Curcumin: From chemistry to chemistry-based functions

Current Pharmaceutical Design

Volumn 19, Issue 11, 2013, Pages 2084-2092

  Jitoe Masuda, Akiko ^a   Fujimoto, Aya ^b   Masuda, Toshiya ^b  

^a SHIKOKU UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Antioxidant activity; Antioxidation mechanism; Curcumin; Curcuminoids; Isolation; Radical coupling reaction; Zingiberaceae plants

Indexed keywords

5' METHOXYCURCUMIN; ANTIINFLAMMATORY AGENT; ANTIOXIDANT; BISABOCURCUMIN; CALEBIN A; CASSUMUNARIN A; CASSUMUNARIN B; CASSUMUNARIN C; CASSUMUNIN A; CASSUMUNIN B; CASSUMUNIN C; CURCUMIN; CURCUMINOID DERIVATIVE; DEMETHOXYCURCUMIN; DIDEMETHOXYCURCUMIN; LIPID; PHENOL DERIVATIVE; QUERCETIN; RESVERATROL; UNCLASSIFIED DRUG; VANILLIC ACID;

ALZHEIMER DISEASE; ANTIOXIDANT ACTIVITY; ARTICLE; CLINICAL CHEMISTRY; DRUG ACTIVITY; DRUG ISOLATION; DRUG POTENTIATION; DRUG SOLUBILITY; DRUG STRUCTURE; NONHUMAN; OXIDATION; PHOTOOXIDATION; PRIORITY JOURNAL; TAUTOMER;

EID: 84875385286     PISSN: 13816128     EISSN: 18734286     Source Type: Journal    
DOI: 10.2174/1381612811319110009     Document Type: Article

References (105)

1. Basnet P, Skalko-Basnet N. Curcumin: an anti-inflammatory molecule from a curry spice on the path to cancer treatment. Molecules 2011; 16: 4567-98.
2. Villar VM, Soria JM. Neuroprotective actions of curcumin. Novel Aspects of Neuroprotection. Trivandrum: Research Signpost 2010; pp. 3-47.
3. Sikora E, Bielak-Zmijewska A, Mosieniak G, Piwocka K. The promise of slow down ageing may come from curcumin. Curr Pharm Des 2010; 16: 884-92.
4. Shehzad A, Wahid F, Lee YS. Curcumin in cancer chemoprevention: molecular targets, pharmacokinetics, bioavailability, and clinical trials. Arch Pharm 2010; 343: 489-99.
5. Shehzad A, Lee YS. Curcumin: multiple molecular targets mediate multiple pharmacological actions-a review. Drugs Fut 2010; 35: 113-9.
6. Teiten MH, Eifes S, Dicato M, Diederich M. Curcumin-the paradigm of a multi-target natural compound with applications in cancer prevention and treatment. Toxins 2010; 2:128-62.
7. Bengmark S, Mesa MD, Gil A. Plant-derived health-the effects of turmeric and curcuminoids. Nutr Hosp 2009; 24: 273-281.
8. Aggarwal BB, Harikumar KB. Potential therapeutic effects of curcumin, the anti-inflammatory agent, against neurodegenerative, cardiovascular, pulmonary, metabolic, autoimmune, and neoplastic diseases. Int J Biochem Cell Biol 2009; 41: 40-59.
9. Pari L, Tewas D, Eckel J. Role of curcumin in health and disease. Arch Physiol Biochem 2008; 114: 127-49.
10. Hatcher H, Planalp R, Cho J, Torti FM, Torti SV. Curcumin: From ancient medicine to current clinical trials. Cell Mol Life Sci 2008; 65: 1631-52.
11. Rodwell C. Curcumin curries favour?. Nat Rev Cancer 2012; 24: 376.
12. Sharma OP. Antioxidant activity of curcumin and related compounds. Biochem Pharmacol 1976; 25: 1811-12.
13. Hengnaur R. Zingiberaceae. In Chemotaxonomie der pflauzen, band II, Basel and Stuttgart, Brirlhauser Verlag 1963; pp. 451-70.
