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(12) Patent Application Publication (10) Pub. No.: US 2015/0209377 A1 Lin Et Al

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US 20150209377A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2015/0209377 A1 Lin et al. (43) Pub. Date: Jul. 30, 2015 (54) USE OF NOVEL MONOSACCHARIDE-LIKE filed on Sep. 13, 2014, provisional application No. GLYCYLATED SUGAR ALCOHOL 62/054,981, filed on Sep. 25, 2014. COMPOSITIONS FOR DESIGNING AND DEVELOPNG ANT-DABETC DRUGS Publication Classification (71) Applicants: Shi-Lung Lin, Arcadia, CA (US); (51) Int. Cl. Samantha Chang-Lin, Arcadia, CA A613 L/702 (2006.01) (US); Yi-Wen Lin, Arcadia, CA (US); A63L/22 (2006.01) Donald Chang, Arcadia, CA (US) (52) U.S. Cl. CPC ........... A6 IK3I/7012 (2013.01); A61 K3I/221 (72) Inventors: Shi-Lung Lin, Arcadia, CA (US); (2013.01) Samantha Chang-Lin, Arcadia, CA (US); Yi-Wen Lin, Santa Fe Spring, CA (57) ABSTRACT (US); Donald Chang, Cerritos, CA (US) This invention is related to a novel Sugar-like chemical com position and its use for diabetes therapy. Particularly, the (73) Assignees: Shi-Lung Lin, Arcadia, CA (US); present invention teaches the use of monosaccharide-like gly Samantha Chang-Lin, Arcadia, CA cylated Sugar alcohol compounds to block or reduce Sugar (US); Yi-Wen Lin, Arcadia, CA (US); absorption in diabetes patients, so as to prevent the risk of Donald Chang, Arcadia, CA (US) hyperglycemia symptoms. Glycylation of Sugar alcohols is a totally novel reaction that has never been reported before. (21) Appl. No.: 14/585,978 Therefore, the novelty of the present invention is that for the first time glycylated Sugar alcohols not only was found but (22) Filed: Dec. 30, 2014 also was found to be useful for treating Diabetes mellitus. In addition, the present invention teaches a method for produc Related U.S. Application Data ing these glycylated Sugar alcohols. In Sum, the present inven tion includes not only a kind of novel Sugar-like chemical (63) Continuation-in-part of application No. 14/457.829, compositions and its use for treating diabetes but also a state filed on Aug. 12, 2014. of-the-art protocol and methodology for producing Such a (60) Provisional application No. 61/931,650, filed on Jan. novel composition via glycylation of Sugars and Sugar alco 26, 2014, provisional application No. 62/050,107, hols. Patent Application Publication Jul. 30, 2015 Sheet 1 of 6 US 2015/0209377 A1 F.G. 1 Sample Nanne injection Waturne: 50, Wai Number Channed UV VS : Sangie type: Wavelength 26 Control Program, miR302.3x6mi-fows 20min ByTime Bandwidth: 3. Quantif Method Default 2. C. Processing fiftition acior 1880 Recording line: Sf2020A: Sample Weight 1,300 Run Tine (min); 9.8 Sanpie Annotint 18000 BW WS 1 WWL-260 min: m Peak Nare height Area ReArea. Anot At Ain % 2, 3 ra. DGGf GG 3.25 O339 2.78 4.25 3. MGG 2,225 22 82a 5431 88C 300 800 Patent Application Publication Jul. 30, 2015 Sheet 2 of 6 US 2015/0209377 A1 FIG. 2A glycerol (glycerin) glycine / Ya n "st- C-C 1-monoglycylglycerin (1-MGG) Of t c aw to-CKC-O-C C kits 3-monoglycylglycerin (3-MGG) Of C f cf. -e-q's* N 2-monoglycylglycero (2-MGG) Patent Application Publication Jul. 30, 2015 Sheet 3 of 6 US 2015/0209377 A1 FG. 2B glycerol (glycerin) glycine th C. ?h c. + n x -ca-C, th (n - 2 or 3) Glycylation of Sugar Alcohols (i.e. glycerol) t c re * \t -o-Cl ch:-0-C C is diglycylglycerol (DGG) Of FG. 2C t -- M Cix M triglycylglyceride dCast (TGG)TGG g: a’ c C o Nig-- Patent Application Publication Jul. 30, 2015 Sheet 4 of 6 US 2015/0209377 A1 Patent Application Publication Jul. 30, 2015 Sheet 5 of 6 US 2015/0209377 A1 s O O. O. 3 f f t s an S (p/au) Soon pools Patent Application Publication Jul. 30, 2015 Sheet 6 of 6 US 2015/0209377 A1 shas se o O O O if o f O tr ef ey ra N an in (ue?) Augie/W Apog US 