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(12) Patent Application Publication (10) Pub. No.: US 2011/0268825 A1 Burgos Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2011/0268825 A1 Burgos Et Al US 20110268825A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0268825 A1 Burgos et al. (43) Pub. Date: Nov. 3, 2011 (54) COMPOSITIONS THAT INCLUDE A6IP3L/04 (2006.01) ANTHOCYANDINS AND METHODS OF USE A6IP3L/00 (2006.01) A6IR 36/45 2006.O1 (76) Inventors: Rafael Burgos, Valdivia (CL); Juan A6IP 29/00 308: Hancke, Region Metropolitana A6IP3/00 (2006.01) (CL): Evelyn Jara, Valdivia (CL): A6IP3/04 (2006.01) Maria Hidalgo, Valdivia (CL) A6IP3/10 (2006.01) A63L/352 2006.O1 (21) Appl. No.: 13/076,117 A6IP35/00 308: (22) Filed: Mar. 30, 2011 A6IP3L/2 (2006.01) (52) U.S. Cl. .......................... 424/732; 424/777: 514/456 Related U.S. Application Data (63) Continuation of application No. PCT/IB2010/002698, (57) ABSTRACT filed on Oct. 21, 2010. The compositions described herein and featured in the (60)60) Provisional app lication1cauon No. 91/453.833,61/253.835, filedIlled on Oct9c. presentcombinations invention rich include in delphinidins, those that compriseincluding anthocyanidin delphinidins 21, 2009, provisional application No. 61/279.541, Such as the ones found in berries. The compositions can filed on Oct. 22, 2009. optionally include either compositions that comprise O O andrographolides, such as the ones found in a plant of the Publication Classification genus Andrographis, or compositions that comprise combi (51) Int. Cl. nations of myrtillin, quercetin, or caffeoylquinic derivatives A6 IK 36/18 (2006.01) and proanthocyanidins. Such as the ones found in the herba of A6IP37/00 (2006.01) a plant of the genus Vaccinium. Patent Application Publication Nov. 3, 2011 Sheet 1 of 5 US 2011/0268825 A1 2.2 2.0 1.8 1.6 1.4 1.2 10 O.8 O.6 0.4 may 0.2 Delphinidin 50 uM FIG. 1 Patent Application Publication Nov. 3, 2011 Sheet 2 of 5 US 2011/0268825 A1 Delphinidin 50 uM FIG. 2A a Delphinidin 50 uM BTP-2 10 M FIG. 2B Patent Application Publication Nov. 3, 2011 Sheet 3 of 5 US 2011/0268825 A1 3.0 2.5 8 so Vehicle S. 20 U73122 50 uM O ? 15 8% W K. U73122 100 M 1.O 100 150 200 250 300 350 Time (sec) FIG. 3 Patent Application Publication Nov. 3, 2011 Sheet 4 of 5 US 2011/0268825 A1 Anthoc 1.75 ug/ml COX-2 f-Actin FIG. 4A Control Anthoc 1.75 g/ml COX-2 B-Actin 1.5 5 S-q 1.0 FIG. 4B c t 8 0.5 O.O Control Anthoc 1.75 g/ml Anthoc 1.75 g/ml + Androg 50 puM fMLP (100 nM) H -H - COX-2 B-Actin FIG. 4C Patent Application Publication Nov. 3, 2011 Sheet 5 of 5 US 2011/0268825 A1 1500 1000 300 2OO 100 Control 7 mg/kg 70 mg/kg FIG. 6 US 2011/0268825 A1 Nov. 3, 2011 COMPOSITIONS THAT INCLUDE phis). In embodiments of the invention, the delphinidin-con ANTHOCYANDINS AND METHODS OF USE taining (e.g., delphinidin-rich) compositions can include spe cific compounds such as one or more of myrtillin, cyanidin, CROSS REFERENCE TO RELATED quercetin, a caffeoylquinic derivative, a proanthocyanidin APPLICATIONS and/or proanthocyanin (e.g., as found in the herba (e.g., 0001. This application claims the benefit of the filing date leaves) of a plant of the genus Vaccinium). of U.S. Provisional Patent Application No. 61/253,835, filed 0007 More specifically, the invention features composi Oct. 21, 2009, and U.S. Provisional Patent Application No. tions that consist of or that include a plurality of anthocyanins 61/279.541, filed Oct. 22, 2009. For the purpose of any U.S. and/or anthocyanidins in which (a) at least or about 35% of application, the entire content of these earlier filed applica the composition, by weight, is an anthocyanin or anthocya tions is hereby incorporated by reference in the present appli nidin and (b) at least or about 15% of the anthocyanins and/or cation. anthocyanidins, by weight, are Sugar-free or Sugar-containing delphinidins. These compositions and any of the composi TECHNICAL FIELD tions of the invention can be non-toxic, and all are non naturally occurring (i.e., none are identical to a product of 0002 This invention relates to various compositions that nature). As noted, the compositions can include Sugar-con generally include certain amounts and types of anthocyani taining delphinidin, Such as a delphinidin glucoside (e.g., dins and/or their glycoside counterparts. These compositions delphinidin-3-O-Sambubioside-5-O-glucoside). The amount can be made and used alone or made and used in combination of the delphinidin can vary according to the parameters set out with other compositions, for example, those containing an herein. For example, at least or about 15% of the anthocyanins andrographolide. The compositions can be formulated as and/or anthocyanidins, by weight (e.g., at least or about 15%, pharmaceutical preparations or incorporated into foods such 20%, 25%, 30%, 35%, 40%, 45%, or 50%), can be adelphini as drinks and cereal bars. Their administration or consump din such as delphinidin-3-O-sambubioside-5-O-glucoside. tion helps maintain immune function, stimulates the immune Expressed differently, at least or about 5% of the composition system, reduces inflammation, and protects against other as a whole, by weight (e.g., at least or about 5%, 10%, 15%, unwanted conditions (e.g., metabolic syndrome). 