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Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants

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Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants molecules Article Ellagitannins and Oligomeric Proanthocyanidins of Three Polygonaceous Plants Yun-Qiu Li 1,2, Masako Kitaoka 3, Juri Takayoshi 3, Ya-Feng Wang 4, Yosuke Matsuo 1 , Yoshinori Saito 1, Yong-Lin Huang 4, Dian-Peng Li 4, Gen-ichiro Nonaka 5, Zhi-Hong Jiang 6 and Takashi Tanaka 1,* 1 Department of Natural Product Chemistry, Graduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; [email protected] (Y.-Q.L.); [email protected] (Y.M.); [email protected] (Y.S.) 2 College of Medical Laboratory Science, Guilin Medical University, 109, Huancheng North 2 Road, Guilin 541004, China 3 Department of Natural Product Chemistry, School of Pharmaceutical Sciences, Nagasaki University, 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan; [email protected] (M.K.); [email protected] (J.T.) 4 Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin 541006, China; [email protected] (Y.-F.W.); [email protected] (Y.-L.H.); [email protected] (D.-P.L.) 5 Usaien Pharmaceutical Company, Ltd., 1-4-6 Zaimoku, Saga 840-0055, Japan; [email protected] 6 Institute for Applied Research in Medicine and Health, Macau University of Science and Technology, Taipa, Macau 999078, China; [email protected] * Correspondence: [email protected]; Tel.: +81-95-819-2432 Abstract: The aim of this study was to characterize hydrolyzable tannins in Polygonaceous plants, as only a few plants have previously been reported to contain ellagitannins. From Persicaria chinensis, a new hydrolyzable tannin called persicarianin was isolated and characterized to be 3-O-galloyl-4,6-(S)- dehydrohexahydroxydiphenoyl-D-glucose. Interestingly, acid hydrolysis of this compound afforded Citation: Li, Y.-Q.; Kitaoka, M.; ellagic acid, despite the absence of a hexahydroxydiphenoyl group. From the rhizome of Polygonum Takayoshi, J.; Wang, Y.-F.; Matsuo, Y.; Saito, Y.; Huang, Y.-L.; Li, D.-P.; runcinatum var. sinense, a large amount of granatin A, along with minor ellagitannins, helioscpoinin Nonaka, G.-i.; Jiang, Z.-H.; et al. A, davicratinic acids B and C, and a new ellagitannin called polygonanin A, were isolated. Based Ellagitannins and Oligomeric on 2D nuclear magnetic resonance (NMR) spectroscopic examination, the structure of polygonanin Proanthocyanidins of Three A was determined to be 1,6-(S)-hexahydroxydiphenoyl-2,4-hydroxychebuloyl-β-D-glucopyranose. Polygonaceous Plants. Molecules 2021, These are the second and third hydrolyzable tannins isolated from Polygonaceous plants. In addition, 26, 337. https://doi.org/10.3390/ oligomeric proanthocyanidins of Persicaria capitatum and P. chinensis were characterized by thiol molecules26020337 degradation. These results suggested that some Polygonaceous plants are the source of hydrolyzable tannins not only proanthocyanidins. Academic Editor: Luca Rolle Received: 10 December 2020 Keywords: ellagitannin; hydrolyzable tannin; proanthocyanidin; Persicaria; Polygonum; Polygo- Accepted: 7 January 2021 naceae Published: 11 January 2021 Publisher’s Note: MDPI stays neu- tral with regard to jurisdictional clai- 1. Introduction ms in published maps and institutio- nal affiliations. Ellagitannins are hydrolyzable tannins containing hexahydroxydiphenoyl (HHDP) groups and related acyl groups. Recently, their high structural diversity and biological activities have attracted intense interest amongst natural product chemists [1–5]. Compared to proanthocyanidins (synonym (syn.) condensed tannins), distribution of ellagitannins Copyright: © 2021 by the authors. Li- in the plant kingdom is relatively limited. Among Polygonaceous plants, only 2,3,4-tri-O- censee MDPI, Basel, Switzerland. galloyl-1,6-(S)-HHDP-β-D-glucose (davidiin, 1) has been isolated from Persicaria capitatum This article is an open access article (syn. Polygonum capitatum)[6]; its biological activity and metabolism have also been distributed under the terms and con- reported [7–9]. More recently, the presence of geraniin and chebulagic acid in the aerial parts ditions of the Creative Commons At- of Persicaria chinense var. hispidum was suggested by the use of high-performance liquid tribution (CC BY) license (https:// chromatography (HPLC)-mass spectroscopy (MS) [10]. In the course of chemical studies creativecommons.org/licenses/by/ on ellagitannins, we analyzed aqueous CH CN extracts of eight Polygonaceous plants, 4.0/). 