Antioxidant, free radical-scavenging, and NF-κB-inhibitory activities of phytosteryl ferulates: Structure-activity studies

Journal of Pharmacological Sciences

Volumn 111, Issue 4, 2009, Pages 328-337

  Islam, Md Shafiqul ^a   Yoshida, Hiroshi ^a   Matsuki, Naoaki ^a   Ono, Kenichiro ^a   Nagasaka, Reiko ^b   Ushio, Hideki ^b   Guo, Ying ^c   Hiramatsu, Toshiyuki ^c   Hosoya, Takamitsu ^c   Murata, Takahisa ^a   Hori, Masatoshi ^a   Ozaki, Hiroshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKYO UNIVERSITY OF MARINE SCIENCE AND TECHNOLOGY   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Antioxidant; Cycloartenyl ferulate; NF B; Phytosteryl ferulate; Reactive oxygen species (ROS)

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; 24 METHYLENECYCLOARTANYL FERULIC ACID; ALPHA TOCOPHEROL; ANTIOXIDANT; BETA SITOSTERYL FERULIC ACID; CYCLOARTENOL; CYCLOARTENYL FERULIC ACID; FERULIC ACID; HYDROGEN PEROXIDE; HYDROXYL RADICAL; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; PHYTOSTERYL FERULIC ACID; REACTIVE OXYGEN METABOLITE; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL STRAIN 3T3; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; ELECTRON SPIN RESONANCE; ENZYME ACTIVITY; IMMUNOHISTOCHEMISTRY; LIPID MEMBRANE; MOUSE; NONHUMAN; OXIDATIVE STRESS; STRUCTURE ACTIVITY RELATION;

EID: 74849084425     PISSN: 13478613     EISSN: 13478648     Source Type: Journal    
DOI: 10.1254/jphs.09146FP     Document Type: Article

References (43)

