Table 2. Resveratrol and Its Derived Metabolites in Urine, Feces, and (or) Fecal Culturesa.
| N° | compound | RT (min) | mass accuracy (m/z–) | molecular formula | error (ppm) | score | occurrence |
|---|---|---|---|---|---|---|---|
| UPLC-QTOF-MS (non-hydrolyzed samples) | |||||||
| 1 | resveratrol (RSV) diglucuronide (isomer-1)b | 4.43 | 579.1355 | C26H28O15 | 1.18 | 98.87 | U |
| 2 | RSV diglucuronide (isomer-2)b | 4.90 | 579.1355 | C26H28O15 | 0.06 | 99.66 | U |
| 3 | RSV sulfoglucuronide (isomer-1)b | 5.21 | 483.0603 | C20H20O12S | –0.38 | 97.96 | U |
| 4 | DHRSV diglucuronideb | 5.73 | 581.1512 | C26H30O15 | 0.56 | 99.18 | U |
| 5 | RSV sulfoglucuronide (isomer-2)b | 5.89 | 483.0603 | C20H20O12S | 0.15 | 97.69 | U |
| 6 | RSV 4′-O-glucuronideb | 6.28 | 403.1035 | C20H20O9 | –1.14 | 98.73 | U |
| 7 | DHRSV sulfoglucuronideb | 6.30 | 485.0759 | C20H22O12S | 0.6 | 98.64 | U |
| 8 | RSV 3-O-glucuronide* | 7.55 | 403.1035 | C20H20O9 | –1.99 | 97.07 | U |
| 9 | DHRSV 4′-O-glucuronideb | 7.69 | 405.1191 | C20H22O9 | 1.21 | 98.39 | U |
| 10 | RSV 4′-O-sulfate* | 7.75 | 307.0282 | C14H12O6S | –0.11 | 99.1 | U |
| 11 | DHRSV 4′-O-sulfateb | 8.42 | 309.0438 | C14H14O6S | –0.96 | 99.01 | U, F |
| 12 | DHRSV 3-O-glucuronide* | 8.43 | 405.1191 | C20H22O9 | –0.02 | 97.09 | U |
| 13 | RSV 3-O-sulfate* | 8.77 | 307.0282 | C14H12O6S | –1.95 | 96.76 | U |
| 14 | DHRSV 3-O-sulfateb | 9.05 | 309.0438 | C14H14O6S | 0.47 | 97.67 | U, F |
| 15 | RSV* | 10.79 | 227.0714 | C14H12O3 | –1.63 | 86.23 | F |
| 16 | DHST-glucuronide (isomer-1)b | 10.92 | 387.1085 | C20H20O8 | –1.82 | 97.51 | U |
| 17 | DHST-glucuronide (isomer-2)b | 11.12 | 387.1085 | C20H20O8 | –2.36 | 92.66 | U |
| 18 | DHRSV* | 11.35 | 229.0870 | C14H14O3 | –1.42 | 98.56 | F, FC |
| 19 | LUNU glucuronide (isomer-1)b | 11.55 | 389.1242 | C20H22O8 | 0.24 | 99.38 | U, F |
| 20 | LUNU glucuronide (isomer-2)b | 11.65 | 389.1242 | C20H22O8 | –0.42 | 99.4 | U, F |
| 21 | DHST sulfateb | 11.69 | 291.0333 | C14H12O5S | 0.08 | 76c | U |
| 22 | LUNU sulfate (isomer-1)b | 12.07 | 293.0489 | C14H14O5S | –1.22 | 98.52 | U, F, FC |
| 23 | LUNU sulfate (isomer-2)b | 12.99 | 293.0489 | C14H14O5S | –2.12 | 97.8 | U, F, FC |
| 24 | LUNU* | 15.34 | 213.0921 | C14H14O2 | –1.01 | 99.26 | F, FC |
| 25 | DHST* | 15.82 | 211.0765 | C14H12O2 | 0.02 | 99.76 | F, FC |
| UPLC-QTOF-MS (hydrolyzed urine) | |||||||
| 15 | RSV* | 10.94 | 227.0714 | C14H12O3 | –1.49 | 98.09 | |
| 18 | DHRSV* | 11.35 | 229.0870 | C14H14O3 | –1.58 | 98.63 | |
| 26 | cis-RSV | 13.02 | 227.0714 | C14H12O3 | 1.38 | 97.96 | |
| 24 | LUNU* | 15.34 | 213.0921 | C14H14O2 | –1.35 | 98.86 | |
| 25 | DHST* | 15.83 | 211.0765 | C14H12O2 | –0.24 | 98.96 | |
a
U, urine; F, feces; FC, fecal in vitro culture. *Identification using authentic standards.
b
Conjugates tentatively identified (i) according to their exact molecular formula, high score (>90), low error (<5 ppm), and fragmentation pattern, and (ii) their disappearance after enzymatic hydrolysis with the simultaneous detection of the corresponding free metabolites (identified with standards).
c
Although the score was below 90, the molecular mass was consistent with a sulfate derivative, and the metabolite disappeared after sulfatase hydrolysis. RSV, trans-resveratrol; DHRSV, dihydroresveratrol; DHST, 3,4′-dihydroxy-trans-stilbene; LUNU, lunularin.