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Structural Revisions in Natural Ellagitannins

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Structural Revisions in Natural Ellagitannins molecules Review Structural Revisions in Natural Ellagitannins Hidetoshi Yamada 1,* ID , Shinnosuke Wakamori 1 ID , Tsukasa Hirokane 2 ID , Kazutada Ikeuchi 3 ID and Shintaro Matsumoto 1 1 School of Science and Technology, Kwansei Gakuin University, Sanda 669-1337, Japan; [email protected] (S.W.); [email protected] (S.M.) 2 Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770-8514, Japan; [email protected] 3 Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo 060-0810, Japan; [email protected] * Correspondence: [email protected]; Tel.: +81-795-65-8342 Received: 18 June 2018; Accepted: 17 July 2018; Published: 30 July 2018 Abstract: Ellagitannins are literally a class of tannins. Triggered by the oxidation of the phenolic parts on β-pentagalloyl-D-glucose, ellagitannins are generated through various structural conversions, such as the coupling of the phenolic parts, oxidation to highly complex structures, and the formation of dimer and lager analogs, which expand the structural diversity. To date, more than 1000 natural ellagitannins have been identified. Since these phenolic compounds exhibit a variety of biological activities, ellagitannins have potential applications in medicine and health enhancement. Within the context of identifying suitable applications, considerations need to be based on correct structural features. This review describes the structural revisions of 32 natural ellagitannins, namely alnusiin; alnusnin A and B; castalagin; castalin; casuarinin; cercidinin A and B; chebulagic acid; chebulinic acid; corilagin; geraniin; isoterchebin; nobotanin B, C, E, G, H, I, J, and K; punicalagin; punicalin; punigluconin; roxbin B; sanguiin H-2, H-3, and H-6; stachyurin; terchebin; vescalagin; and vescalin. The major focus is on the outline of the initial structural determination, on the processes to find the errors in the structure, and on the methods for the revision of the structure. Keywords: ellagitannin; structure; revision 1. Introduction Tannins are astringent polyphenolic compounds with high diversity in biological activities [1–3]. Many of the compounds have antioxidative effects and affect various organisms, such as fungi, tumor cells, and viruses. Originally, the term tannin meant a compound that could be used for the tanning of animal hides. Today, tannins are divided into multiple classes according to the source and the chemical structures; however, they are roughly classified into two categories: condensed and hydrolyzable tannins [4,5]. Of the two, ellagitannins belong to the hydrolyzable tannins. Ellagitannins arise through biosynthetic pathways that allow for the production of diversity. In the early stage of the biosynthesis, the galloyl groups of the β-pentagalloyl glucose (1) couple oxidatively to produce the hexahydroxydiphenoyl (HHDP) group (Figure1)[ 6–10]. Two of the five galloyl groups of 1 can couple and, in addition, the occurrence of R or S axial chirality on the HHDP group may be possible. Therefore, the number of combinations is 20 (5C2 × 2). After the occurrence of the first HHDP group, the production of the second HHDP group as cuspinin ((aR,aS)-2) and the cleavage of the ester bonds of the HHDP and the rest of the galloyl groups as corilagin ((aR)-3) may expand the variation. The oxidative coupling continues further to construct the trimer and tetramer of the galloyl group, which are called the nonahydroxytriphenoyl (NHTP) (alias: flavogallonyl) and gallagyl groups, respectively [11,12]. In addition, the galloyl and HHDP groups can connect Molecules 2018, 23, 1901; doi:10.3390/molecules23081901 www.mdpi.com/journal/molecules Molecules 2018, 23, 1901 2 of 46 Molecules 2018, 23, x FOR PEER REVIEW 2 of 46 oxidativelyoxidatively throughthrough aa C–OC–O bond,bond, whichwhich producesproduces sanguisorboyl,sanguisorboyl, tergalloyl, valoneoyl, valoneoyl, and and other other groupsgroups [ 13[13].]. ProductionProduction ofof thethe C–OC–O connectedconnected componentscomponents often involves involves the the generation generation of of dimeric dimeric andand larger larger ellagitannins ellagitannins to drasticallyto drastically increase increase the diversity.the diversity. The HHDPThe HHDP group group can be furthercan be oxidizedfurther tooxidized form the to dehydrohexahydroxydiphenoylform the dehydrohexahydroxydiphen (DHHDP),oyl (DHHDP), chebuloyl, chebuloyl, and other and groups, other groups, which which brings thebrings structures the structures beyond thebeyond patterned the patterned restriction. restri Further,ction. ellagitanninsFurther, ellagita cannnins join to can the componentsjoin to the outsidecomponents of ellagitannins, outside of ellagitannins, such