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Table 1 Proposed metabolites in five different C. calcitrapa extracts using UPLC–MS/MS4 analysis

From: New perspectives of purple starthistle (Centaurea calcitrapa) leaf extracts: phytochemical analysis, cytotoxicity and antimicrobial activity

No

tR, min

Compound name

Molecular formula,

[M–H]

Calculated mass,

[M–H]

Exact mass,

[M–H]

Δ mDa

MS2 Fragments, (% Base Peak)

MS3 Fragments, (% Base Peak)

MS4 Fragments, (% Base Peak)

Phenolic acids and derivatives

1

2.35

Gallic acida

C7H5O5

169.01425

169.01476

− 0.51

125(100)

96(14), 79(4), 81(100), 9741), 107(5)

ND

2

3.98

Dihydroxybenzoyl hexoside

C13H15O9

315.07216

315.07303

− 0.87

109(13), 152(45), 153(100), 163(9), 165(12)

108(4), 109(100)

65(14), 81(100)

3

4.32

Protocatechuic acida

C7H5O4

153.01933

153.02006

− 0.72

109(100), 110(5)

65(100), 75(8), 81(43), 227(11)

ND

4

4.52

Dihydroxybenzoic acid pentosyl-hexoside

C18H23O13

447.11442

447.11586

− 1.45

152(100), 163(65), 177(35), 179(32), 207(35)

108(100), 124(3)

ND

5

4.60

Caffeoyl-quinic acid isomer

C16H17O9

353.08781

353.08892

− 1.12

135(6), 179(31), 180(3), 191(100), 192(5)

109(28), 111(41), 127(100), 171(26), 173(69)

81(7), 83(17), 85(100), 99(33), 109(28)

6

4.64

Feruloyl-quinic acid hexoside isomer 1

C23H29O14

529.15628

529.16127

− 4.99

173(62), 191(100), 193(10), 337(17), 367(74)

85(81), 93(51), 99(21), 109(20), 127(100)

81(28), 83(100), 85(41), 99(20), 109(27)

7

4.71

Caffeoyl-hexaric acid

C15H15O11

371.06199

371.06311

− 1.13

163(15), 191(17), 209(100), 323(10), 325(17)

85(24), 191(100)

85(100), 111(6), 147(12), 173(8)

8

4.83

Caffeoyl-quinic acid hexoside

C22H27O14

515.14063

515.14317

− 2.54

191(26), 323(100), 324(13), 341(12), 353(13)

133(4), 161(100)

117(18), 133(100)

9

5.15

Feruloyl-hexaric acid

C16H17O11

385.07764

385.07870

− 1.07

191(100), 209(5), 367(5)

85(100), 129(7), 147(14), 173(4)

57(100)

10

5.17

Coumaroyl-quinic acid isomer 1

C16H17O8

337.09289

337.09357

− 0.67

119(6), 163(100), 164(7), 173(4)

119(100)

ND

11

5.24

Chlorogenic acida

C16H17O9

353.08781

353.08813

− 0.32

179(3), 191(100)

85(100), 93(57), 111(35), 127(89), 173(63)

ND

12

5.26

Feruloyl-quinic acid hexoside isomer 2

C23H29O14

529.15628

529.15889

− 2.62

175(29), 191(100), 193(8), 367(70)

85(95), 93(70), 111(28), 127(100), 173(53)

81(25), 83(26), 85(100), 99(37), 109(39)

13

5.27

p-Coumaric acida

C9H7O3

163.04007

163.04072

− 0.65

119(100)

119(100), 91(29)

ND

14

5.29

Coumaroyl hexoside

C15H17O8

325.09289

325.09305

− 0.16

119(9), 163(100), 164(8), 279(5)

119(100)

ND

15

5.38

p-Hydroxybenzoic acida

C7H5O3

137.02442

137.02493

− 0.51

93(100), 94(7), 109(3)

ND

ND

16

5.47

Feruloyl-quinic acid isomer 1

C17H19O9

367.10346

367.10347

− 0.01

134(6), 193(100), 194(4)

134(100), 149(21)

106(100)

17

5.53

Gentisic acida

C7H5O4

153.01933

153.01991

− 0.57

109(100), 110(7)

81(100), 90(20), 95(12), 168(13), 198(15)

ND

18

5.54

Feruloyl hexoside

C16H19O9

355.10346

355.10367

− 0.21

191(8), 193(100), 194(3)

134(73), 149(100), 178(69)

134(100)

