Inhibition of lipoxygenase-1 by tetrahydrocurcumin

European Food Research and Technology

Volumn 233, Issue 4, 2011, Pages 561-568

  Sneharani, A H ^a   Singh, Sridevi Annapurna ^a   Srinivas, P ^a   Rao, A G Appu ^a  

^a CENTRAL FOOD TECHNOLOGICAL RESEARCH INSTITUTE   (India)

Author keywords

Lipoxygenase; Redox inhibition; Spectroscopic measurements; Stability; Tetrahydrocurcumin

Indexed keywords

ANTI-INFLAMMATORIES; AQUEOUS MEDIUM; COFACTORS; CURCUMIN; CURCUMIN DERIVATIVES; INFLAMMATORY CONDITIONS; LINEAR TYPES; LIPOXYGENASE-1; LIPOXYGENASES; MOLECULAR DOCKING SIMULATIONS; PARENT COMPOUNDS; PHYSIOLOGICAL PH; SPECTROSCOPIC MEASUREMENTS; SPECTROSCOPIC STUDIES; TETRAHYDROCURCUMIN;

CONVERGENCE OF NUMERICAL METHODS; SPECTROSCOPIC ANALYSIS;

PH;

EID: 80052957948     PISSN: 14382377     EISSN: 14382385     Source Type: Journal    
DOI: 10.1007/s00217-011-1541-6     Document Type: Article

References (32)

