A NEW NAPHTHOQUINONE ISOLATED FROM POLYGONUM MULTIFLORUM (POLYGONACEAE)
Keywords:
Naphthoquinones, Anthraquinones, Stilbenes, Isolation, Polygonum multiflorum, Spectroscopic analysisAbstract
Objective: This research is mainly focused towards isolation and structural elucidation of pure compounds from the extract and fractions of Polygonum multiflorum through silica gel column chromatography.
Methods: The air dried rhizomes were extracted with Me2CO (acetone), MeOH (methanol) and H2O (water). The Me2CO extract was fractionated into CHCl3 (chloroform) and residue. The chloroform-soluble portion and MeOH extract were subjected to silica gel column chromatography for the isolation of pure compounds. The isolated compounds were then determined by the use of spectroscopic analysis of HRFABMS, 1H, 13C NMR, UV and IR spectra.
Results: CHCl3 soluble portion of Me2CO and MeOH extract of P. multiflorum led to the isolation of one new naphthoquinone and eight known compounds including four anthraquinones, one naphthoquinone and two stilbenes.
Conclusion: The obtained results will be very useful for the further evaluation various biological studies.
Downloads
References
Wang KJ, Zhang YJ, Yang CR. Antioxidant phenolic compounds from rhizomes of Polygonum paleaceum. J Ethnopharmacol 2005;96:483-7.
Yim TK, Wu WK, Pak WF, Mak DH, Liang SM, Ko KM. Myocardial protection against ischemia-reperfusion injury by a Polygonum multiflorum extract supplemented 'Dang-Gui decoction for enriching blood', a compound formulation, ex vivo. Phytother Res 2000;14:195-9.
Bralley EE, Greenspan P, Hargrove JL, Wicker L, Hartle DK. Topical anti-inflammatory activity of Polygonum cuspidatum extracts in the TPA model of mouse ear inflammation. J Inflamm 2008;8:1-5.
Wang T, Gu J, Wu PF, Wang F, Xiong Z, Yang YJ, et al. Protection by tetrahydroxy-stilbene glucoside against cerebral ischemia: involvement of JNK, SIRT1, and NF-kappa B pathways and inhibition of intracellular ROS/RNS generation. Free Radical Biol Med 2009;47:229-40.
Um MY, Choi WH, Aan JY, Kim SR, Ha TY. Protective effect of Polygonum multiflorum Thunb on amyloid beta-peptide 25-35 induced cognitive deficits in mice. Ethnopharmacology 2006;104:144-8.
Li X, Matsumoto K, Murakami Y, Tezuka Y, Wu Y, Kadota S. Neuroprotective effects of Polygonum multiflorum on nigrostriatal dopaminergic degeneration induced by paraquat and maneb in mice. Pharmacol Biochem Behav 2005;82:345-52.
Lopez SN, Sierra MG, Gattuso SJ, Furlan RL, Zacchino SA. An unusual homo iso flavanone and a structurally related dihydrochalcone from Polygonum ferrugineum (Polygonaceae). Phytochemistry 2006;67:2152-8.
Duwiejua M, Zeitlin IJ, Gray AI, Waterman PG. The anti-inflammatory compounds of Polygonum bistorta: isolation and characterisation. Planta Med 1999;65:371-4.
Huan YQ, Chao FZ, Mian Z, Jian QL, Zheng TW. Three new anthraquinones from Polygonum Cillinerve. Chin Chem Lett 1990;16:1050-2.
Sun X, Sneden AT. Neoflavonoids from Polygonum perfoliatum. Planta Med 1999;65:671-3.
Murai Y, Kashimura S, Tamezawa S, Hashimoto T, Takaoka S, Asakawa Y, et al. Absolute configuration of (6S, 9S)-rose oxide from Polygonum hydropiper. Planta Med 2001;67:480-1.
Midori T, Satoshi K, Mutsuo K, Takao K. New Phenylpropanoid esters of sucrose from Polygonum lapathifolium. J Nat Prod 2001;64:1305–8.
Hyoung JK, Eun RW, Hokoon P. A novel lignan and flavonoids from Polygonum aviculare. J Nat Prod 1994;57:581–6.
