Curcumin

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Curcumin
Enol form
IUPAC 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
Identifiers
CAS number 458-37-7
SMILES
 
Properties
Molecular formula C21H20O6
Molar mass 368.38 g/mol
Appearance Bright Yellow
to Orange powder
Melting point

183°C (361 K)
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox references

Curcumin is the principal curcuminoid of the popular Indian curry spice turmeric, the other two curcuminoids being desmethoxycurcumin and bis-desmethoxycurcumin. 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.

Contents

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

For the last few decades, extensive work has been done to establish the biological activities and pharmacological actions of curcumin. Curcumin is known for its antitumor,23 antioxidant, antiarthritic, anti-amyloid, anti-ischemic4 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).It is also hepatoprotective.8 A 2008 study at Michigan State University showed that low concentrations of curcumin interfere with Herpes simplex virus-1 (HSV-1) replication.9 The same study showed that curcumin inhibited the recruitment of RNA polymerase II to viral DNA, thus inhibiting the transcription of the viral DNA.9 This effect was shown to be independent of effect on histone acetyltransferase activities of p300/CBP.9 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.10

Curcumin acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation11 and oxidative DNA damage. Curcuminoids induce glutathione S-transferase and are potent inhibitors of cytochrome P450.

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.12 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.13

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.14

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.15 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.

Numerous studies have demonstrated that curcumin, amongst only a few other things such as high impact exercise, learning, bright light, and antidepressant usage, has a positive affect on neurogenesis in the hippocampus and concentrations of brain-derived neurotrophic factor (BDNF), reductions in both of which are associated with stress, depression, and anxiety.16 17 18

Little curcumin, when eaten, is absorbed :19 from 2 to 10 grams of curcumin eaten alone resulted in undetectable to very low serum levels.20 Curcumin is unstable in the gut, and the traces that pass through the GI tract rapidly degrades or is conjugated through glucuronidation. Co-supplementation with 20 mg of piperine (extracted from black pepper) significantly increased the absorption of curcumin by 2000% in a study funded by a prominent manufacturer of piperine.20 Further, 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; however, no published studies to date have documented this. Cooking with curcumin and oil may increase absorption, however peer-reviewed scientific literature has not documented this, while the literature has documented concerns regarding the heat stability and degradation of curcumin in the gut.

In 2007, a polymeric nanoparticle encapsulated formulation of curcumin ("nanocurcumin"21) 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.21 However, actual in vivo absorption has not been demonstrated with this nanoparticle.

In July 2008, researchers from the aforementioned team in UCLA's Department of Neurology announced results on a form of "lipidated curcumin" that was noted to achieve more than 5 micromolar in the brain in vivo, 50 times that found in clinical studies.22 Another method to increase the bioavailability of curcumin filed a patent in 2006 that involves a simple procedure creating a complex with soy phospholipids, however the plasma concentration of curcumin using this formulation only reached 0.033 micromolar.23

Potential Risks & Side Effects

Kawanishi et al. (2005) of NCBI remarked that curcumin, like many antioxidants, can be a "double-edged sword" where in the test tube, anti-cancer and antioxidant effects may be seen in addition to pro-oxidant effects.24 Carcinogenic effects are inferred from interference with the p53 tumor suppressor pathway, an important factor in human colon cancer.25 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.26 This may prove curcumin medicinally useful as it helps activate p53citation needed. When a cell is inhibited by cancer the concentrations of p53 increase, helping cells defend against cancer mechanismscitation needed. But it may also suppress p53 levels, preventing cells from initiating defensive mechanisms, a response seen only in certain diseasescitation needed.

Clinical studies in humans with high doses (>2-12 grams) curcumin supplementation have shown some subjects reporting diarrhea and nausea; however, curcumin has also been indicated for these conditions as well. 27

