Skip to main content

Table 1 Tentative identification of the chemical constituents of Erdong decoction by UHPLC- MS in the negative mode

From: The combination of UHPLC-HRMS and molecular networking improving discovery efficiency of chemical components in Chinese Classical Formula

Peak no. TR (min) Formula Adduct ion Experimental mass m/z Theoretical mass m/z Mass error (ppm) Fragment ions Identification Source
1 2.21 C25H28O16 [M−H] 583.1306 583.1294 2.039 493.0986, 463.0880, 301.0355, 259.0246, 244.0359 Neomangiferin A
2 2.54 C21H22O12 [M−H] 465.1032 465.1028 0.984 303.0524, 285.0406, 177.0184 Spiraeoside S
3 4.13 C19H18O11 [M−H] 421.0778 421.0765 2.974 331.0460, 301.0355, 285.0410, 271.0248, 259.0247 Mangiferin A
4 4.33 C21H21O11 [M−H] 449.1087 449.1078 1.987 287.0553, 259.0620, 171.3426, 151.5096, 125.0229 Taxifolin 7-rhamnoside N
5 4.49 C19H18O11 [M−H] 421.0778 421.0765 3.045 331.0461, 301.0355, 285.0404, 258.0169 Isomangiferin A
6 6.30 C27H32O14 [M−H] 579.1721 579.1708 2.224 255.0662 Liquiritigenin 7,4'-di-O-glucopyranoside G
7 6.65 C26H28O14 [M−H] 563.1406 563.1395 1.826 503.1202, 473.1099, 443.0980, 383.0772, 353.0668, 203.0360 Apigenin 6-C-glucoside-8-C-arabinoside S
8 7.12 C26H28O16 [M−H] 595.1307 595.1294 2.317 300.0277, 271.0249, 243.0286, 178.9976 Quercetin-3-O-sambubioside N
9 8.01 C21H22O9 [M−H] 417.1194 417.1180 3.288 255.0661, 153.0180, 135.0074, 119.0487 Neoliquiritin G
10 8.43 C27H30O14 [M−H] 577.9597 577.9599 − 0.502 541.9865, 506.0078, 479.0923, 255.0665 5-Hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 2-O-(6-deoxy-α-l-mannopyranosyl)-β-d-glucopyranoside G
11 8.46 C21H22O9 [M−H] 417.1191 417.1180 2.640 255.0661, 153.0180, 135.0074, 119.0487 Liquiritin G
12 8.50 C26H14O12 [M−H] 517.0400 517.0402 − 0.217 471.0382, 255.0655, 153.0182, 135.0076, 119.0488 1,1',3,4',5,6',8,8'-Octahydroxy-9H,9'H-2,2'-bixanthene-9,9'-dione G
13 8.67 C26H28O13 [M−H] 547.1458 547.1446 2.180 487.1227, 457.1145, 427.1230, 367.0822, 337.0720 Isomer of chrysin 6-C-arabinoside-8-C-glucoside S
14 8.78 C26H30O13 [M−H] 549.1614 549.1603 2.135 417.1192, 255.0661, 153.0180, 135.0074, 119.0486 Liquiritin apioside G
15 8.86 C32H40O18 [M−H] 711.2114 711.2131 − 2.335 549.1617, 255.0660, 153.0176, 135.0073, 119.0487 Glucoliquirtin asioside G
16 9.22 C21H20O12 [M−H] 463.0884 463.0871 2.694 301.0346, 300.0276, 272.0300, 271.0249, 255.0298, 178.9979, 151.0024 Hyperoside N
17 9.23 C27H30O16 [M−H] 609.1450 609.1450 0.015 300.0277, 271.0251, 255.0297, 178.9977 Rutin N
18 9.26 C21H20O10 [M−H] 431.0972 431.0973 − 0.100 341.0667, 311.0565, 283.0613, 269.0455 Baicalein 7-O-β-d-glucoside S
