Indole-3-carbinol

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Indole-3-carbinol[1]
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 YesY
PubChem 3712
ChemSpider 3581 YesY
EC number 211-836-2
ChEBI CHEBI:24814 YesY
ChEMBL CHEMBL155625 YesY
RTECS number NL9483000
Jmol-3D images Image 1
Properties
Molecular formula C9H9NO
Molar mass 147.17 g mol−1
Appearance Off-white solid
Melting point 96 to 99 °C; 205 to 210 °F; 369 to 372 K
Solubility in water Partially in cold water
Hazards
EU classification Irritating (Xi)
R-phrases R36/38
S-phrases S26, S36
NFPA 704
0
1
0
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Indole-3-carbinol (C9H9NO) is produced by the breakdown of the glucosinolate glucobrassicin, which can be found at relatively high levels in cruciferous vegetables such as broccoli, cabbage, cauliflower, brussels sprouts, collard greens and kale. I3C is also available in a dietary supplement.[2] Indole-3-carbinol is the subject of on-going Biomedical research into its possible anticarcinogenic,[3] 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.[4]

Indole-3-carbinol and cancer

Investigation of mechanisms by which consumption of indole-3-carbinol might influence cancer incidence focuses 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.[5]

Indole-3-carbinol induces a G1 growth arrest of human reproductive cancer cells.[6] This is potentially relevant to the prevention and treatment of cancer, as the G1 phase of cell growth occurs early in the cell life cycle, 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.

Overuse of indole-3-carbinol supplements in the hope of preventing cancer may be unwise, as the 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).[7][8]

It promotes liver cancer in trout when it is combined with aflatoxin B1 and demotes metastasis.[2]

Systemic lupus erythematosus

Indole-3-carbinol can shift estrogen metabolism towards less estrogenic metabolites. Systemic lupus erythematosus (SLE, or lupus), an autoimmune disease, is associated with estrogen. In a study using mice bred to develop lupus, indole-3-carbinol was fed to one group while another group was fed a standard mouse diet; the group fed the indole-3-carbinol diet lived longer and had fewer signs of disease.[9]

Another study of lupus prone mice with indole-3-carbinol defined the mechanism for the improvement of their disease to be due to sequential blocks in the development of B and T cells of these mice. The maturation arrests resulted in a fall in autoantibody production, thought to be a crucial component of lupus causation. In addition, I3C supplementation of the disease prone mice led to a normalization of their T cell function.[10]

Women with lupus can manifest a metabolic response to indole-3-carbinol and might also benefit from its antiestrogenic effects. Clinical trials are currently underway to determine the efficacy of treating human patients suffering from lupus with indole-3-carbinol.

Effect in recurrent respiratory papillomatosis

There is evidence suggesting that indole-3-carbinol may have an effect on human papilloma virus infected cells in both pediatrics and adult patients.[11][12] Research is ongoing.

References

  1. ↑ Data at chemblink.com
  2. ↑ 2.0 2.1 Tilton, S. C.; Hendricks, J. D.; Orner, G. A.; Pereira, C. B.; Bailey, G. S.; Williams, D. E. (2007). "Gene expression analysis during tumor enhancement by the dietary phytochemical, 3,3'-diindolylmethane, in rainbow trout". Carcinogenesis 28 (7): 1589–1598. doi:10.1093/carcin/bgm017. PMID 17272308. 
  3. ↑ Park, N. I.; Kim, J. K.; Park, W. T.; Cho, J. W.; Lim, Y. P.; Park, S. U. (2010). "An efficient protocol for genetic transformation of watercress (Nasturtium officinale) using Agrobacterium rhizogenes". Molecular Biology Reports 38 (8): 4947–4953. doi:10.1007/s11033-010-0638-5. PMID 21161399. 
  4. ↑ Higdon, J; Delage, B; Williams, D; Dashwood, R (2007). "Cruciferous vegetables and human cancer risk: Epidemiologic evidence and mechanistic basis". Pharmacological Research 55 (3): 224–36. doi:10.1016/j.phrs.2007.01.009. PMC 2737735. PMID 17317210. 
  5. ↑ Dashwood, Rod H.; Arbogast, D.N.; Fong, A.T.; Pereira, C.; Hendricks, J.D.; Bailey, G.S. (1989). "Quantitative inter-relationships between aflatoxin B1 carcinogen dose, indole-3-carbinol anti-carcinogen dose, target organ DNA adduction and final tumor response". Carcinogenesis 10 (1): 175–81. doi:10.1093/carcin/10.1.175. PMID 2491968. 
  6. ↑ Hsu, J; Dev, A; Wing, A; Brew, C; Bjeldanes, L; Firestone, G (2006). "Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells requires the induced production of activated p53 tumor suppressor protein". Biochemical Pharmacology 72 (12): 1714–23. doi:10.1016/j.bcp.2006.08.012. PMID 16970927. 
  7. ↑ Culmsee, Carsten; Vedder, Helmut; Ravati, Alexander; Junker, Vera; Otto, D??rte; Ahlemeyer, Barbara; Krieg, J??Rgen-Christian; Krieglstein, Josef (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: 1263. doi:10.1097/00004647-199911000-00011. 
  8. ↑ "Estrogen's Influence on the Brain". Society for Neuroscience. 
  9. ↑ Auborn, KJ; Qi, M; Yan, XJ; Teichberg, S; Chen, D; Madaio, MP; Chiorazzi, N (2003). "Lifespan is prolonged in autoimmune-prone (NZB/NZW) F1 mice fed a diet supplemented with indole-3-carbinol". The Journal of nutrition 133 (11): 3610–3. PMID 14608082. 
  10. ↑ Yan, Xiao-jie; Qi, Mei; Telusma, Gloria; Yancopoulos, Sophia; Madaio, Michael; Satoh, Minoru; Reeves, Westley H.; Teichberg, Saul et al. (2009). "Indole-3-carbinol improves survival in lupus-prone mice by inducing tandem B- and T-cell differentiation blockades". Clinical Immunology 131 (3): 481–94. doi:10.1016/j.clim.2009.01.013. PMID 19278904. 
  11. ↑ Rosen, Clark A.; Bryson, Paul C. (2004). "Indole-3-Carbinol for recurrent respiratory papillomatosis: Long-term results". Journal of Voice 18 (2): 248–53. doi:10.1016/j.jvoice.2003.05.005. PMID 15193659. 
  12. ↑ Rosen, Clark A.; Woodson, Gayle E.; Thompson, Jerome W.; Hengesteg, Arne P.; Bradlow, H.Leon (1998). "Preliminary results of the use of indole-3-carbinol for recurrent respiratory papillomatosis". Otolaryngology - Head and Neck Surgery 118 (6): 810–5. doi:10.1016/S0194-5998(98)70274-8. PMID 9627242. 

Further reading

  • Michnovicz, J. J.; Bradlow, H. L. (1990). "Induction of Estradiol Metabolism by Dietary Indole-3-carbinol in Humans". JNCI Journal of the National Cancer Institute 82 (11): 947. doi:10.1093/jnci/82.11.947. 
  • Morgan, David Owen (2007). The Cell Cycle: Principles of Control. London: New Science Press. ISBN 978-0-87893-508-6. 

External links

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