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Table 1 Complete list of metabolites

From: Disintegration of wheat aleurone structure has an impact on the bioavailability of phenolic compounds and other phytochemicals as evidenced by altered urinary metabolite profile of diet-induced obese mice

MS m/z(-) Retention time MS/MS m/z ES(-) Tentative structural assignment Molecular formula MM Cluster Ref./Metlin ID
188.0023 0.63 188.0023 [M-H]- 10ev: 188.0025 [M-H]- (100), 79.9574 [SO3]- (74), 108.0456 [M-H-SO3]- (59), 80.9657 (3) 2-Aminophenol sulfate C6H7NO4S 189.0103 Cluster 2 [15]
258.9908 0.65 258.9908 [M-H]- 20ev: 179.0351 [M-SO3]- (100), 135.0451 [M-SO3-COO]- (95), 96.9609 [HSO4]- (5), 135.0941 (2) Caffeic acid sulfate C9H8O7S 260.00 Cluster 3 [16]
261.0061 0.65 261.0061 [M-H]- Unknown M- [261.0061] rt 0.65   262.0141 Cluster 2 N.I.
273.0074 0.65 273.0075 [M-H]- 10ev: 193.0508 [M-H-SO3]- (100), 273.0076 [M-H]- (33), 178.0266 [M-H-SO3-CH3]- (7), 149.0604 [M-H-SO3-COO]- (6), 96.9598 [HSO4]- (5), 193.1079 (5), 134.0365 (5), 229.0171 (3), 79.9571 [SO3]- (1) Ferulic acid sulfate (3- or 4-sulfate) - FA sulfate C10H10O7S 274.0154 Cluster 1 [16]
245.012 0.66 245.0144 [M-H]- 10ev: 245.0119 [M-H]- (100), 165.0547 [M-H-SO3]- (34), 121.065 [M-H-SO3-COO]- (10), 245.0757 (4), 79.957 [SO3]- (2) 3-or 4-Hydroxyphenylpropionic acid sulfate - HPPA-sulfate C9H10O6S 246.02 Cluster 2 MID 4152
275.023 0.67 275.0237 [M-H]- 20ev: 195.0664 [M-H-SO3]- (100), 59.0138 (54), 79.9582 [SO3]- (31), 136.0526 (25), 275.024 [M-H]- (14), 151.0755 [M-H-SO3-COO]- (7) Dihydroferulic acid sulfate C10H12O7S 276.031 Cluster 2 [16]
206.0811 0.73 206.0838 [M-H]- 10ev: 74.0251 [Glycine-H]- (100), 206.0817 [M-H]- (36), 162.0925 [M-H-COO]- (9), 131.0502 [M-glycine]- (3), 126.0264 (3) Unknown glycine conjugate M- [206.0838] rt 0.73 C11H13NO3 207.0891 Cluster 2 N.I.
