Indole-3-carbinol
From Wikipedia, the free encyclopedia
| Indole-3-carbinol | |
|---|---|
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| IUPAC name | 1H-indol-3-ylmethanol |
| Other names | Indole-3-carbinol, 3-Indolylcarbinol, 1H-Indole-3-methanol, 3-Hydroxymethylindole, 3-Indolemethanol, Indole-3-methanol, I3C |
| Identifiers | |
| CAS number | [700-06-1] |
| PubChem | |
| EINECS number | |
| ChEBI | |
| RTECS number | NL9483000 |
| SMILES | C1=CC=C2C(=C1)C(=CN2)CO |
| InChI | 1/C9H9NO/c11-6-7-5-10-9- 4-2-1-3-8(7)9/h1-5,10-11H,6H2 |
| Properties | |
| Molecular formula | C9H9NO |
| Molar mass | 147.18 g/mol |
| Appearance | Off-white solid |
| Melting point |
96 - 99 °C |
| Solubility in water | Partially in cold water |
| Hazards | |
| EU classification | Irritating (Xi) |
| NFPA 704 |
 0
1
0
|
| R-phrases | R36/38 |
| S-phrases | S26, S36 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Indole-3-carbinol (C9H9NO) is produced by the breakdown of the glucosinolate glucobrassicin which can be found at relatively high levels in cruciferous vegetables. Indole-3-carbinol is the subject of on-going biomedical research into its possible anticarcinogenic, antioxidant, and anti-atherogenic effects. Research on indole-3-carbinol has been conducted primarily using laboratory animals and cultured cells. Limited and inconclusive human studies have been reported. A recent review of the biomedical research literature found that, "evidence of an inverse association between cruciferous vegetable intake and breast or prostate cancer in humans is limited and inconsistent" and "larger randomized controlled trials are needed" to determine if supplemental indole-3-carbinol has health benefits[1].
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[edit] Indole-3-carbinol and cancer
Investigation of mechanisms by which consumption of indole-3-carbinol might influence cancer incidence focus on its ability to alter estrogen metabolism and other cellular effects. Controlled studies have been performed on such animals as rats, mice, and rainbow trout, introducing various controlled levels of carcinogens, and levels of Indole-3-carbinol into their daily diet. Results showed dose-related decreases in tumor susceptibility due to Indole-3-carbinol (inferred by decreases in aflatoxin-DNA binding). The first direct evidence of pure anti-initiating activity by a natural anticarcinogen (indole-3-carbinol) found in human diet was claimed by Dashwood, et al, in 1989.[2]
In 2006, Hsu et al proved that indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells.[3] 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. The G1 phase is marked by synthesis of various enzymes that are required in the next ("S") phase, including those needed for DNA replication.
It should be noted that indiscriminant overuse of indole-3-carbinol supplements in hopes of preventing cancer may be unwise, as hormone balance should be tested (via simple blood test) before regular consumption. Such caution is advised due to its effect on estrogen levels (estrogen has a significant impact on brain function).[4][5]
[edit] Dietary sources
Indole-3-carbinol occurs naturally in cruciferous vegetables such as cabbage, broccoli, brussels sprouts, and kale. It is also widely available in supplement form.
[edit] References
- Michnovicz JJ, Bradlow HL. Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990; 82:947-950. Entrez PubMed 2342128
- Morgan DO. (2007) The Cell Cycle: Principles of Control. New Science Press: London
[edit] Footnotes
- ^ Dashwood, RH, et al (2007). "Cruciferous vegetables and human cancer risk: epidemiologic evidence and mechanistic basis.". Pharmacological research 55 (3): 224–236. doi:.Entrez PubMed 17317210
- ^ Dashwood, RH, et al (1989). "Quantitative inter-relationships between aflatoxin B1 carcinogen dose, indole-3-carbinol anti-carcinogen dose, target organ DNA adduction and final tumor response.". Carcinogenesis, Jan; 10 (1): 175–181. doi:. PMID 2491968.Entrez PubMed 2491968
- ^ Hsu, JC, et al (2006). "Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells requires the induced production of activated p53 tumor suppressor protein.". Biochem Pharmacol., Dec 15; 72 (12): 1714–23. doi:.Entrez PubMed 16970927
- ^ Culmsee, Carsten (1999). "Neuroprotection by Estrogens in a Mouse Model of Focal Cerebral Ischemia and in Cultured Neurons: Evidence for a Receptor-Independent Antioxidative Mechanism". Journal of Cerebral Blood Flow & Metabolism 19: 1263–1269. doi:.
- ^ Society for Neuroscience, "Estrogen's Influence on the Brain".
