Table 2 Retention time (tR), and MS data for identification of 133 compounds in GQD by HPLC Q Exactive MS
Source | t R (time) | Compound | Formula | Experimental m/z | Error ppm | Mode | MS/MS (m/z) | Structure type |
|---|---|---|---|---|---|---|---|---|
P1 | 6.85 | 3’-Hydroxypuerarin-4’-O-glucoside | C27H30O15 | 595.16559 | − 0.263 | + | 475, 433, 415, 397, 379, 367, 337, 313, 283 | C-glycoside-O-glu |
P2 | 7.19 | Puerarin-4’-O-glucoside | C27H30O14 | 579.17120 | 0.636 | + | 417, 399, 381, 351, 321, 297, 267, 255 | C-glu-O-glu |
P3 | 7.80 | 3’-Methyoxy puerarin-4’-O-glucoside | C28H32O15 | 609.18237 | 1.598 | + | 447, 429, 411, 393, 381, 365, 351, 327, 297 | C-glycoside-O-glu |
P4 | 8.03 | Mirificin-4’-O-β-D-glucoside | C32H38O18 | 709.19830 | 0.859 | − | 457, 429 | C-glycoside-O-glu |
P5 | 8.33 | Daidzein-4’,7-O-glucoside | C27H30O14 | 579.17084 | 0.014 | + | 417, 255 | O-glu |
P6 | 8.77 | 3’-Hydroxypuerarin* | C21H20O10 | 433.11276 | − 0.377 | + | 415, 397, 379, 367, 337, 313, 283 | C-glu |
P7 | 8.89 | 3’-Methoxy-4’-O-glucoside-daidzin | C28H32O15 | 609.18262 | 2.008 | + | 447, 285 | O-glu |
P8 | 9.63 | 3’-Hydroxypuerarin xyloside | C26H28O14 | 565.15509 | − 0.163 | + | 433, 415, 397, 379, 367, 337, 313, 283 | C-glycoside-O-xyl |
C1 | 10.07 | Dihydro-11-Hydroxy-stepholidine-glucoside | C25H31NO10 | 506.20200 | − 0.073 | + | 344, 326, 295, 277 | alkaloid-O-glu |
P9 | 10.30 | 6’’-O-α-D-glucopyranosylpuerarin | C27H30O14 | 579.17059 | − 0.242 | + | 417, 399, 381, 351, 321, 297, 267 | C-glu-O-glu |
P10 | 10.43 | 3’-Hydroxydaidzin | C21H20O10 | 433.11389 | 0.967 | + | 271 | O-glu |
P11 | 10.62 | Puerarin* | C21H20O9 | 417.11786 | − 0.356 | + | 399, 381, 363, 351, 321, 297, 267, 255 | C-glu |
P12 | 10.73 | Mirificin | C26H28O13 | 549.16016 | − 0.107 | + | 417, 399, 363, 351, 321, 297, 267 | C-glycoside-O-api |
P13 | 11.16 | 3’-Methoxypuerarin | C22H22O10 | 447.12827 | − 0.678 | + | 429, 411, 381, 351, 327, 297 | C-glu |
P14 | 11.22 | 6’’-O-Xylosylpuerarin | C26H28O13 | 549.15997 | − 0.541 | + | 417, 399, 363, 351, 321, 297, 267 | C-glycoside-O-xyl |
C2 | 11.52 | Magnoflorine* | C20H23NO4 | 342.16996 | − 0.189 | + | 297, 265, 250, 237 | alkaloid |
P15 | 11.65 | 3’-Methoxypuerarin6’’-O-D-api | C27H30O14 | 579.17053 | − 0.521 | + | 447, 429, 411, 393, 381, 365, 351, 327, 297 | C-glu |
C3 | 12.03 | Norisocorydine | C19H22NO4 | 328.15411 | − 0.225 | + | 313, 298, 282 | alkaloid |
S1 | 12.11 | 2’,3,5,6’,7-Pentahydroxyflavanone | C15H12O7 | 303.05096 | 1.031 | − | 285, 275, 217, 177 | flavanones aglycone |
P16 | 12.15 | 3’-Methoxydaidzin 6’’-O-D-api | C27H34O11 | 579.17108 | 0.428 | + | 255 | O-glu |
P17 | 12.19 | 5’-Hydroxypuerarin | C21H20O10 | 433.11328 | 0.824 | + | 415, 397, 367, 313, 283 | C-glu |
P18 | 12.57 | Daidzin* | C21H20O9 | 417.11807 | 0.147 | + | 255 | O-glu |
