ANTI-RADICAL ACTIVITIES OF XANTHONES AND FLAVONOIDS FROM GARCINIA SCHOMBURGKIANA

  • Imron Meechai School of Science, Walailak University, Nakhon Si Thammarat, 80161, Thailand
  • Worrapong Phupong The Research Unit of Natural Product Utilization, Walailak University, Nakhon Si Thammarat, 80161, Thailand
  • Warangkana Chunglok School of Allied Health Sciences and Public Health, Walailak University, Nakhon Si Thammarat, 80161, Thailand
  • Puttinan Meepowpan Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand

Abstract

Objective: The present study aimed to isolate and identify the phytochemical constituents of Garcinia schomburgkiana branches and evaluate the antioxidant activity of the compounds.

Methods: The chromatographic and spectroscopic (UV, IR, NMR and MS) techniques were used for the isolation and elucidation of the compounds, respectively. The antioxidant activity of the isolated compounds was examined through DPPH, ABTS, nitric oxide and hydroxyl radical scavenging assay.

Results: The (-)-5,7,3′,5′-tetrahydroxyflavanone (1), which was firstly found in the Garcinia species, together with kaempferol (2), (-)-dihydrokaempferol (3), euxanthone (4), gentisein (5) and norathyriol (6) were isolated from G. schomburgkiana. Among the isolated compounds, compound 1 and 6 exhibited the highest potential for anti-radical activities.

Conclusion: Compound 1 could be used as the chemotaxonomic marker of G. schomburgkiana. The branches of G. schomburgkiana could be the alternative source of the antioxidants. The possible inhibitory mechanisms were proposed through the action of electron transfer, chelation, and nitrosylation.

 

Keywords: Xanthones, Flavonoids, Anti-radical activities, Garcinia schomburgkiana

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References

1. Ritthiwigrom T, Laphookhieo S, Pyne SG. Chemical constituents and biological activities of Garcinia cowa Roxb. Maejo Int J Sci Technol 2013;7:212-31.
2. Lim TK. Edible, medicinal and non-medicinal plants. Vol. 2. New York (USA): Springer Dordrecht Heidelberg London; 2012.
3. Fun HK, Koysomboon S, Chantrapromma K, Chantrapromma S. A cocrystal of clusiacitran A, clusiacitran B, fluorinated clusiacitran A and fluorinated clusiacitran B (0.45:0.45:0.05:0.05). Acta Crystallogr 2006;E62:3228-30.
4. Häfner A, Frahm AW. Bioflavonoids from the heartwood of Garcinia schomburgkiana and their structural elucidation as atropisomers. Planta Med 1993;59:A604.
5. Mungmee C, Sitthigool S, Buakeaw A, Suttisri R. A new biphenyl and other constituents from the wood of Garcinia schomburgkiana. Nat Prod Res 2013;27:1949-55.
6. Nessa F, Ismail Z, Mohamed N, Haris MRHM. The free radical-scavenging activity of organic extract and of pure flavonoids of Blumea balsamifera DC leaves. Food Chem 2004;88:243-52.
7. Zongo C, Savadogo A, Ouattara L, Bassole IHN, Ouattara CAT, Ouattara AS, et al. Polyphenols content, antioxidant and antimicrobial activities of Ampelocissus grantii (Baker) Planch. (Vitaceae): a medicinal plant from Burkina Faso. Int J Pharmacol 2010;6:880-7.
8. Gogoi N, Gogoi A, Neog B. Free radical scavenging activities of Garcinia xanthochymus Hook. F. and Garcinia lanceaefolia Roxb. Using various in vitro assay models. Asian J Pharm Clin Res 2015;8:138-41.
9. Re R, Pellegrini N, Proteggente A, Pannala A, Yang M, Rice-Evans C. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biol Med 1999;26:1231–7.
10. Harput UŞ, Genç Y, Khan N, Saracoglu İ. Radical scavenging effects of different Veronica species. Rec Nat Prod 2011;5:100-7.
11. Ho SC, Tang YL, Lin SM, Liew YF. Evaluation of peroxynitrite-scavenging capacities of several commonly used fresh spices. Food Chem 2010;119:1102-7.
12. Krishnaveni M. In vitro antioxidant activity of Terminalia catappa nuts. Asian J Pharm Clin Res 2014;7:33-5.
13. Omwamba M, Li F, Sun G, Hu Q. Antioxidant effect of roasted barley (Hordeum vulgare L.) grain extract towards oxidative stress in vitro and in vivo. FNS 2013;4:139-46.
14. Lee IC, Bae JS, Kim T, Kwon OJ, Kim TH. Polyphenolic constituents from the aerial parts of Thymus quinquecostatus var. japonica collected on ulleung island. J Korean Soc Appl Biol Chem 2011;54:811–6.
15. Yamauchi K, Mitsunaga T, Batubara I. Isolation, identification, and tyrosinase inhibitory activities of the extractives from Allamanda cathartica. Nat Resour 2011;2:167-72.
16. Jeon YE, Yin XF, Choi DB, Lim SS, Kang IJ, Shim JH. Inhibitory activity of aromadendrin from prickly pear (Opumtia ficus-indica) root on aldose reductase and the formation of advanced glycation end products. Food Sci Biotechnol 2011;20:1283-8.
17. Mak NK, Li WK, Zhang M, Wong RNS, Tai LS, Yung KKL, et al. Effects of euxanthone on neuronal differentiation. Life Sci 2000;66:347-54.
18. Mondal M, Puranik VG, Argade NP. Facile synthesis of 1,3,7-trihydroxyxanthone and Its regioselective coupling reactions with prenal: simple and efficient access to osajaxanthone and nigrolineaxanthone F. J Org Chem 2006;71:4992-5.
19. Noro T, Ueno A, Mizutani M, Hashimoto T, Miyase T, Kuroyanagi M, et al. Inhibitors of xanthine oxidase from Athyrium mesosorum. Chem Pharm Bull 1984;32:4455-9.
20. Malhotra S, Shakya G, Kumar A, Vanhoecke BW, Cholli AL, Raj HG, et al. Antioxidant, anti-inflammatory and antiinvasive activities of bio polyphenolics. ARKIVOC 2008;6:119-39.
21. Tirzitis G, Bartosz G. Determination of antiradical and antioxidant activity: basic principles and new insights. Acta Biochim Pol 2010;57:139-42.
22. Flora SJS. Structural, chemical and biological aspects of antioxidants for strategies against metal and metalloid exposure. Oxid Med Cell Longev 2009;2:191-206.
23. Kaiserová H, Šimůnek T, van der Vijgh WJF, Bast A, Kvasničková E. Flavonoids as protectors against doxorubicin cardiotoxicity: role of iron chelation, antioxidant activity and inhibition of carbonyl reductase. Biochim Biophys Acta 2007;1772:1065-74.
24. Gunther MR, Hsi LC, Curtis JF, Gierse JK, Marnett LJ, Eling TE, et al. Nitric oxide trapping of the tyrosyl radical of prostaglandin H synthase-2 leads to tyrosine imioxyl radical and nitrotyrosine formation. J Biol Chem 1997;272:17086-90.
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How to Cite
Meechai, I., W. Phupong, W. Chunglok, and P. Meepowpan. “ANTI-RADICAL ACTIVITIES OF XANTHONES AND FLAVONOIDS FROM GARCINIA SCHOMBURGKIANA”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 8, no. 9, Sept. 2016, pp. 235-8, doi:10.22159/ijpps.2016v8i9.13213.
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