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Ellagitannins As Active Constituents of Medicinal Plants

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Ellagitannins As Active Constituents of Medicinal Plants Review 117 Ellagitannins as Active Constituents of Medicinal Plants Takuo Okuda'2, Takashi Yoshida', and Tsutomu Hatano' Faculty of Pharmaceutical Sciences, Okayama University, Tsushima, Okayama 700, Japan 2Addressfor correspondence Received: September 17, 1988 regarded as intractable mixtures having unfavorable biological Abstract activities, regardless of the structural differences among each tannin, the recent isolation and structural determination of a Isolation and structure determination, ac- number of ellagitannins, including their oligomers among companied by measurement of various biological activities which agrimonlin was the first one (2, 3), aided by the progress of each isolated tannin, particularly of ellagitannins, have in analysis methods (4) and in screening procedures for biolog- brought about a marked change in the concept of tannins as ical activities of each tannin thus brought about a marked active constituents of medicinal plants. Their biological ac- change in the concept of tannins. Ellagic acid, which has re- tivities should now be discussed on the basis of the struc- cently been a topic of interest because of its anti-carcinogenic tural differences among each tannin, in a way similar to that activity (5), should be considered as a compound derived from of the other types of natural organic compounds. The anti- ellagitannins, since ellagic acid is mostly produced by a hy- tumor activity exclusively exhibited by several oligomeric el- drolysis of ellagitannins taking place during their extraction lagitannins, and their anti-HIV activities are examples of and the concentration of the extracts from plants, and is rarely such biological activities, The inhibitory activity against found in living plants (6). The discovery of marked anti-tumor lipid peroxidation, which is different in the strength among (7) and anti-HIV activities (8) specifically exhibited by several of tannins of various structures, is exhibited in general more the oligomeric hydrolyzable tannins among a number of tan- strongly by ellagitannins than by the other types of tannins nins screened, further demonstrated the necessity for a change of similar structures. The radical-scavenging activities of of the old concept of tannins. tannins as the mechanism of their inhibition, which is re- garded to participate in several biological activities of tan- Biogenesis of Ellagitannins nins, have been supported by the ESR spectral measure- ments. Other biological activities, i.e., inhibition of The HHDP group in ellagitannins has been mutagenicity of carcinogens, inhibition of tumor promotion, presumed biogenetically to be produced by the C-C bond for- etc., have been found for tannins including ellagitannins. mation between two galloyl groups (9). Recent investigation of the seasonal changes in the structures of hydrolyzable tannins in Liquidainbarforinosana, revealed the formation of an I-IHDP group in several tannins, in place of two galloyl groups with the same locations on the glucopyranose ring in the tannin Introduction molecule found in the same plant in earlier seasons (10). Liquidambin, a compound which has a partly hydrated al- Ellagitannins belong to the group of hydrolyz- dehyde group and is regarded as an intermediate product in able tannins which, along with condensed tannins, comprisethe biosynthesis of C-glucosidic ellagitannins, has also been isolated (11). An example of a series of biosyntheses of several one of the two large groups of tannins, and have the hexahy- This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. droxydiphenoyl (HHDP) group, or a similar group derivabletypes of ellagitannins, supported by these findings, can be de- from the HHDP group, in their molecules, The number of el- picted as shown in Scheme 1. lagitannins hitherto isolated is by far larger than that of gal- lotannins, which constitute another group belonging to the The distribution of ellagitannins in plant hydrolyzable tannins, and are often present as complex mix- families which have been thus biosynthesized, is therefore fun- tures. Ellagitannins are generally different from the other typesdamentally the same as that of gallotannins (15). of tannins in that each of them can be isolated as a compara- tively stable compound, as exemplified by geraniin which is a Tatmins Related to Ellagitannins crystalline tannin (1), and can be handled as a single compound of defined structure. This property of ellagitannins made it pos- There are a number of monomeric ellagitan- sible to measure the biological activities of each isolated tanninnins, in which the HHDP group (a) has been further of