RECENT THERAPEUTIC PROGRESS OF CHALCONE SCAFFOLD BEARING COMPOUNDS AS PROSPECTIVE ANTI-GOUT CANDIDATES

  • Debarshi Kar Mahapatra Department of Pharmaceutical Chemistry, Dadasaheb Balpande College of Pharmacy, Nagpur, Maharashtra, 440037, India
  • Vivek Asati Department of Pharmaceutical Chemistry, NRI Institute of Pharmacy, Bhopal, Madhya Pradesh, 462021, India
  • Sanjay Kumar Bharti Institute of Pharmaceutical Sciences, Guru Ghasidas Vishwavidyalaya (A Central University), Bilaspur, Chhattisgarh, 495009, India

Abstract

Gout is a common form of arthritis characterized by severe and sudden pain for a long duration, swelling, tenderness, lingering discomfort, and acute redness in the joint situated at the big toe due to the accumulation of monosodium urate (MSU) crystals. Though, at present these drugs have limited pharmacodynamics benefits with the emergence of adverse effects. Therefore, the modern trend has perceived a shift towards the regular use of natural products and tailored-approach, which have revolutionized the prescription pattern from traditional combinations to unexplored classes of drugs. Natural product classes such as chalcones have received adequate attention for treating these severe ailments with a better margin of safety. Chalcone or 1,3-diphenyl-2-propene-1-one or benzylideneacetophenone are the natural scaffold comprising of two aromatic rings connected together by a three-carbon α, β unsaturated carbonyl link. The chalcone scaffold bearing synthetic (polyhydroxylated chalcones, 3,5,2,4-tetrahydroxychalcone, trans-chalcone) and natural (sappanchalcone, okanin, hesperidin methylchalcone, quercetin chalcone, 4-hydroxyderricin, isobavachalcone, xanthoangelol F, xanthoangelol, and xanthoangeleol B) compounds have been found to exhibit tremendous anti-gout activity by completely suppressing the active disease proliferating enzyme, xanthine oxidase (XO) as well as by suppressing the activation of nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κβ), along with preventing the formation and influx of pro-inflammatory factors. The overview glance of this scientific review will provide information to the scientists working in the pharmaceutical as well as allied science fields in fabricating, screening, and exploring the abundant hidden chemical classes based on the provided structural, chemical, and miscellaneous aspects.

Keywords: Chalcone, Gout, Inflammation, Xanthine oxidase, Inhibition, NF-κβ

Author Biography

Sanjay Kumar Bharti, Institute of Pharmaceutical Sciences, Guru Ghasidas Vishwavidyalaya (A Central University), Bilaspur, Chhattisgarh, 495009, India

