Analysis of the Volatile and Enantiomeric Compounds Emitted by Plumeria rubra L. Flowers Using HS-SPME–GC
Abstract
:1. Introduction
2. Results
2.1. Chemical Composition
2.2. Enantiomeric Distribution
3. Discussion
4. Materials and Methods
4.1. Plant Material
4.2. Selection and Preparation of Plant Material
4.3. Extraction of Compounds Using Solid-Phase Microextraction
4.4. Analysis of Volatile Compounds GC–MS
4.5. Analysis of Volatile Compounds GC–FID
4.6. Compound Identification
4.7. Enantiomeric Analysis
4.8. Statistical Analysis
5. Conclusions
Author Contributions
Funding
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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N° | Compound | LRI a | LRI b | March % ± SD | May % ± SD | July % ± SD |
---|---|---|---|---|---|---|
1 | Limonene | 1019 | 1024 | 0.02 | ||
2 | (Z)-β-Ocimene | 1027 | 1032 | 0.08 | 0.08 | 0.05 |
3 | (E)-β-Ocimene | 1038 | 1044 | 12.51 ± 0.24 | 10.82 ± 0.09 | 4.16± 0.15 |
4 | Benzene acetaldehyde | 1044 | 1036 | 0.07 ± 0.01 | 0.12 ± 0.02 | 0.09 ± 0.05 |
5 | Linalool oxide <trans-> (furanoid) | 1078 | 1084 | 0.04 | 0.1 ± 0.01 | 0.1 ± 0.02 |
6 | Linalool | 1103 | 1095 | 8.28 ± 0.16 | 11.05 ± 0.19 | 5.92 ± 0.15 |
7 | trans-Vertocitral C | 1110 | 1105 | 0.02 ± 0.01 | ||
8 | Perillene | 1111 | 1102 | 5.48 ± 0.05 | 5.85 | 3.09 ± 0.06 |
9 | 1,3,8-ρ-Menthatriene | 1123 | 1108 | 0.03 | 0.03 ± 0.01 | |
10 | Phenyl ethyl alcohol | 1124 | 1107 | 0.12 ± 0.05 | ||
11 | 2-Ethyl hexanoic acid | 1131 | 1119 | 0.12 ± 0.02 | ||
12 | Phenol <2-(1Z)-propenyl-> | 1133 | 1146 | 0.09 | 0.11 | |
13 | Linalool oxide <trans-> (pyranoid) | 1180 | 1173 | 0.02 | 0.03 | |
14 | (2E)-Hexenyl butanoate | 1195 | 1193 | 0.02 | ||
15 | Methyl salicylate | 1200 | 1190 | 0.03 | 0.05 | |
16 | cis-4-Caranone | 1214 | 1200 | 0.02 | ||
17 | iso-Dihydro carveol | 1220 | 1212 | 0.14 | 0.21 | 0.05 |
18 | NI | 1231 | 0.03 | |||
19 | (4Z)-Decen-1-ol | 1265 | 1255 | 0.03 ± 0.01 | ||
20 | α-Ylangene | 1374 | 1373 | 0.03 | 0.11 ± 0.01 | |
21 | n-Tetradecane | 1393 | 1400 | 0.04 | 0.02 ± 0.01 | 0.08 |
22 | (Z)-β-Farnesene | 1447 | 1440 | 0.23 | 0.23 ± 0.02 | |
23 | (E)-β-Farnesene | 1450 | 1454 | 0.22 ± 0.13 | ||
24 | trans-Prenyl limonene | 1460 | 1457 | 0.04 ± 0.01 | 0.07 | |
25 | NI | 1471 | 0.06 | |||
26 | γ-Decalactone | 1477 | 1465 | 0.03 ± 0.03 | 0.04 ± 0.02 | 0.1 ± 0.03 |
27 | Cumacrene | 1485 | 1470 | 1.11 ± 0.02 | 1.33 ± 0.01 | 1.01 ± 0.17 |
28 | Widdra-2,4(14)-diene | 1487 | 1481 | 0.04 ± 0.19 | ||
29 | cis-Eudesma-6,11-diene | 1491 | 1489 | 0.13 ± 0.03 | ||
