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Curcumin

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Curcumin is the principal curcuminoid of the Indian curry spice turmeric, the other two curcuminoids being demethoxycurcumin and Bis-demethoxycurcumin.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] It is also hepatoprotective.[2]

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.

Chemistry

Curcumin incorporates several functional groups. The aromatic ring systems, which are polyphenols are connected by two α,β-unsaturated carbonyl groups. The two carbonyl groups form a diketone. The diketone form stable enols or are easily deprotonated and form enolates, while the α,β-unsaturated carbonyl is a good Michael acceptor and undergoes nucleophilic addition.

Potential medical uses

Curcumin is known for its antitumor,[3][4] antioxidant, antiarthritic, anti-amyloid and anti-inflammatory properties.[5] Anti-inflammatory properties may be due to inhibition of eicosanoid biosynthesis.[6] In addition it may be effective in treating malaria, prevention of cervical cancer, and may interefere with the replication of the HIV virus.[7] In HIV, it appears to act by interfering with P300/CREB-binding protein (CBP) of its reverse transcriptase.

A 2008 study at Michigan State University showed that low concentrations of curcumin interfere with Herpes simplex virus-1 (HSV-1) replication.[8] The same study showed that curcumin inhibited the recruitment of RNA polymerase II to viral DNA, thus inhibiting the transcription of the viral DNA.[8] This effect was shown to be independent of effect on histone acetyltransferase activities of p300/CBP.[8] A previous (1999) study performed at University of Cincinnati indicated that curcumin is significantly associated with protection from infection by HSV-2 in animal models of intravaginal infections.[9]

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.[10] 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 2007 report indicates that curcumin may suppress MDM2, an oncogene involved in mechanisms of malignant tumor formation.[11]

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.[12]

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.[13] 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.[14] Much of it is excreted through glucuronidation. Co-supplementation with 20 mg of piperine (extracted from black pepper) significantly increased the absorption of curcumin by 2000%[14]. 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. Alternatively, dissolving curcumin in hot water prior to ingestion, or in warm oily liquids, appears to increase bioavailability.

Recently, a polymeric nanoparticle encapsulated formulation of curcumin ("nanocurcumin"[15]) has been synthesized which has the potential to bypass many of the shortcomings associated with free curcumin, such as poor solubility and poor systemic bioavailability. Nanocurcumin particles have a size of less than 100 nanometers on average, and demonstrate comparable to superior efficacy compared to free curcumin in human cancer cell line models.[15] Other researchers have developed a number of other curcumin analogs that appear to have greater bioavailability, but these analogs have not been tested broadly, either in vitro or in vivo, for medicinal purposes.

Risks

Kawanishi et al. (2005) remarked that curcumin is a "double-edged sword" having both anti-cancer and carcinogenic effects.[16] Carcinogenic effects are inferred from interference with the p53 tumor suppressor pathway, an important factor in human colon cancer.[17] 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.[18] This may prove curcumin medicinally useful as it helps activate p53[citation needed]. When a cell is inhibited by cancer the concentrations of p53 increase, helping cells defend against cancer mechanisms[citation needed]. But it may also suppress p53 levels, preventing cells from initiating defensive mechanisms, a response seen only in certain diseases [citation needed].

