Curcumin

Curcumin
Curcumin

Enol form

Keto form

Identifiers CAS number PubChem ChemSpider UNII ChEBI ChEMBL Jmol-3D images 458-37-7 969516 839564
[1]

[2] [3] [4] [5]

IT942ZTH98 CHEBI:3962

[6]

CHEMBL116438 Image 1 Properties

[7]

Molecular formula Molar mass Appearance Melting point

(verify) [8]

C H O

21 20 6

368.38 g mol1 Bright yellow-orange powder 183C, 456K, 361F

(what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25C, 100kPa)

Infobox references

Curcumin is the principal curcuminoid of the popular Indian spice turmeric, which is a member of the ginger family (Zingiberaceae). Turmeric's other two curcuminoids are desmethoxycurcumin and bis-desmethoxycurcumin. The curcuminoids are natural phenols that are responsible for the yellow color of turmeric. Curcumin can exist in several

Curcumin tautomeric forms, including a 1,3-diketo form and two equivalent enol forms. The enol form is more energetically stable in the solid phase and in solution.[9] Curcumin can be used for boron quantification in the curcumin method. It reacts with boric acid to form a red-colored compound, rosocyanine. Curcumin is brightly yellow colored and may be used as a food coloring. As a food additive, its E number is E100.[10]

Chemistry
Curcumin incorporates several functional groups. The aromatic ring systems, which are phenols, are connected by two ,-unsaturated carbonyl groups. The diketones form stable enols and are readily deprotonated to form enolates; the ,-unsaturated carbonyl group is a good Michael acceptor and undergoes nucleophilic addition. The structure was first identified in 1910 by J. Miobdzka, Stanisaw Kostanecki and Wiktor Lampe.[11] Curcumin is used as an indicator for boron.[12]
Curcumin

Biosynthesis
The biosynthetic route of curcumin has proven to be very difficult for researchers to determine. In 1973 Roughly and Whiting proposed two mechanisms for curcumin biosynthesis. The first mechanism involved a chain extension reaction by cinnamic acid and 5 malonyl-CoA molecules that eventually arylized into a curcuminoid. The second mechanism involved two cinnamate units being coupled together by malonyl-CoA. Both mechanisms use cinnamic acid as their starting point, which is derived from the amino acid phenylalanine. This is noteworthy because plant biosyntheses employing cinnamic acid as a starting point are rare compared to the more common use of p-coumaric acid.[13] Only a few identified compounds, such as anigorufone and pinosylvin, use cinnamic acid as their start molecule.[14][15] An experimentally backed route was not presented until 2008. This proposed biosynthetic route follows both the first and second mechanisms suggested by Roughley and Whiting. However, the labeling data supported the first mechanism model in which 5 malonyl-CoA molecules react with cinnamic acid to form curcumin. However, the sequencing in which the functional groups, the alcohol and the methoxy, introduce themselves onto the curcuminoid seems to support more strongly the second proposed mechanism.[13] Therefore, it was concluded the second pathway proposed by Roughly and Whiting was correct.

Curcumin

Potential medical uses

Although many preclinical studies suggest curcumin may be useful for the prevention and treatment of several diseases, the effectiveness of curcumin has not yet been demonstrated in randomized, placebo-controlled, double-blind clinical trials.[16] A daily dose of 2grams of Curcuma domestica extract was found to provide pain relief that was equivalent to ibuprofen for the relief of pain associated with osteoarthritis of the knee.[17] An extensive survey of the literature shows a number of other potential uses and that daily doses over [18] a 3 month period of up to 12grams proved safe. Some commercial capsules of curcumin contain piperine, a compound found in pepper which aids absorption of curcumin into the blood stream. However, as curcuma is known to inhibit blood clotting, it should be avoided for a two week period prior to major surgery and not used in conjunction with blood thinners such as warfarin and Plavix. It is also known to aggravate gallstone problems.[19]

