A Discovery-Based Metabolomic Approach Using UPLC-Q-TOF-MS/MS Reveals Potential Antimalarial Compounds Present in Artemisia annua L.
Abstract
:1. Introduction
2. Results
2.1. Antimalarial Activity of Different Extracts of Artemisia annua L.
2.2. UPLC-Q-TOF-MSE Qualitative Analysis
2.3. Multivariate Statistical Analysis
2.3.1. PCA
2.3.2. OPLS-DA
3. Materials and Methods
3.1. Plant Material
3.2. Chemicals
3.3. Sample Preparation
3.3.1. Ether Extracts
3.3.2. Ether Neutral Dry
3.3.3. Ether Neutral Dry without Artemisinin
3.4. Animal Experiment
3.5. UPLC-Q-TOF-MS Measurement
3.6. Data Analysis by UNIFI Platform
3.7. Multivariate Statistical Analysis
4. Discussion
5. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
ACTs | Artemisinin-based combination therapies |
ART | Artemisinin |
ArtL(M/H) | Artemisia annua L. with low/medium/high content of artemisinin |
ArtL(M/H)-Et2O | Ether extract of Artemisia annua L. with low/medium/high content of artemisinin |
2% ArtL(M/H)-Et2O | Neutral dry of ArtL(M/H)-Et2O |
2% AL(M/H)E-NA | Neutral dry of 2% ArtL(M/H)-Et2O without artemisinin |
AHE-NA | ArtH-Et2O without artemisinin |
PE | Petroleum ether |
EA | Ethyl acetate |
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Group | Mean Content/% | RSD/% |
---|---|---|
ArtL-Et2O | 1.84 | 0.18 |
2% ArtL-Et2O | 0.62 | 0.29 |
ArtM-Et2O | 13.60 | 2.68 |
2% ArtM-Et2O | 11.77 | 1.77 |
ArtH-Et2O | 16.69 | 2.58 |
2% ArtH-Et2O | 10.23 | 3.93 |
NO. | Component Name | Neutral Mass (Da) | Observed m/z | RT (min) | MS/MS |
---|---|---|---|---|---|
1 | Artenniun D | 282.1467 | 283.1655 | 2.70 | 265.1551, 247.1409, 219.1470 |
281.1600 * | 265.1625, 251.1826, 181.0640 | ||||
2 | Chrysospleno D | 360.0845 | 361.0916 | 3.07 | 345.0744, 303.0629 |
359.1078 * | 344.0792, 329.0523 | ||||
3 | Casticin | 374.1002 | 375.1073 | 3.90 | 360.1020, 345.0782, 317.0796 |
373.1233 * | 358.0995, 343.0695 | ||||
4 | 1-Oxo-2-[3-butanone]-3-methyl-6-[2-propanoic acid]-cyclohexane methyl ester | 268.1675 | 291.1691 | 4.26 | 219.1500, 191.1509, 173.1407, 145.1078 |
5 | Artenniun B | 248.1412 | 249.1589 | 4.47 | 231.1490, 185.1413 |
6 | Artemisinin | 282.1467 | 283.1655 | 5.10 | 265.1551, 247.1441, 237.1582, 229.1470, 219.1500 |
7 | Artenniun C | 266.1518 | 267.1716 | 5.24 | 249.1589, 231.1490, 207.1467 |
265.1659 * | 116.9371 | ||||
8 | Artenniun I | 234.1620 | 235.1800 | 7.21 | 217.1672, 189.1727, 161.1393 |
233.1733 * | 116.9371 | ||||
9 | Dihydroartemisinic acid | 236.1776 | 237.1960 | 8.53 | 219.1833, 201.1731, 163.1562 |
235.1883 * | |||||
10 | Artemisinic acid | 234.1620 | 235.1800 | 9.20 | 217.1672, 199.1551, 189.1727 |
233.1733 * |
NO. | Component Name | Neutral Mass (Da) | Observed m/z | Mass Error (mDa) | RT (min) | MS/MS |