14. Kuroyanagi M, Natori S. Some observation on curcuminoids from Zingiberaceae plants. Yakugaku Zasshi 1970; 90: 1467-70.
15. Uehara S, Yasuda I, Takaya K, Itokawa H. Terpenoids and curcuminoids for the rhizoma of Curcuma xanthorrhiza.Yakugaku Zasshi 1992; 112: 817-23.
16. Jitoe A, Masuda T, Tengah IPG, et al. Antioxidant activity of tropical ginger extracts and analysis of the contained curcuminoids. J Agric Food Chem 1992; 40: 1337-40.
17. Nakatani N, Jitoe A, Masuda T, Yonemori S. Constituents of Zingiberaceae. Part II. Flavonoid constituents of Zingiber zerunbet Smith. Agric Biol Chem 1991; 55: 455-60.
18. Gupta AP, Gupta MM, Kumar S. Simultaneous determination of curcuminoids in Curcuma samples using high performance thin layer chromatography. J Liq Chrom & Rel Technol 1999; 22: 1561-69.
19. Huang J, Ogihara Y, Gonda R, Takeda T. Novel biphenyl ether lignans from the rhizomes of Curcuma chuanyujin. Chem Pharm Bull 2000; 48: 1228-29.
20. Bos R, Windono T, Woerdenbag HJ, et al. HPLC-potodiode array detection analysis of curcuminoids in Curcuma species indigenous to Indonesia. Phytochem Anal 2007; 18: 118-22.
21. Wang D, Huang W, Shi Q, et al. Isolation and cytotoxic activity of compounds from the root of Curcuma wenyujin. Nat Prod Commun 2008; 3: 861-64.
22. Li R, Xiang C, Ye M, Li HF, Zhang X, Guo DA. Qualitative and quantitative analysis of curcuminoids in herbal medicines derived from Curcuma species. Food Chem 2011; 126: 1890-95.
23. Shamim A, Mohd A, Husain AS. New aliphatic constituents from the rhizomes of Curcuma oligantha Trimen var. oligantha. Int J Res in Ayurveda & Pharm 2011; 2: 797-800.
24. Ahmad S, Ali M, Ansari SH, Ahmed F. Chemical constituents from the rhizomes of Curcuma aromatica Salisb. Pharma Chemica 2011; 3: 505-11.
25. Tønnesen HH, Karlsen J. High-performance liquid chromatography of curcumin and related compounds. J Chromatogr 1983; 259: 367-71.
26. Coeren AC, Cikrici S, Cergel M, Bilsel G. Rapid quantitation of curcumin in turmeric via NMR and LC-tandem mass spectrometry. Food Chem 2009; 113: 1239-42.
27. Jin C, Kong W, Luo Y, et al. Development and validation of UPLC method for quality control of Curcuma longa Linn.: Fast simultaneous quantitation of three curcuminoids. J Pharm Biomed Anal 2010; 53: 43-9.
28. Uehara S, Yasuda I, Akiyama K, et al. Diarylheptanoids from the rhizomes of Curcuma xanthorrhiza and Alpinia officinarum. Chem Pharm Bull 1987; 35: 3298-304.
29. Li W, Wang S, Feng J, et al. Structure elucidation and NMR assignments for curcuminoids from the rhizomes of Curcuma longa. Magn Reson Chem 2009; 47: 902-8
30. Masuda T, Isobe J, Jitoe A, Nakatani N. Antioxidative curcuminoids from rhizomes of Curcuma xanthorrhiza. Phytochemistry 1992; 31: 3645-47.
31. Masuda T, Jitoe A. Antioxidative and antiinflammatry compounds from tropical gingers: Isolation, structure determination, and activities of cassumunins A, B, and C, new complex curcuminoids from Zingiber cassumunar. J Agric Food Chem 1994; 42: 1850-56.
