Role of the side chain stereochemistry in the α-glucosidase inhibitory activity of kotalanol, a potent natural α-glucosidase inhibitor

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 7, 2011, Pages 2252-2262

  Xie, Weijia ^a,b   Tanabe, Genzoh ^a   Matsuoka, Kanjyun ^a   Amer, Mumen F A ^a   Minematsu, Toshie ^a   Wu, Xiaoming ^b   Yoshikawa, Masayuki ^c   Muraoka, Osamu ^a  

^a KINKI UNIVERSITY   (Japan)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

^c KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Glucosidase inhibitor; Kotalanol; Salacia; SAR study; Selective inhibition

Indexed keywords

ACARBOSE; ALPHA GLUCOSIDASE; ALPHA GLUCOSIDASE INHIBITOR; KOTALANOL; NEOKOTALANOL; NEOPONKORANOL; NEOSALACINOL; NEOSALAPRINOL; OLIGO 1,6 GLUCOSIDASE; PONKORANOL; SALACINOL; SALAPRINOL; SUCRASE; UNCLASSIFIED DRUG; VOGLIBOSE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ISOLATION; ENZYME INHIBITION; NONHUMAN; RAT; SALACIA; STEREOCHEMISTRY;

ALPHA-GLUCOSIDASES; ENZYME INHIBITORS; MOLECULAR STRUCTURE; MONOSACCHARIDES; PLANT EXTRACTS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATES;

EID: 79953186418     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.02.028     Document Type: Article

References (53)

