UHPLC-ESI-Orbitrap-MS Analysis of Biologically Active Extracts from Gynura procumbens (Lour.) Merr. and Cleome gynandra L. Leaves

Table 2

Tentative identification of phenolic compounds from the extracts of G. procumbens and C. gynandra.

No	TR (min)	Measured mass[M-H]^−m/z	Theoretical mass[M-H]^−m/z	Mass error (ppm)	MS/MSm/z (% intensity)	Tentatively identified metabolites	100% GP	20% CG	100% CG	Reference(s)
Sugar derivatives
1	5.55	371.0621	371.0693	−19.4	209 (20), 191 (20), 179 (5), 173 (5), 85 (100)	Caffeoylglucaric acid	+	+	−	[37]
2	7.07	355.0671	355.0744	−20.6	209 (4), 191 (3), 163 (4), 119 (5), 85 (100)	Coumaroylglucaric acid	−	+	−	[37]
3	7.82	355.0673	355.0744	−20.0	209 (40), 191 (10), 163 (3), 133 (8), 119 (4), 85 (100)	Isomer of coumaroylglucaric acid	−	+	−	[37]
4	9.62	355.0673	355.0744	−20.0	337 (1), 209 (20), 191 (20), 173 (3), 163 (3), 85 (100)	Isomer of coumaroylglucaric acid	+	−	−	[37]
5	19.91	465.2257	n.d	n.d	261 (6), 243 (100), 221 (70), 177 (3), 149 (2)	Derivative of acetylglucose	−	+	+	[37]
Organic acids
6	1.76	275.0216	n.d	n.d	159 (20), 227 (1), 133 (1), 115 (100), 71 (25)	Derivative of malic acid	−	+	−	[38]
7	1.78	217.9913	n.d	n.d	133 (15), 125 (10), 115 (99), 89 (10), 71 (100)	Derivative of malic acid	−	−	+	[38]
8	1.83	289.0177	n.d	n.d	133 (60), 115 (100), 71 (35)	Derivative of malic acid	−	+	−	[38]
9	1.93	133.0211	133.0215	−3.0	115 (40), 71 (100)	Malic acid	−	+	+	[38]
10	2.15	405.0248	n.d	n.d	191 (40), 173 (10), 129 (5), 111 (100), 87 (20)	Derivative of citric acid	−	+	+	[38]
11	2.30	191.0189	191.0270	−42.4	173 (10), 111 (50), 87 (100), 85 (30), 67 (30), 57 (55)	Citric acid	−	+	+	[38]
Hydroxybenzoic acid derivatives
12	3.61	315.0724	315.0794	−22.2	153 (80), 109 (100)	Protocatechuic acid glucoside	+	−	−	[39]
13	3.55	351.0599	n.d	n.d	198 (10), 180 (4), 169 (20), 125 (60), 111 (100) 79 (60)	Derivative of gallic acid	−	+	−	[40]
14	4.53	331.0672	331.0743	−21.4	313 (6), 169 (100), 150 (40), 125 (98)	Gallic acid glucoside	+	−	−	[40]
15	5.30	315.0724	315.0794	−22.2	152 (80), 108 (100)	Isomer of protocatechuic acid glucoside	+	−	−	[39]
16	6.23	153.0269	153.0266	1.96	123 (10), 109 (80), 108 (100), 97 (10), 91 (15), 81 (10), 65 (13)	Protocatechuic acid	+	−	−	[39]
17	6.64	211.0607	n.d	n.d	153 (60), 148 (100), 138 (12), 136 (15), 123 (10), 120 (20), 109 (70), 108 (40), 95 (20)	Protocatechuic acid derivative	+	−	−	[39]
18	8.27	299.0772	299.0845	−24.4	137 (60), 93 (100)	Hydroxybenzoic acid glucoside	+	−	−	[41]
