Synthesis and elucidation of absolute stereochemistry of salaprinol, another thiosugar sulfonium sulfate from the ayurvedic traditional medicine Salacia prinoides

Tetrahedron

Volumn 64, Issue 43, 2008, Pages 10080-10086

  Tanabe, Genzoh ^a   Sakano, Mika ^a   Minematsu, Toshie ^a   Matusda, Hisashi ^b   Yoshikawa, Masayuki ^b   Muraoka, Osamu ^a  

^a KINKI UNIVERSITY   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Glucosidase inhibitor; epi Salaprinol; Salacia prinoides; Salaprionol; Sulfonium sulfate

Indexed keywords

1,4 DIDEOXY 1,4 EPITHIO DEXTRO ARABINITOL; 2 O BENZYLGLYCEROL 1,3 CYCLIC SULFATE; ANTIDIABETIC AGENT; ARABINITOL; EPISALAPRINOL; SALAPRINOL; SULFATE; SULFONIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AYURVEDA; CARBON NUCLEAR MAGNETIC RESONANCE; DIABETES MELLITUS; DRUG ISOLATION; DRUG SYNTHESIS; INDIA; PLANT ROOT; PLANT STEM; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SALACIA; SALACIA PRINOIDES; SOUTHEAST ASIA; SRI LANKA; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 50849123767     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.08.010     Document Type: Article

References (32)

1. Yoshikawa M., Xu F., Morikawa T., Pongpiriyadacha Y., Nakamura S., Asao Y., Kumahara A., and Matsuda H. Chem. Pharm. Bull. 55 (2007) 308
2. Yoshikawa M., Nakamura S., Ozaki K., Kumahara A., Morikawa T., and Matsuda H. J. Nat. Prod. 70 (2007) 210
3. Yoshikawa M., Wang T., Morikawa T., Xie H., and Matsuda H. Chem. Pharm. Bull. 55 (2007) 1308
4. Zhang H., Matsuda H., Kumahara A., Ito Y., Nakamura S., and Yoshikawa M. Bioorg. Med. Chem. Lett. 17 (2007) 4972
5. Matsuda H., Yoshikawa M., Morikawa T., Tanabe G., and Muraoka O. J. Trad. Med. 22 (2005) 145
6. Yoshikawa M., Nishida N., Shimoda H., Takada M., Kawahara Y., and Matsuda H. Yakugaku Zasshi 121 (2001) 371
7. Yoshikawa M., Murakami T., Shimada H., Matsuda H., Yamahara J., Tanabe G., and Muraoka O. Tetrahedron Lett. 38 (1997) 8367
8. Yoshikawa M., Murakami T., Yashiro K., and Matsuda H. Chem. Pharm. Bull. 46 (1998) 1339
9. Yoshikawa M., Morikawa T., Matsuda H., Tanabe G., and Muraoka O. Bioorg. Med. Chem. 10 (2002) 1547
10. Matsuda H., Murakami T., Yashiro K., Yamahara J., and Yoshikawa M. Chem. Pharm. Bull. 47 (1999) 1725
11. Yoshikawa M., Pongpiriyadacha Y., Kishi A., Kageura T., Wang T., Morikawa T., and Matsuda H. Yakugaku Zasshi 123 (2003) 871
12. Yuasa H., Takada J., and Hashimoto H. Tetrahedron Lett. 41 (2000) 6615
13. Ghavami A., Johnston B.D., and Pinto B.M. J. Org. Chem. 66 (2001) 2312
14. Muraoka O., Ying S., Yoshikai K., Matsuura Y., Yamada E., Minematsu T., Tanabe G., Matsuda H., and Yoshikawa M. Chem. Pharm. Bull. 49 (2001) 1503
15. Ghavami A., Sadalapure K.S., Johnston B.D., Lobera M., Snider B.B., and Pinto B.M. Synlett (2003) 1259
16. Muraoka O., Yoshikai K., Takahashi H., Minematsu T., Lu G., Tanabe G., Wang T., Matsuda H., and Yoshikawa M. Bioorg. Med. Chem. 14 (2006) 500
17. Tanabe G., Yoshikai K., Hatanaka T., Yamamoto M., Shao Y., Minematsu T., Muraoka O., Wang T., Matsuda H., and Yoshikawa M. Bioorg. Med. Chem. 15 (2007) 3926
18. Mohan S., and Pinto B.M. Carbohydr. Res. 342 (2007) 1551 and referenced cited therein
19. Ratnasooriya W.D., Jayakody J.R.A.C., and Premakumara G.A.S. Braz. J. Med. Biol. Res. 36 (2003) 931
20. Wolf B.W., and Weisbrode S.E. Food Chem. Toxicol. 41 (2003) 867
21. Flammang A.M., Erexson G.L., Mecchi M.S., and Murli H. Food Chem. Toxicol. 44 (2006) 1868
22. Kitabayashi H., Nakamura C., Katsuta K., Horii A., Momizo I., Takano J., Yoshikawa M., Muraoka O., Saito Y., Saito M., and Koikeda T. J. Nutr. Food 10 (2007) 23
23. Yoshikawa M., Xu F., Nakamura S., Wang T., Matsuda H., Tanabe G., and Muraoka O. Heterocycles 75 (2008) 1397
24. Hronowski L.J.J., Szarek W.A., Hay G.W., Krebs A., and Depew W.T. Carbohydr. Res. 190 (1989) 203
25. Verkade P.E., van der Lee J., and Meerburg W. Recl. Trav. Chim. Pays-Bas 56 (1937) 613
26. Hurd C.D., Mack C.O., Filachione E.M., and Sowden J.C. J. Am. Chem. Soc. 59 (1937) 1952
27. Suemune H., Mizuhara Y., Akita H., and Sakai K. Chem. Pharm. Bull. 34 (1986) 3440
28. Murata M., Terao Y., Achiwa K., Nishio T., and Seto K. Chem. Pharm. Bull. 37 (1989) 2670
29. Cassel S., Debaig C., Benvegnu T., Chaimbault P., Lafosse M., Plusquellec D., and Rollin P. Eur. J. Org. Chem. (2001) 875
30. Ray III W.C., and Grinstaff M.W. Macromolecules 36 (2003) 3557
31. Wang Q., and Löennberg H. J. Am. Chem. Soc. 128 (2006) 10716
32. Hronowski L.J.J., Szarek W.A., Hay G.W., Krebs A., and Depew W.T. Carbohydr. Res. 193 (1989) 91