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Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers

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Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers molecules Review Update on Phytochemistry and Pharmacology of Naturally Occurring Resveratrol Oligomers Jie Shen 1,2, Qiang Zhou 1,2,3, Pei Li 1,2, Zhiqiang Wang 1,2,4, Shuangshuang Liu 1,2, Chunnian He 1,2,* ID , Chunhong Zhang 5,* and Peigen Xiao 1,2 1 Institute of Medicinal Plant Development, Chinese Academy of Medical Science, Peking Union Medical College, Beijing 100193, China; [email protected] (J.S.); [email protected] (Q.Z.); [email protected] (P.L.); [email protected] (Z.W.); [email protected] (S.L.); [email protected] (P.X.) 2 Laboratory of Bioactive Substances and Resources Utilization of Chinese Herbal Medicine, Ministry of Education, Beijing 100193, China 3 School of Graduate, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China 4 School of Pharmacy, Anhui Medical University, Hefei 230032, China 5 School of Pharmacy, Baotou Medical College, Baotou 014060, China * Correspondence: [email protected] (C.H.); [email protected] (C.Z.); Tel.: +86-10-5783-3165 (C.H.) Received: 11 October 2017; Accepted: 21 November 2017; Published: 24 November 2017 Abstract: Resveratrol oligomers (REVs), a major class of stilbenoids, are biosynthesized by regioselective oxidative coupling of two to eight units of resveratrol monomer. Due to their unique structures and pleiotropic biological activities, natural product chemists are increasingly focusing on REVs in the last few decades. This study presents a detailed and thorough examination of REVs, including chemical structures, natural resources, and biological activities, during the period of 2010–2017. Ninety-two new REVs compounds, including 39 dimers, 23 trimers, 13 tetramers, six resveratrol monomers, six hexamers, four pentamers, and one octamer, have been reported from the families of Dipterocarpaceae, Paeoniaceae, Vitaceae, Leguminosae, Gnetaceae, Cyperaceae, Polygonaceae Gramineae, and Poaceae. Amongst these families, Dipterocarpaceae, with 50 REVs, accounts for the majority, and seven genera of Dipterocarpaceae are involved, including Vatica, Vateria, Shorea, Hopea, Neobalanocarpus, Dipterocarpus, and Dryobalanops. These REVs have shown a wide range of bioactivities. Pharmacological studies have mainly focused on potential efficacy on tumors, bacteria, Alzheimer’s disease, cardiovascular diseases, and others. The information updated in this review might assist further research and development of novel REVs as potential therapeutic agents. Keywords: resveratrol oligomers; distribution; phytochemistry; pharmacology 1. Introduction Resveratrol oligomers (REVs), a major class of stilbenoids, are commonly biosynthesized by regioselective oxidative coupling of two to eight units of resveratrol monomer [1]. Some plants containing REVs have been used for a long time in traditional Asian medicine. For example, Nardostachys chinensis Batal (Valerianaceae), a traditional herbal tranquilizer in China, contains REVs as the active ingredient. The resin of Shorea species, rich in REVs, has been used as an astringent to treat diarrhea and dysentery in Malaysia [2–5]. Several pure REVs have been isolated from various plants. Based on pharmacological studies, REVs are reported to have multi-faceted biological activities [6–8], including antimicrobial, antioxidant, and antitumor effects, as well as cardiovascular protection. Due to their unique chemical structures and diverse biological activities, REVs have increasingly captured the attention of medicinal chemists [9,10]. Molecules 2017, 22, 2050; doi:10.3390/molecules22122050 www.mdpi.com/journal/molecules Molecules 2017, 22, 2050 2 of 26 As the research information on REVs has accumulated, several reviews appeared from 2010 to 2017 [1,11–19]. In 2013, the biosynthesis, chemistry, and proprieties of REVs in grapes were summarized by Riccardo et al. [11]; the structures of oligostilbenoids in Dipterocarpaceae plants and their biological activitiesMolecules were 2017 reviewed, 22, 2050 [12]. Another review published in 2013 [13] summarized 60 stilbenes, including2 of 24 27 REVs found from 2009 to 2013, but the source plants were not mentioned. In 2014, Lim et al. reviewed resveratrolby Riccardo and its et oligomers al. [11]; the in modulatingstructures of sphingolipid oligostilbenoids metabolism in Dipterocarpaceae and signaling plants in diseasesand their [14]; biological activities were reviewed [12]. Another review published in 2013 [13] summarized 60 stilbenes, another article in 2014 reviewed REVs for the prevention and treatment of cancers [15]. Of two papers including 27 REVs found from 2009 to 2013, but the source plants were not mentioned. In 2014, Lim et al. published in 2015, one focused on biosynthesis as well as some