全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...

Structure-Function Elucidation of Antioxidative and Prooxidative Activities of the Polyphenolic Compound Curcumin

DOI: 10.1155/2014/396708

Full-Text   Cite this paper   Add to My Lib

Abstract:

Phenolic compounds have been very well known for their antioxidant properties, owing to their unique ability to act as free radical scavengers which, in turn, is an outstanding attribute of their unique biochemical structure. Recent accumulating lines of evidence inculcate sustainable interest and curiosity towards the chemoprotective nature of the natural polyphenolic compound curcumin (diferuloylmethane) against oxidative stress-mediated disorders. Curcumin is naturally found as a constituent of dietary spices called turmeric, extracted from the plant Curcuma longa. However, like every phenolic antioxidant, curcumin possesses a concentration and medium dependent anti- and pro-oxidant behaviour. A detailed study of the structure-function analysis and the understanding of the mode of action of curcumin as well as its chemical analogues is thus essential to understand the selective biochemical consequences of curcumin. Moreover, the presence of transition metal ions, route of administration, and localized tissue are also the vital decisive factors to determine curcumin behaviour. With this viewpoint, this paper sheds lights on the medium dependent prooxidative and antioxidative attributes of curcumin. Further, with respect to emergence of nanocarriers, a brief discussion focusing on the biochemical effect exertion of curcumin chiefly due to targeted and slow release has also been added towards the end. 1. Introduction Phenolic compounds are widely accepted and recommended for their antioxidant activities [1–3].The chemical structure of the phenolic compounds imparts them the ability to serve as free radical scavengers. A phenolic compound consists of a benzene ring and an alcoholic hydroxyl group, which are the defining features of its acidic nature. The type of the compound to be reduced, the degree of methoxylation, and the number of the hydroxyl groups present are some of the vital parameters that determine the antioxidant activity of a phenolic antioxidant. A diligent look into the structure of typical alcohol and a phenol leads to the conclusive finding that, in alcohols, the –OH group is bonded to saturated carbon atom while, in case of phenols, the hydroxyl (–OH) group is bonded to an unsaturated carbon atoms and this is clearly an indication that release of hydrogen ion is easier from the phenols than from the corresponding alcohols. That’s why phenols are widely known by the name carbolic acid. Furthermore, pKa value for phenols is also more than that of the typical alcohols, which makes phenol a stronger acid than the alcohols [4]. A phenolic

