Curcumin and curcuminoids in quest for medicinal status

• Autorzy: Grynkiewicz G. , Slifirski P.
• Języki publikacji: EN

Abstrakty

EN

Curcumin, known for thousands of years as an Ayurvedic medicine, and popular as a spice in Asian cuisine, has undergone in recent times remarkable transformation into a drug candidate with prospective multipotent therapeutic applications. Characterized by high chemical reactivity, resulting from an extended conjugated double bond system prone to nucleophilic attack, curcumin has been shown to interact with a plethora of molecular targets, in numerous experimental observations based on spectral, physicochemical or biological principles. The collected preclinical pharmacological data support traditional claims concerning the medicinal potential of curcumin and its congeners but at the same time point to their suboptimal properties in the ADME (absorption, distribution, metabolism and excretion) area.

• Wydawca: -
• Czasopismo: Acta Biochimica Polonica
• Rocznik: 2012
• Tom: 59
• Numer: 2
• Opis fizyczny: p.201-212,fig.,ref.

Twórcy

autor

Grynkiewicz G.

• Pharmaceutical Research Institute, Warszawa, Poland

autor

Slifirski P.

Bibliografia

• Aggarwal BB, Sundaram C, Malani N, Ichikawa H, (2007) Curcumin: the Indian solid gold. Adv Exp Med Biol 595: 1-75. 
• Aggarwal BB, Sung B, (2009) Pharmacological basis for the role of curcumin in chronic diseases: an ages-old spice with modern targets, Trends Pharmacol Sci 30: 85-94. 
• Aggarwal BB, Harikumar KB, (2009) Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegrative, cardiovascular, pulmonary, metabolic, autoimmune and neoplastic diseases. Int J Biochem Cell Biol 41: 40-59. 
• Agnihotri N, Mishra PC (2011) Scavenging mechanism of curcumin toward the hydroxyl radical: a theoretical study of reactions producing ferulic acid and vanillin. J Phys Chem A 115: 14221-14232. 
• Ammon HP, Wald MA (1991) Pharmacology of Curcuma longa. Planta Med 57: 1-7. 
• Anand P, Thomas SG, Kunnumakkara AB, Sundaram C, Harikumar KB, Sung B, Tharakan ST, Misra K, Priyadarsini IK, Rajasekharan KN, Aggarwal BB (2008) Biological activities of curcumin and its analogues (congeners) made by man and Mother Nature. Biochem Pharmacol 76: 1590-1611. 
• Anitha A, Deepagan VG, Divya Rani VV, Menon D, Nair SV Jayakumar R (2011) Preparation, characterization, in vitro drug release and biological studies of curcumin loaded dextran sulphate-chitosan nanoparticles. Carbohydr Polym 84: 1158-1164.
• Augustyniak A, Bartosz G, Cipak A, Duburs G, Horakova L, Luczaj W, Majekova M, Odysseos AD. Rackova L, Skrzydlewska E, Stefek M, Strosova M, Tirzitis G, Venskutonis PR, Viskupicova J, Vraka PS, Zarković N (2010) Natural and synthetic antioxidants: an updated overview. Free Radic Res 44: 1216-1262. 
• Babu KN, Ravindran PN, Sivaraman K (eds) Turmeric: the genus Curcuma. CRC Press, Boca Raton 2007. 
• Balaban AT, Parkanyi C, Ghiviriga I, Aaron JJ, Zajickova Z, Martinez OR (2008) Curcumin - benzodioxaborole chelates. ARKIVOC 2008: 1-9.
• Balasubramanian K (2006) Molecular orbital basis for yellow curry spice curcumin's prenvetion of Alzheimer disease. J Agric Food Chem 54: 3512-3520. 
• Bansal SS, Vadhanam MV, Gupta RC (2011) Development and in vitro-in vivo evaluation of polymeric implants for continuous systemic delivery of curcumin. Pharm Res 28: 1121-1130. 
• Bar-Sela G, Epelbaum R, Schaffer M (2010) Curcumin as an anticancer agent: review of the gap between basic and clinical applications. Curr Med Chem 17: 190-197. 