---|---|---|---|---|---|---|
Flavonoids | ||||||
1 | Patuletin-3-O-glucoside | 494.1060 | 495.1092 | −4.2 | 1.24 | 333.0584, 318.0336, 287.0535 |
2 | Astragalin | 448.1006 | 447.1125 * | 0.6 | 1.27 | 285.1470, 257.1145 |
3 | Quercetin | 302.0427 | 303.0488 | −1.1 | 2.18 | 287.0543 |
4 | 4H-1-Benzopyran-4-one, 5,7,8-trihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-methoxy- | 346.0689 | 347.0757 | −0.5 | 2.41 | 317.0650 |
5 | Patuletin | 332.0532 | 333.0591 | −1.4 | 2.22 | 318.0346, 287.0545 |
332.0532 | 331.0459 * | 0.0 | 2.25 | 285.0410 | ||
6 | Kaempferol | 286.0477 | 287.0541 | −0.9 | 2.67 | 153.0173, 229.0476 |
286.0477 | 285.0400 * | −0.5 | 2.73 | 151.0031 | ||
7 | Chrysoeriol | 300.0634 | 301.0699 | −0.8 | 2.70 | 286.0465, 258.0513, 257.0406 |
8 | Rhamnetin | 316.0583 | 317.0645 | −1.1 | 2.77 | 302.042, 270.0513 |
316.0583 | 315.0504 * | −0.7 | 2.82 | 299.01, 243.0306 | ||
9 | Axillarin | 346.0689 | 347.0753 | −0.8 | 2.84 | 289.1403 |
346.0689 | 345.0615 * | 0.0 | 2.86 | 314.0454, 299.0194 | ||
10 | 2,4′,5′-Trihydroxy-5′6,7-trimethoxyflavone | 360.0845 | 361.0916 | −0.2 | 3.07 | 345.0604, 328.0575 |
11 | Chrysosplenol D | 360.0845 | 361.0916 | −0.2 | 3.07 | 361.1007, 362.1008, 363.1022, 345.0730, 328.0613 |
12 | Eupatin | 360.0845 | 361.0913 | −0.5 | 3.62 | 331.0854, 291.1586, 233.1570 |
13 | 4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy- | 330.0740 | 331.0805 | −0.7 | 3.63 | 331.0854, 316.0571 |
14 | Penduletin | 344.0896 | 345.0963 | −0.6 | 3.76 | 328.0634 |
344.0896 | 343.0824 * | 0.1 | 3.79 | |||
15 | Casticin | 374.1002 | 375.1073 | −0.2 | 3.90 | 377.1171, 376.1163, 375.1168 |
16 | Chrysosplenetin | 374.1002 | 397.0887 | −0.7 | 3.91 | 397.0939, 375.1168, 317.0657 |
17 | Quercetagetin-6,7,3′,4′-tetramethylether | 374.1002 | 375.1076 | 0.1 | 4.00 | |
18 | Cirsimaritin | 314.0790 | 315.0846 | −1.7 | 4.38 | 300.0607, 285.0376 |
19 | Mikanin | 344.0896 | 345.0967 | −0.2 | 4.53 | 330.0771, 271.1332, 205.1633 |
344.0896 | 343.0819 * | −0.4 | 4.57 | 328.0585, 313.0351, 285.0435 | ||
20 | Artemetin | 388.1158 | 389.1231 | 0.0 | 4.76 | 331.0806, 313.0702283.0598, 267.0644, 135.0436 |
21 | Rhamnocitrin | 300.0634 | 301.0705 | −0.2 | 5.64 | |
22 | 5-Hydroxy-3,4′,6,7-tetramethoxyflavone | 358.1053 | 359.1125 | 0.0 | 5.64 | 359.1201 |
23 | 4H-1-Benzopyran-4-one, 3-hydroxy-6,7-dimethoxy-2-(4-methoxyphenyl)- | 328.0947 | 329.1020 | 0.0 | 6.92 | 314.0840 |
Sesquiterpenoids | ||||||
1 | Arteannuin M | 268.1675 | 291.1563 | −0.4 | 2.27 | 235.1312, 217.1199, 207.1371 |
2 | Artemisinin B | 266.1518 | 265.1445 * | −0.1 | 2.41 | 251.1292, 241.1448, 235.1341 |
3 | Artenniun D | 282.1467 | 281.1389 * | −0.5 | 2.61 | 219.1348, 191.1049, 172.8616 |
