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Anti-inflammatory cranberry flavonol extract preparations

a flavonol and extract technology, applied in the field of extracts of cranberries, can solve the problems of reducing the yield of quercetin-3-o-(6′′-benzoyl)--galactoside, causing severe bladder pain, and reducing the yield of quercetin-3-o-(6′′-benzoyl)-galactoside, so as to increase the yield of quercetin-3-o-galactoside and reducing side effects

Inactive Publication Date: 2007-12-20
VORSA NICHOLI +4
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recurrent use of antibiotics can lead to pathogen resistance and result in deleterious side effects and toxicity reactions.
Moreover, urinary tract inflammation is a painful and often debilitating symptom of bacterial infection as well as many diseases of both known and unknown etiology.
Moreover, although cystitis is not as deadly as its renal counterpart, it is associated with pervasive inflammation giving rise to severe bladder pain as well as frequent, urgent, and painful urination.
Cystitis is also often a recurrent condition, resulting in long term and often debilitating discomfort for those afflicted.
Unfortunately, the causes of the battery of adverse conditions affecting the urinary tract are only partially understood.
Cystitis may also embody urinary tract inflammation due to a number of non-bacterial sources, for example, allergic responses to food or insufficient water intake, which allows the bladder and urethral tissues to become dry, thus leading to deposition of crystallized uric acid on the tissues and associated irritation.
It is a source of frustration for both doctors and patients alike, as it has no apparent infective cause and is frequently debilitating.
Unfortunately, many of these treatments are themselves painful, and many are also unsuitable for personal treatment in the home.
However, Walker failed to provide any experimental data correlating biological activity with a specifically identified compound.
Using this process with an aqueous solution of commercially available Ocean Spray cranberry powder, Walker reported obtaining a single active compound and partially characterized the compound but failed to provide its chemical structure.
The Walker assay methods could not distinguish between anti-adherence activities with respect to type 1 or type P E. coli, thus Walker was also unable to characterize the biological activity of this compound.
However, as bladder infections are associated with type 1 fimbriated E. coli, the anti-adherence activity of these compounds is ineffective for the treatment of bacterial cystitis.
Originally, this antimicrobial activity was thought to arise from acidification of the urine due to the intake of cranberry juice, resulting in an unfavorable environment for bacterial survival.
Moreover, inflammation of the urinary tract may also arise from non-bacterial sources, in which case such anti-adherence activities are therapeutically ineffective.
However, substances such as papain are allergenic to many individuals, and these enzymes have caustic and corrosive effects on the digestive mucous membranes.

Method used

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  • Anti-inflammatory cranberry flavonol extract preparations
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  • Anti-inflammatory cranberry flavonol extract preparations

Examples

Experimental program
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Effect test

example 1

Isolation and Characterization of Flavonol Glycosides and Aglycones from Cranberry Powder

Reagents

[0042] All reagents were purchased from Fisher Scientific (PA) and Sigma (MO) and were of analytical or HPLC grade. Dimethylsulfoxide (DMSO)-d6 (99.96% D) was obtained from Cambridge Isotope Laboratories (MA). Standards of quercetin-3-galactoside, quercetin-3-glucoside, quercetin-3-rhamnoside, quercetin, myricetin and kaempferol were purchased from INDOFINE Chemical Company, Inc. (NJ). Sephadex™ LH-20 for column chromatography was obtained from Amersham Pharmacia Biotech AB (Sweden).

