2054 | 0.31 | n.d | n.d | 0.92 |
54. | Heneicosane(C21) | 2100 | 9.67 | 3.09 | 11.83 | 8.34 |
55. | Heneicosene(C21:1) | 2105 | 0.24 | 0.17 | 1.31 | 0.34 |
56. | Heneicosene(C21:1), isomer | 2121 | n.d | 0.03 | 0.25 | 0.07 |
57. | Docosane(C22) | 2200 | 0.47 | 0.12 | n.d | 0.44 |
58. | Docosene(C22:1) | 2211 | n.d | n.d | n.d | 0.06 |
59. | Eudesm-4-en-3-one,11-hydroxy | 2243 | 4.67 | n.d | n.d | 0.11 |
60. | Tricosane(C23) | 2300 | 0.07 | 1.27 | 2.46 | 8.63 |
61. | Tricosene(C23:1) | 2318 | 0.30 | 0.18 | 1.86 | 1.65 |
62. | Tricosene(C23:1), isomer | 2334 | 0.10 | 0.21 | 0.33 | 0.35 |
63. | 1,1,9-Eicosadiene | 2348 | 0.09 | 0.04 | 0.12 | 0.08 |
64. | Tetracosane (C24) | 2400 | 0.25 | 0.09 | n.d | 0.44 |
65. | Farnesol acetate | 2423 | 0.14 | n.d | n.d | n.d |
66. | Hexanoic acid,2-ethyl,tetradecyl ester | 2449 | 0.33 | 0.09 | n.d | n.d |
67. | Pentacosene(C25:1) | 2511 | 0.22 | 0.07 | 0.21 | 0.17 |
68. | Pentacosene(C25:1) | 2524 | 0.07 | 0.05 | 0.97 | 0.88 |
69. | Pentacosene(C25:1) | 2532 | n.d | n.d | 0.32 | 0.30 |
70. | Octanoic acid, tetradecyl ester | 2548 | 0.10 | 0.07 | 0.04 | n.d |
71. | Hexacosane(C26) | 2600 | 0.10 | 0.06 | 0.05 | 0.11 |
72. | Hexacosene(C26:1) | 2612 | n.d | 0.05 | 0.20 | 0.13 |
73. | Octanoic acid, hexadecyl ester | 2668 | n.d | n.d | n.d | 0.22 |
74. | Heptacosane +Heptacosene (C27 + C27:1) | 2700 | 0.10 | 0.08 | 0.21 | 0.80 |
75. | Heptacosene(C27:1), isomer | 2708 | 0.42 | 0.32 | 0.27 | 0.33 |
76. | Heptacosene(C27:1), isomer | 2721 | n.d | n.d | 1.19 | 1.93 |
77. | Heptacosanol | 2789 | n.d | n.d | n.d | 0.10 |
78. | Citronellyl ester (stearate) | 2843 | 0.08 | 0.18 | n.d | 0.25 |
79. | Geranyl ester | 2876 | n.d | n.d | n.d | 0.10 |
80. | Nonacosene(C29:1) | 2911 | 1.03 | 0.81 | 0.49 | 2.13 |
81. | Phenyl ethyl ester | 2925 | 0.33 | 0.52 | 0.52 | 0.71 |
82. | Squalene | 2931 | 0.62 | 0.08 | n.d | 0.55 |
83. | Dodecanoic acid, phenyl methyl ester | 2939 | n.d | n.d | n.d | 0.16 |
84. | Citronellyl ester (phenyl acetate) | 2942 | n.d | n.d | n.d | 1.28 |
85. | Neryl ester (phenyl acetate) | 2956 | n.d | 0.06 | n.d | 1.15 |
86. | Neryl ester | 2961 | n.d | n.d | n.d | 7.35 |
87. | Phenyl ethyl ester | 2964 | n.d | n.d | n.d | 1.95 |
88. | Phenyl ethyl ester (linoleate) | 2984 | 0.08 | 0.29 | n.d | 0.10 |
89. | Citronellyl ester | 3016 | n.d | n.d | n.d | 0.55 |
90. | Geranyl ester (stearate) | 3058 | n.d | n.d | n.d | 0.87 |
91. | Neryl ester (stearate) | 3076 | 0.07 | 0.06 | n.d | 4.82 |
92. | Phenyl ethyl ester (stearate) | 3112 | n.d | n.d | n.d | 1.83 |
93. | Citronellyl ester | 3224 | n.d | n.d | n.d | 0.54 |
94. | Phenyl ethyl ester | 3421 | 0.13 | n.d | n.d | 0.45 |
95. | Neryl ester | 3432 | n.d | 0.06 | 0.29 | 0.86 |
96. | β-Amyrin | 3442 | 0.93 | 0.45 | n.d | 0.14 |
97. | Phenyl ethyl ester | 3456 | 0.31 | 0.12 | n.d | 0.35 |
98. | 9,19-Cyclolanost-24-en-3-ol acetate | 3462 | n.d | n.d | n.d | 0.27 |
99. | Olean-12-en-3-one (Amirenone) | 3468 | 0.27 | 0.28 | 0.15 | 0.65 |
100. | α-Amyrin + Unindentified triterpene | 3476 | 0.14 | 0.17 | 0.09 | 0.78 |
101. | Unindentified triterpene | 3519 | 0.79 | 0.23 | n.d | 0.25 |
102. | Lup20(29)-en-3-one | 3546 | 0.20 | 0.35 | n.d | n.d |
103. | Lupeol | 3616 | 0.74 | 1.17 | 0.15 | 0.19 |
Phenylethanoids and phenylpropanoids | 27.29 | 60.90 | 14.40 | 8.99 | ||
Monoterpenes | 13.67 | 11.89 | 25.44 | 25.52 | ||
-Monoterpene hydrocarbons | 0.41 | 0.59 | 0.25 | 0.21 | ||
-Oxygeneted monoterpenes | 13.26 | 11.30 | 25.19 | 25.31 | ||
Aliphatic hydrocarbons | 33.92 | 12.77 | 40.98 | 41.70 | ||
Sesquiterpenes | 6.95 | 0.61 | 2.05 | 5.19 | ||
Triterpenes | 3.69 | 2.73 | 0.38 | 2.83 | ||
Others | 1.15 | 1.48 | 4.96 | 0.38 | ||
TOTAL identified | 89.81 | 92.54 | 89.73 | 93.68 |
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Dobreva, A.; Nedeltcheva-Antonova, D.; Nenov, N.; Getchovska, K.; Antonov, L. Subcritical Extracts from Major Species of Oil-Bearing Roses—A Comparative Chemical Profiling. Molecules 2021, 26, 4991. https://doi.org/10.3390/molecules26164991
Dobreva A, Nedeltcheva-Antonova D, Nenov N, Getchovska K, Antonov L. Subcritical Extracts from Major Species of Oil-Bearing Roses—A Comparative Chemical Profiling. Molecules. 2021; 26(16):4991. https://doi.org/10.3390/molecules26164991
Chicago/Turabian StyleDobreva, Ana, Daniela Nedeltcheva-Antonova, Nenko Nenov, Kamelia Getchovska, and Liudmil Antonov. 2021. "Subcritical Extracts from Major Species of Oil-Bearing Roses—A Comparative Chemical Profiling" Molecules 26, no. 16: 4991. https://doi.org/10.3390/molecules26164991