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Table 1 Identified natural compounds of Toddalia asiatica root bark by UPLC-QTOF-MS/MS

From: Hemostatic chemical constituents from natural medicine Toddalia asiatica root bark by LC-ESI Q-TOF MSE

No.

Rt (min)

Molecular formula

Molecular weight

−MS2 [parent ion m/z]: daughter ion

+MS2 [parent ion m/z]: daughter ion

Compound identification

Reaxys no.

SIOC SRN

CAS no.

References

1

0.826

C12H22O11

342.2964

[M−H 341.1078, M+Cl 377.0841, M−H+FA 387.1133]: 89.0233, 113.0232, 161.0442, 179.0546, 212.0526, 341.1071, 377.0841

Maltose

93798

24426146

69-79-4

2

2.894

C15H16O9

340.2821

[M−H 339.0711, M+Cl 375.0686]: 89.0231, 94.9239, 121.0282, 146.9818, 162.8379, 174.0010, 339.0715, 375.0650

Esculin

95387

60113315

531-75-9

3

3.389

C15H16O9

340.2821

[M−H 339.0710]: 89.0236, 112.9840, 146.9816, 174.0009, 219.0287, 249.0393, 339.0710

[M+H 341.0860, M+Na 363.0674, M+K 379.0404]: 77.0392, 137.0227, 147.0445, 163.0394, 191.0338, 258.9890, 341.0860, 365.1159, 379.0418

Daphnin

49440

60108006

486-55-5

4

4.623

C20H23NO4

341.4009

[M−H 340.1547]: 89.0237, 196.0516, 201.0370, 224.0467, 252.0417, 310.1077, 340.1544, 341.1578

[M+H 342.1704]: 152.0627, 165.0706, 178.0779, 189.0706, 193.0655, 222.0679, 342.1704, 343.1738

Unknown

5

5.190

C22H38O13

510.5293

[M−H 509.2231, M−3H+FA 553.2493]: 71.0132, 89.0236, 146.9822, 165.0540, 185.0050, 201.0370, 553.2500

[R-(E)]-1-[8-(β-d-Glucopyranosyloxy)-2,6-dimethyl-2-octenoate] β-d-glucopyranose

6944877

250327357

158921-22-3

6

5.401

C18H19NO4

313.3478

[M+H 314.1756]: 77.0387, 107.0493, 121.0652, 165.0701, 177.0550, 194.0726, 314.1756

N-cis-Feruloyl tyramine

5482514

65646-26-6

7

5.543

C22H24O5

368.4229

[M−H 367.1027, M−2H+Na 389.0848]: 93.0338, 134.0362, 173.0445, 191.0552, 367.1027, 389.0848

[M+H 369.1168, M+Na 391.0987]: 89.0384, 145.0286, 177.0547, 214.0892, 314.1745, 369.1168, 391.0987

5-Methoxy-8-geranyloxypsoralen

7101938

246688070

17182-52-4

[6, 14]

8

5.844

C32H38O10

582.6381

[M−H 581.2228, M−H+FA 627.2288]: 89.0237, 146.9823, 174.0011, 201.0370, 261.0766, 359.1128, 513.1600, 581.2236

Toddalin B

26980667

1538606-91-5

9

6.253

C19H21NO4

327.3743

[M+H 328.1908]: 77.0390, 115.0548, 121.0654, 156.0420, 165.0711, 254.0551, 328.1908

(S)-Isocoreximine

1552902

14140-19-3

[15]

10

7.418

C19H24O11

428.3872

[M−H 427.1245]: 119.0494, 145.0290, 176.0108, 191.0352, 235.0246, 250.0480, 265.0717, 367.1395, 427.1245

3-(4,7-Dimethoxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)benzofuran-5-yl) propanoic acid

