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(12) Patent Application Publication (10) Pub. No.: US 2013/0066048A1 Raskin Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2013/0066048A1 Raskin Et Al US 2013 OO66048A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2013/0066048A1 Raskin et al. (43) Pub. Date: Mar. 14, 2013 (54) METHODS OF OBTAININGNATURAL Publication Classification PRODUCTS FROM THE COMESTIBLE FLUIDS AND METHODS OF USE (51) Int. Cl. C07D 3II/02 (2006.01) (75) Inventors: Ilya Raskin, Manalapan, NJ (US); C07K I4/435 (2006.01) Diana Roopchand, Highland Park, NJ C07D 3 II/78 (2006.01) (US); Slavko Komarnytsky, Somerset, C07C39/10 (2006.01) NJ (US) C07C 49/175 (2006.01) (52) U.S. Cl. (73) Assignee: Rutgers, The State University of New USPC ........... 530/350; 549/406:568/729; 549/400; Jersey, New Brunswick, NJ (US) 568/308; 549/279 (21) Appl. No.: 13/583,172 (57) ABSTRACT (22) PCT Filed: Mar. 14, 2011 (86) PCT NO.: PCT/US11/28347 Described herein is an enriched substance containing a ground edible material comprising one or more concentrated S371 (c)(1), bioactive natural products from plant juice, as well as meth (2), (4) Date: Nov. 19, 2012 ods of producing such enriched Substances and methods of using Such solids to provide beneficial effects to humans or Related U.S. Application Data other animals. Enriched foods comprising the enriched Sub (60) Provisional application No. 61/381,410, filed on Sep. stance(s) are also provided. Also provided are non-Sorbed 9, 2010, provisional application No. 61/314,017, filed natural products such as Sugars, fats oils, and carotenoids on Mar. 15, 2010. found in the non-Sorbed plant liquor fraction of plant juice. US 2013/0066048 A1 Mar. 14, 2013 METHODS OF OBTAININGNATURAL 0005 (a) combining the comestible fluid with an ingest PRODUCTS FROM THE COMESTIBLE ible sorbing material to form FLUIDS AND METHODS OF USE 0006 (i) an admixture containing an enriched sub stance comprising a natural product from the comes BACKGROUND tible fluid sorbed to the ingestible sorbing material; 0001. It is well known that many foods contain numerous and health/wellness-promoting and disease-preventing/curing 0007 (ii) a liquor comprising a non-sorbed natural compounds (Schmidt et al., Nat. Chem. Biol. 3:360-366, product from the comestible fluid; and 2007: Raskin et al., Curr. Pharm. Design, 10:3419-3429, 0008 (b) separating the enriched substance and the 2004). Plants are a particularly rich source of such com liquor, thereby obtaining the Sorbed natural product and pounds. Unfortunately, the co-evolution of people and edible the non-sorbed natural product from the comestible plants and the advance of modern agriculture have favored the fluid. reduction of beneficial, bioactive natural products in plant 0009. The comestible fluidis, in some embodiments, plant foods (Schmidt et al., Met. Clin. Exp., 57:S3-S9, 2008). juice, a dairy product, or a plant juice containing protein as Extensive plant breeding and selection has reduced the con these terms are defined herein. tent of healthy ingredients, such as various antioxidants, 0010. In another aspect, described herein is a method of polyphenols, bioflavonoids, glucosinolates, healthy fibers, concentrating a Sorbable natural product from plant juice in fatty acids, vitamins, and minerals in most plant foods edible form comprising: combining the plant juice with a (Schmidt et al., supra). This reduction was caused by the need ground edible material to form an admixture containing an to maximize the caloric content, palatability, and digestibility enriched Substance comprising a sorbed natural product from of plant foods by directing plant metabolism to accumulating the plant juice; and a plant liquor comprising a non-Sorbed starches, Sugars, oils, and/or major proteins in edible parts at natural product from the plant juice; and separating the the expense of losing bioactive secondary metabolites. As a enriched Substance from the plant juice, thereby concentrat result, many health promoting- and disease-fighting natural ing the Sorbabl, e.g., sorbed, e natural product from the plant products and bioactives were reduced to levels where average juice in edible form. In some embodiments, the sorbable daily consumption cannot produce measurable health ben natural products are sorbed (i.e., absorbed and/or adsorbed), efits. To supply a beneficial amount of plant-derived bioac to the ground edible material. In one embodiment, the sorb tives, food plants are then extracted with solvents and sold in able natural products are adsorbed to the ground edible mate oral form as concentrated Supplements rial. In some embodiments, the enriched Substance is Subse 0002 Ion-exchange chromatography can be used for con quently incorporated into a consumer product. For example, centrating and isolating a great variety of compounds. It is in one embodiment, the enriched substance is incorporated based on specific electrostatic interactions between charges into a food product. In other embodiments, the enriched sub on the Surface of solubilized compounds and solid ion stance is incorporated into a cosmetic product or a pharma exchangers (resins). As a result, some compounds bind to the ceutical product. ion exchange matrix, while others remain in the solution. 