• Basile V, Ferrari E, Lazzari S, Belluti S, Pignedoli F, Imbriano C (2009) Curcumin derivatives: molecular basis of their anti-cancer activity. Biochem Pharmacol 78: 1305-1315. 
• Basnet P, Skalko-Basnet N (2011) Curcumin: an anti-inflammatory molecule from a curry spice on the path to cancer treatment. Molecules 16: 4567-4598. 
• Bergmann ED, Ginsburg D, Pappo R (1959) The Michael Reaction. Org React 10: 179-555.
• Bhawana Basniwal RK, Buttar HS, Jain VK, Jain N (2011) Curcumin nanoparticles: preparation, characterization, and antimicrobial study. J Agric Food Chem 59: 2056-2061. 
• Blumenthal M, Goldberg A, Brinckman J (2000) Herbal medicine. Expanded commission E monographs pp 379-384. American Botanical Council. 
• Buadonpri W, Wichitnithad W, Rojsitthisak P, Towiwat P (2009) Synthetic curcumin inhibits carrageenan - induced paw edema in rats. J Health Res 23: 11-16.
• Cheng AL, Hsu CH, Lin JK, Hsu MM, Ho YF, Shen TS, Ko JY, Lin JT, Lin BR, Ming-Shiang W et al. (2001) Phase I clinical trial of curcumin, a chemopreventive agent, in patientswith high-risk or pre-malignant lesions. Anticancer Res 21: 2895-2900. 
• Chignell CF, Bilski P, Reszka KJ, Motten KG, Sik RH, Dahl TA (1994) Spectral and photochemical properties of curcumin. Photochem Photobiol 59: 295-302. 
• Dubey SK, Sharma AK, Narain U, Misra K, Pati U (2008) Design, Synthesis and characterization of some bioactive conjugates of curcumin with glycine, glutamic acid, valine and demethylenated piperic acid and study of their antimicrobial and antiproliterative properties. Eur J Med Chem 43: 1837-1846. 
• Fan C, Wo X, Qian Y, Yin J, Gao L (2006) Effect of curcumin on the expression of LDL receptor in mouse macrophages. J Ethnopharmacol 105: 251-254. 
• Fang J, Lu J, Holmgren A (2005) Thioredoxin reductase is irreversibly modified by curcumin; a novel molecular mechanism for its anticancer activity. J Biol Chem 280: 25284-25290. 
• Feng JY, Liu ZQ (2011) Feruloylacetone as the model compound of half-curcumin: Synthesis and antioxidant properties. Eur J Med Chem 46: 1198-1206. 
• Ferrari E, Pignedoli F, Imbriano C, Marverti G, Basile V, Venturi E, Saladini M (2011) Newly synthesized curcumin derivatives: crosstalk between chemico-physical properties and biological activity. J Med Chem 54: 8066-8077. 
• Fujisawa S, Atsumi T, Ishihara M, Kadoma Y (2004) Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds. Anticancer Res 24: 563-569. 
• Girija CR, Karunakar P, Poojari CS, Begum NS, Syed AA (2010) Molecular docking studies of curcumin derivatives with multiple protein targets for procarcinogen activating enzyme inhibition. J Proteomics Bioinform 3: 200-203.
• Goel A, Aggarwal BB (2010) , Curcumin, the golden spice from Indian saffron, is a chemosensitizer and radiosensitizer for tumors and chemoprotector and radioprotector for normal organs. Nutr Cancer 62: 919-930. 
• Gupta NK, Dixit VK (2011) Bioavailability enhancement of curcumin by complexation with phosphatidylcholine. J Pharm Sci 100: 1987-1995. 
• Hassaninasab A, Hashimoto Y, Tanita-Yokotani K, Kobayashi M (2011) Discovery of the curcumin metabolic pathway involving a unique enzyme in an intestinal microorganism. PNAS 108: 6615-6620. 
• Hatcher H, Planalp R, Cho J, Torti FM, Torti SV (2008) Curcumin: from ancient medicin to current clinical trials. Cell Mol Life Sci 65: 1631-1652. 
• Herebian D, Choi JH, Abd El-Aty AM, Shim JH, Spiteller M (2009) Metabolite analysis in Curcuma domestica using various GC-MS and LC-MS separation and detection techniques. Biomed Chromatogr 23: 951-965. 