3 Molecules 2021, 26, 337. https://doi.org/10.3390/molecules26020337 https://www.mdpi.com/journal/molecules Molecules 2021, 26, 337 2 of 11 Molecules 2020, 25, x Reynoutria japonica, Persicaria perfoliata, P. longiseta, P. lapathifolia, P. capitata, P. chinensis2 of 11, Molecules 2020, 25, x 2 of 11 P. filiformis, and P. thunbergii, by HPLC-diode array detector (DAD) analysis (Figure S1, Supplementary Materials). In the study, only the extracts of P. capitata and P. chinensis (Figure S1, Supplementary(Figure S1, Supplementary Materials). In Materials the study,). Inonly the the study, extracts only of the P. extractscapitata ofand P. P. capitata and P. showed peaks with UV absorption characteristic to ellagitannins (Figure1). The results chinensis showedchinensis peaks showed with UV peaks absorption with UV characteristic absorption characteristic to ellagitannins to ellagitannins(Figure 1). The (Figure 1). The were consistent with the above-mentioned studies; the major ellagitannin of P. capitata results were consistentresults were with consistent the above with-mentioned the above studies-mentioned; the ma studiesjor ellagitannin; the major of ellagitannin P. cap- of P. cap- was davidiin (1), and P. chinensis contains geraniin (2) (Figure2). In addition, we found itata was davidiinitata was (1), davidiinand P. chinensis (1), and contains P. chinensis geraniin contains (2) (Figuregeraniin 2) (.2 )In (Figure addition, 2). weIn addition, we that the rhizome of Polygonum runcinatum var. sinense, a Chinese perennial plant used found that thefound rhizome that theof Polygonum rhizome of runcinatum Polygonum var. runcinatum sinense, avar. Chinese sinense perennial, a Chinese plant perennial plant as a folk medicine for detoxification and hemostasis, contains ellagitannins as the major used as a folkused medicine as a folk for medicinedetoxification for detoxification and hemostasis, and containshemostasis, ellagitannins contains ellagitanninsas the as the constituents. This paper describes the isolation of phenolic substances from these three major constituents.major constituents.This paper describes This paper the describes isolation theof phenolic isolation substance of phenolics from substance these s from these plants and structural determination of the two new ellagitannins obtained from Persicaria three plants andthree structur plantsal and determination structural determination of the two new of ellagitanninsthe two new ellagitanninsobtained from obtained Per- from Per- sicariachinensis chinensisand Polygonum and Polygonum runcinatum runcinatumvar. sinense. var. sinense.In addition, In addition, proanthocyanidin proanthocyanidin oligomers oli- sicaria chinensisfrom andPersicaria Polygonum capitata runcinatumand Persicaria var. sinense. chinensis In addition,were chemically proanthocyanidin characterized. oli- gomers from gomersPersicaria from capitata Persicaria and Persicaria capitata and chinensis Persicaria were chinensis chemically were characterized. chemically characterized. (a) 1 CH-09 [MaxABS (200.0--550.0 nm)] (b) tsurusoba - CH5 (c) 7 Euphorbia - CH5 (a) 1800000 1 CH-09 [MaxABS (200.0--550.0 nm)] (b) tsurusoba - CH5 (c) 7 Euphorbia - CH5 1800000 1600000 1600000 600000 1400000 600000 1400000 Fl 1200000 Fl 1200000 Fl 2 1000000 Fl 4000002 1000000 1000000 400000 Fl 1000000 800000 Intensity[µAU] Fl Intensity[µV] 3 800000 Fl Intensity[µV] Intensity[µAU] Intensity[µV] 3 600000 Fl Intensity[µV] 600000 200000 400000 200000 400000 200000 200000 abs) (max absorption UV -0 UV absorption (max abs) (max absorption UV 0 0 -0 0 0 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0 10 20 Retention 30 Time [min] 40 50 min 0 10 20 30 40 50 min 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0 10 20 Retention 30 Time [min] 40 50 min 0 10 20 Retention 30 Time [min] 40 50 min 0 10 20 30 40 50 min 0.0 10.0 20.0 30.0 40.0 50.0 60.0 0 10 20 Retention 30 Time [min] 40 50 min Figure 1.1. HPLC profilesprofiles ofof 60%60% CH CH33CNCNextracts extracts of of ( a()a)Persicaria Persicaria capitata capitata,(,b ()bPersicaria) Persicaria chinensis chinensisand and (c) (Polygonumc) Polygonum runcinatum runcina- Figure 1. HPLC profiles of 60% CH3CN extracts of (a) Persicaria capitata, (b) Persicaria chinensis and (c) Polygonum runcina- tum var. sinense. 1: davidiin, 2: geraniin, 3: persicarianin, 7: granatin A and Fl: flavonoid glycosides. tum var. sinense.var. 1: sinense.davidiin,1: 2 davidiin,: geraniin,2: 3 geraniin,: persicarianin,3: persicarianin, 7: granatin7 A: granatin and Fl: flavonoid A and Fl: glycosides. flavonoid glycosides. HO HO OH OH HO HO OH OH HO HO OH OH HO HO OH OH R HO OH R HO OH HO OH S HO OH S (S)-HHDP OH (S)-HHDP (R)-HHDP OOH O O (R)-HHDP O O O O O O O O O OH O O O O OH HO O O O HO O OH O O O OH O OH HO O OH HO O OH O O O O OHO O O O O O O O H O O O HOO O OO O HO O OH H O H OH galloyl HO H galloyl HO O OH HO O OHO OH HO O OH HO HO O HO OH HO OH HO O OH HO HO O OH HO OH (R)-DHHDP HOOHHO O OH (R)-DHHDP OH 1 2 1 2 Figure 2. Structures of davidiin (1) from Persicaria capitata and geraniin (2) from Persicaria chinensis. FigureFigure 2. 2.Structures Structures of of davidiin davidiin (1 )(1 from) fromPersicaria Persicaria capitata capitataand and geraniin geraniin (2 )(2 from) fromPersicaria Persicaria chinensis.
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