Chemical Composition and Biological Activities of Essential Oils of Four Asarum Species Growing in Vietnam
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemical Composition of the Essential Oils
2.2. Antimicrobial Activity of the EOs
2.3. Antioxidant Activity of the EOs
2.4. Anti-Inflammatory Activity of the EOs
3. Materials and Methods
3.1. Plant Materials
3.2. Extraction the EOs
3.3. Analyzing Chemical Constituents of the Essential Oils
3.4. Antimicrobial Assays
3.5. Antioxidant Assays
3.6. Anti-Inflammatory Assays
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Sample Availability
References
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No. | Chemical Name | Formula | A. geophilum | A. yentunensis | A. splendens | A. cordifolium | |||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
a RI | Time | b RI | %FID | Time | b RI | %FID | Time | b RI | %FID | Time | b RI | %FID | |||
1 | α-pinene | C10H16 | 932 | 10.01 | 938 | 0.33 | 10.37 | 939 | 0.84 | 10.36 | 939 | 0.84 | 10.70 | 939 | 0.56 |
2 | camphene | C10H16 | 946 | - | - | - | 10.87 | 955 | 0.39 | 10.86 | 955 | 0.28 | 11.21 | 956 | 0.38 |
3 | β-pinene | C10H16 | 986 | 11.36 | 983 | 1.45 | 11.74 | 984 | 0.91 | 11.74 | 984 | 4.71 | 12.11 | 985 | 0.96 |
4 | myrcene | C10H16 | 988 | - | - | - | - | - | - | 11.95 | 991 | 0.15 | 12.32 | 992 | 0.21 |
5 | α-phelandren | C10H16 | 1010 | 12.17 | 1009 | 0.13 | - | - | - | 12.55 | 1010 | 0.15 | 12.93 | 1010 | 0.79 |
6 | δ-3-carene | C10H16 | 1015 | - | - | - | 12.77 | 1016 | 0.39 | - | - | - | 13.15 | 1017 | 0.83 |
7 | o-cymene | C10H14 | 1022 | 12.82 | 1028 | 0.17 | - | - | - | 13.20 | 1029 | 1.22 | 13.60 | 1030 | 1.80 |
8 | limonene | C10H16 | 1030 | 12.97 | 1033 | 0.18 | - | - | - | 13.36 | 1034 | 0.55 | 13.75 | 1034 | 1.87 |
9 | β-phelandrene | C10H16 | 1031 | - | - | - | - | - | - | 13.41 | 1035 | 0.33 | 13.82 | 1036 | 0.31 |
10 | eucalyptol | C10H18O | 1032 | - | - | - | - | - | - | 13.48 | 1037 | 0.16 | - | - | - |
11 | (Z)-β-ocimene | C10H16 | 1039 | - | - | - | 13.49 | 1038 | 0.13 | - | - | - | 13.88 | 1038 | 1.33 |
12 | (E)-β-ocimene | C10H16 | 1050 | - | - | - | 13.87 | 1049 | 0.42 | - | - | - | 14.26 | 1049 | 0.34 |
13 | terpinolene | C10H16 | 1094 | 15.02 | 1093 | 0.20 | 15.43 | 1094 | 0.13 | - | - | - | |||
14 | linalool | C10H18O | 1095 | 15.27 | 1101 | 0.18 | 15.67 | 1101 | 3.19 | - | - | - | 16.10 | 1102 | 0.20 |
15 | exo-fenchol | C10H18O | 1118 | 15.95 | 1120 | 0.13 | - | - | - | - | - | - | - | - | - |
16 | borneol | C10H18O | 1171 | 17.84 | 1174 | 0.15 | 18.25 | 1175 | 0.31 | - | - | - | - | - | - |
