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. 2019 Jul 23;24(14):2658. doi: 10.3390/molecules24142658

Table 1.

Summary of metabolites of eupatorin in vivo and in vitro.

Metabolites ID Composition Formula m/z Error (ppm) R.T. (min) MS/MS Fragments Clog P Score (%) Plasma Bile Urine Feces RLMs RIF
M1 Loss of CH2 [M-H]− C17H14O7 329.0660 −2.0 9.93 314.0427, 313.0384, 299.0188, 285.0371, 207.7129 2.26422 83.3 - - +a,b + a,b +I,II + a,b
M2 Loss of CH2 [M-H]− C17H14O7 329.0668 0.5 10.27 314.0423, 313.0344, 299.0189, 285.0393, 133.0287 2.26434 91.8 - - + a,b + a,b + I,II + a,b
M3 Loss of CH2 [M-H]− C17H14O7 329.0662 −1.4 10.79 314.0436,313.0357, 299.0204, 285.0396, 207.7166 2.51422 96.3 - - + a,b + a,b + I,II + a,b
M4a Loss of CH2 and CH2 [M-H]− C16H12O7 315.0500 −3.3 7.26 300.0279, 297.1740, 269.1760, 251.1269, 133.0270 1.82034 85.4 - - + a,b + a,b +I -
M4b 2.07034
M5 Loss of CH2 and CH2 [M-H]− C16H12O7 315.0504 −2.0 8.50 300.0275, 297.0411, 269.1755, 251.1658, 147.0821 2.18513 93.3 - - + a,b + a,b + I -
M6a Loss of CH2O [M-H]− C17H14O6 313.0713 −1.4 13.86 298.0483, 283.0250, 221.0632, 147.0078, 117.0364 2.86048 90.9 - - - + a,b - + a,b
M6b 3.08571
M6c 3.33571
M7 Loss of CH2O and CH2 [M-H]− C16H12O6 299.0562 0.3 10.10 284.0326, 281.1787, 251.1281, 146.9687 2.74964 83.8 - - + a - + I + b
M8 Loss of CH2O and CH2O [M-H]− C16H12O5 283.0614 0.8 13.60 268.0379, 240.0428, 267.0306, 161.0025, 146.9655 3.30833 93.5 - - + a,b + b + I + b
M9 Loss of O [M-H]− C18H16O6 327.0882 2.4 4.98 308.9931, 299.1274, 281.2489, 205.0025, 146.9380 2.45814 75.3 - - - - - + b
M10 Loss of O [M-H]− C18H16O6 327.0872 −0.8 7.47 309.0800, 299.0957, 281.2493, 221.0452, 130.9716 3.44497 83.5 - - - - - + b
M11 Loss of O and O [M-H]− C18H16O5 311.0930 1.5 9.55 250.9816, 204.9868, 174.9556, 130.9658 3.19475 75.7 - - - - - + b
M12a Loss of O and CH2O [M-H]− C17H14O5 297.0768 −0.2 7.33 267.1016, 253.0865, 175.0394, 147.0452, 145.0305 2.78433 82.1 - - - - - + b
M12b
M13 Loss of CO [M-H]− C17H16O6 315.0862 −3.8 12.74 300.0633, 285.0401, 270.0144, 193.0503, 147.0445 2.84747 87.9 - - - + a,b - + a,b
M14 Oxidation [M-H]− C18H16O8 359.0772 −0.2 10.01 344.0542, 329.0304, 314.0064, 220.9817, 163.0384 1.79518 82.9 - - + a,b + a,b + I + a,b
M15 Oxidation [M-H]− C18H16O8 359.0768 −1.3 10.50 344.0529, 329.0306, 314.0061, 221.0098, 163.0368 1.84518 82.8 - - + a,b + a,b + I + a,b
M16 Oxidation [M-H]− C18H16O8 359.0767 −1.6 11.47 344.0536, 329.0296, 314.0066, 221.0762, 163.0019 1.86518 81.9 - - + a,b + a,b + I + a,b
M17 Oxidation [M-H]− C18H16O8 359.0767 −1.4 12.23 344.0542, 329.0315, 314.0085, 237.0375, 147.0130 1.87123 85.5 - - + a,b + a,b + I + a,b
M18 Di-Oxidation [M-H]− C18H16O9 375.0709 −3.3 9.90 329.0669, 314.0434, 299.0191, 221.1216, 178.9947 0.9644 91.2 - - - + a,b - + a
