NEW FLAVONOIDS FROM THE AERIAL PARTS OF POLYGONUM EQUISETIFORME SM (POLYGONACEAE)
DOI:
https://doi.org/10.22159/ijpps.2017v9i2.15593Keywords:
Polygonum equisetiforme, Aerial parts, New flavonoid, Antioxidant activityAbstract
Objective: The current study was to deal the isolation and identification of secondary metabolites from Polygonum equisetiforme and evaluation of antioxidant activity of its extract.
Methods: The methanol-water extract (7:3) of the air-dried aerial parts of Polygonum equisetiforme was fractionated and separated to obtain the isolated compounds by different chromatographic techniques. Structures of these compounds were elucidated by UV and 1Dâ„2D Hâ„ C NMR spectroscopy and compared with the literature data. The crude extract was evaluated for in vitro antioxidant activity using the 2,2 diphenyl dipicryl hydrazine (DPPH) method.
Results: Ten secondary metabolites were isolated from Polygonum equisetiforme in this study. Of which three new flavonoids named as 3,5,7,2',5' pentahydroxyflavone 3-O-b-D-glucopyranoside (1), 3,5,7,2',5' pentahydroxyflavone 3-O-b-D-glucopyranoside 8 C-sulphated (2) and quercetin 3-O-β-D-glucucorinde 6''-methyl ester 8-sulphated (3) as well as quercetin 3-O-β-D-glucucorinde methyl ester (4), quercetin 3-O-β-D-glucopyranoside (5), quercetin 7-O-β-D-glucopyranoside (6), quercetin(7), myricetin (8), P-methoxy gallic acid methyl ester (9) and gallic acid (10). The antioxidant potential of P. equisetiforme extract was evaluated by investigating it's total phenolic and flavonoid content and DPPH radical scavenging activity whereby the extract showed significant antioxidant activity (IC50 = 37.45 μg/ml). The total phenolic and flavonoid content was found to be 130.79±5.502 and 45.8±1.63 μg/ml, respectively.
Conclusion: Polygonum equisetiforme is a promising medicinal plant, and our study tends to support the therapeutic value of this plant as an antioxidant drug.
Downloads
References
Mabberley DJ. Mabberley's plant-book: a portable dictionary of plants, their classification and uses, third edition. Cambridge University Press: UK; 2008.
Boulos L. In: Flora of Egypt. Vol. 1. Al Hadara Puplishing, Cairo, Egypt; 1999.
Datta BK, Datta SK, Rashid MA, Sarker SD. Flavonoids from Polygonum stagninum (Polygonaceae). Biochem Syst Ecol 2002;30:693-6.
Sun X, Sneden AT. Neoflavonoids from Polygonum perfoliatum. Plant Med 1999;65:671-3.
Hyoung JK, Eun RW, Hokoon P. A Novel lignan and flavonoids from Polygonum aviculare. J Nat Prod 1994;57:581–6.
Lopez SN, Sierra MG, Gattuso SJ, Furlan RL, Zacchino SA. An unusual homoisoflavanone and a structurally related dihydrochalcone from Polygonum ferrugineum (Polygonaceae). Phytochemistry 2006;67:2152-8.
Han L, Wu B, Pan G, Wang Y, Song X, Gao X. UPLC-PDA analysis for simultaneous quantification of four active compounds in crude and processed rhizome of Polygonum multiflorum Thunb. Chromatographia 2009;70:657-9.
Abd El-kader AM, Ahmed AS, Nafady AM, Ibraheim ZZ. Xanthone and lignan glycosides from the aerial parts of Polygonum bellardii all growing in Egypt. Pharmacogn Mag 2013;9:135-43.
Cui JJ, Yuan JF, Zhang ZQ. Anti-oxidation activity of the crude polysaccharides isolated from Polygonum cillinerve (Nakai) Ohwi in immunosuppressed mice. J Ethnopharmacol 2010;132:512-7.
Brown LL, Larson SR, Sneden AT. Vanicosides C-F, new phenylpropanoid glycosides from Polygonum pensylvanicum. J Nat Prod 1998;61:762-6.
Datta BK, Datta SK, Rashid MA, Nash RJ, Sarker SD. A sesquiterpene acid and flavonoids from Polygonum viscosum. Phytochemistry 2000;54:201-5.
Datta BK, Rashid MA, Datta SK, Sarker SD. Viscozulenic acid: a novel sesquiterpene acid from Polygonum viscosum. Pharm Biol 2001;39:198-201.
Haraguchi H, Matsuda R, Hashimoto K. High-performance liquid chromatographic determination of sesquiterpene dialdehydes and antifungal activity from Polygonum hydropiper. J Agric Food Chem 1993;41:5–7.
Kim HK, Choi YH, Choi JS, Choi SU, Kim YS, Lee KR, et al. A new stilbene glucoside gallate from the roots of Polygonum multiflorum. Arch Pharm Res 200;31:1225-9.
Chen LL, Huang XJ, Li MM, Ou GM, Zhao BX, Chen MF, et al. Polygonflavanol A, a novel flavonostilbene glycoside from the roots of Polygonum multiflorum. Phytochem Lett 2012;5:756–60.
Abdul Mazid M, Datta BK, Nahar L, Khairul Bashar SAM, Bachar SC, Sarker SD. Antinociceptive, anti-inflammatory and diuretic properties of Polygonum barbatum (L.) Hara var. barbata. Braz J Pharmacogn 2009;19:749-54.