19 9.33 C26H28O13 [M−H] 547.1457 547.1446 1.961 487.1252, 457.1140, 427.1031, 367.0822, 337.0718 Chrysin 6-C-arabinoside-8-C-glucoside S
20 9.42 C26H30O14 [M−H] 565.1558 565.1552 1.023 438.8078, 295.0642, 271.0612 Hydroxyliquiritin apioside G
21 9.48 C21H18O13 [M−H] 477.0676 477.0664 2.585 302.0389, 301.0354, 283.0245, 255.0300, 227.0338, 178.9976, 151.0024 Quercetin-3-O-glucuronide N
22 9.59 C26H28O15 [M−H] 579.1363 579.1344 3.183 284.0328, 255.0293, 227.0346, 151.0025 Leucoside N
23 9.68 C23H24O13 [M−H] 507.1151 507.1133 3.595 345.0613, 330.0382, 315.0154 Viscidulin III-6'-O-β-d-glucopyranoside S
24 9.74 C21H20O12 [M−H] 463.0884 463.0871 2.694 300.0276, 271.0250, 255.0296, 178.9976, 151.0024 Isoquercitrin N
25 9.86 C21H18O12 [M−H] 461.0716 461.0715 0.234 285.0407, 267.0296, 175.0238 Scutellarin S
26 10.61 C26H28O13 [M−H] 547.1457 547.1446 1.961 457.1138, 427.1029, 367.0823, 337.0719 Chrysin 6-C-glucoside-8-C-arabinoside S
27 11.11 C26H28O13 [M−H] 547.1458 547.1446 2.070 457.1140, 427.1028, 367.0822, 337.0720 Isomer of chrysin 6-C-arabinoside-8-C-glucoside S
28 11.26 C27H28O16 [M−H] 607.1306 607.1294 2.074 431.0992, 269.0456 Trihydroxyflavone-glycoside glucuronide S
29 11.35 C27H28O16 [M−H] 607.1303 607.1294 1.563 445.0771, 431.0983, 269.0455 Trihydroxyflavone-glycoside glucuronide S
30 11.59 C21H20O9 [M−H] 415.1035 415.1024 2.629 295.0613, 267.0663, 251.0709, 223.0758 Chrysin 8-C-β-glucoside S
31 11.82 C23H24O10 [M−H] 459.1299 459.1286 2.781 255.0661, 153.0181, 135.0073, 119.0487 6'-Acetyliquiritin G
32 11.91 C23H24O13 [M−H] 507.1144 507.1133 2.037 344.0537, 329.0306, 316.0585 Viscidulin III-2'-O-β-d-glucopyranoside S
33 12.35 C27H30O13 [M−H] 561.1610 561.1603 1.324 471.1297, 441.1179, 281.0830 5-Hydroxy-7-methoxyflavone 6-C-arabinoside-8-C-glucoside or 7-hydroxy-5-methoxyflavone 6-C-arabinoside-8-C-glucoside S
34 12.36 C22H20O12 [M−H] 475.0880 475.0871 1.847 299.0563, 284.0327 Isomer of hydroxyl oroxylin A 7-O-glucuronide or hydroxyl wogonoside S
35 12.37 C45H76O20 [M−H] 935.4862 935.4846 1.699 773.4357, 611.3790, 449.3284 Timosaponin E A
36 12.59 C51H84O25 [M−H] 1095.5241 1095.5218 2.059 933.4723, 771.4182, 404.0874 (2α,3β,5α,6β,25R)-2,6-Dihydroxyspirostan-3-yl-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranosid A
37 12.65 C32H26O11 [M−H] 585.1365 585.1391 − 4.440 549.1618, 539.2637, 417.1174, 297.0774, 255.0662 {3-(4-Hydroxy-3-methoxyphenyl)-6-[(2R,3R)-3,5,7-trihydroxy-4-oxo-3,4-dihydro-2H-chromen-2-yl]-2,3-dihydro-1,4-benzodioxin-2-yl}methyl benzoate G