References

  1. ^ Kolev, Tsonko M.; et al. (2005). "DFT and Experimental Studies of the Structure and Vibrational Spectra of Curcumin". International Journal of Quantum Chemistry (Wiley Periodicals) 102 (6): 1069–79. doi:10.1002/qua.20469. 
  2. ^ Aggarwal, BB.; Shishodia S. (May 2006). "Molecular targets of dietary agents for prevention and therapy of cancer". Biochemical Pharmacology (Elsevier) 71 (10): 1397–421. doi:10.1016/j.bcp.2006.02.009. 
  3. ^ Choi, Hyunsung; et al. (July 2006). "Curcumin Inhibits Hypoxia-Inducible Factor-1 by Degrading Aryl Hydrocarbon Receptor Nuclear Translocator: A Mechanism of Tumor Growth Inhibition". Molecular Pharmacology (American Society for Pharmacology and Experimental Therapeutics) 70: 1664–71. doi:10.1124/mol.106.025817. PMID 16880289. 
  4. ^ Shukla PK, Khanna VK, Ali MM, Khan MY, Srimal RC.Anti-ischemic effect of curcumin in rat brain, Neurochem Res. 2008 Jun;33(6):1036-43. Epub 2008 Jan 18, PMID: 18204970.
  5. ^ Stix, Gary (February 2007). "Spice Healer". Scientific American, http://sciam.com/article.cfm?chanID=sa006&articleID=131CED4F-E7F2-99DF-3C84BB412D1D3B51&pageNumber=1&catID=2. 
  6. ^ Srivastava, KC; Bordia A; Verma SK (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. doi:10.1016/0952-3278(95)90040-3. PMID 7784468. 
  7. ^ Padma, TV (2005-03-11). "Turmeric can combat malaria, cancer virus and HIV", SciDev.net. 
  8. ^ Marotta, F.; et al. (October 2003). "Hepatoprotective effect of a curcumin/absinthium compound in experimental severe liver injury". Chinese Journal of Digestive Diseases (Blackwell Publishing) 4 (3): 122–7. doi:10.1046/j.1443-9573.2003.00133.x. 
  9. ^ 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 373: 239. doi:10.1016/j.virol.2007.11.028. PMID 18191976. 
  10. ^ Bourne KZ, Bourne N, Reising SF, Stanberry LR (1999 July). "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. doi:10.1016/S0166-3542(99)00020-0. PMID 10443534. 
  11. ^ <Shukla PK, Khanna VK, Khan MY, Srimal RC.Protective effect of curcumin against lead neurotoxicity in rat.Hum Exp Toxicol. 2003 Dec;22(12):653-8.PMID: 14992327>
  12. ^ 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.
  13. ^ "Curcumin's anti-cancer mechanism proposed", nutraingredients-usa.com (2007-04-13). 
  14. ^ Yang, F; Lim GP; Begum AN; Ubeda OJ; Simmons MR; Ambegaokar SS; Chen PP; Kayed R; Glabe CG; Frautschy SA; Cole GM (February 2005). "Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo". Journal of Biological Chemistry (American Society for Biochemistry and Molecular Biology) 280 (7): 5892–901. doi:10.1074/jbc.M404751200. PMID 15590663. 
  15. ^ 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 (Oxford University Press) 164 (9): 898–906. doi:10.1093/aje/kwj267. PMID 16870699. 
  16. ^ Xu Y, Ku B, Cui L, Li X, Barish PA, Foster TC, Ogle WO. (August 2007). "Curcumin reverses impaired hippocampal neurogenesis and increases serotonin receptor 1A mRNA and brain-derived neurotrophic factor expression in chronically stressed rats". Brain Res 1162: 9. doi:10.1016/j.brainres.2007.05.071. PMID 17617388. 
  17. ^ Wu A, Ying Z, Gomez-Pinilla F. (February 2006). "Dietary curcumin counteracts the outcome of traumatic brain injury on oxidative stress, synaptic plasticity, and cognition". Experimental Neurology 197: 309. doi:10.1016/j.expneurol.2005.09.004. PMID 16364299. 
  18. ^ Bala K, Tripathy BC, Sharma D. (April 2006). "Neuroprotective and anti-ageing effects of curcumin in aged rat brain regions". Biogerontology 7: 81. doi:10.1007/s10522-006-6495-x. PMID 16802111. 
  19. ^ Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB (2007). "Bioavailability of curcumin: problems and promises". Molecular pharmaceutics 4 (6): 807–18. doi:10.1021/mp700113r. PMID 17999464. 
  20. ^ 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. doi:10.1055/s-2006-957450. PMID 9619120. 
  21. ^ a b Bisht; et al. (2007). "Polymeric nanoparticle-encapsulated curcumin ("nanocurcumin"): a novel strategy for human cancer therapy". Journal of Nanobiotechnology (BioMed Central) 5 (3): 3. doi:10.1186/1477-3155-5-3. PMID 17439648. 
  22. ^ Begum AN, Jones MR, Lim GP, Morihara T, Kim P, Heath DD, Rock CL, Pruitt MA, Yang F, Hudspeth B, Hu S, Faull KF, Teter B, Cole GM, Frautschy SA. (July 2008). "Curcumin structure-function, bioavailability, and efficacy in models of neuroinflammation and Alzheimer's disease.". J Pharmacol Exp Ther 326: 196. doi:doi:10.1124/jpet.108.137455. PMID 18417733. 
  23. ^ European patent EP20060004820
  24. ^ Kawanishi, S; Oikawa, S; Murata, M; (2005). "Evaluation for safety of antioxidant chemopreventive agents". Antioxidants & Redox Signaling 7 (11-12): 1728–39. doi:10.1089/ars.2005.7.1728. PMID 16356133. 
  25. ^ Moos PJ; Edes K; Mullally JE; Fitzpatrick FA (2004). "Curcumin impairs tumor suppressor p53 function in colon cancer cells". Carcinogenesis 25 (9): 1611–7. doi:10.1093/carcin/bgh163. PMID 15090465. 
  26. ^ Lois Swirsky Gold. Turmeric (>98% curcurmin). Carcinogenic Potency Database Project. Last updated 3 Apr 2006. Last accessed 4 Jan 2007. [1]
  27. ^ Hsu CH; Cheng AL. (2007). Adv Exp Med Biol. PMID 17569225. 

Further reading

 This section may require cleanup to meet Wikipedia's quality standards.
Please improve this article if you can. (May 2008)
  • 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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