1. T.D. Heightman, and A.T. Vasella Angew. Chem., Int. Ed. 38 1999 750
2. V.V. Krasikov, D.V. Karelov, and L.M. Firsov Biochemistry (Moscow) 66 2001 267
3. V.H. Lillelund, H.H. Jensen, X. Liang, and M. Bols Chem. Rev. 102 2002 515
4. A. Herscovics B.M. Pinto, D.H.R. Barton, K. Nakanishi, O. Meth-Cohn, Comprehensive Natural Products Chemistry 1999 Elsevier UK
5. J.D. McCarter, and S.G. Withers Curr. Opin. Struct. Biol. 4 1994 885
6. H.D. Ly, and S.G. Withers Annu. Rev. Biochem. 68 1999 487
7. P. Hollander, X. Pi-Sunyer, and R.E. Coniff Diabetes Care 20 1997 248
8. L. Scott, and C.M. Spencer Drugs 59 2000 521
9. A.Y.Y. Cheng, and R.G. Josse Drug Discovery Today 2004 201
10. A. Mitrakou, N. Tountas, A.E. Raptis, R.J. Bauer, H. Shulz, and S.A. Raptis Diabet. Med. 15 1998 657
11. C.P. Kordik, and A.B. Reitz J. Med. Chem. 42 1999 181
12. F.M. Platt, and T.D. Butters Exp. Rev. Mol. Med. 2000 1
13. T.D. Butters, R.A. Dwek, and F.M. Platt Curr. Top. Med. Chem. 3 2003 561
14. M. Takeuchi, K. Kamata, M. Yoshida, Y. Kameda, and K. Matsui J. Biochem. 108 1990 42
15. T.D. Butters, R.A. Dwek, and F.M. Platt Glycobiology 15 2005 43
16. Iminosugars: Recent Insights into Their Bioactivity and Potential As Therapeutic Agents O.R. Martin, P. Compain, Current Topics in Medical Chemistry Bentham Vol. 3 2003 Hilversum Netherland Issue 5
17. M.G. Szczepina, B.D. Johnston, Y. Yuan, B. Svensson, and B.M. Pinto J. Am. Chem. Soc. 126 2004 12458
18. A.E. Stutz Iminosugars as Glycosidase Inhibitors 1999 Wiley-VCH New York
19. M. Yoshikawa, T. Murakami, H. Shimada, H. Matsuda, J. Yamahara, G. Tanabe, and O. Muraoka Tetrahedron Lett. 38 1997 8367
20. M. Yoshikawa, T. Morikawa, H. Matsuda, G. Tanabe, and O. Muraoka Bioorg. Med. Chem. 10 2002 1547
21. M. Yoshikawa, T. Murakami, K. Yashiro, and H. Matsuda Chem. Pharm. Bull. 46 1998 1339
22. M. Yoshikawa, F. Xu, S. Nakamura, T. Wang, H. Matsuda, G. Tanabe, and O. Muraoka Heterocycles 75 2008 1397
23. Y. Minami, C. Kuriyama, K. Ikeda, A. Kato, K. Takebayashi, I. Adachi, G.W.J. Fleet, A. Kettawan, T. Okamoto, and N. Asano Bioorg. Med. Chem. 16 2008 2734
24. G. Tanabe, W. Xie, A. Ogawa, C. Cao, T. Minematsu, M. Yoshikawa, and O. Muraoka Bioorg. Med. Chem. Lett. 19 2009 2195
25. S. Ozaki, H. Oe, and S. Kitamura J. Nat. Prod. 71 2008 981
26. H. Oe, and S. Ozaki Biosci. Biotechnol. Biochem. 72 2008 1962
27. O. Muraoka, W. Xie, G. Tanabe, F.A.M. Amer, T. Minematsu, and M. Yoshikawa Tetrahedron Lett. 49 2008 7315
28. W. Xie, G. Tanabe, J. Akaki, T. Morikawa, K. Ninomiya, T. Minematsu, M. Yoshikawa, X. Wu, and O. Muraoka Bioorg. Med. Chem. 19 2011 2014
29. Recent review relevant to the present work: S. Mohan, and B.M. Pinto Carbohydr. Res. 342 2007 1551
30. G. Tanabe, K. Yoshikai, T. Hatanaka, M. Yamamoto, Y. Shao, T. Minematsu, O. Muraoka, T. Wang, H. Matsuda, and M. Yoshikawa Bioorg. Med. Chem. 15 2007 3926
31. R. Nasi, L. Sim, D.R. Rose, and B.M. Pinto J. Org. Chem. 72 2007 180
32. R. Nasi, B.O. Patrick, L. Sim, D.R. Rose, and B.M. Pinto J. Org. Chem. 73 2008 6172
33. G. Tanabe, M. Sakano, T. Minematsu, H. Matusda, M. Yoshikawa, and O. Muraoka Tetrahedron 64 2008 10080
34. G. Tanabe, T. Hatanaka, T. Minematsu, H. Matsuda, M. Yoshikawa, and O. Muraoka Heterocycles 79 2009 1093
35. L. Sim, K. Jayakanthan, S. Mohan, R. Nasi, B.D. Johnston, B.M. Pinto, and D.R. Rose Biochemistry 49 2010 443
36. S. Mohan, K. Jayakanthan, R. Nasi, D.A. Kuntz, D.R. Rose, and B.M. Pinto Org. Lett. 12 2010 1088
37. R. Eskandari, D.A. Kuntz, D.R. Rose, and B.M. Pinto Org. Lett. 12 2010 1632 and references cited therein
38. K. Jayakanthan, S. Mohan, and B.M. Pinto J. Am. Chem. Soc. 131 2009 5621
39. O. Muraoka, W. Xie, S. Osaki, A. Kagawa, G. Tanabe, M.F.A. Amer, T. Minematsu, T. Morikawa, and M. Yoshikawa Tetrahedron 66 2010 3717
40. F. Matsuda, and S. Terashima Tetrahedron 44 1988 4721
41. J.K. Cha, W.J. Christ, and Y. Kishi Tetrahedron 40 1984 2247
42. J.K. Cha, and N.S. Kim Chem. Rev. 95 1995 1761
43. K.B. Sharpless, W. Bmberg, M. Beller, H. Chen, J. Hartung, Y. Kawanami, D. Lubben, E. Manoury, and Y. Ogino J. Org. Chem. 56 1991 4585
44. Z.M. Wang, K. Kakiuchi, and K.B. Sharpless J. Org. Chem. 59 1994 6895
45. L. Wang, and K.B. Sharpless J. Am. Chem. Soc. 19 1992 7569
46. S.J. Angyal Carbohydr. Res. 126 1984 15
47. K. Hattori, H. Sajiki, and K. Hirota Tetrahedron 57 2001 2109 and references cited therein
48. Y. Gao, and K.B. Sharpless J. Am. Chem. Soc. 110 1988 7358
49. B.M. Kim, and K.B. Sharpless Tetrahedron Lett. 30 1989 566
50. B.B. Lohray Synthesis 1992 1035
51. Y. Moritoh, K. Takeuchi, and M. Hazama J. Pharmacol. Exp. Ther. 329 2009 669
52. B.K. Samulitis, T. Goda, S.M. Lee, and O. Koldovsky Drugs Exp. Clin. Res. 13 1987 517
53. M. Kessler, O. Acuto, C. Storelli, H. Murer, M. Mueller, and G. Semenza Biochim. Biophys. Acta 506 1978 136