determined chemical structure, like those of each compoundmetabolized to the other aromatic groups (b)—(f) by structural belonging to the alkaloids, terpenoids, and steroids, etc., al-modifications such as oxidation, reduction, ring cleavage, and though it is also true that there are some properties common toC-O(C) oxidative coupling. These tannins are often regarded as most of tannins. Although tannins, in the past, were generally belonging to the ellagitannin group on the basis of their pre- 118 PlantaMedica 55(1989) Takuo Okuda et at OH OH HOL o OH HO HO - H H OH 0 "H HO HO HO__HO HO OH OH HH pentagalloyLgLucose (12) pedunculagin (13) liquidambin (11) OH OH =HO5 OH HO 0 OH HO HOOH HO HO>H tellimagrandin 11 (13) casuarictin (13) casuarinin (13) dimers HO HO OH OH trimers HO,OH ,J—O 0 OH HO—('H o>IO HO HO OH OH Scheme 1 castaLagin (14) sumable biogenetic relationship with the tannins having thetannin having the dehydrohexahydroxydiphenoyl (DHHDP) HHDP group, although there are tannins such as geraniin (1)group is mixed with ascorbic acid in so)ution at room tempera- having two or more of these types of groups, and/or a galloylture (25). group in a molecule. Some ellagitannins also have the other This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. bonding in their molecules, as those referred to in groups (i)— (iii) Condensates with catechins: Most of this (iv). The representative ellagitannins having the groups (a)—(Otype of ellagitannins are composed of C-glucosidic ellagitannins are shown in Scheme 2. and catechins, and the C-C bond is formed between C-I of the former and C-6 or C-8 of the latter (26). (i) C-Glucosides: Ellagitannins of this type might be biogenetically produced by a phenol-aldehyde coupl- (iv) Oligomers: Oligomeric ellagitannins ing as illustrated in Scheme 1. They include tannins such asexemplified by agrimoniin (2, 3), oenothein B (dimer) (27), castalagin (14) having a flavogalloyl group, which is regardedrugosin G (trimer) (28), and nobotanin K (tetramer) (29), etc., as a condensate through the C-C coupling between an HHDPare regarded as products of biosyntheses in which a valoneoyl and a galloyl group. group, or a dehydrodigalloyl group is formed between two molecules of monomeric or oligomeric hydrolyzable tannins (ii) Condensates with ascorbic acid: As- (Scheme 4). corgeraniin was found in several species of Geranium, Acer, Elaeocarpus. Rhus, and Cercidiphyllum genera (24) (Scheme 3). This type of tannin is easily formed in a high yield when a Ellagitannins as Active Constituents of Medicinal Plants Planta Medica 55(1989) 119 O=c cO HO—-—OH O—)_OH HO HO OH OH HOH/'OH (a) hexahydroxydiphenoyl (b) dehydrohexahydroxydiphenoyl (HHDP) group (DHHOP) group pedunca(agin (13), Igeraniin (1), terchebln (16), casuarictin (13), etc.] isoterchebin (17), etc.] HOØOØ HOO[\OH HOHO OH OH (C) chebuloyl group (dl dehydrodigalloyl (DHDG) group [chebulagic acid (18), [agrimonic acid A (19), chebulinic acid (18)1 agrimonic acid B (19)] I I HO_(_OHO HO HO HO _-_\oH OH OH (e) vatoneoyt group (rugosins A, B, C (20), castavalonic acid (21), mediniltin A (22), etc.] OC HO OH CO HO-ç----O HO HO HO OH OH (f) gatlagyl group [punicalagin (23), punicalin (23)] Scheme 2 ascorgeraniin Scheme 3 Biological Activities of Ellagitannins 1. inhibitory effect on peroxidation of lipids and other co-existing substances, Biological activities of any isolable compound and radical-scavenging effect should be examined for each compound, however, there are This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited. some properties commonly found for ellagitannins. The prop- Inhibitory effects of tannins on the lipid perox- erty most easily noticed for many ellagitannins is their com-idation induced by ADP and ascorbic acid in rat liver mitochon- paratively mild property, which is weakly astringent on the ton-dna, and on that induced by ADP and NADPH in rat micro- gue, and is weakly irritating on the mucous membrane. The ex- somes, were strongly exhibited by some ellagitannins, such as tracts of medicinal plants containing ellagitannins, thereforepedunculagin and isoterchebin (30). This effect in condensed have been generally administered orally without marked un-tannins was somewhat lower, and that in the polyphenols of favorable responses. small molecules, except for (—)-epigallocatechin gallate (EGCG) which is the main component of so-called green tea tannin, was markedly lower. No positive correlation of the intensity of effect was observed between the inhibition of peroxidation in the ex- periment with ADP and ascorbic acid and the binding activity, as expressed by RA and RMB values of tannins (31). The exper- iments on the inhibition of peroxidation by the radical-chain reaction of methyl linoleate, initiated by ultraviolet irradiation of
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