4 | Artemisin | 262.1205 | 263.1262 | −1.6 | 2.68 | 231.1366, 203.1422, 161.0951 |
5 | seco-Cadinane | 266.1518 | 311.1493 * | −0.7 | 2.71 | 237.1488, 219.1002, 175.1120 |
6 | Dihydroxycadinanolide | 266.1518 | 265.1447 * | 0.1 | 2.75 | 247.1341, 231.1396, 219.1021 |
7 | 1-Oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanoic acid]-cyclohexane | 254.1518 | 277.1409 | −0.1 | 2.83 | 237.1582, 209.1525, 151.1111 |
254.1518 | 253.1445 * | 0.0 | 2.86 | 183.1025, 109.0670, 235.1340 | ||
8 | α-Hydroxysantonin | 262.1205 | 263.1213 | −6.5 | 3.16 | 157.0635, 107.0488 |
9 | Arteannuin L | 250.1569 | 273.1456 | −0.5 | 3.24 | 233.1528, 189.1261, 187.1474 |
10 | Dihydroartemisinic acid hydroperoxide | 268.1675 | 267.1600 * | −0.1 | 3.27 | 249.1496, 221.1547, 203.1440 |
11 | Arteannuin G | 282.1467 | 283.1504 | −3.6 | 3.39 | 233.1131, 163.0741, 125.0936 |
12 | 4α,5α-Epoxy-6α-hydroxy amorphan-12-oic acid | 268.1675 | 267.1597 * | −0.5 | 3.46 | 251.1648, 223.1343, 205.1593 |
13 | Norannuic acid formyl ester 15-nor-10-Hydroxy-oplopan-4-oic acid | 240.1725 | 285.1708 * | 0.1 | 3.65 | 223.1343, 177.0919, 211.1345 |
14 | Arteannuin K | 250.1569 | 249.1487 * | −0.9 | 3.80 | 231.1391, 217.1231, 202.0994 |
15 | 4-Amorphene-3,7-diol (3α,7α), acetate- | 280.2038 | 303.1906 | −2.5 | 4.04 | 249.1478, 231.1362, 203.1417 |
16 | 4-Amorphene-3,7-diol (3α,7α) | 238.1933 | 261.1807 | −1.8 | 4.10 | 209.1517, 202.1641, 175.1106 |
17 | 1-Oxo-2-[3-butanone]-3-methyl-6-[2-propanoic acid]-cyclohexane methyl ester | 268.1675 | 267.1599 * | −0.3 | 4.17 | 253.1449, 235.1339, 183.1024 |
18 | 4-Amorphen,3,11-diol | 238.1933 | 261.1825 | 0.0 | 4.22 | 187.1473, 159.1164, 129.0690 |
19 | α-Epoxy-dihydroartemisinic | 252.1725 | 251.1351 * | −0.2 | 4.26 | 237.1491, 205.1596, 191.1440 |
20 | Arteannuin E | 250.1569 | 251.1634 | −0.8 | 4.29 | 233.1510, 215.1402, 191.1041 |
21 | Artenniun B | 248.1412 | 271.1300 | −0.4 | 4.47 | 205.1581 |
22 | 3α,15-Dihydroxy cedrane | 238.1933 | 261.1831 | 0.6 | 4.60 | 209.1516, 175.1107, 147.1162 |
23 | Unknown | 232.1463 | 233.1531 | −0.6 | 4.83 | 215.1416, 187.1472, 145.1004 |
24 | Arteannuin F | 250.1569 | 249.1488 * | −0.8 | 4.84 | 235.1340, 231.1385, 209.1179 |
25 | Abscisic acid | 264.1362 | 265.1433 | −0.2 | 4.85 | |
264.1362 | 263.1288 * | −0.1 | 4.85 | |||
26 | 5α-Hydroperoxy-eudesma-4(15),11-diene | 236.1776 | 237.1842 | −0.7 | 5.05 | 221.1514, 219.1833, 201.1731 |
27 | Cubenol | 222.1984 | 261.1658 | 4.3 | 5.11 | 145.1007, 128.0618, 105.0697 |
28 | Artemisinin | 282.1467 | 281.1395 * | 0.0 | 5.17 | 265.1451, 253.1448, 219.1389 |
29 | Arteanniun A | 206.1307 | 207.1375 | −0.5 | 5.24 | 193.1578, 161.1315, 133.1007 |
30 | β-copaen-4α-ol | 234.1984 | 273.1659 | 4.3 | 5.25 | 203.1420, 185.1314, 159.1162 |