32. Xiao YC, Xie J, Yu M, et al. Bisabocurcumin, a new skeleton curcuminoid from the rhizomes of Curcuma longa L. Chin Chem Lett 2011; 22: 1457-60
33. Ali MS, Banskota AH, Tezuka Y, Sakai I, Kadota S. Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx. Biol Pharm Bull 2001; 24: 525-28.
34. Masuda T, Jitoe A, Isobe J, Nakatani N, Yonemori S. Antioxidative and anti-inflammatory curcumin-related phenolics from rhizomes of Curcuma domestica. Phytochemistry 1993; 32: 1557-60.
35. Masuda T, Jitoe A, Mabry TJ. Isolation and structure determination of cassumunarins A, B, and C: new anti-inflammatory antioxidants from a tropical ginger, Zingiber cassumunar. J Am Oil Chem Soc 1995; 72: 1053-57.
36. Park SY, Kim DS. Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease. J Nat Prod 2002; 65: 1227-31.
37. Khurana A, Ho CT. High performance liquid chromatographic analysis of curcuminoids and their photo-oxidative decomposition. J Liq Chromatogr 1988; 11: 2295-304.
38. Tønnesen HH, Karlsen J, Beijersbergen von Henegouwen G. Studies on curcumin and curcuminoids. VIII, Photochemical stability of curcumin. Z Lebensmittel-Unter Forsch 1986; 183: 116-22.
39. Price LC, Buescher RW. Decomposition of turmeric curcuminoids as affected by light, solvent and oxygen. J Food Biochem 1996; 20: 125-33.
40. Grosjean D, Whitmore PM, De Moor CP, Cass GR, Druzik JR. Ozone fading of organic colorants: products and mechanism of the reaction of ozone with curcumin. Envir Sci Technol 1988; 22: 1357-61.
41. Schneider C, Amberg A, Feurle J, et al. 2-[(4"-Hydroxy-3'-methoxy)-phenyl]-4-(4"-hydroxy-3"-methoxy-phenyl)-8-hydroxy-6-oxo-3-oxabicyclo[3.3.0]-7-octene: unusual product of the soybean lipoxygenase-catalyzed oxygenation of curcumin. J Mol Cat B: Enzymatic 1998; 4: 219-227.
42. Toth G, Roth M, Weckerle B, Schreier P. Structural elucidation of two novel products from the soybean lipoxygenase-catalyzed dioxygenation of curcumin. Magn Reson Chem 2000; 38: 51-4.
43. Chauhan SMS, Kandadai AS, Jain N, Kumar A. Biomemetic oxidation of curcumin with hydrogen peroxide catalized by 5,10,15,20-tetraarylporphyrinatoiron (III) chlorides in dichloromethane. Chem Pharm Bull 2003; 51: 1345-47.
44. Tønnesen H H, Karsen J. Studies on curcumin and curcuminoids. V. Alkaline degradation of curcumin. Z Lebensmittel-Unter Forsch 1985, 180, 132-134.
45. Wang YJ, Pan MH, Cheng AL, et al. Stability of curcumin in buffer solutions and characterization of its degradation products. J Pharm Biomed Anal 1997; 15: 1867-76.
46. Prise LC, Buescher RW. Kinetics of alkaline degradation of the food pigments curcumin and curcuminoids. J Food Sci 1997; 62: 267-9.
47. Tønnesen HH. Studies of curcumin and curcuminoids, XXVIII. Solubility, chemical and photochemical stability of curcumin in surfactant solutions. Pharmazie 2002; 57: 820-24.
48. Esmaili M, Ghaffari SM, Moosavi-Movahedi Z, et al. Beta caseinmicelle as a nano vehicle for solubility enhancement of curcumin; food industry application. LWT-Food Sci Technol 2011; 44: 2166-72.
49. Tapal A, Tiku PK. Complexation of curcumin with soy protein isolate and its implications on solubility and stability of curcumin. Food Chem 2012; 130: 960-65.