273.0075 0.79 273.0075 [M-H]-10ev: 193.0508 [M-H-SO3] (100), 273.0075 [M-H]- (42), 96.9608 [HSO4]- (9), 149.0603 [M-H-SO3-COO] (9), 178.0272 (8) Ferulic acid sulfate (3- or 4-sulfate) - FA sulfate C10H10O7S 274.0155 Cluster 1 [16]
204.0668 0.80 204.0667 [M-H]- 10ev: 160.0768 [M-H-COO]- (100), 130.0663 [M-H-C2H4NO2]- (37), 204.0667 [M-H]- (29), 103.0552 [M-C3H3NO3]- (27), 117.0707 (8), 132.0822 (6), 82.0288 (4) Cinnamoylglycine C11H11NO3 205.0748 Cluster 2 MID 34534
245.0118 0.80 245.0144 [M-H]- 10ev: 245.0119 [M-H]- (100), 165.0547 [M-SO3]- (30), 121.065 [M-H-SO3-COO]- (11), 74.0241 (8), 79.957 [SO3]- (2), 201.1035 [M-H-COO]- (2) 3-or 4-Hydroxyphenylpropionic acid sulfate - HPPA-sulfate C9H10O6S 246.0198 Cluster 2 MID 4152
275.0232 0.83 275.024 [M-H]- 10ev: 275.024 [M-H]- (100), 195.066 [M-H-SO3]- (41), 193.051 (12), 79.9582 [SO3]- (8), 59.0138 (2), 136.054 (2), 80.9653 (2), 151.076 [M-H-SO3-COO]- (1), 149.061 (1), 123.045 (1) Dihydroferulic acid sulfate C10H12O7S 276.0312 Cluster 2 [16]
232.9763 0.93 232.976 [M-H]- 20ev: 153.0193 [M-H-SO3]- (100), 109.0294 (90.24), 135.0446 (14.23), 96.9596 [HSO4]- (5.32), 123.0434 (2.33), 61.9895 (2.23), 232.975 [M-H]- (2.12) 2,6-Dihydroxybenzoic acid sulfate - 2,6-DHBA sulfate C7H6O7S 233.9843 Cluster 1 [17]
246.9918 0.99 246.9918 [M-H]- 10ev: 167.0354 [M-H-SO3]- (100), 152.0118 (88), 123.0118 (41), 108.0218 (25), 96.906 [HSO4]- (9), 152.0639 (6), 79.9581 [SO3]- (4) Vanillic acid sulfate C8H8O7S 247.9998 Cluster 1 Manual
178.0507 1.05 178.0521 [M-H]- 10ev: 134.0612 [M-H-COO]- (100), 178.0511 [M-H]- (85.7), 77.0401 [M-H-C3H3NO3]- (41.4), 56.0147 (6.0) Hippuric acid C9H9NO3 179.0587 Cluster 2 MID 1301
277.0379 1.07 277.0379 [M-H]- 20ev: 197.0811 [M-H-SO3]- (100), 182.0574 [M-H-SO3-CH3]- (59), 79.9577 [SO3]- (29), 197.0453 (20), 125.0608 [C7H9O2] (20), 277.0371 [M-H]- (18), 122.036 (16), Unknown sulfonated metabolite M- [277.0379] rt 1.071 278.0459 Cluster 2 N.I.
261.0075 1.17 261.0081 [M-H]- 20ev: 137.061 (100), 181.0504 [M-SO3]- (14), 261.0072 [M-H]- (13), 95.0504 (8), 79.9568 [SO3]- (3) 3,4- or 3,5-Dihydroxyphenylpropionic acid sulfate - DHPPA-sulfate C9H10O7S 262.0155 Cluster 2 Unconjugated std.
305.0331 1.18 305.0343 [M-H]- 20ev: 225.0783 [M-H-SO3]- (100), 59.0147 (90), 79.9572 [SO3]- (48), 166.0626 (36), 80.9651 (13), 149.0605 (12), 165.0567 (12), 153.0552 (8), 305.0386 [M-H]- (8) Unknown sulfated metabolite M- [305.0331]- rt 1.18 C11H14O8S 306.0411 Cluster 2 N.I.
