Synthesis and glycosidase inhibition of the enantiomer of (-)-steviamine, the first example of a new class of indolizidine alkaloid.
(+)-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.
Hu
Xiang-Guo
XG
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.
Bartholomew
Barbara
B
Nash
Robert J
RJ
Wilson
Francis X
FX
Fleet
George W J
GW
Nakagawa
Shinpei
S
Kato
Atsushi
A
Jia
Yue-Mei
YM
van Well
Renate
R
Yu
Chu-Yi
CY
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006596:Hexosaminidases / Q000037:antagonists & inhibitors*; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D054836:Indolizidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013237:Stereoisomerism; D036625:Stevia / Q000737:chemistry
D000470:Alkaloids; D050111:Imino Sugars; D054836:Indolizidines; C551370:steviamine; D006596:Hexosaminidases