19	13.42	280.0649	n.d	n.d	217 (6), 145 (40), 137 (20), 119 (100), 117 (15), 93 (15)	Derivative of hydroxybenzoic acid	+	−	−	[41]
Flavonoid derivatives
20	13.80	609.1464	609.1534	−11.5	343 (4), 301 (100), 179 (5), 151 (4)	Quercetin rutinoside	−	+	+	[38]
21	14.28	463.0884	463.0877	1.5	301 (50), 300 (100), 271 (5), 255 (3), 179 (4), 175 (2), 151 (4)	Quercetin glucoside	−	+	−	[38]
22	14.74	593.1516	593.1585	−11.6	327 (3), 285 (100), 151 (2)	Kaempferol rutinoside	−	+	+	[38]
23	18.26	615.2463	n.d	n.d	571 (10), 553 (6), 386 (4), 285 (100), 241 (4), 213 (1)	Derivative of luteolin	−	+	+	[38]
Hydroxycinnamic acid derivatives
24	2.44	248.0539	n.d	n.d	180 (20), 163 (60), 153 (10), 119 (100), 107 (15), 93 (20), 72 (50)	Derivative of coumaric acid	−	+	+	[41]
25	6.80	341.0881	341.0951	−20.5	179 (70), 135 (100)	Caffeic acid glucoside	−	+	−	[42]
26	6.85	353.0879	353.0951	−20.4	191 (100), 179 (50), 161 (4), 135 (80), 111 (4), 93 (2), 85 (4)	3-Caffeoylquinic acid	+	−	−	[38, 41, 42]
27	7.56	385.0718	385.0713	1.29	223 (40), 205 (60), 147 (10), 129 (30), 111 (60), 101 (20), 85 (100)	Sinapic acid glucoside	+	−	−	[43]
28	8.13	297.0616	n.d	n.d	179 (1), 161 (10), 135 (100), 117 (10), 89 (20)	Derivative of caffeic acid	−	+	+	[42]
29	8.66	707.1831	n.d	n.d	353 (20), 191 (100), 179 (1), 161 (1)	Dimer of caffeoylquinic acid	+	−	−	[44]
30	9.04	325.0930	325.1002	−22.1	163 (20), 119 (100)	Coumaric acid glucoside	+	+	+	[41]
31	9.16	353.0879	353.0951	−20.4	191 (80), 179 (50), 173 (70), 161 (10), 135 (100), 111 (20), 93 (30)	4-Caffeoylquinic acid	+	−	−	[41]
32	9.37	369.0369	369.0365	1.08	207 (10), 189 (25), 127 (100), 83 (50)	Dimethoxycinnamoyl glucoside	−	+	+	[45]
33	9.63	739.1000	n.d	n.d	369 (12), 207 (15), 189 (100), 127 (20)	Dimer of dimethoxycinnamoyl glucoside	−	+	−	[45]
34	9.63	369.0364	369.0365	−0.27	207 (2), 189 (10), 127 (100), 99 (20), 83 (80)	Dimethoxycinnamoyl glucoside	−	−	+	[45]
35	9.92	179.0341	179.0423	−45.8	135 (100), 117 (8), 107 (10), 89 (15)	Caffeic acid	−	+	−	[37, 42]
36	10.33	353.0879	353.0951	−20.4	191 (100), 179 (1), 173 (2), 161 (3), 127 (2), 111 (1), 85 (4)	5-Caffeoylquinic acid	+	−	−	[38, 41, 42]
37	10.58	337.0931	337.1002	−21.1	191 (100), 173 (5), 163 (20), 127 (3), 119 (20), 111 (10), 93 (50)	trans-5-p-Coumaroylquinic acid	+	−	−	[46]
38	11.09	321.1015	n.d	n.d	321 (20), 241 (2), 175 (2), 147 (20), 119 (2), 103 (4), 97 (100)	Derivative of cinnamic acid	+	−	−	[47]
39	11.71	367.1034	367.1107	−19.9	191 (100), 173 (30), 155 (4), 134 (20), 111 (20), 93 (50)	Feruloylquinic acid	+	−	−	[38, 46]