38 12.66 C26H30O13 [M−H] 549.1614 549.1603 2.026 255.0661, 153.0180, 135.0074, 119.0487 Isoliquiritin apioside G
39 12.67 C56H92O29 [M−H] 1227.5653 1227.5641 1.024 1065.51123, 933.47205、771.41693, 447.31555 3-O-β-d-xylopyranosyl(1 → 4)-[β-d-glucopyranosyl(1 → 2)]-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl-(25S)-5β-furostane-22-methoxy-3β,26-diol As
40 12.69 C48H82O19 [M−H] 961.5383 961.5367 1.678 799.4863, 637.4363, 475.3780, 391.2874 20-Glc-Rf P
41 12.75 C45H74O19 [M−H] 917.4751 917.4741 1.138 755.4233, 593.3687, 553.3922, 364.0068, 319.1408 Timosaponin D A
42 12.80 C51H84O24 [M−H] 1079.5287 1079.5269 1.677 933.4645, 917.4766, 771.4186, 609.3615 Alliumoside B A
43 12.87 C23H24O10 [M−H] 459.1300 459.1286 3.107 255.0660, 153.0180, 135.0073, 119.0488 6'-acetylisoliquiritin G
44 12.91 C21H22O9 [M−H] 417.1190 417.1180 2.281 255.0661, 153.0179, 119.0487 Isoliquiritin G
45 12.93 C21H18O11 [M−H] 445.0776 445.0765 2.477 270.0490, 269.0455, 251.0349, 241.0509, 223.0393 Baicalin S
46 12.95 C26H30O13 [M−H] 549.1620 549.1603 3.137 255.0659, 153.0182, 135.0073, 119.0490 Licuraside G
47 13.01 C45H76O20 [M−H] 935.4857 935.4846 1.111 773.4354, 611.3803, 449.3252 Timosaponin E1 A
48 13.36 C21H22O9 [M−H] 417.1195 417.1180 3.599 255.0662 Neoisoliquiritin G
49 13.41 C23H22O13 [M−H] 505.0992 505.0977 3.055 329.0667, 314.0435, 299.0198, 271.0250, 255.0291, 227.0344, 175.0237 5,6'-Dihydroxy-6,7-dimethoxyflavone 2'-O-β-d-glucuronide S
50 13.53 C21H20O11 [M−H]- 447.0930 447.0922 1.861 271.0613, 243.0660 Dihydrobaicalin S
51 13.60 C42H72O14 [M−H+HCOOH] 845.4905 845.4893 1.381 799.4837, 637.4315, 475.3803, 273.3054 Ginsenoside Rg1 P
52 13.61 C48H82O18 [M−H+HCOOH] 991.5499 991.5472 2.671 945.5428, 783.4907, 637.4326, 475.3786 Ginsenoside Re P
53 13.69 C35H36O15 [M−H] 695.1979 695.1970 1.199 549.1608, 531.1499, 255.0664, 153.0185, 135.0074, 119.0486 Licorice-glycoside B G
54 13.81 C36H38O16 [M−H] 725.2089 725.2076 1.722 549.1630, 531.1491, 255.0660, 153.0179, 135.0072, 119.0488 Licorice-glycoside A G
55 13.92 C21H18O11 [M−H] 445.0761 445.0765 − 0.961 270.0488, 269.0455, 249.0541, 241.0501, 225.0548 Apigenin 7-O-glucuronide S
56 14.12 C50H84O23 [M−H] 1051.5342 1051.5320 2.107 919.4982, 889.4860, 757.4376, 595.3851, 433.3344 Officinalisnin-II As
57 14.20 C45H76O19 [M−H] 919.4907 919.4897 1.103 757.4378, 595.3847, 433.3319 3-O-β-d-glucopyranosyl (1 → 2)-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl-(25S)-5β-furostane-3β,22α,26-triol As
58 14.24 C50H84O23 [M−H] 1051.5327 1051.5320 0.709 919.4877, 889.4722, 757.4381, 594.6215, 418.5930 25-Epi-officinalisnin II As