C4 | 12.75 | 11-Hydroxy-stepholidine-glucoside | C25H30NO10 | 505.18610 | − 0.322 | + | 342, 324, 275 | alkaloid-O-glu |
P19 | 13.02 | Genistein-8-C-xyl-glucoside | C26H28O14 | 565.15619 | 1.008 | + | 433, 415, 397, 367, 313, 283 | C-glycoside O-xyl |
P20 | 13.40 | BiochaninA-7-O-glucoside | C22H22O10 | 447.12933 | 1.692 | + | 285, 270, 253, 225 | O-glu |
C5 | 13.61 | O,O’-Dimethoxyl magnoflorine | C21H25NO5 | 372.18045 | − 0.099 | + |  | alkaloid |
P21 | 13.72 | Genistein-8-C-api-glucoside | C26H28O14 | 565.15503 | − 0.269 | + | 433, 415, 367, 337, 313, 283 | C-glycoside-O-api |
P22 | 14.48 | PuerosideA | C29H34O14 | 607.20148 | − 0.652 | + | 592, 461, 299, 281, 253 | O-glu |
P23 | 14.53 | Daidzein 4’-O-glucoside | C21H20O9 | 417.11771 | − 0.229 | + | 255, 199 | O-glu |
G1 | 14.79 | Liquiritengin-glucopyranoside-(1→2)-β-D apiofuranoside | C26H30O13 | 549.16101 | 1.352 | − | 255, 153, 135, 119 | O-glu-O-api |
S2 | 14.96 | Chrysin-6-C-pen-8-C-hex | C26H28O13 | 547.14851 | 2.180 | − | 487, 457, 427, 367, 337, 281 | C-glu |
S3 | 15.00 | Viscidulin I | C15H10O7 | 301.03522 | 1.241 | − | 283, 273, 257, 229, 193, 151 | flavone aglycone |
C6 | 15.10 | 13-Hydroxyepiberberine | C20H17NO5 | 352.11787 | − 0.149 | + | 336, 322, 294 | alkaloid |
S4 | 15.36 | Chrysin-6-C-pen-8-C-hex | C26H28O13 | 547.14600 | 2.527 | − | 487, 457, 427, 367, 337, 281 | C-glu |
G2 | 15.38 | Liquiritin apioside | C26H30O13 | 549.16046 | 0.351 | − | 255, 153, 135, 119, 91 | O-glu |
G3 | 15.44 | Liquiritin* | C21H22O9 | 417.11917 | 2.784 | − | 255, 153, 135, 119 | O-glu |
S5 | 15.83 | Chrysin 6-C-α-L-arabinoside-8-C-β-D-glucoside | C26H28O13 | 547.14581 | 2.18 | − | 487, 457, 427, 367, 337, 281 | C-glu |
P24 | 15.90 | Neopuerarin | C21H20O9 | 417.11755 | − 1.100 | + | 399, 381, 363, 351, 321, 297, 267 | C-glu |
P25 | 15.97 | 6-D-xylose-Genistin | C26H28O14 | 565.15768 | 2.408 | + | 433, 271 | O-glu |
S6 | 16.14 | Scutellarein 7-β-D-glucuronoside | C21H18O12 | 461.07266 | 2.619 | − | 285, 267 | O-gluA |
S7 | 16.16 | Chrysin 6-C-β-L-arabinoside-8-C-β-D-glucoside | C26H28O13 | 547.14587 | 2.290 | − | 487, 457, 427, 367, 337, 281 | C-glu |
C7 | 16.28 | Stecepharine | C21H25NO5 | 372.18015 | − 0.399 | + | 222, 207, 189 | alkaloid |
S8 | 16.31 | Viscidulin III 2’-O-glucoside | C23H24O13 | 507.11469 | 2.707 | − | 345, 330, 315 | O-glu |
S9 | 16.43 | Acteoside | C29H36O15 | 623.19861 | 2.509 | − | 461, 161, 179 | O-glu |
P26 | 16.44 | Genistin* | C21H20O10 | 433.11334 | 0.417 | + | 271 | O-glu |
P27 | 16.46 | Kuzubutenolide A | C23H24O10 | 461.14017 | − 4.053 | + | 299, 281, 253, 239 | O-glu |
S10 | 16.52 | Chrysin 6-C-β-D-glucoside- 8-C-α-L-arabinoside | C26H28O13 | 547.14569 | 1.961 | − | 457, 427, 367, 337, 321 | C-glu |
P28 | 16.74 | Formononetin-8-C-glucoside-O-api | C27H30O13 | 563.17694 | 1.023 | + | 431, 413, 311, 281 | C-glu-O-api |
C8 | 16.88 | Groenlandicine | C19H15NO4 | 322.10712 | − 0.821 | + | 307, 279 | alkaloid |
