Research Area: Metabolic Disease Biological Activity: Indole-3-carbinol is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables. Dose-related decreases in tumor susceptibility due to Indole-3-carbinol (inferred by decreases in aflatoxin-DNA binding). Indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells. This is significant in the prevention and treatment of cancer, as the G1 phase of cell growth occurs early in the cell lifecycle, and, for most cells, is the major period of cell cycle during its lifespan. [1][2]
Biochem/physiol Actions Inhibits cancinogenesis at the initiation stage. Has be shown to inhibit carcinogenesis in several animal species, but it enhances tumor incidence if administered at a post-initiation stage. Found in cruciferous vegetables. Other Notes Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I7256.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
An indolyl alcohol carrying a hydroxymethyl group at position 3. It is a constituent of the cruciferous vegetables and had anticancer activity.
References
PubChem Literature
From Data Sources
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• On treatment with acids, is converted to a stabilized cation 3-methylene-3H-indolium, which can undergo further reaction to give diindol-3-ylmethane. Moody's group have demonstrated a formal [3+2] cycloaddition of the cation to a variety of alkenes to give cyclopenta[b]indoles: J. Chem. Soc., Perkin 1, 1127 (1995):