59 14.28 C45H76O21 [M−H] 951.4787 951.4795 − 0.878 633.9669, 475.0884 (2α,3β,5α,22S)-26-(β-d-Glucopyranosyloxy)-2,5,22-trihydroxyfurostan-3-yl 4-O-β-d-glucopyranosyl-β-d-glucopyranoside As
60 14.41 C45H74O17 [M−CO2−H] 841.4950 841.4944 0.716 781.4773, 637.4346, 475.3789 Ginsenoside mRg1 P
61 14.45 C48H74O20 [M−H] 969.4695 969.4690 0.525 922.5041, 825.9856, 760.4498, 471.1639, 351.0573 (3β,22β)-22-(β-d-Glucopyranosyloxy)-11-oxoolean-12-en-3-yl 2-O-β-d-glucopyranuronosyl-β-d-glucopyranosiduronic acid G
62 14.46 C56H92O27 [M−H+HCOOH] 1241.5817 1241.5797 1.584 1241.5817, 1195.5740, 1079.5382, 1033.5212, 917.4714, 755.4238, 455.1436 Ophiopojaponin G O
63 14.55 C21H18O11 [M−H] 445.0772 445.0765 2.409 270.0491, 269.0456, 251.0346, 241.0503, 225.0552, 223.0392 Isomer of baicalin S
64 14.60 C45H76O19 [M−H] 919.4914 919.4897 1.831 757.4382, 595.3838, 433.3329 3-O-β-d-Glucopyranosyl (1 → 2)-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl-(25R)-5β-furostane-3β,22α,26-triol As
65 14.61 C51H86O24 [M−H] 1081.5433 1081.5425 0.740 919.4806, 757.4385, 595.3859 26-(Hexopyranosyloxy)-22-hydroxyfurostan-3-yl hexopyranosyl-(1 → 2)hexopyranosyl-(1 → 4)hexopyranoside A
66 14.65 C21H18O10 [M−H] 429.0821 429.0816 1.018 253.0505, 175.0236, 113.0229 Chrysin-7-O-β-d-glucuronid S
67 14.79 C22H20O11 [M−H] 459.0937 459.0922 3.338 283.0614, 269.0411, 268.0377, 241.0481, 175.0235 Oroxylin A-7-O-β-d-glucuronide S
68 14.81 C51H84O23 [M−H] 1063.5324 1063.5320 0.362 901.4807, 755.4263, 468.3537, 423.1946 Timosaponin BIV A
69 14.91 C22H20O12 [M−H] 475.0882 475.0871 2.247 299.0563, 284.0327 Isomer of hydroxylwogonin glucuronide S
70 14.93 C56H92O28 [M−H] 1211.5714 1211.5691 1.875 1079.5255, 917.4763, 865.0001, 755.4222 Timosaponin C1 A
71 15.02 C45H76O19 [M−H] 919.4921 919.4897 2.571 841.4293, 757.4416, 595.3847, 459.0930 Timosaponin BII A
72 15.59 C22H20O11 [M−H] 459.0932 459.0922 2.205 283.0614, 269.0431, 268.0378, 240.0425, 175.0237 Wogonoside S
73 15.70 C57H94O27 [M−H] 1209.5912 1209.5899 1.088 1047.5446, 901.4795, 883.4755, 755.4213, 737.4127, 431.3182 (2α,3β,5α,25R)-2-Hydroxyspirostan-3-yl β-d-glucopyranosyl-(1 → 2)-[4-O-[(2S,3R,4S)-3-hydroxy-4-(hydroxymethyl)-4-methyltetrahydro-2-furanyl]-β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside A
74 15.91 C51H84O22 [M−H] 1047.5380 1047.5371 0.868 901.4722, 885.4497, 755.4229 Protoneodioscin As
75 16.06 C51H84O22 [M−H] 1047.5382 1047.5371 1.107 901.4749, 883.4813, 755.4178, 413.2992 Protodioscin As
76 16.09 C50H84O25 [M−H] 1083.5170 1083.5218 − 4.452 1047.5375, 901.4825, 802.9248, 755.4275, 487.1885 (2α,3β,5α,22S,25R)-26-(β-d-Glucopyranosyloxy)-2,5,22-trihydroxyfurostan-3-yl β-d-xylopyranosyl-(1- > 3)-β-d-glucopyranosyl-(1- > 4)-β-d-galactopyranoside As