References

  1. ^ Kolev, Tsonko M. (2005). "DFT and Experimental Studies of the Structure and Vibrational Spectra of Curcumin". International Journal of Quantum Chemistry. 102 (6). Wiley Periodicals: 1069–79. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  2. ^ Marotta, F. (October 2003). "Hepatoprotective effect of a curcumin/absinthium compound in experimental severe liver injury". Chinese Journal of Digestive Diseases. 4 (3). Blackwell Publishing: 122–7. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  3. ^ Aggarwal, BB. (May 2006). "Molecular targets of dietary agents for prevention and therapy of cancer". Biochemical Pharmacology. 71 (10). Elsevier: 1397–421. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  4. ^ Choi, Hyunsung (July 2006). "Curcumin Inhibits Hypoxia-Inducible Factor-1 by Degrading Aryl Hydrocarbon Receptor Nuclear Translocator: A Mechanism of Tumor Growth Inhibition". Molecular Pharmacology. 70. American Society for Pharmacology and Experimental Therapeutics: 1664–71. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  5. ^ Stix, Gary (February 2007). "Spice Healer". Scientific American.
  6. ^ Srivastava, KC (April 1995). "Curcumin, a major component of the food spice turmeric (Curcuma longa), inhibits aggregation and alters eicosanoid metabolism in human blood platelets". Prostaglandins Leukot Essent Fatty Acids. 52 (4): 223–7. PMID 7784468. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  7. ^ Padma, TV (2005-03-11). "Turmeric can combat malaria, cancer virus and HIV". SciDev.net.
  8. ^ a b c Kutluay SB, Doroghazi J, Roemer ME, Triezenberg SJ (January 2008). "Curcumin inhibits herpes simplex virus immediate-early gene expression by a mechanism independent of p300/CBP histone acetyltransferase activity". Virology. doi:10.1016/j.virol.2007.11.028. PMID 18191976.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ Bourne KZ, Bourne N, Reising SF, Stanberry LR (1999 Jul). "Plant products as topical microbicide candidates: assessment of in vitro and in vivo activity against herpes simplex virus type 2". Antiviral research. 42 (3): 219–26. PMID 10443534. {{cite journal}}: Check date values in: |date= (help)CS1 maint: multiple names: authors list (link)
  10. ^ 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.
  11. ^ "Curcumin's anti-cancer mechanism proposed". nutraingredients-usa.com. 2007-04-13.
  12. ^ Yang, F (February 2005). "Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo". Journal of Biological Chemistry. 280 (7). American Society for Biochemistry and Molecular Biology: 5892–901. PMID 15590663. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  13. ^ Ng TP; Chiam PC; Lee T; Chua HC; Lim L; Kua EH (November 2006). "Curry consumption and cognitive function in the elderly". American Journal of Epidemiology. 164 (9). Oxford University Press: 898–906. PMID 16870699.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  14. ^ a b Shoba G; Joy D; Joseph T; Majeed M; Rajendran R; Srinivas PS (May 1998). "Influence of piperine on the pharmacokinetics of curcumin in animals and human volunteers". Planta Med. 64 (4): 353–6. PMID 9619120.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  15. ^ a b Bisht (2007). "Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy". Journal of Nanobiotechnology. 5 (3). BioMed Central. PMID 17439648. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help); Unknown parameter |irst= ignored (help)
  16. ^ Kawanishi, S; Oikawa, S; Murata, M; (2005). "Evaluation for safety of antioxidant chemopreventive agents". Antioxidants & Redox Signaling. 7 (11–12): 1728–39. PMID 16356133.{{cite journal}}: CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  17. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  18. ^ Lois Swirsky Gold. Turmeric (>98% curcurmin). Carcinogenic Potency Database Project. Last updated 3 Apr 2006. Last accessed 4 Jan 2007. [1]
  • 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.
  • Aggarwal, Bharat et al; December 2006; "Curcumin: The Indian Solid Gold" [2]
  • Aggarwal BB, Kumar A, Bharti AC; "Anticancer potential of curcumin: preclinical and clinical studies." Anticancer Res.' 2003 Jan-Feb;23(1A):363-98. (PMID 12680238)
  • Ahmed M. Zahran. Influence of Curcumin on the Redox ‎System and Lipid Peroxidation in Gamma Irradiated Rats. ‎Egypt. J. Rad. Sci. Applic., 20(2): 385-404 (2007).‎
  • Campbell, Frederick C.; Collett, Gavin P. 2005. "Chemopreventive properties of curcumin." Future Oncology, 1(3), 405-414. (PMID 16556014)
  • Chattopadhyay, Ishita; Biswas, Kaushik; Bandyopadhyay, Uday; Banerjee, Ranajit K. 2004. "Turmeric and curcumin: biological actions and medicinal applications." Current Science', 87(1), 44-53.
  • Goel A, Kunnumakkara AB, Aggarwal BB; "Curcumin as 'Curecumin': From kitchen to clinic." Biochem Pharmacol', 2007 Aug 19; (PMID 17900536)
  • 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)
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