19

5.76

Aesculetina

C9H5O4

177.01933

177.01989

− 0.56

131(5), 133(18), 134(9), 135(100), 147(4)

91(100), 93(12), 107(96), 180(10), 195(10)

ND

20

5.76

Caffeic acida

C9H7O4

179.03498

179.03552

− 0.54

89(3), 133(2), 135(100), 136(8)

93(15), 106(6), 107(100), 117(24), 135(35)

ND

21

5.89

Coumaroyl-quinic acid isomer 2

C16H17O8

337.09289

337.09279

0.10

163(5), 173(11), 191(100), 192(3)

85(100), 93(50), 111(38), 127(90), 173(62)

53(100), 75(76), 100(85), 113(85), 176(85)

22

6.18

Feruloyl-quinic acid isomer 2

C17H19O9

367.10346

367.10277

0.69

173(25), 191(100), 192(4), 193(5)

85(100), 93(61), 111(36), 127(82), 173(65)

57(100), 70(19), 81(19), 167(22)

23

6.30

Coumaroyl-quinic acid isomer 3

C16H17O8

337.09289

337.09246

0.43

163(4), 191(100)

85(100), 93(55), 111(43), 127(95), 173(71)

ND

24

6.49

Feruloyl-quinic acid isomer 3

C17H19O9

367.10346

367.10371

− 0.26

191(100), 192(3), 193(3)

85(100), 93(70), 111(33), 127(96), 173(68)

57(100), 80(28), 148(31), 157(27), 162(37)

25

6.82

Ferulic acida

C10H9O4

193.05063

193.05092

− 0.29

134(89), 149(100), 178(74)

134(100)

ND

26

6.82

Feruloyl pentoside

C15H17O8

325.09289

325.09482

− 1.93

193(100)

134(100), 149(40), 178(10)

ND

27

6.89

Feruloyl-isocitric acid

C16H15O10

367.06707

367.06703

0.04

111(16), 155(8), 173(100), 191(20), 321(12)

111(100), 129(9), 155(32)

ND

28

7.62

Caffeoyl-feruloyl-quinic acid isomer 1

C26H25O12

529.13515

529.13590

− 0.75

173(35), 193(6), 335(20), 349(4), 367(100)

173(100), 193(20)

59(10), 71(30), 93(100), 111(44), 155(19)

29

7.72

Dihydroxybenzoyl-feruloyl acid hexoside

C23H23O12

491.11950

491.11755

1.95

161(10), 315(100), 323(30), 447(15), 459(22)

108(13), 151(10), 153(100), 163(14), 165(19)

109(100)

30

7.97

Caffeoyl-feruloyl-quinic acid isomer 2

C26H25O12

529.13515

529.13505

0.10

173(10), 193(5), 335(6), 353(7), 367(100)

134(6), 173(100), 193(61)

71(30), 93(100), 109(18), 111(54), 155(20)

Flavonoid glycosides and aglycones

31

5.57

Apigenin 6,8-di-C-hexoside

C27H29O15

593.15119

593.15504

− 3.85

353(44), 383(23), 473(100), 503(31), 575(10)

353(100), 354(6), 383(16)

297(48), 325(100), 326(7)

32

6.56

Apigenin 8-C-hexoside

C21H19O10

431.09837

431.09879

− 0.42

311(100), 312(16), 341(18), 385(5), 413(4)

283(100), 284(12)

163(48), 183(50), 211(30), 224(27), 239(100)

33

6.67

Quercetin 3-O-glucosidea

C21H19O12–

463.08820

463.08780

0.40

300(14), 301(100), 302(9)

151(83), 179(100), 255(31), 257(14), 271(44)

151(100)

34

6.70

Quercetin 3-O-hexuronide

C21H17O13

477.06746

477.06840

− 0.93

301(100), 302(9)

201(46), 229(39), 245(96), 255(100), 283(60)

155(35), 199(19), 211(11), 227(100)

35

6.72

Scutellarein 7-O-hexuronide

C21H17O12

461.07255

461.07256

− 0.01

175(3), 285(100), 286(4)

165(22), 185(23), 239(54), 241(34), 267(100)

211(8), 223(13), 239(100)

36

6.99

Apigenin 7-O-(6"-rhamnosyl)-hexoside

C26H25O15

577.11989

577.12224

− 2.34

269(100), 270(12), 307(7)

149(35), 151(23), 201(24), 225(100), 227(21)

169(30), 181(100), 183(28), 196(20), 197(63)

