7-deoxy-6-epi-castanospermine, a trihydroxyindolizidine alkaloid glycosidase inhibitor from Castanospermum australe

J Nat Prod. 1990 May-Jun;53(3):609-14. doi: 10.1021/np50069a011.

Abstract

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].

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Indolizines*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plants / analysis*

Substances

  • Alkaloids
  • Indolizines
  • 7-deoxycastanospermine
  • Glycoside Hydrolases