M19 Tri-Oxidation [M-H]− C18H16O10 391.0673 0.5 12.26 345.0869, 330.0636, 315.0393, 221.0399, 195.0289 0.25226 77.1 - - + b - - + a,b
M20a Demethylation and Oxidation [M-H]− C17H14O8 345.0605 −3.0 9.43 330.0379, 301.1825, 221.1270, 149.0245, 125.0237 1.29734 84.9 - - + a,b + b + I + b
M20b
M21 Demethylation and Oxidation [M-H]− C17H14O8 345.0606 −2.8 10.29 330.0384, 301.0719, 221.0028, 149.0234, 125.0311 1.59734 87.1 - - + a,b + b + I + b
M22 Methylation [M-H]− C19H18O7 357.0972 −2.1 10.02 342.0740, 327.0503, 312.0266, 235.0434, 147.0433 2.06632 80.6 - - + a,b + a,b - + a,b
M23 Methylation [M-H]− C19H18O7 357.0969 −3.1 12.86 342.0737, 327.0508, 312.0266, 221.0766, 161.0269 3.18323 78.6 - - + a,b + a,b - + a,b
M24 Loss of O+Methylation [M-H]− C19H18O6 341.1025 −1.5 7.15 326.1073, 311.0918, 235.0607, 130.9906, 107.0440 2.80306 82.8 - - - - - + b
M25 Loss of O+Methylation [M-H]− C19H18O6 341.1027 −1.2 8.79 326.0798, 311.0451, 204.9196, 161.0595, 137.0553 2.9313 82.1 - - - - - + b
M26 Loss of CH2O and CH2O+Demethylation [M-H]− C15H10O5 269.0459 1.3 9.89 253.0124, 241.0500, 225.0555, 133.0298, 117.0349 2.88784 95.6 + a,b - + a,b - - + a,b
M27 Loss of CH2O and CH2+Demethylation [M-H]− C15H10O6 285.0402 −0.9 8.45 267.0130, 241.0462, 221.0063, 177.0189, 133.0307 2.31115 90.2 - - - - - + b
M28 Glucuronidation [M-H]− C24H24O13 519.1140 −0.8 7.10 397.0442, 343.0822, 328.0587, 313.0346, 146.9662 −0.495 81.6 + a + b + a,b - + II -
M29 Glucuronidation [M-H]− C24H24O13 519.1151 1.3 8.14 343.0824, 328.0588, 323.0173, 313.0354, 221.0262 0.62193 83.1 + a + b + a,b - + II -
M30 Demethylation and Glucuronide Conjugation [M-H]− C23H22O13 505.0979 −1.8 7.88 329.0669, 309.0687, 299.0165, 285.0735 0.14693 81.3 - - + a,b - - -
M31 Sulfate Conjugation [M-H]− C18H16O10S 423.0391 0.1 8.93 343.0830, 328.0593, 313.0355, 285.0413, 147.0037 0.27032 86.1 - + a,b + a,b - - + a,b
M32 Sulfate Conjugation [M-H]− C18H16O10S 423.0387 −0.9 9.20 343.0836, 328.0606, 313.0371, 285.0457, 227.0084 1.38723 89.6 - + a,b + a,b - - + a,b
M33 Loss of CH2+Sulfate Conjugation [M-H]− C17H14O10S 409.0233 −0.4 9.01 329.0670, 314.0432, 299.0198, 212.0456, 132.0208 0.81223 91.5 + a - + a,b - - -
M34 Loss of O+Sulfate Conjugation [M-H]− C18H16O9S 407.0434 −2.1 12.65 327.0826, 301.0034, 220.9818, 131.0573 1.00706 63.3 - - - - - + b
M35 N-Acetylation [M-H]− C20H18O8 385.0917 −3.1 13.36 370.0729, 355.0427, 343.0846, 263.0551, 147.0513 1.49632 74.4 - - - - - + b
M36 N-Acetylation [M-H]− C20H18O8 385.0925 −0.9 13.90 370.0735, 355.0492, 343.0874, 221.0781, 189.0551 2.61323 77.9 - - - - - + b
M37 Loss of O+N-Acetylation [M-H]− C20H18O7 369.0987 2.1 13.02 327.2227, 279.0680, 263.1681, 237.1098, 130.9934 2.23306 75.3 + a - + a,b + a,b + I + a,b