17 | terpinen-4-ol | C10H18O | 1184 | 18.20 | 1184 | 0.30 | - | - | - | 18.61 | 1185 | 0.12 | - | - | - |
18 | α-terpineol | C10H18O | 1195 | 18.65 | 1197 | 4.07 | - | - | - | 19.04 | 1197 | 0.26 | - | - | - |
19 | thymol methyl ether | C11H16O | 1232 | - | - | - | - | - | - | 20.27 | 1233 | 0.13 | - | - | - |
20 | geranial | C10H16O | 1271 | - | - | - | - | - | - | 21.66 | 1273 | 0.18 | - | - | - |
21 | bornyl acetate | C12H20O2 | 1289 | 21.94 | 1293 | 0.23 | - | - | - | 22.36 | 1294 | 1.08 | 22.85 | 1295 | 0.23 |
22 | safrole | C10H10O2 | 1293 | - | - | - | 22.59 | 1300 | 64.74 | - | - | - | - | - | - |
23 | n-tridecane | C13H28 | 1300 | 22.14 | 1299 | 0.18 | - | - | - | 22.56 | 1299 | 0.14 | - | - | - |
24 | δ-elemene | C15H24 | 1343 | 23.72 | 1347 | 0.81 | - | - | - | 24.16 | 1348 | 0.30 | - | - | - |
25 | α-terpinyl acetate | C12H20O2 | 1349 | 24.00 | 1355 | 0.35 | - | - | - | - | - | - | |||
26 | endo-isocamphanyl acetate | C11H18O2 | 1350 | - | - | - | - | - | - | 24.43 | 1356 | 1.01 | - | - | - |
27 | geranyl acetate | C12H20O2 | 1379 | - | - | - | - | - | - | 25.35 | 1384 | 0.51 | - | - | - |
28 | α-copaene | C15H24 | 1394 | 25.07 | 1388 | 0.42 | - | - | - | 25.53 | 1389 | 0.46 | 26.00 | 1390 | 0.50 |
29 | cis-β-elemene | C15H24 | 1396 | 25.54 | 1402 | 2.75 | - | - | - | 25.99 | 1404 | 3.48 | 26.45 | 1404 | 1.84 |
30 | methyl eugenol | C11H14O2 | 1403 | - | - | - | 26.09 | 1407 | 1.22 | - | - | - | 26.58 | 1408 | 2.16 |
31 | β-caryophyllene | C15H24 | 1434 | 26.60 | 1436 | 8.05 | 27.03 | 1437 | 0.29 | 27.07 | 1438 | 9.52 | |||
32 | γ-elemene | C15H24 | 1440 | 26.84 | 1444 | 0.68 | - | - | - | - | - | - | - | - | - |
33 | α-trans-bergamotene | C15H24 | 1443 | - | - | - | 27.31 | 1446 | 0.67 | 27.32 | 1446 | 1.71 | - | - | - |
34 | β-gurjunene | C15H24 | 1446 | 27.01 | 1449 | 1.66 | - | - | - | 27.48 | 1451 | 4.06 | - | - | - |
35 | aromadendrene | C15H24 | 1449 | 27.20 | 1455 | 0.61 | - | - | - | 27.66 | 1457 | 0.60 | - | - | - |
36 | (Z)-β-farnesene | C15H24 | 1451 | - | - | - | 27.78 | 1461 | 2.81 | 27.79 | 1461 | 0.23 | - | - | - |
37 | (E)-β-farnesene | C15H24 | 1460 | - | - | - | 27.92 | 1465 | 0.19 | - | - | - | - | - | - |
38 | α-humulene | C15H24 | 1471 | 27.67 | 1470 | 3.87 | 28.11 | 1471 | 0.55 | 28.14 | 1472 | 3.72 | - | - | - |
39 | 9-epi-(E)-caryophyllene | C15H24 | 1474 | 27.95 | 1479 | 18.43 | - | - | - | 28.43 | 1481 | 15.76 | - | - | - |
40 | γ-curcumene | C15H24 | 1481 | - | - | - | 28.66 | 1488 | 0.24 | - | - | - | - | - | - |
41 | γ-muurolene | C15H24 | 1483 | - | - | - | - | - | - | 28.71 | 1490 | 0.59 | - | - | - |
