UPLC-QTOF-MS with a chemical profiling approach for holistic quality evaluation between a material reference of Wen Dan decoction and its commercial preparations

Yang, Siyu; Chen, Gan; Yuan, Man; Zou, Yan; Zhang, Hongmei; Xu, Hongxi

doi:10.1186/s13020-023-00767-z

Table 3 Chromatographic and mass spectral data of the 107 compounds analysed by UPLC-QTOF-MS/MS

From: UPLC-QTOF-MS with a chemical profiling approach for holistic quality evaluation between a material reference of Wen Dan decoction and its commercial preparations

No	t_R (min)	Identification	Selected ion	Calculated mass (Da)	Measured mass (Da)	Mass error(ppm)	Formula	MS Fragmentation	Type	Source	Refs.
1^a	0.63	Adenosine	[M + H]⁺	268.1033	268.1037	1.3	C₁₀H₁₃N₅O₄	136.0616[M + H-C₅H₈O₄]⁺, 119.0345[M + H-C₅H₈O₄-NH₃]⁺	Alkaloid	PRP, AFI, BCT	[7]
2	0.69	Luteolin 3′,4′-dimethyl ether 7-O-rutinoside	[M + H]⁺	623.2001	623.1976	−4.0	C₂₉H₃₄O₁₅	477.1390[M + H-Rha]⁺, 459.1351[M + H-Rha-H₂O]⁺, 273.0624[M + H-Rha-Glc-CH₂-CO]⁺	Flavonoid	AFI	[7]
3^a	0.73	Synephrine	[M + H]⁺	168.1018	168.1018	−0.1	C₉H₁₃NO₂	150.0901[M + H-H₂O]⁺, 134.0593[M + H-H₂O-CH₄]⁺, 119.0499[M + H-H₂O-NH₂CH₃]⁺, 107.0489[M + H-H₂O-CHNHCH₃]⁺	Alkaloid	CRP, AFI	[7]
4	0.97	Furfural	[M + H]⁺	97.0283	97.0283	−0.2	C₅H₄O₂	81.0329[M + H–O]⁺, 69.0336[M + H–CO]⁺	Other type	PRP	[9]
5	1.00	Aminobenzoic acid	[M + H]⁺	138.0545	138.0544	−0.6	C₇H₇NO₂	120.0439[M + H-H₂O]⁺, 94.0651[M-COOH]⁺	Organic acid	PRP	[9]
6	1.01	Valine	[M + H]⁺	118.0858	118.0858	−0.4	C₅H₁₁NO₂	102.0542[M + H-CH₄]⁺, 100.0755[M + H-H₂O]⁺, 88.0389[M + H-2CH₃]⁺, 85.0283[M + H-CH₄-NH₃]⁺, 83.0482[M + H-NH₃-H₂O]⁺, 69.0336[M + H-NH₂-CH₃-H₂O]⁺, 58.0659[M + H-CH₃-HCOO]⁺	Organic acid	PRP	[9]
7	1.03	2-aminobutanoic acid	[M + Na]⁺	126.0540	126.0542	1.6	C₄H₉NO₂	88.0389[M + H-CH₄]⁺, 74.0243[M + H-C₂H₆]⁺, 69.0336[M + H-NH₃-H₂O]⁺, 58.0659[M + H-HCOOH]⁺	Organic acid	PRP	[9]
8	1.05	Hordenine	[M + H]⁺	166.1232	166.1237	3.0	C₁₀H₁₅NO	121.0338[M + H-NH(CH₃)₂]⁺	Other type	AFI	[7]
9	1.06	Pipecolic acid	[M + H]⁺	130.0861	130.0861	−0.2	C₆H₁₁NO₂	112.0756[M + H-H₂O]⁺, 94.0651[M + H-2H₂O]⁺	Organic acid	PRP	[10]
10	1.08	6H-Purin-6-one,2-amino-1,9-dihydro-	[M + H]⁺	152.0564	152.0564	−0.3	C₅H₅N₅O	174.0388[M + Na]⁺, 135.0290[M + H-NH₃]⁺, 122.0235[M + H-NHCH₃]⁺, 109.0504[M + H-NHCO]⁺	Alkaloid	PRP	[11]
11	1.19	Benzaldehyde	[M + H]⁺	107.0486	107.0486	−0.5	C₇H₆O	91.0540[M + H–O]⁺, 71.0385[M + H-HCOOH]⁺	Other type	PRP	[9]