M38 Loss of O+N-Acetylation [M-H]− C20H18O7 369.0975 −1.3 13.90 354.0755, 339.0542, 311.0594, 174.9586, 164.9289 2.3613 76.7 + a - + a,b + a,b + I + a,b
M39 Loss of CH2+N-Acetylation [M-H]− C19H16O8 371.0761 −3.2 11.45 329.0680, 314.0439, 299.0196, 220.9869, 175.0389 2.13823 76.8 - - - + a,b - + b
M40 Loss of CH2O+N-Acetylation [M-H]− C19H16O7 355.0813 −2.9 11.86 340.0587, 325.0335, 313.1107, 263.0361, 117.0329 1.64857 78.2 - - + a,b + a,b + I + a,b
M41 Loss of CH2O+N-Acetylation [M-H]− C19H16O7 355.0814 −2.6 13.15 340.0589, 325.0356, 313.0337, 221.0027, 159.1093 2.87497 78.1 - - + a,b + a,b + I + a,b
M42 Loss of CH2O+Di-Acetylation of Amines [M-H]− C21H18O8 397.0918 −2.6 15.21 382.0691, 367.0426, 313.2553, 263.0559, 159.0462 1.66306 74.8 - - - + b - + b
M43a Loss of CH2 and CH2+Di-Acetylation of Amines [M-H]− C20H16O9 399.0704 −4.3 14.14 384.0497, 357.0641, 315.0523, 175.0034, 147.0316 1.56823 71.8 - - - + b - -
M43b
M43c
M44a Loss of CH2O and CH2O+Di-Acetylation of Amines [M-H]− C20H16O7 367.0806 −4.8 15.24 283.0237, 233.1253, 202.9904, 189.0633, 159.0348 2.05475 71.9 - - - + a,b - -
M44b 2.11133
M44c 2.40475
M45 Loss of O+Hydrogenation [M-H]− C18H18O6 329.1028 −0.8 4.57 314.0861, 299.1136, 283.2624, 223.0900, 130.9874 1.71027 75.9 - - - - - + a,b
M46 Loss of O+Hydrogenation [M-H]− C18H18O6 329.1029 −0.5 5.14 314.0905, 299.1189, 283.1288, 207.0777, 147.0535 1.7953 76.7 - - - - - + a,b
M47 Loss of O+Hydrogenation [M-H]− C18H18O6 329.1029 −0.3 5.43 314.0384, 299.0986, 283.2612, 207.0618, 149.0538 2.28982 78.7 - - - - - + a,b
M48 Loss of O+Hydrogenation [M-H]− C18H18O6 329.1029 −0.6 9.69 314.0226, 299.0298, 283.0982, 223.0742, 133.0731 2.89116 75.8 - - - - - + a,b
M49 Loss of O and O+Hydrogenation [M-H]− C18H18O5 313.1080 −0.3 7.61 298.0759, 269.1191, 239.1066, 206.9936, 130.9677 2.5321 88.5 - - - - - + a,b
M50 Loss of O and O+Hydrogenation [M-H]− C18H18O5 313.1086 1.6 7.88 298.0767, 269.1189, 239.1061, 207.0818, 133.0654 3.02662 90.7 - - - - - + a,b
M51 Demethylation and Hydrogenation [M-H]− C17H16O7 331.0824 0.3 10.05 316.0595, 313.1396, 301.0343, 223.1657, 135.0450 1.70816 90.5 - - + a,b - - + a
M52 Di-Hydrogenation [M-H]− C18H20O7 347.1140 1.0 12.78 332.0913, 317.0676, 225.0074, 149.0591, 123.0079 0.81747 60.2 - - + a,b - - + b
M53 Loss of O+Di-Hydrogenation [M-H]− C18H20O6 331.1186 −0.2 3.60 301.1097, 299.1257, 285.1728, 225.0501, 133.0325 1.55427 53.1 - - + b - - + b
M54 Loss of O+Di-Hydrogenation [M-H]− C18H20O6 331.1185 −0.7 4.07 301.1088, 299.1304, 285.0945, 209.0813, 149.0680 1.6393 52.8 - - + b - - + b
M55 Loss of O and O+Di-Hydrogenation [M-H]− C18H20O5 315.1214 −1.6 6.36 285.1155, 271.1557, 269.1318, 241.1035, 133.0693 2.3761 83.6 - - + a - - + a,b