30 | n-Pentadecane | 1500 | 1500 | 0.05 ± 0.01 | 0.11 ± 0.01 | 0.05 ± 0.06 |
31 | (E, E)-α-Farnesene | 1505 | 1505 | 41.64± 0.65 | 40.87± 0.35 | 41.15± 0.29 |
32 | δ-Decalactone | 1506 | 1493 | 0.19 ± 0.28 | ||
33 | γ-Patchoulene | 1519 | 1502 | 0.05 ± 0.02 | ||
34 | (Z)-γ-Bisabolene | 1523 | 1514 | 0.11 | ||
35 | β-Sesquiphellandrene | 1525 | 1521 | 0.02 | ||
36 | Decanediol <1,10-> | 1539 | 1547 | 0.03 ± 0.06 | ||
37 | (Z)-Jasmolactone, extra C | 1550 | 1566 | 0.11 ± 0.04 | ||
38 | NI | 1553 | 0.02 | |||
39 | Geranyl butanoate | 1554 | 1562 | 0.09 ± 0.04 | 0.15 ± 0.04 | |
40 | (E)-Nerolidol | 1565 | 1561 | 22.98 ± 0.61 | 21.4 ± 0.27 | 32.55 ± 1 |
41 | (Z)-dihydro-Apofarnesol | 1570 | 1571 | 6.46 ± 0.18 | 6.44 ± 0.12 | 9.89 ± 0.24 |
42 | (3Z)-Hexenyl benzoate | 1579 | 1565 | 0.04 | ||
43 | β-Copaen-4-α-ol | 1587 | 1590 | 0.06 | 0.06 | 0.11 |
44 | n-Hexadecane | 1600 | 1600 | 0.03 ± 0.02 | ||
45 | Thujopsan-2-β-ol | 1592 | 1588 | 0.05 ± 0.01 | 0.09 ± 0.01 | 0.03 ± 0.02 |
46 | epi-Cedrol | 1617 | 1618 | 0.16 ± 0.02 | 0.13 ± 0.02 | |
47 | Junenol | 1618 | 1618 | 0.23 | ||
48 | Dill apiole | 1628 | 1620 | 0.06 | ||
49 | (Z)-Amyl cinnamaldehyde | 1651 | 1647 | 0.03 ± 0.01 | ||
50 | allo-Aromadendrene epoxide | 1653 | 1639 | 0.02 | ||
51 | 14-hydroxy-(Z)-Caryophyllene | 1673 | 1666 | 0.02 | ||
52 | Helifolenol B | 1676 | 1677 | 0.03 ± 0.01 | 0.02 ± 0.01 | |
53 | n-Tetradecanol | 1677 | 1671 | 0.03 | ||
54 | n-Heptadecane | 1700 | 1700 | 0.05 ± 0.01 | 0.04 ± 0.01 | 0.05 |
55 | Khusinol | 1694 | 1679 | 0.02 | 0.03 | |
56 | (E)-Nerolidyl acetate | 1714 | 1716 | 0.02 | ||
57 | (2E,6Z)-Farnesal | 1718 | 1713 | 0.03 ± 0.01 | ||
58 | (2E,6E)-Farnesol | 1738 | 1742 | 0.02 ± 0.01 | 0.03 | |
59 | 2-ethylhexyl-Salicylate | 1806 | 1807 | 0.04 ± 0.01 | 0.06 ± 0.02 | 0.05 ± 0.01 |
Total identified (%) | 100 | 100 | 99.87 | |||
Hydrocarbon sesquiterpenes (%) | 43.12 | 42.95 | 42.53 | |||
Oxygenated sesquiterpenes (%) | 23.38 | 21.89 | 32.95 | |||
Oxygenated monoterpenes (%) | 14.03 | 17.28 | 9.51 | |||
Hydrocarbon monoterpenes (%) | 12.73 | 11.04 | 4.21 | |||
Alcohols (%) | 6.46 | 6.44 | 10.01 | |||
Aldehydes (%) | 0.07 | 0.14 | 0.12 | |||
Esters (%) | 0.12 | 0.20 | 0.06 | |||
Carboxylic acids (%) | 0.12 | |||||
NI | 0.11 |
N° | Compound | LRI a | LRI b | March % ± SD | May % ± SD | July % ± SD | Reference |
---|---|---|---|---|---|---|---|
1 | NI | 1024 | 0.07 | ||||
2 | α-Pinene | 1026 | 1024 | 0.15 | 0.76 | 0.04 | [27] |
3 | α-Thujene | 1037 | 1037 | 0.14 ± 0.01 | [28] | ||