12	1.29	Protocatechualdehyde	[M + H]⁺	139.0382	139.0381	−0.9	C₇H₆O₃	121.0288[M + H-H₂O]⁺, 109.0281[M + H-CH₂O]⁺	Other type	PRP	[12]
13	1.31	Vanillic acid	[M + H]⁺	169.0492	169.0492	−0.3	C₈H₈O₄	151.0383[M + H-H₂O]⁺, 123.0431[M + H-HCOOH]⁺, 109.0286[M + H-CH₃-COOH]⁺	Organic acid	CRP, AFI	[13, 14]
14	1.32	5-Hydroxymethyl furfual	[M + H]⁺	127.0388	127.0388	−0.2	C₆H₆O₃	109.0281[M + H-H₂O]⁺	Other type	AFI	[15]
15	1.40	p-Hydroxybenzaldehyde	[M + H]⁺	123.0433	123.0432	−0.9	C₇H₆O₂	95.0487[M + H–CO]⁺	Other type	BCT	[7]
16	1.42	4-Acetylbenzoic acid	[M + H]⁺	165.0542	165.0542	−0.4	C₉H₈O₃	147.0426[M + H-H₂O]⁺	Organic acid	PRP	[16]
17	1.74	N-Methyltyramine	[M + H]⁺	152.1064	152.1063	−0.7	C₉H₁₃NO	103.0542[M + H-NH₂CH₃-H₂O]⁺	Alkaloid	AFI	[7]
18	1.75	Phenylacetaldehyde	[M + H]⁺	121.0644	121.0643	−0.5	C₈H₈O	103.0542[M + H-H₂O]⁺	Other type	PRP	[9]
19	2.43	Methyl 2-(methylamino) benzoate	[M + H]⁺	166.0866	166.0865	−0.9	C₉H₁₁NO₂	137.0598[M + H-NHCH₂]⁺, 136.0760[M + H-OCH₂]⁺, 77.0389[M + H-NHCH₂-COOH-CH₃]⁺	Other type	CRP	[14]
20	4.37	Tryptophan	[M + H]⁺	205.0950	205.0944	−2.7	C₁₁H₁₂N₂O₂	188.0707[M + H-NH₃]⁺, 143.0716[M + H-NH₂-HCOOH]⁺, 142.0644[M + H-NH₃-HCOOH]⁺, 118.0649[C₈H₈N]⁺	Alkaloid	GRR	[12]
21	4.67	Fabiatrin	[M + H]⁺	487.1542	487.1548	1.2	C₂₁H₂₆O₁₃	341.0863[M + H-C₆H₉O₄]⁺, 179.0347[C₉H₇O₄]⁺	Coumarin	AFI	[17]
22	5.74	Luteolin 7-O-rutinoside	[M + H]⁺	595.1664	595.1664	0.2	C₂₇H₃₀O₁₅	617.1539[M + Na]⁺, 577.1539[M + H-H₂O]⁺, 287.0556[M + H-Rha-Glc]⁺, 153.0187[C₇H₅O₄]⁺	Flavonoid	AFI	[7, 17]
23	6.24	3-Hydroxy-4-methoxybenzoic acid	[M + H]⁺	169.0488	169.0486	−0.9	C₈H₈O₄	109.0280[M + H-CH₃-COOH]⁺, 105.0329[M + H-H₂O-HCOOH]⁺	Organic acid	CRP	[14]
24	6.60	Diosmetin 6,8-di-C-glucoside	[M-H]⁻	623.1612	623.1612	0.2	C₂₈H₃₂O₁₆	533.1279[M-H-C₃H₆O₃]⁻, 503.1146[M-H-C₄H₈O₄]⁻, 443.1023[M-H-2C₃H₆O₃]⁻, 413.0898[M-H-2C₃H₆O₃-CO]⁻, 383.0763[M-H-2C₄H₈O₄]⁻, 353.0666[M-H-2C₄H₈O₄-CO]⁻	Flavonoid	CRP	[7]
25	7.14	Choerospondin	[M-H]⁻	433.1116	433.1121	1.2	C₂₁H₂₂O₁₀	271.0603[M-H-Glc]⁻, 151.0024[C₈H₇O₃]⁻	Flavonoid	GRR	[7]
26	7.19	Shaftoside	[M + H]⁺	565.1557	565.1563	1.1	C₂₆H₂₈O₁₄	587.1317[M + Na]⁺, 547.1441[M + H-H₂O]⁺	Flavonoid	GRR	[18]
27	8.12	Liquirtigenin	[M + H]⁺	257.0801	257.0799	−0.9	C₁₅H₁₂O₄	239.0682[M + H-H₂O]⁺, 137.0225[C₇H₅O₃]⁺, 119.0487[M + H-C₇H₆O₃]⁺	Flavonoid	GRR	[19,20,21]