Research
Turmeric has been used historically as a component of Indian Ayurvedic medicine. Research in the latter half of the 20th century identified curcumin as the agent responsible for most of the biological activity of turmeric.[20] In vitro and animal studies have suggested a wide range of potential therapeutic or preventive effects associated with curcumin. At present, these effects have not been confirmed in humans. As of 2008, numerous clinical trials in humans were underway, studying the effect of curcumin on various diseases, including multiple myeloma, pancreatic cancer, myelodysplastic syndromes, colon cancer, psoriasis, and Alzheimer's disease.[21] In both in vitro and animal studies, curcumin has shown antitumor,[22][23][24] antioxidant, antiarthritic, antiamyloid, anti-ischemic,[25] and anti-inflammatory properties.[26] Anti-inflammatory properties may be due to inhibition of eicosanoid biosynthesis.[27] There is a study that demonstrated that curcumin may be an alternative antimicrobial agent against fatal bacterial infections including Vibrio vulnificus infection. In the study, curcumin protected mice from V. vulnificus-induced septicemia.[28] In HIV, it appears to act by interfering with P300/CREB-binding protein (CBP). A study found it hepatoprotective in combination with Absinthium in rats.[29] A study found that low concentrations of curcumin interfere with Herpes simplex virus-1 (HSV-1) replication. It inhibited the recruitment of RNA polymerase II to viral DNA, thus inhibiting its transcription. This effect was independent of the effect on histone acetyltransferase activities of p300/CBP.[30] A study found that curcumin is significantly associated with protection from infection by HSV-2 in animal models of intravaginal infections.[31] A study found that curcumin acts as a free radical scavenger and antioxidant, inhibiting lipid peroxidation and oxidative DNA damage, protecting against lead neurotoxicity, in rats.[32]

Curcumin Curcuminoids induce glutathione S-transferase and are potent inhibitors of cytochrome P450. Curcumin was shown to be effective in protecting against toxicity and spatial memory impairment induced by amyloid -protein infusion in a rat model.[33] A study using a transgenic animal model indicated that curcumin diminished plaque burden and overall inflammation, but it also increased plaque-associated inflammatory cells suggesting enhanced clearance.[34] A study found that curcumin shrank the size of plaques and reduced neurite dystrophy in an Alzheimer mouse model.[35] A study found curcumin to have a synergistic effect with fish oil to protect against cognitive deficits in a transgenic rodent model.[36] However, the results of studies in rodents may not translate to humans. In humans, unlike rats, curcumin is extensively metabolized to the glucuronidated form, which does not penetrate the bloodbrain barrier and is therefore unable to reach brain tissues. Numerous studies have demonstrated that curcumin has a positive effect on neurogenesis in the hippocampus and increases the levels of brain-derived neurotrophic factor (BDNF) in rats.[37][38][39] A curcumin pyrazole derivative identified by high throughput screening was found to improve memory and was broadly neuroprotective, stimulating BDNF in vitro and in vivo.[40][41] The compound was found to be protective in animal models of brain trauma and stroke.[42][43]

Anticarcinogenic effects
Its potential 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-B, which has been linked to a number of inflammatory diseases such as cancer.[44] A 2009 study suggested curcumin may inhibit mTOR complex I via a novel mechanism.[45] Another 2009 study on curcumin effects on cancer states it "modulates growth of tumor cells through regulation of multiple cell signaling pathways including cell proliferation pathway (cyclin D1, c-myc), cell survival pathway (Bcl-2, Bcl-xL, cFLIP, XIAP, c-IAP1), caspase activation pathway (caspase-8, 3, 9), tumor suppressor pathway (p53, p21) death receptor pathway (DR4, DR5), mitochondrial pathways, and protein kinase pathway (JNK, Akt, and AMPK)".[46] An in vitro study in a human glioblastoma cell line reported that curcumin effectively inhibits tumor cell proliferation, as well as migration and invasion, and that these effects may be mediated through interference with the STAT3 signaling pathway.[47] When 0.2% curcumin is added to diet given to rats or mice previously given a carcinogen, it significantly reduces colon carcinogenesis.[48] In a study curcumin has been shown in vitro to have phyto-estrogenic activity that might contribute to activity against breast cancer.[49] In immunodeficient mice with breast cancer, curcumin inhibited the formation of lung metastases through the NF-B dependent regulation of protumorigenic inflammatory cytokines.[51]
[50]

