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Unripe Apple Polyphenol Mixture; Process for Production of Unripe

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Unripe Apple Polyphenol Mixture; Process for Production of Unripe Europäisches Patentamt *EP000657169B1* (19) European Patent Office Office européen des brevets (11) EP 0 657 169 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.7: A61K 35/78 of the grant of the patent: 25.09.2002 Bulletin 2002/39 (21) Application number: 94401669.0 (22) Date of filing: 20.07.1994 (54) Unripe apple polyphenol mixture; process for production of unripe Rosaceae fruit polyphenol mixtures Polyphenolmischung aus unreifen Äpfeln; Verfahren zur Herstellung von Polyphenolmischungen aus unreifen Rosaceae Früchten Mixture de polyphénols de pommes pas mûres; procédé pour la préparation de mixtures de polyphénols de fruits pas mûrs de la famille Rosaceae (84) Designated Contracting States: • Yanagida, Akio, c/o Nikka Whisky Dis. Co., Ltd. AT BE DE FR GB IT Masuo, Kashiwa-city, Chiba-pref. (JP) (30) Priority: 06.12.1993 JP 30563293 (74) Representative: Peuscet, Jacques et al 22.02.1994 JP 2443594 SCP Cabinet Peuscet et Autres, 78, avenue Raymond Poincaré (43) Date of publication of application: 75116 Paris (FR) 14.06.1995 Bulletin 1995/24 (56) References cited: (73) Proprietor: THE NIKKA WHISKY DISTILLING CO., WO-A-88/09178 DE-A- 2 549 688 LTD. DE-A- 2 746 950 DE-A- 3 209 419 Tokyo 107 (JP) • KRESANEK J.: ’Unsere Heilpflanzen’, 1982, (72) Inventors: VERLAG DAUSIEN * page 78 * • Tanabe, Masayuki, • TEUSCHER E.: ’Pharmazeutische Biologie, 3. c/o Nikka Whisky Dis. Co., Ltd. Auflage’, 1983, VIEWEG * page 246 * Masuo, Kashiwa-city, Chiba-pref. (JP) • STEINEGGER E., HCNSEL R.: ’Lehrbuch der • Kanda, Tomomasa, Pharmakognosie u. Phytopharmazie, 4. c/o Nikka Whisky Dis. Co., Ltd. Auflage’, SPRINGER VERLAG * page 397, 580 * Masuo, Kashiwa-city, Chiba-pref. (JP) Note: Within nine months from the publication of the mention of the grant of the European patent, any person may give notice to the European Patent Office of opposition to the European patent granted. Notice of opposition shall be filed in a written reasoned statement. It shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 0 657 169 B1 Printed by Jouve, 75001 PARIS (FR) EP 0 657 169 B1 Description Background of the Invention and The Related Art 5 [0001] The present invention relates to a mixture consisting essentially of polyphenols from unripe apples and a process for producing a mixture of unripe Rosaceae fruit polyphenols. [0002] In growing the trees of Rosaceae which bear edible fruits such as apple, pear, peach and the like, "thinning- out" of superfluous fruits is generally carried out in the period of mid May to mid July. In this thinning-out, unripe fruits in the form of bunch or cluster are removed with some of them left unremoved. Consequently, a large amount of unripe 10 fruits are disposed by the thinning-out, without being utilized. These unripe fruits are very bitter as compared with ripe fruits, and the sectional surface of each unripe fruit turns brown easily. This fact suggests the presence of a large amount of polyphenol compounds in unripe fruits. [0003] It is known that polyphenol compounds are generally present in the plant kingdom as a secondary metabolite of plant in numerous kinds and in a large amount. Some of these polyphenol compounds have drawn attention for their 15 diversified physiological activities, from the past in the field of pharmacology and in recent years in the field of food chemistry. [0004] Among them, tea polyphenol (catechins) is drawing particular attention and concentrated researches are under way thereon. This tea polyphenol is being recognized to have very wide physiological activities such as antibac- terial activity, antiviral activity, antioxidative activity, antimutagenic activity, anticancerous activity, platelet coagulation- 20 inhibiting activity, blood pressure increase-inhibiting activity, blood sugar increase-inhibiting activity, blood cholesterol- reducing activity, anticariogenic activity, antiallergic activity, intestinal flora-improving activity, deodoring activity and the like [Japanese Patent Application Kokai (Laid-Open) Nos. 214183/1988, 6499/1990, 178320/1992, etc.]. [0005] Thus, it is known that, for example, the polyphenol extracted from tea has wide physiological activities. 25 Summary of the Invention [0006] An object of the present invention is to provide a fruit polyphenol mixture having various physiological activities, which is different from the polyphenol extracted from tea. [0007] Another object of the present invention is to provide a process for producing a mixture of Rosaceae fruit 30 polyphenols, notably the above fruit polyphenol mixture effectively and economically. [0008] According to the present invention, there is provided a mixture consisting essentially of polyphenols obtainable by pressing or extraction of unripe apples to form a juice or extract, treating the juice or extract with an adsorbent which selectively adsorbs the polyphenols contained in the juice or extract, eluting the polyphenols from the adsorbent with an alcohol, and recovering the mixture