• Himesh S, Sharan PS, Mishra K, Govind N, Singhai AK (2011) Qualitative and quantitative profile of curcumin from ethanolic extract of Curcuma longa. Int Res J Pharm 2: 180-184.
• Ireson CR, Jones DJL, Orr S, Coughtrie MWH, Boocock DJ, Williams ML, Farmer PB, Steward WP, Gescher AJ (2002) Metabolism of the cancer chemopreventive agent curcumin in human and rat intestine. Cancer Epidemiol Biomarkers Prev 11: 105-111. 
• Ireson CR, Orr S, Jones DJ et al. (2001) Characterization of metabolites of the chemopreventive agent curcumin in human and rat hepatocytes and in the rat in vivo, and evaluation of their ability to inhibit phorbol ester-induced prostaglandin E2 production. Cancer Res 61: 1058-1064. 
• Jadhav BK, Mahadik KR, Paradkar AR (2007) Development and validation of improved reversed phase-HPLC Method for simultaneous determination of curcumin, demethoxycurcumin and bisdemethoxycurcumin. Chromatographia 65: 483-488.
• Jagetia GC (2007) Radioprotection and radiosesitization by curcumin, Adv Exp Med Biol 595: 301-320. 
• Jayaprakasha GK, Rao L JM, Sakariah KK (2002) Improved HPLC method for determination of curcumin, demethoxycurcumin, and bisdemethoxycurcumin. J Agric Food Chem 50: 3668-3672. 
• Joshi J, Ghaisas S, Vaidya A, Vaidya R, Kamat DV, Bhagwat AN, Bhide S (2003) Early human safety study of turmeric oil (Curcuma longa oil) administered orally in healthy volunteers. J Assoc Physicians India 51: 1055-1060. 
• Kakkar V, Singh S, Singla D, Kaur IP (2011) Exploring solid lipid nanoparticles to enhance the oral bioavailability of curcumin. Mol Nutr Food Res 55: 495-503. 
• Kapoor LD (1990) Handbook of Ayurvedic medicinal plants. p 185. CRC Press, Boca Raton. 
• Kelloff GJ, Crowell JA, Hawk ET, Steele VE, Lubet RA, Boone CW, et al. (1996) Strategy and planning for chemopreventive drug development: clinical development plans II. J Cell Biochem Suppl 26: 54-71. 
• Kim DC, Kim SH, Choi BH, Baek NI, Kim D, Kim MJ, Kim KT (2005) Curcuma longa extract protects against gastric ulcers by blocking H2 histamine receptors. Biol Pharm Bull 28: 2220-2224. 
• Kingston DGI (2011) Modern natural products drug discovery and its relevance to biodiversity conservation. J Nat Prod 74: 496-511. 
• Kita T, Imai S, Sawada H, Kumagai H, Seto H, (2008) The biosynthetic pathway of curcuminoid in turmeric (Curcuma longa) as revealed by 13C-labeled precursors. Biosci Biotechnol Biochem 72: 1789-1798. 
• Kolev TM, Velcheva EA, Stamboliyska BA, Spiteller M (2005) DFT and experimental studies of the structure and vibrational spectra of curcumin. Int J Quantum Chem 102: 1069-1079.
• Kowalewska E, Litwinienko G (2010) Fenolowe antyoksydanty interwentywne, aktywność i mechanizmy działania. Postepy Biochem 56: 274-283 (in Polish). 
• Kudva AK, Manoj MN, Swamy BN, Ramadoss CS (2011) Complexation of amphoterecin B and curcumin with serum albumin: Solubility and effect on erythrocyte membrane damage. J Exp Pharmacol 3: 1-6.
• Kumar A, Bore U (2011) In silico inhibition studies on NF κB p 50 subunit by curcumin and its natural analogs. Med Chem Res DOI: 10.1007/s00044-011-9873-0.
• Kurien BT, Scofield RH (2009) Oral administration of heat-solubilized curcumin for potentially increasing curcumin bioavailability in experimental animals. Int J Cancer 125: 1992-1993. 
• Lampe V, Miłobędzka J (1913) Studien uber Curcumin. Ber Dtsch Chem Ges 46: 2235-2240.
• Li JJ ed. (2009) Name Reactions. 355-356. Springer Verlag, Berlin Heidelberg.