M56 Loss of CH2+Di-Hydrogenation [M-H]− C17H18O7 333.0972 −2.3 10.18 318.0813, 317.1125, 303.0579, 211.0624, 149.0642 0.32475 94.4 - - + a,b - - -
M57 Loss of CH2+Di-Hydrogenation [M-H]− C17H18O7 333.0982 0.6 10.24 315.0034, 225.2199, 179.1064, 135.1164, 109.0679 0.37127 63.2 - - + a,b - - -
M58 Loss of CH2+Di-Hydrogenation [M-H]− C17H18O7 333.0979 −0.3 10.80 315.0884, 300.0638, 285.0374, 211.0614, 149.0693 0.64475 90.6 - - + a,b - - -
M59a Loss of CH2 and CH2+Di-Hydrogenation [M-H]− C16H16O7 319.0815 −2.6 8.47 301.0701, 211.0353, 197.0452, 149.0269, 135.0443 0.19855 89.0 - - - + a,b - -
M59b −0.1214
M59c 0.22768
M60 Loss of CH2O and CH2O+Di-Hydrogenation [M-H]− C16H16O5 287.0923 −0.8 9.97 272.0689, 241.0875, 195.0653, 119.0500, 93.0325 1.35527 80.7 - - - - - + b
M61 Loss of CH2O and CH2O+Di-Hydrogenation [M-H]− C16H16O5 287.0927 0.5 11.07 272.0695, 241.2138, 165.0166, 149.0683, 123.0117 1.4214 85.8 - - - - - + b
M62a Loss of O and CH2O+Di-Hydrogenation [M-H]− C17H18O5 301.1078 −1.2 7.37 271.1359, 255.0541, 241.0814, 179.0711, 149.0605 1.9972 87.9 + a - - + a,b - -
M62b
M63 Loss of CH2O and CH2O+Loss of Hydroxymethylene [M-H]− C15H10O4 253.0512 2.1 7.81 225.0558, 209.0606, 161.0249, 117.0351, 101.0246 3.4753 70.9 + b - + a,b - - + b
M64 Ketone Formation [M-H]− C18H14O8 357.0607 −2.5 10.79 342.0374, 327.0132, 313.0304, 221.0224, 161.0174 2.17223 79.1 - - - + b + I -
M65 Ketone Formation [M-H]− C18H14O8 357.0609 −1.8 10.81 342.0379, 327.0146, 313.0349, 235.0241, 147.0012 2.27223 76.1 - - - + b + I -
M66 Ketone Formation [M-H]− C18H14O8 357.0610 −1.6 12.99 342.0385, 327.0198, 313.0421, 235.0267, 147.0503 2.52223 77.4 - - - + b + I -
M67 Oxidation and Internal Hydrolysis [M-H]− C18H18O9 377.0875 −0.8 12.29 362.0508, 349.0873, 239.0435, 181.0136, 139.0054 0.21452 83.4 - - - + a,b - + a,b
M68a Loss of CH2+Glycine Conjugation [M-H]− C19H17NO8 386.0865 −4.2 10.00 329.0662, 314.0421, 299.0189, 264.1192, 147.0973 2.15391 80.8 - - - + b - -
M68b 2.40391
M69a Loss of O and CH2O+Glycine Conjugation [M-H]− C19H17NO6 354.0992 2.5 6.09 324.2008, 250.9077, 221.0751, 204.0387, 174.9553 2.66894 73.9 - + a - - - -
M69b
M70 Loss of CH2O+Glutamine Conjugation [M-H]− C22H22N2O8 441.1302 −0.2 5.07 312.8496, 245.1021, 221.5883, 117.2304 0.99254 50.9 - - - - - + b
M71 Loss of CH2 and CH2+Glucose Conjugation [M-H]− C22H22O12 477.1036 −0.6 5.49 355.0661, 315.6277, 192.9548, 146.9654, 123.0795 −0.3982 52.9 - - - - - + b

+, Detected; -, Undetected. RLMs, rat liver microsomes; RIF, rat intestinal flora. (a) Metabolites obtained by methanol precipitation protein; (b) metabolites obtained by ethyl acetate extraction; a+b metabolites obtained by methanol precipitation protein and ethyl acetate extraction. (I) Phase I metabolites obtained from liver microsomes; (II) phase II metabolites obtained from liver microsomes.