probably

A study found that curcumin might be potentially useful in some kidney diseases by reducing lipopolysaccharide-induced renal inflammation.[52]

Curcumin

Bioavailability
In Phase I clinical trials, dietary curcumin was shown to exhibit poor bioavailability (i.e., low levels in plasma and tissues).[53] Potential factors that limit the bioavailability of curcumin include poor absorption, rapid metabolism, and rapid systemic elimination. Numerous approaches to increasing curcumin bioavailability have been explored including the use of adjuvants like piperine, which interfere with glucuronidation; liposomal curcumin; nanoparticles; curcumin phospholipid complexes; and structural analogues of curcumin (e.g., EF-24).[53] The bioavailability of curcumin ingested in foods may be increased as a result of cooking or dissolution in oil.[54]

Resistance
Overexpression of the ATP-binding cassette gene ABCA1 has been reported to confer resistance to Curcumin in terms of NFkappaB activation that can be reverted by ABCA1 silencing.[55]

Potential risks and side effects

Kawanishi et al. remarked that curcumin, like many antioxidants, can be a "double-edged sword" where, in the test tube, carcinogenic and pro-oxidant effects may be seen in addition to anticancer and antioxidant effects.[56] Carcinogenic effects are inferred from interference with the p53 tumor suppressor pathway, an important factor in human colon cancer.[57] In vitro and in vivo studies suggest that curcumin can have carcinogenic effects.[58][59][60] Clinical studies in humans with high doses (212grams) of curcumin have shown few side effects, with some subjects reporting mild nausea or diarrhea.[61] More recently, curcumin was found to alter iron metabolism by chelating iron and suppressing the protein hepcidin, potentially causing iron deficiency in susceptible patients.[62] Further studies seem to be necessary to establish the benefit/risk profile of curcumin.[58] There is no or little evidence to suggest curcumin is either safe or unsafe for pregnant women. However, there is still some concern medicinal use of products containing curcumin could stimulate the uterus, which may lead to a miscarriage, although there is not much evidence to support this claim. According to experiments done on rats and guinea pigs, there is no obvious effect (neither positive, nor negative) on the pregnancy rate or number of live or dead embryos.[63] Curcumin has embryotoxic and teratogenic effects on zebrafishes (Danio rerio) embryos.[64]

References
Notes
[1] [2] [3] [4] [5] [6] [7] http:/ / www. commonchemistry. org/ ChemicalDetail. aspx?ref=458-37-7 http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=969516 http:/ / www. chemspider. com/ 839564 http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=IT942ZTH98 https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=3962 https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL116438 http:/ / chemapps. stolaf. edu/ jmol/ jmol. php?model=O%3DC%28%5CC%3DC%5Cc1ccc%28O%29c%28OC%29c1%29CC%28%3DO%29%5CC%3DC%5Cc2cc%28OC%29c%28O%29cc2 [8] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=477166233& page2=%3ACurcumin [9] Kolev, Tsonko M.; Velcheva, Evelina A.; Stamboliyska, Bistra A.; Spiteller, Michael (2005). "DFT and experimental studies of the structure and vibrational spectra of curcumin". International Journal of Quantum Chemistry 102 (6): 106979. doi:10.1002/qua.20469. [10] Food Standards Australia New Zealand. "Food Additives- Numerical List" (http:/ / www. foodstandards. gov. au/ newsroom/ publications/ choosingtherightstuff/ foodadditivesnumeric1680. cfm). . Retrieved 2009-12-02. [11] Miobdzka, J.; v. Kostanecki, St.; Lampe, V. (1910). "Zur Kenntnis des Curcumins". Berichte der deutschen chemischen Gesellschaft 43 (2): 216370. doi:10.1002/cber.191004302168. [12] "EPA Method 212.3: Boron (Colorimetric, Curcumin)" (http:/ / www. caslab. com/ EPA-Methods/ PDF/ EPA-Method-2123. pdf). . [13] Kita, Tomoko; Imai, Shinsuke; Sawada, Hiroshi; Kumagai, Hidehiko; Seto, Haruo (2008). "The Biosynthetic Pathway of Curcuminoid in Turmeric (Curcuma longa) as Revealed by 13C-Labeled Precursors". Bioscience, Biotechnology, and Biochemistry 72 (7): 1789. doi:10.1271/bbb.80075.