Extraction and Fractionation of Flavonoids

[0043] Flavonoids from 1.0 kg of freeze dried cranberry powder 90-MX supplied by Ocean Spray Cranberries, Inc., (MA) were extracted twice with 80% acetone / water (v / v) (1:10), filtered and partially evaporated under reduced pressure at 35° C. to remove the acetone. The resultant aqueous phase was defatted by extraction with hexane (1:1) and the aqueous layer was ...

example 2

Anti-Inflammatory Activity of Sephadex LH-20 Eluate Fractions

[0076] The anti-inflammatory activities of different classes of cranberry phenolic compounds separated by Sephadex LH-20 column chromatography were tested in vivo with the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema assay described previously (Huang et al. 2003). Each of the treatments was topically applied to both ears of four female CD-1 mice. Treatments included application of either acetone or curcumin controls or the test extract in 20 μl of acetone twenty minutes prior to application of either 5 mg of acetone alone or 1 nmol of TPA in acetone. At five hours post-treatment, mice were sacrificed and 6 mm diameter ear punch biopsies were taken and weighed. Curcumin, a well-known anti-inflammatory agent, was used as a positive control (Chan et al. 1994; Chan 1995). Data were analyzed statistically using ANOVA and the Student-Neuman-Kuels (SNK) multiple means separation test (P≦0.05). The ratio of ...

example 3

Anti-Inflammatory Activity of Quercetin-3-O-(6″-benzoyl)-β-Galactoside

[0077] The anti-inflammatory activity of quercetin-3-O-(6″-benzoyl)-β-galactoside (Peak 19) was tested in vivo with the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema assay. Each of the treatments was topically applied to both ears of at least five CD-1 female mice. Treatments included application of either acetone or curcumin controls or the test extract in 20 μl of acetone twenty minutes prior to application of 1.5 nmol of TPA in acetone. After 7 hours post-treatment, mice were sacrificed and 6 mm diameter ear punch biopsies were taken and weighed. The ratio of the difference in the weight of ear punches between TPA treated groups receiving pretreatments of acetone and the test extract, respectively, to the difference in the weight of ear punches between acetone pretreated groups subsequently treated with TPA and acetone, respectively, indicates the degree of anti-inflammatory activity of th...

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Abstract

The present invention is directed to extracts of cranberries (Vaccinium macrocarpon) comprising either mixed flavonols that are substantially free of anthocyanins and proanthocyanidins or a purified cranberry flavonol compound, including myricetin-3-β-xylopyranoside, quercetin-3-β-glucoside, quercetin-3-α-arabinopyranoside, 3′-methoxyquercetin-3-α-xylopyranoside, quercetin-3-O-(6″-p-coumaroyl)-β-galactoside, and quercetin-3-O-(6″-benzoyl)-β-galactoside. The present invention also embodies the use of those extracts, as well as extracts comprising the cranberry flavonol compound quercetin-3-α-arabinofuranoside, for the treatment of inflammatory disorders. Pharmaceutical, food, dietary supplement, and cosmetic compositions utilizing the extracts or compounds of the present invention are also recited.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] The present application claims priority under 35 USC §119(e) to U.S. Provisional Application Ser. No. 60 / 518,294, filed on Nov. 10, 2003, which is incorporated by reference in its entirety herein.FIELD OF THE INVENTION [0002] The present invention is directed to extracts of cranberries (Vaccinium macrocarpon) comprising either mixed flavonols that are substantially free of anthocyanins and proanthocyanidins or a purified cranberry flavonol compound, including myricetin-3-β-xylopyranoside, quercetin-3-β-glucoside, quercetin-3-α-arabinopyranoside, 3′-methoxyquercetin-3-α-xylopyranoside, quercetin-3-O-(6″-p-coumaroyl)-β-galactoside, and quercetin-3-O-(6″-benzoyl)-β-galactoside. The present invention also embodies the use of those extracts, as well as extracts comprising the cranberry flavonol compound quercetin-3-α-arabinofuranoside, for the treatment of inflammatory disorders, particularly irritation of the urinary tract due to both bacte...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K36/45A23L1/30A23L2/02A61P43/00C07D311/00A61P29/00A61K31/352
CPCA23L1/3004A61K36/45A61K31/7048A61K31/353A23L33/11A61P29/00A61P43/00
Inventor VORSA, NICHOLIVVEDENSKAYA, IRINA O.HUANG, MOU-TUANROSEN, ROBERT T.ROSEN, SHARON L.
Owner VORSA NICHOLI
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