Table 1.

Identification of chemical constituents of GDD by UPLC-Q-TOF-MS^E.

No.	tR (min)	Idenfitication	Neutral mass (Da)	Formular	Observed neutral mass (Da)	Experimental mass (m/z)	Error (ppm)	MS and MSE data (+ or −) (m/z)	Source
1	0.98	Gallic acid-O-glc	332.0743	C13H16O10	332.0743	331.0669	-0.5	331.0669[M−H]− 169.0141[M−H-Glc]−	a
2	1.05	Gallic acid	170.0215	C7H6O5	170.0214	169.0141	-0.8	169.0141[M−H]− 125.0244[M−H-CO2]−	a
3	1.39	Progallin A	198.0528	C9H10O5	198.0528	197.0455	-0.7	197.0455[M−H]− 124.0455[M−H-2CH2-COOH]−	a
4	1.50	(+)-Catechin-5-O-β-D-glc	452.1319	C21H24O11	452.1318	451.1245	-0.7	451.1245[M−H]− 289.0717[M−H-Glc]−	a
5	1.71	Procyanidin B	578.1424	C30H26O12	578.1432	577.1359	1.4	577.1359[M−H]− 425.0873[M–H-C7H4O4]− 407.0763[M–H-C7H4O4-H2O]− 289.0712[M−H-catechin]−	a
6	2.71	Chlorogenic acid	354.0951	C16H18O9	354.0962	353.0889	3.1	353.0889[M−H]− 191.0899[M-C9H6O3]−	b,d
7	2.82	(-)-Epicatechin	290.0790	C15H14O6	290.0797	289.0724	2.3	289.0724[M−H]− 245.0821[M−H-CO2]−	a
8	3.16	Isocorydine	341.1627	C20H23NO4	341.1628	342.1707	0.1	342.1707[M+H]+ 296.1132[M+H-CH3-CH3O]+	b
9	3.19	Procyanidin B-O-gallate	730.1534	C37H30O16	730.1544	729.1471	1.3	729.1471[M−H]− 577.1350[M−H-gallate]−	a
10	3.20	Magnoflorine	342.1705	C20H24NO4	342.1730	342.1701	-1.2	342.1701[M]+ 297.1123[M-(CH3)2NH]+ 282.0876[M-(CH3)2NH-CH3]+ 265.0861[M-(CH3)2NH-CH3OH]+ 237.0908[M-(CH3)2NH-CH3OH-CO]+	b
11	3.42	Isoboldine	327.1471	C19H21NO4	327.1479	328.1552	2.7	328.1552[M+H]+ 297.1123[M+H-CH3O]+	b
12	3.79	Isovitexin	432.1056	C21H20O10	432.1065	477.1047	1.8	477.1047[M+HCOO]− 431.0982[M−H]− 311.0567[M−H-CO2-C3H8O2]−	d
13	4.75	Tetradehydroscoulerine	322.1079	C19H16NO4	322.1055	322.1052	-6.6	322.1052[M]+ 307.0839[M-CH3]+ 279.0511[M-CH3-CO]+	b
14	4.79	Procyanidin B-5,3,3'-di-O -gallate	882.1643	C44H34O20	882.1685	881.1612	4.8	881.1612[M−H]− 729.1471[M−H-gallate]− 711.0735[M−H-gallate-H2O]− 559.1341[M−H-2gallate-H2O]−	a
15	4.86	Emodin-8-O-β-D-glc	432.1056	C21H20O10	432.1065	431.0992	1.9	431.0992[M−H]− 269.0461[M−H-Glc]− 241.0493[M−H-Glc-CO]− 225.0554[M−H-Glc-CO-O]−	a
16	4.88	Rutin	610.1534	C27H30O16	610.1555	609.1483	3.6	609.1483[M−H]− 463.0815[M−H-Rha]− 301.0487[M−H-Rha-Glc]−	a,d
17	5.09	Rhein-1-O-β-D-glc	446.0849	C21H18O11	446.0860	445.0787	2.4	445.0787[M−H]− 283.0256[M−H-Glc]− 239.0356[M−H-Glc-CO2]− 211.0403[M−H-Glc-CO2-CO]−	a
18	5.11	Isolindleyin or lindleyin	478.1475	C23H26O11	478.1483	477.1410	1.7	477.1410[M−H]− 313.0552[M−H-C10H12O2]− 169.0145[M−H-C16H20O6]−	d