1. Castro L, Freeman BA. Reactive oxygen species in human health and disease. Nutrition. 2001;17:161,163-165.
2. Droge W. Free radicals in the physiological control of cell function. Physiol Rev. 2002;82:47-95.
3. Raha S, Robinson BH. Mitochondria, oxygen free radicals, disease and ageing. Trends Biochem Sci. 2000;25:502-508.
4. Dartsch PC. The potential of Asparagus-P to inactivate reactive oxygen radicals. Phytother Res. 2008;22:217-222.
5. Yokozawa T, Kim YA, Kim HY, Lee YA, Nonaka G. Protective effect of persimmon peel polyphenol against high glucose-induced oxidative stress in LLC-PK(1) cells. Food Chem Toxicol. 2007;45:1979-1987.
6. Pari L, Prasath A. Efficacy of caffeic acid in preventing nickel induced oxidative damage in liver of rats. Chem Biol Interact. 2008;173:77-83.
7. Raina K, Rajamanickam S, Deep G, Singh M, Agarwal R, Agarwal C. Chemopreventive effects of oral gallic acid feeding on tumor growth and progression in TRAMP mice. Mol Cancer Ther. 2008;7:1258-1267.
8. Maheshwari RK, Singh AK, Gaddipati J, Srimal RC. Multiple biological activities of curcumin: a short review. Life Sci. 2006;78:2081-2087.
9. Surh YJ. NF-κB and Nrf2 as potential chemopreventive targets of some anti-inflammatory and antioxidative phytonutrients with anti-inflammatory and antioxidative activities. Asia Pac J Clin Nutr. 2008;17 Suppl 1:269-272.
10. Chun KS, Cha HH, Shin JW, Na HK, Park KK, Chung WY, et al. Nitric oxide induces expression of cyclooxygenase-2 in mouse skin through activation of NF-κB. Carcinogenesis. 2004;25:445-454.
11. Chandel NS, Trzyna WC, McClintock DS, Schumacker PT. Role of oxidants in NF-κB activation and TNF-α gene transcription induced by hypoxia and endotoxin. J Immunol. 2000;165:1013-1021.
12. D'Angio CT, Finkelstein JN. Oxygen regulation of gene expression: a study in opposites. Mol Genet Metab. 2000;71:371-380.
13. Jariwalla RJ. Rice-bran products: phytonutrients with potential applications in preventive and clinical medicine. Drugs Exp Clin Res. 2001;27:17-26.
14. Xu Z, Godber JS. Purification and identification of components of γ-oryzanol in rice bran oil. J Agric Food Chem. 1999;47:2724-2728.
15. Kim SJ, Han D, Moon KD, Rhee JS. Measurement of superoxide dismutase-like activity of natural antioxidants. Biosci Biotechnol Biochem. 1995;59:822-826.
16. Juliano C, Cossu M, Alamanni MC, Piu L. Antioxidant activity of γ-oryzanol: mechanism of action and its effect on oxidative stability of pharmaceutical oils. Int J Pharm. 2005;299:146-154.
17. Islam MS, Murata T, Fujisawa M, Nagasaka R, Ushio H, Bari AM, et al. Anti-inflammatory effects of phytosteryl ferulates in colitis induced by dextran sulphate sodium in mice. Br J Pharmacol. 2008;154:812-824.
18. Nagasaka R, Chotimarkorn C, Shafiqul IM, Hori M, Ozaki H, Ushio H. Anti-inflammatory effects of hydroxycinnamic acid derivatives. Biochem Biophys Res Commun. 2007;358:615-619.
19. Chotimarkorn C, Ushio H. The effect of trans-ferulic acid and δγ-oryzanol on ethanol-induced liver injury in C57BL mouse. Phytomedicine. 2008;15:951-958.
20. Nystrom L, Makinen M, Lampi AM, Piironen V. Antioxidant activity of steryl ferulate extracts from rye and wheat bran. J Agric Food Chem. 2005;53:2503-2510.
21. Bligh EG, Dyer WJ. A rapid method of total lipid extraction and purification. Can J Biochem Physiol. 1959;37:911-917.
22. Huang WH, Lee AR, Yang CH. Antioxidative and anti-inflammatory activities of polyhydroxyflavonoids of Scutellaria baicalensis GEORGI. Biosci Biotechnol Biochem. 2006;70:2371-2380.
23. Janero DR. Malondialdehyde and thiobarbituric acid-reactivity as diagnostic indices of lipid peroxidation and peroxidative tissue injury. Free Radic Biol Med. 1990;9:515-540.
24. Teissier E, Nohara A, Chinetti G, Paumelle R, Cariou B, Fruchart JC, et al. Peroxisome proliferator-activated receptor alpha induces NADPH oxidase activity in macrophages, leading to the generation of LDL with PPAR-alpha activation properties. Circ Res. 2004;95:1174-1182.
25. Lebron F, Vassallo R, Puri V, Limper AH. Pneumocystis carinii cell wall β-glucans initiate macrophage inflammatory responses through NF-κB activation. J Biol Chem. 2003;278:25001-25008.
26. Matsuki N, Takanohashi A, Boffi FM, Inanami O, Kuwabara M, Ono K. Hydroxyl radical generation and lipid peroxidation in C2C12 myotube treated with iodoacetate and cyanide. Free Radic Res. 1999;31:1-8.
27. 1989. IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989. Eur J Biochem. 1989;186:429-458.
28. 2-induced cytotoxicity in macrophage RAW 264.7 cell lines. Biol Pharm Bull. 2006;29:1603-1607.
29. Soobrattee MA, Neergheen VS, Luximon-Ramma A, Aruoma OI, Bahorun T. Phenolics as potential antioxidant therapeutic agents: mechanism and actions. Mutat Res. 2005;579:200-213.
30. Rice-Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med. 1996;20:933-956.
31. Mastelic J, Jerkovic I, Blazevic I, Poljak-Blazi M, Borovic S, Ivancic-Bace I, et al. Comparative study on the antioxidant and biological activities of carvacrol, thymol, and eugenol derivatives. J Agric Food Chem. 2008;56:3989-3996.
32. Nam SH, Choi SP, Kang MY, Kozukue N, Friedman M. Antioxidative, antimutagenic, and anticarcinogenic activities of rice bran extracts in chemical and cell assays. J Agric Food Chem. 2005;53:816-822.
33. Prasad NR, Srinivasan M, Pugalendi KV, Menon VP. Protective effect of ferulic acid on gamma-radiation-induced micronuclei, dicentric aberration and lipid peroxidation in human lymphocytes. Mutat Res. 2006;603:129-134.
34. Sultana S, Alam A, Khan N, Sharma S. Inhibition of benzoyl peroxide and ultraviolet-B radiation induced oxidative stress and tumor promotion markers by cycloartenol in murine skin. Redox Rep. 2003;8:105-112.
35. Parasassi T, Giusti AM, Raimondi M, Ravagnan G, Sapora O, Gratton E. Cholesterol protects the phospholipid bilayer from oxidative damage. Free Radic Biol Med. 1995;19:511-516.
36. Abramov AY, Scorziello A, Duchen MR. Three distinct mechanisms generate oxygen free radicals in neurons and contribute to cell death during anoxia and reoxygenation. J Neurosci. 2007;27:1129-1138.
37. Lopez-Revuelta A, Sanchez-Gallego JI, Hernandez-Hernandez A, Sanchez-Yague J, Llanillo M. Increase in vulnerability to oxidative damage in cholesterol-modified erythrocytes exposed to t-BuOOH. Biochim Biophys Acta. 2005;1734:74-85.
38. Karin M, Greten FR. NF-kappaB: linking inflammation and immunity to cancer development and progression. Nat Rev Immunol. 2005;5:749-759.
39. DeLeo FR, Renee J, McCormick S, Nakamura M, Apicella M, Weiss JP, et al. Neutrophils exposed to bacterial lipopolysaccharide upregulate NADPH oxidase assembly. J Clin Invest. 1998;101:455-463.
40. Kim DK, Cho ES, Lee BR, Um HD. NF-κB mediates the adaptation of human U937 cells to hydrogen peroxide. Free Radic Biol Med. 2001;30:563-571.
41. Hughes G, Murphy MP, Ledgerwood EC. Mitochondrial reactive oxygen species regulate the temporal activation of nuclear factor κB to modulate tumour necrosis factor-induced apoptosis: evidence from mitochondria-targeted antioxidants. Biochem J. 2005;389:83-89.
42. 2 inhibition. J Pharm Pharmacol. 1997;49:329-331.
43. Akihisa T, Yasukawa K, Yamaura M, Ukiya M, Kimura Y, Shimizu N, et al. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflammatory effects. J Agric Food Chem. 2000;48:2313-2319.