Antiinflammatory and antinociceptive activities of gossypin and procumbentin - Cyclooxygenase-2 (COX-2) inhibition studies

Phytotherapy Research

Volumn 23, Issue 6, 2009, Pages 878-884

  Mada, Sripal Reddy ^a,c   Metukuri, Mallikarjuna Reddy ^b,d   Burugula, Laxminarayana ^a   Reddanna, Pallu ^b   Krishna, Devarakonda Rama ^a  

^a KAKATIYA UNIVERSITY   (India)

^b UNIVERSITY OF HYDERABAD   (India)

^c CENTER FOR DRUG EVALUATION AND RESEARCH   (United States)

^d UNIVERSITY OF PITTSBURGH SCHOOL OF MEDICINE   (United States)

Author keywords

Antiinflammatory; Antinociception; Gossypin; Procumbentin

Indexed keywords

ACETIC ACID; ARACHIDONATE 5 LIPOXYGENASE; CARRAGEENAN; CHRYSIN; CYCLOOXYGENASE 1; CYCLOOXYGENASE 2; DIAMINE; FLAVANOID; GOSSYPINE; METHYLHESPIRIDIN; NN N'N' TETRAMETHYL 4 PHENYLENE DIAMINE; PROCUMBENTIN; UNCLASSIFIED DRUG; ANALGESIC AGENT; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 2 INHIBITOR; FLAVONOID; LIPOXYGENASE INHIBITOR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; EDEMA; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; MALE; NONHUMAN; RAT; WRITHING TEST; ANIMAL; CHEMICAL STRUCTURE; MOUSE; PAIN ASSESSMENT; WISTAR RAT;

ANIMALIA; MUS; RATTUS;

ANALGESICS; ANIMALS; ANTI-INFLAMMATORY AGENTS; CYCLOOXYGENASE 2 INHIBITORS; FLAVONOIDS; INHIBITORY CONCENTRATION 50; LIPOXYGENASE INHIBITORS; MALE; MICE; MOLECULAR STRUCTURE; PAIN MEASUREMENT; RATS; RATS, WISTAR;

EID: 67149121180     PISSN: 0951418X     EISSN: 10991573     Source Type: Journal    
DOI: 10.1002/ptr.2727     Document Type: Article

References (43)

