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(12) Patent Application Publication (10) Pub. No.: US 2014/0128585 A1 Sugimoto Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2014/0128585 A1 Sugimoto Et Al US 2014.0128585A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0128585 A1 Sugimoto et al. (43) Pub. Date: May 8, 2014 (54) FRUCTOSE ABSORPTION INHIBITOR Publication Classification (75) Inventors: Keiichiro Sugimoto, Osaka (JP); Hiroto (51) Int. C. Nakayama, Osaka (JP); Kazuya A613 L/7024 (2006.01) Nakagawa, Osaka (JP); Syuichi A23K L/I6 (2006.01) Hayashi, Osaka (JP) A2.3L I/30 (2006.01) (52) U.S. C. (73) Assignee: Nagaoka Perfumery Co., Ltd., Osaka CPC ........... A6 IK3I/7024 (2013.01); A23L I/3002 (JP) (2013.01); A23K 1/1612 (2013.01) USPC ......................................................... 536/18.1 (21) Appl. No.: 14/130,104 PCT Fled: Jul. 6, 2012 (22) (57) ABSTRACT (86) PCT NO.: S371 (c)(1), A fructose absorption inhibitor according to the present (2), (4) Date: Dec. 30, 2013 invention comprises a hydrolyzable tannin as an active ingre dient. The hydrolyzable tannin preferably has a form com (30) Foreign Application Priority Data posed of a gallic acid derivative and/or an elagic acid deriva tive bound to a hydroxy group in glucose via an ester bond, Jul. 7, 2011 (JP) ................................. 2011-151059 and includes elagitannin, gallotannin and so on. US 2014/O128585 A1 May 8, 2014 FRUCTOSE ABSORPTION INHIBITOR of fructose in “The Dietary Reference Intakes for Japanese'. 2010 edition, developed by Ministry of Health, Labour and TECHNICAL FIELD Welfare. 0008 Excess intake of fructose can be a factor causing 0001. The present invention relates to a fructose absorp various diseases other than those mentioned above. That tion inhibitor which inhibits the process of absorbing fructose includes enhancement of oxidative stress in vivo (Non-patent contained in foods and drinks into the body through the small Document 2), glycation of protein (Non-patent Documents 3 intestine to prevent and improve lifestyle-related diseases and 4), calcium deposits in the kidney (Non-patent Document such as obesity, fatty liver, diabetes and the like caused by 5), hyperuricemia (Non-patent Document 6), initiation of fructose intake. insulin resistance (Non-patent Document 7), initiation of car diovascular kidney diseases (Non-patent Document 8), non BACKGROUND ART alcoholic fatty liver disease (NAFLD) (Non-patent Docu ment 9) and the like. 0002 Obesity is a state in which fat accumulates exces 0009 Glycation of protein means generation of AGE (Ad sively in the body. One of the causes offat accumulation in the vanced Glycation End-product) through reactions between body is excess intake of saccharides (carbohydrates). In gen saccharides and proteins in vivo. In the process of the reac eral, when saccharides contained in foods and drinks are tions, cellular aging and denaturation of protein occur. Gen taken into the body, saccharides are digested by digestive erated AGES also react with surrounding proteins and the like enzymes, mainly converted into monosaccharides and and promote denaturation of body tissues and the like. Since absorbed into the body through the intestinal tracts. AGE is involved in aging of capillary blood vessels and the 0003. One kind of monosaccharides, glucose, is digested like, AGE is regarded as one of the causes of cataract, and absorbed, and then metabolized by group of enzymes decrease in kidney function and the like. In particular, AGE is called the glycolytic pathway. Since the metabolism is regu considered to be strongly related to the onset and aggravation lated at the step with phosphofructokinase among these of complications caused by diabetes progression. Fructose enzymes, the fat synthetic pathway is not immediately acti has a strong reducing character. Therefore, there have been vated even if a large amount of glucose is taken. many reports that fructose has much greater glycation power 0004. On the other hand, another kind of the monosaccha than glucose. Methylglyoxal, a by-product in the process of rides, fructose, is metabolized through a pathway bypassing fructose metabolism, is also problematic as a precursor of the step with phosphofructokinase unlike glucose. Therefore, AGE. if fructose is taken in a large amount, fructose rapidly pro 0010 Incidentally, one kind of the saccharides, sugar (su ceeds to the fat synthetic pathway in the liver and generated crose), is decomposed into the glucose and fructose by amy fat accumulates in adipose tissue. Accordingly, the usual lolytic digestive enzymes. When a large amount of Sugar is intake does not cause problems on health and safety, but taken, rapid absorption of glucose leads to Surge in the blood excess intake of fructose increases the risk of causing patho glucose level along with immediate secretion of insulin. Insu logical conditions such as obesity. lin helps to promote the pathway to convert fructose and 0005. In addition, fructose has strong sweetness among glucose into lipid, glycogen synthesis and glucose intake by monosaccharides and has such a property that its Sweetness is adipocytes. Therefore, medical importance is also placed on enhanced as the temperature decreases. Therefore, fructose is Sugar as a Substance causing obesity and the like. widely used as a Sweetener for processed foods such as 0011. However, sugar is the best as a sweetener consider chilled Sweets and soft drinks containing high-fructose corn ing taste, so a large amount of Sugar is consumed for juice, syrup (HFCS) and the consumption has been rapidly increas confectionary, cooking and the like. ing in recent years. 