Datta BK, Datta SK, Rashid MA, Nash RJ, Sarker SD. A sesquiterpene acid and flavonoids from Polygonum viscosum. Phytochemistry 2000;54:201-5.
Derita MG, Leiva ML, Zacchino SA. Influence of plant part, the season of collection and content of the main active constituent, on the antifungal properties of Polygonum acuminatum Kunth. J Ethnopharmacol 2009;124:377-83.
Xiao K, Xuan L, Xu Y, Bai D. Stilbene glycoside sulfates from Polygonum cuspidatum. J Nat Prod 2000;63:1373-6.
Bidyut KD, Sadhan KD, Mohammad AR, Satyajit DS. Flavonoids from Polygonum stagninum (Polygonaceae). Biochem Syst Ecol 2002;30:693-6.
Yang PY, Almofti MR, Lu L, Kang H, Zhang J, Li TJ, et al. Reduction of atherosclerosis in cholesterol-fed rabbits and decrease of expressions of intracellular adhesion molecule-1 and vascular endothelial growth factor in foam cells by a water-soluble fraction of Polygonum multiflorum. J Pharmacol Sci 2005;99:294-300.
Liu LP, Liao ZP, Yin D, Li WD, Liu D, Li Q, et al. The protective effects of Polygonum multiflorum stilbene glycoside preconditioning in an ischemia/reperfusion model of HUVECs. Acta Pharmacol Sin 2010;31:405-12.
Yao S, Li Y, Kong L. Preparative isolation and purification of chemical constituents from the root of Polygonum multiflorum by high-speed counter-current chromatography. J Chromatogr A 2006;115:64-71.
Yi T, Leung KS, Lu GH, Zhang H, Chan K. Identification and determination of the major constituents in traditional Chinese medicinal plant Polygonum multiflorum thunb by HPLC coupled with PAD and ESI/MS. Phytochem Anal 2007;18:181-7.
Lifeng H, Bin W, Guixiang P, Yufei W, Xinbo S, Xiumei G. UPLC-PDA analysis for simultaneous quantification of four active compounds in crude and processed rhizome of Polygonum multiflorum Thunb. J Chromatographia 2009;70:657-9.
Byoung MK, Sung HK, Nam IB, Sa IL, Eun JK, Jae HY, et al. Farnesyl protein transferase inhibitory components of Polygonum multiflorum. Arch Pharm Res 2009;2:495-9.
Thomson RH. Naturally occurring quinones. Academic press: London; 1971. p. 50.
Craven RA. Sensitive colour reaction for certain quinones. J Chem Soc 1931;1:1605-6.
Ying Bo Li, Zhu Qing Lin, Zai Jun Zhang, Mei Wei Wang, Huan Zhang, Qing-Wen Zhang, et al. Protective, antioxidative and antiapoptotic effects of 2-methoxy-6-acetyl-7-methyljuglone from Polygonum cuspidatum in PC12 cells. Planta Med 2011;77:354-61.
Yang XW, Gu ZM, Ma CM, Masao H, Tsuneo N. A new indole derivate from Polygonum multiflorum thunb. Zhongcaoyao 1998;29:5-11.
Li JB, Lin M. The study on the constituents of the roots of Polygonum multiflorumThunb. Zhongcaoyao 1993;24:115-8.
Zhang ZG, Lu TS, Yao QQ. Study on the anthraquinone components of the roots of Polygonum multiflorum thunb. Zhongcaoyao 2006;37:1311-3.
Lin Hu, Na Na Chen, Qun Hu, Cui Yang, Qing-Song Yang, Fang-Fang Wang. An unusual piceatannol dimer isolated from Rheum austral with antioxidant activity. Molecules 2014;19:11453-64.
Robert H. Cichewicz and Samir AK. Biotransformation of resveratrol to piceid by bacillus aereus. J Nat Prod 1998;61:1313-4.
Tsutomu Hatano, Hiroshi Uerayashi, Hideyuki Ito, Sumiko Shiota, Tomofusa Tsuchiya, Takeshi Yoshida. Phenolic constituents of cassia seeds and antibacterial effect of some naphthalenes and anthaquinones on methicillin-resistant staphylococcus aureus. Chem Pharm Bull 1999;47:1121-7.