Table 1.
Chromatographic and spectrometric information of HTyr identified metabolites.
| Νο | RT (min) |
EC | Exp. [M−H]− |
Theor. [M−H]− m/z | Δm (ppm) | RDB eq. |
Fragments MS/MS | Compartments | Metabolites | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| m/z | S0H | S1H | SID | SIR | C2H | C4H | C6H | C24H | ||||||||
| HTyr1 | 3.27 | C8H9O3 | 153.05617 | 153.05462 | −0.20 | 4.5 | 123 | + | + | t | t | + | + | + | + | HTyr |
| HTyr2 | 4.39 | C8H7O2 | 135.04541 | 135.0452 | 1.90 | 5.5 | nd | – | + | – | – | – | – | – | + | Quinone or epoxy or dihydro derivative of Tyr |
| HTyr3 | 4.64 | C9H9O4 | 181.05087 | 181.0506 | 1.32 | 5.5 | nd | – | – | – | – | – | + | + | + | Dihydrocaffeic acid |
| HTyr4 | 4.70 | C7H5O3 | 137.02500 | 137.02514 | 1.40 | 5.5 | nd | – | + | + | – | t | t | – | – | Hydroxybenzoic acid |
| HTyr5 | 4.72 | C8H7O3 | 151.0408 | 151.0401 | 4.6 | 5.5 | 123,103 | + | + | t | – | + | + | + | + | DOPAL (3 , 4 dihydroxyphenyl acetaldehyde) |
| HTyr 6 | 5.51 | C9H7O3 | 163.0405 | 163.0401 | 2.50 | 6.5 | nd | – | – | – | – | – | – | – | + | Coumaric acid |
| HTyr 7 | 6.19 | C8H7O4 | 167.0428 | 167.0428 | 0.23 | 5.5 | nd | – | – | – | – | + | + | + | + | DOPAC (dihydroxyphenylacetic acid) |
| HTyr8 | 6.24 | C9H11O4 | 183.0665 | 183.0663 | 1.01 | 4.5 | nd | – | – | – | – | + | + | + | + | 4–( 1 ,3–dihydroxypropyl) benzene–1,2–diol |
| HTyr9 | 6.38 | C8H7O2 | 135.0454 | 135.0452 | 2.1 | 5.5 | nd | – | + | + | + | + | + | + | + | PPA (phenylacetic acid) |
| HTyr10 | 6.26 | C9H7O4 | 179.0351 | 179.0350 | 0.54 | 6.5 | nd | – | – | + | + | + | + | + | + | Caffeic acid |
| HTyr 1 1 | 6.48 | C16H17O9 | 353.0872 | 353.0878 | −1.65 | 8.5 | 235,265,247 | – | – | + | – | – | – | – | – | Hydroxylated dimer of HTyr (homodimer) |
| HTyr 1 2 | 6.98 | C7H5O2 | 121.0299 | 121.0295 | 2.96 | 5.5 | nd | – | t | t | t | t | t | t | t | Benzoic acid |
| HTyr 1 3 | 8.03 | C16H17O4 | 273.0766 | 273.0768 | −0.79 | 9.5 | nd | – | – | – | – | + | + | + | + | Dimer of HTyr (heterodimer) |
| HTyr 1 4 | 8.11 | C16H15O8 | 335.0766 | 335.0772 | −1.90 | 9.5 | nd | – | – | + | + | + | – | – | – | Hydroxylated dimer of HTyr (homodimer) |
| HTyr15 | 8.35 | C16H17O6 | 305.1028 | 305.1031 | −0.91 | 8.5 | 275,179,161 | – | + | – | – | – | – | – | – | Dimer of HTyr (homodimer) |
| HTyr16 | 8.75 | C9H9O3 | 165.05594 | 165.05462 | 1.30 | 5.5 | 147 | – | – | – | – | – | + | + | + | Hydroxyphenyl propionic acid |
| HTyr17 | 8.78 | C9H7O2 | 147.0454 | 147.0454 | 1.64 | 6.5 | 119 | – | – | – | – | – | + | + | + | Dehydrated hydroxyphenyl propionic acid |
| HTyr18 | 8.78 | C8H7O | 119.0505 | 119.0502 | 2.38 | 5.5 | nd | – | – | – | – | – | – | + | + | Phenylacetaldehyde |
| HTyr19 | 9.20 | C10H11O2 | 163.0767 | 163.0767 | 1.3 | 5.5 | nd | – | t | – | – | – | – | – | – | Phenylethyl acetate or 4–(4–hydroxyphenyl)–2–oxobutane |
| HTyr 2 0 | 9.20/ 10.29 |
C23H23O10 | 459.1291 | 459.1297 | −1.33 | 12.5 | nd | – | – | + | + | – | – | – | – | Trimer of HTyr (homodimer) |
| HTyr 2 1 | 9.22–11.74 | C11H13O3 | 193.0871 | 193.0870 | 0.49 | 5.5 | 163 | – | + | – | – | – | – | – | – | 4–methoxyphenethyl acetate or 4–(3–hydroxy–4–methoxy–phenyl)–butan–2–one |
| HTyr 2 2 | 9.24/ 9.53/ 10.35/10.75 |
C23H23O9 | 443.1341 | 443.1348 | −1.49 | 12.5 | 247,399 | – | – | + | + | – | – | – | – | Hydroxylated trimer of HTyr (heterodimer) |
| HTyr 2 3 | 3.52/9.87 | C10H11O4 | 195.06632 | 195.0663 | 0.17 | 5.5 | nd | – | + | – | – | + | + | + | + | Hydroxytyrosol acetate |
| HTyr 2 4 | 9.97 | C10H11O5 | 211.0611 | 211.0612 | −0.40 | 5.5 | nd | – | – | – | – | + | + | – | – | Hydroxylated Hydroxytyrosol acetate |
| HTyr25 | 8.12/ 11.29 |
C16H15O6 | 303.0870 | 303.0874 | −1.43 | 9.5 | 167,123 | – | + | – | + | + | + | + | + | Hydroxylated dimer of HTyr |
| HTyr26 | 11.75 | C16H17O5 | 289.10779 | 289.10779 | 0.73 | 8.5 | 135,153 | + | + | t | – | + | + | + | + | Dimer of HTyr (heterodimer) |
| HTyr27 | 12.71 | C23H21O9 | 441.1185 | 441.1191 | −1.30 | 13.5 | nd | – | – | + | – | – | – | – | – |
Trimer of HTyr–2H
(homodimer) |
RT: Retention Time; EC: Elemental Composition, RDBeq.: Ring Double Bond equivalent; t: traces; nd: not detected.