• Li L, Ahmed B, Mehta K, Kurzrock R (2007) Liposomal curcumin with and without oxaliplatin: Effects on cell growth, apoptosis, and angiogenesis in colorectal cancer. Mol Cancer Ther 6: 1276-1282. 
• Li S, Yuan W, Deng G, Wang P Yang P, Aggarwal BB (2011) Chemical composition and product quality control of turmeric (Curcuma longa L.). Pharmaceutical Crops 2: 28-54.
• Li W, Wang SS, Feng JT, Xiao YS, Xue XY, Zhang H, Wang YQ, Liang XM (2009) Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa. Magn Reson Chem 47: 902-908. 
• Liddle M, Hull C, Liu C, Powell D (2006) Contact urticaria from curcumin. Dermatitis 17: 196-197. 
• Lin CL, Lin JK (2008) Curcumin: a potential cancer chemopreventive agent through suppressing NF-κB signaling. J Cancer Molecul 4: 11-16.
• Litwinienko G, Ingold KU (2007) Solvent effects on the rates and mechanisms of reaction of phenols with free radicals. Acc Chem Res 40: 222-230. 
• Ma Z, Haddadi A, Molavi O, Lavasanifar A, Lai R, Samuel J (2008) Micelles of poly(ethyleneoxide)-β-poly(ε-caprolactone) as vehicles for the solubilization, stabilization, and controlled delivery of curcumin. J Biomed Mater Res A 86: 300-310. 
• Maheshwari RK, Singh AK, Gaddipati J, Srimal RC (2006) Multiple biological activities of curcumin: A short review. Life Sci 78: 2081-2087. 
• Marathe SA, Dasgupta I, Gnanadhas DP, Chakravortty D (2011) Multifaceted roles of curcumin: two sides of a coin! Expert Opin Biol Ther 11: 1485-1499. 
• Marczylo TH, Verschoyle RD, Cooke DN et al. (2007) Comparison of systemic availability of curcumin with that of curcumin formulated withphosphatidylcholine. Cancer Chemother Pharmacol 60: 171-177. 
• Miłobędzka J, Kostanecki S, Lampe V (1910) Zur Kenntnis des Curcumins. Ber Dtsch Chem Ges 43: 2163-2170.
• Mitra SP (2007) Binding and stability of curcumin in presence of bovine serum albumin. J Surface Sci Technol 23: 91-110.
• Mohri K, Watanabe Y, Yoshida Y, Satoh M, Isobe K, Sugimoto N, Tsuda Y (2003) Synthesis of glycosylcurcuminoids. Chem Pharm Bull 51: 1268-1272. 
• Murali MY, Jaggi S, Chauhan C (2010) . β-Cyclodextrin-curcumin selfassembly enhances curcumin delivery in prostate cancer cells. Colloids and Surfaces B: Biointerfaces 79: 113-125. 
• Narlavar R, Pickhardt M, Lechtenberger S, Baumann K, Krause S, Dyrks T, Weggen S, Mandelkow E, Schmidt B (2008) Curcumin-derived pyrazoles and isoxazoles: Swiss army knives or blunt tools for Alzheimer's disease? Chem Med Chem 3: 165-172. 
• NIH Publ. No. 93-3158 (1993) Toxicology and carcinogenesis studies of turmeric oleoresin. Natl Tox Progr Tech Rep Ser 427: 1-287. 
• Nichols CE, Youssef D, Harris RG, Jha A (2006) Microwave - assisted synthesis of curcumin analogs. ARKIVOC 2006: 64-72.
• Padhye S, Chavan D, Pandey S, Deshpande J Swamy KV, Sarkar FH (2010) Perspective on chemopreventive and therapeutic potential of curcumin analogs in medicinal chemistry. Mini Rev Med Chem 10: 372-387. 
• Parameswari AR, Balu Devipriya B, Jenniefer SJ, Muthiah PT, Kumaradhas P (2011) Low Temperature Crystal Structure of 5-Hydroxy-1,7-Bis-(4-Hydroxy-3-Methoxy-Phenyl)-Hepta-1,6-Dien-3-one J Chem Crystallogr DOI: 10.1007/s10870-011-0229-x.
• Parimita SP, Ramashankar YV, Suresh S, Guru Row TN (2007) Redetermination of curcumin (1 E, 4 Z, 6 E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one, Acta Crystallogr Sect E Struct Rep Online E63: o860-o862.
• Parvathy KS, Negi PS, Srinivas P (2009) Antioxidant, antimutagenic and antibacterial activities of curcumin β-diglucoside. Food Chem 115: 265-271.
• Pathania V, Gupta AP, Singh B (2006) Improved HPTLC method for determination of curcuminoids from Curcuma longa. J Liquid Chromatogr Related Technolog 29: 877-887.