20%, or more), can be a delphinidin such as delphinidin-3- O-sambubioside-5-O-glucoside. BACKGROUND OF THE INVENTION 0008. In the compositions of the invention, one or more, 0003 Anthocyanidins and anthocyanins (anthocyanidins including all, of the anthocyanins or anthocyanidins can con including Sugar groups) are a large family of naturally occur form to the following formula: ring pigments. The color of most fruits, flowers and berries is determined by their content of anthocyanidins and anthocya 1S. (I) 0004. Others have suggested uses for anthocyanidins. For example, it has been Suggested that anthocyanidins and anthocyanidin derivates can exhibit antiviral effects in infected cells and antineoplastic effects in neoplastic cells (see PCT/NO97/00100 (WO 97/41137)). Anthocyanin-rich extracts are also disclosed for the treatment of a disordered metabolism syndrome (see U.S. Application Publication No. 2009/0176718). SUMMARY 0005. The present invention is based, in part, on our stud ies of compositions that include an anthocyanin oranthocya wherein each of R. R. R. R. R. R. and R, are, indepen nidin preparation that is rich in delphinidin(s). While there dently, —H. —OH, or OCH (see Table 1, below). has been significant interest in anthocyanins and in the anti 0009 While specific formulations are discussed further oxidant properties of berry extracts, this is, to our knowledge, below, and while formulation methods, including those for the first description of compositions that include not only a other anthocyanidin-containing preparations are known in certain amount of anthocyanins and/or anthocyanidins, but the pharmaceutical and food industry arts, we note here that also a certain amount and/or a certain type of a delphinidin. the compositions of the invention can be formulated for oral The various compositions and methods of the invention have consumption (e.g., as an ingredient of a food product) or oral other distinguishing characteristics as well. administration (e.g., as a tablet, pill, capsule, caplet, and the 0006. In a first aspect, the compositions of the present like), or they can be formulated for administration by a invention include one or more anthocyanidins and/or agly parenteral route. colic anthocyanins that have been enriched for one or more 0010. The compositions of the invention (as described delphinidins. For example, either the amount or type of the above and further below) can also include an andrographolide anthocyanidins or anthocyanins or the amount or type of the and can be enriched for andrographolides (e.g., the androgra delphinidins (or both) may differ from (e.g., exceed) that pholide can constitute, by weight, at least or about 10% (e.g., found in a naturally occurring composition Such as a berry or at least or about 10%, 15%, 20%, 25%, 30% or more) of the other plant part or product. In embodiments of the invention, composition. The andrographolide can be an androgra the delphinidin-containing (e.g., delphinidin-rich) composi pholide, a deoxy-andrographolide, a neoandrographolide, or tions can include additional specific compounds such as an a mixture thereof, and it may be contained within an extract of adrographolide (e.g., from a plant of the genus Androgra a plant of the genus Andrographis (e.g., Andrographus pan US 2011/0268825 A1 Nov. 3, 2011 iculata). The amount of the andrographolide may also be mg of soya lecithin, and 700 mg oenothera biennis oil; 400 expressed relative the amount of the anthocyanins and/or mg of microcrystalline cellulose, 95 mg of lactose, and 10 mg anthocyanidins, and the ratio of anthocyanin and/or antho of silicon dioxide; or 400 mg microcrystalline cellulose, 15 cyanidin to andrographolide can be about 1.0:0.1 to about mg povidone, and 10 mg Sodium carboxymethylcellulose. 1.0:10 (w:w) (e.g. 1.0:0.5 to about 1.0:2.5 (w:w). 0018. In another specific embodiment, the pharmaceutical 0.011 Compositions that include (e.g., compositions compositions can include (a) a first composition comprising a enriched for) myrtillin, quercetin, and/or cyanidin can include at least or about 15% (e.g., at least or about 15%, 20%, carrier, (b) about 100 mg to 400 mg of a second composition 25%, 30%, or more) myrtillin, quercetin, and/or cyanidin.
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