19	5.14	(+)-Catechin-3-O-gallate	442.0900	C22H18O10	442.0910	441.0838	2.4	441.0838[M−H]− 289.0722[M−H-C7H4O4]− 165.1245[M−H-C14H12O6]−	a
20	5.20	Ferulic acid-O-β-D-glc	356.1107	C16H20O9	356.1113	355.1040	1.5	355.1040[M−H]− 193.1033[M−H-Glc]−	d
21	5.25	Isoquercitrin	464.0955	C21H20O12	464.0972	463.0899	3.7	463.0899[M−H]− 301.0038[M−H-C6H10O5]−	d
22	5.45	Isolindleyin or lindleyin	478.1475	C23H26O11	478.1482	477.1408	1.6	477.1408[M−H]− 313.0551[M−H-C10H12O2]− 169.0144[M−H-C16H20O6]−	a
23	5.61	Kaempferol-3-O-rutinoside	594.1585	C27H30O15	594.1599	593.1521	1.6	593.1521[M−H]− 447.1591[M−H-Rha]− 285.0832[M−H-Rha-Glc]−	d
24	5.65	Resveratrol-4'-O-β-D-(2''-O-galloyl)-glc	542.1424	C27H26O12	542.1431	541.1333	1.2	541.1333[M−H]− 313.0555[M−H-Res-H2O]−	a
25	5.70	Sennoside C or D	848.2164	C42H40O19	848.2177	847.2104	1.5	847.2104[M−H]− 685.1557[M−H-Glc]−	a
26	5.89	Tetrahydropalmatine	355.1784	C21H25NO4	355.1792	356.1865	2.4	356.1865[M+H]+ 192.1019[M+H-C10H12O2]+	b
27	6.24	Sennoside A or B	862.1956	C42H38O20	862.1981	861.1908	2.8	861.1908[M−H]− 699.1358[M−H-Glc]− 655.1880[M−H-Glc-CO2]− 386.1002[M−H-Glc-CO2-C15H9O5]−	a
28	6.36	Homoorientin	448.1006	C21H20O11	448.1000	447.0927	-1.2	447.0927[M−H]−	d
29	6.52	Thalifendine	322.1079	C19H16NO4	322.1069	322.1082	-0.4	322.1082[M]+ 279.0889[M-CH3-CO]+	b
30	6.94	Hesperetin-5-O-glc	464.1319	C22H24O11	464.1313	463.1240	1.5	463.1240[M−H]− 301.1131[M−H-Glc]−	d
31	7.01	Coptisine	320.0923	C19H14NO4	320.0921	320.0921	0.6	320.0921[M]+ 292.0970[M-CO]+	b
32	7.08	Rhein-8-O-β-D-(6"-O-acetyl)-glc	488.0955	C23H20O12	488.0949	487.0876	1.5	487.0876[M−H]− 283.0246[M−H-acetyl-Glc]− 239.0347[M−H-acetyl-Glc-CO2]−	a
33	7.15	Jatrorrhizine	338.1392	C20H20NO4	338.1384	338.1384	2.4	338.1384[M]+ 322.0997[M-CH3-H]+ 308.1309[M-2CH3]+	b
34	7.35	Epiberberine	336.1236	C20H18NO4	336.1250	336.1250	-4.2	336.1250[M]+ 320.0935[M-CH3-H]+ 292.1314[M-CH3-H-CO]+	b
35	7.47	Aloe emodin-8-O-β-D-glc	432.1056	C21H20O10	432.1068	431.0992	0.8	431.0992[M−H]− 269.0385[M−H-Glc]− 225.0562[M−H-Glc-CO2]−	a
36	7.48	Tetrahydroberberine	339.1471	C20H21NO4	339.1466	340.1544	-1.4	340.1544[M+H]+ 176.0705[M+H-C10H12O2]+	b
37g	7.72	Notoginsenoside R1	932.5345	C47H80O18	932.5372	977.5354	2.8	977.5354[M+HCOO]− 931.5297[M−H]− 799.4856[M−H-Xyl]− 637.4314[M−H-Xyl-Glc]− 475.3782[M−H-Xyl-2Glc]−	f
38	8.09	Worenine	334.1079	C20H16NO4	334.1080	334.1080	-0.3	334.1080[M]+ 320.1093[M-CH2]+ 318.1092[M-CH2-2H]+ 292.0969[M-CH2-CO]+	b
39g	8.46	Berberine	336.1236	C20H18NO4	336.1230	336.1231	1.8	336.1231[M]+ 321.0983[M-CH3]+ 320.0918[M-CH3-H]+ 306.0763[M-2CH3]+ 292.0969[M-CH3-H-CO]+ 278.0813[M-2CH3-CO]+	b