50. Ahmed K, Li Y, McClements DJ, Xiao H. Nanoemulsion-and emulsion-based derivery systems for curcumin: Encapusulation and release properties. Food Chem 2012; 132: 799-807.
51. Gomez-Estaca J, Balaquer MP, Gavara R, Hernandez-Munoz P. Formation of zein nanoparticles by electrohydrodynamic atomization: Effect of the main processing variables and suitability for encapsulating the food coloring and active ingredient curcumin. Food Hydrocolloids 2012; 28: 82-91.
52. Mazzarino L, Travelet C, Ortaga-Murillo S, et al. Elaboration of chitosan-coated noanoparticles loaded with curcumin for mucoadhesive applications. J Colloid Interface Sci 2012; 370: 58-66.
53. Chen Y, Wu Q, Zhang Z, Yuan L, Liu X, Zhou L. Preparation of curcumin-loaded liposomes and evaluation of their skin permeation and pharmacodynamics. Molecules 2012; 17: 5972-87.
54. Yallapu MM, Othman SF, Curtis ET, et al. Curcumin-loaded magnetic nanoparticles for breast cancer therapeutics and imaging applications. Int J Nanomedicine 2012; 7: 1761-79.
55. Kumar S, Narain U, Tripathi S, Misra K. Syntheses of curcumin bioconjugates and study of their antibacterial activities against β-lactamase producing microorganisms. Bioconjug Chem 2001; 12: 464-69.
56. Dubey SK, Sharma AK, Narain U, Mistra K, Pati U. 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 antiproliferative properties. Eur J Med Chem 2008; 43: 1837-46.
57. Vijayakumar GR, Manohar B, Divakar S. Amylogulucosidasecatalysed synthesis of curcumin-bis-α-D-glucoside-a response surface methodological study. Eur Food Res Technol 2006; 223: 725-730.
58. Kei S, Hara T, Hamada H, Hamada H. Synthesis of curcumin α-maltooligosides through biological glycosylation with Strophanthus gratuscell culture and cyclodextrin glucanotransferase. Tetrahedron Lett 2007; 48: 4029-32.
59. Safavy A, Raisch KP, Mantena S, et al. Design and development of water-soluble curcumin conjugates as potential anticancer agents. J Med Chem 2007; 50: 6284-8.
60. Osawa T, Sugiyama Y, Inayoshi M, Kawakishi S. Antioxidative activity of tetrahydrocurcuminoids. Biosci Biotech Biochem 1995; 59: 1609-12.
61. Wright JS. Predicting the antioxidant activity of curcumin and curcuminoids. J Mol Struct (Theochem) 2002; 591; 207-17.
62. Payton F, Sandusky P, Alworth W L. NMR study of the solution structure of curcumin. J Nat Prod 2007; 70: 143-66.
63. Jovanovic SV, Steenken S, Boone CW, Simic M G. H-atom transfer is a preferred antioxidant mechanism of curcumin. J Am Chem Soc 1999; 121: 9677-81.
64. Jovanovic SV, Boone CW, Steenken S, Trinola M, Kaskey RB. How curcumin works preferentially with water soluble antioxidants. J Am Chem Soc 2001; 123: 3064-68.
65. Sun YM, Zhang HY, Chen DZ, Liu CB. Theoretical elucidation on the antioxidant mechanism of curcumin: A DFT study. Organic Lett 2002; 4: 2909-11.
66. Priyadarsini KI, Maity DK, Naik G H, et al. Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Rad Biol Med 2003; 35: 475-84.
67. Litwinienko G, Ingold KU. Abnormal solvent effects on hydrogen atom abstraction. 2. Resolution of the curcumin antioxidant controversy. The role of sequential proton loss electron transfer. J Org Chem 2004; 69: 5888-96
68. Ohara K, Mizukami W, Tokunaga A, Nagaoka SI, Ueno H, Mukai K. Kinetic study of the mechanism of free-radical scavenging action in curcumin: effects of solvent and pH. Bull Chem Soc Jpn 2005; 78: 615-21.