as acutissimin such as A acutissimin and hirsunin, A toand illustrate hirsunin, illimitable to illustrate possibilities illimitable in structurepossibilities [14, 15in ].structure [14,15]. Figure 1. The oxidative intramolecular coupling of the galloyl groups and the structures of Figure 1. The oxidative intramolecular coupling of the galloyl groups and the structures of components components of ellagitannin, acutissimin A, and hirsunin. of ellagitannin, acutissimin A, and hirsunin. The structural diversity expands in the direction that makes the structures become more complex.The structural Today, structures diversity of expandscomplicated in theellagi directiontannins can that be makes elucidated the structures. However, become during their more complex.development, Today, studies structures for structural of complicated determinations ellagitannins had tackled can be the elucidated. most difficult However, subjects duringat the time. their development,Therefore, situations studies in for which structural it was determinationsdifficult to narrow had down tackled the theoptions most or difficult which led subjects to incorrect at the time.structures Therefore, could not situations be avoided. in which The reported it was difficultstructures to have narrow been down exposed the to options verification or which by history, led to incorrectincluding structures the development could not of beanalytical avoided. methods The reported and confirmation structures haveby chemical been exposed synthesis, to verification and some byof history,them were including revised. the developmentIn the meantime, of analytical the reported methods structures and confirmation were diffused by chemical by a secondary synthesis, andmedium, some ofsuch them as books, were revised. reviews, In and the websites. meantime, Although the reported the structures structures were were revised diffused afterward, by a secondary most medium,of the exhibited such as information books, reviews, remains and websites.as it was, Althoughwhich causes the structuresconfusion and were misunderstanding. revised afterward, mostHence, of thereviewing exhibited structural information revisions remains is worthwhile as it was, whichas Amagata causes and confusion McPhail and have misunderstanding. done already in Molecules 2018, 23, x 1901 FOR PEER REVIEW 3 of 46 an independent publication [16,17]. However, there has been no review article featuring structural revisionsHence, reviewing of ellagitannins, structural which revisions is the istopic worthwhile of this article. as Amagata and McPhail have done already in an independent publication [16,17]. However, there has been no review article featuring structural 2.revisions Notice of ellagitannins, which is the topic of this article. 2. NoticeIn this review article, the following contrivance is used in order to improve intelligibility. For the revised compounds, all of the previously reported structures are exhibited inside a square frame with Inangular this review corners article, (for example, the following Figure contrivance 2). In the frame, is used the in orderwords to “1st improve”, “2nd intelligibility.”, “3rd”, and “ Forlatest the” indicaterevised compounds,the transition all of ofthe the structure. previously As reporteda guide, the structures reported are year exhibited and the inside representative a square frameof the withreport angular are appended corners (forin a example,parenthesis. Figure Arrows 2). In with the frame, “revision” the words also show “1st”, the “2nd transition.”, “3rd”, andThe “ flamelatest” appearsindicate first the transitionin each description of the structure. for revised As a guide,ellagitannins, the reported which yearmight and help the in representative understanding of the overallreport aretransition. appended Regarding in a parenthesis. the initial Arrowsstructural with de “revision”termination, also the show processes the transition. to find the The errors flame in theappears structure, first inand each the description methods for for the revised revision ellagitannins, of the structure, which mightglancing help at infigures understanding might not thebe enoughoverall transition.to understand; Regarding so, reading the initial the text structural while determination,referring to the the figures processes is recommended. to find the errors Degraded in the compoundsstructure, and that the arose methods in the for processes the revision of ofthe the struct structure,ural determination glancing at figures are also might illustrated not be enough similarly to inunderstand; square frames so, reading with angular the text corners while referring (for example, to the Figure figures 10). is recommended. Frames with round Degraded corners compounds are used tothat indicate arose in the the simplified processes expression
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