2015/0209377 A1 Jul. 30, 2015 USE OF NOVEL MONOSACCHARDE-LIKE may not be treated with insulin, depending on the pathologi GLYCYLATED SUGAR ALCOHOL cal causes of insulin resistance. COMPOSITIONS FOR DESIGNING AND 0004 Current medications for type-II DM can be catego DEVELOPING ANT-DABETC DRUGS rized into five groups: first, drugs increase insulin production in pancreas. Such as Sulfonylureas, Meglitinides and Stita PRIORITY gliptin; second, drugs decrease Sugar production in liver, Such 0001. The present invention claims priority to the U.S. as Metformin; third, drugs increase Sugar excretion via urine, Provisional Application Ser. No. 61/931,650 filed on Jan. 26, Such as Canagliflozin, forth, drugs reduce insulin resistance 2014, which was entitled “Composition and Formulation of in fat tissues and muscles, such as Thiazolidinediones; and Sugar Alcohol-Based Complexes for Delivering Nucleic last, drugs delay and/or reduce Sugar absorption in intestines, Acid-Based Drugs. In Vitro and InVivo”. The present inven Such as alpha-glucosidase inhibitors. However, due to the tion also claims priority to the U.S. Provisional Application kinetic properties of these drugs directed against certain natu Ser. No. 62/050,107 filed on Sep. 13, 2014, which was ral metabolic pathways of the body, they often present various entitled “Novel Monosaccharide-like Glycylated Sugar Alco degrees of side effects, including hypoglycemia (Sulfony hol Compositions useful for Diabetes Therapy'. The present lureas, Meglitinides, Stitagliptin and alpha-glucosidase invention further claims priority to the U.S. patent application inhibitors), kidney failure (Metformin and Canagliflozin), Ser. No. 14/457,829 filed on Aug. 12, 2014, entitled “Novel heart failure (Metformin and Thiazolidinediones), gas Sugar Alcohol-Based Compositions for Delivering Nucleic trointestinal problems (Metformin and alpha-glucosidase Acid-Based Drugs. In Vivo and In Vitro’. The present appli inhibitors), edema and anemia (Thiazolidinediones). In some cation is a continuation-in-part (CIP) application of the U.S. worst cases, death has been reported. patent application Ser. No. 14/457,829 filed on Aug. 12, 2014, 0005 To prevent the lethal problems of kidney and heart entitled “Novel Sugar Alcohol-Based Compositions for failure, the best way of treating type-II diabetes is to delay and Delivering Nucleic Acid-Based Drugs In Vivo and In Vitro'. reduce Sugar absorption in intestines; yet, without losing the which are hereby all incorporated by reference as if fully set Supply of energy. The current anti-diabetic drugs of this kind forth herein. Such as alpha-glucosidase inhibitors function through inhibi tion of intestinal enzymes that convert carbohydrates into FIELD OF INVENTION monosaccharides and hence can block Sugar uptake in intes 0002 This invention generally relates to a novel sugar-like tines. Nevertheless, the undigested carbohydrates may then chemical composition and its use for diabetes therapy. Par interact with colon bacteria to cause gastrointestinal prob ticularly, the present invention teaches the use of monosac lems, such as flatulence and diarrhea. From the beneficial charide-like modified Sugar alcohol compositions to replace view, this side effect may help to reduce obesity; yet, the Sugars for absorption in patients, so as to treat diabetes mel drawback is that blocking Sugar uptake also means loss of litus. In order to mimic monosaccharides, these novel Sugar energy Supply to the body. As a result, overdose of alpha alcohol compositions are modified by a reaction called gly glucosidase inhibitors can lead to acute hypoglycemia in cylation and turned into glycylated Sugar alcohols. As a result, diabetes patients. the novelty of the present invention is to use these glycylated 0006 Recently, it is further noted that the use of