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Increasing the Bioavailability of Flavan-3-Ols By

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Increasing the Bioavailability of Flavan-3-Ols By (19) TZZ _Z_T (11) EP 2 925 160 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A23L 29/00 (2016.01) A23K 20/10 (2016.01) 14.03.2018 Bulletin 2018/11 A61K 36/82 (2006.01) A61K 47/22 (2006.01) A23K 20/111 (2016.01) A23L 33/105 (2016.01) (2006.01) (2017.01) (21) Application number: 13798343.3 A61Q 19/00 A61K 8/97 A61K 31/352 (2006.01) A61K 31/353 (2006.01) A61K 8/49 (2006.01) (22) Date of filing: 29.11.2013 (86) International application number: PCT/EP2013/075140 (87) International publication number: WO 2014/083172 (05.06.2014 Gazette 2014/23) (54) INCREASING THE BIOAVAILABILITY OF FLAVAN-3-OLS BY POLYPHENOLS ERHÖHNUNG DER BIOVERFÜGBARKEIT VON FLAVAN-3-OLEN MIT POLYPHENOLEN AUGMENTATION DE LA BIODISPONIBILITÉ DE FLAVAN-3-OLS PAR DES POLYPHÉNOLS (84) Designated Contracting States: • WILLIAMSON, Gary AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Harrogate GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Yorkshire HG2 7AX (GB) PL PT RO RS SE SI SK SM TR • DIONISI, Fabiola CH-1066 Epalinges (CH) (30) Priority: 29.11.2012 EP 12194895 (74) Representative: Naudé, Dawn (43) Date of publication of application: Nestec S.A. 07.10.2015 Bulletin 2015/41 Centre de Recherche Nestlé Vers-chez-les-Blanc (73) Proprietor: Nestec S.A. Case Postale 44 1800 Vevey (CH) 1000 Lausanne 26 (CH) (72) Inventors: (56) References cited: • ACTIS GORETTA, Lucas EP-A1- 2 241 313 EP-A1- 2 263 481 CH-1000 Lausanne 26 (CH) WO-A1-02/34262 WO-A1-98/11789 • LEVEQUES, Antoine WO-A1-2005/004630 WO-A2-02/081651 CH-1066 Epalinges (CH) FR-A1- 2 899 768 FR-A1- 2 935 096 • DA SILVA PINTO, Marcia 4055 Basel (CH) • LAMBERT ET AL.: "effect of genistein on the • SABATIER, Magalie bioavailability and intestinal cancer CH-1000 Lausanne 26 (CH) chemopreventive activity of • REIN, Maarit (-)-epigallocatechin-3-gallate", CH-1093 La Conversion (CH) CARCINOGENESIS, vol. 29, no. 10, 2008, pages 2019-2024, XP002696050, Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 925 160 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 2 925 160 B1 2 Description effective absorption and a high bioavailability, or to at least to provide a useful alternative to what is known in [0001] The present invention relates generally to the the art. field of flavan-3-ols. In particular, the present invention [0007] The inventors were surprised to see that the provides a way to increase the bioavailability of flavan- 5 object of the present invention could be achieved by the 3-ols. Embodiments of the present invention relate to the subject matter of the independent claims. The dependent use of at least one polyphenolic compound in a compo- claims further develop the idea of the present invention. sition comprising at least one flavan-3-ol for increasing [0008] Accordingly, the present invention provides a the bioavailability of said flavan-3-ol, wherein the at least new approach for increasing the absorption of the flavan- one polyphenolic compound is selected from a group 10 3-ols, in particular their biologically active forms, parent consisting of flavonols, flavones, isoflavones, fla- compounds and/or metabolites. In accordance with the vanones, or combinations thereof. present invention this is achieved by co-administration [0002] Flavan-3-ols (including for example "cate- of these compounds with polyphenols, e.g., dietary chins") are present in several food sources such as co- polyphenols. coa, tea and apples. Several epidemiological, in vitro and 15 [0009] As used in this specification, the words "com- in vivo studies have associated the presence of these prises", "comprising", and similar words, are not to be compounds to health promoting effects such as antioxi- interpreted in an exclusive or exhaustive sense. In other dative and anti-inflammatory benefits (Aron, P.M., et al., words, they are intended to mean "including, but not lim- 2008, Molecular Nutrition & Food Research 52, 79-104). ited to". [0003] In general flavan-3-ols are subjected to several 20 [0010] The present inventors have conducted exten- phase II enzymes leading to conjugation with methyl sive in vitro experiments using a Caco-2 cell model and groups(catechol-O-methyltransferases - COMT), sulfate in vivo human bioavailability study that could show that groups (sulphotransferases - SULT) and glucuronyl the co-administration of flavan-3-ols with certain groups (uridine-5’-diphosphate glucuronosyl-transferas- polyphenols can increase the absorption of flavan-3-ols es - UDPGT). However, EGCG, the main flavan-3-ol25 and/or their