Summary of metabolites of eriocitrin in rat plasma, bile, urine and faeces samplesa.
| Metabolites ID | Composition | Formula | m/z | Error (ppm) | R.T. (min) | Score (%) | MS/MS fragments | clog P | Plasma | Bile | Urine | Faeces |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| M1 | Loss of C12H20O9 [M − H]− | C15H12O6 | 287.0560 | −0.3 | 15.30 | 75.0 | 269.0458, 241.0489, 151.0032, 135.0447, 125.0242 | 1.84785 | − | − | +b | +a,b |
| M2 | Loss of C12H20O10 [M − H]− | C15H12O5 | 271.0615 | 1.3 | 16.99 | 75.0 | 253.0507, 243.0682, 227.0715, 135.0468 | 2.39694 | − | − | +a,b | +a,b |
| M3 | Loss of O and C12H20O10 [M − H]− | C15H12O4 | 255.0665 | 1.0 | 15.41 | 79.9 | 237.2257, 135.0064, 119.0480, 109.0795 | 2.2109 | − | − | +a | − |
| M4 | Loss of O and C12H20O10 [M − H]− | C15H12O4 | 255.0656 | −2.8 | 18.43 | 75.7 | 239.0307, 135.0082, 119.0495, 93.0350 | 2.99394 | − | − | +a | − |
| M5 | Loss of C12H20O9 + loss of CO [M − H]− | C14H12O5 | 259.0610 | −0.6 | 11.92 | 75.0 | 241.0487, 213.0566, 195.1086, 183.0853, 135.0081 | 1.59026 | − | − | +b | − |
| M6 | Loss of C12H20O10 + loss of water [M − H]− | C15H10O4 | 253.0507 | 0.3 | 18.18 | 75.0 | 225.0568, 209.0609, 181.0649, 119.0499 | 3.73694 | +a | +b | +a | +b |
| M7 | Loss of C12H20O10 + hydrogenation [M − H]− | C15H14O5 | 273.0772 | 1.3 | 16.57 | 75.0 | 245.0475, 227.1310, 209.1184, 165.1286, 135.0453 | 0.9752 | − | − | − | +a |
| M8 | Loss of O and C12H20O10 + hydrogenation [M − H]− | C15H14O4 | 257.0817 | −1.0 | 14.82 | 75.0 | 239.1684, 213.0584, 135.0454, 121.0226, 119.0503 | 1.462 | − | − | +a,b | − |
| M9 | Loss of O and C12H20O10 + hydrogenation [M − H]− | C15H14O4 | 257.0829 | 3.7 | 18.59 | 70.7 | 241.0750, 213.0224, 137.0357, 119.0472 | 1.5722 | − | − | +a,b | − |
| M10 | Loss of C12H20O10 + ketone formation [M − H]− | C15H10O6 | 285.0401 | −1.2 | 15.78 | 75.0 | 267.0283, 257.0428, 223.0290, 149.0245, 133.0294 | 1.48794 | − | − | +b | − |
| M11 | Loss of C6H10O4 + N-acetylation [M − H]− | C23H24O12 | 491.1167 | −5.8 | 15.07 | 65.5 | 473.0057, 367.1394, 287.1502, 125.0238 | 0.53447 | − | +a | +b | +a,b |
| M12 | Loss of C6H10O5 + N-acetylation [M − H]− | C23H24O11 | 475.1245 | −0.3 | 15.35 | 62.5 | 429.1966, 329.0920, 270.9431, 135.0438, 119.0481 | 0.0924672 | − | +a | − | − |
| M13 | Loss of O and C12H20O10 + di-acetylation of amines [M − H]− | C19H16O6 | 339.0869 | −0.7 | 11.63 | 75.3 | 310.9990, 254.9868, 218.9874, 119.0523 | 1.9929 | − | − | − | +b |
| M14 | Loss of O and C12H20O10 + di-acetylation of amines [M − H]− | C19H16O6 | 339.0871 | −1.1 | 11.85 | 75.5 | 311.0684, 254.9799, 177.2543, 161.0261 | 2.28159 | − | − | − | +b |
| M15 | Loss of C12H20O9 + oxidation [M − H]− | C15H12O7 | 303.0508 | −0.8 | 15.73 | 75.0 | 285.0379, 257.1777, 166.9987, 151.0021, 135.0440 | 1.13085 | − | − | +a | − |
| M16 | Loss of C6H10O4 + di-oxidation [M − H]− | C21H22O13 | 481.1023 | 7.3 | 15.44 | 49.3 | 463.2680, 435.2738, 345.2393, 319.0931 | −1.41361 | − | +a | − | − |
