Table 1 Differential metabolites between ULE and FLE as determined by UHPLC–Orbitrap–MS/MS analyses

From: Biotransformation by beta glucosidase enhances anti inflammatory metabolites in licorice using untargeted metabolomics

No.

Tentave identification

VIPa

pcorr (1)b

FDR (adjusted p)

RT (min)

Measured mass

M.W.c

MS/MS Fragments

Molecular

Δ ppm

MSI Leveld

[M–H]−

[M + H]+

formula

Flavonoids

1

Isoschaftoside

2.06

−0.9

2.3E-02

5.04

563.1421

565.1549

564

563.14209 > 473.0812, 353.0684, 325.0797

C26H28O14

2.6

1

2

Violanthin

2.37

−0.88

3.6E-02

5.5

577.1575

579.1707

578

577.1574 > 457.3513, 353.10236, 383.11429

C27H30O14

2.06

2

3

Glucoisoliquiritin

1.47

−0.58

2.1E-01

5.52

579.173

603.1691 d

580

579.1729 > 255.1798, 134.9097, 91.0257

C27H32O14

1.8

2

4

7,3’,4’-Trihydroxyflavone

1.43

−0.7

1.3E-01

6.25

269.0454

271.061

270

269.0452 > 255.0555, 133.0294

C15H10O5

−0.62

2

5

Isoliquiritin apioside

8.08

−0.99

3.6E-04

6.33

549.1714

551.1747

550

549.1613 > 255.0660, 256.0694

C26H30O13

−0.76

2

6

Isoliquiritin

5.48

−0.63

2.1E-01

6.46

417.12

419.1333

418

417.11996 > 255.2517, 135.1898, 91.03238

C21H22O9

2.05

2

7

Licorice glycoside D1

3.37

−0.97

2.7E-03

6.54

695.1978

697.2122

696

695.19781 > 549.2880, 531.2537, 255.0068

C35H36O15

−0.48

2

8

Licorice glycoside C1

3.08

−0.96

3.2E-03

6.57

725.2081

727.2229

726

725.20813 > 549.3326, 255.0275

C36H38O16

−0.8

2

9

Licochalcone B

2.83

−0.97

3.2E-03

6.7

285.0766

287.0923

286

285.0764 > 270.0531, 150.0322, 109.0294

C16H14O5

2.87

2

10

Isoliquiritigenin

20.64

0.94

6.1E-03

6.82

255.0664

257.0804

256

255.06638 > 135.1759, 91.0236

C15H12O4

0.38

1

11

Genkwanin

1.65

−0.9

2.5E-02

6.92

283.061

285.0765

284

283.0609 > 268.0374, 224.0476

C16H12O5

3.2

1

12

Licorice glycoside D2

2.84

−1

1.2E-04

6.92

695.1978

697.2122

696

695.19781 > 549.2880, 531.2537, 255.0068

C35H36O15

−0.48

2

13

Licorice glycoside C2

2.55

−0.99

8.0E-04

6.93

725.2081

727.2229

726

725.20813 > 549.33264, 255.0275

C36H38O16

−0.8

2

14

O-Desmethylangolensin

1.37

0.99

8.3E-05

8.31

257.0818

259.097

258

257.0817 > 210.9495, 136.0167

C15H14O4

3.46

2

Isoflavones

15

Ononin

8.7

−0.99

3.1E-04

6.44

475.1251e

431.133

430

475.12509 > 267.2481, 252.1672, 223.0128

C22H22O9

1.06

2

16

Daidzein

2.92

−0.95

8.9E-03

6.69

253.051

255.0648

254

253.05096 > 135.0087, 117.0345, 153.0193

C15H10O4

1.3

1

17

Dihydrogenistein

2.3

0.84

3.8E-02

7.33

271.0609

273.0764

272

271.0610 > 151.0036, 119.0502, 135.0451

C15H12O5

3.11

2

18

Genistein

1.86

-0.94

8.9E-03

7.39

269.0457

271.0592

270

269.0457 > 253.0460, 237.0556, 175.0399

C15H10O5

0.53

1

19

Biochanin A

1.39

−0.75

1.1E-01

7.46

283.061

285.0765

284

283.0609 > 268.0374, 224.0476

C16H12O5

3.2

2

20

Glyasperin C

3.29

−1

8.3E-05

8.61

355.1557

357.1688

356

355.1557 > 193.0500, 313.1443, 299.0922

C21H24O5

1.61

2

21

Licoisoflavanone

10.65

−1

6.8E-06

8.9

353.1024

355.1168

354