of polyphenols from the elute; the mixture of polyphenols consisting essentially 35 of caffeic acid, caffeic acid esters, p-coumaric acid, p-coumaric acid esters, phloretin, phloretin glycosides, phloridzin, quercetin, guercetin glycosides, catechin, epicatechin, and condensed tannins, condensed tannins being regular pol- ymers of n catechin monomers, n having a valus ranging between 7 and 10. [0009] According to the present invention, there is further provided a process for producing a mixture of unripe Ro- saceae fruit polyphenols, which comprises subjecting unripe fruits of Rosaceae, particularly unripe apples, unripe pears 40 or unripe peaches to pressing and/or extraction and then purifying the resulting juice or extract to obtain a polyphenol fraction. [0010] The mixture according to the present invention is an antioxidant. [0011] The mixture according to the present invention is an hypotensive agent and an antimutagenic agent. [0012] According to the present invention, the mixture is further an antiallergic agent having a hyaluronidase-inhibiting 45 activity. [0013] According to the present invention, the mixture is further an anticariogenic agent. Brief Description of the Drawings 50 [0014] Fig. 1 is graphs showing the HPLC chromatogram and the comparison of UV spectle of each peaks of unripe apple polyphenol. [0015] Fig. 2 is graphs each showing the relation between the amount of peroxylipid formed (the absorbance at 500 nm) and the addition concentration of extract from unripe or ripe apple "Fuji", in one week after said extract was added to a reaction system. 55 [0016] Fig. 3 is graphs each showing the relation between the amount of peroxylipid formed (the absorbance at 500 nm) and the addition concentration of polyphenol fraction of unripe or ripe apple "Fuji", in one week after said fraction was added to a reaction system. [0017] Fig. 4 is graphs showing the amounts of peroxy-lipids formed (the absorbances at 500 nm) in one week after 2 EP 0 657 169 B1 various polyphenol compounds were added to respective reaction systems. [0018] Fig. 5 is graphs each showing the relation between the amount of peroxylipid formed (the absorbance at 500 nm) and the addition concentration of polyphenol fraction of each unripe apple, in one week after said fraction was added to a reaction system. 5 [0019] Fig. 6 is graphs each showing the relation between the amount of peroxylipid formed (the absorbance at 500 nm) and the addition concentration of polyphenol fraction of each unripe Rosaceae fruit, in one week after said fraction was added to a reaction system. [0020] Fig. 7 is graphs each showing the angiotensin I converting enzyme (hereinafter referred to as ACE)-inhibiting activity of polyphenol fraction of unripe or ripe apple "Fuji". 10 [0021] Fig. 8 is graphs showing the ACE-inhibiting activities of various polyphenol fractions B when each polyphenol fraction B was added to a reaction system in various amounts. [0022] Fig. 9 is graphs showing the ACE-inhibiting activities of various polyphenol compounds when each polyphenol compound was added to a reaction system in various amounts. [0023] Fig. 10 is a graph showing the absorption spectrum of an isolated polyphenol fraction, measured by a spec- 15 trophotometer. [0024] Fig. 11 is graphs showing the results of measurement by GPC, of molecular weights of condensed tannin. [0025] Fig. 12 is the structural formula of the ACE-inhibiting substance contained in the unripe apple polyphenol mixture of the present invention. [0026] Fig. 13 is graphs showing the antimutagenic activities of various polyphenols to Trp-P-2. 20 [0027] Fig. 14 is graphs showing the antimutagenic activities of apple tannin and epigallocatechin gallate to benzo-[a] pyrene. [0028] Fig. 15 is graphs showing the hyaluronidase-inhibiting activities of various Rosaceae fruit extracts. [0029] Fig. 16 is graphs showing the hyaluronidase-inhibiting activities of an antiallergic agent (sodium cromoglicate) and apple tannin. 25 [0030] Fig. 17 is graphs showing the relations between the amount of insoluble glucan formed and the amount of Rosaceae fruit polyphenol fraction added, when various Rosaceae fruit polyphenol fractions were added to respective reaction systems. [0031] Fig. 18 is graphs showing the relations between the amount of insoluble glucan formed and the amount of polyphenol compound added, when various polyphenol compounds were added to respective reaction systems. 30 Detailed Description of the Invention [0032] The fruit polyphenol mixture according to the present invention is a polyphenol mixture obtained by subjecting unripe apples to pressing or extraction and then purifying the resulting juice or extract. The purification is conducted 35 by treating the juice or extract with an adsorbent, and the fraction of the juice or extract adsorbed by the adsorbent (this fraction is hereinafter referred to as "adsorbed fraction") contains a fruit polyphenol. The adsorbed fraction is eluted with an anhydrous alcohol (e.g. ethanol) to obtain a purified polyphenol fraction. [0033] This polyphenol fraction is then concentrated, whereby a liquid polyphenol product can be obtained.
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