Anti-inflammatory effect of certain dihydroxy flavones and the mechanisms involved

Anti-Inflammatory and Anti-Allergy Agents in Medicinal Chemistry

Volumn 11, Issue 3, 2012, Pages 253-261

  Vidyalakshmi, K ^a   Kamalakannan, P ^b   Viswanathan, S ^b   Ramaswamy, S ^c  

^a Madha Dental College   (India)

^b Department of Pharmacology   (India)

^c Affiliated to Bharath University   (India)

Author keywords

Anti inflammation; Cyclooxygenases; Cytokines; Dihydroxy flavones; Reactive oxygen species

Indexed keywords

1, 1 DIPHENYL 2 PICRYLHYDRAZYL; 3,3 DIHYDROXY FLAVONE; 3,7 DIHYDROXY FLAVONE; 5,6 DIHYDROXY FLAVONE; 6,3 DIHYDROXY FLAVONE; CELECOXIB; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DEXAMETHASONE; DIHYDROXY FLAVONE; FLAVONE DERIVATIVE; FREE RADICAL; IBUPROFEN; INTERLEUKIN 1BETA; NITRATE; REACTIVE OXYGEN METABOLITE; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; ENZYME IMMUNOASSAY; HUMAN; INFLAMMATION; MALE; NONHUMAN; PAW EDEMA; RAT; SPECTROPHOTOMETRY;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BIPHENYL COMPOUNDS; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; CYTOKINES; DOSE-RESPONSE RELATIONSHIP, DRUG; EDEMA; FLAVONES; FREE RADICAL SCAVENGERS; FREE RADICALS; HINDLIMB; INFLAMMATION; MALE; NITRATES; PICRATES; RATS; RATS, WISTAR;

EID: 84877776283     PISSN: 18715230     EISSN: 1875614X     Source Type: Journal    
DOI: 10.2174/1871523011202030253     Document Type: Article

References (34)