31 | 3α-Hydroxy-4α,5α-epoxy-7-oxo-(8[7→6]-abeo-amorphane | 238.1569 | 239.1632 | −1.0 | 5.26 | 203.1421, 179.1056, 133.1007 |
238.1569 | 283.1549 * | −0.2 | 5.16 | 219.1389, 183.1025, 149.0969 | ||
32 | Artenniun C | 266.1518 | 265.1444 * | −0.1 | 5.30 | 247.134, 233.1175, 203.1435 |
33 | α-Epoxyartemisinic acid | 250.1569 | 249.1494 * | −0.3 | 5.35 | 205.1596 |
34 | artemisitene | 280.1311 | 281.1353 | −3.1 | 5.44 | 247.1314, 209.1523 |
35 | Norannuic acid | 224.1412 | 247.1321 | 1.6 | 5.79 | 209.1525, 163.1107, 131.0848 |
36 | Arteannuin H | 250.1569 | 273.1436 | −2.5 | 6.31 | 203.1415, 189.1258, 147.1158 |
37 | Nortaylorione | 220.1463 | 221.1526 | −1.0 | 6.62 | 163.1105, 139.1106, 135.1156 |
38 | Deoxyarteannuin B | 232.1463 | 233.1531 | −0.6 | 6.69 | |
39 | Annulide | 232.1463 | 233.1531 | −0.6 | 7.00 | 215.1514, 187.1572 |
40 | Spathulenol | 220.1827 | 221.1887 | −1.3 | 7.12 | 203.1789, 175.1476, 123.1156 |
41 | Artenniun I | 234.1620 | 233.1548 * | 0.1 | 7.22 | 176.0819 |
42 | Dihydro-deoxyarteannuin B | 234.1620 | 235.1689 | −0.4 | 7.26 | 189.1628, 161.1322 |
43 | Arteannuin J | 234.1620 | 235.1690 | −0.3 | 7.61 | 217.1577, 189.1625, 161.1320 |
44 | Dihydroartemisinic acid | 236.1776 | 259.1662 | −0.7 | 7.63 | 219.1736, 189.1625, 161.1320 |
45 | 3-Isobutylcadin-4-en-11-ol | 308.2351 | 307.2275 * | −0.4 | 7.70 | 277.2167, 251.1658, 195.1385 |
46 | Nootkatone | 218.1671 | 219.1736 | −0.7 | 8.51 | 203.1415, 163.1103, 123.0791 |
47 | trans-α-bergamotyl acetic anhydride | 276.1725 | 277.1785 | −1.3 | 8.81 | 233.1520, 205.1572, 235.1676 |
48 | Elemyl acetate | 264.2089 | 265.2144 | −1.8 | 9.06 | 233.1522, 205.1572, 191.1410 |
49 | Artemisinic acid | 234.1620 | 235.1675 | −1.8 | 9.19 | 175.1103 |
50 | Artemisinic aldehyde | 218.1671 | 219.1732 | −1.1 | 9.34 | 202.1265 |
51 | Artemisinic acid methyl ester | 248.1776 | 293.1794 * | 3.5 | 9.99 | 221.1545, 177.1279 |
52 | Occidentalolacetate | 246.1984 | 285.1657 | 4.2 | 10.04 | 189.1627, 163.1109 |
53 | α-Aromadendrene | 204.1878 | 205.1941 | −1.0 | 10.15 | |
54 | 6,7-dehydroartemisinic acid | 232.1463 | 233.1531 | −0.5 | 10.25 | 205.1576, 187.1472, 175.1102 |
55 | 14-Hydroxy-α-humulene | 262.1933 | 307.1920 * | 0.5 | 10.28 | 221.1549, 191.1069, 151.1126 |
56 | 4(15),5,11-Cadinatriene | 202.1722 | 203.1789 | −0.5 | 10.32 | 177.1627, 175.1468, 173.1313 |
57 | 14-Hydroxy-δ-cadinene | 220.1827 | 221.1890 | −1.0 | 10.32 | 203.1788, 173.1316, 161.1316 |
58 | α-Longipinene | 204.1878 | 205.1963 | 1.2 | 10.33 | 191.1799, 175.1473, 161.1316 |
59 | β-Longipinene | 204.1878 | 205.1945 | −0.6 | 10.57 | 187.1470, 158.1039 |
60 | cis-Calamenene | 202.1722 | 203.1789 | −0.5 | 10.71 | 173.0881, 145.1004, 115.0537 |
