Isolation and Determination of Phenolic Glycosides and Anthraquinones from Rhizomes of Various Reynoutria Species

Abstract

Giant knotweeds of the genus Reynoutria (syn. Fallopia)–Reynoutria japonica, Reynoutria sachalinensis, and a hybrid of them, Reynoutria x bohemica–are noxious invasive plants in Europe and North America. R. japonica is a traditional East Asian (Japan and China) drug (Polygoni cuspidati rhizoma). Recently, it has been included in European Pharmacopoeia as one of the traditional Chinese medicinal herbs. In this study, a reversed-phase high performance liquid chromatography method with diode array detector and time-of-flight mass spectrometry was developed and validated for the profiling of rhizomes from European invasive populations and Polygoni cuspidati rhizoma purchased in China. Twenty-five compounds were identified, mainly stilbenes, anthraquinones, flavan-3-ols, and phenylpropanoid esters. Tatariside B, hydropiperoside, vanicoside C, a new compound (3,6-O-di-p-coumaroyl)-β-fructofuranosyl-(2 → 1)-(2′-O-acetyl-6′-O-feruloyl)-β-glucopyranoside) were reported for the first time in these raw materials. Six compounds from three phytochemical classes–stilbenes: piceid and resveratrol; anthraquinones: emodin and physcion; hydroxycinnamic sucrose esters: vanicosides A and B–were quantified using the validated method. R. japonica from China contained twice as many stilbenoids than samples from Poland (piceid 14.83 mg/g dm vs. 7.45 mg/g and resveratrol 1.29 mg/g vs. 0.65 mg/g). R. sachalinensis rhizomes contained lower quantities of anthraquinones and no detectable stilbenes, which together with higher amounts of hydroxycinnamic glycosides makes it easily distinguishable from the other two. The phytochemical profile of R. x bohemica was intermediate between the two parent species.

Key words

LC-MS - phenolic glycosides - anthranoids - stilbenoids - flavan-3-ols - Polygonaceae - Reynoutria

