[논문]New Glucosidase Inhibitors from an Ayurvedic Herbal Treatment for Type 2 Diabetes: Structures and Inhibition of Human Intestinal Maltase-Glucoamylase with Compounds from Salacia reticulata

Sim, Lyann; Jayakanthan, Kumarasamy; Mohan, Sankar; Nasi, Ravindranath; Johnston, Blair D.; Pinto, B. Mario; Rose, David R.

doi:10.1021/bi9016457

New Glucosidase Inhibitors from an Ayurvedic Herbal Treatment for Type 2 Diabetes: Structures and Inhibition of Human Intestinal Maltase-Glucoamylase with Compounds from Salacia reticulata

Biochemistry, v.49 no.3, 2010년, pp.443 - 451

Sim, Lyann (Ontario Cancer Institute and Department of Medical Biophysics, University of Toronto, 101 College Street, Toronto, ON, M5G 1L7 Canada) , Jayakanthan, Kumarasamy (Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6 Canada) , Mohan, Sankar (Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6 Canada) , Nasi, Ravindranath (Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6 Canada) , Johnston, Blair D. (Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6 Canada) , Pinto, B. Mario (Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, BC, V5A 1S6 Canada) , Rose, David R. (Department of Biology, University of Waterloo, 200 University Avenue West, Waterloo, ON, N2L 3G1 Canada)

Abstract ▼ AI-Helper

An approach to controlling blood glucose levels in individuals with type 2 diabetes is to target α-amylases and intestinal glucosidases using α-glucosidase inhibitors acarbose and miglitol. One of the intestinal glucosidases targeted is the N-terminal catalytic domain of maltase-glucoamylase (ntMGAM), one of the four intestinal glycoside hydrolase 31 enzyme activities responsible for the hydrolysis of terminal starch products into glucose. Here we present the X-ray crystallographic studies of ntMGAM in complex with a new class of α-glucosidase inhibitors derived from natural extracts of Salacia reticulata, a plant used traditionally in Ayuverdic medicine for the treatment of type 2 diabetes. Included in these extracts are the active compounds salacinol, kotalanol, and de-O-sulfonated kotalanol. This study reveals that de-O-sulfonated kotalanol is the most potent ntMGAM inhibitor reported to date (Ki = 0.03 μM), some 2000-fold better than the compounds currently used in the clinic, and highlights the potential of the salacinol class of inhibitors as future drug candidates.Graphic AbstractACS Electronic Supporting Info

참고문헌 (47)

Diabetes Care Holman R. R. 960 22 1999 10.2337/diacare.22.6.960

상세보기
Drugs Krentz A. J. 385 65 2005 10.2165/00003495-200565030-00005

상세보기
Drugs Mooradian A. D. 19 57 1999 10.2165/00003495-199957010-00003

상세보기
Drugs Scheen A. J. 933 63 2003 10.2165/00003495-200363100-00002

상세보기
Glycobiology Asano N. 93 13 2003 10.1093/glycob/cwg090

상세보기
Iminosugars as glycosidase inhibitors: Nojirimycin and beyond Stuttz A. E. 1999
The Chemistry and Pharmacology of Ceylon and Indian Medicinal Plants Chandrasena J. P. C. 1935
Medicinal Plants Used in Ceylon-Part 1 Jayaweera D. M. A. 1981
Indian Medicinal Plants: A compendium of 500 species Vaidyartanam P. S. 1993
J. Tradit. Med. Matsuda H. 145 22 2005
Phytother. Res. Serasinghe S. 205 4 1990 10.1002/ptr.2650040511

상세보기
J. Food Hyg. Soc. Jpn. Shimoda H. 198 20 1999 10.3358/shokueishi.40.3_198

상세보기
J. Ethnopharmacol. Jayawardena M. H. S. 215 97 2005 10.1016/j.jep.2004.10.026

상세보기
J. Health Sci. Im R. 645 54 2008 10.1248/jhs.54.645

상세보기
Tetrahedron Lett. Muraoka O. 7315 49 2008 10.1016/j.tetlet.2008.10.036

상세보기
Tetrahedron Lett. Yoshikawa M. 8367 38 1997 10.1016/S0040-4039(97)10270-2

상세보기
Chem. Pharm. Bull. Yoshikawa M. 1339 46 1998 10.1248/cpb.46.1339

상세보기
Biochim. Biophys. Acta Semenza G. 487 96 1965 10.1016/0005-2787(65)90565-4

상세보기
The Metabolic Basis of Inherited Disease Semenza G. 2001
FEBS J. Rossi E. J. 2673 273 2006 10.1111/j.1742-4658.2006.05283.x

상세보기
J. Org. Chem. Nasi R. 6172 73 2008 10.1021/jo800855n

상세보기
Carbohydr. Res. Mohan S. 1551 342 2007 10.1016/j.carres.2007.05.014

상세보기
Biochemistry Li C. 3347 44 2005 10.1021/bi048334e

상세보기
Eur. J. Clin. Invest. Bischoff H. 3 24 3 1994
J. Nutr. Madar Z. 2023 119 1989 10.1093/jn/119.12.2023

상세보기
Drugs Toeller M. 13 44 3 1992 10.2165/00003495-199200443-00003

상세보기
Nutrient Drug Interactions Meckling K. A. 2006 10.1201/9781420019131
J. Mol. Biol. Sim L. 782 375 2008 10.1016/j.jmb.2007.10.069

상세보기
J. Org. Chem. Johnston B. D. 1111 71 2006 10.1021/jo052252u

상세보기
J. Am. Chem. Soc. Jayakanthan K. 5621 131 2009 10.1021/ja900867q

상세보기
J. Org. Chem. Ghavami A. 2312 66 2001 10.1021/jo001444g

상세보기
Methods Enzymol. Otwinowski Z. 307 276 1997 10.1016/S0076-6879(97)76066-X
Acta Crystallogr. Murshudov G. N. 240 53 1997
Acta Crystallogr. Emsley P. 2126 60 2004
Acta Crystallogr. Schuttelkopf A. W. 1355 60 2004
Acta Crystallogr. Perrakis A. 1445 57 2001
J. Org. Chem. Nasi R. 180 72 2007 10.1021/jo061944v

상세보기
J. Nutr. Quezada-Calvillo R. 685 138 2008 10.1093/jn/138.4.685

상세보기
J. Biol. Chem. Lovering A. L. 2105 280 2005 10.1074/jbc.M410468200

상세보기
Biochemistry Wen X. 6729 44 2005 10.1021/bi0500426

상세보기
Curr. Opin. Chem. Biol. Vocadlo D. J. 539 12 2008 10.1016/j.cbpa.2008.05.010

상세보기
Iminosugars as glycosidase inhibitors: Nojirimycin and beyond Withers S. G. 188 1999
Biochemistry Mosi R. 17192 37 1998 10.1021/bi981109a

상세보기
Biochemistry Berland C. R. 10153 34 1995 10.1021/bi00032a008

상세보기
J. Org. Chem. Liu H. 6562 72 2007 10.1021/jo071045m

상세보기
J. Org. Chem. Liu H. 3007 71 2006 10.1021/jo052539r

상세보기
Drugs Chehade J. M. 95 60 2000 10.2165/00003495-200060010-00006

상세보기

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New Glucosidase Inhibitors from an Ayurvedic Herbal Treatment for Type 2 Diabetes: Structures and Inhibition of Human Intestinal Maltase-Glucoamylase with Compounds from Salacia reticulata

Abstract ▼ AI-Helper

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