C9 | 16.99 | Demethyleneberberine | C19H17NO4 | 324.12283 | -0.205 | + | 308, 266, 281 | alkaloid |
S11 | 17.02 | chrysin6-hexosyl-8-C-pentosyl | C26H28O13 | 547.14612 | 1.503 | − | 457, 427, 367, 337, 321 | C-glu |
P29 | 17.05 | Formononetin-8-C-glucoside-O-xyloside | C27H30O13 | 563.17554 | − 0.670 | + | 431, 413, 311, 281 | C-glu |
P30 | 17.10 | 6′′-O-Malonyl daidzin | C24H22O12 | 503.11804 | − 0.362 | + | 255 | O-glu |
S12 | 17.19 | Chrysin 6-C-β-D-glucoside-8-C-β-L- arabinoside | C26H28O13 | 547.14575 | 2.070 | − | 457, 427, 367, 337, 321 | C-glu |
P31 | 17.22 | 4′-Methoxypuerarin | C22H22O9 | 431.13364 | − 0.043 | + | 413, 395, 377, 335, 311, 281 | C-glu |
S13 | 17.34 | 5,2′,6′-Trihydroxy-7,8-dimmethoxy flavone -2′-glucoside | C23H24O12 | 491.11948 | 2.194 | − | 329, 314, 299 | O-glu |
S14 | 17.36 | Isoacteoside | C29H36O15 | 623.19843 | 1.383 | − | 461, 161, 179 | O-glu |
C10 | 17.38 | Oxyberberine | C20H17NO5 | 352.11789 | − 0.059 | + | 337, 336, 322, 308, 294 | alkaloid |
C11 | 17.64 | Oxidated palmatine | C21H21NO5 | 368.14893 | − 0.314 | + | 352, 336 | alkaloid |
G4 | 18.06 | Pyrroside B | C26H30O14 | 565.15649 | 2.315 | − | 271, 151 | O-glu |
G5 | 18.59 | 5-Hydroxylliquiritin | C21H22O10 | 433.11404 | 1.117 | − | 271, 151, 119 | O-glu |
S15 | 19.12 | 5,7,2′,6′-Tetrahydroxyflavone | C15H10O6 | 285.04050 | 3.984 | − | 241, 199, 133, 151 | flavone aglycone |
P32 | 19.21 | 6′′-O-Acetyl daidzin | C23H22O10 | 459.12839 | − 0.183 | + | 255 | O-glu |
C12 | 19.49 | Columbamine | C20H19NO4 | 338.13849 | − 0.576 | + | 323, 308, 294 | alkaloid |
S16 | 19.58 | 5,7,2′-Trihydroxy-6-methoxyflavone 7-O-glucuronide | C22H20O12 | 475.08975 | 0.848 | − | 299, 284, 175, 113 | O-gluA |
C13 | 19.70 | Epiberberine | C20H18NO4 | 336.12274 | − 0.876 | + | 321, 320, 292 | alkaloid |
C14 | 19.98 | Coptisine* | C19H13NO4 | 320.09174 | 0.017 | + | 292, 262 | alkaloid |
C15 | 20.13 | Jatrorrhizine | C20H19NO4 | 338.13855 | − 0.398 | + | 323, 308, 294 | alkaloid |
P33 | 20.81 | Sophoraside A or isomer | C24H26O10 | 473.14496 | 0.737 | − | 311, 267, 252 | O-glu |
G6 | 20.89 | Isoliquiritin apioside | C26H30O13 | 549.16150 | 0.191 | − | 255, 153, 135, 119, 91 | O-glu |
S17 | 21.68 | Scutellarein* | C15H10O6 | 285.04071 | 4.720 | − | 267, 239, 166, 137, 117 | flavone aglycone |
P34 | 22.04 | Ononin* | C22H22O9 | 431.13361 | − 0.101 | + | 269 | O-glu |
G7 | 22.13 | Licuraside | C26H30O13 | 549.16040 | 0.133 | − | 255, 153, 135, 119 | O-glu |
G8 | 22.23 | Isoliquiritin* | C21H22O9 | 417.11948 | 1.471 | − | 255, 153, 135, 119 | O-glu |
S18 | 22.44 | Baicalein 7-β-D-glucoside | C21H20O10 | 433.11276 | − 0.163 | + | 271 | O-glu |
S19 | 22.50 | Baicalin* | C21H18O11 | 445.09216 | 0.028 | − | 269, 241, 223, 175, 113 | O-gluA |
S20 | 22.60 | Eriodictyol | C15H12O6 | 287.05630 | 1.285 | − | 218, 161, 125 | flavanones aglycone |