55840374

169312-05-4

11

7.685

C28H34O15

610.5605

[M−H 609.1814]: 151.0025, 164.0105, 242.0572, 286.0471, 323.0525, 609.1819

[M+H 611.1978, M+Na 633.1788, M+Ka 649.1527]: 85.0286, 153.0186, 177.0546, 303.0867, 633.1780, 649.1512

Hesperidin

75140

60111601

520-26-3

[16]

12

8.145

C16H20O6

308.3264

[M+H 309.1345]: 91.0546, 147.0445, 177.0547, 205.0497, 219.0655, 291.1227, 309.1336

Mexoticin

1027046

18196-00-4

[15, 17]

13

9.697

C16H20O6

308.3264

[M+H 309.1342, M+Na 331.1158, 2M+Na 639.2419]: 91.0544, 119.0496, 131.0496, 147.0443, 177.0548, 205.0501, 219.0653, 309.1328, 331.1134, 347.0866, 639.2419

Toddalolactone

5445192

80582

483-90-9

[15, 17]

14

10.200

C21H18NO4

348.3719

[M+H 349.1261]: 91.0545, 127.0398, 147.0447, 177.0555, 232.0762, 246.0914, 274.0868, 290.0819, 304.0977, 332.0928

Chelerythrine

3915260

60513600

34316-15-9

15

10.600

C32H36O14

644.6198

[M−H 643.2034]: 89.0239, 135.0442, 145.0287, 191.0553, 367.1393, 409.1494

[M+H 645.2172, M+Na 667.1964]: 91.0545, 112.8961, 147.0448, 177.0554, 246.0774, 291.1245, 475.1619, 679.2251

Methyl 2,3-dibenzoyl-4-O-(2,3,4-tri-O-acetyl-α-l-rhamnopyranosyl)-α-d-xylopyranoside

24368097

99104-82-2

16

11.060

C15H16O5

276.2845

[M+H 277.1071, M+Na 299.0925, 2M+Na 575.1879]: 91.0542, 112.8963, 147.0444, 177.0546, 299.0888, 315.0627, 575.1851

Toddanin

213483-74-0

[15]

17

11.538

C12H12O5

236.2207

[M+H 237.0759, M+Na 259.0576]: 77.0385, 112.8953, 156.0428, 177.0546, 207.0651, 275.0294

5,7,8-Trimethoxycoumarin

1348912

3321716

60796-65-8

[14, 15]

18

11.765

C14H13NO4

259.2573

[M+H 260.0924]: 77.0385, 128.0496, 156.0445, 184.0392, 202.0497, 219.0650

Skimmianine

28904

60075401

83-95-4

[19]

19

11.907

C33H38O14

658.6464

[M−H 657.2189, M−H+FA 703.2241]: 89.0235, 119.9463, 134.0366, 146.9650, 174.0011, 193.0498, 367.1395

[M+H 659.2340, M+Na 681.2154]: 89.0384, 117.0339, 145.0289, 161.0601, 177.0549, 219.0655, 320.0914, 681.2154, 697.1884

Toddalin A

26980663

1538606-87-9

[18]

20

12.157

C13H11NO3

229.2314

[M+H 230.0829]: 89.0392, 116.0504, 144.0452, 172.0409, 200.0356

Gamma-fagarine

212820

60112081

524-15-2

21

12.970

C36H39NO8

613.6968

[M−H 612.2595, M−H+FA 658.2648]: 89.0233, 112.9845, 160.0153, 175.0388, 201.0367, 253.0490, 311.1149, 326.1388, 376.1546, 509.1229, 582.2126, 612.2589

[M+H 614.2753]: 133.0652, 161.0602, 205.0499, 219.0656, 243.0662, 273.1118, 294.0889, 309.1115, 463.1184, 513.1536, 614.2748

Unknown

22

13.215

C36H39NO8

613.6968

[M−H 612.2587, M−H+FA 658.2639]: 89.0232, 112.9844, 160.0151, 174.0003, 201.0360, 225.0538, 311.1143, 326.1378, 376.1529, 509.1223, 582.2113, 612.2576

