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Diindoylymethane (DIM) is a component of Indole-3-carbinol (I3C) found in members of the Brassica family. Most notably broccoli, kale, and cauliflower.
It has potent effects on estrogen metabolism and is able to keep the body relatively balanced (by preventing either drastic increases or decreases in estrogen). In small amounts, it can both inhibit the aromatase enzyme (and prevent conversion of testosterone into estrogen) and it can act on more potent forms of estrogen and convert them into less potent forms; this conversion reduces the overall effects of estrogen in the body. However, taking too much DIM at once can actually induce the aromatase enzyme and act in the opposite manner and increase estrogen synthesis.
DIM also exerts numerous anti-carcinogenic (anti-cancer) effects in the body and is one of the reasons this vegetable family is seen as healthy.
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Diindolylmethane (henceforth DIM) is the primary pharmaceutically active acid-derived metabolic of Indole-3-Carbinol (I3C) which is found in many Brassica vegetables via the mother compound glucobrassicin. Ingested glucobrassicin is catalyzed via the enzyme Myrosinase (stored in vegetables) and turns into Indole-3-Carbinol, which is rapidly digested into both DIM and various other metabolites in the human stomach via acid-mediated condensation reacitons.
Sources of Glucosinolates (in general) are listed below, with sources of Indole-3-Carbinol and DIM in bold. A source of DIM may contain less than the listed glucosinolate total:
As glucobrassicin degrades into I3C by the plant-contained enzyme Myrosinase, deactivation of this enzyme by heat-treatment (cooking) can reduce the oral bioavailability of any glucosinolate including DIM. Some bioavailability is retained, however, due to human intestines expressing Myrosinase as well.
Boiling and microwaving (750-900 watts) seem most suspect in reducing glucosinolate bioavailability; the former due to excess water sapping water-soluble bioactives from the food. Along these lines, cooking methods that utilize less water retain more glucosinolates than do those using lots of water.
Glucosinolates can have their absorption rates reduced by cooking, and low temperature steaming may be the most efficient way to preserve glucosinolate content of vegetables
DIM has been shown to active nuclear factor kappa-beta (nF-kB) signalling, caspase activation, cytochrome P450 activation (specifically CYP1A1, CYP1A2, and CYP19), DNA repair, the aryl hydrocarbon receptor (AHR) and various protein kinases.
DIM appears to be an estrogen regulatory compound, as it possesses both pro-estrogenic and anti-estrogenic mechanisms of action.
In the liver, activation of the Aryl Hydrocarbon receptor (AhR) is an area of focus when looking at estrogenic effects of DIM. Binding to the Ah receptor (in general) can cause more aromatase to be synthesized and cause greater conversion of testosterone to estroge, and DIM can bind to the Ah receptor as well as directly induce the aromatase enzyme causing it to increase. However, its binding to the AhR is weak, and coingestion of DIM alongside PCBs or Dioxins (common industrial estrogenic compounds) causes less of a spike in estrogen than isolated PCBs or Dioxins, and relatively less estrogenic activity.
When looking at the enzymes of P450 and liver detoxification, DIM appears to inherently be pro-estrogenic but may act as an antagonist in the presence of stronger estrogens and thus cause a relative decline
Beyond liver enzyme interactions, the modification of estrogen metabolites also produces an ultimate state in which more of the 2-hydroxyestrogens relative to 16a-hydroxyestrogens and 4-hydroxyestrogens results in less overall estrogenic actions in vivo. This is due to induction (activation) of the estradiol-2-hydroxylase enzyme, an enzyme that converts estrogens and estrones to their 2-hydroxylated form which is seen as chemoprotective  and in some cases anti-estrogenic while not influencing 4 and 16a-hydroxlyation, two metabolites which are genotoxic and retain estrogenic properties.
'Estrogen' is a term used to refer to a class of molecules with similar activities (sort of like how 'Androgen' is a blanket statement for many molecules), and DIM can cause a shift in estrogen ratios to cause less estrogenic effects
In regards to androgen metabolism, DIM appears to be a strong antagonist in human prostate cancer cells.
DIM shows potential synergism with Phenethyl Isothiocyanate (PEITC, derived from Gluconasturtiin and found in watercress), a compound found in Brassica vegetables alongside I3C.
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