4 | NI | 1105 | 0.02 | ||||
5 | n-Dodecane | 1200 | 1200 | 0.02 | 0.02 | 0.02 | [29] |
6 | (2E)-Hexenal | 1221 | 1230 | 0.7 | 1.6 | [30] | |
7 | (E)-β-Ocimene | 1246 | 1266 | 9.06± 1.20 | 4.96 ± 0.08 | 5.71± 0.09 | [31] |
8 | 5-Hepten-2-one, 6-methyl- | 1331 | 1340 | 0.03 | 0.04 | 0.03 | [30] |
9 | (3E)-Hexenol | 1344 | 1352 | 0.11 | [32] | ||
10 | 1-Hexanol | 1352 | 1369 | 0.82 ± 0.01 | 0.67 ± 0.01 | [30] | |
11 | 2-Methylbutyl isovalerate | 1300 | 1299 | 0.75 | 0.62 | [33] | |
12 | (E)-2-Hexen-1-ol | 1350 | 1360 | 0.13 | 0.1 | [34] | |
13 | 1,3,8-ρ-Menthatriene | 1405 | 1438 | 0.08 | 0.07 ± 0.01 | [35] | |
14 | α-Copaene | 1410 | 1458 | 0.03 | 0.03 | [28] | |
15 | Perillene | 1422 | 1425 | 3.19 ± 0.01 | 1.83 ± 0.03 | 3.00 ± 0.08 | [36] |
16 | 1-Octen-3-ol | 1425 | 1462 | 0.02 | 0.02 | [30] | |
17 | cis-Linalool oxide, furanoid | 1431 | 1437 | 0.02 | 0.06 | [37] | |
18 | trans-Linalool oxide, (furanoid) | 1449 | 1446 | 0.21 | 0.54 | 0.16 | [28] |
19 | Heptadecane, 2,6,10,15-tetramethyl- | 1469 | 1660 | 0.09 | 0.08 | [38] | |
20 | Cumacrene | 1488 | 1472 | 1.04 ± 0.01 | 1.1 ± 0.02 | 0.93 ± 0.02 | [39] |
21 | n-Pentadecane | 1500 | 1500 | 0.18 | 0.15 | 0.16 | [40] |
22 | α-Yanglene | 1503 | 1493 | 0.52 ± 0.02 | [37] | ||
23 | benzaldehyde | 1506 | 1518 | 0.02 | 0.07 | [28] | |
24 | NI | 1536 | 0.03 | ||||
25 | Linalool | 1538 | 1543 | 7.8 ± 0.04 | 4.93 ± 0.04 | 3.27 ± 0.74 | [28] |
26 | NI | 1539 | 0.19 ± 0.07 | ||||
27 | Hexadecane <n-> | 1579 | 1599 | 0.05 | 0.04 ± 0.02 | [41] | |
28 | 5-methylfurfural | 1580 | 1608 | 0.02 | [42] | ||
29 | Prenyl limonene <trans-> | 1595 | 0.66 ± 0.02 | [43] | |||
30 | Guaiol acetate | 1610 | 0.18 | 0.24 ± 0.01 | |||
31 | (Z)-β-Farnesene | 1633 | 1668 | 0.22 | 0.32 ± 0.01 | 0.23 ± 0.02 | [31] |
32 | Myrtenal | 1643 | 1646 | 0.51 | [37] | ||
33 | Heptadecane | 1700 | 1704 | 0.13 | 0.15 | [44] | |
34 | NI | 1705 | 0.13 | ||||
35 | (E, E)-α-Farnesene | 1740 | 1758 | 38.48 ± 0.04 | 38± 0.19 | 50.59 ± 0.59 | [31] |
36 | δ-cadinene | 1743 | 1764 | 0.09 | 0.1 | [37] | |
37 | NI | 1744 | 0.12 ± 0.01 | ||||
38 | trans-Linalool oxide (pyran) | 1751 | 1749 | 0.09 | 0.11 | [45] | |
39 | NI | 1762 | 0.07 ± 0.01 | ||||
40 | Myrtenol | 1811 | 1804 | 0.03 | 0.06 | 0.02 | [37] |
41 | trans-Geranylacetone | 1844 | 1867 | 0.08 | 0.04 | [46] | |
42 | NI | 1869 | 0.05 | 0.06 | 0.02 | ||
43 | NI | 1892 | 0.05 | ||||
44 | 2-Ethyl hexanoic acid | 1923 | 1950 | 0.08 | 0.07 | 0.03 | [47] |
45 | Phenylethyl Alcohol | 1922 | 1872 | 0.08 | 0.16 | 0.43 ± 0.05 | [44] |
