Table 2.
UPLC-HRMS data for POD metabolites detected in mouse bile
| No. | Metabolic pathway | Formula | m/z | Error (ppm) |
Rt (min) |
Fragments | bile | feces |
|---|---|---|---|---|---|---|---|---|
| M1 | Cleavage of methylenedioxy |
C21H22O8 | 401.12 23 |
−3.4 | 6.12 | 339.1248, 324.0984, 293.0478, 277.0391, 265.0268, 249.0378, 237.0583, 210.0623, 172.0535, 145.0987 | √ | |
| M2-2 | Demethylation | C21H20O8 | 399.1090 | 2.5 | 6.93 | 384.0882, 369.0609, 341.0717, 269.0538, 226.0280, 175.0440 | √ | √ |
| M2-3 | Demethylation | C21H20O8 | 399.1099 | 4.7 | 7.51 | 384.1006, 369.0568, 355.0383, 341.0587, 325.0635, 253.0500, 214.0280, 187.0390, 158.0360 | √ | √ |
| M2-4 | Demethylation | C21H20O8 | 399.1078 | 0.5 | 7.74 | 384.0793, 369.0598, 355.0764, 341.0656, 325.0624, 297.0826, 282.0378, 269.0437, 254.0561,226.0895, 187.0443 | √ | √ |
| M3-1 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1441 | 6.9 | 5.88 | 399.1091, 384.0837, 369.0566, 355.1077, 349.0902, 325.0632, 270.0258, 201.0399, 186.0386 | √ | |
| M3-2 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1417 | 2.8 | 6.63 | 399.1094, 384.0913, 369.0634, 341.0645, 270.0529, 254.0692, 239.0599, 227.0220, 187.0471, 113.0248 | √ | |
| M3-3 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1431 | 5.2 | 6.41 | 399.1091, 384.0836, 355.0571, 341.0668, 339.0911, 325.0579, 311.0639, 297.0636, 271.7139 | √ | |
| M3-4 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1426 | 4.3 | 4.96 | 531.1584, 399.1072, 369.0678, 355.1063, 340.0962, 325.0691, 299.0407, 269.0428, 221.855, 113.0601 | √ | |
| M3-5 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1423 | 3.8 | 5.55 | 399.1129, 384.0775, 369.0723, 355.0593, 340.1182, 325.0668, 298.3300, 269.0538, 201.0249, 185.1393, 175.0196 | √ | |
| M3-6 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1446 | 7.8 | 5.71 | 399.1090, 384.0869, 369.0633, 355.0855, 341.0823, 325.0712, 269.0506, 255.0427, 242.0083, 174.9917 | √ | |
| M3-7 | Demethylation+glucuronide conjugation | C27H28O14 | 575.1435 | 5.9 | 6.76 | 399.1115, 384.0853, 369.0585, 355.0851, 341.0630, 325.0765, 319.1001, 187.0376 | √ | |
| M4-1 | Cleavage of methylenedioxy+glucuronide conjugation | C27H30O14 | 577.1569 | 2 | 4.63 | 401.1230, 383.1215, 339.1220, 324.1000, 309.0774, 293.0490, 281.0708, 266.0593, 215.0320, 172.0520, 129.2002, 113.0230 | √ | |
| M4-2 | Cleavage of methylenedioxy+glucuronide conjugation | C27H30O14 | 577.157 | 2.2 | 5.58 | 559.1455, 401.1230, 383.1007, 339.1230, 324.1000, 294.0520, 281.1129, 266.1015, 215.0153, 172.0510, 113.0530 | √ | |
| M5-1 | Cleavage of methylenedioxy+GSH | C31H37N3O14S | 706.1939 | 2.9 | 3.25 | 433.0876, 418.0645, 371.0806, 272.0831, 254.1130, 210.0193, 190.0050 | √ | |
| M5-2 | Cleavage of methylenedioxy+GSH | C31H37N3O14S | 706.1981 | 8.9 | 3.65 | 433.0949, 415.0855, 387.0832, 371.0866, 337.2072, 306.0751, 283.2010, 247.0037, 242.0829, 221.1189 | √ | |
| M6-1 | 2 × Demethylation | C20H18O8 | 385.0952 | 7.3 | 6.2 | 370.0685, 355.0446, 327.0551, 255.0263, 173.0360 | √ | |
| M6-2 | 2 × Demethylation | C20H18O8 | 385.0897 | −6.8 | 6.55 | 370.0659, 311.0406, 277.0762, 254.0294, 187.0810 | √ | |
| M7 | Demethylation+sulfate conjugation | C20H18O8 | 479.0662 | 2.8 | 7.41 | 399.1030, 384.0828, 369.0601, 340.0986 , 325.0631, 252.2453, 187.7986 | √ | |
| M8-1 | 2 × Demethylation+glucuronide conjugation | C26H26O14 | 561.127 | 4.5 | 4.6 | √ | ||