Cakilcioglu U, Turkoglu I. An ethnobotanical survey of medicinal plants in Sivrice (Elazığ-Turkey). J Ethnopharmacol 2010;132:165–75.
Zhang YZ, Shen JF, Xu JY, Xiao JH, Wang JL. Inhibitory effects of 2,3,5,4′-tetrahydroxystilbene-2-O-β-D-glucoside on experimental inflammation and cyclooxygenase 2 activity. J Asian Nat Prod Res 2007;9:355–63.
Chen Y, Wang MF, Rosen RT, Ho CT. 2,2-Diphenyl-1-picrylhydrazyl radical scavenging active components from Polygonum multiflorum Thunb. J Agric Food Chem 1999;47: 2226–8.
Lin HW, Sun MX, Wang YH. Anti-HIV activities of the compounds isolated from Polygonum cuspidatum and Polygonum multiflorum. Planta Med 2010;70:889–92.
Wang MJ, Zhao RH, Wang WG, Mao XJ, Yu J. Lipid regulation effects of Polygoni multiflori radix, its processed products and its major substances on steatosis human liver cell line L02. J Ethnopharmacol 2012;139:287–93.
Fukuyama Y, Sato T, Asakawa Y, Takemoto T. A potent cytotoxic warburganal and related drimane-type sesquiterpenoids from Polygonum hydropiper. Phytochemistry 1982;21:2895–8.
Haraguchi H, Ohmi I, Sakai S, Fukuda A, Toihara Y, Fujimoto T, et al. Effect of Polygonum hydropiper sulfated flavonoids on lens aldose reductase and related enzymes. J Nat Prod 1996; 59:443–5.
Lv L, Cheng Y, Zheng T, Li X, Zhai R. Purification, antioxidant activity and antiglycation of polysaccharides from Polygonum multifforum Thunb. Carbohydr Polym 2014;99:765–73.
Lai XX, Li YP. Antitumor effect and mechanism of action of polysaccharides extracted from Polygonum perfoliatum L whole plant in human lung carcinoma A549 cell line. Trop J Pharm Res 2016;15:1243-9.
Yagi A, Uemura T, Okamura N, Haraguchi H, Imoto H, Hashimoto K. Antioxidative sulphated flavonoids in leaves of Polygonum hydropiper. Phytochemistry 1994;35:885-7.
Wang KJ, Zhang YJ, Yang CR. Antioxidant phenolic compounds from rhizomes of Polygonum paleaceum. J Ethnopharmacol 2005;96:483–7.
Peng Z, Strack D, Baumert A, Subramaniam R, Goh N, Chia T, et al. Antioxidant flavonoids from leaves of Polygonum hydropiper L. Phytochemistry 2003;62:219–28.
Wang, KW, Zhu JR, Shen LQ. A new lignan with anti-tumour activity from Polygonum perfoliatum L. Nat Prod Res 2013;27:568-73.
Kumar KS, Ganesan K, Rao PV. Antioxidant potential of solvent extracts of Kappaphycus alverezii (Doty) Doty–an edible seaweed. Food Chem 2008;107:289–5.
Kumaran A, Karunakaran J. In vitro antioxidant activities of methanol extracts of ï¬ve Phyllanthus species from India. LWT-Food Sci Technol 2007;40:344–52.
Ratty AK, Sunamoto J, Das NP. Interaction of flavonoids with 1,1-diphenyl-2-picrylhydrazyl free radical, liposomal membranes and soybean lipoxygenase-1. Biochem Pharmacol 1988;37:989-95.
Liu Y, Wu Y, Yuan K, Ji C, Hou AY, Yuan K, et al. Astragalin 2â€, 6â€-di-O-gallate from loropetalum chinense. Phytochemistry 1997;46:389-91.
Harborne JB, Williams CA. In: Harborne JB, Mabry TJ, Mabry H. Eds. The Flavonoids Chapman and Hall, London; 1975.
Wollenweber E, Marx D, Favre-Bonvin J, Voirin B, Kaouadji M. 3-metoxyflavones with unusual b-ring substitution from two species of Notholaena. Phytochemistry 1988;27:2673-6.
Yagi A, Uemura T, Okamura N, Haraguchi H, Imoto T, Hashimoto K. Antioxidative sulphated flavonoids in leaves of Polygonum hydropiper. Phytochemistry 1994;35:885-7.
Buchanan GW, Reyes-Zamora C, Clarke DE. A carbon-13 nuclear magnetic resonance investigation of some substituted methyl phenyl sulfide, sulfoxides, and sulfones. Can J Chem 1974;52:3895-904.
Mabry TJ, Markaham KR, Thomas MB. The systematic identification of flavonoids, Springer-verlag, Berlin; 1970.
Markham KR, Chari VM, Mabry TJ. The flavonoids: advances in research; Harbone JB, Mabry TJ. Eds. Chapman and Hall: London, UK; 1982.
Diaz MN, Frei B, Keaney JF, Vita JA. Antioxidants and atherosclerotic heart disease. N Engl J Med 1997;337:408-16.
Aruoma OI. Free radicals, oxidative stress and antioxidants in human and disease. J Am Oil Chem Soc 1998;75:199-212.
Brown JE, Rice-Evans CA. Luteolin-rich artichoke extract protects low-density lipoprotein from oxidation in vitro. Free Radical Res 1998;29:247-55.
Published
How to Cite
Issue
Section