69. Galano A, Alvarez-Diduk R, Ramirez-Silva MT, Alarcon-Aggeles G, Rojas-Hernandez A. Role of the reacting free radicals on the antioxidant mechanism of curcumin. Chem Phys 2009; 363:13-23.
70. Feng JY, Liu ZQ. Phenolic and enolic hydroxyl groups in curcumin: Which plays the major role in scavenging radicals? J Agric Food Chem 2009; 57: 11041-46.
71. Toda S, Miyase T, Arichi H, Tanizawa H, Takino Y. Natural antioxidants III. Antioxidative components isolated from rhizome of Curcuma longa L. Chem Pharm Bull 1985; 33: 1725-28.
72. Ruby AJ, Kuttan G, Babu KD, Rajasekharan KN, Kuttan R. Antitumour and antioxidant activity of natural curcuminoids. Cancer Lett 1995; 94: 79-83.
73. Somparn P, Phisalaphong C, Nakornchai S, Unchern S, Morales NP. Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biol Pharm Bull 2007; 30: 71-8.
74. Salimath BP, Sundareshi CS, Srinivas L. Dietary components inhibit lipid peroxidation in erythrocyte membrane. Nutrition Res 1986; 6: 1171-78.
75. Toda S, Ohnishi M, Kimura M, Nakashima K. Action of curcuminouds on the hemolysis and lipid oxidation of mouse erythrocytes induced by hydrogen peroxide. J Ethnophamacol 1988; 23: 105-8.
76. Shalini VK, Srinivas L. Lipid peroxide induced DNA damage: protection by turmeric (Curcuma longa). Mol Cell Biochem 1987; 77: 3-10.
77. Sahu SC, Washington MC. Effect of ascorbic acid and curcumin on quercetin-inducd nuclear DNA damage, lipid oxidation and protein degradation. Cancer Lett 1992; 63: 237-41.
78. Tønnesen HH, Greenhill JV. Studies on curcumin and curcuminoids. XXII: Curcumin as a reducing agent and as a radical scavenger. Int J Pham 1992; 87: 79-87.
79. Sreejayan RMNA. Curcumin inhibits iron-dependent lipid peroxidation. Int J Pham 1993; 100: 93-7.
80. Reddy ACP, Lokesh BR. Studies on the inhibitory effects of curcumin and eugenol on the formation of reactive oxygen species and the oxidation of ferrous iron. Mol Cell Biochem 1994; 137: 1-8.
81. Noguchi N, Komuo E, Niki E, Willson RL. Action of curcumin as an antioxidant against lipid oxidation. Yukagaku 1994; 43: 1045-51.
82. Reddy ACP, Lokesh BR. Studies on spice principles as antioxidants in the inhibition of lipid peroxidation of rat microsomes. Mol Cell Biochem 1992; 111: 117-24.
83. Rajakumar DV, Rao MNA. Antioxidant properties of dehydrozingerone and curcumin in rat brain homogenates. Mol Cell Biochem 1994; 140: 73-79.
84. Sreejayan N, Rao MNA, Priyadarsini KI, Devasagayam TPA. Inhibition of radiation-induced lipid peroxidation by curcumin. Int J Pharm 1997; 151: 127-30.
85. Unnikrishnan MK, Rao MNA. Inhibition of nitrite induced oxidation of hemoglobin by curcuminoids. Pharmazie 1995; 50: 490-92.
86. Kunchandy E, Rao MNA. Oxygen radical scavenging activity of curcumin. Int J Pharm 1990; 58: 237-40.
87. Toniolo R, Di NF, Susmel S, et al. Quenching of superoxide ions by curcumin. A mechanistic study in acetonitrile. Ann Chim 2002; 92: 281-288.
88. Das KC, Das C K. Curcumin (diferuloylmethane), a singlet oxygen (1O2) quencher. Biochem Biophys Res Commun 2002; 295: 62-6.