28^a	8.38	Quercetin	[M + H]⁺	303.0487	303.0482	−1.7	C₁₅H₁₀O₇	285.0350[M + H-H₂O]⁺, 257.0358[M + H-H₂O-CO]⁺, 229.0487[M + H-C₂H₂O₃]⁺, 181.0623[C₁₃H₉O]⁺, 153.0175[C₇H₅O₄]⁺, 123.0444[C₇H₇O₂]⁺, 109.0247[C₆H₅O₂]⁺	Flavonoid	AFI, GRR	[19]
29	8.69	Naringenin-7-O-triglycoside	[M + H]⁺	743.2399	743.2394	−0.7	C₃₃H₄₂O₁₉	595.1651[M + H-Rha]⁻	Flavonoid	AFI	[22]
30	9.39	Apiin	[M + H]⁺	565.1546	565.1539	−1.3	C₂₆H₂₈O₁₄	433.1147[M + H-Api]⁺, 271.0613[M + H-Api-Glc]⁺	Flavonoid	AFI	[23]
31^a	9.41	Eriocitrin	[M + H]⁺	597.1819	597.1825	1.0	C₂₇H₃₂O₁₅	619.1599[M + Na]⁺, 579.1702[M + H-H₂O]⁺, 451.1284[M + H-Rha]⁺, 435.1239[M + H-Rha-O]⁺, 433.1154[M + H-Rha-H₂O]⁺, 289.0699[M + H-Rha-Glc]⁺, 163.0366[M + H-Rha-Glc-C₆H₅O₃]⁺, 153.0176[M + H-Rha-Glc-C₈H₇O₂]⁺	Flavonoid	AFI	[7, 24]
32	9.57	Naringenin-7-O-glucoside	[M + H]⁺	435.1290	435.1293	0.7	C₂₁H₂₂O₁₀	273.0748[M + H-Glc]⁺	Flavonoid	AFI	[7, 22]
33	9.83	Eriodictyol	[M + H]⁺	289.0703	289.0702	−0.4	C₁₅H₁₂O₆	179.0313[M + H-C₆H₆O₂]⁺, 153.0174[M + H-C₈H₈O₂]⁺, 135.0438[M + H-C₇H₆O₄]⁺	Flavonoid	AFI, GRR	[7]
34	10.36	Orientin	[M + H]⁺	449.1070	449.1062	−1.7	C₂₁H₂₀O₁₁	359.0851 [M + H-C₃H₆O₃]⁺	Flavonoid	AFI	[7]
35	10.54	Isonaringin	[M + H]⁺	581.1866	581.1866	0.1	C₂₇H₃₂O₁₄	603.1652[M + Na]⁺, 435.1255[M + H-Rha]⁺, 419.1331[M + H-Rha-O]⁺, 273.0754[M + H-Rha-Glc]⁺	Flavonoid	CRP, AFI	[23]
36	10.79	Ferulic acid	[M + H]⁺	195.0558	195.0554	−1.9	C₁₀H₁₀O₄	177.0534[M + H-H₂O]⁺, 134.0367[M + H-HCOOH-CH₃]⁺, 117.0327[M + H-HCOOH-CH₂-H₂O]⁺	Organic acid	CRP, AFI	[13]
37^a	11.18	Liquiritin	[M + H] +	419.1329	419.1323	−1.4	C₂₁H₂₂O₉	257.0794[M + H-Glc]⁺, 239.0702[M + H-Glc-O]⁺	Flavonoid	GRR	[2, 3, 7, 21, 25]
38	11.32	Rutin	[M + H]⁺	611.1595	611.1577	−3.0	C₂₇H₃₀O₁₆	303.0483[M + H-Rha-Glc]⁺, 285.0350[M + H-Rha-Glc-H₂O]⁺	Flavonoid	AFI	[7, 22]
39	11.52	Pinocembrin	[M + H]⁺	257.0803	257.0802	−0.6	C₁₅H₁₂O₄	239.0699[M + H-H₂O]⁺, 221.0560[M + H-2H₂O]⁺, 211.0740[M + H-H₂O-CO]⁺	Flavonoid	GRR	[12]
40^a	11.88	Naringenin	[M + H]⁺	273.0750	273.0747	−1.1	C₁₅H₁₂O₅	255.0655[M + H-H₂O]⁺, 179.0327[C₉H₇O₄]⁺, 153.0178[M + H-C₈H₈O]⁺, 121.0509[C₄H₉O₄]⁺, 85.0281[C₄H₅O₂]⁺	Flavonoid	AFI, GRR	[7, 19]
41	11.95	Isosakuranetin-5,7-di-O-glucoside	[M + H]⁺	611.1976	611.1976	0.0	C₂₈H₃₄O₁₅	449.1563[M + H-Glc]⁺, 287.0624[M + H-2Glc]⁺, 153.0191[C₁₉H₂₇O₁₄-2Glc]⁺	Flavonoid	AFI, CRP	[7]