42 | ar-curcumene | C15H24 | 1484 | - | - | - | - | - | - | 28.75 | 1491 | 0.63 | - | - | - |
43 | germacrene D | C15H24 | 1496 | 28.49 | 1496 | 0.56 | - | - | - | 28.95 | 1498 | 1.21 | 29.44 | 1499 | 1.00 |
44 | n-pentadecane | C15H32 | 1500 | 28.58 | 1499 | 1.10 | - | - | - | 29.03 | 1500 | 0.87 | - | - | - |
45 | (E)-methyl isoeugenol | C11H14O2 | 1501 | - | - | - | 29.05 | 1501 | 0.27 | - | - | - | - | - | - |
46 | β-selinene | C15H24 | 1502 | 28.69 | 1503 | 0.60 | - | - | - | 29.16 | 1505 | 1.71 | 29.62 | 1505 | 0.17 |
47 | δ-selinene | C15H24 | 1503 | - | - | - | - | - | - | - | - | - | 29.65 | 1507 | 0.17 |
48 | trans-muurola-4(14),5-diene | C15H24 | 1503 | - | - | - | - | - | - | 29.32 | 1510 | 0.94 | - | - | - |
49 | viridiflorene | C15H24 | 1505 | 28.93 | 1511 | 1.48 | - | - | - | - | - | - | - | - | - |
50 | γ-amorphene | C15H24 | 1508 | - | - | - | - | - | - | - | - | - | 29.82 | 1512 | 0.33 |
51 | cis-bicyclogermacrene | C15H24 | 1510 | 28.98 | 1512 | 4.46 | - | - | - | - | - | - | 29.91 | 1515 | 0.73 |
52 | (E,E)-α-farnesene | C15H24 | 1511 | - | - | - | 29.39 | 1512 | 0.36 | - | - | - | - | - | - |
53 | trans-bicyclogermacrene | C15H24 | 1512 | - | - | - | 29.42 | 1513 | 0.73 | 29.47 | 1515 | 7.50 | - | - | - |
54 | β-bisabolene | C15H24 | 1514 | - | - | - | - | - | - | 29.55 | 1518 | 1.65 | - | - | - |
55 | α-bulnesene | C15H24 | 1517 | - | - | - | - | - | - | 29.64 | 1521 | 0.14 | 30.13 | 1522 | 0.20 |
56 | cuparene | C15H22 | 1518 | - | - | - | - | - | - | 29.74 | 1524 | 0.16 | - | - | - |
57 | sesquicineole | C15H26O | 1521 | - | - | - | 29.80 | 1526 | 15.34 | - | - | - | - | - | - |
58 | γ-cadinene | C15H24 | 1524 | - | - | - | - | - | - | 29.91 | 1530 | 0.49 | 30.44 | 1533 | 0.27 |
59 | myristicin | C11H14O2 | 1529 | - | - | - | 29.95 | 1531 | 0.31 | - | - | - | - | - | - |
60 | β-sesquiphellandrene | C15H24 | 1531 | - | - | - | 30.03 | 1534 | 0.16 | - | - | - | - | - | - |
61 | δ-cadinene | C15H24 | 1533 | 29.65 | 1535 | 0.60 | - | - | - | 30.12 | 1537 | 0.72 | 30.58 | 1538 | 0.41 |
62 | zonarene | C15H24 | 1537 | - | - | - | - | - | - | 30.20 | 1540 | 0.24 | - | - | - |
63 | α-bisabolene | C15H24 | 1544 | - | - | - | - | - | - | - | - | - | 31.00 | 1552 | 1.18 |
64 | selina-4(15),7(11)-diene | C15H24 | 1545 | 30.15 | 1552 | 1.02 | - | - | - | 30.61 | 1553 | 1.18 | - | - | - |
65 | selina-3,7(11)-diene | C15H24 | 1560 | 30.36 | 1559 | 0.41 | - | - | - | 30.82 | 1561 | 1.46 | - | - | - |
66 | elemol | C15H26O | 1562 | 30.43 | 1561 | 0.41 | - | - | - | - | - | - | - | - | - |
67 | elemicin | C12H16O2 | 1565 | - | - | - | - | - | - | - | - | - | 31.43 | 1566 | 77.20 |