sugars and Sugar alcohols for reducing the Sugar uptake in human intes Sugar Substitutes such as artificial Sweeteners may worsen the tines, Subsequently preventing the hyperglycemia symptoms Sugar intolerance conditions of Diabetes mellitus in patients of diabetes patients after meals. In addition, the present inven (Suez et al., (2014) Nature in press, doi:10.1038/na tion teaches for the first time that chemical compounds like ture13793). Sugar alcohols and Sugars can be modified by glycylation to 0007. In sum, there is currently no safe drug agent or sugar reduce their pathological effects in diabetes. Therefore, the substitute that can treat type-II DM while still maintaining the present invention includes not only a kind of novel Sugar-like Supply of normal body energy. Therefore, it is highly desir chemical compositions and its use for treating diabetes but able to have a novel anti-diabetic composition that is able not also a state-of-the-art protocol and methodology for produc only to reduce Sugar absorption in intestines but also to pro ing Such a novel composition via glycylation. vide an alternative energy source to the body. BACKGROUND SUMMARY OF THE INVENTION 0003 Diabetes mellitus (DM), also known as diabetes, is a group of metabolic diseases that cause long-lasting hyperg 0008 Stem cells are treasure boxes containing various lycemia symptoms in humans as well as Some other mam effective ingredients useful for designing and developing cos mals, such as mice. These hyperglycemia symptoms include medical, pharmaceutical and therapeutic drugs and/or appli high blood Sugar levels (i.e. >140 mg/dL), frequenturination, cations, including, but not limited by, inducing and enhancing increased thirst and hunger, and more severely diabetic body cell/tissue/organ regeneration, repairing/healing dam ketoacidosis and hyperosmolar coma. Long-term hypergly aged tissues and organs, rejuvenating aged cells/tissues?or cemia often leads to heart diseases, stroke, kidney failure, gans, treating degenerative diseases (i.e. cancers, diabetes, ulcers in extremities, eye damages and obesity. There are two osteoporosis, Parkinson's and Alzheimer's diseases ..
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  • Supplementary File

    Supplementary File

    Supplementary File Chemical composition, bioactive compounds and antioxidant activity of two wild edible mushrooms Armillaria mellea and Macrolepiota procera from two countries (Morocco and Portugal) El Hadi Erbiai 1,2, Luís Pinto da Silva 2 , Rabah Saidi 1, Zouhaire Lamrani 1, Joaquim C.G. Esteves da Silva 2, Abdelfettah Maouni 1,* 1 Biology, Environment, and Sustainable Development Laboratory, Higher School of Teachers (ENS), Abdelmalek Essaâdi University, Tetouan, Morocco; [email protected] (E.H.E.); [email protected] (F.E.E); [email protected] (R.S.); [email protected] (Z.L), [email protected] (A.M.) 2 Research Centre in Chemistry (CIQUP), DGAOT, Faculty of Sciences, University of Porto, Portugal; [email protected] (L.P.S.); [email protected] (J.C.G.E.S.) SUPPLEMENTAL INFORMATION Supplemental experimental methodology 1.1. Spectrophotometric Determination of Bioactive Compounds Total Phenolic Content (TFC) was determined by Folin-Ciocalteu assay [1]. One ml of extract methanolic solution (5 mg/ml) was mixed with 5 ml of Folin–Ciocalteu reagent (previously diluted with distilled water 1:10, v/v) and 4 ml of sodium carbonate solution (7,5%). The tubes were vortex mixed for 15 s and allowed to stand for 30 min at 40 °C in the dark. Then, the absorbance of the solution was measured at 765 nm against the blank. Gallic acid was used to obtain the standard curve (0-250 µg/ml), and the results were mean values ± standard deviations (SD) and expressed as milligrams of gallic acid equivalents (GAE) per gram of dried methanolic extract (dme).