42	12.47	Kaempferol 3-O-rhamnoside	[M + H]⁺	433.1128	433.1128	−0.2	C₂₁H₂₀O₁₀	415.0970[M + H-H₂O]⁺, 397.0860[M + H-2H₂O]⁺, 285.0375[M + H-Rha]⁺, 153.0176[C₇H₅O₄]⁺	Flavonoid	AFI	[26]
43	12.72	Saponarin	[M + H]⁺	595.1651	595.1643	−1.4	C₂₇H₃₀O₁₅	433.1088[M + H-Glc]⁺, 313.1809[M + H-Glc-C₄H₈O₄]⁺	Flavonoid	GRR	[7]
44	12.73	Luteolin	[M + H]⁺	287.0540	287.0536	−1.4	C₁₅H₁₀O₆	151.0384[C₈H₇O₃]⁺, 107.0486[C₇H₇O]⁺	Flavonoid	AFI	[12]
45	12.75	Diosmetin-7-O-glucoside	[M + H]⁺	464.1222	463.1211	−2.4	C₂₂H₂₂O₁₁	300.0615[M + H-Glc]⁺, 285.0722[M + H-Glc-O]⁺, 271.0577[M + H-Glc-CO]⁺	Flavonoid	AFI	[23]
46	13.18	Meranzin	[M + H]⁺	261.1112	261.1112	−0.1	C₁₅H₁₆O₄	283.0926[M + Na]⁺, 243.0992[M + H-H₂O]⁺, 189.0536[M + H-C₄H₈O]⁺, 131.0483[M + H-C₄H₈O-CO-CH₂O]⁺, 103.0537[M + H-C₄H₈O-CH₂O-2CO]⁺	Coumarin	AFI	[7, 27]
47^a	13.81	Naringin	[M + H]⁺	581.1863	581.1863	−0.2	C₂₇H₃₂O₁₄	603.1649[M + Na]⁺, 435.1256[M + H-Rha]⁺, 419.1319[M + H-Rha-O]⁺, 401.1165[M + H-Rha-O-H₂O]⁺, 383.1111[M + H-Rha-O-2H₂O]⁺, 273.0751[M + H-Rha-Glc]⁺, 153.0176[M + H-Rha-Glc-C₈H₈O]⁺, 121.0277[M + H-Rha-Glc-C₈H₇O₃]⁺	Flavonoid	CRP, AFI	[4, 7, 17]
48	13.82	Nomilin	[M + H]⁺	515.2292	515.2281	−2.1	C₂₈H₃₄O₉	469.6160[M + H-CH₂O₂]⁺, 411.3182[M + H-CH₂O₂-2CH₃-H₂O]⁺	Triterpenoid	AFI, CRP	[14, 17]
49	13.86	Nominin-17-b-D-glucoside	[M-H]⁻	693.2770	693.2758	−1.7	C₃₄H₄₆O₁₅	529.2567[M-H-Glc]⁻	Triterpenoid	AFI	[22]
50^a	14.31	Hesperidin	[M + H]⁺	611.1976	611.1976	0.0	C₂₈H₃₄O₁₅	633.1789[M + Na]⁺, 465.1396[M + H-Rha]⁺, 449.1448[M + H-Rha-O]⁺, 431.1339[M + H-Rha-O-H₂O]⁺, 303.0871[M + H-Rha-Glc]⁺	Flavonoid	CRP, AFI	[4, 7, 17, 28]
51	14.37	Meranzin hydrate	[M + H]⁺	279.1219	279.1216	−1.1	C₁₅H₁₈O₅	261.1111[M + H-H₂O]⁺, 189.0534[M + H-H₂O-2CH₃-CH₂-CO]⁺	Coumarin	AFI	[13]
52	14.40	Apigenin-7-O-rutinoside	[M + H]⁺	579.1705	579.1700	−0.8	C₂₇H₃₀O₁₄	417.1163[M + H-Rha-O]⁺, 271.0578[M + H-Rha-Glc]⁺	Flavonoid	AFI	[13]
53	14.41	3,4-Dihydroxybenzoic acid	[M + H]⁺	154.0218	154.0210	−5.0	C₇H₆O₄	177.0174[M + Na]⁺, 111.0438[M + H-CO₂]⁺, 93.0280[M + H-CO₂-H₂O]⁺	Organic acid	PRP, GRR, ZRR	[29]
54	14.42	Gallic acid	[M + H]⁺	171.0276	171.0273	−1.5	C₇H₆O₅	153.0181[M + H-H₂O]⁺, 135.0067[M + H-2H₂O]⁺, 125.0227[M + H-HCOOH]⁺, 107.0123[M + H-HCOOH-H₂O]⁺	Organic acid	PRP, AFI	[30]
55	14.43	Chrysin	[M + H]⁺	255.0643	255.0640	−1.2	C₁₅H₁₀O₄	153.0181[C₇H₅O₄]⁺	Flavonoid	ZRR	[26]
