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. 2022 Aug 8;2022:1167265. doi: 10.1155/2022/1167265

Table 2.

Chemical constituents of Hedera helix characterized by UHPLC-Q-TOF-MS/MS.

Peak no. T R (min) Formula Chemical name ESI mode Error (ppm) Exact mass Found at mass MS/MS
1 5.20 C7H12O6 (−)-Quinic acid − −2.43 191.0556 191.0551 173.0467 [M-H-H2O]−
2 5.21 C16H18O9 Chlorogenic acid − 2.38 353.0873 353.0881 191.0548 [M-H-C9H6O3]−
179.0336 [M-H-C7H10O5]−
135.0443 [M-H-C8H10O7]−
3 6.46 C33H40O19 Kaempferol 3-O-rutinoside-7-O-rhamnoside − −4.82 739.2086 739.2050 593.1431 [M-H-C6H10O4]−
285.0409 [M-H-C18H30O13]−
4 6.83 C27H30O16 Rutin + 1.78 611.1612 611.1623 465.1035 [M+H-C6H10O4]+
303.0501 [M+H-C12H20O9]+
147.0661 [M+H-C18H24O14]+
129.0551 [M+H-C18H26O15]+
5 6.84 C15H10O7 Quercetin + −0.25 303.0505 303.0504 257.0463 [M+H-CH2O2]+
229.0507 [M+H-C2H2O3]+
201.0594 [M+HC3H2O4]+
165.0200 [M+H-C7H6O3]+
153.0201 [M+H-C8H6O3]+
137.0228 [M+H-C8H6O4]+
6 7.20 C21H20O12 Isoquercitrin − 4.42 463.0877 463.0897 301.0332 [M-H-C6H10O5]−
271.0227 [M-H-C7H12O6]−
255.0276 [M-H-C7H12O7]−
243.0286 [M-H-C8H12O7]−
151.0036 [M-H-C14H16O8]−
7 7.50 C27H30O15 Kaempferol 3-O-rutinoside + 1.18 595.1663 595.1670 449.1105 [M+H-C6H10O4]+
287.0559 [M+H-C12H20O9]+
147.0660 [M+H-C18H24O13]+
129.0554 [M+H-C17H22O15]+
8 7.51 C15H10O6 Kaempferol + 0.47 287.0556 287.0557 165.0204 [M+H-C7H6O2]+
153.0197 [M+H-C8H6O2]+
121.0273 [M+H-C8H6O4]+
9 7.55 C27H30O15 Kaempferol 7-O-neohesperidoside − 1.43 593.1507 593.1515 285.0375 [M-H-C12H20O9]−
151.0040 [M-H-C20H26O11]−
10 7.98 C21H20O11 Astragalin − 4.16 447.0927 447.0946 285.0378 [M-H-C6H10O5]−
255.0279 [M-H-C7H12O6]−
11 8.01 C25H24O12 Cynarin − −1.08 515.1190 515.1184 353.0837 [M-H-C9H6O3]−
335.0746 [M-H-C9H8O4]−
191.0535 [M-H-C18H12O6]−
179.0327 [M-H-C16H16O8]−
161.0230 [M-H-C18H10O8]−
135.0438 [M-H-C17H16O10]−
111.0441 [M-H-C19H16O10]−
12 8.59 C25H24O12 Isochlorogenic acid b − 0.48 515.1190 515.1192 353.0850 [M-H-C9H6O3]−
191.0541 [M-H-C18H12O6]−
179.0332 [M-H-C16H16O8]−
161.0232 [M-H-C18H10O8]−
137.0227 [M-H-C17H14O10]−
135.0442 [M-H-C17H16O10]−
13 8.63 C9H16O4 Azelaic acid − −0.72 187.0970 187.0969 125.0960 [M-H-CH2O3]−
97.0643 [M-H-C3H6O3]−
14 11.11 C60H98O27 Hederagenin 3-O-[α-L-rhamnopyranosyl-(1⟶2)-β-D-glucopyranoside], 28-O-[α-L-rhamnopyranosyl-(1⟶4)-β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl] ester − 0.54 1295.6272 1295.6279 1249.6105 [M-H]−