0012. Accordingly, in cases where a large amount of Sugar 0006. It is well known that the excessive intake of such soft is taken, if the absorption of glucose and fructose generated drinks containing high-fructose corn syrup has become a by digestion of sugar into the body can be inhibited, the effect Social problem in each country. Also in Japan, mainly among of reducing the total calorie intake can be expected. However, young males, cases that are called “PET bottle syndrome' or glucose is the most important monosaccharide for mammals “soft drink ketosis” have been increasing, wherein daily biochemically and is the major energy source for various intake of 1 liter or more of soft drink causes ketosis or ketoaci tissues. In particular, the brain usually uses glucose as a sole dosis. Further, diabetes patients have increased concentration energy source. Therefore, it is problematic to strongly inhibit of fructose in the blood or increased excretion of fructose in absorption of glucose in view of safety. the urine. Especially, it has been reported that the high post 0013. On the other hand, as mentioned above, few roles prandial concentration of fructose in the blood correlates with are confirmed about fructose except for a role as a calorie diabetic retinopathy (Non-patent Document 1), which reports Source. Then, less importance is placed on fructose than glu excess intake of fructose can be a cause of diabetic compli cose nutritionally. Therefore, it can be considered that as a cations. preventive measure against obesity and the like in cases 0007 Under such social background, WHO (World where saccharides are taken excessively, the best way is to Health Organization) recommends that the intake of saccha specifically inhibit the process of absorbing fructose through rides added as Sweeteners should not exceed 10% of the total the intestinal tracts into the body. energy intake (Non-patent Document 2). For example, in the 0014 AS conventional knowledge, concerning Substances United States, ADA (American Diabetes Association) warns which specifically inhibit absorption of fructose into the against use of fructose as an alternative to Sucrose in a guide body, an extract of eucalyptus leaves (Patent Document 1), line for medical care for diabetes. Also in Japan, Ministry of several kinds of natural extracts (Patent Document 2), and Health, Labour and Welfare raises analarm overexcess intake glyco-1,3-oxazolidin-2-ones and analogs thereof that have US 2014/O128585 A1 May 8, 2014 been synthesized as analogs of fructose or sorbitol (Non hydrolyzable tannin has an ester bond composed of a Patent Document 10) have been reported. hydroxyl group in a monosaccharide Such as glucose and an 0.015. However, these natural extracts have a weak inhibi ellagic acid derivative and/or a gallic acid derivative. tory activity and need to be used in a large amount. In addi tion, there are problems that it is difficult to maintain the 0031. That is, a fructose absorption inhibitor of the present quality constant since natural extracts are a mixture and that invention includes the following configurations. natural extracts are hard to be added to foods, drinks, animal 0032 (1) A fructose absorption inhibitor containing a feed or the like due to their distinctive tastes. Synthetic sub hydrolyzable tannin as an active component. stances cannot be used for foods and drinks, and safety needs to be strictly verified if they are used for drugs. So it is very 0033 (2) The fructose absorption inhibitor as set forth in difficult to put them to practical use. (1), wherein the hydrolyzable tannin is a compound having an ester bond composed of a hydroxy group in glucose and a PRIOR ART DOCUMENTS gallic acid derivative and/or an elagic acid derivative. Patent Documents 0034 (3) The fructose absorption inhibitor as set forth in (1) or (2), wherein the hydrolyzable tannin is elagitannin 0016 Patent Document 1: Japanese Unexamined Patent having an ester bond composed of hydroxy groups at the 2 Application Publication 2003-160504 and 3-positions or the 4- and 6-positions or at the both posi 0017 Patent Document 2: Japanese Unexamined Patent tions in glucose and at least one hexahydroxydiphenoyl group Application Publication 2009-184992 or valoneoyl group. Non-Patent Documents 0035 (4) The fructose absorption inhibitor as set forth in 0.018 Non-Patent Document 1: T. Kawasaki et al., (1) or (2), wherein the hydrolyzable tannin is gallotannin Metabolism, 53, 583-588 (2004) having an ester bond composed of at least three hydroxy 0019 Non-Patent Document 2: A.
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