68 | (E)-nerolidol | C15H26O | 1569 | 30.64 | 1568 | 0.47 | 31.07 | 1569 | 0.41 | 31.08 | 1569 | 0.79 | 31.60 | 1572 | 0.32 |
69 | germacrene B | C15H24 | 1572 | 30.86 | 1575 | 0.43 | - | - | - | 31.33 | 1578 | 0.60 | - | - | - |
70 | isoelemicin | C12H16O2 | 1577 | - | - | - | 31.33 | 1578 | 0.32 | - | - | - | - | - | - |
71 | 4-epi-maaliol | C15H26O | 1577 | 31.17 | 1586 | 0.67 | - | - | - | - | - | - | - | - | - |
72 | scapanol | C15H26O | 1580 | - | - | - | - | - | - | - | - | - | 32.32 | 1596 | 0.33 |
73 | spathulenol | C15H24O | 1593 | 31.44 | 1595 | 1.24 | - | - | - | 31.90 | 1597 | 1.21 | - | - | - |
74 | viridiflorol | C15H26O | 1595 | 31.65 | 1602 | 2.16 | - | - | - | - | - | - | - | - | - |
75 | caryophyllene oxide | C15H24O | 1599 | - | - | - | - | - | - | 32.12 | 1604 | 1.31 | 32.65 | 1607 | 0.23 |
76 | cubeban-11-ol | C15H26O | 1601 | 31.91 | 1611 | 2.27 | - | - | - | - | - | - | - | - | - |
77 | rosifoliol | C15H26O | 1615 | 32.14 | 1620 | 0.62 | - | - | - | - | - | - | - | - | - |
78 | humulene epoxideII | C15H24O | 1620 | - | - | - | - | - | - | 32.88 | 1631 | 0.14 | - | - | - |
79 | γ-eudesmol | C15H26O | 1646 | 32.96 | 1648 | 0.29 | - | - | - | 33.58 | 1656 | 1.31 | - | - | - |
80 | α-asarone | C12H16O3 | 1650 | - | - | - | - | - | - | - | - | - | 34.09 | 1658 | 0.73 |
81 | α-muurolol | C15H26O | 1654 | - | - | - | - | - | - | - | - | - | 34.18 | 1661 | 0.24 |
82 | α-cadinol | C15H26O | 1665 | 33.58 | 1670 | 0.74 | - | - | - | 33.64 | 1658 | 0.16 | 34.55 | 1674 | 0.84 |
83 | neo-intermedeol | C15H26O | 1670 | 33.67 | 1674 | 1.01 | - | - | - | - | - | - | - | - | - |
84 | β-asarone | C12H16O3 | 1678 | - | - | - | 34.38 | 1684 | 0.98 | - | - | - | 34.88 | 1686 | 0.14 |
85 | eudesm-7(11)-en-4-ol | C15H26O | 1709 | 34.90 | 1718 | 13.41 | - | - | - | 35.40 | 1721 | 14.21 | - | - | - |
86 | (Z)-ligustilide | C12H14O2 | 1741 | - | - | - | - | - | - | 36.29 | 1755 | 0.48 | - | - | - |
87 | n-tetradecanoic acid | C14H28O | 1759 | 35.97 | 1758 | 0.18 | - | - | - | - | - | - | - | - | - |
88 | isophytol | C20H40O | 1946 | 40.86 | 1949 | 0.12 | - | - | - | - | - | - | - | - | - |
89 | n-hexadecanoic acid | C16H32O2 | 1959 | 41.17 | 1962 | 1.31 | - | - | - | - | - | - | - | - | - |
90 | phytol | C20H40O | 2122 | 44.81 | 2117 | 7.23 | - | - | - | - | - | - | - | - | - |
91 | linoleic acid | C18H32O | 2132 | 45.30 | 2139 | 2.45 | - | - | - | - | - | - | - | - | - |
92 | linolenic acid | C18H32O | 2143 | 45.44 | 2145 | 2.31 | - | - | - | - | - | - | - | - | - |