56	14.58	NomiliniCacid	[M + H]⁺	533.2387	533.2373	−2.6	C₂₈H₃₆O₁₀	515.2302[C₂₈H₃₅O₉]⁺, 473.2173[C₂₆H₃₃O₈]⁺, 455.2074[C₂₆H₃₁O₇]⁺, 429.2148[C₂₁H₃₃O₉]⁺, 393.2117[C₁₈H₃₃O₉]⁺, 379.2070[C₂₃H₂₉O₄]⁺	Triterpenoid	AFI	[17]
57	14.66	Diosmin	[M + H]⁺	609.1816	609.1818	0.4	C₂₈H₃₂O₁₅	463.1166[M + H-Rha]⁺, 301.0692[M + H-Rha-Glc]⁺, 268.0460[M + H-Rha-Glc-CH₃]⁺	Flavonoid	AFI	[7]
58^a	14.94	Hesperetin	[M + H]⁺	303.0861	303.0859	−0.5	C₁₆H₁₄O₆	327.0845[M + Na]⁺, 153.0178[C₇H₅O₄]⁺, 149.0604[C₉H₁₁O₂-2H]⁺, 117.0331[C₉H₁₁O₂-2H-CH₂-H₂O]⁺,	Flavonoid	AFI, GRR	[7, 17, 19, 24]
59	14.94	Didymin	[M + H]⁺	595.1953	595.1961	1.3	C₂₈H₃₄O₁₄	617.1854[M + Na]⁺, 559.1815[M + H-2H₂O]⁺, 447.1259[M + H-Rha]⁺, 431.1330[M + H-Rha-O]⁺, 413.1200[M + H-H₂O-Rha-O]⁺, 285.0738[M + H-Rha-Glc]⁺	Flavonoid	AFI	[13]
60^a	14.98	Neohesperidin	[M + H]⁺	611.1815	611.1819	0.7	C₂₈H₃₄O₁₅	633.1784[M + Na]⁺, 593.1866[M + H-H₂O]⁺, 465.1396[M + H-Rha]⁺, 449.1448[M + H-Rha-O]⁺, 431.1339[M + H-Rha-O-H₂O]⁺, 303.0868[M + H-Rha-Glc]⁺, 285.0761[M + H-Rha-Glc-H₂O]⁺	Flavonoid	CRP, AFI	[4, 7, 17]
61	14.99	Byakangelicol	[M + H]⁺	317.1025	317.1023	−0.6	C₁₇H₁₆O₆	273.0771[C₁₅H₁₃O₅]⁺, 233.0115[C₁₁H₅O₆]⁺, 231.0403[C₁₆H₇O₂]⁺	Coumarin	GRR	[19]
62	15.30	Isorhamnetin	[M + H]⁺	317.0644	317.0639	−1.6	C₁₆H₁₂O₇	302.0407[M + H-CH₃]⁺	Flavonoid	AFI	[13]
63	15.62	Esculetin	[M + H]⁺	179.0333	179.0332	−0.6	C₉H₆O₄	151.0384[M + H–CO]⁺, 133.0280[M + H-HCOOH]⁺, 123.0437[M + H-C₂O₂]⁺, 105.0329[M + H-C₂O₂-H₂O]⁺	Coumarin	AFI	[17, 26]
64	15.62	Umbelliferone	[M + H]⁺	163.0376	163.0373	−1.7	C₉H₆O₃	135.0433[M + H–CO]⁺, 119.0484[M + H-CO₂]⁺	Coumarin	AFI	[7]
65	15.62	Kaempferol	[M + H]⁺	287.0545	287.0543	−0.7	C₁₅H₁₀O₆	241.0471[M + H-CH₂O₂]⁺, 91.0540[M + H-C₈H₄O₆]⁺	Flavonoid	AFI	[26]
66	15.62	Trifolirhizin	[M + H]⁺	447.1281	447.1277	−0.9	C₂₂H₂₂O₁₀	429.1167[M + H-H₂O]⁺, 411.1043[M + H-2H₂O]⁺, 393.0968[M + H-3H₂O]⁺, 285.0751[M + H-Glc]⁺	Flavonoid	GRR	[12]
67	15.62	Diethyl oxalate	[M + H]⁺	147.0653	147.0653	0.1	C₆H₁₀O₄	129.0542[M + H-H₂O]⁺, 83.0126[M + H-H₂O-C₂H₅O]⁺, 68.9972[M + H-H₂O-C₂H₅O-CH₃]⁺	Other type	PRP	[9]
68	15.62	Phthalic anhydride	[M + H]⁺	149.0228	149.0227	−0.6	C₈H₄O₃	133.0280[M + H–O]⁺, 121.0279[M + H–CO]⁺, 105.0329[M-COOH]⁺	Other type	PRP	[11, 16]
69	15.62	2-Methoxy-4-vinylphenol	[M + H]⁺	151.0747	151.0746	−0.6	C₉H₁₀O₂	136.0490[M + H-CH₃]⁺, 123.0437[M + H-C₂H₄]⁺, 119.0484[M + H-CH₃-O]⁺, 117.0332[M + H-H₂O-CH₄]⁺	Other type	CRP	[14]
70	15.65	Luteone	[M + H]⁺	355.1564	355.1557	−1.9	C₂₀H₁₈O₆	311.0527[M + H-C₃H₈]⁺, 221.0424[C₁₁H₉O₅]⁺	Flavonoid	GRR	[7]