258.9917 1.22 258.9926 [M-H]- 20ev: 179.0352 [M-H-SO3]- (100), 135.045 [M-SO3-COO]- (9), 91.0553 [C7H7]- (5), 258.9926 [M-H]- (4), 93.0357 [C6H5O]- (3) 3- or 4-Caffeic acid sulfate C9H8O7S 259.9997 Cluster 2 [16]
252.0874 1.23 252.0896 [M-H]-10ev: 74.0255 [C2H4NO2]- (100), 252.0889 [M-H]- (74), 193.0769 [C10H9O4]- (10), 177.0554 [M-H-glycine]- (8) Dihydroferuloylglycine C12H15NO5 253.0954 Cluster 1 Manual
250.0711 1.32 250.0711 [M-H]- 10ev: 100.0035 (100), 149.0608 (91), 250.072 [M-H]- (80), 206.0828 [M-H-COO]- (68), 134.0377 (68), 163.0637 (29), 191.9576 (22), 175.0545 (20), 177.0545 (19) Feruloylglycine C12H13NO5 251.0791 Cluster 1 [16]
320.0436 1.42 320.0436 [M-H]- 20ev: 230.0134 [M-H-C3H6O3]- (100), 150.0557 [M-H-C3H6O3-SO3]- (29), 320.0453 [M-H]- (14), 79.9575 [SO3]- (11), 108.0444 [C6H6NO]- (9), 148.0406 (9), 80.9662 (6) Sulfonated Hydroxyphenylacetamide + C3H6O3 C11H15NO8S 321.0516 Cluster 3 HPAA std.
224.0554 1.50 224.0566 [M-H]- 10ev: 100.0042 [C3H2NO3]- (100), 224.0566 [M-H]- (38), 123.0449 [C7H7O2]- (31), 74.0230 (12), 180.0646 [M-H-COO]- (9), 165.0402 [M-H-COO-CH3]- (7) Vanilloylglycine C10H11NO5 225.0634 Cluster 1 [18]
258.9908 1.84 258.9938 [M-H]- 10ev: 215.0026 [M-H-COO]- (100), 135.045 [M-H-COO-SO3]- (22), 240.9815 [M-H-H2O]- (7), 161.0245 (6), 258.9934 [M-H]- (0.4) Unknown M- [258.9938] rt 1.84 C9H8O7S 259.9988 Cluster 2 N.I.
305.033 1.86 305.0354 [M-H]- 20ev: 123.0452 (100), 101.0244 (83), 163.0763 (62), 305.0354 [M-H]- (61), 207.0688 (8) [M-H2O-sulfate], 79.9573 [SO3]- (7), 96.9606 [HSO4]- (6), 287.0189 [M-H2O]- (2) Genipin sulfate C11H14O8S 306.041 Cluster 2 [19]
161.0449 2.02 161.0450 [M-H]- 10ev: 57.0348 [C3H5O]- (100), 99.0453 [C5H7O2]- (80), 101.0241 [M-H-C2H4O2]- (40), 161.045 [M-H]- (29), 59.0144 (11) 3-hydroxy-3-methyl-glutaricacid - HMGA C6H10O5 162.0529 Cluster 2 MID 3793
186.0765 2.63 186.0765 [M-H]- 10ev: 114.0927 [M-H-C2CO3]- (100), 142.0866 [M-H-COO]- (54), 186.0779 [M-H]- (52), 58.03 [C2H4NO]- (39), 100.0757(37), 68.0508 [C4H6N]- (18) Unknown N-containing metabolite M - [186.0765] rt 2.63 C8H13NO4 187.0845 Cluster 3 N.I.
229.1184 2.64 229.1184 [M-H]- 10ev: 229.1179 [M-H]- (100), 187.1077 [M-H-C2H2O]- (86), 58.0301 [C2H4NO] (13), 145.0978 [C6H13N2O2]- (12), 143.1194(12) Unknown N-containing metabolite M - [229.118] rt 2.64 C10H18N2O4 230.1264 Cluster 3 N.I.
232.9762 2.67 232.9779 [M-H]- 20ev: 153.0195 [M-H-SO3]- (100), 109.0297 [M-H-SO3-COO]- (29), 65.0405 (21), 67.0198 (12), 232.9776 [M-H]- (4) 3,5-dihydroxybenzoic acid sulfate - 3,5-DHBA sulfate C7H6O7S 233.9842 Cluster 3 Unconjugated std./[17]
392.1382 2.70 392.1382 [M-H]- 20ev: 124.0071 (100), 348.1493 [M-H-COO]- (54), 146.8045 (6), 79.9583 [SO3]- (3), 149.9861 (3) Unknown metabolite M- [392.1382] rt 2.70 C16H27NO8S? 393.1462 Cluster 3 N.I.
