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. 2024 Mar 15;15:1333167. doi: 10.3389/fphar.2024.1333167

TABLE 2.

Compound list for ZRH identified by HPLC-Q-Exactive-MS/MS analysis.

NO. Compounds tR/min Formula Ionization mode m/z δ/(ppm) Fragment ions Classification
Theoretical Measured
1 Quinic acid 1.04 C7H12O6 [M-H] - 191.05501 191.05330 −8.974 191.05330, 173.04311, 85.02716 Organic acids
2 L(+)-Tartaric acid 1.10 C4H6O6 [M-H]- 149.00806 149.00670 −9.156 149.00670, 103.03772, 87.00642, 74.02245, 72.99093, 59.01182 Organic acids
3 citric acid 1.18 C6H8O7 [M-H] - 191.01862 191.01714 −7.795 191.01714, 173.00621, 111.00628 Organic acids
4 Monoglyceride citrate 2.16 C9H14O9 [M-H]- 265.05540 265.05438 −3.880 265.05438, 173.00641, 111.00632 Esters
5 Gallic acid 3.17 C7H6O5 [M-H]- 169.01314 169.01146 −9.998 169.01146, 125.02191, 127.02626, 97.02721 Organic acids
6 Methyll citrate 3.78 C7H10O7 [M-H]- 205.03427 205.03253 −8.531 205.03253, 173.00592, 143.03229, 111.00626, 87.00640 Esters
7 Gentisic 5.22 C7H6O4 [M-H]- 153.01823 153.01671 −9.967 153.01671, 108.04317, 91.83106 Organic acids
8 3-Phenylpropionic acid 6.40 C9H10O2 [M-H]- 149.05970 149.05824 −9.836 149.05824 Organic acids
9 chlorogenic acid 10.39 C16H18O9 [M-H] - 353.08670 353.08606 −1.837 353.08606, 191.05333 Organic acids
10 Shanzhiside 10.62 C16H24O11 [M-H] - 391.12348 391.12128 −5.645 391.12128, 167.06853 Iridoids
11 Hydroquinone 10.82 C6H6O2 [M + H]+ 111.04405 111.04504 8.861 111.04504, 110.06110, 55.05545 Phenols
12 3,4-Dihydroxybenzoic acid 11.46 C7H6O4 [M-H]- 153.01823 153.01669 −1.545 153.01669, 109.02705, 108.04298 Organic acids
13 Syringaldehyde 11.95 C9H10O4 [M + H]+ 183.06518 183.06668 8.165 183.06668, 155.10754, 140.08000, 123.04501, 95.05024 Aldehydes
14 Gardoside 12.12 C16H22O10 [M-H] - 373.11292 373.11340 1.278 373.11340, 167.03247 Iridoids
15 2-Isoprpryl malic acid 12.14 C7H12O5 [M-H]- 175.06009 175.05847 −9.311 175.05847, 115.03752, 113.05829, 85.06358 Organic acids
16 mussaenosidic acid 12.30 C16H24O10 [M-H] - 375.12857 375.12521 −8.966 375.12521, 213.07413 Organic acids
17 Deacetylasperulosidic acid 12.32 C16H22O11 [M-H] - 389.10783 389.10538 −6.317 389.10538, 165.05289 Iridoids
18 Procyanidin B2 12.60 C30H26O12 [M-H]- 577.13405 577.13843 7.585 577.13843, 179.05315 Flavonoids
19 Caffeic acid 14.16 C9H8O4 [M-H]- 179.03388 179.03238 −8.407 179.03238, 135.04268 Organic acids
20 phenylacetaldehyde 15.52 C8H8O [M + H]+ 121.06479 121.06580 8.330 121.06580, 91.05540, 77.03985, 65.03984 Aldehydes
21 Geniposide 15.55 C17H24O10 [M + Na]+ 411.12726 411.12860 −5.368 411.12860 Iridoids
22 Vanillic acid 15.76 C8H8O4 [M-H]- 167.03388 167.03226 −1.625 167.03226, 152.00893, 108.01902 Organic acids
23 Ethyl gallate 16.10 C9H10O5 [M-H]- 197.04444 197.04298 −7.460 197.04298, 169.01155, 124.01389 Flavonoids
24 Agarotetrol 16.97 C17H18O6 [M + H]+ 319.11761 319.11905 4.497 319.11905, 301.10901, 283.09833, 255.10303, 227.10776, 164,04750 Chromones
25 Hydroxysafflor yellow A 17.19 C27H32O16 [M-H]- 611.16066 611.15735 −5.418 611.15735, 353.06302 Flavonoids
26 Taxifolin 17.67 C15H12O7 [M-H]- 303.04992 303.04843 −4.947 303.04843, 125.02198 Flavonoids
27 Salicylic acid 18.47 C7H6O3 [M-H]- 137.02332 137.02196 −9.929 137.02196, 94.02755, 93.03232, 65.03764 Organic acids
28 Methyl cinnamate 18.51 C10H10O2 [M + H]+ 163.07535 163.07629 5.727 131.05023, 121.10234, 107.05025, 103.05519 Esters
29 Isoquercitrin 18.84 C21H20O12 [M-H] - 463.08710 463.08466 −5.274 463.08466, 301.03217, 255.02670 Flavonoids
