Table A1.
LC/MS parameters of flavonolignans and their metabolites produced by human fecal microbiota.
| Compound | Elemental Composition | m/z | tR (min) | Δppm | MSE |
|---|---|---|---|---|---|
| Taxifolin | |||||
| Taxifolin | C15H12O7 | 303.0490 | 2.5 | −4.9 | 175.0391; 125.0224 |
| Taxifolin isomer | C15H12O7 | 303.0486 | 2.8 | −6.3 | 125.0221 |
| C15H10O4 | C15H10O4 | 253.0488 | 10.3 | −5.1 | xxx |
| Sulfate conjugation | C15H12O10S | 383.0034 | 1.5 | −7.3 | 285.0424 |
| Loss of O | C15H12O6 | 287.0540 | 3.6 | −5.6 | 177.0523; 125.0225 |
| Loss of O | C15H12O6 | 287.0538 | 5.2 | −6.3 | xxx |
| Loss of O | C15H12O6 | 287.0541 | 1.6 | −5.2 | xxx |
| Methylation | C16H14O7 | 317.0650 | 4.2 | −3.5 | 125.0263 |
| 2x Loss of O | C15H12O5 | 271.0609 | 6.8 | 1.1 | xxx |
| Silybin | |||||
| Silybin A | C25H22O10 | 481.1118 | 7.7 | −3.5 | 301.0304; 125.0217 |
| Silybin B | C25H22O10 | 481.1123 | 7.8 | −2.5 | 301.0349; 125.0210 |
| Isosilybin | C25H22O10 | 481.1165 | 8.2 | 6.2 | xxx |
| Demethylation | C24H20O10 | 467.0946 | 6.1 | −6.9 | 301.0317; 125.0212 |
| Demethylation | C24H20O10 | 467.0964 | 6.2 | −3.0 | 301.0322; 125.0217 |
| Isosilybin | |||||
| Isosilybin | C25H22O10 | 481.1133 | 8.3 | −0.4 | 453.1169; 125.0224 |
| Demethylation | C24H20O10 | 467.0954 | 6.4 | −5.1 | 125.0221 |
| Demethylation | C24H20O10 | 467.0969 | 6.5 | −1.9 | 285.0389; 125.0227 |
| Decarbonylation | C24H21O9 | 453.1164 | 6.3 | −4.9 | 181.0141; 125.0203 |
| Silychristin | |||||
| Silychristin A | C25H22O10 | 481.1129 | 5.1 | −1.2 | 325.0701; 125.0232 |
| Silychristin B | C25H22O10 | 481.1124 | 5.3 | −2.3 | 325.0687 |
| Reduction | C25H24O10 | 483.1268 | 5.3 | −4.8 | 357.0912; 125.0242 |
| Reduction | C25H24O10 | 483.1346 | 4.8 | 11.4 | xxx |
| Desaturation + demethylation + sulfate conjugation | C24H18O13S | 545.0369 | 4.8 | −3.9 | xxx |
| Desaturation + demethylation | C24H18O10 | 465.0819 | 6.5 | −0.6 | xxx |
| + C3H6O | C28H28O11 | 539.1550 | 5.9 | −0.6 | 183.0648; 237.0384 |
| + C3H6O + desaturation | C28H26O11 | 537.1390 | 7.0 | −1.3 | 235.0247 |
| + C3H6O isomer + desaturation | C28H26O11 | 537.1394 | 7.3 | −0.6 | 183.0655; 235.0224 |
| + C5H8O2 | C30H30O12 | 581.1659 | 6.2 | −0.2 | 553.1713; 279.0490 |
| C4H8O6 | C4H8O6 | 151.0239 | 0.7 | −2.6 | xxx |
| C4H8O7 | C4H8O7 | 167.0200 | 0.6 | 4.8 | xxx |
| Silydianin | |||||
| Silydianin | C25H22O10 | 481.1135 | 6.6 | 0.0 | 178.9972; 151.0023 |
| Reduction | C25H24O10 | 483.1280 | 4.7 | −2.3 | 125.0236 |
| Cysteine conjugation | C28H27NO11S | 584.1212 | 6.1 | −2.6 | 326.0632; 178.9949 |
| Cysteine conjugation | C28H27NO11S | 584.1229 | 7.7 | 0.3 | 125.0215; 326.0641 |
| Cysteine conjugation | C28H27NO11S | 584.1216 | 6.3 | −1.9 | 326.0647; 125.0211 |
| Cysteine conjugation | C28H27NO11S | 584.1207 | 6.0 | −3.4 | 326.0670 |