Monoterpene hydrocarbons | 5 (2.46%) | 7 (3.21%) | 7 (7.01%) | 10 (7.58%) | |||||||||||
Oxigenated monoterpenes | 7 (5.41%) | 2 (3.5%) | 8 (3.45%) | 2 (0.43%) | |||||||||||
Sesquiterpene hydrocarbons | 17 (46.84%) | 9 (6.0%) | 25 (59.06%) | 11 (6.53%) | |||||||||||
Oxigenated sesquiterpenes | 11 (23.29%) | 2 (15.75%) | 7 (19.13%) | 5 (1.96%) | |||||||||||
Derivatives of benzene (benzenoids) | 1 (0.17%) | 6 (67.84%) | 1 (1.22%) | 5 (82.03%) | |||||||||||
Others | 8 (14.88%) | - | 3 (1.49%) | - | |||||||||||
Total | 93.05% | 96.30% | 91.36% | 98.78% |
Sample | MIC (μg/mL) | |||||||
---|---|---|---|---|---|---|---|---|
EC | PA | BS | SA | AN | FO | SC | CA | |
A. geophilum EO | 200 | 200 | - | - | - | 200 | 200 | - |
A. yentunensis EO | 200 | - | - | 100 | 200 | - | - | 200 |
A. splendens EO | 200 | - | - | 200 | - | 200 | - | - |
A. cordifolium EO | 200 | - | 100 | - | - | - | - | 200 |
No. | Sample | SC(%) Values | SC50 Values (µg/mL) |
---|---|---|---|
Positive control: ascorbic acid | 81.55 ± 0.9 | 13.26 | |
Negative control [DPPH/EtOH+ DMSO] | 0.0 ± 0.0 | - | |
1 | A. geophilum EO | 63.34 ± 1.0 | 28.57 |
2 | A. yentunensis EO | 51.58 ± 0.5 | 50.24 |
3 | A. splendens EO | 34.24 ± 1.4 | >100 |
4 | A. cordifolium EO | 57.86 ± 0.8 | 39.62 |
No. | Sample * | The Percentages of Inhibition of NO Production (%) | The Percentages of Cell Life (%) | IC50 Values |
---|---|---|---|---|
Positive control: Cardamonin | 85.40 ± 0.7 | 71.80 ± 0.5 | 2.33 µM | |
Negative control | 100.00 ± 0.8 | 100.99 ± 1.0 | - | |
LPS | 0.00 ± 0.0 | - | - | |
1 | A. geophilum EO | 58.20 ± 0.4 | 78.05 ± 0.8 | 40.35 µg/mL |
2 | A. yentunensis EO | 53.14 ± 1.6 | 66.87 ± 1.5 | 49.87 µg/mL |
3 | A. splendens EO | 69.58 ± 1.3 | 81.85 ± 0.9 | 21.68 µg/mL |
4 | A. cordifolium EO | 40.87 ± 0.6 | 60.65 ± 1.4 | 66.37 µg/mL |
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Minh, P.T.H.; Tuan, N.T.; Van, N.T.H.; Bich, H.T.; Lam, D.T. Chemical Composition and Biological Activities of Essential Oils of Four Asarum Species Growing in Vietnam. Molecules 2023, 28, 2580. https://doi.org/10.3390/molecules28062580
Minh PTH, Tuan NT, Van NTH, Bich HT, Lam DT. Chemical Composition and Biological Activities of Essential Oils of Four Asarum Species Growing in Vietnam. Molecules. 2023; 28(6):2580. https://doi.org/10.3390/molecules28062580
Chicago/Turabian StyleMinh, Pham Thi Hong, Nguyen Thuong Tuan, Nguyen Thi Hong Van, Hoang Thi Bich, and Do Tien Lam. 2023. "Chemical Composition and Biological Activities of Essential Oils of Four Asarum Species Growing in Vietnam" Molecules 28, no. 6: 2580. https://doi.org/10.3390/molecules28062580