779.4505 [M-H-C18H30O14]−
469.1492 [M-H-C30H52O23]−
15 11.15 C59H96O27 Hederagenin 3-O-[β-D-glucopyranosyl-(1⟶2)-α-L-arabinopyranoside], 28-O-[α-L-rhamnopyranosyl-(1⟶4)-β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl] ester − 1.05 1235.6061 1235.6074 765.4362 [M-H-C18H30O14]−
469.1597 [M-H-C29H50O23]−
16 11.31 C54H88O23 Hederagenin 3-O-β-D-glucopyranoside, 28-O-[α-L-rhamnopyranosyl-(1⟶4)-β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl] ester − 1.22 1149.5693 1149.5707 1103.5582 [M-H]−
633.3921 [M-H-C18H30O14]−
469.1606 [M-H-C24H42O19]−
17 12.43 C53H86O22 Hederagenin 3-O-α-L-arabinopyranoside, 28-O-[β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl-(1⟶4)-α-L-rhamnopyranosyl] ester or hederagenin 3-O-α-L-arabinopyranoside, 28-O-[β-D-glucopyranosyl-(1⟶2)-(β-D-glucopyranosyl-(1⟶4))-α-L-rhamnopyranosyl] ester + −0.19 1075.5689 1075.5687 781.4768 [M+H-C11H18O9]+
619.4227 [M+H-C17H28O14]+
473.3664 [M+H-C23H38O18]+
455.3535 [M+H-C23H40O19]+
437.3428 [M+H-C23H42O20]+
409.3461 [M+H-C24H42O21]+
391.3356 [M+H-C24H44O22]+
18 12.44 C59H96O26 Hederacoside C + −2.89 1221.6268 − 1075.5710 [M+H-C6H10O4]+
943.5310 [M+H-C11H18O8]+
797.4673 [M+H-C17H28O12]+
635.4183 [M+H-C23H38O17]+
473.3644 [M+H-C29H48O22]+
455.3518 [M+H-C29H50O23]+
437.3419 [M+H-C29H52O24]+
427.3599 [M+H-C30H50O24]+
409.3477 [M+H-C30H52O25]+
391.3378 [M+H-C30H54O26]+
19 12.63 C53H86O22 Hederagenin 3-O-[α-L-rhamnopyranosyl-(1⟶2)-α-L-arabinopyranoside], 28-O-[β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl] ester − 2.37 1119.5587 1119.5614 1073.5461 [M-H]−
749.4439 [M-H-C12H20O10]−
603.3906 [M-H-C18H30O14]−
469.1536 [M-H-C23H40O18]−
20 13.05 C53H86O22 Hederagenin 3-O-[β-D-glucopyranosyl-(1⟶4)-α-L-rhamnopyranosyl-(1⟶2)-α-L-arabinopyranoside], 28-O-β-D-glucopyranosyl ester + −0.84 1075.5689 1075.5680 943.5316 [M+H-C5H8O4]+
797.4678 [M+H-C11H18O8]+
635.4170 [M+H-C17H28O13]+
473.3622 [M+H-C23H38O18]+
455.3528 [M+H-C23H40O19]+
437.3424 [M+H-C23H42O20]+
427.3555 [M+H-C24H40O20]+
409.3468 [M+H-C24H42O21]+
391.3371 [M+H-C24H44O22]+
21 13.93 C61H98O27 Hederagenin 3-O-[α-L-rhamnopyranosyl-(1⟶2)-α-L-arabinopyranoside], 28-O-[α-L-rhamnopyranosyl-(1⟶4)-6-O-acetyl-β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl] ester − −0.61 1307.6272 1307.6264 1261.6083 [M-H]−
791.4544 [M-H-C18H30O14]−
749.4448 [M-H-C20H32O15]−