0011. Also provided, in another aspect, is a method of Ion-exchangers and compounds should be in the same polar producing a plant liquor from plantjuice comprising combin ity range to effectively bind to each other. However, ion ing plant juice with a ground edible material to form an exchange chromatography is very expensive because it uses admixture containing an enriched substance comprising a synthetic resins and organic solvents to elute bound phy Sorbable natural product from the plant juice; and a plant tochemicals from resins. In addition to high cost, this method liquor comprising a non-Sorbed natural product from the is often not allowed in food manufacturing and cannot be plant juice; thereby producing a plant liquor from the plant called “natural or “organic.” juice. In some embodiments, the plant liquor is Subsequently used as a food additive (e.g., natural Sweetener, flavoring or SUMMARY OF THE INVENTION coloring). In some embodiments, the soluble carbohydrates 0003. The present disclosure is based on the discovery that in the plant liquor are Subsequently used as a natural Sweet ingestible sorbing material effectively binds and retains sorb ener. In other embodiments, the plant liquor is Subsequently able natural products obtainable from plant material (e.g., by incorporated into a cosmetic product or a pharmaceutical homogenization, extraction, Squeezing or juicing) as well as product. from dairy products. As described herein, the ingestible sorb 0012. In some embodiments, if either the enriched sub ing material generally does not sorb high-calorie Sugars or stance or the plant liquor is incorporated into a food product, fats associated with most commercial fruit juices. This dis the other is not incorporated into the same food product. In covery enables a one-step concentration and separation of other embodiments, the enriched substance and the plant Sorbable natural products (e.g., phytochemicals of moderate liquor are incorporated into the same food product. hydrophilicity and/or hydrophobicity from plantjuice or pro 0013 For any of the methods described herein, exemplary tein from dairy products or from plant juice containing pro sorbable natural products include, but are not limited to, tein) from the non-Sorbable Sugars, fats, oils and other com proteins, Stiviol glucosides, proanthocyanidins, flavan-3-ols ponents of conventional plant extracts (or milk products). (catechins and catechin gallates), hydrolyzable tannins (gal These methods also provide for the immobilization of these lotannins and elagitannins), phlorotannins, gingerols, ses sorbable natural products on the healthy, nutritious, and low quiterpene lactones, Sulforaphane, isothiocyanates, antho Sugar food matrix provided by the ingestible Sorbing material, cyanins, resveratrol, quercetin and caffeine. In some e.g., when in the form of a ground edible plant material. embodiments, the Sorbable natural product is a phenolic com 0004 Disclosed herein, in one aspect, is a method of pound Such as a polyphenol selected from the group consist obtaining natural products from a comestible fluid compris ing of an anthocyanins, a proanthocyanidin, resveratrol, quer 1ng cetin and a catechin. US 2013/0066048 A1 Mar. 14, 2013 0014 For any of the methods described herein, exemplary wiry wattle flour, Mitchell grass flour, nardoo flour, coconut non-Sorbable natural products include, but are not limited to, flour, old man saltbush flour and wangunu flour. carbohydrates (e.g., fructose or glucose), fats and oils. 0020. In some embodiments, the flour is soybean flour, for 0015. Also provided in yet another aspect is a method of example, defatted soybean flour. The use of other ground making an enriched food product comprising a Sorbable natu edible materials such as protein powder, including, but not ral product from plant juice comprising incorporating the limited to, soy protein concentrate, soy protein isolate, wheat enriched substance produced by the methods described bran, oat bran, barley bran, rice bran, milk powder, egg pow herein into an enriched food product. In one embodiment, the der, whey protein, gluten and yeast powder, and cellulose- or enriched food product is a baked good (including, but not chitin-containing material including, but not limited to, non limited to, breads, cookies, muffins, crackers, Scones, cereals soluble vegetable fibers is also contemplated. and bars). In another embodiment, the enriched food product 0021. The enriched substance produced by a method is a beverage (e.g., a smoothie, a water or dairy beverage, or described herein can be separated from the plant liquor by any a soy-based beverage). means known in the art. In one embodiment, the enriched Substance is separated from the plant liquor by a method 0016. In another embodiment, it may be desirable for the selected from the group consisting of centrifugation, filtration concentrated sorbed natural products to be free of the and sedimentation. enriched substance matrix. For example, it may be desirable 0022.
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