• Payton F, Sandusky P, Alworth WL (2007) NMR study of the solution structure of curcumin. J Nat Prod 70: 143-146. 
• Peret-Almedia L, Cherubino APF, Alves RJ, Dufosse L, Gloria MBA (2005) Separation and determination of physicochemical characteristics of curcumin, desmethoxycurcumin and bis desmethoxycurcumin. Food Res Int 38: 1039-1044.
• Priyadarsini KI., (2009) Photophysics, photochemistry and photobiology of curcumin: Studies from organic solutions, bio-mimetics and living cells. J Photochem Photobiol C: Photochemistry Rev 10: 81-95.
• Qiu X, Du Y, Lou B, Zuo Y, Shao W, Huo Y, Huang J, Yu Y, Zhou B, Du J, Fu H, Bu X (2010) Synthesis and identification of new 4-arylidene curcumin analogues as potential anticancer agents targeting nuclear factor-κB signaling pathway. J Med Chem 53: 8260-8273. 
• Ringman JM, Frautschy SA, Cole GM, Masterman DL, Cummings JL (2005) A potential role of the curry spice curcumin in Alzheimer's disease. Curr Alzheimer Res 2: 131-136. 
• Rohman A (2012) Analysis of curcuminoids in food and pharmaceutical products. Int Food Res J 19: 19-27.
• Roughley PJ, Whiting DA (1971) Diarylheptanoids: the problem of biosynthesis. Tetrahedron Lett 40: 5741-5746.
• Roughley PJ, Whiting DA (1973) Biosynthesis of curcumin. J Chem Soc Perkin Trans 1 1973: 2379-2388.
• Safavy A, Raisch KP, Mantena S, Sanford LL, Sham SW, Rama Krishna N, Bonner JA (2007) Design and development of water-soluble curcumin conjugates as potential anti-cancer agents. J Med Chem 50: 6284-6288. 
• Sanphuis P, Goud NR, Khandavilli UBR, Bhanoth B, Nangia A., (2011) New polymorphs of curcumin. Chem Commun (Camb) 47: 5013-5015. 
• Satpathy R, Guru RK, Behera R (2010) Computational QSAR analysis of some physiochemical and topological descriptors of Curcumin derivatives by using different statistical methods. J Chem Pharm Res 2: 344-350.
• Shaikh J, Ankola DD, Beniwal V, Singh D, Ravi Kumar MNV (2009) Nanoparticle encapsulation improves oral bioavailability of curcumin by at least 9-fold when compared to curcumin administered with piperine as absorption enhancer. Eur J Pharm Sci 37: 223-230. 
• Sharma RA, Euden SA, Platton SL, Cooke DN, Shafayat A, Hewitt HR, Marczylo TH, Morgan B, Hemingway D, Plummer SM, Pirmohamed M, Gescher AJ, Steward WP (2004) Phase I clinical trial of oral curcumin: biomarkers of systemic activity and compliance. Clin Cancer Res 10: 6847-6854. 
• Sharma RA, Ireson CR, Verschoyle RD, Hill KA, Williams ML, Leuratti C, Manson MM, Marnett LJ, Steward WP, Gescher A (2001) Effects of dietary curcumin on glutathione S-transferase and malondialdehyde-DNA adducts in rat liver and colon mucosa: Relationship with drug levels. Clin Cancer Res 7: 1452-1458. 
• Shehzad A, Lee YS (2010) Curcumin: Multiple molecular targets mediate multiple pharmacological actions: A review. Drugs Fut 35: 113-120.
• Shezad A, Wahid F, Lee YS (2010) Curcumin in cancer chemoprevention: molecular targets, pharmacokinetics, bioavailability and clinical trials. Arch Pharm (Weinheim) 343: 489-499. 
• 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 Med 64: 353-356. 
• Skrzypczak-Jankun E, Zhou K, Mccabe NP., Selman SH, Jankun J (2003) Structure of curcumin in complex with lipooxygensae and its significance in cancer. Int J Molec Med 12: 17-24. 
• Song Z, Feng R, Sun M, Guo C, Gao Y, Li L, Zhai G (2011) Curcumin-loaded PLGA-PEGPLGA triblock copolymeric micelles: Preparation, pharmacokinetics and distribution in vivo. J Colloid Interface Sci 354: 116-123. 