469.1563 [M-H-C31H52O23]−
22 14.72 C59H96O25 Hederacoside B − 2.20 1203.6163 1203.6189 733.4469 [M-H-C18H30O14]−
455.3473 [M-H-C29H48O22]−
23 14.77 C48H78O18 Hederagenin 28-O-[α-L-rhamnopyranosyl-(1⟶4)-β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranoside] − 4.58 987.5165 987.5210 941.5034 [M-H]−
471.3436 [M-H-C18H30O14]−
469.1547 [M-H-C18H32O14]−
24 15.42 C47H76O17 Hederagenin 3-O-[α-L-rhamnopyranosyl-(1⟶2)-(β-D-glucopyranosyl-(1⟶4))-α-L-arabinopyranoside] (hederacolchiside A) − −1.25 957.5059 957.5047 911.4947 [M-H]−
749.4425 [M-H-C6H10O5]−
603.3794 [M-H-C12H20O9]−
471.3381 [M-H-C17H28O13]−
25 15.55 C42H68O14 Hederagenin 28-O-[β-D-glucopyranosyl-(1⟶2)-β-D-glucopyranoside] − 1.54 841.4586 841.4599 795.4481 [M-H]−
471.3440 [M-H-C12H20O10]−
26 15.78 C41H66O13 Hederagenin 3-O-[β-D-glucopyranosyl-(1⟶2)-α-L-arabinopyranoside] − 0.12 811.4480 811.4481 471.2603 [M-H-C11H18O9]−
603.3852 [M-H-C6H10O5]−
765.4429 [M-H]−
27 17.05 C29H42O6 Kendomycin − −0.24 485.2903 485.2902 467.2769 [M-H-H2O]−
439.2825 [M-H-C2H6O]−
423.2866 [M-H-C2H6O2]−
409.2718 [M-H-C3H8O2]−
28 17.68 C54H88O22 Hederagenin 3-O-[β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl-(1⟶4)-α-L-rhamnopyranosyl-(1⟶2)-α-L-rhamnopyranoside] or hederagenin 3-O-[β-D-glucopyranosyl-(1⟶2)-(β-D-glucopyranosyl-(1⟶4))-α-L-rhamnopyranosyl-(1⟶2)-α-L-rhamnopyranoside] + −1.65 1089.5846 1089.5828 927.5329 [M-H-C6H10O5]−
765.4851 [M-H-C12H20O10]−
619.4226 [M-H-C18H30O14]−
473.3637 [M-H-C24H40O18]−
455.3556 [M-H-C24H42O19]−
437.3478 [M-H-C24H44O20]−
409.3478 [M-H-C25H44O21]−
391.3277 [M-H-C25H46O22]−
29 17.74 C59H96O26 Hederagenin 3-O-[α-L-rhamnopyranosyl-(1⟶4)-β-D-glucopyranosyl-(1⟶6)-β-D-glucopyranosyl-(1⟶4)-α-L-rhamnopyranosyl-(1⟶2)-α-L-arabinopyranoside] − −0.87 1219.6112 1219.6101 1073.5520 [M-H-C6H10O4]−
749.4446 [M-H-C18H30O14]−
603.3801 [M-H-C24H40O18]−
471.3384 [M-H-C29H48O22]−
30 18.40 C36H58O9 Hederagenin 28-O-β-D-glucopyranoside or hederagenin 3-O-β-D-glucopyranoside (hederacoside B) − −0.79 679.4057 679.4052 633.3950 [M-H]−
471.3433 [M-H-C6H10O5]−
31 18.62 C42H68O13 Hederagenin 3-O-[α-L-rhamnopyranosyl-(1⟶2)-β-D-glucopyranoside] − 0.51 779.4582 779.4586 633.4022 [M-H-C6H10O4]−
471.3355 [M-H-C12H20O9]−
32 19.50 C36H56O10 Hederagenin 28-O-β-D-glucuronopyranoside or hederagenin 3-O-β-D-glucuronopyranoside (HN saponin K) − −0.35 647.3795 647.3793 471.3395 [M-H-C6H8O6]−