71	16.11	Isosakuranin	[M + H]⁺	449.1461	449.1448	−2.9	C₂₂H₂₄O₁₀	419.1358[M + H-CH₂O]⁺, 287.0924[M + H-Glc]⁺, 257.0879[M + H-Glc-CH₂O]⁺, 153.0178[C₁₄H₂₀O₈-Glc]⁺	Flavonoid	AFI	[7]
72	16.25	Neoliquiritin	[M + H]⁺	419.1329	419.1323	−1.4	C₂₁H₂₂O₉	257.0794[M + H-Glc]⁺, 239.0702[M + H-Glc-O]⁺	Flavonoid	GRR	[7]
73	16.38	Obacunone	[M + H]⁺	455.2057	455.2051	−1.4	C₂₆H₃₀O₇	437.1988[M + H-H₂O]⁺, 411.2189[M + H-CO₂]⁺, 409.2007[M + H–CO-H₂O]⁺, 393.2066[M + H-CO₂-H₂O]⁺, 391.1943[M + H–CO-2H₂O]⁺, 349.1822[M + H–CO-2H₂O-C₃H₆]⁺	Triterpenoid	AFI	[7, 17]
74	16.38	Deacetyl nomilin	[M + H]⁺	473.2159	473.2150	−2.0	C₂₆H₃₂O₈	455.2053[M + H-H₂O]⁺	Triterpenoid	AFI	[7]
75	16.38	Isosarotanoside	[M-H]⁻	563.1747	563.1765	3.2	C₂₇H₃₂O₁₃	609.1808[M + COOH]⁻, 255.0137[M + H-Rha-Glc]⁻	Flavonoid	CRP	[7]
76	16.71	Isoliquiritin apioside	[M + H]⁺	551.1784	551.1765	−3.4	C₂₆H₃₀O₁₃	257.8640[M + H-Api-Glc]⁺, 147.2897[C₇H₁₅O₃]⁺, 137.0648[C₈H₉O₂]⁺	Flavonoid	PRP, GRR	[7]
77	16.78	Licochalcone B	[M + H]⁺	287.0919	287.0921	0.7	C₁₆H₁₄O₅	271.0863[C₁₂H₁₅O₇]⁺	Flavonoid	GRR	[31]
78	16.79	Ononin	[M + H]⁺	431.1327	431. 1319	−1.8	C₂₂H₂₂O₉	476.2991[M-H + HCOOH]⁺, 269.0797 [M + H-Glc]⁺	Flavonoid	GRR	[7, 20]
79	18.50	Uralsaponin N	[M-H]⁻	837.3916	837.3909	−0.8	C₄₂H₆₂O₁₇	661.3422[M-H-GluA]⁻, 485.3456[M-H-2GluA]⁻, 467.2256[M-H-2GluA-H₂O]⁻, 449.3533[M-H-2GluA-2H₂O]⁻	Triterpenoid	GRR	[7]
80	18.56	Calycosin	[M + H]⁺	285.0746	285.0741	−1.7	C₁₆H₁₂O₅	213.0538[M + H-2CO-CH₄]⁺	Flavonoid	GRR	[7]
81	18.85	CitrusinIII	[M + H]⁺	728.3994	728.3983	−1.5	C₃₆H₅₃N₇O₉	700.3988[M + H–CO]⁺	Alkaloid	CRP	[7]
82	19.10	Liquiritin apioside	[M + H]⁺	551.1742	551.1721	−3.8	C₂₆H₃₀O₁₃	389.1217[M + H-Glc]⁺, 257.0789[M + H-Glc-Api]⁺	Flavonoid	GRR, PRP	[7, 20]
83	19.14	Uralsaponin F	[M + H]⁺	897.4120	897.4120	−0.1	C₄₄H₆₄O₁₉	545.3578[M + H-2GluA]⁺, 527.3006[M + H-2GluA-H₂O]⁺, 497.3338[M + H-2GluA-H₂O-CH₂O]⁺	Triterpenoid	GRR	[7]
84	19.27	Glycycoumarin	[M + H]⁺	369.1325	369.1320	−1.3	C₂₁H₂₀O₆	353.1026[M + H-CH₄]⁺, 315.0827[M + H-C₄H₆]⁺, 299.0888[M + H-C₄H₆-O]⁺, 285.0753[M + H-C₄H₆-CH₂O]⁺	Coumarin	GRR	[13]
85	19.36	Glycyrrhetinic acid	[M + H]⁺	855.4024	855.4014	−1.2	C₄₂H₆₂O₁₈	679.3223[M + H-GluA]⁺, 503.3375[M + H-2GluA]⁺, 467.3128[M + H-2GluA-2H₂O]⁺	Triterpenoid	GRR	[20]