References

[1]  H. M. Ali, A. Abo-Shady, H. A. Sharaf Eldeen, H. A. Soror, W. G. Shousha, et al., “Structural features, kinetics and SAR study of radical scavenging and antioxidant activities of phenolic and anilinic compounds,” Chemistry Central Journal, vol. 7, no. 1, article 53, 2013.
[2]  M. A. Soobrattee, V. S. Neergheen, A. Luximon-Ramma, O. I. Aruoma, and T. Bahorun, “Phenolics as potential antioxidant therapeutic agents: mechanism and actions,” Mutation Research, vol. 579, no. 1-2, pp. 200–213, 2005.
[3]  C. A. Rice-Evans, N. J. Miller, and G. Paganga, “Antioxidant properties of phenolic compounds,” Trends in Plant Science, vol. 2, no. 4, pp. 152–159, 1997.
[4]  J. Clark, The Acidity of Phenol, ChemGuide, 2007.
[5]  M. Schaffer, P. M. Schaffer, J. Zidan, and G. B. Sela, “Curcuma as a functional food in the control of cancer and inflammation,” Current Opinion in Clinical Nutrition and Metabolic Care, vol. 14, no. 6, pp. 588–597, 2011.
[6]  Y. Shen, C. Han, X. Chen, X. Hou, and Z. Long, “Simultaneous determination of three Curcuminoids in Curcuma wenyujin Y.H.chen et C.Ling. by liquid chromatography-tandem mass spectrometry combined with pressurized liquid extraction,” Journal of Pharmaceutical and Biomedical Analysis, vol. 81-82, pp. 146–150, 2013.
[7]  P. Anand, S. G. Thomas, A. B. Kunnumakkara et al., “Biological activities of curcumin and its analogues (congeners) made by man and Mother Nature,” Biochemical Pharmacology, vol. 76, no. 11, pp. 1590–1611, 2008.
[8]  S. C. Gupta, S. Patchva, and B. B. Aggarwal, “Therapeutic roles of curcumin: lessons learned from clinical trials,” The AAPS Journal, vol. 15, no. 1, pp. 195–218, 2012.
[9]  S. C. Gupta, S. Patchva, W. Koh, and B. B. Aggarwal, “Discovery of curcumin, a component of golden spice, and its miraculous biological activities,” Clinical and Experimental Pharmacology and Physiology, vol. 39, no. 3, pp. 283–299, 2012.
[10]  W. M. Weber, L. A. Hunsaker, S. F. Abcouwer, L. M. Deck, and D. L. Vander Jagt, “Anti-oxidant activities of curcumin and related enones,” Bioorganic and Medicinal Chemistry, vol. 13, no. 11, pp. 3811–3820, 2005.
[11]  P. Venkatesan and M. N. Rao, “Structure-activity relationships for the inhibition of lipid peroxidation and the scavenging of free radicals by synthetic symmetrical curcumin analogues,” Journal of Pharmacy and Pharmacology, vol. 52, no. 9, pp. 1123–1128, 2000.
[12]  S. V. Jovanovic, S. Steenken, C. W. Boone, and M. G. Simic, “H-atom transfer is a preferred antioxidant mechanism of curcumin,” Journal of the American Chemical Society, vol. 121, no. 41, pp. 9677–9681, 1999.
[13]  O. P. Sharma, “Antioxidant activity of curcumin and related compounds,” Biochemical Pharmacology, vol. 25, no. 15, pp. 1811–1812, 1976.
[14]  K. C. Das and C. K. Das, “Curcumin (diferuloylmethane), a singlet oxygen ( ) quencher,” Biochemical and Biophysical Research Communications, vol. 295, no. 1, pp. 62–66, 2002.
[15]  S. Mishra, N. Kapoor, A. M. Ali et al., “Differential apoptotic and redox regulatory activities of curcumin and its derivatives,” Free Radical Biology and Medicine, vol. 38, no. 10, pp. 1353–1360, 2005.
[16]  A. Kunwar, A. Barik, S. K. Sandur, and I. K. Priyadarsini, “Differential antioxidant/pro-oxidant activity of dimethoxycurcumin, a synthetic analogue of curcumin,” Free Radical Research, vol. 45, no. 8, pp. 959–965, 2011.
[17]  T. Atsumi, S. Fujisawa, and K. Tonosaki, “Relationship between intracellular ROS production and membrane mobility in curcumin- and tetrahydrocurcumin-treated human gingival fibroblasts and human submandibular gland carcinoma cells,” Oral Diseases, vol. 11, no. 4, pp. 236–242, 2005.
[18]  C. Syng-Ai, A. L. Kumari, and A. Khar, “Effect of curcumin on normal and tumor cells: role of glutathione and bcl-2,” Molecular Cancer Therapeutics, vol. 3, no. 9, pp. 1101–1108, 2004.
[19]  A. Banerjee, A. Kunwar, B. Mishra, and K. I. Priyadarsini, “Concentration dependent antioxidant/pro-oxidant activity of curcumin. Studies from AAPH induced hemolysis of RBCs,” Chemico-Biological Interactions, vol. 174, no. 2, pp. 134–139, 2008.