1. Ali M, Ravinder E, Ramachandran R. 2001. A new flavonoid from the aerial parts of Tridax procumbens. Fitoterapia 72: 313-315. (Pubitemid 32273481)
2. Anon MT, Ubeda A, Alcaraz MJ. 1992. Protective effects of phenolic compounds on CCl4-induced toxicity in isolated rat hepatocytes. Z Naturforsch [C] 47: 275-279.
3. Babu BH. 2003. Free radical scavenging, antitumor and anticarcinogenic activity of gossypin. J Exp Clin Cancer Res 22: 581-589. (Pubitemid 38222044)
4. Basu S. 1999. Oxidative injury induced cyclooxygenase activation in experimental hepatotoxicity. Biochem Biophys Res Commun 254: 761-767. (Pubitemid 29290542)
5. Berger I, Barrientos AC, Caleras A et al. 1998. Plants used in Guatemala for the treatment of protozoal infections: II. Activity of extracts and fractions of five Guatemalan plants against Trypanosoma cruzi. J Ethnopharmacol 62: 107-115. (Pubitemid 28400982)
6. Cai Z, Li X, Katsumura Y. 1999. Interaction of hydrated electron with dietary flavonoids and phenolic acids: rate constants and transient spectra studied by pulse radiolysis. Free Radic Biol Med 27: 822-829. (Pubitemid 29454585)
7. Copeland RA, Williams JM, Giannaras J et al. 1994. Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase. Proc Natl Acad Sci USA 91: 11202-11206. (Pubitemid 24349654)
8. Cummings KB, Robertson RP. 1977. Prostaglandin: increased production by renal cell carcinoma. J Urol 118: 720-723. (Pubitemid 8242656)
9. Emim JADS, Oliveira AB, Lapa AJ. 1994. Pharmacological evaluation of the anti-inflammatory activity of a citrus bioflavonoid, hesperidin, and the isoflavonoids, duartin and claussequinone, in rats and mice. J Pharm Pharmacol 46: 118-122. (Pubitemid 24070840)
10. Ferrandiz ML, Alcaraz MJ. 1991. Anti-inflammatory activity and inhibition of arachidonic acid metabolism by flavonoids. Agents Actions 32: 283-288.
11. Flugge LA, Miller-Deist LA, Petillo PA. 1999. Towards a molecular understanding of arthritis. Chem Biol 6: 157-166. (Pubitemid 29363164)
12. Gautam A, Vijayaraghavan R. 2007. Prophylactic effect of gossypin against percutaneously administered sulfur mustard. Biomed Environ Sci 20: 250-259. (Pubitemid 47253851)
13. Harris GK, Qian Y, Leonard SS, Sbarra DC, Shi X. 2006. Luteolin and chrysin differentially inhibit cyclooxygenase-2 expression and scavenge reactive oxygen species but similarly inhibit prostaglandin-E2 formation in RAW 264.7 cells. J Nutr 136: 1517-1521. (Pubitemid 43765355)
14. Jean T, Bodinier MC. 1994. Mediators involved in inflammation: effects of Daflon 500 mg on their release. Angiology 45: 554-559. (Pubitemid 24179193)
15. Kawaguchi K, Mizuno T, Aida K, Uchino K. 1997. Hesperidin as an inhibitor of lipases from porcine pancreas and Pseudomonas. Biosci Biotech Biochem 61: 102-104. (Pubitemid 27164853)
16. Kawamori T, Rao CV, Seibert K, Reddy BS. 1998. Chemopreventive activity of celecoxib, a specific cyclooxygenase-2 inhibitor, against colon carcinogenesis. Cancer Res 58: 409-412. (Pubitemid 28087398)
17. Kren V, Walterová D. 2005. Silybin and silymarin - new effects and applications. Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub 149: 29-41.
18. Kunnumakkara AB, Nair AS, Ahn KS et al. 2007. Gossypin, a pentahydroxy glucosyl flavone, inhibits the transforming growth factor beta-activated kinase-1-mediated NF-kappaB activation pathway, leading to potentiation of apoptosis, suppression of invasion, and abrogation of osteoclastogenesis. Blood 109: 5112-5121. (Pubitemid 46890525)
19. Laekeman G, De Coster S, De Meyer K. 2003. St Mary's thistle: an overview. J Pharm Belg 58: 28-31.
20. Lin CM, Chang H, Li SY, Wu IH, Chiu JH. 2006. Chrysin inhibits lipopolysaccharide-induced angiogenesis via down-regulation of VEGF/VEGFR-2(KDR) and IL-6/IL-6R pathways. Planta Med 72: 708-714. (Pubitemid 44073454)
21. Luong C, Muller A, Barnett J, Chow J, Ramesha C, Brower MF. 1996. Flexibility of the NSAID binding site in the structure of human cyclooxygenase-2. Nat Struct Biol 3: 927-933. (Pubitemid 26398325)
