TABLE 3
Identification of putative C-DIM metabolites using theoretical MRM(s)
Putative metabolites are listed for each C-DIM, indicating the structural position to which metabolism occurs. Metabolites were detected in several tissues, plasma and urine.
 | |||||
|---|---|---|---|---|---|
| Compound | Theoretical Metabolism | Tissue/Microsome Observed in | R1 | R2/Addition to Indole Ring | MRM(s) / Theoretical MRM(s) used to ID Putative Metabolite |
| C-DIM5 | OCH3 | — | 351.3 → 335, 116, 220 | ||
| Oxidation | U ± β-gluc; L; B | OCH3 | O | 367.3 → 132, 116 | |
| Demethylation | L; M; H; K; B | OH | — | 337.3 → 116 | |
| Demethylation and addition of glucose | U | O-glucose | — | 513.4 → 116 | |
| C-DIM7 | H | — | 321.3 → 116, 243, 204 | ||
| Oxidation | P ± β-gluc; U ± β-gluc; L; K; B | H | O | 337.3 → 132, 116 | |
| C-DIM8 | OH | — | 337.1 → 116, 220 | ||
| Addition of glucose | P; U | O-glucose | — | 513.1 → 116 | |
| Oxidation | P; U ± β-gluc; L; Micro | OH | O | 353.1 → 132, 116 | |
| Glucuronidation | U; L | O-Gluc | — | In source decay to parent MRMs with RT=1.08 min | |
| C-DIM12 | Cl | — | 355.1 → 116, 243 | ||
| Oxidation | P ± β-gluc; U + β-gluc; L; Micro; K; B; Lung | Cl | O | 371.1 → 132, 116 | |
| Dehalogenation oxidation and glucuronidation | U + β-gluc | O-Gluc | — | 337.1 → 220 |
β-gluc, β-glucuronidase treated; C-DIM, para-phenyl subsitiuted diindolylmethane; Gluc, glucuronic acid; H, heart; K, kidney; L, liver; M, muscle; Micro, liver microsome incubation; MRM, multiple reaction monitoring; P, plasma; U, urine.