77 16.29 C50H84O22 [M−H] 1035.5374 1035.5371 0.289 903.5004, 889.4836, 757.4378, 595.3881, 433.3307 3-O-α-l-Rhamnopyranosyl(1 → 4)-[β-d-xylopyranosyl (1 → 2)]-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl-(25S)-5β-furostane-3β,22α,26-trio As
78 16.69 C51H86O23 [M−H] 1065.5487 1065.5476 1.028 903.4990, 757.4362, 595.3870, 445.8120 (5α,22R)-26-(β-d-Glucopyranosyloxy)-22-hydroxyfurostan-3-yl 6-deoxy-α-l-mannopyranosyl-(1 → 4)-[α-l-mannopyranosyl-(1 → 2)]-β-d-glucopyranoside A
79 16.87 C48H72O22 [M−H] 999.4452 999.4431 2.041 837.3885, 351.0569 24-hydroxy-licoricesaponin A3 G
80 16.90 C51H86O23 [M−H] 1065.5483 1065.5476 0.680 903.4954, 757.4395, 739.4266, 595.3826, 433.3332 3-O-α-l-rhamnopyranosyl (1 → 4)-[β-d-glucopyranosyl(1 → 2)]-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl(25R)-5β-furostane-3β,22α,26-triol As
81 17.24 C45H76O18 [M−H] 903.4975 903.4948 0.363 757.4323, 595.3828, 433.3293 Aspacochioside A As
82 17.47 C45H76O18 [M−H] 903.4968 903.4948 2.256 757.4388, 595.3868, 433.3327 Isomer of aspacochioside A As
83 17.53 C44H64O19 [M−H] 895.3964 895.3958 0.619 456.4406, 429.6882, 351.0563 Hydroxy acetoxyglycyrrhizin G
84 17.75 C42H62O18 [M−H] 853.3855 853.3852 0.303 351.0568 22-Hydroxy-licoricesaponin G2 G
85 19.31 C48H72O21 [M−H] 983.4494 983.4482 1.184 821.3983, 351.0575 Licorice-saponin A3 G
86 19.61 C42H60O17 [M−H] 835.3760 835.3747 1.560 801.4187, 443.5862, 381.5747, 351.0575 formylglycyrrhizin acid G
87 19.71 C50H82O22 [M−H] 1033.5227 1033.5214 1.267 901.4716, 739.4283, 577.3704, 427.2860 3-O-β-d-xylopyranosyl (1 → 4)-[β-d-glucopyranosyl (1 → 2)]-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl-(25S)-5β-furostane-20 (22)-ene-3β,26-diol As
88 19.73 C44H64O18 [M−H] 879.4027 879.4009 2.068 351.0570, 193.0346, 175.0236, 113.0229 22β-Acetoxyglycyrrhizin G
89 19.78 C45H74O18 [M−H] 901.4808 901.4791 1.873 739.4278, 577.3749, 356.5983 Xilingsaponin B A
90 19.83 C42H62O17 [M−H] 837.3911 837.3903 0.935 351.0570 Licorice-saponin P2 G
91 19.89 C51H84O23 [M−H] 1063.5335 1063.5320 1.396 901.4749, 739.4255, 577.3785, 445.3186 3-O-β-d-xylopyranosyl(1 → 4)-[β-d-glucopyranosyl(1 → 2)-β-d-glucopyranosyl(1 → 2)]-β-d-glucopyranosyl-26-O-β-d-glucopyranosyl-(25S)-furostane-5-ene-22-methoxy-3β,26-diol As
92 20.01 C57H94O26 [M-CO2-H] 1149.6069 1149.6051 1.566 1149.6069, 1107.5963, 945.5444, 783.4910, 621.4361, 459.3843 Ginsenoside mRb1 P
93 20.04 C47H80O17 [M-H+HCOOH] 965.4387 965.4377 1.025 919.4950, 758.4404, 497.1143, 435.1156 Gypenoside IX P
