Table 1.
Oleuropein data after LC-ESI-MS2 analysis of Ole, Mix, and Mix-seq before and after electrochemical oxidation.
| Compound Name | RT (min) | λmax (nm) | m/z | Ole 2 mM | Mix 2 mM | Mix-seq 2 mM | MS2 | |||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Ref | Ox | Ref | Ox | (Tyr + p-Cou) Ox + Ole | Ox | |||||||||
| O1 | 3,4-Dihydroxyphenylglycol | 4.1 | 280 | 169 | traces | + | − | + | − | + | 151 (−18) | 123 (−46) | ||
| O2 | 11-Methyl-oleoside | 22.0 | <240 | 403 | traces | + | traces | + | + | + | 223 (−180) | 179 (−224) | 359 (−CO2) | 161 (−242) |
| O3 | unknown | 30.8 | 587 | + | + | + | + | + | + | 543 (−44) | 403 (−184) | |||
| O4 | unknown | 32.4 | 288 | 573 | + | traces | traces | + | traces | - | 529 (−44) | 403 (−170) | 222 (−350) | |
| O5 | 10- Hydroxy-oleuropein | 35.1 | 555 | + | + | + | + | + | + | 537 (−H2O) | 393 (162) | 403 (−152) | ||
| O6 | Oleuropein + [EtOH] | 35.8 | 244/307 | 585 | + | + | + | + | + | + | 523 (−62) | 541 (−44) | 361 (−224) | 199 (−386) |
| 403 (−182) | ||||||||||||||
| O7 | unknown | 37.0 | 255 | 615 | + | + | + | + | + | + | 423 (−191) | 455 (−160) | 273 (−344) | 551 (−64) |
| O8 | unknown | 37.8 | 266/336 | 617 | traces | traces | - | + | + | + | 423 (−194) | 455 (−162) | 273 (−344) | 585 (−32) |
| O9 | unknown | 38.0 | 266/337 | 431 | + | traces | + | + | + | + | 269 (−162) | |||
| O10 | unknown | 38.3 | 267/344 | 567 | traces | + | traces | + | - | + | 373 (−194) | 403 (−164) | 223 (−344) | |
| O11 | unknown | 38.3 | 461 | + | + | + | + | + | + | 299 (−162) | 446 (−15) | 307 (−154) | ||
| O12 | Oleuropein | 38.4 | 278 | 539 | + | + | + | + | + | + | 377 (−162) | 307 (−232) | 275 (−264) | |
| O13 | unknown | 38.6 | - | 553 | + | + | traces | + | + | + | 403 (−150) | 223 (−330) | 179 (−374) | |
| O14 | Oleuropein diglucoside | 38.6 | 309 | 701 | + | + | + | + | + | + | 377 (−324) | 307 (394) | 275 (−426) | |
| O15 | Ole dimer | 39.5 | 1077 | traces | + | traces | + | traces | - | 673 (−404) | 813 (−264) | 539 (−538) | ||
| O16 | Ole quinone dimer derivative | 39.8 | 263/420 | 1091 | − | + | − | + | traces | + | 687 (−404) | 403 (−688) | 525 (−56) | |
| O17 | Oleuropein quinone | 39.9 | 295 | 537 | traces | + | traces | traces | traces | + | − | |||
| O18a | Oxidized lucidumoside C | 40.3 | 259/434 | 581 | − | + | − | + | + | + | 535 (-46) | 403 (−178) | ||
| O19 | Oxidized Ole trimer | 40.3 | 1647 | − | + | − | traces | − | + | 685 (−962) | 1109 (−538) | |||
| O20 | Lucidumoside C | 40.6 | 255/350 | 583 | − | + | − | − | + | + | 537 (−46) | |||
| O18b | Oxidized lucidumoside C | 41.0 | <240/412 | 581 | − | + | + | traces | + | + | ||||
| O21 | Ole trimer derivative | 41.2 | 280 | 1619 | − | + | − | + | + | + | 1575 (−CO2) | 1557 (−CO2, −H2O) | 1019 | |
| O22 | Iso Ole trimer derivative | 41.6 | 280 | 1619 | − | + | − | + | + | + | 1575 | 1557 | 1019 | |
| O23 | Iso Ole dimer | 41.7 | 1077 | + | - | + | - | traces | − | 813 (−264) | 673 (−404) | 539 (−538) | ||
| O24 | Ole trimer derivative | 42.6 | 281 | 1629 | − | + | − | + | + | + | 1019 | 1045 | 1585 | 1091 |
| O25 | Ole trimer derivative | 43.6 | 285 | 1601 | traces | + | − | + | traces | + | 1197 | 793 | ||