• Sotanaphun U, Phaechamud T, Dechwisissakul P (2007) Rapid screening method for curcuminoid content in turmeric (Curcuma longa Linn.). Thai Pharm Health Sci J 2: 125-130.
• Srimal RC (1987) Curcumin. Drugs Fut 12: 331-333.
• Srimal RC (1997) Turmeric: A brief review of medicinal properties. Fitoterapia 68: 483-493.
• Strimpakos AS, Sharma RA (2008) Curcumin: Preventive and Therapeutic Properties in Laboratory Studies and Clinical Trials. Antioxid Redox Signal 10: 511-546. 
• Takahashi M, Inafuku K, Miyagi T, Oku H, Wada K, Imura T, Kitamoto D (2007) Efficient preparation of liposomes encapsulating food materials using lecithins by a mechanochemical method. J Oleo Sci 56: 35-42. 
• Thompson DA, Tan BB (2006) Tetrahydrocurcumin-related allergic contact dermatitis. Contact Dermatitis 55: 254-255. 
• Tønnesen HH, Karlsen J, Mostad A (1982) Structural studies of curcuminoids. I. The crystal structure of curcumin. Acta Chem Scand B 36: 475-480.
• Tsai YM, Jan WC, Chien CF, Lee WC, Lin LC, Tsai TH (2011) Optimized nano-formulation on the bioavailability of hydrophobic polyphenol, curcumin, in freely-moving rats. Food Chem 127: 918-925.
• Vogel HA, Pelletier J (1815) Curcumin - biological and medicinal properties. J Pharma 2: 50-50.
• Wang D, Veena MS, Stevenson K, Tang C, Ho B, Suh JD, Duarte VM, Faull KF, Mehta K, Srivatsan ES, Wang MB (2008) Liposome-encapsulated curcumin suppresses growth of head and neck squamous cell carcinoma in vitro and in xenografts through the inhibition of nuclear factor-κB by an AKT-independent pathway. Clin Cancer Res 14: 6228-6236. 
• Weber WM, Hunsaker LA, Gonzales AM, Heynekamp JJ, Orlando RA, Deck LM, Van der Jagt DL (2006) TPA-induced up-regulation of activator protein-1 can be inhibited or enhanced by analogs of the natural product curcumin. Biochem Pharmacol 72: 928-940. 
• Wichitnithad W, Jongaroonngamsang N, Pummangura S, Rojsitthisak P (2009) A simple isocratic HPLC method for the simultaneous determination of curcuminoids in commercial turmeric extracts. Phytochem Anal 20: 314-319. 
• Wichitnithad W, Nimmannit U, Wacharasindhu S, Rojsitthisak P (2011) Synthesis, characterization and biological evaluation of succinate prodrugs of curcuminoids for colon cancer treatment. Molecules 16: 1888-1900. 
• Wilson M, Balaji S, Eapen J (2006) Druggability of lead compounds from turmeric (Curcuma longa). J Med Arom Plant Sci 28: 384-390.
• World Health Organization (1999) WHO monographs on selected medicinal plants. Part 1, vol 1, pp 115-124. Geneva. 
• Wu W, Shen J, Banerjee P, Zhou S (2011) Water-dispersible multifunctional hybrid nanogels for combined curcumin and photothermal therapy. Biomaterials 32: 598-609. 
• Yallapu MM, Jaggi M, Chauhan SC (2012) Curcumin nanoformulations: a future nanomedicine for cancer. Drug Discov Today 17: 71-80. 
• Yang F, Lim GP, Begum AN, Ubeda OJ, Simmons MR, Ambegaokar SS, Chen PP, Kayed R, Glabe CG, Frautschy SA, Cole GM (2005) Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J Biol Chem 280: 5892-5901. 
• Zebib B, Mouloungui Z, Noirot V (2010) Stabilization of curcumin by complexation with divalent cations in glycerol/water system. Bioinorg Chem Appl doi:10.1155/2010/292760. 
• Zhang J, Jinnai S, Ikeda R, Wada M, Shinjiro Hayashida S, Nakashima K (2009) A simple HPLC-fluorescence method for quantitation of curcuminoids and its application to turmeric products. Anal Sci 25: 385-388. 
• Zhou H, Beevers CS, Huang S (2011) The targets of curcumin. Curr Drug Targets 12: 332-347

Uwagi

PL

Rekord w opracowaniu.