30 safflor yellow A 19.39 C27H35O15 [M-H]- 598.18922 598.18524 −6.656 598.18524 Flavonoids
31 Rutin 19.51 C27H30O16 [M-H]- 609.14501 609.14172 −5.403 609.14172, 300.02469, 271.02185 Flavonoids
32 quercetin 19.64 C15H10O7 [M + H]+ 303.04992 303.05182 6.239 303.05182, 229.05084, 257.04620 Flavonoids
33 Ellagic acid 19.97 C14H6O8 [M + H]+ 303.01354 303.01547 6.357 303.01547, 285.00488 Organic acids
34 (-)-Epicatechin 20.61 C15H14O6 [M + H]+ 291.08631 291.08801 5.824 291.08801, 289.07269, 165.05598, 139.04007 Flavonoids
35 Coumarin 20.68 C9H6O2 [M + H]+ 147.04405 147.04503 6.624 147.04503, 119.05021, 103.04573, 95.05064, 91.05537 Coumarins
36 Nicotiflorin 20.69 C27H30O15 [M-H] - 593.15009 593.14716 −4.951 593.14716, 325.06290 Flavonoids
37 Kaempferol 7-O-glucoside 20.93 C21H20O11 [M-H]- 447.09218 447.09146 −1.628 447.09146, 284.03000 Flavonoids
38 Methylellagic acid 21.79 C15H8O8 [M-H]- 315.01354 315.01199 −4.932 315.01199, 300.99188 Organic acids
39 Naringetol 23.73 C15H12O5 [M-H]- 271.06009 271.05881 −1.290 271.05881, 151.00104, 120.05093, 119.04774, 107.01142 Flavonoids
40 D(+)-Camphor 24.88 C10H16O [M + H]+ 153.12739 153.12837 6.389 153.12837, 108.08988, 95.08677, 81.07110, 69.07112, 55.01922 Ketones
41 6-Hydroxy-2-(2-phenylethyl)chromone 25.25 C17H14O3 [M + H]+ 267.10157 267.10294 5.126 267.10294, 176.04791, 161.13408, 137.09688 Chromones
42 apigenin 25.43 C15H10O5 [M-H]- 269.04444 269.04306 −5.166 269.04306 Flavonoids
43 dehydrocholic acid 25.54 C24H34O5 [M-H]- 401.23225 401.23148 −1.921 401.23148 Organic acids
44 Kaempferol 25.57 C15H10O6 [M-H]- 285.03936 285.03790 −5.138 285.03790 Flavonoids
45 5,8-dihydroxy-2-(2-phenylethyl)chromone 25.69 C17H14O4 [M + H]+ 283.09648 283.09808 5.633 283.09808, 192.04300 Chromones
46 Myrcene 26.98 C10H16 [M + H]+ 137.13247 137.13342 6.876 137.13342, 93.07101, 69.07106, 79.05540 Alkenes
47 stearic acid 28.96 C18H36O2 [M-H]- 283.26315 283.26245 −2.495 283.26245 Organic acids
48 Glycocholic acid 29.18 C26H43NO6 [M-H]- 464.30066 464.29800 −5.739 464.29800, 74.02259 Organic acids
49 6-methoxy-2-(2-phenylethyl)chromen-4-one 29.23 C18H16O3 [M + H]+ 281.11722 281.11865 5.084 281.11865, 190.06349, 151.03923 Chromones
50 Deoxycholic acid 30.63 C24H40O4 [M-H]- 391.28428 391.28229 −5.102 391.28229 Organic acids
51 Hyocholic acid 30.85 C24H40O5 [M-H]- 407.27920 407.27710 −5.158 407.27710 Organic acids
52 2,6-Dimethoxyphenol 31.21 C8H10O3 [M + H]+ 155.07027 155.07137 7.089 155.07137, 154.96363, 139.04002, 111.04516, 96.05373, 93.03458 Phenols
53 2-(2-phenylethyl)chromon 31.70 C17H14O2 [M + H]+ 251.10665 251.10797 5.232 251.10797, 173.13361, 161.13316, 121.08686 Chromones
54 γ-Linolenic acid 32.43 C18H30O2 [M + H]+ 279.23185 279.23428 8.678 279.23428, 262.22650, 261.22302, 243.21196, 195.13866 Fatty acids
55 Chenodeoxycholic acid 32.78 C24H40O4 [M-H]- 391.28428 391.28214 −5.485 391.28214 Organic acids
56 beta-elemene 33.01 C15H24 [M + H]+ 205.19507 205.19635 6.202 205.19635, 81.07110, 67.05546, 55.05541 Alkenes
57 Elaidic acid 35.24 C18H34O2 [M + H]+ 283.26315 283.26498 6.436 283.26498, 109.10230, 95.08684, 81.07112, 69.07116, 57.07118 Fatty acids
58 Oleanolic acid 35.91 C30H48O3 [M-H]- 455.35197 455.34949 −5.450 455.34949 Triterpenoids
59 palmitic acid 37.63 C16H32O2 [M-H]- 255.23185 255.23038 −5.786 255.23038 Fatty acids
60 Icosanoic acid 38.43 C20H40O2 [M-H]- 311.29445 311.29291 −4.969 311.29291, 119.14525 Organic acids