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(12) Patent Application Publication (10) Pub. No.: US 2009/0148433 A1 Naidu Et Al US 20090148433A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2009/0148433 A1 Naidu et al. (43) Pub. Date: Jun. 11, 2009 (54) METALLO-PROTEIN AND TOCOTRIENOL Publication Classification (MP-T3) COMPOSITIONS AND USES (51) Int. Cl. THEREOF A638/47 (2006.01) A638/40 (2006.01) (75) Inventors: A. Satyanarayan Naidu, Diamond A633/06 (2006.01) Bar, CA (US); A.G. Sreus Naidu, A633/04 (2006.01) Diamond Bar, CA (US) (52) U.S. Cl. ........ 424/94.61; 514/12: 424/682: 424/702: 424/687; 424/655 Correspondence Address: KNOBBE MARTENS OLSON & BEAR LLP (57) ABSTRACT 2040 MAINSTREET, FOURTEENTH FLOOR Metallo-proteins including but not limited to lactoferrin (LF), IRVINE, CA 92.614 (US) transferrin (TF) and ovotransferrin (OTF) (all members of transferrin family), ceruloplasmin (CP) and metallo-thionein (73) Assignee: Naidu LP, Pomona, CA (US) (MT) were found to stabilize and enhance the bio-functional activity of tocotrienol (T3), T3 mixtures or derivates. The (21) Appl. No.: 12/327,712 synergism between MP and T3 also promote the intestinal transfer and the ultimate bio-availability of T3 and T3-deriva (22) Filed: Dec. 3, 2008 tives for physiological functions. Such functional synergism includes hypocholesterolemic, anti-thrombotic, antioxidant, anti-athermogenic, anti-inflammatory and immuno-regula Related U.S. Application Data tory activities of T3 agents. These T3 compositions are useful (60) Provisional application No. 61/012,008, filed on Dec. as pharmaceuticals, in cosmetics, in foods and as nutritional 6, 2007. Supplements. Cholesterol biosynthesis and site-specific interference of pathways by Statins, T3 and MP Acetyl-CoA + Acetoacetyl-CoA SNS ACN 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) HMG-CoA Reductase Mewallonate isopenty pyrophosphate eranyl pyrophosphate Prenylated Proteins Coenzyme-Q10 arensyl pyrophosphate lanosterol Figure Legends: (S) = inhibitory activity of Statins < = inhibitory activity of T3 inhibitory activity of metallo-protein (LF) Patent Application Publication Jun. 11, 2009 US 2009/0148433 A1 Figure-1 Cholesterol biosynthesis and site-specific interference of pathways by Statins, T3 and MP Acetyl-CoA + Acetoacetyl-CoA 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA) HMG-CoA Reductase Mevalonate lsopentyl pyrophosphate eranyl pyrophosphate Prenylated Proteins Coenzyme-Q10 arensyl pyrophosphate CHOLESTEROL Š lanosterol Squalene : P ACTION Figure Legends: = Inhibitory activity of Statins = Inhibitory activity of T3 = Inhibitory activity of metallo-protein (LF) US 2009/O 148433 A1 Jun. 11, 2009 METALLO-PROTEIN AND TOCOTRENOL halogenated C-14 side-chain compound under conditions of (MP-T3) COMPOSITIONS AND USES palladium-catalyzed cross-coupling. US Patent Application THEREOF 20050124687 discloses a process to derive d-T3 from a (2S) 2-hydroxymethyl-6-hydroxy-alkylchroman compound, RELATED APPLICATIONS through reaction with a famesyl Grignard or Sulfone com pound. 0001. This application claims priority to provisional U.S. Application No. 61/012,008, filed Dec. 6, 2007 which is incorporated herein by reference. Functional Properties of T3 Compounds 0010 T3s have been attributed with several nutritional and BACKGROUND OF THE INVENTION health benefits. The primary function of T3 is to serve as an 0002 1. Field of the Invention antioxidant. Epidemiological studies demonstrate a positive 0003 Embodiments of the invention relate to stabilized relationship between T3 and the prevention of atherosclerosis compositions containing tocotrienols. In particular, compo and vascular diseases, even those affecting the brain. T3 can sitions are stabilized by use of a metallo-protein such as promote the breakdown of homocysteine by lessening the lactoferrin, transferrin, ovotransferrin, ceruloplasmin, met adverse impact of oxidants on endothelial function and allo-thionein and metallo-protein complexes. The composi enhance gastric healing. The protective effect of T3 against tions are useful to treat conditions such as hyperlipidemia, viral or bacterial infections in experimentally challenged hypercholesteremia, atherosclerosis, diabetes and neurode young animals has been reported. Resistance to the flu was generative diseases. demonstrated in both young and old test animals. T3 Supple 0004 2. Description of the Related Art mentation may help to preventage-related macular degenera 0005 Vitamin E is one of the most important phytonutri tion. T3s are also needed for the health of cellular membranes, ents in edible oils. There are eight naturally occurring vitam which may help prevent blood clotting, protect lungs against ers (Substances having similar vitamin activity) of vitamin E. toxic damage, and can help with boosting immune function. They consist of tocopherols and tocotrienols, structurally T3s have been reported to have activity as anti-tumor agents similar molecules containing a two-ringed chromanol head and neuro-protective agents (Schaffer S, et al. J Nutr 35:151 and a 16-carbon phytyl tail. In the tocopherols, the phyty1 154, 2005). The major functional activities of T3 are eluci tail