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[14] Schmitt, Bettina; Hlscher, Dirk; Schneider, Bernd (2000). "Variability of phenylpropanoid precursors in the biosynthesis of phenylphenalenones in Anigozanthos preissii". Phytochemistry 53 (3): 3317. doi:10.1016/S0031-9422(99)00544-0. PMID10703053. [15] Gehlert, R.; Schoeppner, A.; Kindl, H. (1990). "Stilbene Synthase from Seedlings of Pinus sylvestris: Purification and Induction in Response to Fungal Infection" (http:/ / www. apsnet. org/ publications/ mpmi/ backissues/ Documents/ 1990Articles/ Microbe03_444. pdf) (pdf). Molecular Plant-Microbe Interactions 3 (6): 444449. doi:10.1094/MPMI-3-444. . [16] Mancuso, C.; Barone, E. (2009). "Curcumin in clinical practice: myth or reality?". Trends in Pharmacological Science 30 (7): 333334. doi:10.1016/j.tips.2009.04.004. PMID19523696. [17] Kuptniratsaikul, Vilai; Thanakhumtorn, Sunee; Chinswangwatanakul, Pornsiri; Wattanamongkonsil, Luksamee; Thamlikitkul, Visanu (2009). "Efficacy and Safety ofCurcuma domesticaExtracts in Patients with Knee Osteoarthritis". The Journal of Alternative and Complementary Medicine 15 (8): 8917. doi:10.1089/acm.2008.0186. PMID19678780. "Curcuma domestica extracts seem to be similarly efficacious and safe as ibuprofen for the treatment of knee Osteoarthritis." [18] Goel, Ajay; Kunnumakkara, Ajaikumar B.; Aggarwal, Bharat B. (2008). "Curcumin as "Curecumin": From kitchen to clinic". Biochemical Pharmacology 75 (4): 787809. doi:10.1016/j.bcp.2007.08.016. PMID17900536. "Pilot phase I clinical trials have shown curcumin to be safe even when consumed at a daily dose of 12g for 3 months." [19] O'Connor, Anahad (October 19, 2011). "The Doctors Remedy: Turmeric for Joint Pain" (http:/ / well. blogs. nytimes. com/ 2011/ 10/ 19/ the-doctors-remedy-turmeric-for-joint-pain/ ). The New York Times. . Retrieved 2011-10-20. [20] Aggarwal, Bharat B.; Sundaram, Chitra; Malani, Nikita; Ichikawa, Haruyo (2007). "CURCUMIN: THE INDIAN SOLID GOLD". The Molecular Targets and Therapeutic Uses of Curcumin in Health and Disease. ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY. 595. pp.1. doi:10.1007/978-0-387-46401-5_1. ISBN978-0-387-46400-8. [21] Hatcher, H.; Planalp, R.; Cho, J.; Torti, F. M.; Torti, S. V. (2008). "Curcumin: From ancient medicine to current clinical trials". Cellular and Molecular Life Sciences 65 (11): 163152. doi:10.1007/s00018-008-7452-4. PMID18324353. [22] Strfer, Mareike; Jelkmann, Wolfgang; Depping, Reinhard (2011). "Curcumin Decreases Survival of Hep3B Liver and MCF-7 Breast Cancer Cells". Strahlentherapie und Onkologie 187 (7): 393400. doi:10.1007/s00066-011-2248-0. PMID21713389. [23] Aggarwal, Bharat B.; Shishodia, Shishir (2006). "Molecular targets of dietary agents for prevention and therapy of cancer". Biochemical Pharmacology 71 (10): 1397421. doi:10.1016/j.bcp.2006.02.009. PMID16563357. [24] Choi, H.; Chun, Y.-S.; Kim, S.-W.; Kim, M.-S.; Park, J.