Curcumin
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| 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 | Bright Yellow to Orange powder |
| CAS number | [458-37-7] |
| Properties | |
| Density and phase | ? g/cm³, ? |
| Solubility in water | ? g/100 ml (? °C) |
| Melting point | 183°C (361 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 principal curcuminoid of the Indian curry spice turmeric. The curcuminoids are polyphenols and are responsible for the yellow color of turmeric. Curcumin can exist in at least two tautomeric forms, keto and enol. The enol form is more energetically stable in the solid phase and in solution[1]
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.
Since curcumin is brightly colored, it may be used as a food coloring. As a food additive, its E number is E100.
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[edit] Potential medical uses
Curcumin is known for its antitumor, antioxidant, anti-amyloid and anti-inflammatory properties. Anti-inflammatory properties may be due to inhibition of eicosanoid biosynthesis.[2]
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, which has been linked to a number of inflammatory diseases such as cancer.[3] 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.[4]
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.[5] 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.
Little curcumin, when eaten, is absorbed-- 2 grams of curcumin alone resulted in undetectable to very low serum levels.[6] Co-supplementation with 20 mg of piperine (extracted from black pepper) significantly increased the absorption of curcumin by 2000%. However, due to its effects on drug metabolism, piperine should be taken cautiously (if at all) by individuals taking other medications. Some benefits of curcumin, such as the potential protection from colon cancer, may not require systemic absorption.
[edit] Risks
However, as pointed out by Kawanishi et al. (2005) curcumin is a "double-edged sword" having both anti-cancer and carcinogenic effects.[7] Carcinogenic effects are inferred from interference with the p53 tumor suppressor pathway, an important factor in human colon cancer.[8] 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.[9] This may prove curcumin to be good in some cases as it helps activate p53. When a cell is inhibatited by cancer then the level concentrations in p53 gets higher which helps the cell defend from the cancer. Curcumin can help higher levels of p53 so it goes in defensive system more quickly, but it may also prove faulty as it can keep p53 levels down, therefore preventing the cell from going into a defensive mechanisim. Curcumin only does this with certain diseases.
[edit] References
- ^ Kolev T.M., et at, DFT and Experimental Studies of the Structure and Vibrational Spectra of Curcumin, International Journal of Quantum Chemistry, 102, 6, (2005)
- ^ Srivastava KC, Bordia A, Verma SK. Curcumin, a major component of food spice turmeric (Curcuma longa) inhibits aggregation and alters eicosanoid metabolism in human blood platelets. Prostaglandins Leukot Essent Fatty Acids. 1995 Apr;52(4):223-7. PMID 7784468.
- ^ Aggarwal BB, Shishodia S. Suppression of the nuclear factor-kappaB activation pathway by spice-derived phytochemicals: reasoning for seasoning. Ann N Y Acad Sci. 2004 Dec;1030:434-41. PMID 15659827.
- ^ Yang F, Lim GP, Begum AN, Ubeda OJ, Simmons MR, Ambegaokar SS, Chen PP, Kayed R, Glabe CG, Frautschy SA, Cole GM. Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J Biol Chem. 2005 Feb 18;280(7):5892-901. Epub 2004 Dec 7. PMID 15590663.
- ^ Ng TP, Chiam PC, Lee T, Chua HC, Lim L, Kua EH. Curry consumption and cognitive function in the elderly. Am J Epidemiol. 2006 Nov 1;164(9):898-906. Epub 2006 Jul 26. PMID 16870699.
- ^ Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PS. Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers. Planta Med. 1998 May;64(4):353-6. PMID 9619120.
- ^ Kawanishi, S. Oikawa, S. Murata, M. 2005. "Evaluation for safety of antioxidant chemopreventive agents." Antioxidants & Redox Signaling 7(11-12), 1728-1739. (PMID 16356133)
- ^ 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.
- ^ Lois Swirsky Gold. Turmeric (>98% curcurmin). Carcinogenic Potency Database Project. Last updated 3 Apr 2006. Last accessed 4 Jan 2007. [1]
- 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.