33 20.30 C41H66O12 α-Hederin − 1.73 749.4476 749.4489 603.3763 [M-H-C6H10O4]−
471.3498 [M-H-C11H18O8]−
34 20.38 C36H58O8 Hederagenin 3-O-α-L-rhamnopyranoside or hederagenin 28-O-α-L-rhamnopyranoside + −2.10 619.4210 619.4197 473.3735 [M-H-C6H10O4]−
455.3526 [M-H-C6H12O5]−
437.3413 [M-H-C6H14O6]−
409.3468 [M-H-C7H14O7]−
391.3366 [M-H-C7H16O8]−
35 20.82 C30H48O5 Caulophyllogenin − −0.92 487.3424 487.3419 425.3407 [M-H-CH2O3]−
423.3287 [M-H-CH4O3]−
405.3127 [M-H-CH6O4]−
393.3132 [M-H-C2H6O4]−
36 21.16 C35H56O8 Hederagenin 3-O-α-L-arabinopyranoside or hederagenin 28-O-α-L-arabinopyranoside − 1.69 649.3952 649.3963 603.3823 [M-H]−
471.3441 [M-H-C5H8O4]−
37 22.95 C36H56O9 Oleanolic acid 28-O-β-D-glucuronopyranoside or Oleanolic acid 3-O-β-D-glucuronopyranoside − 3.63 631.3846 631.3869 455.3502 [M-H-C6H8O6]−
38 23.33 C36H58O8 Oleanolic acid 28-O-glucoside or oleanolic acid 3-O-glucoside (hederacoside A2) − 0.87 663.4108 663.4114 617.4020 [M-H]−
455.3488 [M-H-C6H10O5]−
39 23.78 C18H30O3 9S-hydroxy-10E,12Z,15Z-octadecatrienoic acid − 3.51 293.2117 293.2127 275.1995 [M-H-H2O]−
231.2092 [M-H-CH2O3]−
221.1527 [M-H-C3H4O2]−
183.1375 [M-H-C7H10O]−
121.1010 [M-H-C9H16O3]−
40 24.03 C41H66O11 Oleanolic acid 3-O-α-L-arabinoside, 28-O-α-L-rhamnopyranosyl ester or oleanolic acid 3-O-α-L-rhamnopyranosyl-(1⟶2)-α-L-arabinopyranoside (β-hederin) − −1.21 733.4527 733.4518 587.3918 [M-H-C6H10O4]−
455.3483 [M-H-C11H18O8]−
41 25.16 C18H28O3 9-Oxo-10E,12Z,15Z-octadecatrienoic acid − −2.47 291.1960 291.1953 197.1171 [M-H-C7H10]−
185.1173 [M-H-C8H10]−
121.1010 [M-H-C9H14O3]−
42 25.24 C30H48O4 Hederagenin − 2.90 471.3474 471.3488 393.3153 [M-H-C2H6O3]−
43 26.31 C30H46O4 Hederagonic acid + 2.05 471.3474 471.3484 453.3367 [M+H-H2O]+
407.3302 [M+H-CH4O3]+
389.3212 [M+H-CH6O4]+
44 27.29 C18H30O3 9-Oxo-10E,12Z-octadecadienoic acid − 3.85 293.2117 293.2128 221.1532 [M-H-C3H4O2]−
197.1171 [M-H-C7H12]−
185.1160 [M-H-C8H12]−
149.0962 [M-H-C8H16O2]−
125.0958 [M-H-C9H12O3]−
45 32.56 C16H32O3 2-Hydroxypalmitic acid − −3.76 271.2273 271.2263 225.2200 [M-H-CH2O2]−
46 35.96 C39H64O5 Di-gamma-linolenic + −2.28 613.4832 613.4818 595.4736 [M+H-H2O]+
539.4475 [M+H-C4H10O]+
521.4385 [M+H-C4H12O2]+
503.3767 [M+H-C8H14]+
335.2586 [M+H-C18H30O2]+
299.2366 [M+H-C23H38]+
261.2219 [M+H-C21H36O4]+
259.2075 [M+H-C26H42]+
161.1322 [M+H-C33H56]+
147.1164 [M+H-C33H54O]