-W. (2006). "Curcumin Inhibits Hypoxia-Inducible Factor-1 by Degrading Aryl Hydrocarbon Receptor Nuclear Translocator: A Mechanism of Tumor Growth Inhibition". Molecular Pharmacology 70 (5): 166471. doi:10.1124/mol.106.025817. PMID16880289. [25] Shukla, Pradeep K.; Khanna, Vinay K.; Ali, Mohd. M.; Khan, Mohd. Y.; Srimal, Rikhab C. (2008). "Anti-ischemic Effect of Curcumin in Rat Brain". Neurochemical Research 33 (6): 103643. doi:10.1007/s11064-007-9547-y. PMID18204970. [26] Stix, G. (February 2007). "Spice Healer" (http:/ / sciam. com/ article. cfm?chanID=sa006& articleID=131CED4F-E7F2-99DF-3C84BB412D1D3B51& pageNumber=1& catID=2). Scientific American 296 (2): 66. doi:10.1038/scientificamerican0207-66. . [27] Srivastava, K.C.; Bordia, A.; Verma, S.K. (1995). "Curcumin, a major component of food spice turmeric (Curcuma longa) inhibits aggregation and alters eicosanoid metabolism in human blood platelets". Prostaglandins, Leukotrienes and Essential Fatty Acids 52 (4): 223. doi:10.1016/0952-3278(95)90040-3. [28] Na, HS; Cha, MH; Oh, DR; Cho, CW; Rhee, JH; Kim, YR (2011). "Protective mechanism of curcumin against Vibrio vulnificus infection". FEMS immunology and medical microbiology 63 (3): 35562. doi:10.1111/j.1574-695X.2011.00855.x. PMID22092562. [29] Marotta, F; Shield, YR; Bamba, T; Naito, Y; Minelli, E; Yoshioka, M (2003). "Hepatoprotective effect of a curcumin/absinthium compound in experimental severe liver injury". Chinese Journal of Digestive Diseases 4 (3): 122. doi:10.1046/j.1443-9573.2003.00133.x. [30] Kutluay, Sebla B.; Doroghazi, James; Roemer, Martha E.; Triezenberg, Steven J. (2008). "Curcumin inhibits herpes simplex virus immediate-early gene expression by a mechanism independent of p300/CBP histone acetyltransferase activity". Virology 373 (2): 23947. doi:10.1016/j.virol.2007.11.028. PMC2668156. PMID18191976. [31] Bourne, Krystyn Z.; Bourne, Nigel; Reising, Shirley F.; Stanberry, Lawrence R. (1999). "Plant products as topical microbicide candidates: Assessment of in vitro and in vivo activity against herpes simplex virus type 2". Antiviral Research 42 (3): 21926. doi:10.1016/S0166-3542(99)00020-0. PMID10443534. [32] Shukla, Pradeep K; Khanna, Vinay K; Khan, Mohd Y; Srimal, Rikhab C (2003). "Protective effect of curcumin against lead neurotoxicity in rat". Human & Experimental Toxicology 22 (12): 653. doi:10.1191/0960327103ht411oa. [33] Frautschy, S; Hu, W; Kim, P; Miller, SA; Chu, T; Harris-White, ME; Cole, GM (2001). "Phenolic anti-inflammatory antioxidant reversal of A-induced cognitive deficits and neuropathology". Neurobiology of Aging 22 (6): 9931005. doi:10.1016/S0197-4580(01)00300-1. PMID11755008. [34] Chu, Giselle P.; Chu, Teresa; Yang, Fusheng; Beech, Walter; Frautschy, Sally A.; Cole, Greg M. (2001). "The Curry Spice Curcumin Reduces Oxidative Damage and Amyloid Pathology in an Alzheimer Transgenic Mouse". The Journal of Neuroscience 21 (21): 83707. PMID11606625. [35] Garcia-Alloza, M.; Borrelli, L. A.; Rozkalne, A.; Hyman, B. T.; Bacskai, B. J. (2007). "Curcumin labels amyloid pathology invivo, disrupts existing plaques, and partially restores distorted neurites in an Alzheimer mouse model". Journal of Neurochemistry 102 (4): 1095104. doi:10.1111/j.1471-4159.2007.04613.x. PMID17472706. [36] Ma, Q.-L.; Yang, F.; Rosario, E. R.; Ubeda, O. J.; Beech, W.; Gant, D. J.; Chen, P. P.; Hudspeth, B. et al. (2009). "-Amyloid Oligomers Induce Phosphorylation of Tau and Inactivation of Insulin Receptor Substrate via c-Jun N-Terminal Kinase Signaling: Suppression by