22. Marnett LJ, Kalgutkar AS. 1999. Cyclooxygenase 2 inhibitors: discovery, selectivity and the future. Trend Pharmacol Sci 20: 465-469. (Pubitemid 29528219)
23. Miesel R, Zuber M. 1993. Elevated levels of xanthine oxidase in serum of patients with inflammatory and autoimmune rheumatic diseases. Inflammation 17: 551-561. (Pubitemid 23252893)
24. Ramaswamy S, Viswanathan S. 1997. Influence of gossypin on the development of acute tolerance to morphine induced antinociception. Indian J Exp Biol 35: 413-414. (Pubitemid 28103836)
25. Reddanna P, Whelan J, Maddipathi KR. 1990. Purification of arachidonate 5-lipoxygenase from potato tubers. Methods Enzymol 187: 268-277. (Pubitemid 20309290)
26. Reddy CM, Bhat VB, Kiranmai G. 2000. Selective inhibition of cyclooxygenase-2 by C-phycocyanin, a biliprotein from Spirulina platensis. Biochem Biophys Res Commun 277: 599-603. (Pubitemid 30819726)
27. Saller R, Melzer J, Reichling J, Brignoli R, Meier R. 2007. An updated systematic review of the pharmacology of silymarin. Forsch Komplementarmed 14: 70-80. (Pubitemid 46652418)
28. Schubert SY, Lansky EP, Neeman I. 1999. Antioxidant and eicosanoid enzyme inhibition properties of pomegranate seed oil and fermented juice flavonoids. J Ethnopharmacol 66: 11-17. (Pubitemid 29305408)
29. Smith WL, Garavito RM, DeWitt DL. 1996. Prostaglandin endoperoxide H synthases (cyclooxygenases)-1 and -2. J Biol Chem 271: 33157-33160. (Pubitemid 27010118)
30. Solomon DH, Karlson EW, Rimm EB. 2003. Cardiovascular morbidity and mortality in women diagnosed with rheumatoid arthritis. Circulation 107: 1303-1307. (Pubitemid 36314415)
31. Subbaramaiah K, Chung WJ, Michaluart P et al. 1998. Resveratrol inhibits cyclooxygenase-2 transcription and activity in phorbol ester-treated human mammary epithelial cells. J Biol Chem 273: 21875-21882. (Pubitemid 28405365)
32. Subbaramaiah K, Zakim D, Weksler BB, Dannenberg AJ. 1997. Inhibition of cyclooxygenase: a novel approach to cancer prevention. Proc Soc Exp Biol Med 216: 201-210. (Pubitemid 27449567)
33. Udupa SL, Udupa AC, Kulkurni DR. 1991. Influence of Tridax procumbens on lysyl oxidase activity and wound healing. Planta Med 57: 325-327.
34. Valenzuela A, Garrido A. 1994. Biochemical bases of the pharmacological action of the flavonoid silymarin and of its structural isomer silibinin. Biol Res 27: 105-112. (Pubitemid 24257808)
35. Vane JR, Bakhle YS, Botting RM. 1998. Cyclooxygenases 1 and 2. Annu Rev Pharmacol Toxicol 38: 97-120.
36. Vijayan P, Raghu C, Ashok G, Dhanaraj SA, Suresh B. 2004. Antiviral activity of medicinal plants of Nilgiris. Indian J Med Res 120: 24-29. (Pubitemid 39177430)
37. Vijayaraghavan R, Sugendran K, Pant SC, Husain K, Malhotra RC. 1991. Dermal intoxication of mice with bis(2-chloroethyl)sulphide and the protective effect of flavonoids. Toxicology 69: 35-42.
38. Viswanathan S, Thirugnanasambantham P, Ramaswamy S, Bapna JS. 1993. A study on the role of cholinergic and gamma amino butyric acid systems in the anti-nociceptive effect of gossypin. Clin Exp Pharmacol Physiol 20: 193-196. (Pubitemid 23090024)
39. Wang HK, Xia Y, Yang ZY, Natschke SL, Lee KH. 1998. Recent advances in the discovery and development of flavonoids and their analogues as antitumor and anti-HIV agents. Adv Exp Med Biol 439: 191-225. (Pubitemid 28429018)
40. Woo KJ, Jeong YJ, Inoue H, Park JW, Kwon TK. 2005. Chrysin suppresses lipopolysaccharide-induced cyclooxygenase-2 expression through the inhibition of nuclear factor for IL-6 (NF-IL6) DNA-binding activity. FEBS Lett 579: 705-711.
41. Woodman OL, Chan EC. 2004. Vascular and anti-oxidant actions of flavonols and flavones. Clin Exp Pharmacol Physiol 31: 786-790. (Pubitemid 39556854)
42. Yoon I, Lee KH, Cho J. 2004. Gossypin protects primary cultured rat cortical cells from oxidative stress- and betaamyloid- induced toxicity. Arch Pharm Res 27: 454-459. (Pubitemid 43073744)
43. Zschocke S, Van Staned J. 2000. Cryptocarya species - substitute plants for Ocotea bullata? A pharmacological investigation in terms of cyclooxygenase-1 and -2 inhibition. J Ethnopharmacol 71: 473-478. (Pubitemid 30642871)