270.9754 2.81 270.9754 [M-H]- 20ev: 96.9602 [HSO4]- (100), 97.0011 (2), 79.9562 [SO3]- (2), 112.987 (1), 270.9775 (1) Unknown sulfate containing metabolite M- [270.9754] rt 2.8 C6H8O10S? 271.9834 Cluster 2 N.I.
202.0709 2.85 202.0709 [M-H]- 10ev: 202.0721 (M-H]- (100), 88.0405 [C3H6NO2] (80), 158.0818 [M-H-COO]- (56), 86.0615 (54), 87.0451 [C4H8NO] (43), 114.0194 (26), 184.0607 [M-H-H2O]- (24), 140.0706 [C7H10NO2]- (14), 70.6966 (7), 132.0306 (6) Unknown N-containing metabolite M- [202.0709] rt 2.85 C8H13NO5 203.0789 Cluster 3 N.I.
246.9906 2.85 246.9931 [M-H]- 10ev: 167.0356 [M-SO3]- (100), 246.9931 [M-H]- (44), 123.0458 [M-SO3-COO]- (13), 96.9607 [HSO4]- (8), 152.0123 [M-SO3-COO-CH3]- (8), 203.0024 (7), 167.0923 (6), 79.9581 [SO3]- (3) 3,5-Dihydroxyphenyl acetic acid sulfate - 3,5-DOPAC sulfate C8H8O7S 248.00 Cluster 3 Unconjugated std.
347.1341 2.86 347.1370 [M-H]- Unknown glucuronidated metabolite M- [347.1370-glucuronide -- > 171.1031] C15H24O9 348.1421 Cluster 3 N.I.
215.1028 2.91 215.1028 [M-H]- 20ev: 173.0925 [M-H-C2H2O]- (100), 58.03 [C2H4NO]- (51), 44.0145 (42), 143.1179 (24), 129.1032 (11), 126.0921 (6), 172.1036 (3) Unknown N-containign metabolite M - [215.103] rt 2.91 C9H16N2O4 216.1108 Cluster 3 N.I.
174.0763 2.95 174.0763 [M-H]- 10ev: 74.025 [glycine]- (100), 174.0766 [M-H]- (42), 100.0758 [M-H-C2H2O3]- (12), 128.0703 (11), 112.0374 (10), 130.085 (9), 132.067 (5), 59.0132 (4) Unknown N-containign metabolite M- [174.0763] C7H13NO4 175.0843 Cluster 3 N.I.
334.1322 2.99 334.1322 [M-H]- Unknown metabolite M- [334.132] rt 2.99 C14H25NO6S? 335.1402 Cluster 3 N.I.
139.9835 2.99 139.9859 [M-H]- 10ev: 95.9344 [M-H-COO]- (100), 139.9842 [M-H]- (94), 76.0225 [C2H6NS]- (5), 96.9419 (3), 95.9763 (2), 140.0336 (2) Unknown sulfate containing metabolite M- [139.9859] rt 2.99 ? 140.9915 Cluster 3 N.I.
216.0868 3.01 216.0868 [M-H]- 10ev: 128.0342 (100), 172.0965 [M-H-COO]- (90), 216.0872 [M-H]- (87), 198.0769 [M-H-H2O]- (31), 102.0566 (28), 128.1066 (26), 87.0459 (21), 86.0603 (20), 98.06 (12), 154.0854 (12) Unknown N-containing metabolite M- [216.0868] rt 3.01 C9H15NO5 217.0948 Cluster 3 N.I.
347.1343 3.04 347.1370 [M-H]- 10ev: 113.0247 [fragment of glucuronide] (100), 171.1031 [M-glucuronide]- (85), 347.1361 [M-H]- (30), 85.0294 [fragment of glucuronide] (25), 175.0247 (23), 59.0146 (20), 95.0132 (13) Unknown glucuronidated metabolite [m/z 171.1023 + glucuronide] C15H24O9 348.1423 Cluster 3 N.I.
