Table 2.
Identification and detection of metabolites of GZD in rat plasma and urine samples by RRLC-Q-TOF-MS.
| No. | tR (min) | Identification | Formula | Urine | Plasma | Negative Ion (m/z) | Possible Original Compound | Source | |
|---|---|---|---|---|---|---|---|---|---|
| Quasi-Molecular (ppm) | MS/MS (m/z) | ||||||||
| M1 | 4.494 | Catechin-O-glucuronide | C21H22O12 | + | - | 465.0785 | 289.0622, 245.0724 | (Epi) catechin-related | P |
| M2 | 9.026 | 3’-O-Methyl (epi)catechin 5-O-glucuronide | C21H24O12 | + | - | 479.0965 | 303.0976, 175.0176 | (Epi) catechin-related | P |
| M3 | 10.220 | 3’-O-Methyl (epi)catechin 7- or 4’-O-glucuronide | C21H24O12 | - | + | 479.0948 | 303.0876, 175.0242 | (Epi) catechin-related | P |
| M4 | 8.861 | 5-(3,4-Dihydroxyphenyl)-γ-valerolactone glucuronide | C17H20O10 | + | - | 383.0757 | 207.0587, 163.0691 | (Epi) catechin-related | P |
| M5 | 5.949 | 5-(3,4-Dihydroxyphenyl)-γ-valerolactone sulfate | C11H12O7S | + | - | 287.0027 | 207.0580, 163.0685 | (Epi) catechin-related | P |
| M6 | 17.003 | 5-(3-Methoxyl-4-hydroxyphenyl)-valerolactone glucuronide | C18H22O10 | + | - | 397.0907 | 221.0719 | (Epi) catechin-related | P |
| M7 | 19.489 | 5-(3-Methoxyl-4-hydroxyphenyl)-valerolactone sulfate | C12H14O7S | + | - | 301.0187 | 221.0739, 206.0503 | (Epi) catechin-related | P |
| M8 | 9.305 | 5-(3-Hydroxyphenyl)-γ-valerolactone sulfate | C11H12O6S | + | - | 271.0092 | 191.0624 | (Epi) catechin-related | P |
| M9 | 4.276 | 4-Hydroxy phenylpropionic acid sulfate | C9H10O6S | + | - | 244.9955 | 165.0596 | (Epi) catechin-related | P |
| M10 | 9.549 | 3-Hydroxy phenylpropionic acid sulfate | C9H10O6S | + | - | 245.0320 | 165.0846 | (Epi) catechin-related | P |
| M11 | 8.547 | 3,4-Dihydroxy phenylpropionic acid sulfate | C9H10O7S | + | - | 260.9888 | 181.0409, 166.0193 | (Epi) catechin-related | P |
| M12 | 2.022 | 3-Hydroxy-4-methoxy-phenylpropionic acid sulfate | C10H12O7S | + | - | 275.0040 | 195.0717 | (Epi) catechin-related | P |
| M13 | 5.027 | 3-Methoxy-4-hydroxy-phenylpropionic acid sulfate | C10H12O7S | + | + | 275.0042 | 195.0504 | (Epi) catechin-related | P |
| M14 | 4.511 | m-Coumaric acid sulfate | C9H8O6S | + | - | 242.9793 | 163.0324 | (Epi) catechin-related | P |
| M15 | 14.077 | p-Coumaric acid sulfate | C9H8O6S | + | - | 243.0173 | 163.0694 | (Epi) catechin-related | P |
| M16 | 10.666 | Ferulic acid sulfate | C10H10O7S | + | + | 273.0259 | 193.0845 | (Epi) catechin-related | P |
| M17 | 9.057 | 3-Hydroxy-4-methoxyphenylacetic acid sulfate | C9H10O7S | + | - | 261.0254 | 181.0718 | (Epi) catechin-related | P |
| M18 | 1.661 | 3,4-Dihydroxy phenylacetic acid sulfate | C8H8O7S | + | - | 247.0111 | 167.0575 | (Epi) catechin-related | P |
| M19 | 1.713 | Protocatechuic acid-3- or -4-O-sulfate | C7H6O7S | + | - | 232.9967 | 153.0423 | (Epi) catechin-related | P |
| M20 | 20.086 | Benzoyl glucuronide | C13H14O8 | + | - | 297.0939 | 121.0658 | (Epi) catechin-related | P |
| M21 | 9.92 | 3-Hydroxyhipuric acid | C9H9NO4 | + | - | 194.0298 | 150.0462 | (Epi) catechin-related | P |
| M22 | 13.393 | Gallic acid glucuronide | C13H14O11 | + | + | 345.1354 | 169.1232 | Gallic acid-related | P |
| M23 | 17.521 | 4-O-Methylgallic acid | C8H8O5 | + | - | 183.0887 | 168.0197, 139.0268 | Gallic acid-related | P |
| M24 | 14.378 | 4-O-Methylgallic acid glucuronide | C14H16O11 | + | - | 359.1115 | 191.0628, 183.0944 | Gallic acid-related | P |
| M25 | 1.202 | 2-Deoxy-pyrogallol-1-O-sulfate | C6H6O5S | + | - | 188.9718 | 125.0010, 109.0087 | Gallic acid-related | P |
| M26 | 0.845 | Pyrogallol-2-O-sulfate | C6H6O6S | + | - | 204.9665 | 125.0126 | Gallic acid-related | P |
| M27 | 1.254 | Pyrogallol-1-O-sulfate | C6H6O6S | + | - | 204.9665 | 124.9982 | Gallic acid-related | P |