40	8.51	Palmatine	352.1549	C21H22NO4	352.1543	352.1538	-1.7	352.1538[M]+ 337.1430[M-CH3]+ 336.0983[M-CH3-H]+ 322.1068 [M-2CH3]+ 308.1275 [M-CH3-H-CO]+	b
41	8.53	Ginsenoside Rg1	800.4922	C42H72O14	800.4939	845.4921	2.0	845.4921[M+HCOO]− 799.4863[M−H]− 637.4321[M−H-Glc]− 475.3784[M−H-2Glc]−	f
42	9.23	Kaempferol	286.0477	C15H10O6	286.0479	285.0406	0.7	285.0406[M−H]− 229.0451[M−H-C2O2]− 169.0141[M−H-C3O5]−	a,d
43g	9.46	Quercetin	302.0427	C15H10O7	302.0432	301.0360	2.0	301.0360[M−H]− 151.0451[M−H-C8H6O3]− 121.0431[M−H-C8H6O3-CH2O]− 107.0162[M−H-C8H6O3-CH2O-CH2]−	d
44	9.61	Aloin	418.1264	C21H22O9	418.1267	417.1195	0.8	417.1195[M−H]− 255.0666[M−H-Glc]− 227.0718[M−H-Glc-CO]−	a
45	9.76	Aloe emodin-1-O-β-D-glc	432.1056	C21H20O10	432.1068	431.0995	2.7	431.0995[M−H]− 269.0452[M−H-Glc]− 225.0562[M−H-Glc-CO2]−	a
46	9.91	Aloe emodin-ω-O-β-D-glc	432.1056	C21H20O10	432.1068	431.0995	2.7	431.0995[M−H]− 269.0463[M−H-Glc]− 225.0560[M−H-Glc-CO2]−	a
47	10.09	Chrysophanol-1-O-β-D-glc	416.1107	C21H20O9	416.1118	415.1045	2.6	415.1045[M−H]− 253.0515[M−H-Glc]− 225.0563[M−H-Glc-CO]−	a
48	10.91	Aloe emodin-8-(6"-O-malonyl)-glc	518.1060	C24H22O13	518.1076	517.1003	3.1	517.1003[M−H]− 473.1097[M−H-CO2]− 269.0463[M−H-malonyl-Glc]−	a
49	10.95	Calebin-A	384.1209	C21H20O7	384.1211	429.1193	0.5	429.1193[M+HCOO]−	c
50	11.16	Naringenin	272.0685	C15H12O5	272.0689	271.0616	1.5	271.0616[M−H]− 151.0665[M−H-C8H8O]−	d
51	11.25	Aloe emodin-8-O-β-D-(6"-O-acetyl)-glc	474.1162	C23H22O11	474.1169	473.1096	1.5	473.1096[M−H]− 269.0451[M−H-acetyl-Glc]− 240.0410[M−H-acetyl-Glc-CHO]−	a
52	11.77	Physcion-8-O-β-D-glc	446.1213	C22H22O10	446.1219	445.1146	1.3	445.1146[M−H]− 283.0617[M−H-Glc]− 240.0433[M−H-Glc-CO-CH3]−	a
53	11.85	Chysophanol-8-O-β-D-(6"-O-acetyl)-glc	458.1213	C23H22O10	458.1221	457.1148	1.8	457.1148[M−H]− 253.0511[M−H-acetyl-Glc]− 225.0561[M−H-acetyl-Glc-CO]−	a
54	12.18	Notoginsenoside R2	770.4816	C41H70O13	770.4843	815.4825	3.3	815.4825[M+HCOO]− 769.4768[M−H]− 637.4335[M−H-Xyl]− 475.3786[M−H-Xyl-Glc]−	f
55	12.53	Ginsenoside Rb1	1108.6029	C54H92O23	1108.6105	1107.5967	6.6	1107.5967[M−H]− 945.5469[M−H-Glc]− 783.4917[M−H-2Glc]− 621.4361[M−H-3Glc]− 459.3824[M−H-4Glc]−	f
56	12.69	Cyclocurcumin	368.1260	C21H20O6	368.1258	367.1186	-0.4	367.1186[M−H]− 175.0401[M−H-C11H12O3]−	c
57	12.74	Ginsenoside Rg2	784.4973	C42H72O13	784.4999	829.4982	3.2	829.4982[M+HCOO]− 783.4922[M−H]− 637.4326[M−H-Rha]− 475.3789[M−H-Rha-Glc]−	f
58	12.94	Ginsenoside Rh1	638.4394	C36H62O9	638.4414	683.4382	2.9	683.4382[M+HCOO]− 637.4321[M−H]− 475.3784[M−H-Glc]−	f