1. Corson TW, Crews CM (2007) Molecular understanding and modern application of traditional medicines: triumphs and trials. Cell 130: 769-774.
2. Anand P, Kunnumakkara AB, Newman RA, Aggarwal BB (2007) Bioavailability of curcumin: problems and promises. Mol Pharmacol 4: 807-818.
3. Wang YJ, Pan MH, Cheng AL, Lin LI, Ho YS, Hsieh CY, Lin JK (1997) Stability of curcumin in buffer solutions and characterization of its degradation products. J Pharm Biomed Anal 15: 1867-1876.
4. Szefel J, Piotrowska M, Kruszewski WJ, Jankun J, Łysiak-Szydłowska W, Skrzypczak-Jankun E (2011) Eicosanoids in prevention and management of diseases. Curr Mol Med 11: 13-25.
5. Began G, Sudharshan E, Rao AGA (1998) Inhibition of lipoxygenase 1 by phosphatidylcholine micelles-bound curcumin. Lipids 33: 1223-1228.
6. Prasad NS, Raghavendra R, Lokesh BR, Naidu KA (2004) Spice phenolics inhibit human PMNL 5-lipoxygenase. Prostaglandins Leukot Essent Fatty Acids 70: 521-528.
7. 2, cyclooxygenases and 5-lipoxygenase. Carcinogenesis 25: 1671-1679.
8. Gardner HW (1991) Recent investigations into the lipoxygenase pathway of plants. Biochim Biophys Acta 1084: 221-239.
9. Skrzypczak-Jankun E, Joanna CW, Steven SH, Jankun J (2007) Lipoxygenases-a challenging problem in enzyme inhibition and drug development. Curr Enzym Inhib 3: 119-132.
10. Pan MH, Huang TM, Lin JK (1999) Biotransformation of curcumin through reduction and glucuronidation in mice. Drug Metab Dispos 27: 486-494.
11. Khopde SM, Priyadarshini KI, Guha SN, Satav JG, Venkatesan P, Rao MNA (2000) Inhibition of radiation-induced lipid peroxidation by tetrahydrocurcumin: possible mechanism by pulse radiolysis. Biosci Biotechnol Biochem 64: 503-509.
12. Majeed M, Badmaev V, Shimakumar U, Rajendran R (1990) Curcuminoids: antioxidant phytonutrients. Nutriscience Publishers Inc, Piscataway.
13. Osawa T, Sugiyama Y, Inayoshi M, Kawakishi S (1995) Antioxidant activity of tetrahydrocurcuminoids. Biosci Biotechnol Biochem 59: 1609-1612.
14. Sugiyama Y, Kawakishi S, Osawa T (1996) Involvement of the β-diketone moiety in the antioxidative mechanism of tetrahydrocurcumin. Biochem Pharmacol 52: 519-525.
15. Nakamaru Y, Ohto Y, Murakami A, Osawa T, Ohigashi H (1998) Inhibitory effects of curcumin and tetrahydrocurcuminoids on the tumor promoter-induced reactive oxygen species generation in leuckocytes in vitro and in vivo. Jpn J Cancer Res 89: 361-370.
16. Kim JM, Araki S, Kim DJ, Park CB, Takasuka N, Baba-Toriyama H, Ota T, Nir Z, Khachika F, Shimidzu N, Tanaka Y, Ozawa T, Uraji T, Murakoshi M, Nishino H, Tsuda H (1998) Chemopreventive effects of carotenoids and curcumin on mouse colon carcinogenesis after 1, 2-dimethylhydrazine initiation. Carcinogenesis 9: 81-85.
17. Axelrod B, Cheesbrough TM, Laakso S (1981) Lipoxygenase from soybeans. Methods Enzymol 71: 441-451.
18. Sudharshan E, Rao AGA (1997) Rapid method to separate the domains of soybean lipoxygenase 1: identification of the interdomain interactions. FEBS Lett 406: 184-188.
19. Galpini JR, Tielens LGM, Veldink GA, Vliegenthart JFG, Bolding J (1976) On the interaction of some catechol derivatives with the iron atom of soybean lipoxygenase. FEBS Lett 69: 178-182.
20. Skrzypczak-Jankun E, Zhou K, Jankun J (2003) Inhibition of lipoxygenase by (-)-epigallocatechin gallate: X-ray analysis at 2. 1 Å reveals degradation of EGCG and shows soybean LOX-3 complex with EGC instead. Int J Mol Med 12: 415-420.
21. Thomsen R, Christensen MH (2006) MolDock: a new technique for high-accuracy molecular docking. J Med Chem 49: 3315-3321.
22. Skrzypczak-Jankun E, Zhou K, McCabe NP, Selman SH, Jankun J (2003) Structure of curcumin in complex with lipoxygenase and its significance in cancer. Int J Mol Med 12: 17-24.
23. Spaapen LJM, Veldink GA, Liefkens TJ, Vliegenthart JFG, Kay CM (1979) Circular dichroism of lipoxygenase-1 from soybeans. Biochim Biophys Acta 574: 301-311.
24. Mahesha HG, Singh SA, Rao AGA (2007) Inhibition of lipoxygenase by soy isoflavones: evidence of isoflavones as redox inhibitors. Arch Biochem Biophys 461: 176-185.
25. van der Zee J, Eling TE, Mason RP (1989) Formation of free-radical metabolites in the reaction between soybean lipoxygenase and its inhibitors. An ESR study. Biochemistry 28: 8363-8836.
26. Skrzypczak-Jankun E, McCabe NP, Selman SH, Jankun J (2000) Curcumin inhibits lipoxygenase by binding to its central cavity: theoretical and X-ray evidence. Int J Mol Med 6: 521-526.
27. Skrzypczak-Jankun E, Bross RA, Carroll RT, Dunham WR, Funk MO Jr (2001) Three-dimensional structure of a purple lipoxygenase. J Am Chem Soc 123: 10814-10820.
28. Borbulevych OY, Jankun J, Selman SH, Skrzypczak-Jankun E (2004) Lipoxygenase interactions with natural flavonoid, quercetin, reveal a complex with protocatechuic acid in its x-ray structure at 2. 1 Å resolution. Proteins 54: 13-19.
29. Skrzypczak-Jankun E, Borbulevych OY, Jankun J (2004) Soybean lipoxygenase-3 in complex with 4-nitrocatechol. Acta Crystallogr D Biol Crystallogr 60: 613-615.
30. Okada K, Wangpoengtrskul C, Tanaka T, Toyokuni S, Uchida K, Osawa T (2001) Curcumin and especially tetrahydrocurcumin ameliorate oxidative stress-induced hepatotoxicity. J Nutr 131: 2090-2095.
31. Venkatesan P, Rao MNA (2000) Structure-activity relationship for the inhibition of lipid peroxidation and scavenging of free radicals by synthetic symmetrical curcumin analogues. J Pharm Pharmacol 52: 1123-1128.
32. Tappel AL, Boyer PD, Lundberg WO (1952) The reaction mechanism of soybean lipoxidase. J Biol Chem 199: 267-281.