C16 | 22.65 | Worenine+CH2+2H | C21H21NO4 | 352.15433 | − 0.285 | + | 334, 320 | alkaloid |
P35 | 23.45 | Daidzein* | C15H10O4 | 255.06509 | − 0.374 | + | 227, 199, 181, 153 | flavanones aglycone |
G9 | 23.47 | Neoisoliquiritin | C21H22O9 | 417.11954 | 1.531 | − | 255, 153, 119 | O-glu |
C17 | 23.56 | Worenine | C20H15NO4 | 334.10721 | − 0.174 | + | 319, 306, 291 | alkaloid |
G10 | 23.59 | Licochalcone B | C16H14O5 | 285.07687 | 3.929 | − | 270, 253, 191, 150 | chalcones aglycone |
G11 | 24.13 | Licorice glycosideB | C35H36O15 | 695.19727 | 0.223 | − | 549, 531, 399, 255 | O-glu |
G12 | 24.18 | Liquiritigenin* | C15H11O4 | 255.06641 | 4.801 | − | 237, 153, 135, 119, 91 | flavanones aglycone |
P36 | 24.21 | Isoononin | C22H22O9 | 431.13461 | 0.951 | + | 269 | O-glu |
C18 | 24.53 | Palmatine* | C21H21NO4 | 352.15417 | − 0.468 | + | 337, 336, 322, 308, 294 | alkaloid |
P37 | 24.69 | BiochaninA | C16H12O5 | 283.06110 | 3.533 | − | 268, 240, 211 | flavone aglycone |
P38 | 24.82 | Apigenin* | C15H10O5 | 269.04568 | 1.230 | − | 241, 225, 213, 197 | flavone aglycone |
S21 | 24.88 | Naringenin 7-O-β-D-glucuronide | C21H20O11 | 447.09454 | 2.352 | − | 271, 243, 113 | O-gluA |
C19 | 24.96 | Berberine* | C20H17NO4 | 336.12274 | − 0.876 | + | 321, 320, 306, 292 | alkaloid |
C20 | 25.27 | Demethylcoptichine | C30H25NO8 | 528.16552 | − 0.073 | + | 334, 319, 304 | alkaloid |
S22 | 25.52 | Norwogonin-8-Oglucuronide | C21H18O11 | 445.07779 | 2.814 | − | 269, 251, 241 | O-gluA |
S23 | 26.15 | Trihydroxymethoxyflavone-Oglucoside | C22H22O11 | 461.10977 | 1.932 | − | 299, 284, 283, 211, 173 | O-glu |
S24 | 26.18 | Hydroxyl oroxylin A-7-O-glucuronide | C22H20O12 | 475.08813 | 1.028 | − | 299, 284 | O-gluA |
S25 | 26.40 | 4′-Hydroxylwogonin | C16H12O6 | 299.05606 | 1.0455 | − | 271, 227, 211, 165, 133 | O-gluA |
S26 | 26.57 | Norwogonin-7-Oglucuronide | C21H18O11 | 445.07748 | 2.117 | − | 269, 251, 241 | O-gluA |
S27 | 26.98 | Chrysin-7-O-glucuronide | C21H18O10 | 431.09763 | 0.828 | + | 255 | O-gluA |
S28 | 27.00 | Oroxylin A-7-O-glucuronide | C22H20O11 | 459.09357 | 3.001 | − | 283, 268, 175, 113, 85 | O-gluA |
S29 | 27.38 | Hydroxyl wogonoside | C22H20O12 | 475.08810 | 0.998 | − | 299, 284 | O-gluA |
P39 | 27.49 | Isoformononetin | C16H12O4 | 267.06650 | 1.315 | − | 252, 223, 199 | isoflavone aglycone |
C21 | 27.84 | 13-Methylberberine | C21H19NO4 | 350.13864 | − 0.045 | + | 335, 334, 320, 318, 306 | alkaloid |
S30 | 28.09 | Baicalein 6-O-glucuronide | C21H18O11 | 445.07791 | 3.083 | − | 269, 241, 225, 197 | O-gluA |
C22 | 28.16 | Demethylcoptichine | C30H25NO8 | 528.16595 | 1.244 | + | 334, 319, 304 | alkaloid |
S31 | 28.52 | Wogonoside* | C22H20O11 | 459.09348 | 2.815 | − | 283, 268, 175, 113, 85 | O-gluA |
S32 | 29.11 | 5,7-Dihydroxy-6,8-dimethoxyflavone-7-O glucuronide | C23H22O12 | 489.10565 | 2.898 | − | 313, 298, 283 | O-gluA |
