![]() The highest concentration of DIM is found in the liver. 25 After ingestion, DIM concentrations in different tissues vary. This is evidenced by a 6-fold increase in DIM concentrations in boiled cabbage compared with uncooked cabbage. ![]() 24ĭIM concentrations rise during cooking, 25 in part because of the thermal activation of myrosinase. In experimental models, I3C has been shown to self-condense to produce DIM at a ratio of 2:1. 23 As the conversion is pH dependent, exposure to stomach acid is necessary for the conversion of I3C into DIM 22 and other acid condensation products. In fact, a pH-dependent, acid-catalyzed condensation rapidly converts I3C to oligomers that include DIM, which is the major indole bioactive compound, accounting for an estimated 60% of the I3C end product. Included in the various indoles is indole-3-carbinol (I3C), which is a relatively unstable compound. Enzymatic breakdown of glucobrassicin by the plant-derived enzyme myrosinase during plant storage, preparation, and/or chewing 22 yields various indoles. Glucobrassicin is the most abundant glucosinolate in vegetables within the family Brassicaceae. Chemopreventive roles of phytochemicals have been described previously, but only limited data about the specific types of vegetables contributing to the overall glucosinolate intake in the United States are available. The average consumption of glucosinolates from vegetable sources is nonspecific and approximated, 21 and estimates for US intakes are generally lower than those for European and Asian nations. 12 US dietary intake estimates for cruciferous vegetables are low 10 and are currently not classified by specific vegetable type, limiting the availability of intake estimates of glucosinolates. The average human consumption of glucosinolates from food sources is estimated at 0.5μM/kg/d. 15–19 Major glucosinolates are glucobrassicin and glucoraphanin, the latter of which is a derivative of isothiocyanates, 20 including sulforaphane. 26Ĭruciferous vegetables contain bioactive precursor compounds known as glucosinolates ( Table 1). Concentrations are time dependent, as demonstrated in a mouse model after supplementation with pure crystalline DIM at a dosage of 250 mg/kg. The concentration of diindolylmethane is highest in liver, followed by lung, kidney, and heart and, to a lesser extent, brain and plasma. Diindolylmethane is an end product of the pH-dependent metabolism of indole-3-carbinol. Metabolism of diindolylmethane from cruciferous vegetables. The purpose of this review is to describe the metabolism of DIM, the mechanisms of action of DIM against breast cancer, and the current state of human observational and intervention trials with DIM to introduce the next steps toward advancing understanding and developing guidance on DIM intake for public health. DIM is one of the best-characterized and most abundant bioactive compounds found in commonly consumed crucifers. 12 The argument for the focus on one bioactive constituent in particular, 3,3′-diindolylmethane (DIM), as a relevant bioactive food compound in breast cancer chemoprevention is based on the extensive evaluation of DIM in relation to its chemopreventive potential, particularly for breast cancer. In fact, the chemopreventive roles of multiple phytochemicals found in crucifers have been described previously. ![]() Discrepancies in current findings are thought to be explained in part by variances in exposure to multiple bioactive constituents found in this unique classification of vegetables. Importantly, this review also focuses on current evidence from human observational and intervention trials that have contributed to a greater understanding of exposure estimates that will inform recommendations for DIM intake.Ĭruciferous vegetables have been shown to be protective against breast cancer in some, 1–8 but not all, 9–11 epidemiological studies. This review describes current evidence related to the metabolism and mechanisms of DIM involved in the prevention of breast cancer. Bioactive DIM has demonstrated chemopreventive activity in all stages of breast cancer carcinogenesis. Further, this body of evidence is largely supported by observational studies. Research of the cancer-preventive activity of DIM has yielded basic mechanistic, animal, and human trial data. This review focuses on 3,3′-diindolylmethane (DIM), the major bioactive indole in crucifers. The role of bioactive compounds of food origin, including those found in cruciferous vegetables, is an active area of research in cancer chemoprevention. Diet is a modifiable factor associated with the risk of several cancers, with convincing evidence showing a link between diet and breast cancer.
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