| M28 | 30.462 | 2-O-Methylpyrogallol glucuronide | C13H16O9 | + | - | 315.2336 | 171.1027, 139.1119 | Gallic acid-related | P |
| M29 | 0.888 | 2-O-Methylpyrogallol sulfate | C7H8O6S | + | - | 218.9790 | 139.0419, 124.0168 | Gallic acid-related | P |
| M30 | 1.228 | 1-O-Methylpyrogallol-3-O-sulfate | C7H8O6S | + | - | 218.9809 | 139.0277 | Gallic acid-related | P |
| M31 | 2.021 | 1-O-Methylpyrogallol-2-O-sulfate | C7H8O6S | + | - | 218.9809 | 139.0273 | Gallic acid-related | P |
| M32 | 17.146 | Paeonimetabolin I glucuronide isomer I or II | C16H22O10 | + | - | 373.1311 | 197.1181 | Paeoniflorin-related | P |
| M33 | 8.939 | C10H14O3 sulfate | C10H14O6S | + | - | 260.9913 | 181.0443 | Paeoniflorin-related | P |
| M34 | 14.952 | C10H18O2 glucuronide | C16H26O8 | + | - | 345.1354 | 169.1223 | Paeoniflorin-related | P |
| M35 | 19.135 | Naringenin | C15H12O5 | + | - | 271.0419 | 151.0032 | Naringenin-O-glucoside -related | G |
| M36 | 16.194 | Naringenin-O-glucuronide-O-sulfate | C21H20O14S | + | - | 527.0264 | 447.0951, 351.0192, 271.0628 | Naringenin-O-glucoside-related | G |
| M37 | 15.292 | Naringenin-4’-O-glucuronide | C21H20O11 | + | - | 447.1025 | 271.0887, 175.0160 | Naringenin-O-glucoside-related | G |
| M38 | 17.312 | Naringenin-7-O-glucuronide | C21H20O11 | + | - | 447.1025 | 271.0887, 175.0160, 150.9851 | Naringenin-O-glucoside-related | G |
| M39 | 13.133 | Naringenin-O-sulfate | C15H12O8S | + | - | 350.9982 | 271.0390, 150.9829 | Naringenin-O-glucoside-related | G |
| M40 | 16.690 | Liquiritigenin-O-glucuronide-O-sulfate | C21H20O13S | + | - | 511.0306 | 431.0900, 335.0135 | Liquiritigenin-related | G |
| M41 | 13.386 | 7,4’-Dihydroxyflavone-O-sulfate | C15H10O7S | + | - | 332.9885 | 253.0431 | Liquiritigenin-related | G |
| M42 | 13.619 | Liquiritigenin-4’-O-sulfate | C15H12O7S | + | - | 335.0018 | 255.0569, 134.9995 | Liquiritigenin-related | G |
| M43 | 14.230 | Liquiritigenin-7-O-sulfate | C15H12O7S | + | - | 335.0018 | 255.0658, 135.0088 | Liquiritigenin-related | G |
| M44 | 12.532 | Liquiritigenin-4’-O-glucuronide | C21H20O10 | + | - | 431.0754 | 255.0498, 113.0137 | Liquiritigenin-related | G |
| M45 | 12.924 | Liquiritigenin-7-O-glucuronide | C21H20O10 | + | - | 431.0754 | 255.0499, 113.0132 | Liquiritigenin-related | G |
| M46 | 29.631 | Isoliquiritigenin-O-sulfate | C15H12O7S | + | - | 335.2224 | 255.2111 | Isoliquiritigenin-related | G |
| M47 | 16.023 | Isoliquiritigenin-4’-O-glucuronide | C21H20O10 | + | + | 431.0754 | 255.0672, 113.0247 | Isoliquiritigenin-related | G |
| M48 | 16.441 | Isoliquiritigenin-7-O-glucuronide | C21H20O10 | + | - | 431.0754 | 255.0559, 113.0163 | Isoliquiritigenin-related | G |
| M42 | 13.619 | Liquiritigenin-4’-O-sulfate | C15H12O7S | + | - | 335.0018 | 255.0569, 134.9995 | Liquiritigenin-related | G |
| M43 | 14.230 | Liquiritigenin-7-O-sulfate | C15H12O7S | + | - | 335.0018 | 255.0658, 135.0088 | Liquiritigenin-related | G |
| M44 | 12.532 | Liquiritigenin-4’-O-glucuronide | C21H20O10 | + | - | 431.0754 | 255.0498, 113.0137 | Liquiritigenin-related | G |
| M45 | 12.924 | Liquiritigenin-7-O-glucuronide | C21H20O10 | + | - | 431.0754 | 255.0499, 113.0132 | Liquiritigenin-related | G |
| M46 | 29.631 | Isoliquiritigenin-O-sulfate | C15H12O7S | + | - | 335.2224 | 255.2111 | Isoliquiritigenin-related | G |
| M47 | 16.023 | Isoliquiritigenin-4’-O-glucuronide | C21H20O10 | + | + | 431.0754 | 255.0672, 113.0247 | Isoliquiritigenin-related | G |
| M48 | 16.441 | Isoliquiritigenin-7-O-glucuronide | C21H20O10 | + | - | 431.0754 | 255.0559, 113.0163 | Isoliquiritigenin-related | G |
| M49 | 18.463 | Fomononetin-O-sulfate | C16H12O7S | + | - | 347.0012 | 267.0637 | Fomononetin-related | G |
Note: tR (min): Retention time; P: Radix Paeoniae Alba; G: Radix Glycyrrhizae; C: Ramulus Cinnamomi; ZR: Zingiberis Recens; +: Detected; -: Not detected.