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. 2024 Jun 14;14(6):333. doi: 10.3390/metabo14060333

Table 2.

Prototype compounds identified or tentatively characterized in the urine and plasma samples after oral administration of TSD.

ID [M+H]+(m/z) Formula tR
(min)		 Error
(ppm)		 ms/ms Identification ClogP Area
Urine Plasma
Alkaloids
1. 394.25839 C22H35NO5 3.51 −1.58 376.2474, 358.2376, 344.2229, 326.2116, 243.2516 Karakolidine +++
2. 394.25820 C22H35NO5 4.02 −1.42 376.2476, 358.2367, 340.2268, 328.2260, 307.4473, 218.6333 Chuanfumine +++
3. 439.25229[M-H]− C23H37NO7 4.25 0.56 392.2438, 344.2226, 295.8235, 193.8604, 146.9375 9-Hydroxysenbusine A +
4. 424.26871 C23H37NO6 6.69 −1.55 406.2584, 388.2478, 356.2207, 154.1227 Senbusine A −2.70 +++
5. 486.26941 C24H39NO9 7.01 −0.72 454.2438, 436.2322, 404.2069, 378.1887, 372.1793, 319.9836 Mesaconine ++
6. 424.26871 C23H37NO6 7.74 −1.55 406.2581, 388.2472, 356.2210, 154.1231 Senbusine B 0.16 ++
7. 378.26306 C22H35NO4 8.20 −2.18 360.2524, 342.2431, 328.2268, 242.3140 Karakoline ++
8. 408.27371 C23H37NO5 8.26 −1.81 390.2631, 372.2533, 358.2367, 340.2271 Isotalatizidine ++
9. 358.23691 C22H31NO3 9.17 −2.13 340.2265 Songorine +
10. 360.25293 C22H33NO3 9.18 −1.09 - Napelline ++
11. 330.20569 C20H27NO3 9.70 −2.07 236.8785, 170.7432, 152.4712 Hetisine ++
12. 470.27435 C24H39NO8 10.51 −1.05 - Hypaconine ++
13. 454.27933 C24H39NO7 11.33 −1.26 436.2685, 418.2609, 404.2422, 154.1227 Fuziline +++
14. 438.28445 C24H39NO6 11.58 −1.28 420.2736, 402.2617, 388.2472, 356.2214, 278.6899 Neoline +++
15. 420.27390 C24H37NO5 12.31 −1.32 402.2632, 384.2512, 370.2359, 342.2414, 324.2322, 251.1396 14-Acetylkarakoline +
16. 484.28937 C25H41NO8 12.41 −2.33 - Deoxyaconine +
17. 342.16931 C20H23NO4 12.89 −1.96 297.1120, 282.0887, 237.0910, 219.0804, 191.0860 N-Methyl-laurotetanine +++
18. 422.28931 C24H39NO5 13.64 −1.88 390.2629, 372.2517, 358.2379, 340.2238, 98.0970 Talatizamine ++++ ++
19. 420.23825 C23H33NO6 15.48 −0.86 402.2268, 370.1989, 293.7002, 154.1224 Giraldine F ++
20. 452.29996 C25H41NO6 15.54 −1.57 420.2740, 388.2465, 356.2219, 209.1644, 154.1228, 114.0916 Chasmanine ++++
21. 464.30038 C26H41NO6 16.933 −0.60 432.2740, 414.2626, 400.2474, 372.2535, 265.1608, 235.1487, 154.1225 14-Acetyltalatizamine ++++ ++
22. 606.28992 C31H43NO11 17.26 −1.60 574.2627, 556.2545, 524.2269, 506.2188, 492.1945, 261.0641, 173.0955, 105.0341 14-Benzoyl-10-OH-mesaconine ++
23. 544.28955 C30H41NO8 19.47 −0.95 512.2635, 494.2548, 480.2364, 462.2258, 390.2286, 270.0846, 105.0340 Gadenine +
24. 590.29490 C31H43NO10 19.51 −1.78 558.2616, 540.2575, 419.7593, 307.8019, 246.8854, 105.0339 14-Benzoylmesaconine ++
25. 540.29486 C31H41NO7 20.01 −1.33 504.2730, 462.2614, 382.2463, 340.2256, 322.2149, 304.2042 Aconicarchamine B +
26. 604.31060 C32H45NO10 20.53 −1.68 572.2811, 554.2750, 522.2495, 490.2176, 340.3151, 105.0341 14-Benzoylaconine ++
27. 574.30010 C31H43NO9 21.20 −1.65 542.2744, 510.2461, 304.5384, 198.1281, 105.0339 14-Benzoylhypaconine +++
28. 618.29210[M-H]− C32H45NO11 21.21 0.31 384.9167, 351.8983, 270.7405, 190.9267 14-Benzoyl-10-OH-aconine ++
