Synthesis and glycosidase inhibition of the enantiomer of (-)-steviamine, the first example of a new class of indolizidine alkaloid

Xiang-Guo Hu; Barbara Bartholomew; Robert J Nash; Francis X Wilson; George W J Fleet; Shinpei Nakagawa; Atsushi Kato; Yue-Mei Jia; Renate van Well; Chu-Yi Yu

doi:10.1021/ol1007718

Synthesis and glycosidase inhibition of the enantiomer of (-)-steviamine, the first example of a new class of indolizidine alkaloid

Org Lett. 2010 Jun 4;12(11):2562-5. doi: 10.1021/ol1007718.

Authors

Xiang-Guo Hu¹, Barbara Bartholomew, Robert J Nash, Francis X Wilson, George W J Fleet, Shinpei Nakagawa, Atsushi Kato, Yue-Mei Jia, Renate van Well, Chu-Yi Yu

Affiliation

¹ Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

PMID: 20438104
DOI: 10.1021/ol1007718

Abstract

(+)-Steviamine, the enantiomer of the natural (-)-steviamine, and its corresponding C5 epimer have been synthesized from the D-ribose-derived cyclic nitrone. (-)-Steviamine was found to be the first naturally occurring iminosugar that causes any inhibition of alpha-galactosaminidases.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Alkaloids / pharmacology
Hexosaminidases / antagonists & inhibitors*
Imino Sugars / chemical synthesis*
Imino Sugars / chemistry
Imino Sugars / pharmacology
Indolizidines / chemical synthesis*
Indolizidines / chemistry
Indolizidines / pharmacology
Molecular Structure
Stereoisomerism
Stevia / chemistry

Substances

Alkaloids
Imino Sugars
Indolizidines
steviamine
Hexosaminidases