is saturated; in the tocotrienols it contains three double dated below. (unsaturated) bonds. All natural E vitamers are in a spatial 0011 Management of serum cholesterol: A high blood form known as the R.R.R-stereoisomer conformation. (The cholesterol level is one of the major risk factors for cardio riault A, et al. Clin Biochem 32:309-319, 1999) vascular diseases. T3 has a number of beneficial properties in 0006 Tocotrienols (T3) are found primarily in the oil frac cholesterol reduction and reversing atherosclerosis. The tion of rice bran, palm fruit, barley, and wheat germ. Natural interaction of T3 with the mevalonate pathway leads to the T3 exists in four different forms or isomers, named alpha-(5. lowering of serum cholesterol levels. Several studies revealed 7,8-trimethyl), beta-(5,8-dimethyl), gamma-(7,8-dimethyl) that supplementation with T3 or T3-rich fractions (TRF) and delta-(8-monomethyl), which contain different number results in significant reduction in serum total cholesterol (15 of methyl groups on the chromanol ring. Although all the 42%) and low-density lipoprotein (LDL) cholesterols isomers are potent free radical scavengers due to the ease of (8-62%) in chicken and hyperlipidemic pigs. (Qureshi AA, et donating a hydrogen atom from the hydroxyl group on the al. Am J Clin Nutr 53:1021-1026, 1991: Qureshi AA, et al. chromanol ring, each T3 form exhibits a distinct biological Lipids 30: 1171-1177, 1995; Black T M. et al. J Nutr 130: activity. (Tan B. J. Am Nutr Assoc 8:35-42, 2005) 2320-2426, 2000; Chao J.T. etal.JNutr Sci Vitaminol 48:332 0007 T3 concentrates and isomers can be obtained 337, 2002). through purification processes from several natural sources 0012. Different T3 isomers show varying degrees (about such as palm olein and rice bran oil. These T3 isolation 30-fold) of cholesterol-lowering ability. Accordingly, T3 iso procedures are intricate and difficult to do on a large scale. mers inhibit cholesterol synthesis, in decreasing order, delta The Malaysian Palm Oil Board (MPOB) spearheaded exten T3>gamma-T3>alpha-T3>beta-T3. Concurrent administra sive research and development in oil palm cultivation and tion of alpha-tocopherol seems to interfere with the revolutionized the global production of palm oil T3 and T3 hypocholesterolemic effects of T3. Thus, limiting toco derivatives for food and pharmaceutical applications. pherols within 20% of tocols mixture is proposed to achieve 0008 U.S. Pat. No. 6,838,104 teaches a process to recover better therapeutic activity. The counteraction among vitamin high yields of T3 compounds from biological sources such as E analogs was more obvious when serving T3 at a high dose palm oil, cereals, grains, and grain oils. U.S. Pat. No. 6,395, due to more conversion of T3 to tocopherol in the plasma. 915 describes a large-scale process to isolate T3 isomers from (Qureshi AA, et al. Am J Clin Nutr 53:1021-1026, 1991; tocopherols using reverse phase partition liquid chromatog QureshiAA, et al. J Nutr 126:389-394, 1996: QureshiAA et raphy. U.S. Pat. No. 6.224,717 describes a method for sepa al., J Agric Food Chem 48:3130-3140, 2000). rating T3 from tocol admixtures. U.S. Pat. No. 5,670,668 0013 The molecular mechanism for suppression of cho discloses isolation and purification of D-gamma-T3 by crys lesterol biosynthesis by T3 has been ascribed to the side tallization and recrystallization procedures. chain's unique ability to increase cellular farnesol, a meva 0009. Several synthetic methods to derive d-T3 com lonate-derived product, which signals the proteolytic pounds from various organic chemicals are known in the prior degradation of 3-hydroxy-3-methylglutaryl-coenzyme art. U.S. Pat. No. 7,038,067 describes a method to synthesize (HMG-CoA) reductase activity. This mechanism differs from D-T3 from a (2S)-vinyl-chromane compound, through that of statins, the well-known HMG-CoA inhibitors, which hydroboration of the (2S)-vinyl-chromane to provide an orga block the enzyme as a chemical analog of substrate HMG noborane, followed by coupling the organoborane with a CoA, by competitive inhibition. (Qureshi AA, et al. J Biol US 2009/O 148433 A1 Jun. 11, 2009 Chem 261:10544-10550, 1986; Parker RA, et al. JBiol Chem Chem 278:43508-43515, 2003: Sen CK, et al. Ann NYAcad 268: 11230-11238; Correll C C, Edwards PA. J Biol Chem Sci 1031: 127-42, 2004; Osakada F. etal. Neuropharmacology 269:633-638, 1994). 47:904-915, 2004) 0014. Management of serum cholesterol levels could 0021 Oral supplementation of palm oil T3 complex to reduce the risk of cardiovascular disease, one of the most spontaneously hypertensive rats led to increased T3 level in important causes of morbidity and mortality, especially in the brain. The rats supplemented with T3 showed more pro men and women >60 years old. Most popular and effective tection against Stroke-induced injury compared to controls anti-cholesterol drug is statin (Atovastatin, Simvastatin, (non-supplemented group). This study demonstrated that oral Lovastatin, Pravastatin, etc.) which occupy S22 billion annual Supplementation of the palm T3 complex acts onkey molecu market for hypercholesterolemia patients.
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