1. Alcaraz, M.J.; Ferrandiz, M.L. Modification of arachidonic acid metabolism by flavonoids.J Ethnopharmacol, 1987, 21, 209-229.
2. Lewis, D.A. Flavonoids. In: Lewis DA editor. Antiinflammatory drugs from plant and marine sources. Agents and Actions, Suppl.Vol 27, Basel: Berkhauser Verlag: 1989, 137-165.
3. Moroney, M.A.; Alcaraz, M.J.; Forder, R.A.; Carey, F.; Hoult, J.R. Selectivity of neutrophil 5-lipoxygenase and cyclo-oxygenase inhi-bition by an anti-inflammatory flavonoid glycoside and related aglycone flavonoids. J Pharm Pharmacol., 1988, 40(11), 787-792.
4. Parmar, N.S.; Ghosh, M.N. Antiinflammatory activity of gossypin, a bioflavonoid isolated from Hibiscus Vitifolius Linn. Ind. J. Phar-macol., 1978, 10, 277-293.
5. Li, B.Q.; Fu, T.; Gong, W.; Dunlop, N.; Kung, H.; Yan, Y.; Kang, K.; Ming, J.W. The flavonoid baicalin exhibits anti-inflammatory activity by binding to chemokines.Immunopharmacol., 2000, 49 (3), 295-306.
6. Jang, D.C.; Ceundet, M.; Hawthrone, M.E.; Kardona, L.B.S.; Ka-wanishi, K.; Fong, H.H.S.; Mehta, R.G.; Pezzuto, J.M.; Kinghorn, A.D. Prenylated flavonoids of leaves of Macaranga conifer with inhibitory activity against COX-2. Phytochem, 2002, 61, 867-872.
7. Morikawa, K.; Nonaka, M.; Narahara, M.; Torii, I.; Kawaguchi K.; Yoshikawa, T.; Kumazawa, Y.; Morikawa, S. Inhibitory effect of quercetin on carrageenan-induced inflammation in rats. Life Sci-ences, 2003, 74(6), 709-721.
8. Lee, H.G.; Kim, H.; Oh, W.K.; Yuk, A.; Choe, Y.K.; Ahn, J.S.; Kim, S.H.; Dinarello, C.A.; Kim, K.; Yoon, D.Y. Tetramethoxy hy-droxyl flavone P7F downregulates inflammatory mediators via the inhibition of Nuclear factor kappa B. Ann N Y Acad Sci, 2004, 1030, 555-568.
9. Sharma, V.; Mamata, M.; Sowmya, G.; Richa, T.; Anirban, B.; Pankaj, S.; Ellora, S. Modulation of interleukin-1β mediated in-flammatory responses in human astrocytes by flavonoids: Implica-tions in neuroprotection. Brain Res. Bull., 2007, 73, 55-63.
10. Harris, G.K.; Qian, T.; Heonard, S.S.; Sbarra, D.C.; Shix, M. Lute-olin and chrysin differentially inhibit cyclooxygenase-2 expression and scavenge reactive oxygen species but similarly inhibit prosta-glandin E2 formation in RAW264.7 cells. J. Nutr., 2006, 136, 1517-1527.
11. Vidyalakshmi, K.; Kamalakannan, P.; Viswanathan, S.; Ramas-wamy, S. Antinociceptive effect of certain dihydroxy flavones in mice. Pharmacol. Biochem. Behav., 2010, 96, 1-6.
12. Kim, H.P.; Kim, H.S.; Chang, H.W.; Kang, S.S. Anti-inflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol Sci. 2004, 96, 229-245.
13. Liu, J.; Li, X.; Yang, Y.; Li, J.; He, T.; He, Y. The inhibitory effect of quercetin on IL-6 production by LPS-stimulated neutrophils. Cell. Molecul. Immunol., 2005, 2(6), 455-460.
14. Winter, C.A.; Risley, E.A.; Nuss, G.W. Carrageenan-induced edema in the hind paw of the rats as an assay for anti-inflammatory drugs. Proc. Soc. Exp. Biol. Med., 1962, 111, 544-547.
15. Mani, V.; Kumar Kishore, G.; Milind, P. Antinociceptive and anti-inflammatory effects of Thespesia populnea bark extract. J. Ethno-pharmacol., 2007, 109(2), 264-270.
16. Shimda, K.; Fujikawa, K.; Yahara, K.; Nakamura, T. Antioxidative properties of Xanthan on autooxidation of soybean oil in cyclodex-trin emulsion. J. Agric. Food Chem., 1992, 40, 945-948.
17. Green, L.C.; Wagner, D.A.; Glogowski, J.; Skipper, P.L.; Wishnok, J.S.; Tanne baun, S.R. Analysis of nitrate, nitrite and (15N) nitrate in biological fluids. Analytical Biochem., 1982, 126, 131-138.
18. Kim, D.W.; Chi, Y.S.; Son, K.H; Chan, H.W.; Kim, J.S.; Kang, S.S.; Kim, H.P. Effect of sophoraflavonone G, a prenylated flavon-oid from Sophora flavescense on COX-2 and in vitro inflammatory response. Arch Pharm Res, 2005, 25, 329-335.
19. O'Leary, K.A.; Tereasa, S.D.P.; Needs, P.W.; Bao, Y.P.; O'Brien, N.M.; Williamson, G. Effect of flavonoids and vitamin E on cy-clooxygenase-2 (COX-2) transcription. Mutation Res., 2004, 551, 245-254.
20. Creange, A.; Bariovatz-Meimon, G.; Gherardi, R.K. Cytokines and peripheral nerve disorders. Eur Cytokine Netw, 1997, 8, 145-151.
21. Zhang, J.M.; An, J. Cytokines, Inflammation and pain. Int Anesthe-siol Clin, 2007, 45(2), 27-37.
22. Hougee, S.; Sanders, A.; Faber, J.; Graus, Y.M.F.; Van der berg, W.B.; Garssen, J.; Smit, H.F.; Hoijer, M.A. Decreased pro inflam-matory cytokine production by LPS-stimulated PBMC upon in vi-tro incubation with the flavonoids apigenin, luteolin or chrysin, due to selective elimination of monocytes/macrophages. Biochem. Pharmacol., 2005, 69, 241-248.
23. Nair, M.P.; Mahajan, S.; Reynolds, J.L.; Ravikumar, A.; Nair, H.; Schwartz, S.A.; Kandaswami, C. The flavonoid quercetin inhibits proinflammatory cytokine (Tumor necrosis factor alpha) gene ex-pression in normal peripheral blood mononuclear cells via modula-tion of the NF-k B system. Clin. Vac. Immunol., 2006, 13, 319-328.
24. Lin, N.; Sato, T.; Takayama, Y.; Mimaki, Y.; Sashida, Y.; Yano, M.; Ito, A. Novel anti-inflammatory actions of nobiletin, a citrus poly methoxy flavonoid, on human synovial fibroblasts and mouse macrophages. Pharmacology, 2003, 65(17), 2065-2071.
25. Fang, S.H.; Hoi, Y.C.; Chang, W.C.; Hsiu, S.L.; Chao, P.L.; Chang, B.L. Morin sulphates/glucuronides exert anti-inflammatory activity on activated macrophages and decrease the incidence of septic shock. Life Sci., 2003, 74, 743-756.
26. Hussain, S.A.; Jassim, N.A.; Numan, I.T.; Al-Khalifa, I.I.; Ab-dulla, T.A. Anti-inflammatory activity of silymarin in patients with Knee osteo arthritis; a comparitive study with piroxicam and meloxicam. Saudi Med J, 2009, 30, 99-105.
27. Vane, J.R.; Botting, B.M. Overview, the mechanism of action of anti-inflammatory drugs. In Vane JR.; Botting, B.M. eds. Clinical significance and potential of selective COX-2 inhibitors. London: William Harvey press, 1998, Pp, 1-18.
28. Burda, S.; Oleszek, W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem., 2001, 49, 2774-2779.
29. Rice-Evans, C.A.; Nicholas, J.M.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med., 1996, 20, 35-43.
30. Amic, D.; Davidovic, A.; Besto, D.; Trynastic, N. Structure-radi-cal scavenging activity relationships of flavonoids. Croat. Chem. Acta, 2003, 76, 55-61.
31. Farkas, O.; Jakus, J.; Heberger, K. Qualitative-structure antioxi-dant activity relationship of flavonoid compounds. Molecules. 2004, 9, 1079-1088.
32. Rang, H.P.; Dale, N.M.; Ritter, J.M.; Moore, P.K. Local hormones, inflammation and immune reactions. In: Rang and Dale's Pharmacol-ogy, 2003, V Edition, Churchill Livingstone, Elsevier, pp. 217-243.
33. Gulcin, I.; Beydemir, S.; Alici, H.A.; Elmastas, M.; Buyukokuroglu, M.E.In vitro antioxidant properties of morphine. Pharmacol. Res., 2004, 49, 59-66.
34. Gulcin, I.; Buyukokuroglu, M.E.; Okray, M.; Kufrevioglu, O.I. Antioxidant and analgesic activities of turpentine of Pinus nigra arn. Subsp. Pallsiana (lamb) holmboe. J. Ethnopharmacol, 2003, 86, 51-58.