353.1029 > 125.0243, 298.0480, 284.0325

C20H18O6

1.19

2

Triterpenoids & derivatives

22

Licorice saponin G2 isomer

6.87

0.99

8.0E-04

7.19

837.3907

839.4047

838

837.39069 > 351.3049, 192.9847, 130.9745

C42H62O17

−0.88

2

23

Licorice saponin G2

4.87

−0.76

7.9E-02

7.5

837.3907

839.4047

838

837.39069 > 351.3049, 192.9847, 130.9745

C42H62O17

−0.88

2

24

Licorice saponin E2

1.2

−0.79

6.3E-02

7.52

819.3826

821.395

820

819.3835 > 351.2945, 192.9604, 131.0227

C42H60O16

2.31

2

25

Glycyrrhizin

10.05

−0.86

3.8E-02

7.73

821.3978

823.4087

822

821.3978 > 351.2245, 192.9746, 130.9805

C42H62O16

1.61

2

26

Licorice saponin B2

4.12

−0.96

3.9E-03

8.3

807.4194

809.431

808

807.4158 > 351.0562, 193.0351, 113.0244

C42H62O15

2.64

2

27

Glycyrrhetic acid 3-O-glucuronide

4.93

1

8.4E-05

8.73

645.3639

647.377

646

645.3637 > 113.0243, 255.2327, 469.3319

C36H54O10

0.88

2

28

24-Hydroxyglycyrrhetic acid

2.74

1

6.7E-06

9.24

485.327

487.3435

486

485.3268 > 441.3371, 202.9646, 146.9385

C30H46O5

1.8

2

29

18beta-glycyrrhetinic acid

2.93

0.99

1.2E-04

10.46

469.3318

-

470

469.3318 > 112.9855, 425.3425

C30H46O4

1.17

1

Organic acids

30

Citric acid

6.06

0.99

1.2E-04

0.66

191.0195

-

192

191.0195 > 111.0087, 87.0087, 85.0295

C6H8O7

−0.94

1

31

Succinic acid

1.98

0.91

1.5E-02

0.85

117.0194

-

118

117.0193 > 73.0294, 99.0087

C4H6O4

0.33

1

32

3-hydroxy-3-phenylpropanoic acid

6.95

−0.7

1.3E-01

1.23

165.0561

-

166

165.0561 > 59.0138, 121.0659, 93.0646

C9H10O3

2.17

2

33

2-Hydroxyisocaproic acid

4.37

0.97

3.2E-03

3.21

131.0714

-

132

131.0713 > 85.0658

C6H12O3

0.57

1

34

Phenyllactic acid

5.52

0.99

8.2E-05

5.04

165.0563

-

166

165.0563 > 147.0451, 119.0502, 72.9931

C9H10O3

3.37

1

35

4-Hydroxybenzoic acid

1.32

0.81

5.9E-02

6.14

137.0245

-

138

137.0243 > 93.0345

C7H6O3

0.53

2

Amino acids & derivatives

36

Pyroglutamic acid

4.04

1

2.1E-05

0.66

128.0354

130.0502

129

128.0353 > 85.0295, 55.0189

C5H7NO3

0.3

1

37

N-(1-Deoxy-1-fructosyl)phenylalanine

2.05

1

6.7E-06

0.85

326.1248

328.1382

327

326.12479 > 236.0849, 308.1101, 278.0674

C15H21NO7

0.81

2

38

Phenylalanine

1.06

0.93

9.0E-03

0.85

164.0721

166.0859

165

164.07208 > 147.03967, 103.03818

C9H11NO2

−2.02

1

Sugar & Sugar alcohol

39

Mannitol

27.44

1

6.7E-06

0.64

181.0723

205.0678 d

182

181.07228 > 163.0532, 101.0205, 83.0749

C6H14O6

2.86

1

40

Sucrose

27.81

−0.97

3.2E-03

0.66

341.1098

365.1046 d

342

341.1098 > 179.2282, 142.99258, 89.05035

C12H22O11

2.54

2

Etc

41

Glycycoumarin

4.2

−1

8.2E-05

8.52

367.1186

369.1316

368

367.11859 > 309.2633, 265.0255, 237.1333

C21H20O6

1.49

2

42

10-hydroxy-12(Z)-octadecenoic acid

2.16

1

4.4E-06

10.23

297.2434

-

298

297.2432 > 279.2326, 169.1232

C18H34O3

−0.27

2

  1. aVIP variable in projection, bpcorr(1) partial correlation coefficient, cM.W molecular weight, d[M+Na]+, e[M + FA-H]−, MSI (Metabolomics Standardas Initiative) level.
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