7-deoxy-6-epi-castanospermine, a trihydroxyindolizidine alkaloid glycosidase inhibitor from Castanospermum australe.
A new indolizidine alkaloid has been isolated from the seeds of Castanospermum [1] australe and identified as 7-deoxy-6-epi-castanospermine by ms and 1H- and 13C-nmr spectroscopy. The alkaloid is the first trihydroxylated indolizidine to be isolated from this plant and may represent an intermediate in the biosynthetic pathway to the tetrahydroxy-indolizidines and -pyrrolizidines. It inhibits amyloglucosidase and yeast alpha-glucosidase but is significantly less active as a glycosidase inhibitor than its isomer swainsonine [2] and the tetrahydroxylated alkaloids castanospermine [3], 6-epi-castanospermine [4], and australine [5].
Western Regional Research Center, USDA, Albany, California 94710.
R J
RJ
Molyneux
J E
JE
Tropea
A D
AD
Elbein
D000470:Alkaloids / Q000302:isolation & purification* / Q000494:pharmacology; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D007212:Indolizines; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010944:Plants / Q000032:analysis*
D000470:Alkaloids; D007212:Indolizines; C065752:7-deoxycastanospermine; D006026:Glycoside Hydrolases