46 | NI | 1933 | 0.10 | 0.08 | 0.04 | ||
47 | NI | 2011 | 0.12 | 0.07 | |||
48 | Aromadrene epoxide (allo) | 2029 | 2046 | 0.07 | 0.61 ± 0.03 | [40] | |
49 | NI | 2030 | 0.08 | 0.22 | |||
50 | NI | 2035 | 0.08 | 0.07 | 0.04 | ||
51 | (E)-Nerolidol | 2058 | 2036 | 26.28 ± 0.07 | 33.02 ± 2.11 | 23.16 ± 0.15 | [28] |
52 | δ-Octalactone | 2085 | 1967 | 0.06 | [48] | ||
53 | (Z)-dihydro-Apofarnesol | 2124 | 2137 | 7.58 ± 0.03 | 7.7 ± 0.13 | 8.62 ± 1.58 | [49] |
Total identified (%) | 97.96 | 97.78 | 99.62 | ||||
Hydrocarbon sesquiterpenes (%) | 40.00 | 39.75 | 52.57 | ||||
Oxygenated sesquiterpenes (%) | 26.40 | 33.21 | 23.81 | ||||
Oxygenated monoterpenes (%) | 11.20 | 7.30 | 6.45 | ||||
Hydrocarbon monoterpenes (%) | 9.30 | 4.96 | 5.92 | ||||
Alcohols (%) | 8.64 | 8.83 | 9.12 | ||||
Aldehydes (%) | 0.07 | 2.43 | |||||
NI | 2.04 | 2.33 | 0.38 |
Compounds | Odor | Biological Properties | Ref. |
---|---|---|---|
(E,E)-α-Farnesene | Floral—green apple | Antimicrobial and antifungal activities. | [50] |
(E)-Nerolidol | Woody | Antioxidant, antifungal, and antimicrobial activity, gastroprotective, cytotoxic. | [51,52] |
(E)-β-Ocimene | Sweet, herbal | Anti-inflammatory, antibiotic, and antioxidant activities. | [53,54] |
Linalool | Floral, lavender-like | Antioxidant and antibacterial activity. | [53,55,56] |
(Z)-dihydro-apofarnesol | Not reported | Not reported | |
Perillene | Not reported | Not reported |
Enantiomeric Compounds | RI c | Distribution % | e.e % |
---|---|---|---|
(1R,5R)-(+)-α-pinene | 924 ± 0.9 | 100 | 100 |
(S)-(−)-limonene | 1051 ± 0.7 | 100 | 100 |
(S)-(+)-Linalool | 1179 ± 0.6 | 100 | 100 |
(1S,2R,6R,7R,8R)-(+)-α-copaene | 1322 ± 0.02 | 100 | 100 |
(S)-(+)-(E)-nerolidol | 1683 ± 1.2 | 99.85 | 99.7 |
(R)-(−)-(E)-nerolidol | 1701 ± 1.7 | 0.14 |
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Calva, J.; Celi, J.; Benítez, Á. Analysis of the Volatile and Enantiomeric Compounds Emitted by Plumeria rubra L. Flowers Using HS-SPME–GC. Plants 2024, 13, 2367. https://doi.org/10.3390/plants13172367
Calva J, Celi J, Benítez Á. Analysis of the Volatile and Enantiomeric Compounds Emitted by Plumeria rubra L. Flowers Using HS-SPME–GC. Plants. 2024; 13(17):2367. https://doi.org/10.3390/plants13172367
Chicago/Turabian StyleCalva, James, Jhoyce Celi, and Ángel Benítez. 2024. "Analysis of the Volatile and Enantiomeric Compounds Emitted by Plumeria rubra L. Flowers Using HS-SPME–GC" Plants 13, no. 17: 2367. https://doi.org/10.3390/plants13172367