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Table 2 Retention time (tR), and MS data for identification of 133 compounds in GQD by HPLC Q Exactive MS

From: Comparing the antidiabetic effects and chemical profiles of raw and fermented Chinese Ge-Gen-Qin-Lian decoction by integrating untargeted metabolomics and targeted analysis

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
  1. Major signals in MS spectra were indicated in bolditalic
  2. tR retention time, P Pueraria Lobatae Radix, S Scutellariae Radix, C Coptidis Rhizoma, G Glycyrrhizae Radix et Rhizoma Praeparata cum Melle, + detected in positive ion mode, detected in negative ion mode, *confirmed with reference compounds