| Decarbonylation | C24H22O9 | 453.1169 | 6.3 | −3.8 | 125.0215; 182.0191 |
| Desaturation | C25H20O10 | 479.0982 | 7.2 | 0.8 | 299.0183 |
| +C3H6O | C28H28O11 | 539.1563 | 6.9 | −0.6 | 209.0441; 237.0386 |
| +C3H6O + desaturation | C28H26O11 | 537.1393 | 7.7 | −0.7 | 235.0241 |
| +C3H6O isomer + desaturation | C28H26O11 | 537.1396 | 8.2 | −0.2 | 235.0220; 207.0274 |
| + C5H8O2 | C30H30O12 | 581.1656 | 7.2 | −0.5 | xxx |
| C4H8O6 | C4H8O6 | 151.0252 | 0.8 | 6.0 | 135.0308 |
| C4H8O7 | C4H8O7 | 167.0205 | 0.7 | 7.8 | xxx |
| 2,3-Dehydrosilybin | |||||
| 2,3-Dehydrosilybin | C25H20O10 | 479.0985 | 10.2 | 1.5 | 299.0185; 271.0237 |
| 2,3-Dehydrosilybin isomer | C25H20O10 | 479.0971 | 10.0 | −1.5 | 299.0186; 271.0241 |
| Demethylation | C24H18O10 | 465.0825 | 8.7 | 0.6 | 299.0188; 271.0238 |
| Silybin A | C25H22O10 | 481.1115 | 8.0 | −4.2 | 301.0331; 125.0248 |
| Silybin B | C25H22O10 | 481.1134 | 8.1 | −0.2 | 301.0341 |
| Reduction + demethylation | C24H20O10 | 467.0970 | 6.1 | −1.7 | 125.0215; 301.0320 |
| Reduction + demethylation | C24H20O11 | 467.0963 | 6.2 | −3.2 | 125.0213; 301.0315 |
| 2,3-Dehydrosilychristin | |||||
| 2,3-Dehydrosilychristin | C25H20O10 | 479.0964 | 7.4 | −2.9 | 449.0852; 151.0018 |
| Dehydrosilychristin isomer | C25H20O10 | 479.0958 | 7.7 | −4.2 | 449.0944; 461.0851 |
| 2,3-Dehydrosilybin | C25H20O10 | 479.0941 | 10.0 | −7.7 | 299.0178 |
| Silychristin A | C25H22O10 | 481.1119 | 5.1 | −3.3 | 125.0229; 325.0711 |
| Silychristin B | C25H22O10 | 481.1115 | 5.3 | −4.2 | 125.0253 |
| Demethylation | C24H18O10 | 465.0816 | 5.9 | −1.3 | xxx |
| Reduction + demethylation | C24H20O10 | 467.0950 | 6.4 | −6.0 | xxx |
| Reduction + demethylation | C24H20O10 | 467.0934 | 6.1 | −9.4 | xxx |
| Reduction + demethylation | C24H20O10 | 467.0948 | 6.2 | −6.4 | xxx |
| 2x reduction | C25H24O10 | 483.1307 | 5.3 | 3.3 | 125.0245 |
| 2,3-Dehydrosilydianin | |||||
| 2,3-Dehydrosilydianin | C25H20O10 | 479.0955 | 7.0 | −4.8 | 299.0168; 127.0477 |
| Silydianin | C25H22O10 | 481.1135 | 6.3 | −0.2 | 151.0013; 178.9931 |
| Cysteine conjugation | C28H25NO11S | 582.1053 | 8.2 | −3 | 324.0479 |
| Cysteine conjugation | C28H25NO11S | 582.1066 | 9.1 | −0.7 | 324.0489 |
| Decarbonylation | C24H20O9 | 451.1004 | 7.1 | −5.5 | 315.1245; 300.1013 |
| Decarbonylation | C24H20O9 | 451.1029 | 9.2 | 0.0 | 301.0341 |
| Demethylation | C24H18O10 | 465.0805 | 7.1 | −3.7 | xxx |
| Reduction + demethylation | C24H20O10 | 467.0966 | 6.2 | −2.6 | 125.0244; 151.0105 |
| Reduction + cysteine conjg. | C28H27NO11S | 584.1221 | 7.7 | −1 | 326.0655; 125.0227 |
MSE refers to mass spectrometry experiment with higher collision energy without isolation on the quadrupole (see Section 3.6). xxx: MSE data were not measurable.