Indole-3-carbinol, effect

Se-enriched broccoli was not more effective (Table 1) than enriched garlic (3) in reducing the number of tumors this Ending proves that the combination of sulforaphane, indole carbinol, and chlorophyll with Se did not provide additional protection against mammary tumors. (Adapted from Finley... 

Tanaka T, Mori Y, Morishita Y, Hara A, Ohno T, Kojinna T and Mori H. 1990. Inhibitory effect of sinigrin and indole-3-carbinol on diethylenitrosamine-induced hepatocarcinogenesis in male AC/N rats. Carcinogenesis 11 1403—1406. 

Serum sex hormones effect. DION (300 mg androstenedione, 150 mg dehydro-epiandrosterone, 540 mg saw palmetto, 300 mg indole-3-carbinol, 625 mg chrysin, 750 mg Tribulus terrestris), administered daily to healthy 30- to 59-year-old men for 28 days, produced no change in serum concentrations of total T and PSA. DION increased the concentrations of serum androstenedione (342%), free T (38%), DHT (71%), and estradiol (103%). Serum high-density lipoprotein (HDL) cholesterol concentrations were reduced by 5 mg/dL in DION (p < 0.05). Increases in serum free T (r = 0.01), androstenedione (r = 0.01), DHT (r = 0.03), or estradiol (r = 0.07) concentrations in DION were not related to age. The ingestion of androstenedione combined with herbal products increased serum-free T concentrations in older men, but herbal products did not prevent the conversion of... 

Wilker C, Johnson L, Safe S. 1996. Effects of developmental exposure to indole-3-carbinol or 2,3,7,8-tetrachlorodibenzo-p-dioxin on reproductive potential of male rat offspring. Toxicol Appl Pharmacol 141 68-75. 

Both the silyl derivative (59) and the alcohol (60) may be used as sources of the iminium salt (61) in reactions with a wide variety of nucleophiles. In practice, it was found feasible to use Grignard reagents for reaction with the silyl derivative, while TiC was effective in promoting attack on the carbinol amine by weaker nucleophiles. The process is shown in Scheme 24 using the addition of indole as an example. 

An enzyme involved in cell cycle control has been identified as the target of a compound supplied by broccoli, cabbage, and Brussels sprouts. One of the glucosinolates of these foods is the source of a chemical called indole 3-carbinol. Indole-3-carbinol enters the cell and influences the activity of a spixiat protein kinase that is used to control the cell cycle. The chemical prevents the synthesis of the enzyme, and thus reduces its activity. The action of this protein kinase (cyclin-dependent protein kinase 6) normally functions to make the cell embark on the G phase of the cell cycle, and thus to stimulate progression through the cell cycle. The chronic decrease in activity of this protein kinase serves to prevent cell division, but also prevents spontaneous cancers. The effect of mdoJe-3-carbinol has been shown to occur in cultured cells, as well as in animals (Cover ef o/ 1998). 

Dolby and Biere (252, 253) adopted a quite different tactic to produce these systems. The key step is the trapping of a Vilsmeier salt with sodium borohydride. All the functionality required to effect the condensation reactions is built into a 2-pyridone derivative 612. This compound is produced by the route outlined in Scheme 38. Treatment of 612 with indole in the presence of phosphorus oxychloride gives a Vilsmeier salt, which is reduced with sodium borohydride to the piperidylindole 613. Hydrolysis of the ester group and cyclization with polyphosphoric acid gave a mixture consisting mainly of epidasycarpidone (608) (54% yield) together with some 607 (15% yield). The 608 was converted to the carbinol 614 with methyllithium and dehydrated to 611 with alumina. 

Higdon JV, Delage B, Williams DE, Dash wood RH (2007) Cruciferous vegetables and hiunan cancer risk epidemiologic evidence and mechanistic basis. Pharm Res 55 224-236 Ashok BT, Chen Y, Liu X, Bradlow HL, Mittelman A, Tiwari RK (2001) Abrogation of estrogen-mediated cellular and biochemical effects by indole-3-carbinol. Nutr Cancer 41 180-187... 

A similar substituent effect operates in the reaction of indole with diethyl ketomalonate conducted by microwave irradiation oti montmorillonite K-10 clay [125]. Indole, its 1-methyl and 2-methyl derivatives, along with C-ring analogs, gave mixtures of both the 3-carbinol and te-indol-3-yl products. 

Blum, C.A. et al., p-Catenin mutation in rat colon tumors initiated by 1,2-dimethyl-hydrazine and 2-amino-3-methylimidazo[4,5-f quinoUne, and the effect of post-initiation treatment with chlorophyUin and indole-3-carbinol. Carcinogenesis (London), 22, 315, 2001. 

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