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United States Patent (19) 11 Patent Number: 5,977, 184 Birdsall Et Al

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United States Patent (19) 11 Patent Number: 5,977, 184 Birdsall Et Al USOO5977184A United States Patent (19) 11 Patent Number: 5,977, 184 Birdsall et al. (45) Date of Patent: Nov. 2, 1999 54) QUERCETIN CHALCONE AND METHODS Agrawal et al., “Synthesis of Proanthocyanidin; A New RELATED THERETO Leucocyanidin Trimer (4-8, C-O-C).” Current Science 48(15): 661–663, 1979. 75 Inventors: Timothy C Birdsall; Al F Czap, both of Sandpoint, Id. Ferreira et al., “Parameters regulating the C-and B-Cycliza tion of Chalcones,” Journal of the Chemical Society. Perkin 73 Assignee: Thorne Research, Inc., Sandpoint, Id. Transactions I: 1437–1446, 1975. Brandt et al., “Structure and Synthesis of Crombenin, a 21 Appl. No.: 08/528,682 Natural Spirocoumaranone,” Journal of the Chemical Soci 22 Filed: Sep. 15, 1995 ety. Chemical Communication (7): 392–393, 1972. Krishnamoorthy and Seshadri, “Preparation of Flavylium (51) Int. Cl." ..................................................... A61K 31/12 Salts from Dihydroflavonols,” Indian Journal of Chemistry 52 U.S. Cl. ............................................. 514/685; 568/334 6(8): 469-470, 1968. 58 Field of Search .............................. 568/334; 814/685 Clark-Lewis and Jemison, “Synthesis of C,2'-Diacetoxy-3, 56) References Cited 4,4',6'-Tetramethoxychalcone and 4,6,3',4'-Tetramethoxyi Soaurone, Aust. J. Chem. 21:815-816, 1968. PUBLICATIONS Tominaga, T., “Isomerization of Astilbin. I.,” Journal of the Kiehlmann, J. Nat Prod. 58 (3), 450–5, Mar. 1995. Pharmaceutical Society of Japan 80(9): 1202–1206, 1960. Chopin and Chadenson, “Synthesis of alphitonin, mesopin, and 2,4,6-trihydroxy-2-benzyl-3 coumaranone, Comptes Bhardwaj et al., “Constitution of Dinatin, Indian J. Chem. Rendus Hebdomadaires des Seances de l'Academie des 4: 173-176, 1966. Sciences, Serie C263(11): 729-731, 1966.(Plus CAAbstract Chandorkar et al., “Anthoxanthins: Part XII-Synthetic #66:10803). Approaches to 5-Hydroxylated Leucoanthocyanidins,” J. Aubry and Chopin, “Synthesis of racemeic dimethylpi Sci. Industr. Res. 21B: 24–27, 1962. nobanksin, trimethylaromadendrin and tetramethyltaxifo lin,” Bulletin de la Societe chimique de France 12: Anand et al., “Synthesis of Certain Partial Methyl Ethers of 4503–4510, 1971. (Plus CA Abstract #76:113021). Flavonols: Rhamnetin, 3-O-Methyl Quercetin, Birch et al., “The Structure of Alphitonin,” J Chem. Soc., pp. 3,3'-O-Dimethyl Quercetin, Ombuin, 3,7-O-Dimethyl 3593-3599, 1960. Gossypetin & Reso-oxyayanin-A,” J. Sci. Industr. Res. Clark-Lewis and Jemison, “Reinvestigation of the Supposed 21B: 322-329, 1962. Enediol Diacetate Derived, from Dihydroquercetin 5,7,3', 4'-Tetramethyl Ether: Novel Ring-Fission of Dihydroquer cetin 5, 7, 3', 4'-Tetramethyl Ether to C,2'-Diacetoxy-3,4, Primary Examiner Robert Gerstl 4,6'-Tetramethoxychalcone.” Tetrahedron Letters 35: Attorney, Agent, or Firm Seed and Berry LLP 4179-4182, 1966. 57 ABSTRACT Hergert et al., “The Methylation of Dihydroquercetin,” J. Org. Chem. 21: 304-310, 1956. Quercetin chalcone, an effective, Soluble and bioavailable Ravanel et al., Uncoupling Activities of Chalcones and bioflavonoid, is disclosed. Also disclosed are compositions Dihydrochalcones on Isolated Mitochondria from Potato containing quercetin chalcone in combination with an Tubers and Mung Bean Hypocotyls, Phytochemistry 21 (12): acceptable carrier and/or diluent, as well as methods for 2845-2850, 1982. administration thereof to warm-blooded animals. Such Brandt et al., “Metabolites from the Purple Heartwood of administration is beneficial in generally maintaining good Mimosoideae. Part 3. Acacia crombei C.T. White: Structure health of the animal and, more specifically, for the treatment and Partial Synthesis of Crombenin, A Natural Spiropelt of allergies. ogynoid,” Journal O the Chemical Society. Perkin Transac tions I: 1879-1883, 1981. 7 Claims, No Drawings 5,977, 184 1 QUERCETIN CHALCONE AND METHODS RELATED THERETO TECHNICAL FIELD O The present invention relates to a quercetin derivative, quercetin chalcone, as well as compositions and methods for preparation and use thereof. O 1O Although chalcones generally have high Solubility and BACKGROUND OF THE INVENTION absorption under physiological conditions (e.g., hesperidin methyl chalcone, a representative class member, is absorbed Bioflavonoids are a group of naturally occurring com 15 to the extend of 60% from an oral dose), their activity is Significantly less than that of Similar bioflavonoids Such as pounds and are widely distributed among plants, including quercetin. This greater Solubility and absorption of chal most all citrus fruits, rose hipS and black currants. Such cones may be attributed to their increased Solubility through compounds are generally isolated from the