40	11.83	375.0332	n.d	n.d	185 (50), 163 (30), 134 (10), 127 (25), 119 (100), 103 (10), 101 (40), 83 (20)	Derivative of coumaric acid	−	+	−	[41]
41	11.83	353.0409	353.0404	1.41	207 (1), 189 (10), 127 (100), 119 (5), 99 (20), 83 (90)	Dimethoxycinnamoyl coumaric acid	−	+	+	[45]
42	12.82	337.0930	337.1002	−21.4	191 (100), 173 (2), 163 (2), 127 (2), 119 (2), 93 (4)	cis-5-p-Coumaroylquinic acid	+	−	−	[38, 46]
43	12.84	383.0620	383.0736	−30.3	207 (1), 189 (10), 127 (100), 99 (20), 83 (80)	Dimethoxycinnamoyl glucoronide	−	+	+	[45]
44	15.07	515.1193	515.1267	−14.4	353 (30), 335 (20), 191 (40), 179 (90), 173 (100), 161 (20), 135 (20)	3,4-Dicaffeoylquinic acid	+	−	−	[48]
45	15.38	515.1195	515.1267	−14.4	353 (20), 191 (100), 179 (75), 173 (4), 161 (4), 135 (10)	3,5-Dicaffeoylquinic acid	+	−	−	[49]
46	15.66	515.1196	515.1267	−14.2	353 (20), 191 (100), 179 (80), 173 (15), 161 (5), 135 (10)	1,5-Dicaffeoylquinic acid	+	−	−	[49]
47	15.86	515.1196	515.1267	−14.2	353 (25), 191 (30), 179 (80), 173 (100), 161 (2), 155 (6), 135 (10)	1,4-Dicaffeoylquinic acid	+	−	−	[48]
48	16.43	499.1019	499.1002	3.4	337 (3), 191 (8), 173 (6), 163 (100), 119 (6)	Caffeoyl-coumaroylquinic acid	+	−	−	[50]
49	16.75	387.1086	n.d	n.d	193 (100), 179 (3), 161 (8), 133 (4)	Dimer of caffeic acid methyl ester	−	+	−	[42, 51]
50	16.77	529.1353	529.1424	−13.4	367 (8), 193 (100), 179 (4), 173 (8)	Caffeoyl-feruloylquinic acid	+	−	−	[40]
51	16.85	515.1196	515.1267	−14.2	353 (30), 191 (40), 179 (80), 173 (100), 155 (10), 135 (10)	4,5-Dicaffeoylquinic acid	+	−	−	[48]
52	18.39	207.0657	207.0736	−38.2	179 (2), 161 (30), 135 (90), 133 (100), 117 (2), 106 (3), 89 (2)	Caffeic acid ethyl ester	−	+	−	[42, 51]
53	22.61	559.3124	n.d	n.d	339 (3), 277 (100), 253 (20), 235 (2), 179 (1), 161 (2)	Derivative of caffeic acid	−	−	+	[42]
Other classes of phenolic acid
54	6.04	315.1087	315.1158	−22.5	153 (60), 123 (100)	Hydroxytyrosol glucoside	+	−	−	[39]
55	7.03	403.0915	n.d	n.d	343 (30), 241 (20), 181 (4), 166 (3), 151 (6), 139 (4), 111 (80), 97 (100)	Derivative of syringaldehyde	+	−	−	[39]
56	7.40	339.0721	339.0794	−21.5	225 (2), 203 (2), 177 (100), 133 (10)	Esculetin glucoside	−	+	+	[52]
57	7.42	471.1146	471.1217	−15.1	177 (100), 133 (10)	Esculetin sambubioside	+	−	−	[52]
58	8.72	343.1035	343.0906	−37.6	181 (100), 137 (70), 121 (8), 109 (10)	Homovanillic acid glucoside	−	+	+	[38]

GP: Gynura procumbens, CG: Cleome gynandra, n.d: not determined. (−) and (+) indicate absence or presence of the metabolite in the extract. Bold metabolites indicate metabolites identified tentatively for the first time in the respective herbs.