metabolites. Without wishing to be bound by present in green tea, has been reported to be present in theory the inventors currently believe that the absorption human plasma mainly in its native form (Williamson et of flavan-3-ols is modulated by the presence of other al., 2011, Mol Nutr Food Res 55, 864-873). polyphenols through several mechanisms, for example [0004] The oral bioavailability of, e.g., the green tea through competition with metabolizing enzymes and/or flavan-3-ols is low, resulting in systemic flavan-3-ols lev- 30 through the inhibition of the efflux of flavan-3-ol and/or els in humans which are many fold lower than the effec- their metabolites from the cells. tive concentrations determined in in vitro systems (Lam- [0011] Consequently, the invention relates in part to a bert et al., 2007, Mol. Pharmaceutics 4, 819-825). Many non-therapeutic use of at least one polyphenolic com- approaches to increase bioavailability of flavan-3-ols pound in a composition comprising at least one flavan- from green tea have been reported in literature such as 35 3-ol for increasing the bioavailability of said flavan-3-ol, the administration of tea in combination with piperine, an wherein the at least one polyphenolic compound is se- alkaloid present in black pepper, and peracetylation of lected from a group consisting of flavonols, flavones, iso- EGCG. Another strategy to improve the absorption of flavones, flavanones, or combinations thereof. flavan-3-ols is the administration during a fasting state, [0012] In a further aspect, the invention relates to a however, it is important to notice that some human stud- 40 composition comprising at least one polyphenolic com- ies have shown that high doses of green tea preparations pound selected from a group consisting of flavonols, fla- can be potentially toxic (Chow et al., 2005, Clinical Can- vones, isoflavones, flavanones, or combinations thereof cer Research 11, 4627-4633; Bonkovsky, 2006, Ann In- and at least one flavan-3-ol for use in the treatment or tern Med 144, 68-71). prevention of disorders that can be treated or prevented [0005] Hence there is a need in the art for alternative 45 by flavan-3-ol administration. ways to improve the absorption of flavan-3-ols while avoiding overdosing of flavan-3-ols. Lambert et al.: Ef- Figure 1 shows the general formulas (A, B and C) of fects of genistein on the bioavailability and intestinal can- compounds that may form a mixture in accordance cer chemopreventative activity of (-)-epigallocatechin-3- with this invention. gallate, Carcinogenesis Vol. 29, no. 10, 2008, pages50 2019-2024 discloses the use of genistein to increase the Figure 2 shows the effect of co-incubation of different bioavailability of EGCG. Any reference to prior art docu- polyphenolic compounds with (-)-epicatechin on the ments in this specification is not to be considered an ad- apical efflux and basolateral transport of (-)-3’-O-me- mission that such prior art is widely known or forms part thyl-(-)-epicatechin. of the common general knowledge in the field. 55 [0006] The object of the present invention was it there- Figure 3 shows the dose-dependent effect of co-in- fore to improve the state of the art and in particular to cubation of genistein, nevadensin, hesperitin and provide a way to administer flavan-3-ols while ensuring chrysin with (-)-epicatechin on apical efflux and ba- 2 3 EP 2 925 160 B1 4 solateral transport of 3’-O-methyl-epicatechin (me- EGCG could be significantly enhanced if the flavan-3-ols tabolite). were co-administered with for example flavanones such as hesperitin 7-glucoside. Figure 4 shows the effect of co-incubation of different [0023] Hence, in accordance with the present inven- polyphenolic compounds with (-)-epicatechin on the 5 tion, the at least one polyphenolic compound may be on the apical efflux and basolateral transport of 3’- selected from a group consisting of flavonols, flavones, O-sulfate-epicatechin (metabolite). isoflavones, flavanones, or combinations thereof. [0024] This increase in absorption clearly demon- [0013] Table 1 presents the kinetic parameters such strates an improved bioavailability of flavan-3-ols if co- 10 as AUC (area under the curve) and C max (maximum con- administered with the tested polyphenols. centration) for EGCG (Epigallocatechin 3-gallate) from [0025] Through improving bioavailability of flavan-3- subjects in the control (GT= green tea extract) and treat- ols by co-administration with polyphenols the capacity ment groups (GT + HG= green tea extract + hesperitin for a beneficial change or a therapeutic effect of such a 7-glucoside). flavan-3-ol intervention is improved.
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