59	13.18	6-Methyl-rhein	298.0477	C16H10O6	298.0481	297.0408	1.1	297.0408[M−H]− 283.0251[M−H-CH2]− 239.0358[M−H-CH2-CO2]−	a
60	13.21	Physcion-8-O-β-D-(6"-O-acetyl)-glc	488.1319	C24H24O11	488.1323	487.1250	0.8	487.1250[M−H]− 283.0615[M−H-acetyl-Glc]− 255.0317[M−H-acetyl-Glc-CO]− 240.0432[M−H-acetyl-Glc-CO-CH3]−	a
61	13.51	Orientalol A	254.1882	C15H26O3	254.1907	299.1889	8.3	299.1889[M+HCOO]− 253.1905[M−H]−	c
62	14.13	16-Oxo-alisol A	504.3451	C30H48O6	504.3474	505.3223	4.3	505.3223[M+H]+ 487.3327[M+H-H2O]+ 469.3285[M+H-2H2O]+ 451.3318[M+H-3H2O]+ 415.2824[M+H-C4H10O2]+ 397.2783[M+H-C4H10O2-H2O]+	e
63	14.41	Ginsenoside Rd	946.5501	C48H82O18	946.5581	991.5563	8.0	991.5563[M+HCOO]− 945.5563[M−H]− 783.4939[M−H-Glc]− 621.4398[M−H-2Glc]− 459.3851[M−H-3Glc]−	f
64g	14.52	Aloe emodin	270.0528	C15H10O5	270.0536	269.0462	3.0	269.0462[M−H]− 240.0421[M−H-CHO]− 211.0410[M−H-2CHO]−	a
65g	15.30	Rhein	284.0321	C15H8O6	284.0332	283.0256	4.0	283.0256[M−H]− 239.0356[M−H-CO2]− 211.0403[M−H-CO2-CO]− 183.0439[M−H-CO2-CO-CO]−	a
66	16.01	Notoginsenoside R3	962.5450	C48H82O19	962.5491	961.5418	4.2	961.5418[M−H]− 799.4889[M−H-Glc]− 637.4360[M−H-2Glc]− 475.3817[M−H-3Glc]−	f
67	16.70	8-Oxoberberine	351.1107	C20H17NO5	351.1108	352.1181	0.4	352.1181[M+H]+ 337.0948[M+H-CH3]+ 294.0764[M+H-2CH3-CO]+	b
68	16.72	Alisol I	454.3447	C30H46O3	454.3460	455.3526	2.6	455.3526[M+H]+ 383.2943[M+H-C4H8O]+	e
69	17.05	Alisol C	486.3345	C30H46O5	486.3368	487.3418	4.2	487.3418[M+H]+ 469.3265[M+H-H2O]+ 451.3215[M+H-2H2O]+ 415.2841[M+H-C4H8O]+ 397.2746[M+H-C4H10O2]+	e
70	17.24	Ar-turmerone	216.1514	C15H20O	216.1516	217.1588	0.7	217.1588[M+H]+ 120.0935[M+H-C6H9O]+ 92.06212[M+H-C8H13O]+	c
71g	17.34	Kaempferide	300.0634	C16H12O6	300.0628	299.0553	-2.1	299.0553[M−H]− 284.0489[M−H-CH3]−	d
72	17.46	Bisdemethoxycurcumin	308.1049	C19H16O4	308.1058	307.0984	2.9	307.0984[M−H]− 187.0406[M−H-C8H8O]−	c
73	17.93	Demethoxycurcumin	338.1154	C20H18O5	338.1161	337.1088	2.0	337.1088[M−H]− 217.0508[M−H-C8H8O]−	c
74g	18.38	Curcumin	368.1260	C21H20O6	368.1260	367.1192	-0.1	367.1192[M−H]− 217.0524[M−H-C9H10O2]−	c
75	18.94	Alisol M 23-acetate	488.3502	C30H48O5	488.3497	489.3480	-0.8	489.3480[M+H]+ 471.2696[M+H-H2O]+	e
76g	19.25	Emodin	270.0528	C15H10O5	270.0533	269.0460	1.7	269.0460[M−H]− 241.0507[M−H-CO]− 225.0559[M−H-CO-O]−	a
77	19.54	Bisabolone oxide A	236.1776	C15H24O2	236.1776	237.1850	0.5	237.1850[M+H]+	c
78	19.65	Alisol C 23-acetate	528.3451	C32H48O6	528.3453	529.3535	1.0	529.3535[M+H]+ 511.3415[M+H-H2O]+ 469.3456[M+H-HAc]+	e