• References

• 1 Bailey J. The Japanese knotweed invasion viewed as a vast unintentional hybridisation experiment. Heredity (Edinb) 2013; 110: 105-110
• 2 European Pharmacopoeia. 9th ed. Strasburg, France: European Directorate for the Quality of Medicines; 2017: 1481-1483
• 3 Xi S, Gong Y. Essentials of Chinese Materia Medica and medical Formulas. London: Academic Press – Elsevier; 2017: 153
• 4 Editorial Committee of Chinese Pharmacopoeia. Chinese Pharmacopoeia. Beijing: Medical Science and Technology Press; 1977: 340
• 5 Peng W, Qin R, Li X, Zhou H. Botany, phytochemistry, pharmacology, and potential application of Polygonum cuspidatum Sieb.et Zucc.: a review. J Ethnopharmacol 2013; 148: 729-745
• 6 Conolly AP. The distribution and history in the British Isles of some alien species of Polygonum and Reynoutria . Watsonia 1977; 11: 291-311
• 7 Bímová K, Mandák B, Pyšek P. Experimental study of vegetative regeneration in four invasive Reynoutria taxa (Polygonaceae). Plant Ecol 2003; 166: 1-11
• 8 Bailey JP, Conoll AP. Prize-winners to pariahs – a history of Japanese Knotweed s.l. (Polygonaceae) in the British Isles. Watsonia 2000; 23: 93-110
• 9 Fan P, Hay AE, Marston A, Lou H, Hostettmann K. Chemical variability of the invasive neophytes Polygonum cuspidatum Sieb. and Zucc. and Polygonum sachalinensis F. Schmidt ex Maxim. Biochem Syst Ecol 2009; 37: 24-34
• 10 Beňová B, Adam M, Onderková K, Královský J, Krajíček M. Analysis of selected stilbenes in Polygonum cuspidatum by HPLC coupled with CoulArray detection. J Sep Sci 2008; 31: 2404-2409
• 11 Tiébré MS, Bizoux JP, Hardy OJ, Bailey JP, Mahy G. Hybridization and morphogenetic variation in the invasive alien Fallopia (Polygonaceae) complex in Belgium. Am J Bot 2007; 94: 1900-1910
• 12 Pharmacopoeia of China. Part 1. Beijing: China Medical Science and Technology Press; 2005: 180-181
• 13 Yi T, Zhang H, Cai Z. Analysis of Rhizoma polygoni cuspidati by HPLC and HPLC-ESI/MS. Phytochem Anal 2007; 18: 387-392
• 14 Qian G, Leung SY, Lu G, Leung KS. Optimization and validation of a chromatographic method for the simultaneous quantification of six bioactive compounds in Rhizoma et Radix polygoni cuspidati . J Pharm Pharmacol 2008; 60: 107-113
• 15 Chu X, Sun A, Liu R. Preparative isolation and purification of five compounds from the Chinese medicinal herb Polygonum cuspidatum Sieb. et Zucc by high-speed counter-current chromatography. J Chromatogr A 2005; 1097: 33-39
• 16 Kumagai H, Kawai Y, Sawano R, Kurihara H, Yamazaki K, Inoue N. Antimicrobial substances from rhizomes of the giant knotweed Polygonum sachalinense against the fish pathogen Photobacterium damselae subsp. piscicida . Z Naturforsch C 2005; 60: 39-44
• 17 Fu J, Wang M, Guo H, Tian Y, Zhang Z, Song R. Profiling of components of Rhizoma et Radix polygoni cuspidati by high-performance liquid chromatography with ultraviolet diode-array detector and ion trap/time-of-flight mass spectrometric detection. Pharmacogn Mag 2015; 11: 486-501
• 18 Fan P, Terrier L, Hay A, Marston A, Hostettmann K. Antioxidant and enzyme inhibition activities and chemical profiles of Polygonum sachalinensis F. Schmidt ex Maxim (Polygonaceae). Fitoterapia 2010; 81: 124-131
• 19 Chen X, Wang R, Liu B. An update on oligosaccharides and their esters from traditional Chinese medicines: chemical structures and biological activities. Evid Based Complement Alternat Med 2015; 2015: 512675
• 20 Zhang X, Thuong PT, Jin W, Su ND, Sok DE, Bae K, Kang SS. Antioxidant activity of anthraquinones and flavonoids from flower of Reynoutria sachalinensis . Arch Pharm Res 2005; 28: 22-27
• 21 Seo EJ, Kuete V, Kadioglu O, Krusche B, Schröder S, Greten HJ, Arend J, Lee IS, Efferth T. Antiangiogenic activity and pharmacogenomics of medicinal plants from traditional Korean medicine. Evid Based Complement Alternat Med 2013; 2013: 131306
• 22 Zheng C, Hu C, Ma X, Peng C, Zhang H, Qin L. Cytotoxic phenylpropanoid glycosides from Fagopyrum tataricum (L.) Gaertn. Food Chem 2012; 132: 433-438
• 23 Takasaki M, Kuroki S, Kozuka M, Konoshima T. New phenylpropanoid esters of sucrose from Polygonum lapathifolium . J Nat Prod 2001; 64: 1305-1308
• 24 Brown LL, Larson SR, Sneden AT. Vanicosides CF, new phenylpropanoid glycosides from Polygonum pennsylvanicum . J Nat Prod 1998; 61: 762-766
• 25 Vastano BC, Chen Y, Zhu N, Ho CT, Zhou Z, Rosen RT. Isolation and identification of stilbenes in two varieties of Polygonum cuspidatum . J Agric Food Chem 2000; 48: 253-256
• 26 Sołtysiak J. Właściwości biologiczne i ekologiczne inwazyjnych chwastów z rodzaju rdestowiec (Fallopia spp.) w warunkach miejskich na przykładzie Wrocławia [dissertation]. Wrocław: University of Environmental and Life Studies; 2012
• 27 Kovářová M, Frantík T, Koblihová H, Bartůňková K, Nývltová Z, Vosátka M. Effect of clone selection, nitrogen supply, leaf damage and mycorrhizal fungi on stilbene and emodin production in knotweed. BMC Plant Biol 2011; 11: 98