Assistant Professor,

Institute of Pharmaceutical Sciences,

Guru Ghasidas Vishwavidyalaya (A Central University),

Bilaspur, Chhattisgarh, 495009, India

References

1. Reinders MK, Tim L. New advances in the treatment of gout: the review of pegloticase. Ther Clin Risk Manag 2010;6:543-50.
2. Robinson PC, Taylor WJ, Merriman TR. Systematic review of the prevalence of gout and hyperuricaemia in Australia. Int Med J 2012;42:997-1007.
3. Terkeltaub RA. Gout. New Eng J Med 2003;349:1647-55.
4. Harrold L. New developments in gout. Curr Opin Rheumatol 2013;25:304-9.
5. Campano GD, Holmes EW. Hyperuricemia and gout. Med Clin North Am 1986;70:419-36.
6. Kim KY, Schumacher HR, Hunsche E, Wertheimer AI, Kong SX. A literature review of the epidemiology and treatment of acute gout. Clin Ther 2003;25:1593-617.
7. Singh JA, Reddy SG, Kundukulam J. Risk factors for gout and prevention: a systematic review of the literature. Curr Opin Rheumatol 2011;23:192-202.
8. Emmerson BT. The management of gout. New Eng J Med 1996;334:445-51.
9. Schlesinger N. Management of acute and chronic gouty arthritis. Drugs 2004;64:2399-416.
10. Terkeltaub R. Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol 2010;6:30-8.
11. Sharma R, Kumar R, Kodwani R, Kapoor S, Khare A, Bansal R, et al. A review on mechanisms of antitumor activity of chalcones. Anti Cancer Agent Med Chem 2016;16:200-11.
12. Mahapatra DK, Bharti SK, Asati V. Anti-cancer chalcones: structural and molecular target perspectives. Eur J Med Chem 2015;98:69-114.
13. Mahapatra DK, Asati V, Bharti SK. Chalcones and their therapeutic targets for the management of diabetes: structural and pharmacological perspectives. Eur J Med Chem 2015;92:839-65.
14. Mahapatra DK, Bharti SK, Asati V. Chalcone scaffolds as anti-infective agents: structural and molecular target perspectives. Eur J Med Chem 2015;101:496-524.
15. Mahapatra DK, Bharti SK. Therapeutic potential of chalcones as cardiovascular agents. Life Sci 2016;148:154-72.
16. Mahapatra DK, Bharti SK, Asati V. Chalcone derivatives: anti-inflammatory potential and molecular targets perspectives. Curr Top Med Chem 2017;17:3146-69.
17. Mahapatra DK, Bharti SK, Asati V. Recent perspectives of chalcone based molecules as protein tyrosine phosphatase 1B (PTP-1B) inhibitors. In: Mahapatra DK, Bharti SK. editors. Medicinal chemistry with pharmaceutical product development. 1st ed. New Jersey: Apple Academic Press; 2019. p. 235-51.
18. Gomes M, Muratov E, Pereira M, Peixoto J, Rosseto L, Cravo P, et al. Chalcone derivatives: promising starting points for drug design. Molecules 2017;22:1210.
19. Zhuang C, Zhang W, Sheng C, Zhang W, Xing C, Miao Z. Chalcone: a privileged structure in medicinal chemistry. Chem Rev 2017;117:7762-810.
20. Nowakowska Z. A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 2007;42:125-37.
21. K Sahu N, S Balbhadra S, Choudhary J, V Kohli D. Exploring the pharmacological significance of chalcone scaffold: a review. Curr Med Chem 2012;19:209-25.
22. Singh P, Anand A, Kumar V. Recent developments in biological activities of chalcones: a mini review. Eur J Med Chem 2014;85:758-77.
23. Matos MJ, Vazquez Rodriguez S, Uriarte E, Santana L. Potential pharmacological uses of chalcones: a patent review (from June 2011–2014). Exp Opin Ther Patent 2015;25:351-66.
24. Nasir Abbas Bukhari S, Jasamai M, Jantan I, Ahmad W. Review of methods and various catalysts used for chalcone synthesis. Mini Rev Org Chem 2013;10:73-83.
25. Hofmann E, Webster J, Do T, Kline R, Snider L, Hauser Q, et al. Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers. Bioorg Med Chem 2016;24:578-87.
26. Beiler JM, Martin GJ. The inhibition of xanthine oxidase by flavonoids and related compounds. J Biol Chem 1951;192:831-4.
27. Niu Y, Zhu H, Liu J, Fan H, Sun L, Lu W, et al. 3, 5, 2?, 4?-tetrahydroxychalcone, a new non-purine xanthine oxidase inhibitor. Chem Biol Interact 2011;189:161-6.
28. Husain K, Wai LK, Jamaluddin F, Jamal JA, Ummah Abu N. Xanthine oxidase inhibitory activity of selected chalcone derivatives. Open Conf Proc J 2013;4:286.
29. Xie Z, Luo X, Zou Z, Zhang X, Huang F, Li R, et al. Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia. Bioorg Med Chem Lett 2017;27:3602-6.
30. Bui TH, Nguyen NT, Dang PH, Nguyen HX, Nguyen MT. Design and synthesis of chalcone derivatives as potential non-purine xanthine oxidase inhibitors. Springer Plus 2016;5:1789.
31. Nguyen MT, Awale S, Tezuka Y, Le Tran Q, Kadota S. Xanthine oxidase inhibitors from the heartwood of vietnamese caesalpinia sappan. Chem Pharm Bull 2005;53:984-8.
32. Ruiz Miyazawa KW, Pinho Ribeiro FA, Borghi SM, Staurengo Ferrari L, Fattori V, Amaral F, et al. Hesperidin methyl chalcone suppresses experimental gout arthritis in mice by inhibiting NF-kB activation. J Agric Food Chem 2018;66:6269-80.
33. Staurengo Ferrari L, Ruiz Miyazawa KW, Pinho Ribeiro FA, Fattori V, Zaninelli TH, Badaro Garcia S, et al. Trans-chalcone attenuates pain and inflammation in experimental acute gout arthritis in mice. Front Pharmacol 2018;9:1123.
34. Kim DW, Curtis Long MJ, Yuk HJ, Wang Y, Song YH, Jeong SH, et al. Quantitative analysis of phenolic metabolites from different parts of Angelica keiskei by HPLC–ESI MS/MS and their xanthine oxidase inhibition. Food Chem 2014;153:20-7.
35. Liu Y, Hou Y, Si Y, Wang W, Zhang S, Sun S, et al. Isolation, characterization, and xanthine oxidase inhibitory activities of flavonoids from the leaves of Perilla frutescens. Natural Prod Res 2018;26:1-7.
36. Birdsall TC, Czap AF. Inventor; Thorne Research Inc. Ltd., assignee. Quercetin chalcone and methods related thereto. United States Patent US5977184A; 1999.
37. Martin GJ, Morton BJ. Inventor; National Drug Co. Ltd., assignee. Therapeutic substituted chalcones. United States Patent US2769817A; 1951.
38. Edwards ML, Sunkara SP, Stemerick DM. Inventor; aventis inc. Ltd, assignee. Methods of treating gout with chalcone derivatives. United States Patent US4863968A; 1987.
39. Sunkara SP, Edwards ML, Stemerick DM. Inventor; aventis Inc. Ltd, assignee. Controlling the growth of certain tumor tissue with chalcone derivatives. United States Patent US4904697A; 1987.
40. Chang ST, Tung YT. Inventor; National Taiwan University. Acacia extracts and their compounds on inhibition of xanthine oxidase. United States Patent US20100310688A1; 2009.
41. Chang ST, Tung YT. Inventor; National Taiwan University. Use of Acacia extracts and their compounds on inhibition of xanthine oxidase. United States Patent US8414936B2; 2009.
Statistics
252 Views | 207 Downloads
Citatons
How to Cite
Kar Mahapatra, D., Asati, V., & Bharti, S. K. (2019). RECENT THERAPEUTIC PROGRESS OF CHALCONE SCAFFOLD BEARING COMPOUNDS AS PROSPECTIVE ANTI-GOUT CANDIDATES. Journal of Critical Reviews, 6(1). https://doi.org/10.22159/jcr.2019v6i1.31760
Section
Pharmaceutical Sciences