79	19.71	Alisol F	488.3502	C30H48O5	488.3497	511.3391	-1.4	511.3391[M+Na]+ 471.2696[M+H-H2O]+ 453.2687[M+H-2H2O]+ 399.3129[M+H-C4H10O2]+ 381.3091[M+H-C4H10O2-H2O]+	e
80	20.04	Alisol L 23-acetate	510.3345	C32H46O5	510.3350	511.3418	1.0	511.3418[M+H]+ 451.3201[M+H-HAc]+ 397.2739[M+H-C6H10O2]+	e
81	20.59	Procyanidin	594.1373	C30H26O13	594.1382	593.1309	0.8	593.1309[M−H]−	a
82	21.39	Neoalisol A	488.3502	C30H48O5	488.3505	489.3572	2.5	489.3572[M+H]+ 471.3571[M+H-H2O]+	e
83g	21.71	Chrysophanol	254.0579	C15H10O4	254.0579	253.0515	3.3	253.0515[M−H]− 225.0545[M−H-CO]−	a
84	21.72	16,23-Oxido alisol B	470.3396	C30H46O4	470.3395	493.3287	-0.2	493.3287[M+Na]+ 453.3362[M+H-H2O]+ 339.2686[M+H-C6H10O2-H2O]+	e
85	22.56	Gingerdione	292.1675	C17H24O4	292.1679	337.1661	1.4	337.1661[M+HCOO]− 291.1629[M−H]−	c
86g	22.80	Physcion	284.0685	C16H12O5	284.0692	283.0619	2.5	283.0619[M−H]− 255.0315[M−H-CO]− 240.0359[M−H-CO-CH3]−	a
87	22.90	Alisol A 23-acetate	532.3764	C32H52O6	532.3767	555.3749	0.6	555.3749[M+Na]+ 515.3516[M+H-H2O]+ 383.2797[M+H-C6H12O3-H2O]+	e
88	23.05	11-Deoxy-alisol C	470.3396	C30H46O4	470.3398	471.3380	0.3	471.3380[M+H]+ 453.3515[M+H-H2O]+ 399.2874[M+H-C4H8O]+	e
89	23.32	Stearic acid	284.2715	C18H36O2	284.2717	283.2645	0.7	283.2645[M−H]−	d
90	23.54	Alisol A	490.3658	C30H50O5	490.3678	491.3661	3.8	491.3661[M+H]+ 473.3515[M+H-H2O]+ 455.3621[M+H-2H2O]+ 437.3415[M+H-3H2O]+ 383.2973[M+H-H2O-C4H10O2]+	e
91	23.79	Alisol B	472.3553	C30H48O4	472.3558	473.3622	-0.7	473.3622[M+H]+ 455.3515[M+H-H2O]+ 437.3521[M+H-2H2O]+ 383.2943[M+H-H2O-C4H8O]+	e
92	23.93	Alisol L	468.3240	C30H44O4	468.3238	469.3310	-0.4	469.3310[M+H]+ 451.3188[M+H-H2O]+ 397.2745[M+H-C4H8O]+	e
93	24.47	Alisol O	512.3502	C32H48O5	512.3492	513.3581	0.3	513.3581[M+H]+ 495.3475[M+H-H2O]+ 453.3413[M+H-HAc]+ 435.3628[M+H-HAc-H2O]+	e
94	24.65	Linolenic acid	278.2246	C18H30O2	278.2245	277.2164	-1.4	277.2164[M−H]−	a,d
95	25.28	Alisol A 24-acetate	532.3764	C32H52O6	532.3761	555.3748	1.5	555.3748[M+Na]+ 515.3516[M+H-H2O]+ 497.3472[M+H-2H2O]+ 383.2797[M+H-C6H12O3-H2O]+	e
96g	25.38	Alisol B 23-acetate	514.3658	C32H50O5	514.3661	537.3554	0.5	537.3554[M+Na]+ 515.3735[M+H]+ 497.3629[M+H-H2O]+ 479.3508[M+H-2H2O]+ 437.3415[M+H-H2O-HAc]+ 383.2688[M+H-C6H12O3]+	e

Glc: glucose; Rha: rhamnose; Xyl: xylose; Res: resveratrol.

^aRheum palmatum L.

^bCoptis chinensis Franch.

^cCurcuma longa L.

^dLysimachia christinae Hance.

^eAlisma orientale (Sam.) Juzep.

^fPanax notoginseng (Burk.) F. H. Chen.

^gIdentified by comparison with reference standards.