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(12) United States Patent (10) Patent No.: US 9,655,935 B2 Dreher Et Al

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(12) United States Patent (10) Patent No.: US 9,655,935 B2 Dreher Et Al USOO9655935B2 (12) United States Patent (10) Patent No.: US 9,655,935 B2 Dreher et al. (45) Date of Patent: *May 23, 2017 (54) POMEGRANATE FRUIT POLYPHENOL continuation-in-part of application No. 1 1/687,480, COMPOSITION AND METHODS OF USE filed on Mar. 16, 2007, now Pat. No. 7,943,185. AND MANUFACTURE THEREOF (60) Provisional application No. 60/888,763, filed on Feb. 7, 2007, provisional application No. 60/888,762, filed (71) Applicant: POM Wonderful LLC, Los Angeles, on Feb. 7, 2007. CA (US) (51) Int. Cl. (72) Inventors: Mark Dreher, Wimberley, TX (US); A636/85 (2006.01) Harley Liker, Los Angeles, CA (US); A63L/7048 (2006.01) Yair Steve Henig, Beverly Hills, CA A63L/366 (2006.01) (US) (52) U.S. Cl. CPC .......... A61K 36/185 (2013.01); A61 K3I/366 (73) Assignee: POM WONDERFUL, LLC, Los (2013.01); A61 K3I/7048 (2013.01) Angeles, CA (US) (58) Field of Classification Search None (*) Notice: Subject to any disclaimer, the term of this See application file for complete search history. patent is extended or adjusted under 35 U.S.C. 154(b) by 48 days. (56) References Cited This patent is Subject to a terminal dis U.S. PATENT DOCUMENTS claimer. 9,056,083 B2 * 6/2015 Dreher ................. A61K 36,185 (21) Appl. No.: 14/724,761 * cited by examiner (22) Filed: May 28, 2015 Primary Examiner — Chris R Tate (65) Prior Publication Data Assistant Examiner — Randall Winston (74) Attorney, Agent, or Firm — Cotman IP Law Group, US 2016/002275O A1 Jan. 28, 2016 PLC Related U.S. Application Data (57) ABSTRACT (63) Continuation of application No. 13/299.356, filed on A pharmaceutical composition with an active pharmaceuti Nov. 17, 2011, now Pat. No. 9,056,083, which is a cal ingredient including a pomegranate fruit polyphenol continuation-in-part of application No. 12/564,878, extract. The pomegranate fruit polyphenol extract includes filed on Sep. 22, 2009, now Pat. No. 8,658.220, which at least about 3% combined punicalagin A and punicalagin is a continuation of application No. 11/137,248, filed B by weight, less than about 5% elagic acid and their on May 24, 2005, now Pat. No. 7,611,738, said derivatives by weight, and less than about 1% anthocyanins application No. 13/299.356 is a continuation-in-part by weight. of application No. 1 1/745,440, filed on May 7, 2007, now Pat. No. 8,758,832, which is a 13 Claims, No Drawings US 9,655,935 B2 1. 2 POMEGRANATE FRUIT POLYPHENOL For example, a major polyphenol antioxidant called puni COMPOSITION AND METHODS OF USE calagin can by hydrolyzed into ellagic acid. Once puni AND MANUFACTURE THEREOF calagin hydrolyzes into ellagic acid its ability to offer antioxidant potency to the body is reduced since free elagic CROSS REFERENCE TO RELATED acid is not as bioavailable. When punicalagins are preserved APPLICATIONS in their original unhydrolyzed and then consumed, they can be absorbed into the bloodstream, and greater health benefits The present application is a continuation of U.S. patent can be obtained. Punicalagins are 100% water-soluble, application Ser. No. 13/299,356, filed on Nov. 17, 2011, highly bioavailable, and shown to possess a high absorption which is a continuation-in-part of U.S. patent application 10 rate up to 95%. Not only do punicalagins offer antioxidant activity on their own, they can break up into Smaller Ser. No. 12/564,878, filed on Sep. 22, 2009, which is a polyphenols that are also absorbed into the body. Punicala continuation application of U.S. patent application Ser. No. gins are one important component of pomegranate polyphe 11/137,248, filed on May 24, 2005, now issued as U.S. Pat. nols, but the total composition of the polyphenols them No. 7,611,738, all of which are herein incorporated by 15 selves is a complex mixture of numerous other components. reference for completeness of disclosure; the present appli Predominant types of pomegranate polyphenolic com cation is also a continuation-in-part of U.S. patent applica pounds are hydrolyzable tannins, which are found in the tion Ser. No. 1 1/745,440, filed on May 7, 2007, which claims peels (rind, husk, or pericarp), membranes, and piths of the priority to U.S. Provisional Application Ser. No. 60/888,763, fruit. Hydrolyzable tannins, including punicalagin, are Sus and U.S. Provisional Application Ser. No. 60/888,762, both ceptible to enzymatic and non-enzymatic hydrolysis. Other filed Feb. 7, 2007, and which is a continuation-in-part of hydrolyzable tannins are include gallic acid and elagic acid U.S. patent application Ser. No. 1 1/687,480, now issued as esters of core molecules that consist of polyols, such as U.S. Pat. No. 7,943,185, all of which are herein incorporated Sugars. During hydrolysis, gallotannins yield gallic acid and by reference for completeness of disclosure. glucose while elagitannins yield ellagic acid and glucose. 