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(12) Patent Application Publication (10) Pub. No.: US 2009/0285919 A1 Alberte Et Al US 20090285919A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0285919 A1 Alberte et al. (43) Pub. Date: Nov. 19, 2009 (54) RCE BRAN EXTRACTS FOR filed on Sep. 30, 2008, provisional application No. NFLAMMATION AND METHODS OF USE 61/147,305, filed on Jan. 26, 2009. THEREOF Publication Classification (76) Inventors: Randall S. Alberte, Estero, FL (51) Int. Cl. (US); William P. Roschek, JR., A 6LX 36/899 (2006.01) Naples, FL (US) A2.3L I/28 (2006.01) Correspondence Address: A6IP 29/00 (2006.01) FOLEY HOAG, LLP A6IP 25/00 (2006.01) PATENT GROUP, WORLD TRADE CENTER A6IP35/00 (2006.01) WEST (52) U.S. Cl. ......................................... 424/750; 426/655 155 SEAPORT BLVD BOSTON, MA 02110 (US) (57) ABSTRACT The present invention relates in part to stabilized rice bran (21) Appl. No.: 12/467,835 extracts enriched in compounds that have inhibitory activity against certain anti-inflammatory therapeutic endpoints, such (22) Filed: May 18, 2009 as the COX-1, COX-2 and 5-LOX enzymes. Another aspect of the invention relates to pharmaceutical compositions com Related U.S. Application Data prising the extracts and to methods of treating inflammatory (60) Provisional application No. 61/054,151, filed on May diseases comprising administering the aforementioned 18, 2008, provisional application No. 61/101.475, eXtractS. Patent Application Publication Nov. 19, 2009 Sheet 1 of 6 US 2009/0285919 A1 Figure l Arachidonic Acid NSAIDs inhibition Prostaglandins PRO-NFLAMMATORY Arthritis (OA & RA) Patent Application Publication Nov. 19, 2009 Sheet 2 of 6 US 2009/0285919 A1 S.---------------Sssssssssss &s asy xxx s -Yvxxxxxxxxxxxxxxxxxxxx xxxx-xxxxxxxxxx:x O SSSSS i Patent Application Publication Nov. 19, 2009 Sheet 3 of 6 US 2009/0285919 A1 s k's se Sces SS Sasa SS W s sex&s SNYSS SY wass saxsex's ax xxx Patent Application Publication Nov. 19, 2009 Sheet 4 of 6 US 2009/0285919 A1 SSSSSSSSS as: SS Sw & ses YYYYYYYYYYYYYYYYY-axYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYYY.saw AYYYYYYYYYYYYSR S. S 'ty?an81-J S. Patent Application Publication Nov. 19, 2009 Sheet 5 of 6 US 2009/0285919 A1 09.tz00709800809Z00Z09.T. Patent Application Publication Nov. 19, 2009 Sheet 6 of 6 US 2009/0285919 A1 09~ US 2009/02859 19 A1 Nov. 19, 2009 RICE BRAN EXTRACTS FOR vents the propagation of free radical reactions. Because of its NFLAMMATION AND METHODS OF USE radical scavenging antioxidant properties, vitamin E inhibits THEREOF lipid peroxidation in vitro and in vivo. Tocotrienols also have antitumor action against breast cancers and possible benefi RELATED APPLICATIONS cial effects on cardiovascular health, and they decrease serum 0001. This application claims the benefit of priority to total cholesterol and LDL cholesterol levels (Ardiansyah, H. U.S. Provisional Application Nos. 61/054,151, filed on May Shirakawa, T. Koseki, K. Ohinata, K. Hashizume and M. 18, 2008, 61/101,475, filed on Sep. 30, 2008, and 61/147,305, Komai, 2006. Rice bran fractions improve blood pressure, filed on Jan. 26, 2009, each of which is herein incorporated by lipid profile, and glucose metabolism in Stroke-prone spon reference in its entirety. taneously hypertensive rats, J. Agric. Food Chem. 54: 1914 1920; T. Akihisa, K. Yasukawa, M. Yamaura, M. Ukiya, Y. BACKGROUND OF THE INVENTION Kimura, N. Shimizu and K. Arai, 2000. Triterpene alcohol and sterol ferulates from rice bran and their anti-inflamma 0002 Rice (Oryza sativa) bran, comprising 10% of the tory effects, J. Agric. Food Chem. 48:2313-2319; A. total rice grain, is a by-product of rice milling industry with Idouraine, M.J. Khan and C. W. Weber, 1996. In vitrobinding world production of about 50-60 million metric tons per year. capacity of wheat bran, rice bran, and oat fiberfor Ca,Mg, Cu, Rice bran is an excellent source of lipids, especially unsatur ated fatty acids. Rice bran oil contains an array of bio-active and Zn alone and in different combinations, J. Agric. Food phytochemicals such as ory Zanols, phytostetols, tocotrienols, Chem. 44:2067-2072: E. H. Jung, S. Ran Kim, I. K. Hwang flavonoids, vitamins, squalene, polycosanols, phytic acid, and T. Youl Ha, 2007. Hypoglycemic effects of a phenolic ferulic acid, inositol hexaphophate. Additional constituents acid fraction of rice bran and ferulic acid in C57BL/KSJ-db/ of the bran include protein (11-15%), carbohydrates (34 db mice, J. Agric. Food Chem. 55.9800-9804; R. Renuka 62%), ash (7-10%), vitamins, minerals and crude fibers Devi and C. Arumughan, 2007. Antiradical efficacy of phy (7-11%) (M. C. Kik, 1956. Nutritive value of rice, nutrients in tochemical extracts from defatted rice bran, Food Chem. Toxi rice bran and rice polish and improvement of protein quality col. 45:2014-2021). with amino acids, J. Agric. Food Chem. 4: 170-172; C. A. 0005 Various techniques used for extraction, isolation Rohrer and T. J. Siebenmorgen, 2004. Nutraceutical concen and purification of antioxidants from rice bran have been trations within the bran of various Rrice kernel thickness described in literature. (M. H. Chen and C.J. Bergman, 2005. fractions, Biosys. Eng. 88:453-460). A rapid procedure for analysing rice bran tocopherol, tocot 0003 Rice bran oil contains 95.6% saponifiable lipids, rienol and gamma-oryZanol contents, Journal of Food Com including glycolipid and phospholipids; and 4.2% unsaponi position and Analysis. 