94 20.09 C48H76O19 [M−H] 955.4913 955.4897 1.699 793.4381, 731.4389, 613.3751, 569.3850, 523.3790, 455.3533 Ginsenoside Ro P
95 20.11 C56H92O25 [M−CO2−H] 1119.5964 1119.5946 1.675 1077.5857, 945.5567, 915.5332, 783.4905, 621.4422, 459.3855 Ginsenoside mRb2 P
96 20.13 C45H74O17 [M−H] 885.4871 885.4842 3.199 739.4278, 577.3763, 484.2304 3-O-[{α-L-rhamnopyranosyl-(1 → 4)}{β-d-glucopyranosyl}]-26-O-[β-d-glucopyranosyl](25S)-5β-furost-20(22)-en-3β,26-diol As
97 20.16 C42H60O16 [M−H] 819.3818 819.3815 2.085 351.0568, 193.0346, 175.0237, 113.0229 Licorice-saponin E2 G
98 20.18 C44H60O17 [M−H] 859.3739 859.3747 -0.904 837.3852, 797.3743, 351.0557 Methyllicorice-saponin Q2 G
99 20.19 C42H62O17 [M−H] 837.3916 837.3903 1.521 351.0570 Macedonoside A G
100 20.28 C48H72O20 [M−H] 967.4548 967.4533 1.498 645.3641, 541.9834, 497.1151, 435.1159 (3β,22β)-23-Hydroxy-29-oxo-22,29-epoxyolean-12-en-3-yl 6-deoxy-α-L-mannopyranosyl-(1 → 2)-β-d-glucopyranuronosyl-(1 → 2)-β-d-glucopyranosiduronic acid G
101 20.29 C44H64O17 [M−H] 863.4081 863.4082 2.575 351.0566, 193.0343, 175.0241, 113.0229 22β-Acetoxyglycyrrhaldehyde G
102 20.45 C42H62O17 [M−H] 837.3915 837.3903 1.377 351.0568 Licorice-saponin Q2 G
103 20.47 C39H66O14 [M−H] 757.4377 757.4369 1.132 595.3846, 465.2493, 357.2007, 271.7701, 161.0441 Anemarrhenasaponin I or II A
104 20.50 C42H62O16 [M−H] 821.3968 821.3954 1.678 352.0605, 351.0569, 193.0346, 175.0237, 113.0229 Glycyrrhizin acid G
105 20.52 C42H64O16 [M−H] 823.4128 823.4111 1.778 721.3478, 351.0557, 193.0344, 175.0237, 113.0226 Licorice-saponin J2 G
106 20.74 C42H62O17 [M−H] 837.3918 837.3903 1.736 351.0573 Licorice-saponin G2 G
107 20.75 C39H62O14 [M−H+HCOOH] 799.4072 799.4111 − 4.869 799.4072, 753.4070, 205.0709, 163.0600, 119.0335 Ophiopojaponin Ra O
108 20.79 C42H64O15 [M−H] 807.4177 807.4161 1.873 351.0572, 193.0346, 175.0236, 113.0230 Licorice-saponin B2 G
109 20.88 C42H62O16 [M−H] 821.3971 821.3954 2.043 352.0600, 351.0571, 193.0346, 175.0237, 113.0229 Licorice-saponin H2 G
110 20.95 C39H64O14 [M−H] 755.4227 755.4212 1.982 593.3716, 201.9089 Timosaponin AII A
111 21.06 C42H62O16 [M−H] 821.3972 821.3954 2.201 352.0616, 351.0570, 193.0346, 175.0238, 113.0229 Licorice-saponin K2 G
112 21.13 C42H62O16 [M−H] 821.3970 821.3954 1.897 352.0634, 351.0573, 193.0345, 175.0237, 113.0229 Apioglycyrrhizin G
113 21.57 C42H62O15 [M−H] 805.4006 805.4005 0.090 351.0572, 193.0349, 175.0240, 113.0229 Licorice-saponin C2 G
  1. A: Anemarrhe naerhizoma, S: Scutellariae radix, N: Nelumbinis folium, G: Glycyrrhizae radix, As: Asparagi radix, O: Ophiopogonis radix, P: Ginseng radix