Table 3 Metabolites composition of T. boudieri and T. claveryi analyzed via UPLC-MS.

From: Terfezia boudieri and Terfezia claveryi inhibit the LPS/IFN-γ-mediated inflammation in RAW 264.7 macrophages through an Nrf2-independent mechanism

No

Proposed structure

Molecular formula

Error in ppm

MS2

T. boudieri

T. claveryi

M − H

M + H

RT

Amino acids and carbohydrates

1

N, N′-Di-α-hexosyl-butanediamine

C16H32N2O10

4.4

342, 234

 + 

  

413.211

0.743

2

Choline Glutamate

C10H22N2O5

6.2

233, 216, 198

 + 

  

251.159

0.777

3

Eletefine

C19H19NO5

 − 8.5

324, 306, 288

 + 

  

342.134

0.811

4

N-Methyl-L-glutamic acid

C6H11NO4

5.4

146,127

 + 

  

162.076

0.849

5

N-Glucosyl arginine

C12H24N4O7

7.3

319, 175

 + 

  

337.172

0.856

6

Arginine

C6H14N4O2

5.5

158

 + 

  

175.118

0.859

7

Xylonic acid

C5H10O6

1.9

147, 129, 87, 75

 + 

 

165.041

 

0.946

8

Unknown amino sugar

C9H17NO7

5.5

234, 216, 170

 + 

 + 

 

252.108

0.955

9

Sucrose

C12H22O11

 − 0.1

162

 

 + 

341.109

 

0.994

10

Fructosyl valine

C11H21NO7

0.1

118, 262, 126

 + 

  

280.137

1.014

11

N-Fructosyl pyroglutamate

C11H17NO8

 − 1.3

128, 170, 200, 243, 272

 + 

 + 

290.088

 

1.021

12

N-fructosyl isoleucine

C12H23NO7

0.1

276, 258, 230, 212, 86

 + 

 + 

 

294.155

1.036

13

Pyroglutamic acid

C5H7NO3

0.3

  

 + 

1,280,353

130.05

1.463

14

Unknown amino sugar

C16H23NO10

 − 1.3

244, 287, 306

 + 

 + 

388.125

 

1.864

15

N-Fructosyl phenylalanine

C15H21NO7

4.7

310, 292, 264, 178, 166

 + 

 + 

 

328.137

2.682

16

N-acyl homoserine lactone

C9H16NO4

3.4

186, 168, 99

 + 

  

202.107

2.74

17

Unknown amino sugar

C14H21NO9

 − 1.9

189, 273

 

 + 

346.111

 

3.168

18

Pipecolate

C6H10NO2

3

113

 + 

  

128.071

3.275

19

Stachydrine

C7H14NO2

3.8

 

 + 

  

144.102

3.911

20

N-Acetyl-L-leucine

C8H15NO3

-4.7

130

 

 + 

172.099

 

5.232

21

N-Acetylaspartic acid

C14H25NO5

 − 0.2

214

 

 + 

286.166

 

11.748

Alkaloids

22

Vincapyridine C

C12H16NO4

4.4

220, 179

 + 

 + 

 

238.107

5.273

23

4-Hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl

C9H18NO2

 − 0.1

85

 

 + 

 

172.133

6.202

24

Puniceusine F

C14H16NO4

2.6

244, 216,192

 

 + 

 

262.107

6.38

25

Hyrtiosine A

C10H9NO3

4.3

176, 164

 + 

  

192.066

6.418

26

Piperlongumine

C17H19NO5

1.7

212.1056

 

 + 

316.119

318.134

6.578

27

augustine N-oxide

C17H20NO5

3.1

288, 258, 242

 

 + 

 

318.134

8.918

28

Fabiocinine

C15H14NO3

4.1

210, 178, 105

 + 

  

256.097

11.654

29

Tersone G

C14H12NO2

2.8

208, 172, 148, 105

 + 

  

226.086

12.186

30

Norargemonine

C20H22NO4

3.6

294, 266

 + 

  

340.153

13.641

31

2-methyl-6-(9-phenylnonyl) piperidine-3,4-diol

C21H36NO2

3.3

236, 220

 + 

  

334.274

14.17

32

17,20-dihydroxybuxadine-M

C25H42NO2

1.8

238, 222

 + 

  

388.321

15.838

Amides

33

Dodecanamide

C12H26NO

 − 1.4

 

 + 

  

200.201

14.79

34

Octadecenoic acid amide

C18H35NO

2

247, 212, 163, 97

 

 + 

 

282.279

17.6

Fatty acids/esters

35

Hydroxytetradecanedioic acid

C14H26O5

 − 2

  

 + 

273.171

 

10.415

36

Octadecenedioic acid

C18H32O4

 − 0.7

311, 293

 + 

 + 

311.222

313.237

11.467

37

Hydroxyoctadecanedioic acid

C18H34O5

 − 0.1

229, 211

 + 

 + 

329.233

 

11.666

38

Dodecanedioic acid

C12H22O4

0.3

229, 211, 167

 + 

 

229.145

 

11.979

39

Octadecenedioic acid

C18H33O4

3.8

295, 277

 

 + 

 

313.236

12.129

40

Trihydroxy trioxo docosanoic acid

C22H37O8

4.2

411, 393, 293

 + 

  

429.248

12.606

41

Unknown fatty acyl amide

C23H44NO3

3

357, 340, 277

 

 + 

 

382.332

12.723

42

Hexadecanedioic acid

C16H30O4

 − 0.7

 

 + 

 

285.207

 