86	19.62	Lupiwighteone	[M + H]⁺	339.1218	339.1214	−1.3	C₂₀H₁₈O₅	283.0579[M + H-C₄H₈]⁺, 255.0645[M + H-C₄H₈-CO]⁺, 165.0170[C₁₂H₁₃O₄-C₄H₈]⁺, 135.0436[C₈H₇O₂]⁺	Flavonoid	GRR	[7]
87	19.64	Melitidin	[M + H]⁺	725.2293	725.2293	−0.1	C₃₃H₄₀O₁₈	419.1338[C₂₁H₂₃O₉]⁺, 404.1101[C₂₁H₂₃O₉-CH₃]⁺, 389.0856[C₂₁H₂₃O₉-2CH₃]⁺	Flavonoid	AFI, CRP	[7]
88	19.70	Poncirin	[M + H]⁺	595.2019	595.2015	−0.6	C₂₈H₃₄O₁₄	617.1823[M + Na]⁺, 449.1407[M + H-Rha]⁺, 433.1495[M + H-Rha-O]⁺, 397.1251[M + H-Rha-O-2H₂O]⁺, 287.0908[M + H-Rha-Glc]⁺	Flavonoid	AFI	[4, 7]
89	19.94	Licorice saponin A3	[M + H]⁺	985.4567	985.4550	−1.7	C₄₈H₇₂O₂₁	809.42744[M + H-GluA]⁺, 647.3741[M + H-GluA-Glc]⁺, 633.3950[M + H-2GluA]⁺, 615.3851[M + H-2GluA-H₂O]⁺, 471.3466[M + H-2GluA-Glc]⁺, 453.3351[M + H-2GluA-Glc-H₂O]⁺, 435.3224[M + H-2GluA-Glc-2H₂O]⁺, 407.3284[M + H-2GluA-Glc-2H₂O-CO]⁺	Triterpenoid	GRR	[9]
90	20.06	Riparin Ι	[M + H]⁺	256.1349	256.1338	−4.3	C₁₆H₁₇NO₂	121.1011[C₈H₉O]⁺, 105.0213[C₇H₅O]⁺	Alkaloid	AFI	[7]
91	20.10	22β-Acetoxyl-glycyrrhizin	[M + H]⁺	881.4181	881.4171	−1.1	C₄₄H₆₄O₁₈	529.3373[M + H-2GluA]⁺, 511.3416[M + H-2GluA-H₂O]⁺, 451.3151[M + H-2GluA-H₂O-CH₃COOH]⁺, 433.3008[M + H-2GluA-2H₂O-CH₃COOH]⁺	Triterpenoid	GRR	[7]
92	20.23	Isosakuranetin	[M + H]⁺	287.0912	287.0912	0.2	C₁₆H₁₄O₅	153.0186[C₇H₅O₄]⁺, 133.0795[C₉H₉O]⁺	Flavonoid	CRP	[14]
93	21.15	5,7,8,4'-Tetramethoxyflavone	[M + H]⁺	343.1182	343.1176	−1.7	C₁₉H₁₈O₆	313.0709[M + H-2CH₂]⁺	Flavonoid	AFI	[22]
94	21.54	4′-O-methyl glabridin	[M + H]⁺	355.1513	355.1498	−4.2	C₂₁H₂₂O₅	287.0994[M + H-C₅H₈]⁺, 283.0584[M + H-C₄H₉-CH₃]⁺, 272.0595[M + H-C₅H₈-CH₃]⁺	Flavonoid	GRR	[12]
95	21.55	M-Cymene	[M + H]⁺	135.1160	135.1159	−0.9	C₁₀H₁₄	91.0540[M + H-C₃H₈]⁺, 77.0386[M + H-C₃H₈-CH₃]⁺	Other type	ZRR	[26]
96^a	21.79	Glycyrrhizic acid	[M + H]⁺	823.4116	823.4116	0.0	C₄₂H₆₂O₁₆	845.3920[M + Na]⁺, 647.3798[M + H-GluA]⁺, 471.3476[M + H-2GluA]⁺, 453.3371[M + H-2GluA-H₂O]⁺, 435.3252[M + H-2GluA-2H₂O]⁺, 407.3302[M + H-2GluA-2H₂O-CO]⁺	Triterpenoid	GRR	[4, 17]
97	21.82	Licorice saponin G2	[M + H]⁺	839.4058	839.4048	−1.2	C₄₂H₆₂O₁₇	663.3780[M + H-GluA]⁺, 487.3412[M + H-2GluA]⁺, 469.3293[M + H-2GluA-H₂O]⁺, 451.3190[M + H-2GluA-2H₂O]⁺, 439.3181[M + H-2GluA-CH₂O]⁺	Triterpenoid	GRR	[7, 21]
98	22.20	Nobiletin	[M + H]⁺	403.1386	403.1385	−0.3	C₂₁H₂₂O₈	425.1197[M + Na]⁺, 387.1055[M + H-CH₄]⁺, 373.0916[M + H-2CH₃]⁺, 358.0673[M + H-3CH₃]⁺, 345.0952[M + H-2CH₃-CO]⁺, 327.0851[M + H-2CH₃-H₂O-CO]⁺, 321.0698[M + H-4CH₂-CO₂]⁺, 211.0225[C₁₁H₁₃O₆-2CH₃]⁺, 183.0289[C₁₁H₁₃O₆-2CH₃-CO]⁺, 163.0744[C₁₀H₁₁O₂]⁺	Flavonoid	CRP	[7, 17]