37

7.10

Kaempferol 3-O-glucosidea

C21H19O11

447.09329

447.09209

1.20

255(18), 284(96), 285(100), 286(14), 327(16)

229(39), 241(31), 256(85), 257(100), 267(45)

163(52), 187(14), 213(17), 229(100), 239(24)

38

7.19

Isorhamnetin 3-O-glucosidea

C22H21O12

477.10385

477.10352

0.33

271(9), 285(11), 314(100), 315(31), 257(20)

243(21), 271(74), 285(100), 286(42), 300(16)

270(100)

39

7.23

Apigenin 7-O-hexoside

C21H19O10

431.09837

431.09827

0.10

268(15), 269(100), 270(10), 311(3)

149(33), 197(27), 201(27), 225(100), 269(32)

169(31), 181(55), 183(48), 196(32), 197(100)

40

7.29

Apigenin 7-O-hexuronide

C21H17O11

445.07764

445.07714

0.50

175(7), 269(100), 270(7)

149(41), 151(24), 201(27), 225(100), 227(21)

181(100), 183(82), 196(31), 197(49), 210(14)

41

7.45

Hispidulin 7-O-hexuronide

C22H19O12

475.08820

475.08735

0.85

175(6), 299(100), 300(15)

284(100), 285(2)

255(13), 256(100), 284(20)

42

7.48

Jaceosidin 7-O-hexoside

C23H23O12

491.11950

491.11788

1.62

313(42), 314(40), 327(13), 329(73), 476(100)

313(100), 314(30), 315(12), 327(5), 343(17)

282(18), 285(84), 295(7), 298(100), 299(10)

43

7.72

Kaempferide 3-O-hexuronide

C22H19O12

475.08820

475.08846

− 0.26

175(13), 299(100), 300(14)

284(100)

227(12), 255(100), 256(17)

44

7.80

Kaempferol 3-O-acetyl-hexoside

C23H21O12

489.10385

489.10605

− 2.20

255(37), 284(100), 285(78), 286(12), 327(20)

227(14), 255(100), 256(21)

211(67), 227(100), 255(10)

45

8.10

Scutellarein

C15H9O6

285.04046

285.04116

− 0.70

165(28), 223(33), 239(63), 267(100), 268(19)

211(7), 223(33), 225(7), 239(100)

167(7), 183(7), 195(57), 211(100)

46

8.68

Luteolina

C15H9O6

285.04046

285.04019

0.27

151(33), 175(80), 199(77), 217(64), 241(100)

197(91), 198(100), 199(87), 212(16), 213(56)

169(44), 170(100)

47

8.81

Nepetin

C16H11O7

315.05103

315.05103

0.00

300(100), 301(11)

216(100), 227(78), 228(88), 255(48), 272(67)

173(21), 187(8), 188(100), 201(25)

48

9.54

Apigenina

C15H9O5

269.04555

269.04539

0.16

149(49), 151(29), 201(30), 225(100), 227(21)

169(22), 180(20), 181(100), 183(36), 197(37)

ND

49

9.70

Kaempferola

C15H9O6

285.04046

285.04052

− 0.06

183(71), 211(98), 212(10), 213(8), 227(100)

183(100), 199(56), 250(17)

ND

50

9.72

Chrysoeriola

C16H11O6

299.05611

299.05580

0.31

284(100), 285(11)

137(68), 212(58), 227(100), 228(75), 255(36)

183(100), 199(20), 200(17), 213(5)

51

9.74

Jaceidin

C18H15O8

359.07724

359.07734

− 0.10

344(100), 345(15)

329(100)

242(12), 270(14), 286(6), 301(73), 314(100)

52

9.97

Jaceosidin

C17H13O7

329.06668

329.06647

0.21

314(100), 315(11)

299(100), 300(3)

199(6), 227(9), 243(4), 255(11), 271(100)

53

10.03

Kaempferide

C16H11O6

299.05611

299.05637

− 0.25

284(100), 285(12)

227(7), 255(100), 256(8)

ND

54

11.20

Eupatorin

C18H15O7

343.08233

343.08217

0.16

328(100), 329(10)

313(100)

270(10), 282(43), 283(10), 285(43), 298(100)

55

11.24

Centaureidin

C18H15O8

359.07724

359.07681

0.43

301(10), 344(100), 345(12)

301(100), 329(36)

258(6), 270(9), 286(100)

  1. aConfirmed using standards, the other compounds were identified according HRMS data and MSn; tR ─ retention time (min); Δ mDa ─ mean mass accuracy; "ND" ─ not detected