rinds of oranges, Substituents Such as Sugar moieties present in Some chal tangerines, lemons, limes, kumquats and grapefruits by cones and absent in quercetin. The greater Solubility and commercial extraction methods. absorption of chalcones thus appears to be at the expense of biological activity. Bioflavonoids have been determined to be involved with Accordingly, there is a need in the art for a Soluble, homeostasis of the walls of Small blood vessels. In addition, bioavailable bioflavonoid that also possesses high bioactiv these compounds have been found to contribute to the 25 ity. The present invention fulfills these needs and provides maintenance of normal blood vessel conditions by decreas further related advantages. ing capillary permeability and fragility. Bioflavonoids have also been found to have activity as a histamine release SUMMARY OF THE INVENTION blocker (treatment of allergies), a xanthine oxidase inhibitor In brief, the present invention is directed to quercetin (treatment of gout), an aldose reductase inhibitor chalcone. In one embodiment of this invention, methods for (prevention of diabetic complications), a phospholiphase A2 the preparation of quercetin chalcone are disclosed. In and lipoxygenase inhibitor (anti-inflammatory), an aerobic another embodiment, compositions including quercetin glycosis inhibitor (an anti-cancer agent), and a tumor necro chalcone and an acceptable carrier and/or diluent are dis sis factor potentiator (an antiviral agent. closed. In a further embodiment, this invention discloses 35 methods of administering quercetin chalcone to a warm blooded animal to treat a variety of conditions or illnesses, However, despite their promise for a variety of medicinal including allergies. applications, the utility of bioflavonoids have been limited These and other aspects of this invention will be apparent by their poor absorption into the bloodstream due, at least in of a reference to the following detailed description. part, to their low Solubility under physiological conditions. 40 For example, quercetin (i.e., 3,3',4',5,7-O penta DETAILED DESCRIPTION OF THE hydroxyflavone), has been the Subject of extensive study, INVENTION and has the following Structure The present invention is generally directed to an effective, 45 OH soluble and bioavailable bioflavonoid and, more specifically, to quercetin chalcone, which is an effective, Soluble and bioavailable quercetin derivative. Quercetin chalcone is HO O more Soluble and provides for greater absorption than quer OH cetin under physiological conditions, and thus provides 50 enhanced bioavailability compared to quercetin. The Struc OH ture of querce tin chalcone (i.e., 2',3,4,4',6'- OH O pentahydroxychalcone) is presented below. OH 55 Quercetin is absorbed to the extend of about 1% from an HO OH oral dose. Effective cellular uptake of quercetin appears to OH require the use of water-miscible Solvents Such as dimeth ylsulfoxide. Furthermore, while other bioflavonoids have OH been found to be more Soluble than quercetin under physi 60 ological conditions, these compounds appear to be leSS OH O effective than quercetin. Referring to the above Structure, quercetin chalcone has Chalcones, a class of bioflavonoids, have shown promise 65 five phenolic hydroxy groups and an enol group (while in overcoming the limitations of other bioflavonoid quercetin has four phenolic hydroxy groups and an enol compounds, and have the following general Structure. group). The increased Solubility of quercetin chalcone rela 5,977, 184 3 4 tive to quercetin is due, at least in part, to the additional plished by treating quercetin with an aqueous alkali metal phenolic hydroxy group. Moreover, unlike other highly Salt Solution. Suitable alkali metal Salts include Sodium soluble chalcone bioflavonoids, the solubility of quercetin hydroxide and potassium hydroxide. Upon drying of the chalcone is not accomplished through the presence of other alkali reaction mixture, quercetin chalcone is recovered. bioactivity-limiting Substituents, Such as Sugar or polysac In another embodiment of the present invention, compo charide Substituents. Sitions containing quercetin chalcone are disclosed. To this In one aspect of the present invention, a method for end, quercetin chalcone may be formulated for the purposes preparing quercetin chalcone is disclosed. In this method, of administration, as an administratable composition. Such quercetin chalcone is prepared from rutin (i.e., quercetin compositions comprise quercetin chalcone and an accept rutinoside) in two steps (1) rutinoside hydrolysis, and (2) able carrier and/or diluent, and quercetin chalcone is present chalcone conversion. In one embodiment, the first Step is in the composition in an effective amount. Preferably, the rutinose hydrolysis in which rutin is hydrolized to quercetin. compositions of this invention
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