| M8-2 | 2 × Demethylation +glucuronide conjugation | C26H26O14 | 561.1243 | −0.3 | 5.31 | 385.0927, 370.0681, 355.0548, 337.0338, 309.0448, 269.0330 | √ | |
| M8-3 | 2 × Demethylation+glucuronide conjugation | C26H26O14 | 561.1266 | 3.8 | 5.48 | 495.1594, 385.0953, 370.0692, 311.0600 | √ | |
| M8-4 | 2 × Demethylation+glucuronide conjugation | C26H26O14 | 561.1276 | 5.6 | 5.59 | 448.1119, 385.0969, 370.0578, 355.0551, 326.0879, 311.0695, 270..2240 | √ | |
| M9-1 | Glucuronide conjugation | C28H30O14 | 589.1582 | 4.1 | 6.14 | 545.1631, 413.1216, 398.1004, 369.1363, 339.1353, 309.1948, 299.1623, 269.3391, 202.0482, 188.1066, 175.0220, 113.0258 | √ | |
| M9-2 | Glucuronide conjugation | C28H30O14 | 589.1586 | 4.8 | 6.32 | 413.1219, 383.0779, 368.0705, 355.1013, 340.0582, 325.0591, 284.1261, 266.8437, 250.1859, 227.3869, 175.027, 113.0285 | √ | |
| M9-3 | Glucuronide conjugation | C28H30O14 | 589.1575 | 3 | 6.7 | 413.1189, 398.0909, 383.0685, 369.1264, 354.1086, 339.0630, 324.0875, 299.0606, 255.0750, 203.0353, 175.0061, 145.1546, 113.0138 | √ | |
| M9-4 | Glucuronide conjugation | C28H30O14 | 589.1573 | 2.6 | 7.01 | √ | ||
| M9-5 | Glucuronide conjugation | C28H30O14 | 589.16 | 7.2 | 7.09 | 413.1212, 398.0994, 383.0744, 369.0588, 355.0831, 340.0855, 325.0072, 286.3051, 269.0588, 203.0353, 175.0380 | √ | |
| M9-6 | Glucuronide conjugation | C28H30O14 | 589.1583 | 4.3 | 7.21 | 413.1237, 398.1023, 383.0129, 339.0854, 309.0428, 186.0380, 175.0291 | √ | |
| M10-1 | Cleavage of methylenedioxy+glucuronide conjugation+methylatio n | C28H32O14 | 591.1715 | 0.2 | 4.93 | 514.2815, 415.1417, 353.1461, 338.1165, 323.0939, 186.0668, 175.0242 | √ | |
| M10-2 | Cleavage of methylenedioxy+glucuronide conjugation+methylatio n | C28H32O14 | 591.1737 | 3.9 | 6.29 | 514.2841, 415.1274, 414.1250, 413.1176, 399.1145, 383.0753, 296.6187, 157.0182, 99.0161 | √ | |
| M11-1 | Cleavage of methylenedioxy+GSH+ glucuronide conjugation | C37H45N3O20S | 882.2272 | 3.7 | 4.14 | 706.1192, 575.1458, 399.1082, 355.1165, 306.0752, 272.0855, 254.0826, 210.0868, 128.3057 | √ | |
| M11-2 | Cleavage of methylenedioxy+GSH+ glucuronide conjugation | C37H45N3O20S | 882.228 | 4.6 | 3.73 | 706.2347, 575.1404, 399.1087, 355.1194, 306.0722, 272.0764, 210.0845, 177.0395 | √ | |
| M11-3 | Cleavage of methylenedioxy+GSH+ glucuronide conjugation | C37H45N3O20S | 882.2292 | 6 | 3.86 | 706.1868, 272.0910, 254.0812 | √ | |
| M11-4 | Cleavage of methylenedioxy+GSH+ glucuronide conjugation | C37H45N3O20S | 882.2292 | 6 | 3.56 | 575.1255, 306.0772, 272.0910, 254.0812 | √ | |
| M12-1 | Methylation + Cleavage of methylenedioxy +GSH+ glucuronide conjugation | C38H47N3O20S | 896.2437 | 4.6 | 3.74 | 589.1584, 413.1256, 369.1298, 306.0741, 272.078 | √ | |
| M12-2 | Methylation + Cleavage of methylenedioxy +GSH+ glucuronide conjugation | C38H47N3O20S | 896.2438 | 4.7 | 4.84 | 750.9995, 720.2079, 589.153, 369.1283, 306.0712, 272.09, 254.0798, 210.0905, 143.0298 | √ | |
| M12-3 | Methylation + Cleavage of methylenedioxy +GSH+ glucuronide conjugation | C38H47N3O20S | 896.2453 | 6.4 | 4.36 | 720.1957, 589.1576, 369.1283, 306.0788, 272.1041, 254.0677, 210.0823, 179.0457, 159.9807, 143.0401, 128.0094 | √ | |
| M12-4 | Methylation + Cleavage of methylenedioxy +GSH+ glucuronide conjugation | C38H47N3O20S | 896.2457 | 6.8 | 4.07 | 599.1248, 590.1661, 514.1617, 417.2951, 373.2826, 369.1425, 306.0735, 272.0733, 254.0791, 160.0085, 143.0451 | √ |