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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