99	22.38	Uralsaponin C	[M + H]⁺	824.4180	824.4139	−5.0	C₄₂H₆₄O₁₆	663.3671[M + H-GluA]⁺, 473.3512[M + H-2GluA]⁺, 457.3387[M + H-2GluA-O]⁺, 455.3419[M + H-2GluA-H₂O]⁺	Triterpenoid	GRR	[12]
100	22.61	16-Dihydrosphingosine	[M + H]⁺	274.2746	274.2742	−1.5	C₁₆H₃₅NO₂	256.2610[M-H₂O]⁺	Other type	PRP	[16]
101	22.81	Limonin	[M + H]⁺	471.2004	471.1995	−1.9	C₂₆H₃₀O₈	493.1798[M + Na]⁺, 453.1877[M + H-H₂O]⁺, 435.1806[M + H-2H₂O]⁺, 425.1955[M + H–CO-H₂O]⁺	Triterpenoid	AFI	[7, 17]
102	23.20	Isosinensetin	[M + H]⁺	373.1278	373.1275	−0.7	C₂₀H₂₀O₇	357.1425[M + H-CH₄]⁺, 343.0747[M + H-2CH₃]⁺, 327.0475[M + H-2CH₃-CH₄]⁺, 315.0854[M + H-2CH₃-CO]⁺, 163.0746[C₁₀H₁₁O₂]⁺	Flavonoid	AFI	[7]
103^a	23.55	6-Gingerol	[M + H]⁺	295.0247	295.0240	−2.4	C₁₇H₂₆O₄	317.1713[M + Na]⁺, 277.1777[M + H-H₂O]⁺, 259.1012[M + H-2H₂O]⁺, 179.0635[C₁₀H₁₁O₃]⁺, 177.1246[C₁₁H₁₃O₂]⁺, 137.0593[C₈H₉O₂]⁺	Other type	ZRR	[13]
104	23.83	3,5,6,7,8,3′,4′-Heptamethoxyflavone	[M + H]⁺	433.1491	433.1489	−0.4	C₂₂H₂₄O₉	455.1309[M + Na]⁺, 417.1170[M + H-CH₄]⁺, 403.1018[M + H-2CH₃]⁺, 388.0773[M + H-3CH₃]⁺, 385.0914[M + H-2CH₃-H₂O]⁺, 373.0511[M + H-2CH₃-CO]⁺, 360.0847[M + H-3CH₃-CO]⁺	Flavonoid	CRP, AFI	[7, 22, 32]
105	24.18	5-Hydroxy-3,6,7,8,3',4'-Hexamethoxyflavone	[M + H]⁺	419.1329	419.1323	−1.4	C₂₁H₂₂O₉	441.1142[M + Na]⁺, 389.0858[M + H-CH₃]⁺, 371.0728[M + H-2CH₃-H₂O]⁺, 361.0907[M + H-2CH₃-CO]⁺, 346.0662[M + H-3CH₃-CO]⁺, 328.0563[M + H-3CH₃-CO-H₂O]⁺	Flavonoid	AFI	[23]
106^a	24.28	Tangeretin	[M + H]⁺	373.1276	373.1273	−0.9	C₂₀H₂₀O₇	395.1074[M + Na]⁺, 357.0945[M + H-CH₄]⁺, 343.0806[M + H-2CH₃]⁺, 328.0563[M + H-3CH₃]⁺, 315.0847[M + H-2CH₃-CO]⁺, 300.0619[M + H-3CH₃-CO]⁺, 299.0536[M + H-4CH₂-H₂O]⁺, 297.0748[M + H-2CH₃-CH₄-H₂O]⁺, 211.0318[C₁₁H₁₃O₆-2CH₃]⁺, 183.0288[C₁₁H₁₃O₆-2CH₃-CO]⁺	Flavonoid	CRP	[7, 17]
107	25.37	Ethylparaben	[M + H]⁺	167.0695	167.0694	−0.8	C₉H₁₀O₃	149.0595[M + H-H₂O]⁺, 121.0271[M-CH₂CH₃-H₂O]⁺, 95.0487[M-COOC₂H₅]⁺, 77.0384[M-COOC₂H₅-H₂O]⁺	Other type	PRP	[9]

PRP Pinelliae Rhizoma Praeparatum, AFI Aurantii Fructus Immaturus, CRP Citri Reticulatae Pericarpium, BCT Bambusae Caulis in Taenias, GRR Glycyrrhizae Radix et Rhizoma, ZRR Zingiberis Rhizoma Recens
^aIdentified by comparison with reference standards

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