61 | α-Cubebene | 204.1878 | 205.1945 | −0.6 | 10.99 | 159.11651, 145.10085, 131.0852 |
62 | Cedrylacetate | 264.2089 | 287.1962 | −1.9 | 11.11 | 109.0644 |
63 | Cedra-8(15)-en-9α-ol acetate | 262.1933 | 285.1824 | −0.1 | 11.30 | 231.1364, 219.1331, 173.1317 |
64 | Guaiazulene | 198.1409 | 199.1462 | −1.9 | 11.40 | 185.1308, 143.0842, 128.0613 |
65 | α-Ylangene | 204.1878 | 227.1760 | −1.1 | 11.41 | 161.1318, 147.1163, 129.0689 |
66 | Pregeijerene | 162.1409 | 185.1310 | 1.0 | 11.47 | 131.0846, 119.08495, 105.0694 |
67 | Cedra-8-en-13-ol, acetate | 248.1776 | 271.1640 | −2.8 | 11.54 | 189.1250, 159.1163, 157.1003 |
68 | 1β-Hydroxy-4(15),5-eudesmadiene | 220.1827 | 221.1901 | 0.1 | 11.73 | 207.1731, 180.1464, 146.0806 |
Others | ||||||
1 | 3-Cyclohexene-1-methanol 2-hydroxy-α,α,4-trimethyl-, 1-acetate | 212.1412 | 235.1313 | 0.9 | 5.11 | 105.0697 |
2 | trans-5-Hydroxy-2-isopropenyl-5-methylhex-3-en-1-ol | 170.1307 | 193.1204 | 0.5 | 5.26 | 157.1072, 121.1004, 107.0849 |
3 | 2,6-Octadien-1-ol, 2,6-dimethyl-8-[(tetrahydro-2H-pyran-2-yl)oxy]- | 254.1882 | 253.1810 * | 0.0 | 8.71 | 235.1700, 219.1872, 205.1598 |
4 | 1,10-Oxy-α-myrcene hydroxide | 168.1150 | 191.1039 | −0.3 | 10.25 | 119.0850, 105.0695 |
5 | 2-Cyclohexen-1-ol, 3-methyl-6-(1-methylethylidene)- | 152.1201 | 175.1112 | 1.9 | 10.25 | 135.1221, 119.0850, 109.1001 |
6 | 2,6-Dimethyl-1,3,5,7-octatetraene | 134.1096 | 135.1155 | −1.3 | 10.27 | 107.0850, 105.0695 |
7 | 2-Butenoic acid, 3-methyl-,(1S,2R,4S)-1,7,7-trimethylbicyclo [2.2.1] hept-2-yl ester | 236.1776 | 235.1709 * | 0.5 | 10.30 | 221.1547, 179.1078, 137.0968 |
8 | p-Menth-3-ene | 138.1409 | 161.1319 | 1.8 | 10.34 | 123.1158 |
9 | Menthol | 156.1514 | 195.1143 | −0.3 | 10.75 | 143.0886, 135.1221, 109.1006 |
10 | Borneol isobutyrate | 224.1776 | 247.1683 | 1.5 | 11.11 | 139.0745, 123.0778, 123.0422 |
11 | Myrtenal | 150.1045 | 173.0941 | 0.4 | 11.16 | 121.1004, 105.0696 |
12 | Stigmasterol | 412.3705 | 413.3770 | −0.8 | 11.32 | 217.1570, 199.1466, 147.1159, 128.0613 |
13 | 2-Cyclohexen-1-one, 2-methyl-5-(1-methylcyclopropyl)- | 164.1201 | 187.1091 | −0.2 | 11.33 | |
14 | Lavandulylacetate | 196.1463 | 219.1333 | −2.2 | 11.37 | 122.0793 |
15 | Sabinene | 136.1252 | 159.1158 | 1.4 | 11.39 | 105.0694 |
16 | β-Amyrin acetate | 468.3967 | 491.3903 | 4.4 | 11.44 | 437.3354, 201.1628, 133.1008, 119.0854 |
17 | Bornylacetate | 196.1463 | 219.1344 | −1.1 | 11.55 | |
18 | Carvone | 150.1045 | 173.0938 | 0.1 | 11.57 | 135.1198, 119.0909 |
19 | Fenchol | 154.1358 | 177.1250 | 0.0 | 11.62 | 137.1312, 122.0808 |
20 | (2E)-Hexadecene | 280.3130 | 303.3021 | −0.1 | 11.86 | 163.1466, 135.1158, 121.1004, 107.0851 |
21 | Taraxasterone | 424.3705 | 425.3740 | −3.8 | 12.84 | 409.3410, 201.1623, 161.1314, 133.1003 |