| M17 | Loss of C12H20O9 + di-oxidation [M − H]− | C15H12O8 | 319.0431 | −8.8 | 15.31 | 45.4 | 303.1599, 300.9846, 291.1541, 182.9905, 167.0013, 151.0379, 135.0470 | 0.533851 | − | − | − | +a |
| M18 | Methylation [M − H]− | C28H34O15 | 609.1825 | 0.0 | 13.20 | 75.0 | 301.0714, 286.0456, 254.5695, 165.0182, 151.0027 | −0.914082 | − | +a | − | − |
| M19 | Methylation [M − H]− | C28H34O15 | 609.1816 | −1.4 | 13.51 | 75.0 | 301.0708, 286.0455, 254.0735, 151.0023 | −0.290878 | − | +a | − | − |
| M20 | Loss of C6H10O5 + methylation [M − H]− | C22H24O10 | 447.1292 | −1.0 | 23.83 | 75.0 | 417.1150, 287.0628, 259.1729, 149.0006, 135.0779 | 0.662468 | − | +a,b | + a,b | − |
| M21 | Loss of C12H20O9 + methylation [M − H]− | C16H14O6 | 301.0718 | 0.2 | 16.81 | 75.0 | 287.0544, 285.0411, 165.0185, 135.0448 | 1.91062 | +a,b | +a | +a,b | +a,b |
| M22 | Loss of C12H20O9 + methylation [M − H]− | C16H14O6 | 301.0722 | 1.3 | 16.99 | 75.0 | 287.0544, 285.0411, 165.0185, 135.0448 | 2.37062 | +a,b | +a | +a,b | +a,b |
| M23 | Loss of C12H20O10 + methylation [M − H]− | C16H14O5 | 285.0763 | −2.0 | 14.06 | 75.0 | 266.9834, 239.0535, 149.0046, 135.0018 | 2.23859 | − | +a | − | − |
| M24 | Loss of O and C6H10O5 + methylation [M − H]− | C22H24O9 | 431.1382 | 7.9 | 23.43 | 60.3 | 398.9752, 351.1731, 297.1256, 134.9860, 133.0041, 119.0479 | 2.02247 | − | +b | +a,b | +b |
| M25 | Loss of O and C12H20O10 + methylation [M − H]− | C16H14O4 | 269.0828 | 3.1 | 16.37 | 59.7 | 253.0508, 241.1208, 225.0570, 223.1369, 179.1056, 135.0772, 132.9712 | 2.6571 | − | − | +a | − |
| M26 | Loss of C12H20O9 + oxidation and methylation [M − H]− | C16H14O7 | 317.0670 | 1.1 | 16.81 | 75.0 | 302.0435, 299.0569, 271.0616, 181.0141, 165.0187, 151.0036, 135.0447 | 1.30533 | − | − | +a,b | − |
| M27 | Loss of C12H20O9 + sulfate conjugation [M − H]− | C15H12O9S | 367.0125 | −1.0 | 13.47 | 50.0 | 349.2043, 321.1743, 287.0567, 269.0479, 231.1580, 151.0033, 135.0446 | −0.235379 | +a | − | +a,b | +a |
| M28 | Loss of C12H20O9 + sulfate conjugation [M − H]− | C15H12O9S | 367.0125 | −1.2 | 14.37 | 50.0 | 349.2022, 321.1694, 287.0567, 269.0451, 231.0159, 151.0032, 135.0446 | 0.224621 | +a | − | +a,b | +a |
| M29 | Loss of C12H20O9 + bis-sulfate conjugation [M − H]− | C15H12O12S2 | 446.9695 | −0.5 | 12.68 | 40.8 | 402.8724, 367.0135, 311.2528, 287.0566, 151.0041, 135.0434 | −3.72615 | +a | − | − | − |
| M30 | Loss of C12H20O10 + bis-sulfate conjugation [M − H]− | C15H12O11S2 | 430.9746 | −0.6 | 18.38 | 50.0 | 351.0581, 270.9703, 294.9822, 134.9922, 118.9923 | −0.62306 | − | +b | − | − |
| M31 | Loss of C12H20O10 + glutamine conjugation [M − H]− | C20H20N2O7 | 399.1164 | −8.4 | 13.97 | 59.1 | 353.1116, 335.0996, 291.1097, 263.0735 | 0.68033 | − | +a | − | − |
| M32 | Loss of O and C12H20O10 + glycine conjugation [M − H]− | C17H15NO5 | 312.0889 | 3.8 | 14.54 | 70.6 | 268.1001, 239.1068, 175.9600 | 2.62494 | − | +a | − | − |
a
+ detected; − undetected. aObtained by methanol precipitation protein; bobtained by ethyl acetate extraction; a + bobtained by methanol precipitation protein and ethyl acetate extraction.