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Studies on the Highly Oxidized Ellagitannins in Medicinal Plants

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Studies on the Highly Oxidized Ellagitannins in Medicinal Plants Studies on the Highly Oxidized Ellagitannins in Medicinal Plants HIDEYUKI ITO 1999 Studies on the Highly Oxidized Ellagitannins in Medicinal Plants HIDEYUKI ITO 1999 Studies on the Highly Oxidized Ellagitannins in Medicinal Plants Contents Introduction Chapter I. Geraniin-Related Ellagitannins 5 1-1. Ellagitannins from Phyllanthus flexuosus 6 1- 1-1. Extraction and Isolation 1-1-2. Structures of Phyllanthusiins A - E 1-2. Ellagitannins from Geranium thunbergii 20 1-2-1. Extraction and Isolation 1-2-2. Structures of Geraniinic acids 8 and C, and Phyllanthusiin F 1-3. Ellagitannins from Acalypha hispida 28 1-2-1. Extraction and Isolation 1-2-2. Structures of Acalyphidins MI, M2 and DI 1-4. Geraniin-Related Ellagitannin monomers in Euphorbiaceae and Their Chemotaxonomical Significance 39 Chapter II. Ellagitannins Having a Gluconic Acid Core 44 II-I. Ellagitannins from Shepherdia argentea 44 11-1-1. Extraction and Isolation II -1-2. Structures of Shephagenins A and 8 11-2. Ellagitannins from Elaeagnus umbellata 49 11-2-1. Extraction and Isolation 11-2-2. Structures of Elaeagnatins A-G -1- Introduction 11-3 . Taxonomical Significance of Ellagitannins Having A Gluconic Acid Core 61 A large group of polyphenolic compounds, "Tannins", are widely distributed in vegetable 11-4. Biogenesis of C-glucosidic Ellagitannin Dimers 62 kingdom, which are often encountered in our lives, being contained in tea, red wine, fruits, beverages and various medical plants. They are characterized as polyphenols possessing an Chapter III. Biological Activities of Highly Oxidized Ellagitannins astringent taste and ability to fonn colored solutions and precipitate with iron and other metals, and Related Polyphenols 66 in addition to binding properties with proteins such as albumin, gelatin and collagen as well as III- I. Anti-Tumor Activity of Tannins and Related Polyphenols 66 alkaloids. The definition of tannins is proposed to be natural polyphenols with the aoove chemi­ III- I - I. In vitro assay; Inhibitory Effect on Epstein-Barr Virus 1 cal properties of molecular weights up to 500. ) Early Antigen Activation Early studies in tannin chemistry focused mostly on the characterization of components of 111 - 1-2. In vivo assay; Inhibitory Effect in Two-Stage Carcinogenesis Assay plant extracts used in the leather industry.2) On the other hand, numerous tannin-rich plants have been used as folk medicines (hemostatics, antidiarrheic, diuretic, antiseptic, etc) and as Antibacterial Activity of Tannins and Related Polyphenols 111 -2. 2 consumed food and beverages in Asia, Europe, North America and Africa. , 3) However, the against Helicobacter pylori 71 chemistry of tannins in medical plants had been little investigated until 1970, because of diffi­ culty in the isolation of intractable, unstable, hardly separable tannins with closely related struc- Concluding Remarks 76 tures .• Nevertheless, the number of reports dealing with the isolation and structural elucidation of Experimental 79 this class of natural polyphenols from medicinal plants and foods has increased markedly during Acknow ledgemen ts 94 the last two decades. The remarkable progress in the chemistry of tannins has been mostly based on developments of modern analytical and isolation techniques and various spectroscopies References 95 including high-field NMR, CD, and FAB-MS.4) List of Compounds 99 Generally, tannins are traditionally classified into two large groups, hydrolyzable tannins and S condensed tannins. ) These names are based on their hydrolysis and condensation occurring in the presence of acid or enzyme. The former with structural variation is further sub-divided into gallotannins, ellagitannins and their oxidized metabolites (dehydroellagitannins), C-glucosidic 7 tannins,6) and complex tannins ), the last among which are composed of both hydrolyzable tan- -1- -ii - nin and flavan units. Among those various types of hydrolyzable tannins characterized to date, On the other hand, although most of these ellagitannins have glucose core as a sugar unit in the ellagitannins have been attracted a considerable attentions because of their vast structural diver­ molecule, those having a gluconic acid residue as a polyalcohol have rarely been encountered in 8 sity and biological activities specific to structures ). Various biological activities including an­ nature. These ellagitannins have been hitherto found only in four plants IHippopha e rhamnoides l2 ) 3 tioxidant, antiviral and antitumor activities were noticed and reported for different types of (Elaeagnaceae), Lagerstroemia speciosa, 13) L. subcostatal ) (Lythraceae) and Punica grana­ 9 l4 ellagitanni ns. ) tum ) (Punicaceae)I, but their