P40 | 30.47 | Genistein* | C15H10O5 | 269.04572 | 4.721 | − | 241, 225, 183, 159 | isoflavone aglycone |
S33 | 30.53 | 5,7,4′-Trihydroxy-8-methoxyflavone | C16H12O6 | 299.05637 | 4.532 | − | 284, 231, 136, 94 | flavone aglycone |
G13 | 31.48 | Licorice saponin A3 | C48H72O21 | 983.44867 | 0.435 | − | 821, 351 | O-gluA-gluA |
S34 | 31.88 | Norwogonin | C15H10O5 | 269.04578 | 1.330 | − | 251, 241, 223 | flavone aglycone |
G14 | 32.14 | 22β-Acetoxylglycyrrhizic acid | C44H64O18 | 879.40295 | 2.341 | − | 351 | O-gluA-gluA |
S35 | 32.20 | 5,7,2′-Trihydroxy-6-methoxyflavone | C16H12O6 | 299.05630 | 1.285 | − | 284, 255 | flavone aglycone |
G15 | 32.19 | Licorice saponin G2 | C42H62O17 | 837.39185 | 1.819 | − | 351, 193 | O-gluA-gluA |
S36 | 32.19 | Trihydroxydimethoxyflavone | C17H14O7 | 329.06674 | 3.528 | − | 314, 299 | flavone aglycone |
S37 | 32.40 | Baicalein* | C15H10O5 | 269.06000 | − 0.100 | − | 251, 241, 223, 213, 197 | flavone aglycone |
S38 | 32.64 | Trihydroxy-methoxyflavone | C16H12O6 | 299.05627 | 4.198 | − | 284, 165, 137 | flavone aglycone |
G16 | 32.73 | Isoliquiritigenin* | C15H11O4 | 255.06633 | 4.566 | − | 237, 153, 119, 91 | chalcones aglycone |
G17 | 32.80 | Glycyrrhizic acid* | C42H62O16 | 821.39655 | 1.385 | − | 351 | O-gluA-gluA |
P41 | 32.97 | Formononetin* | C16H12O4 | 267.06647 | 4.810 | − | 252, 223 | isoflavone aglycone |
G18 | 33.07 | Glycyrrhizin isomer | C42H62O16 | 821.39642 | 1.227 | − | 351 | O-gluA-gluA |
G19 | 33.39 | Licorice saponin C2 | C42H62O15 | 805.40094 | 0.433 | − | 351, 193 | O-gluA-gluA |
G20 | 33.50 | Licorice saponin B2 | C42H64O15 | 807.41724 | 1.093 | − | 351, 193 | O-gluA-gluA |
S39 | 33.54 | Skullcapflavone | C18H16O7 | 343.08255 | 1.321 | − | 328, 313, 298, 285 | flavone aglycone |
G21 | 33.72 | Liconeolignan | C21H22O5 | 353.13947 | 1.120 | − | 338, 321, 295, 283, 269 | others |
S40 | 33.77 | Wogonin* | C16H12O5 | 283.06140 | 4.593 | − | 268, 239, 163 | flavone aglycone |
S41 | 33.78 | Chrysin | C15H10O4 | 255.06497 | − 0.215 | + | 238, 214 | flavone aglycone |
S42 | 33.90 | Dihydroxy-dimethoxyflavone | C17H14O6 | 315.08600 | − 0.315 | + | 300, 285 | flavone aglycone |
C23 | 33.95 | Berberastine | C20H18NO5 | 352.11774 | − 0.209 | + | 336, 322, 308 | alkaloid |
S43 | 34.03 | Oroxylin A | C16H12O5 | 283.06137 | 4.487 | − | 268, 239, 163 | flavone aglycone |
S44 | 34.21 | Tenaxin I | C18H16O7 | 343.08252 | 1.321 | − | 268, 239, 163 | flavone aglycone |
G22 | 34.40 | Licoisoflavone A | C20H18O6 | 353.10330 | 1.335 | − | 284, 267, 243, 216, 201, 83 | isoflavone aglycone |
G23 | 34.45 | Licochalcone A | C21H22O4 | 337.14484 | 1.404 | − | 305, 281, 243, 229, 201 | chalcones aglycone |
G24 | 35.03 | Glabrone | C20H16O5 | 335.09271 | 1.310 | − | 305, 291, 275, 213, 199, 107 | isoflavone aglycone |
G25 | 35.03 | Licoisoflavone B | C20H16O6 | 351.08755 | 1.235 | − | 283, 265, 241, 199, 83 | isoflavone aglycone |