25 The reported soluble polyphenol content in pomegranate BACKGROUND OF THE INVENTION juice varies within the limits of approximately 0.2% to approximately 1.5%, and ellagic acid was measured in Field of the Invention commercial juices around 100 to around 3000 mg/L. The disclosure provided herein relates generally to pome For the reasons above, many of products claiming to granate extracts. More particularly, but not by way of 30 contain “natural pomegranate' may in fact have less con limitation, one or more embodiments enable oral or enteral centrated key ingredients or phytochemicals that have spe dosage forms containing phytochemicals from pomegranate cific health benefits. Hence there is a need to find ways to in a quantity reflecting that of the natural fruit itself. concentrate pomegranate phytochemicals, including poly Description of the Related Art phenol antioxidants such as punicalagins and its automers, The pomegranate is acclaimed for its health benefits and 35 in their bioavailable and bioactive. for its disease-fighting antioxidant potential. Antioxidants For the reasons above, many of products claiming to are important because they are believed to protect the body contain “natural pomegranate may in fact lack key ingre against free radicals, the harmful molecules that can cause dients or phytochemicals that have specific health benefits. heart disease, premature aging, Alzheimer's disease, blind Hence there is a need to find ways to concentrate pome ness, and a variety of cancers. 40 granate phytochemicals, including polyphenol antioxidants There are many kinds of antioxidants, some produced by Such as punicalagins and its automers, in their bioavailable the body and others derived from the foods we eat. When the and bioactive forms. body's natural antioxidant defenses are lowered, or greater For at least the reasons described above there is a need for amounts of free radicals are produced, the body becomes processes for producing an oral or enteral dosage form more dependent upon food sources of antioxidants. The 45 containing key phytochemicals from pomegranates. consumption of phytochemical-rich diet is associated with a reduced risk of chronic human illnesses such as certain types SUMMARY OF THE INVENTION of cancers, inflammation, and cardiovascular and neurode generative diseases. One or more embodiments of the pomegranate fruit Studies show pomegranate juice has more polyphenol 50 polyphenol extract described herein are directed to a phar antioxidants than any other drink, Such as red wine, green maceutical composition including an active pharmaceutical tea, blueberry juice, cranberry juice and orange juice. Two ingredient. The active pharmaceutical ingredient includes a common ways of consuming pomegranates are by eating the pomegranate fruit polyphenol extract including at least fleshy arils of the pomegranate fruit itself and by drinking about 3% combined punicalagin A and punicalagin B by the juice obtained from the arils. 55 weight, and less than about 5% elagic acid and their There are studies illustrating the beneficial effects of derivatives by weight, and less than about 1% anthocyanins pomegranate phytochemicals, including polyphenols, by weight. proanthocyanidins, hydrolysable tannins, etc. Hence it is The pharmaceutical composition further includes a phar desirable to gain whatever beneficial effects might be pres maceutically acceptable carrier in instances where a carrier ent by consuming pomegranate and its phytochemicals. The 60 is desired. oral route is the least invasive, most convenient route for In one or more embodiments of the pharmaceutical com administering pomegranate phytochemicals on a routine position, the pomegranate fruit polyphenol extract may basis. However, the pomegranate fruit is a difficult fruit to include between about 3% to about 8% combined puni consume and certain pomegranate phytochemicals may lose calagin A and punicalagin B by weight. For example, the their health beneficial effects by undergoing chemical reac 65 pomegranate fruit polyphenol extract may include between tions into less bioavailable and/or less bioactive forms about 3% to about 4% combined punicalagin A and puni during processing and storage of juices and extracts. calagin B by weight. In another instance, the pomegranate US 9,655,935 B2 3 4 fruit polyphenol extract may contain between about 4.5% to As used herein, the term “phytochemicals' refers collec about 8% combined punicalagin A and punicalagin B by tively to compounds which are naturally-occurring in the weight. In one or more embodiments, the pomegranate fruit pomegranate and to reaction products and metabolites of polyphenol extract includes at least about 20% combined these compounds, which are considered to have a beneficial punicalagin A and punicalagin B by weight. 5 effect on the human or animal health. Examples of such In one or more embodiments of the pharmaceutical com phytochemicals include, but not limited to phenolics, poly position, the pomegranate fruit polyphenol extract includes phenols, and phenolic acids, sterols and triterpenoids, fatty at least about 15% combined punicalagin and punicalin by acids and triglycerides, and alkaloids.
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