89. Kim JE, Kim AR, Chung HY, et al. In vitro peroxynitrite scavenging activity of diarylheptanoids from Curcuma longa. Phytothr Res 2003; 17: 481-4.
90. Masuda T, Jitoe A. Anti-inflammatory antioxidants from medicinal gingers: new complex cucuminoids from Zingiber cassumunar. In Proceedings of the International Symposium on Natural Antioxidants, Chicago, AOCS Press 1996, pp.99-108.
91. Masuda T, Matsumura H, Oyama Y, et al. Synthesis of (+/-)-Cassumunins A and B, New curcuminoid antioxidants having protective activity of the living cell against oxidative damage. J Nat Prod 1998; 61: 609-13
92. Oyama Y, Masuda T, Nakata M, et al. Protective actions of 5'-nalkylated curcumins on living cells suffering from oxidative stress. Eur J Pharmacol 1998; 360: 65-71.
93. Kadoma Y, Fujisawa S. Comparative radical-scavenging activity of curcumin and tetrahydrocurcumin with thiols as measured by the induction period method. In Vivo 2007; 21: 979-82.
94. Aftab N, Vieira A. Antioxidant activities of curcumin and combinations of this curcuminoid with other phytochemicals. Phytother Res 2010; 24: 500-2.
95. Pincyhuk I, Shoval H, Bor A, Schnitzer E, Donan Y, Lichtenberg D. Ranking antioxidants based on their effect on human serum lipids peroxidation. Chem Phys Lipids 2011; 164: 42-48.
96. Kolodziejczyk J. Olas B, Saluk-Juszczak J, Wachowicz B. Antioxidative properties of curcumin in the protection of blood platelets against oxidation stress in vitro. Platelets 2011; 22: 270-76.
97. Barzegar A, Moosavi-Movahedi AA. Intracellular ROS protection efficiency and free radical-scavenging activity of curcumin. PloS One 2011; 6: e26012.
98. Hung WL, Ho CT, Hwang LS. Inhibitory activity of natural occurring antioxidants on thiyl radical-induced trans-arachidonic acid formation. J Agric Food Chem 2011; 59: 1968-73.
99. Naik SR, Thakare VN, Patil SR. Protective effect of curcumin on experimentally induced inflammation, hepatotoxicity, and cardiotoxicity in rats: Evidence of its antioxidant property. Exp Toxicol Pathol 2010; 63: 419-31.
100. Hotta H, Nagao S, Ueda M, et al. Higher radical scavenging activities of polyphenolic antioxidants can be ascribed to chemical reactions following their oxidation. Biochim Biophy Acta 2002; 1572: 123-32.
101. Masuda T, Toi Y, Bando H, Maekawa T, Takeda Y, Yamaguchi H. Structural identification of new curcumin dimers and their contribution to the antioxidant mechanism. J Agric Food Chem 2002; 50: 2524-30 (2002)
102. Masuda T, Hidaka K, Shinohara A, et al. Chemical studies on antioxidant mechanism of curcuminoid: Analysis of radical reaction products from curcumin. J Agric Food Chem 1999; 47: 71-7.
103. Masuda T, Maekawa T, Hidaka K, et al. Chemical studies on antioxidant mechanism of curcumin: Analysis of oxidative produces from curcumin and linoleate. J Agric Food Chem 2001; 49: 2539-2547.
104. Masuda T, Yamada K, Maekawa T. Takeda Y, Yamaguchi H. Antioxidant mechanism studies on ferulic acid, Identification of oxidative coupling products from methyl ferulate and linoleate. J Agric Food Chem 2006; 54: 6069-74.
105. Masuda T, Akiyama J, Fujimoto A, et al. Antioxidation reaction mechanism studies of phenolic lignans, Identification of antioxidation products of secoisolariciresinol from lipid oxidation. Food Chem 2010; 123: 442-50.