[M+H 614.2740]: 105.0701, 133.0651, 161.0598, 205.0497, 219.0652, 243.0658, 273.1111, 294.0883, 309.1109, 463.1169, 614.2737

Unknown

23

13.516

C13H10O5

246.2155

[M+H 247.0597, M+Na 269.0421]: 77.0022, 95.0130, 105.0338, 133.0287, 161.0239, 175.0392, 189.0183, 217.0128, 231.0286, 269.0420, 285.0153

Isopimpinellin

262337

60107409

482-27-9

[20, 21]

24

14.311

C13H10O5

246.2155

[M+H 247.0612]: 77.0392, 91.0549, 105.0345, 133.3947, 147.0452, 161.0242, 175.0398, 217.0148, 231.0300, 246.0536

Pimpinellin

241751

43394

131-12-4

[20, 21]

25

15.365

C20H18NO4

336.3612

[M+H 337.1642, M+Na 359.1459, 2M+Na 695.3019]: 91.0544, 131.0495, 147.0444, 205.0499, 219.0657, 359.1465, 375.1199, 695.3039

Berberine

3570374

262538

2086-83-1

26

16.930

C21H17NO5

363.3634

[M+H 364.1166, M+K 402.3748]: 112.8966, 156.0426, 219.0656, 273.1121, 348.1220, 363.1085, 364.1166

Oxynitidine

345213

60114967

548-31-2

[15, 19]

27

17.250

C21H17NO5

363.3634

[M+H 364.1174, M+Na 386.0988]: 177.0575, 219.0652, 273.1118, 291.0523, 306.0756, 386.0988

Oxychelerythrine

345198

1471260

28342-33-8

[15, 19]

28

17.334

C11H10O5

222.1941

[M+H 223.0599, M+Na 244.0343]: 119.0131, 147.0079, 165.0186, 244.0343

8-Hydroxy-5,7-dimethoxycoumarin

1348197

3833130

61899-44-3

[14]

29

18.186

C16H16O4

272.2958

[M+H 273.1120, M+2K 348.1215]: 77.0381, 91.0539, 103.0540, 115.0542, 131.0493, 145.0639, 161.0594, 175.0391, 219.0651, 241.0855, 247.0597, 273.1120

Dehydrocoumurrayin

7712465

250818025

178275-73-5

[14, 18]

30

18.775

C16H18O4

274.3117

[M+H 275.1278, M+Na 297.1095]: 77.0383, 91.0540, 103.0542, 131.0494, 147.0440, 156.0426, 175.0392, 204.0417, 275.1291

Coumurrayin

1291821

951608

17245-25-9

[18]

31

19.579

C16H16O4

272.2958

[M+H 273.1127, M+Na 295.0946]: 115.0542, 161.0598, 219.0651, 273.1115, 304.0960, 332.0907, 348.1220

5,7-Dimethoxy-8-(3′-methylbuta-1,3′-dienyl) coumarin

3555720

248514399

106940-77-6

[18]

32

20.254

C16H16O4

272.2958

[M+H 273.1120]: 91.0542, 115.0547, 161.0596, 219.0651, 241.0855, 273.1119, 304.0966, 332.0911, 348.1220

6-(3-Methyl-1,3-butadienyl)-5,7-dimethoxycoumarin

27076142

[14]

33

20.306

C16H18O4

274.3117

[M+H 275.1277, M+Na 297.1095]: 90.0463, 118.0418, 161.0601, 273.1121, 275.1275, 297.1100

Toddaculine

1291825

417827

4335-12-0

[18]

34

23.153

C17H16O5

300.3059

[M+H 301.1422]: 81.0701, 114.0916, 149.0240, 156.0424, 204.0416, 217.0520, 233.0739, 273.1122, 301.1412

Phellopterin

297173

60176623

2543-94-4

[14, 15]