Curcumin
Omega-3 Fatty Acids and Curcumin". Journal of Neuroscience 29 (28): 907889. doi:10.1523/JNEUROSCI.1071-09.2009. PMID19605645. [37] Xu, Ying; Ku, Baoshan; Cui, Li; Li, Xuejun; Barish, Philip A.; Foster, Thomas C.; Ogle, William O. (2007). "Curcumin reverses impaired hippocampal neurogenesis and increases serotonin receptor 1A mRNA and brain-derived neurotrophic factor expression in chronically stressed rats". Brain Research 1162: 918. doi:10.1016/j.brainres.2007.05.071. PMID17617388. [38] Wu, Aiguo; Ying, Zhe; Gomez-Pinilla, Fernando (2006). "Dietary curcumin counteracts the outcome of traumatic brain injury on oxidative stress, synaptic plasticity, and cognition". Experimental Neurology 197 (2): 30917. doi:10.1016/j.expneurol.2005.09.004. PMID16364299. [39] Bala, Kiran; Tripathy, B. C.; Sharma, Deepak (2006). "Neuroprotective and Anti-ageing Effects of Curcumin in Aged Rat Brain Regions". Biogerontology 7 (2): 819. doi:10.1007/s10522-006-6495-x. PMID16802111. [40] Maher, Pamela; Akaishi, Tatsuhiro; Schubert, David; Abe, Kazuho (2010). "A pyrazole derivative of curcumin enhances memory". Neurobiology of Aging 31 (4): 7069. doi:10.1016/j.neurobiolaging.2008.05.020. PMID18639368. [41] Liu, Y.; Dargusch, R.; Maher, P.; Schubert, D. (2008). "A broadly neuroprotective derivative of curcumin". Journal of Neurochemistry 105 (4): 13361345. doi:10.1111/j.1471-4159.2008.05236.x. PMID18208543. [42] Wu, A.; Ying, Z.; Schubert, D.; Gomez-Pinilla, F. (2011). "Brain and spinal cord interaction: a dietary curcumin derivative counteracts locomotor and cognitive deficits after brain trauma". Neurorehabilitation and Neural Repair 25 (4): 332342. doi:10.1177/1545968310397706. PMC3258099. PMID21343524. [43] Lapchak, P.; Schubert, D. R.; Maher, P. A. (2011). "Delayed Treatment with a Novel Neurotrophic Compound Reduces Behavioral Deficits in Rabbit Ischemic Stroke". Journal of Neurochemistry 116 (1): 122131. doi:10.1111/j.1471-4159.2010.07090.x. PMC3004475. PMID21054387. [44] Aggarwal, B. B.; Shishodia, S. (2004). "Suppression of the Nuclear Factor-B Activation Pathway by Spice-Derived Phytochemicals: Reasoning for Seasoning". Annals of the New York Academy of Sciences 1030: 434441. doi:10.1196/annals.1329.054. PMID15659827. [45] Beevers, C. S.; Chen, L.; Liu, L.; Luo, Y.; Webster, N. J. G.; Huang, S. (2009). "Curcumin disrupts the Mammalian target of rapamycin-raptor complex". Cancer Research 69 (3): 10001008. doi:10.1158/0008-5472.CAN-08-2367. PMID19176385. [46] Ravindran, J.; Prasad, S.; Aggarwal, B. B. (2009). "Curcumin and Cancer Cells: How Many Ways Can Curry Kill Tumor Cells Selectively?". The AAPS