bioactivities [16]; another one focused reviewed resveratrol and its oligomers in modulating sphingolipid metabolism and signaling in on thediseases diverse [14]; bioactivities another article of ologostibenes in 2014 reviewed [17]. OneREVs paper for the in prevention 2017 [18] choseand treatment “cancer of chemopreventive cancers [15]. potential”Of two as thepapers topic. published in 2015, one focused on biosynthesis as well as some bioactivities [16]; Asanother phytochemistry one focused andon the pharmacology diverse bioactivities of naturally of ologostibenes occurring [17]. REVs One has paper progressed, in 2017 [18] our chose review provides“cancer a detailed chemopreventive and thorough potential” examination as the topic. of their chemical structures, natural resources, and biologicalAs phytochemistry activities, from and 2010 pharmacology to 2017. In of this natura period,lly occurring 92 new REVsREVs has were progressed, isolated andour review identified, includingprovides 39 dimers, a detailed 23 trimers, and thorough 13 tetramers, examination six resveratrol of their monomers,chemical structures, six hexamers, natural four resources, pentamers, and and one octamer.biological However, activities, no from resveratrol 2010 to heptamer2017. In this has period, been discovered. 92 new REVs These were REVs isolated are mostlyand identified, distributed including 39 dimers, 23 trimers, 13 tetramers, six resveratrol monomers, six hexamers, four pentamers, in the following seven families: Dipterocarpaceae, Paeoniaceae, Vitaceae, Leguminosae, Gnetaceae, and one octamer. However, no resveratrol heptamer has been discovered. These REVs are mostly Cyperaceae, and Polygonaceae. Most REVs were isolated from the family of Dipterocarpaceae, as in distributed in the following seven families: Dipterocarpaceae, Paeoniaceae, Vitaceae, Leguminosae, the past.Gnetaceae, The pharmacological Cyperaceae, and activitiesPolygonaceae. of REVs Most areREVs mainly were isolated concentrated from the onfam antibacterial,ily of Dipterocarpaceae, antioxidant, anti-Alzheimer’sas in the past. disease, The pharmacological anti-Parkinson’s activities disease, of anti-tumors, REVs are mainly and cardiovascular concentrated on protection, antibacterial, as well as liverantioxidant, protective effects.anti-Alzheimer’s The review disease, aims toanti-Parki providenson’s readers disease, with comprehensiveanti-tumors, and information cardiovascular on the progressprotection, of REVs. as well as liver protective effects. The review aims to provide readers with comprehensive information on the progress of REVs. 2. Phytochemistry 2. Phytochemistry Chemical structure analysis showed that REVs were polymerized from two to eight, or even more, resveratrolChemical units that structure have great analysis structural showed diversity that REVs and were include, polymerized but are from not limitedtwo to eight, to, the or following even features:more, (1) aresveratrol degree of polymerizationunits that have great up to structural eight; (2) formationdiversity and of dihydrobenzofuran(s)include, but are not limited or a benzofuran to, the following features: (1) a degree of polymerization up to eight; (2) formation of dihydrobenzofuran(s) or a chroman; (3) O-glucosylation; (4) condensation of a phenylpropanoid; and (5) formation of a or a benzofuran or a chroman; (3) O-glucosylation; (4) condensation of a phenylpropanoid; and cyclohexa-2,5-dienone.(5) formation of a Chemicalcyclohexa-2,5-dienone. structures of Chemical the 92 new structures REVs from of the dimer 92 new tooctamer REVs from are dimer compiled to in Figuresoctamer1–8, and are their compiled plant in sources Figures are 1–8, listed and intheir Table plant A1 sources in Appendix are listedA. in Table A1 in Appendix A. FigureFigure 1. The 1. The polymerization polymerization situations situations of of resveratrol resveratrol oligomers from from 2010 2010 to to2017. 2017. Molecules 2017, 22, 2050 3 of 26 2.1. ResveratrolMolecules 2017 Monomers, 22, 2050 3 of 24 Resveratrol monomers are compounds that possess one stilbene skeleton with various substituting 2.1. Resveratrol Monomers groups. Many resveratrol derivatives have been found in natural products and have been obtained from chemical synthesisResveratrol and monomers structure are modifications. compounds that Due po tossess the simple one stilbene structures skeleton and diversewith various biological Molecules 2017, 22, 2050 3 of 24 activities,substituting resveratrol groups. monomers Many resver haveatrol been derivatives intensively have studied. been found Six newin natural resveratrol products monomers and have were been obtained from chemical synthesis and structure modifications. Due to the simple structures and successfully2.1. Resveratrol isolated Monomers from 2010 to 2017, though the speed
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