Table 2.
Tentative identification of phenolic compounds from the extracts of G. procumbens and C. gynandra.
| No | T R (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.