Curcumin
Encyclopedia : C : CU : CUR : Curcumin
| Curcumin | |
|---|---|
 Keto Form  Enol Form | |
| General | |
| Systematic name | (1E,6E)-1,7-bis(4-hydroxy- 3-methoxyphenyl)-1,6- heptadiene-3,5-dione |
| Other names | curcumin diferuloylmethane C.I. 75300 Natural Yellow 3 |
| Molecular formula | C21H20O6 |
| SMILES | ? |
| Molar mass | 368.38 g/mol |
| Appearance | ? |
| CAS number | [458-37-7] |
| Properties | |
| Density and phase | ? g/cm3, ? |
| Solubility in water | ? g/100 ml (? °C) |
| Melting point | ? °C (? K) |
| Boiling point | ? °C (? K) |
| Acidity (pKa) | ? |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | ? |
| NFPA 704 | |
| Flash point | ? °C |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Related compounds | |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) [Chemical infoboxInfobox disclaimer and references] | |
Curcumin can used for boron quantification in the so called curcumin method. It reacts with boric acid forming a red colored compound, known as rosocyanine.
Curcumin is known for its antitumor, antioxidant, anti-amyloid and anti-inflammatory properties. Anti-inflammatory action may be due to leukotriene inhibition.
Curcumin acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage. Curcuminoids induce glutathione S-transferase and are potent inhibitors of cytochrome P450.
For the last few decades, extensive work has been done to establish the biological activities and pharmacological actions of curcumin. Its anticancer effects stem from its ability to induce apoptosis in cancer cells without cytotoxic effects on healthy cells. Curcumin can interfere with the activity of the transcription factor NF-κB ( NF-kB ), which is often highly overexpressed in many cancer cells, according to a talk given by Dr. Dennis Liotta at Davidson College in January 2006.
A 2004 UCLA-Veterans Affairs study involving genetically altered mice suggests that curcumin might inhibit the accumulation of destructive beta-amyloid in the brains of Alzheimer's disease patients and also break up existing plaques associated with the disease. It was published that curcumin inhibits cyclooxygenase-2 (COX-2) as well as lipoxygenase (LOX), two enzymes involved in inflammation.
It is used as a food coloring (it is what colors curry yellow). As a food additive, its E number is E100.
However, as pointed out by Kawanishi et al. (2005) curcumin is a "double-edged sword" having both anti-cancer and carcinogenic effects.
Curcumin has devastating effects on healthy human cells. A study done by Kelly et al. (2001) in the journal of Mutation Research, proves that curcumin has prooxidant activity based on its effects on the DNA pattern achieved by alkaline gel electrophoresis. However, the undesired effects of curcumin can be suppressed by the lipophilic antioxidant, α-tocopherol.
References
Disparate effects of similar phenolic phytochemicals as inhibitors of oxidative damage to cellular DNA. 2001. Kelly, M.R., J. Xu, K.E. Alexander, and G. Loo. Mutation Research. 485: 309-318.
Chemopreventive properties of curcumin. Campbell, Frederick C.; Collett, Gavin P. Future Oncology (2005), 1(3), 405-414.
A potential role of the curry spice curcumin in Alzheimer's disease. Ringman, John M.; Frautschy, Sally A.; Cole, Gregory M.; Masterman, Donna L.; Cummings, Jeffrey L. Current Alzheimer Research (2005), 2(2), 131-136.
Curcumin derived from turmeric (Curcuma longa): A spice for all seasons. Aggarwal, Bharat B.; Kumar, Anushree; Aggarwal, Manoj S.; Shishodia, Shishir. Phytopharmaceuticals in Cancer Chemoprevention (2005), 349-387.
Turmeric and curcumin: biological actions and medicinal applications. Chattopadhyay, Ishita; Biswas, Kaushik; Bandyopadhyay, Uday; Banerjee, Ranajit K. Current Science (2004), 87(1), 44-53.
Evaluation for safety of antioxidant chemopreventive agents. Kawanishi, S. Oikawa, S. Murata, M. Antioxidants & Redox Signaling (2005) 7(11-12), 1728-1739.
External links
- [Journal of Biological Chemistry primary research article: Curcumin Inhibits Formation of Amyloidβ Oligomers and Fibrils, Binds Plaques, and Reduces Amyloid in Vivo]
- [Sloan-Kettering Herbal Guide]
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