[20]  M. Yoshino, M. Haneda, M. Naruse et al., “Prooxidant activity of curcumin: copper-dependent formation of 8-hydroxy-2′-deoxyguanosine in DNA and induction of apoptotic cell death,” Toxicology in Vitro, vol. 18, no. 6, pp. 783–789, 2004.
[21]  R. Motterlini, R. Foresti, R. Bassi, and C. J. Green, “Curcumin, an antioxidant and anti-inflammatory agent, induces heme oxygenase-1 and protects endothelial cells against oxidative stress,” Free Radical Biology and Medicine, vol. 28, no. 8, pp. 1303–1312, 2000.
[22]  M. C. Kou, S. Y. Chiou, C. Y. Weng, L. Wang, C. T. Ho, and M. -J. Wu, “Curcuminoids distinctly exhibit antioxidant activities and regulate expression of scavenger receptors and heme oxygenase-1,” Molecular Nutrition & Food Research, vol. 57, no. 9, pp. 1598–1610, 2013.
[23]  S. Aggarwal, H. Ichikawa, Y. Takada, S. K. Sandur, S. Shishodia, and B. B. Aggarwal, “Curcumin (diferuloylmethane) down-regulates expression of cell proliferation and antiapoptotic and metastatic gene products through suppression of IκBα kinase and Akt activation,” Molecular Pharmacology, vol. 69, no. 1, pp. 195–206, 2006.
[24]  F. Zhang, N. K. Altorki, J. R. Mestre, K. Subbaramaiah, and A. J. Dannenberg, “Curcumin inhibits cyclooxygenase-2 transcription in bile acid- and phorbol ester-treated human gastrointestinal epithelial cells,” Carcinogenesis, vol. 20, no. 3, pp. 445–451, 1999.
[25]  A. Goel, C. R. Boland, and D. P. Chauhan, “Specific inhibition of cyclooxygenase-2 (COX-2) expression by dietary curcumin in HT-29 human colon cancer cells,” Cancer Letters, vol. 172, no. 2, pp. 111–118, 2001.
[26]  A. J. Ruby, G. Kuttan, K. Dinesh Babu, K. N. Rajasekharan, and R. Kuttan, “Anti-tumour and antioxidant activity of natural curcuminoids,” Cancer Letters, vol. 94, no. 1, pp. 79–83, 1995.
[27]  M. M. Chan, H. I. Huang, M. R. Fenton, and D. Fong, “In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties,” Biochemical Pharmacology, vol. 55, no. 12, pp. 1955–1962, 1998.
[28]  Y.-J. Wang, M.-H. Pan, A.-L. Cheng et al., “Stability of curcumin in buffer solutions and characterization of its degradation products,” Journal of Pharmaceutical and Biomedical Analysis, vol. 15, no. 12, pp. 1867–1876, 1997.
[29]  F. Payton, P. Sandusky, and W. L. Alworth, “NMR study of the solution structure of curcumin,” Journal of Natural Products, vol. 70, no. 2, pp. 143–146, 2007.
[30]  P. Somparn, C. Phisalaphong, S. Nakornchai, S. Unchern, and N. P. Morales, “Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives,” Biological and Pharmaceutical Bulletin, vol. 30, no. 1, pp. 74–78, 2007.
[31]  J. S. Jurenka, “Anti-inflammatory properties of curcumin, a major constituent of Curcuma longa: a review of preclinical and clinical research,” Alternative Medicine Review, vol. 14, no. 2, pp. 141–153, 2009.
[32]  S. Shishodia, G. Sethi, and B. B. Aggarwal, “Curcumin: getting back to the roots,” Annals of the New York Academy of Sciences, vol. 1056, pp. 206–217, 2005.
[33]  J. Chen, W. Da, D. Zhang, Q. Liu, and J. Kang, “Water-soluble antioxidants improve the antioxidant and anticancer activity of low concentrations of curcumin in human leukemia cells,” Pharmazie, vol. 60, no. 1, pp. 57–61, 2005.
[34]  H.-C. Huanga, C.-J. Lin, W.-J. Liu, R.-R. Jiang, and Z.-F. Jiang, “Dual effects of curcumin on neuronal oxidative stress in the presence of Cu(II),” Food and Chemical Toxicology, vol. 49, no. 7, pp. 1578–1583, 2011.
[35]  A. I. Ghoneim, “Effects of curcumin on ethanol-induced hepatocyte necrosis and apoptosis: implication of lipid peroxidation and cytochrome c,” Naunyn-Schmiedeberg's Archives of Pharmacology, vol. 379, no. 1, pp. 47–60, 2009.
[36]  C.-L. Lin and J.-K. Lin, “Curcumin: a potential cancer chemopreventive agent through suppressing NF-κB signaling,” Journal of Cancer Molecules, vol. 4, no. 1, pp. 11–16, 2008.
[37]  E.-M. Strasser, B. Wessner, N. Manhart, and E. Roth, “The relationship between the anti-inflammatory effects of curcumin and cellular glutathione content in myelomonocytic cells,” Biochemical Pharmacology, vol. 70, no. 4, pp. 552–559, 2005.