Journal 11 (3): 495510. doi:10.1208/s12248-009-9128-x. PMC2758121. PMID19590964. [47] Senft, C.; Polacin, M.; Priester, M.; Seifert, V.; Kgel, D.; Weissenberger, J. (2010). "The nontoxic natural compound Curcumin exerts anti-proliferative, anti-migratory, and anti-invasive properties against malignant gliomas". BMC Cancer 10: 491. doi:10.1186/1471-2407-10-491. PMC2949804. PMID20840775. [48] Data from sixteen scientific articles reported in the Chemoprevention Database (http:/ / www. inra. fr/ internet/ Projets/ reseau-nacre/ sci-memb/ corpet/ indexan. html) [49] Bachmeier, B. E.; Mirisola, V.; Romeo, F.; Generoso, L.; Esposito, A.; DellEva, R.; Blengio, F.; Killian, P. H.; Albini, A. (2010). "Reference profile correlation reveals estrogen-like trancriptional activity of Curcumin". Cell Physiology and Biochemistry 26 (3): 471482. doi:10.1159/000320570. PMID20798532. [50] Bachmeier, B. E.; Nerlich, A.; Iancu, C.; Cilli, M.; Schleicher, E.; Ven, R.; DellEva, R.; Jochum, M. et al. (2007). "The chemopreventive polyphenol Curcumin prevents hematogenous breast cancer metastases in immunodeficient mice" (http:/ / content. karger. com/ produktedb/ produkte. asp?DOI=000099202& typ=pdf) (pdf). Cell Physiology and Biochemistry 19 (14): 137152. doi:10.1159/000099202. PMID17310108. . [51] Bachmeier, B. E.; Mohrenz, I. V.; Mirisola, V.; Schleicher, E.; Romeo, F.; Hohneke, C.; Jochum, M.; Nerlich, A. G. et al. (2008). "Curcumin downregulates the inflammatory cytokines CXCL1 and -2 in breast cancer cells via NFB". Carcinogenesis 29 (4): 779789. doi:10.1093/carcin/bgm248. PMID17999991. [52] Zhong, F.; Chen, H.; Han, L.; Jin, Y.; Wang, W. (2011). "Curcumin attenuates lipopolysaccharide-induced renal inflammation". Biological and Pharmaceutical Bulletin 34 (2): 226232. doi:10.1248/bpb.34.226. PMID21415532. [53] Anand, P.; Kunnumakkara, A. B.; Newman, R. A.; Aggarwal, B. B. (2007). "Bioavailability of curcumin: problems and promises". Molecular Pharmaceutics 4 (6): 807818. doi:10.1021/mp700113r. PMID17999464. [54] Marczylo, T. H.; Verschoyle, R. D.; Cooke, D. N.; Morazzoni, P.; Steward, W. P.; Gescher, A. J. (2007). "Comparison of systemic availability of curcumin with that of curcumin formulated with phosphatidylcholine". Cancer Chemotherapy and Pharmacology 60 (2): 171177. doi:10.1007/s00280-006-0355-x. PMID17051370. [55] Bachmeier BE, Iancu CM, Killian PH, Kronski E, Mirisola V, Angelini G, Jochum M, Nerlich AG,Pfeffer U. (2009). "Overexpression of the ATP binding cassette gene ABCA1 determines resistance to Curcumin in M14 melanoma cells". Mol Cancer 8: 