166.0169 3.13 166.0169 [M-H]- 20ev: 79.9578 [SO3]- (100), 166.0167 [M-H]- (28), 106.9804 (25), 100.0411 (13), 80.9651 (9), 58.0295 (5) Unknown M- [166.017] rt 3.13 C4H9NO4S 167.0249 Cluster 3 N.I.
149.0446 3.14 149.0466 [M-H]- Tentative sugar either arabinose, xylose, or ribose C5H10O5 150.0526 Cluster 3 N.I.
144.0768 3.94 144.0790 [M-H]- 10ev: 102.0564 [M-H-CH2N2]- (100), 83.0619 (12), 84.0453 [M-H-COO-NH3]- (7), 58.0415 [C3H6O]- (6), 144.0778 [M-H]- (5), 102.099 (2) 4-Guanidinobutanoic acid C5H11N3O2 145.0848 Cluster 2 MID 4155
202.0709 4.10 202.0733 [M-H]- 10ev: 140.0716 (100), 158.0824 [M-H-COO]- (99), 202.0724 [M-H]- (93), 58.0297 [C2H4NO]- (50), 100.0401 [C4H6NO2]- (49), 116.069 (33), 69.0364 (31), 98.0612 (31), 110.0603 (28), 75.7348 (24), 345.1717 (12), 176.0227 (12) Unknown N-containing metabolite M- [202.071] rt 4.10 C8H13NO5 203.0789 Cluster 2 N.I.
159.0291 4.33 159.0291 [M-H]- Unknown M- [159.0291] rt 4.33 C6H8O5 160.0371 Cluster 2 N.I.
175.0238 4.66 175.0238 [M-H]- 10ev: 157.0134 [M-H-H2O]- (100), 87.0453 [C4H7O2]- (28), 175.0249 [M-H]- (20), 132.0666 [M-H-CH3CO]- (16), 69.0346 (15) Unknown tentative dicarboxylic acid C6H8O6 176.0318 Cluster 2 N.I.
145.0139 4.67 145.0139 [M-H]- 10ev: 101.0246 [M-H-COO]- (100), 57.0348 [C3H5O]- (25), 145.0135 [M-H]- (16), 73.0296 [C3H5O2]- (5) 2-Oxoglutaric acid C5H6O5 146.0219 Cluster 2 MID 119
133.014 4.70 133.014 [M-H]- 10ev: 115.0036 [M-H-H2O]- (100), 71.014 [C3H3O2]- (60), 133.014 [M-H]- (38), 72.993 [C2HO3]- (16), 89.0246 [M-H-COO]- (9), 87.0077 (2), 44.9976 (2) Malic acid C4H6O5 134.022 Cluster 3 MID 118
145.0135 5.05 145.0135 [M-H]- 10ev: 101.024 [M-H-COO]- (100), 57.0352 [C3H5O]- (97), 145.0116 [M-H]- (26), 82.028 (6), 127.0225 [M-H-H2O]- (6) 3-Oxoglutaric acid C5H6O5 146.0215 Cluster 3 Manual
147.029 5.19 147.029 [M-H]- Undientified M - [147.029] C5H8O5 148.037 Cluster 2  
357.0826 5.59 357.0855 [M-H]- 10ev: 357.0843 [M-H]- (100), 113.0237 [fragment of glucuronide]- (58), 181.0518 [M-H-glucuronide]- (13), 137.0596 [M-H-glucuronide-COO]- (10), 175.0238 (10), 59.0138 (10), 85.0287 [fragment of glucuronide]- (6) Glucuronidated 3,4- or 3,5-Dihydroxyphenylpropionic acid, DHPPA-glucuronide C15H18O10 358.0906 Cluster 2 [15]