[38]  J.-H. Woo, Y.-H. Kim, Y.-J. Choi et al., “Molecular mechanisms of curcumin-induced cytotoxicity: induction of apoptosis through generation of reactive oxygen species, down-regulation of Bcl-XL and IAP, the release of cytochrome c and inhibition of Akt,” Carcinogenesis, vol. 24, no. 7, pp. 1199–1208, 2003.
[39]  G. Galati, O. Sabzevari, J. X. Wilson, and P. J. O'Brien, “Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics,” Toxicology, vol. 177, no. 1, pp. 91–104, 2002.
[40]  H. Ahsan, N. Parveen, N. U. Khan, and S. M. Hadi, “Pro-oxidant, anti-oxidant and cleavage activities on DNA of curcumin and its derivatives demethoxycurcumin and bisdemethoxycurcumin,” Chemico-Biological Interactions, vol. 121, no. 2, pp. 161–175, 1999.
[41]  J. Ravindran, G. V. Subbaraju, M. V. Ramani, B. Sung, and B. B. Aggarwal, “Bisdemethylcurcumin and structurally related hispolon analogues of curcumin exhibit enhanced prooxidant, anti-proliferative and anti-inflammatory activities in vitro,” Biochemical Pharmacology, vol. 79, no. 11, pp. 1658–1666, 2010.
[42]  J. Fang, J. Lu, and A. Holmgren, “Thioredoxin reductase is irreversibly modified by curcumin: a novel molecular mechanism for its anticancer activity,” The Journal of Biological Chemistry, vol. 280, no. 26, pp. 25284–25290, 2005.
[43]  N. Jurrmann, R. Brigelius-Flohé, and G.-F. B?l, “Curcumin blocks interleukin-1 (IL-1) signaling by inhibiting the recruitment of the IL-1 receptor-associated kinase IRAK in murine thymoma EL-4 cells,” Journal of Nutrition, vol. 135, no. 8, pp. 1859–1864, 2005.
[44]  S. K. Sandur, H. Ichikawa, M. K. Pandey et al., “Role of pro-oxidants and antioxidants in the anti-inflammatory and apoptotic effects of curcumin (diferuloylmethane),” Free Radical Biology and Medicine, vol. 43, no. 4, pp. 568–580, 2007.
[45]  H. Ahsan and S. M. Hadi, “Strand scission in DNA induced by curcumin in the presence of Cu(II),” Cancer Letters, vol. 124, no. 1, pp. 23–30, 1998.
[46]  M. H. Leung, T. Harada, and T. W. Kee, “Delivery of curcumin and medicinal effects of the copper(II)-curcumin complexes,” Current Pharmaceutical Design, vol. 19, no. 11, pp. 2070–2083, 2013.
[47]  G. Viswanath, A. Jithan, and V. M. Reddy, “Development of new delivery strategies to increase bioavailability of curcumin,” International Journal of Pharmaceutical Sciences and Nanotechnology, vol. 1, no. 4, pp. 335–340, 2009.
[48]  P. Anand, A. B. Kunnumakkara, R. A. Newman, and B. B. Aggarwal, “Bioavailability of curcumin: problems and promises,” Molecular Pharmaceutics, vol. 4, no. 6, pp. 807–818, 2007.
[49]  A. Zanotto-Filho, K. Coradini, E. Braganhol, et al., “Curcumin-loaded lipid-core nanocapsules as a strategy to improve pharmacological efficacy of curcumin in glioma treatment,” European Journal of Pharmaceutics and Biopharmaceutics, vol. 83, pp. 156–167, 2013.
[50]  N. Zhoua, X. Zanb, Z. Wang, Z. D, et al., “Galactosylated chitosan- polycaprolactone nanoparticles for hepatocyte-targeted delivery of curcumin,” Carbohydrate Polymers, vol. 94, no. 1, pp. 420–429, 2013.
[51]  A. P. Ranjan, A. Mukerjee, L. Helson, and J. K. Vishwanatha, “Scale up, optimization and stability analysis of Curcumin C3 complex-loaded nanoparticles for cancer therapy,” Journal of Nanobiotechnology, vol. 10, no. 38, 2012.
[52]  M. M. Yallapu, M. Jaggi, and S. C. Chauhan, “Curcumin nanomedicine a road to cancer therapeutics,” Current Pharmaceutical Design, vol. 19, no. 11, pp. 1994–2010, 2013.
[53]  H. Sasaki, Y. Sunagawa, K. Takahashi et al., “Innovative preparation of curcumin for improved oral bioavailability,” Biological and Pharmaceutical Bulletin, vol. 34, no. 5, pp. 660–665, 2011.
[54]  G. Leonarduzzi, B. Sottero, and G. Poli, “Targeting tissue oxidative damage by means of cell signaling modulators: the antioxidant concept revisited,” Pharmacology and Therapeutics, vol. 128, no. 2, pp. 336–374, 2010.

Full-Text

comments powered by Disqus

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133

WeChat 1538708413