biological activity are not known at all. Among these plant fami ­ Among these ellagitannins having various biological acti vities, the oral administration of lies, the author has focused on the elaeagnaceous plants which have little been studied for tannin geraniin and the geraniin-containing extract from Geranium thunbergii to rats was found to constituents. Consequently, nine new ellagitannins with highly oxidized structures have been reduce the lipid peroxide concentration in serum and liver, which was raised by feeding the isolated from Shepherdia argentea and Elaeagnus umbel/ata, and their structures have been animals with peroxidized corn oil. 10) The levels of serum cholesterol, GOT, and GPT were also elucidated on the basis of spectral and chemical evidence. Five among them were ellagitannins lowered. Ellagic acid, which exists in nature as a component unit of ellagitannins, was also based on the gluconic acid core, and the other four were C-glucosidic ellagitannin dimers which found to show a potent anti-carcinogenic activity. I I) are regarded as the metabolites biogenetically produced by an intermolecular oxidative cou­ Geraniin is characterized by having a hydrated dehydrohexahydroxydiphenoyl (DHHDP) group pI i ng between monomers. in the molecule, and is classified as dehydoellagitannins. The DHHDP group might originate This dissertation deals with the investigation on the isolation and structure elucidation of new biogenetically from a hexahydroxydiphenoyl (HHDP) group that is a common constituent of 17 ellagitannins with highly oxidized structures from the five plant species in three families ellagitannins. The reactive DHHDP group might be further metabolized into various related (Euphorbiaceae, Geraniaceae and Elaeagnaceae). In addition, the biological activities such as acyl groups to lead a large number of mcxlified dehydroellagitannins that show various biologi­ in vitro and in vivo anti -tumor promoting effects and antibacterial activity against Helicobacter cal activities. Chebulagic acid is one of the typical example of modified dehydroellagitannin pylori have also been investigated for the tannins and related polyphenols obtained from the probably derived from geraniin, and it was reported to exibit an anti-tumor activity and a potent above five plant species. inhibitory effect against DNA-topoisomerase II. Geraniin and related compounds are consid­ ered to be metabolized in an animal, and then those metabolites may be activators or indirectly act as mediators. In order to secure positive evidence of a contribution of these ellagitannins to various biological activities, accumulation of much more new findings on structure-activity relationships of this class of tannins would be needed. From this viewpoint, the author tried to search for new tannins focusing on highly oxidized ellagitannins in nature and to estimate their biological acti vity. The plants investigated in this study were (l) Phyllanthus flexuosus, (2) Acalypha hispida belonging to Euphorbiaceae and (3) Geranium thunbergii (Geraniaceae). -2- -3- Chapter I. Geraniin-Related Ellagitannins Geraniin (1), a yellow crystalline dehydroellagitannin, was originally isolated from an official anti-diarrheic in Japan, Geranium thunbergii (Geraniaceae) 15) and from Acer species (Aceraceae).16) Its wide distribution in Euphorbiaceae as well as Geraniaceae was reported in 17 1982. ) Recently, its structure including absol ute configuration was unambiguously substanti­ ated by X-ray analysis, 18) which was the first example of chrystallographic analysis of free ellagitannin. A large number of hydrolyzable tannins related with geraniin has revealed its wider distribution in species of Cercidiphyllaceae, 16) Elaeocarpaceae, 19) Melastomataceae,20) Rosaceae,21) Coriariaceae,22) Simaroubaceae, 16) and Betulaceae.23 ) The dehydroellagitannins and their metabolites have been found in the genera Euphorbia, Mallotus, and Macaranga. Among them, chebulagic acid (2) is often found coexisting with a major tannin, geraniin, in those genera, which could be producible by benzylic acid rearrange­ ment-like cleavage of cyclohexenetrione ring in the DHHDP group.8) The modified DHHDP group and other analogues would biogenetically originate from chebuloyl group or its equiva- lent. Geraniin is thus regarded as a key compound in the biogenesis of those modified I dehydroellagitannins based on the C4-glucose core. In order to survey new geraniin-related ellagitannins in nature, geraniin-rich plants I Phyllanthus HO OHHO OH H0-O----O-0H co co OH H g / O-C-o-0H 731 0 -OH o 0 \ , co co co\ coI O~OH~ If O~QHO -- - ~OH HO~~~OHo OH 0 OH a b -4- -5- flexuosus, Acalypha hispida (Euphorbiaceae) and Geranium thunbergii (Geraniaceae) I have been 1-1-1. Extraction and Isolation investigated and several new tannins with highly oxidized structures have been isolated.
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