29. 648.30023 C33H45NO12 21.93 −1.98 588.2775, 556.2513, 455.3509, 370.1645, 105.0340 10-OH-mesaconitine ++
30. 558.30530 C31H43NO8 22.07 −1.52 526.2800, 508.2674, 232.0710182.0626, 105.0341 14-Benzoyl-doxyhypaconine ++
31. 588.31561 C32H45NO9 22.32 −1.24 556.2905, 524.2639, 506.2443, 346.4250, 253.7027, 154.1226, 105.0341 14-Benzoyldeoxyaconine +
32. 542.31061 C31H43NO7 23.18 −1.15 510.2846, 492.2735, 482.2483, 460.2504, 154.1231 14-Benzoylneoline +
33. 632.30591 C33H45NO11 23.18 −0.63 572.2844, 540.2551, 522.2487, 508.2299, 354.1694, 105.0341 Mesaconitine * +++
34. 662.31683 C34H47NO12 23.39 −0.27 - Aconifine ++
35. 614.29553 C33H43NO10 24.17 −0.72 554.2743, 494.2534, 372.2162, 344.21622, 203.5583, 105.0341 2,3-didehydrohypaconitine +
36. 646.32135 C34H47NO11 24.58 −0.84 586.3002, 554.2727, 526.2797, 494.2520, 368.1843, 105.0340 Aconitine * ++
37. 616.31079 C33H45NO10 24.61 −0.83 556.2903, 524.2634, 496.2750, 464.2434, 338.1741, 310.1812, 105.0341 Hypaconitine * ++++
38. 600.31592 C33H45NO9 24.96 −1.32 540.2948, 508.2683, 480.2747, 476.2424, 448.2475, 354.2031, 254.4337, 105.0339 Secoyunaconitine +
39. 572.32117 C32H45NO8 24.95 −1.10 484.2688, 456.2745, 382.2002, 322.1798, 294.1857, 158.0964 14-O-Anisoylneoline +
40. 630.32635 C34H47NO10 26.07 −1.36 570.3046, 538.2788, 510.2882, 506.2528, 478.2571, 352.1898, 314.5361, 105.0341 3-Deoxyaconitine +++
41. 614.33173 C34H47NO9 27.60 −0.53 - Chasmaconitine ++
Phenolic compounds
42. 209.04474[M-H]− C10H10O5 8.56 −3.85 165.0545, 121.0281, 103.9187, 87.9238, 59.0123 Hydroxyferulic acid +++ ++
43. 433.13394[M-H]− C18H24O12 9.88 0.08 161.0442, 125.0230, 99.0436 Asperulosidic acid ++
44. 433.11407[M-H]− C21H22O10 13.87 −0.19 271.0615, 151.0024 5-Hydroxyliquiritin ++
45. 593.15137[M-H]− C27H30O15 15.51 0.29 473.1098, 383.9785, 353.0774 Vitexin II +++
46. 563.14055[M-H]− C26H28O14 15.83 −0.51 473.1089, 443.0985, 383.0769, 253.0502, 146.9367 Vitexin I +
47. 417.11890[M-H]− C21H22O9 16.74 −0.32 255.0662, 153.0182, 135.0074, 119.0488 Liquiritin * ++++
48. 505.13339 C24H24O12 18.72 −0.89 257.0809, 137.0234 Malonyl liquiritin +
49. 505.13358 C24H24O12 18.99 −0.07 257.0810, 137.0234 Malonyl liquiritin +
50. 431.13280 C22H22O9 20.26 −1.97 269.0809 Ononin ++++
51. 417.11908[M-H]− C21H22O9 20.39 −1.01 255.0662, 153.0180, 135.0072, 119.0481 Neoliquiritin 0.75 +++
52. 417.11900[M-H]− C21H22O9 20.74 −2.47 255.0662, 153.01816, 135.0074, 119.0488 Isoliquiritin 1.28 ++
53. 285.07670[M-H]− C16H14O5 21.23 −0.31 270.0536, 253.0505, 177.0182, 150.0310, 108.0203 Licochalcone B ++
54. 255.06560 C15H10O4 21.30 0.10 227.0704, 199.0754, 145.0286, 137.0234 Dihydroxyflavone ++++
55. 255.06580[M-H]− C15H12O4 21.70 −0.36 153.0180, 135.0073, 119.0487, 91.0173 Liquiritigenin * ++++ +++
56. 295.19040 C17H26O4 23.34 −0.22 177.0914, 163.0755, 137.0598, 131.0493, 99.0809 6-Gingerol ++++ ++
57. 269.04530[M-H]− C15H10O5 24.34 0.38 233.1537, 181.0644 Genistein +++
58. 255.06586[M-H]− C15H12O4 26.29 −0.49 153.0179, 135.0073, 119.0487, 91.0174 Isoliquiritigenin * ++++ +++
59. 269.08170 C16H12O4 26.58 1.04 253.0497, 237.0554, 213.0911, 118.0418, 107.0497 Formononetin * ++++ +++
