Curcumin
From Wikipedia, the free encyclopedia
| 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 | Oc1ccc(cc1OC)/C=C/C(=O)CC(=O)/C=C/c2ccc(O)c(OC)c2 |
| 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) Infobox disclaimer and references |
|
Curcumin is the active ingredient of the Indian curry spice turmeric. It is a polyphenol with a molecular formula C21H20O6. Curcumin can exist in at least two tautomeric forms, keto and enol. The keto form is preferred in solid phase and the enol form in solution.
Curcumin can be 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. Indeed, when 0.2% curcumin is added to diet given to rats or mice previously given a carcinogen, it significantly reduces colon carcinogenesis (Data from sixteen scientific articles reported in the Chemoprevention Database).
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.
Little curcumin, when eaten, is absorbed. Co-supplementation with piperine (extracted from black pepper) appears to significantly increase the absorption of curcumin. It is not clear whether curcumin's beneficial effects require systemic absorption or not.
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. Carcinogenic effects are inferred from interference with the p53 tumor suppressor pathway, an important factor in human colon cancer. Carcinogenic and LD50 tests in mice and rats, however, have failed to establish a relationship between tumorogenesis and administration of curcumin in turmeric oleoresin at >98% concentrations.
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, a.k.a. vitamin E.
There is also circumstantial evidence that curcumin improves mental functions; a survey of 1010 Asian people who ate yellow curry and were between the ages of 60 and 93 showed that those who ate the sauce "once every six months" or more had higher MMSE results than those who did not. From a scientific standpoint, though, this does not show whether the curry caused it, or people who had healthy habits also tended to eat the curry, or some completely different relationship.[1]
Asian curcumin may be toxic, not for the curcumin itself, but because of heavy metal, insecticide, herbicide and fungicide content. Those looking to curcumin for its admitted good effects may get unwelcome toxic companions from so-called "natural curcumin."
[edit] References
- Kelly, M.R., J. Xu, K.E. Alexander, and G. Loo. 2001. "Disparate effects of similar phenolic phytochemicals as inhibitors of oxidative damage to cellular DNA." Mutation Research. 485: 309-318. (PMID 11585363)
- Campbell, Frederick C.; Collett, Gavin P. 2005. "Chemopreventive properties of curcumin." Future Oncology, 1(3), 405-414. (PMID 16556014)
- Ringman, John M.; Frautschy, Sally A.; Cole, Gregory M.; Masterman, Donna L.; Cummings, Jeffrey L. "A potential role of the curry spice curcumin in Alzheimer's disease." Current Alzheimer Research, 2(2), 131-136. (PMID 15974909)
- Aggarwal, Bharat B.; Kumar, Anushree; Aggarwal, Manoj S.; Shishodia, Shishir. 2005. "Curcumin derived from turmeric (Curcuma longa): A spice for all seasons." Phytopharmaceuticals in Cancer Chemoprevention, 349-387.
- Chattopadhyay, Ishita; Biswas, Kaushik; Bandyopadhyay, Uday; Banerjee, Ranajit K. 2004. "Turmeric and curcumin: biological actions and medicinal applications." Current Science', 87(1), 44-53.
- Kawanishi, S. Oikawa, S. Murata, M. 2005. "Evaluation for safety of antioxidant chemopreventive agents." Antioxidants & Redox Signaling 7(11-12), 1728-1739. (PMID 16356133)
- Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS. 1998. "Influence Of Piperine On The Pharmacokinetics Of Curcumin In Animals And Human Volunteers". Planta medica, 64(4):353-6. (PMID 9619120)
- Moos PJ, Edes K, Mullally JE, Fitzpatrick FA. 2004 "Curcumin impairs tumor suppressor p53 function in colon cancer cells". Carcinogenesis, 25(9):1611-7. (PMID 15090465)