NO. | Primary ID | Neutral Mass (Da) | m/z | Rt (min) | Identification | VIP [1 + 1 + 0] |
---|---|---|---|---|---|---|
Positive ion mode | ||||||
1 | 7.26_178.1355n | 178.1355 | 161.1322 | 7.26 | Arteanniun I | 6.80 |
2 | 7.26_234.1612n | 234.1612 | 235.1684 | 7.26 | Arteanniun I | 6.67 |
3 | 5.11_282.1456n | 282.1456 | 265.1427 | 5.11 | Artemisinin | 6.09 |
4 | 2.85_276.1329n | 254.15181 | 277.1402 | 2.85 | 1-Oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanoic acid]-cyclohexane | 5.64 |
5 | 5.10_246.1244n | 246.1244 | 247.1322 | 5.10 | Artemisinin | 5.44 |
6 | 4.53_345.0959m/z | 345.0959 | 4.53 | Mikanin | 5.34 | |
7 | 5.10_236.1408n | 236.1408 | 219.1375 | 5.10 | Artemisinin | 5.27 |
Negative ion mode | ||||||
8 | 2.55_283.1527m/z | 283.1527 | 2.55 | Arteanniun D | 7.54 | |
9 | 3.44_267.1582m/z | 267.1582 | 3.44 | 4α,5α-Epoxy-6α-hydroxy amorphan-12-oic acid | 7.11 | |
10 | 2.88_254.1498n | 254.1498 | 253.1435 | 2.88 | 1-Oxo-2β-[3-butanone]-3α-methyl-6β-[2-propanoic acid]-cyclohexane | 6.35 |
NO. | Primary ID | Neutral Mass (Da) | m/z | Rt/min | Identification | VIP [1 + 1 + 0] |
---|---|---|---|---|---|---|
1 | 7.26_234.1610n | 234.1610 | 235.1682 | 7.26 | Arteannuin I | 6.76 |
2 | 7.26_178.1353n | 178.1353 | 161.1321 | 7.26 | 6.67 | |
3 | 3.86_250.1558n | 250.1558 | 251.1631 | 3.86 | Arteannuin K | 5.35 |
NO. | Primary ID | Neutral Mass (Da) | m/z | RT (min) | Identification | VIP [1 + 1 + 0] |
---|---|---|---|---|---|---|
1 | 5.64_358.1045n | 358.1045 | 359.1117 | 5.64 | 5-Hydroxy-3,4′,6,7- tetramethoxyflavone | 10.27 |
2 | 3.25_232.1452n | 233.1525 | 3.25 | Arteannuin L | 5.50 | |
3 | 3.25_187.1471 m/z | 187.1471 | 3.25 | 5.71 | ||
4 | 4.75_388.1152n | 388.1152 | 389.1225 | 4.75 | Artemetin | 5.34 |
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Shi, H.; Wang, Z.; Xu, F.; Li, J.; Li, J.; Wang, M. A Discovery-Based Metabolomic Approach Using UPLC-Q-TOF-MS/MS Reveals Potential Antimalarial Compounds Present in Artemisia annua L. Int. J. Mol. Sci. 2022, 23, 14903. https://doi.org/10.3390/ijms232314903
Shi H, Wang Z, Xu F, Li J, Li J, Wang M. A Discovery-Based Metabolomic Approach Using UPLC-Q-TOF-MS/MS Reveals Potential Antimalarial Compounds Present in Artemisia annua L. International Journal of Molecular Sciences. 2022; 23(23):14903. https://doi.org/10.3390/ijms232314903
Chicago/Turabian StyleShi, Henan, Zhuqing Wang, Fujie Xu, Jialin Li, Jing Li, and Manyuan Wang. 2022. "A Discovery-Based Metabolomic Approach Using UPLC-Q-TOF-MS/MS Reveals Potential Antimalarial Compounds Present in Artemisia annua L." International Journal of Molecular Sciences 23, no. 23: 14903. https://doi.org/10.3390/ijms232314903