60. 367.11790[M-H]− C21H20O6 27.75 −1.99 352.0944, 309.0400, 298.0476, 283.0247 Glycycoum-arim/Licocoumarione +++
61. 271.09565 C16H14O4 28.56 1.19 254.2579, 161.0599, 137.0598, 123.04440, 100.0763 Echinatin ++
62. 355.11835[M-H]− C20H20O6 28.60 −1.07 328.1265, 269.11820, 269.11820, 178.9975, 125.0230 8-Dimethylallyleriodictyol/6-Dimethylallyleriodictyol ++
63. 277.18008 C17H24O3 28.84 2.28 177.0912, 145.0649, 137.0598 6-Shogaol +++ ++
64. 355.15480[M-H]− C21H24O5 29.81 −1.06 323.1284, 233.1176, 207.1017, 135.0438, 125.0230, 109.0280 Isopentadienyl glycyrrhizoflavone ++
65. 367.11790[M-H]− C21H20O6 29.53 −2.00 309.0400, 297.0400, 284.0325, 203.0702 Glycycoum-arim/Licocoumarione +++
66. 321.11262[M-H]− C20H18O4 30.07 −1.93 306.0892, 174.9549 Licoflavone A +
67. 353.10290[M-H]− C20H18O6 30.17 −1.33 339.1187, 321.1126, 295.0613, 283.0614, 270.0535 Isolicoflanonol +++ ++
68. 353.13782 C21H20O5 30.22 −1.59 299.0906, 297.0857, 267.0653, 199.0758, 147.0441, 135.0441 Gancaonin M ++
69. 383.11273[M-H]− C21H20O7 30.39 −2.33 338.2439, 247.1310, 227.0704, 207.1015, 155.0337, 140.0101 Licopyranocoumarin +
70. 383.14828 C22H22O6 30.66 −1.50 327.0859, 299.0913, 191.0704 Glycyrin ++ ++
71. 355.15320 C21H22O5 30.94 −2.01 289.0549, 287.0553, 191.1067, 153.0548, 69.0708 Licobenzofuran/liconeolignan +++
72. 337.10780[M-H]− C20H18O5 31.02 −1.07 314.0428, 282.0531 Licoflavone C ++
73. 365.10239[M-H]− C21H18O6 30.17 −1.63 307.0244, 295.0245, 282.0169 Isoglycyrol 4.84 ++
74. 365.10236[M-H]− C21H18O6 31.12 −1.99 307.0242, 295.0243, 282.0167 Glycyrol 5.04 +++
75. 333.24170 C21H32O3 34.17 −1.99 177.0911, 145.0649, 137.0598 10-Shogaol ++
76. 279.23264[M-H]− C18H32O2 38.27 1.13 261.2219, 199.8500 Linoleic acid ++
Saponins
77. 879.40173[M-H]− 881.41516
705.38361[M+H-glcA]+
511.34122[agl+H-H2O]+ 		C44H64O18 24.011 −0.67
−1.38		 (−) 351.0557, 193.0342, 113.0229
(+) 511.3408, 493.3279, 451.3188, 141.0183		 Uralsaponin M ++
78. 837.39105[M-H]−
839.40466
469.33072[gal+H-H2O]+ 		C42H62O17 25.49 −0.79
−1.32		 (−) 351.05603, 289.05652, 193.03430, 175.02340, 113.02294
(+) 469.3304, 487.3415, 451.3209, 141.0184		 Yunganoside K2 ++
79. 837.39178[M-H]−
839.40491
469.33084[agl+H-H2O]+ 		C42H62O17 26.07 −0.84
−1.07		 (−) 351.05557, 289.05621, 193.03413, 175.02360, 113.02285
(+) 469.3304, 487.3413, 451.3198, 141.0183		 Licoricesaponin G2 +
80. 471.34613 C30H46O4 26.62 −1.41 453.33508, 425.34262, 317.21100, 235.16887, 189.16374 Glycyrrhetinic acid (enoxolone) * +
81. 821.39630[M-H]−
823.40936
647.37744[M+H-glcA]+
453.33554[agl+H-H2O]+ 		C42H62O16 26.64 1.08
−1.70		 (−) 351.05573, 193.03406, 175.02338, 113.02288
(+) 453.3354, 471.3451, 435.3259		 Glycyrrhizic acid * ++++
82. 821.39612[M-H]−
823.40936
647.37787[M+H-glcA]+
453.33585[agl+H-H2O]+ 		C42H62O16 27.65 0.86
−0.47		 (−) 351.05640, 193.03404, 175.02319, 113.02289
(+) 453.3354, 435.3257		 Uralsaponin B or Licoricesaponine K2/H2 ++

Note: * Compounds identified by comparing with reference standards; glcA: β-D-glucuronopyronosyl; agl: aglycone; +, response area below 106; ++, response area between 106 and 107; +++, response area between 107 and 108; ++++, response area above 108.