18:319-331 )A rapid procedure for fiable lipids, including tocopherols, tocotrienols, Y-ory Zanol, analyzing rice brantocopherol, tocotrienol and ory Zanol con sterols and carotenoids. The Saponifiable lipids are mainly tents by using hexane, isopropanol and methanol as solvents triglycerides. However, these triglycerides are easily hydro has been developed (S. Lilitchan, C. Tangprawat, K. Aryusuk, lyzed by lipase to form fatty acids. Y-ory Zanol content in the S. Krisnangkura, S. Chokmoh and K. Krisnangkura, 2008. rice bran oil is approximately 0.98%-2.9%. The Y-oryZanol is Partial extraction method for the rapid analysis of total lipids a mixture of 10 ferulate esters of triterpene alcohol that have and gamma-ory Zanol contents in rice bran, Food Chem. been characterized extensively. The Y-oryZanols protect rice 106:752-759). It was found that the tocopherol, tocotrienol bran oil from oxidation, inhibit peroxidation of lipids medi and oryzanol in fresh rice bran were 98.3 mg/g, 223.6 mg/g ated by iron or UV irradiation, and has been shown to lower and 3.4-3.9 mg/g fresh bran weight. Renuka Devi et al. (R. blood cholesterol and used to treat nerve imbalance (C. Agui Renuka Devi and C. Arumughan, 2007. Antiradical efficacy lar-Garcia, G. Gavino, M. Baragano-Mosqueda, P. Hevia and of phytochemical extracts from defatted rice bran, Food V. C. Gavino, 2007. Correlation of tocopherol, tocotrienol, Chem. Toxicol. 45:2014-2021) provided (R. Renuka Devi and gamma-oryZanol and total polyphenol content in rice bran C. Arumughan, 2007. Phytochemical characterization of with different antioxidant capacity assays, Food Chem. 102: defatted rice bran and optimization of a process for their 1228-1232; Ardiansyah, H. Shirakawa, T. Koseki, K. Ohi extraction and enrichment, Bioresource Technology. nata, K. Hashizume and M. Komai, 2006. Rice bran fractions 98:3037-3043) a phytochemical characterization of defatted improve blood pressure, lipid profile, and glucose metabo rice branand optimization of a process for their extraction and lism in stroke-prone spontaneously hypertensive rats, J. enrichment. The yield of total phenols, oryzanols and ferulic Agric. Food Chem. 54: 1914-1920). The major components of acid with methanol were 0.22, 0.03 and 0.023%, respectively. Y-ory Zanol in rice bran are cycloartenyl ferulate, 24-methyl Microwave assisted solvent extraction is a relatively new ene cycloartanyl ferulate and campestanyl ferulate (S. Lilit extraction method that has be used for oil extractions. More chan, C. Tangprawat, K. Aryusuk, S. Krisnangkura, S. Chok recently, supercritical carbon dioxide (SCCO) extractions moh and K. Krisnangkura, 2008. Partial extraction method have shown that the odor and the flavor of extracted oil are for the rapid analysis of total lipids and gamma-oryZanol superior to that obtained by traditional solvent extraction. (C. contents in rice bran, Food Chem. 106:752-759). Balachandran, P. N. Mayamol, S. Thomas, D. Sukumar, A. 0004 Rice bran oil contains about 0.1-0.14% vitamin E. Sundaresan and C. Arumughan, 2008. An ecofriendly Vitamin E is a generic term for a group of four tocopherols approach to process rice bran for high quality rice bran oil (Cl-, 3-, y- and 6-) and four tocotrienols (Cl-, 3-, y- and Ö-), of using Supercritical carbon dioxide for nutraceutical applica which C-tocopherol has the highest biological activity. All tions, Bioresource Technology. 99:2905-2912) SCCO, components of vitamin E have an amphiphilic structure with extraction can overcome limitations of traditional techniques a hydrophilic (chromanol ring) and a hydrophobic dominant that affect extract quality. As a solvent, CO is non-toxic and (isoprenoid side chain). A number of studies showed that can be easily and completely removed from products; more Vitamin E functions as a chain-breaking antioxidant that pre over, it is non-corrosive and non-flammable. In addition to the US 2009/02859 19 A1 Nov. 19, 2009 well characterized oil and fatty acid components of rice bran, but they still do not synthesize PGD, TxB or PGF (J. M. rice bran is rich in phenolics, alkaloids, gingerols and terpe Bathon, F. H. Chilton, W. C. Hubbard, M. C. Towns, N. J. CS. Solan and D. Proud, 1996. Mechanisms of prostanoid syn 0006. The inflammatory cascades responsible for pain, thesis in human synovial cells: cytokine-peptide synergism, join immobility and swelling in osteoarthritis (OA) and rheu Inflammation. 20:537-554).
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