129141. doi:10.1186/1476-4598-8-129. PMC2804606. PMID20030852. [56] Kawanishi, S.; Oikawa, S.; Murata, M. (2005). "Evaluation for safety of antioxidant chemopreventive agents". Antioxidants & Redox Signaling 7 (1112): 17281739. doi:10.1089/ars.2005.7.1728. PMID16356133. [57] Moos, P. J.; Edes, K.; Mullally, J. E.; Fitzpatrick, F. A. (2004). "Curcumin impairs tumor suppressor p53 function in colon cancer cells". Carcinogenesis 25 (9): 16111617. doi:10.1093/carcin/bgh163. PMID15090465. [58] Burgos-Moron, E.; Caldern-Montao, J. M.; Salvador, J.; Robles, A.; Lpez-Lzaro, M. (2010). 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Curcumin
[60] Lpez-Lzaro, M.; Kock, N. D.; Moore, J. E.; Lin, E. Y.; Mosley, L. J.; d'Agostino, R. B.; McCoy, T. P.; Townsend, A. J. et al. (2008). "Anticancer and carcinogenic properties of curcumin: considerations for its clinical development as a cancer chemopreventive and chemotherapeutic agent". Molecular Nutrition and Food Research 52 (Supplement 1): S103S127. doi:10.1002/mnfr.200700238. PMID18496811. [61] Hsu, C. H.; Cheng, A. L. (2007). "Clinical studies with curcumin". Advances in Experimental Medicine and Biology. ADVANCES IN EXPERIMENTAL MEDICINE AND BIOLOGY 595: 471480. doi:10.1007/978-0-387-46401-5_21. ISBN978-0-387-46400-8. PMID17569225. [62] Jiao, Y.; Wilkinson, J.; Di, X.; Wang, W.; Hatcher, H.; Kock, N. D.; d'Agostino, R.; Knovich, M. A. et al. (January 2009). "Curcumin, a cancer chemopreventive and chemotherapeutic agent, is a biologically active iron chelator". Blood 113 (2): 462469. doi:10.1182/blood-2008-05-155952. PMC2615657. PMID18815282. [63] Vijayalaxmi (1980). "Genetic effects of turmeric and curcumin in mice and rats". Mutation Research 79 (2): 125132. doi:10.1016/0165-1218(80)90080-4. PMID7432370. [64] Wu, J. Y.; Lin, C. Y.; Lin, T. W.; Ken, C. F.; Wen, Y. D. (2007). "Curcumin Affects Development of Zebrafish Embryo". Biol. Pharm. Bull 30 (7): 13361339. doi:10.1248/bpb.30.1336. PMID17603177.

See also: Esatbeyoglu, Tuba; Huebbe, Patricia; Ernst, Insa M. A.; Chin, Dawn; Wagner, Anika E.; Rimbach, Gerald (2012). "Curcumin-From Molecule to Biological Function". Angewandte Chemie International Edition 51 (22): 5308. doi:10.1002/anie.201107724.

External links
Turmeric and curcumin (http://www.mskcc.org/mskcc/html/11571.cfm?RecordID=429&tab=HC), from Memorial Sloan-Kettering Cancer Center Turmeric and curcumin (http://www.mdanderson.org/departments/cimer/dindex. cfm?pn=915cd45e-7c37-4305-8e778e10de640e0c), from M.D. Anderson Cancer Center Turmeric (http://www.umm.edu/altmed/articles/turmeric-000277.htm), from the University of Maryland Medical Center

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