13.137

43

Octadecanedioic acid

C18H34O4

0.3

295, 277, 183, 129

 + 

 + 

313.238

 

13.528

44

Hydroxy-octadecanoic acid

C18H35O4

3.3

279, 261, 243

 + 

 + 

 

315.253

13.569

45

Hydroxy-octadecenoic acid

C18H33O3

3.1

261, 243

 + 

  

279.231

14.064

46

Octadecatetraenoic acid

C18H28O2

3.3

231, 176, 163

 

 + 

 

277.215

14.181

47

Unknown oxylipid

C22H40O7

 − 0.2

 

 + 

 

415.27

 

14.406

48

Hydroxy-octadecadienoic acid

C18H32O3

 − 0.9

295, 277, 195

 + 

 + 

295.228

 

15.023

49

Hydroxy-octadecatrienoic acid

C18H30O3

0.4

 

 + 

 

293.212

295.227

15.288

50

Hydroxyoctadecanoic acid

C18H36O3

1.3

 

 + 

 

299.258

 

16.119

51

Oxo-octadecadienoic acid

C18H28O3

0.8

275, 223, 205, 187

 + 

  

293.21

16.522

52

Octadecatrienoic acid

C18H30O2

 − 0.5

261, 223, 209, 173

 + 

 

277.218

279.232

16.812

53

Hydroxyhexadecanoic acid

C16H32O3

1

 

 + 

 + 

271.228

 

16.992

54

linoleoyl glycerol

C21H38O4

1.8

337, 263, 245

 + 

 + 

 

355.284

16.962

55

Hexadecenoic acid

C16H30O2

0.4

 

 + 

 

253.217

 

17.239

56

Linoleic acid

C18H32O2

 − 0.1

263, 245

 + 

 + 

279.233

281.248

17.46

57

Hexadecanoic Acid

C16H32O2

 − 0.4

229, 173

 + 

 

255.233

257.248

17.646

Sterols

58

Hydroxystigmast-4-en-

C29H48O2

3.1

297, 233

 

 + 

 

429.372

15.852

3-one

59

dankasterone A

C28H40O3

3.3

407, 297, 165

 

 + 

 

425.304

15.976

60

Matsutoic acid

C18H30O3

4.4

277, 259, 198, 180

 

 + 

 

295.224

16.202

61

Unknown sterol

C19H30O3

2.4

289, 251

 

 + 

 

307.227

16.367

62

Paxisterol

C28H42O4

2.3

341

 

 + 

 

443.316

17.034

Phenolic compounds

63

Hydroquinone-glucose-O-hexoside

C12H15O7

4.1

161, 109, 101

 + 

 

271.081

 

1.624

64

Scopoletin

C10H8O4

3.7

 

 + 

 

191.034

 

10.757

65

Flavonol 3-O-petosyl hexoside

C26H28O12

 − 5.7

487, 443

 + 

 

531.154

 

11.667

66

isomyrtucommulone B

C24H30O6

2.8

281, 119

 

 + 

 

415.212

13.786

Miscellaneous

67

Malic acid

C4H6O5

 − 1.5

115, 87,71, 87

 + 

 + 

133.014

 

1.011

68

Unknown hexose

C6H10O6

 − 0.6

129, 99, 89, 85, 75

 + 

 + 

177.041

 

1.028

69

Citric acid

C6H8O7

 − 0.6

129, 111, 87

 

 + 

191.02

 

1.028

70

Succinic acid

C4H6O4

 − 0.8

117, 99, 73

 + 

 

117.019

 

1.555

71

Citramalic acid

C5H8O5

3.2

147, 103, 87

 

 + 

147.029

 

1.597

72

isoquinoline-1,4-diol

C10H13NO2

4.1

103, 89

 + 

  

162.055

3.327

73

Menisdaurin D

C14H20N13O7

2.3

225, 180

 + 

  

314.123

3.543

74

Homotyrosine methyl ether

C11H15NO3

4.2

192, 96

 + 

  

210.113

3.774

75

Dihydroxybenzenebutanoic acid O hexoside

C16H22O9

5.3

313

 + 

 

357.117

 

4.677

76

Cinnamic acid

C9H8O2

2.9

  

 + 

147.045

 

5.761

77

Unknown nitrogenous

C12H17NO3

0.2

128, 89

 + 

 + 

 

224.128

6.99

78

Unknown aromatic

C14H10O3

6.2

124

 + 

 

225.054

 

7.553

79

Unknown amino sugar

C12H19NO6

4

144

 

 + 

272.113

 

7.567

80

Phenylacetic acid

C8H8O2

1.3

 

 + 

 

135.041

 

7.639

81

unknown terpenoid

C16H18O5

4.4

181, 163

 

 + 

 

291.123

7.765

82

1-(1-b-Glucopyranosyl)-1H-indole-3-carbaldehyde

C15H17NO6

 − 8.7

289, 261

 

 + 

306.101

 

12.179

83

Amino-octadecene-triol

C18H38NO3

4

298, 280

 + 

  

316.283

12.723

84

Unknown terpenoid

C19H25O5

4.2

289, 247, 203

 + 

  

333.17

13.042

85

Nitrogenous lipid

C18H29NO3

3

290, 210, 192

 

 + 

 

308.221

14.666

86

LysoDGTSA 16:0

C26H51NO6

2.1

456, 236

 

 + 

 

474.377

15.593

87

unknown diterpene

C20H34O2

1.8

277, 261, 243, 219, 205, 187, 173, 163, 109, 95

 

 + 

 

307.263

16.9