Table 3. 1H NMR Analyses of Urolithins Dissolved in AcN-d3 and DMSO-d6 Compared with the Estimated Values in ChemDraw Using DMSO-d6.
| metabolite | H-1 | H-2 | H-4 | H-7 | H-8 | H-9 | H-10 |
|---|---|---|---|---|---|---|---|
| AcN-d3 | |||||||
| Uro-D 3,4,8,9-OH | d7.41, J = 8.8 Hz | d6.85, J = 8.8 Hz | s7.60 | s7.48 | |||
| Uro-C 3,8,9-OH | d7.865 J = 9,1 Hz | dd6.83 J = 2.7, 9.1 Hz | d6.77 J = 2.7 Hz | s7.60 | s7.48 | ||
| Uro-M7 3,8,10-OH | d8.75 J = 9 Hz | dd6.81 J = 2,4, 9 H | d6.76 J = 2.4 Hz | d7.27 J = 2.4 | d6.84 J = 2.4 | ||
| Uro-A 3,8-OH | d8.1 J = 8.8 Hz | dd6.82 J = 2.7, 8.7 Hz | d6.79 J = 2.7 Hz | d7.60, J = 2.7 Hz | dd7.345 J = 2,7 Hz; 8.7 Hz | d7.945 J = 8.8 Hz | |
| IsoUro-A 3,9-OH | d7.94, J = 8.6 Hz | dd6.88 J = 2.3, 8.6 Hz | d6.79 J = 2.3 Hz | 8.13 J = 8.6 Hz | dd7.02, J = 2.3, 8.6 Hz | d7.47 J = 2.3 Hz | |
| Uro-G 3,4,8-OH | d7.49 J = 8.75 | d6.87 J = 8.70 | d7.61 J = 2.7 | dd7.34 J = 2,76, 8.75 | d8.01 J = 8.8 Hz | ||
| DMSO-d6 | |||||||
| Uro-D 3,4,8,9-OH | d7.29, J = 8.8 Hz | d6.77, J = 8.8 Hz | s7.48 | s7.39 | |||
| Uro-C 3,8,9-OH | d7.83 J = 9,1 Hz | dd6.77 J = 2.7,9.1 Hz | d6.67 J = 2.7 Hz | s7.47 | s7.42 | ||
| Uro-M7 3,8,10-OH | d8.73 J = 9 Hz | dd6.74 J = 2.4, 9 H | d6.68 J = 2.4 Hz | d7.11 J = 2.4 | d6.84 J = 2.4 | ||
| Uro-A 3,8-OH | d8.10 J = 8.8 Hz | dd6.79 J = 2.7, 8.7 Hz | d6.71 J = 2.7 Hz | d7.49 J = 2.7 Hz | dd7.31 J = 2.7 Hz; 8.7 Hz | d8.01 J = 8.8 Hz | |
| IsoUro-A 3,9-OH | d7.96 J = 8.6 Hz | dd6.79 J = 2.3, 8.6 Hz | d6.69 J = 2.3 Hz | d8.02 J = 8.6 Hz | dd6.95, J = 2.3, 8.6 Hz | d7.42 J = 2.3 Hz | |
| Uro-G 3,4,8-OH | d7.48 J = 8.75 | d6.79 J = 8.70 | d7.50 J = 2.7 | dd7.31 J = 2.76, 8.75 | D8.08 J = 8.8 Hz | ||
| ChemDraw estimated (DMSO-d6) | |||||||
| Uro-D 3,4,8,9-OH | d7.23, J = 8.8 Hz | d6.73, J = 8.8 Hz | s7.55 | s7.12 | |||
| Uro-C 3,8,9-OH | d7.67 J = 9.1 Hz | dd6.76 J = 2.7,9.1 Hz | d6.88 J = 2.7 Hz | s7.55 | s7.12 | ||
| Uro-M7 3,8,10-OH | D7.67 J = 9 Hz | dd6.76 J = 2.4, 9 H | d6.85 J = 2.4 Hz | d7.28 J = 2.4 | d6.58 J = 2.4 | ||
| Uro-A 3,8-OH | D7.67 J = 8.8 Hz | dd6.76 J = 2.7, 8.7 Hz | d6.88 J = 2.7 Hz | d7.72 J = 2.7 Hz | dd7.11 J = 2.7 Hz; 8.7 Hz | d7.75 J = 8.8 Hz | |
| IsoUro-A 3,9-OH | d7.67 J = 8.6 Hz | dd6.76 J = 2.3, 8.6 Hz | d6.88 J = 2.3 Hz | d8.20 J = 8.6 Hz | dd6.95, J = 2.3, 8.6 Hz | d7.29 J = 2.3 Hz | |
| Uro-G 3,4,8-OH | d7.23 J = 8.75 | d6.73 J = 8.70 | d7.72 J = 2.7 | dd7.11 J = 2.76, 8.75 | D7.75 J = 8.8 Hz | ||
| IsoUro-G 3,4,9-OH | d7.23 J = 8.75 | d6.73 J = 8.70 | D8.20 J = 2.7 | dd6.95 J = 2.76, 8.75 | D7.29 J = 2.7 Hz | ||