Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid

Stephen V. Evans, Alison R. Hayman, Linda E. Fellows, Tony Kung Ming Shing, Andrew E.Derome, George W.J. Fleet

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn. Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor free fagomine [1,2,5-trideoxy-1,5-imino-D-arabinohexitol] (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.

Original languageEnglish
Pages (from-to)1461-1464
Number of pages4
JournalTetrahedron Letters
Volume26
Issue number11
DOIs
Publication statusPublished - 1985 Jan 1
Externally publishedYes

Fingerprint

Glycoside Hydrolases
Glucosides
Alkaloids
Fabaceae
Piperidines
Glycosides
Seed
Seeds
Enzymes
piperidine
hexitol
fagomine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Lack of glycosidase inhibition by, and isolation from xanthocercis zambesiaca (leguminosae) of, 4-O-(β-D-glucopyranosyl)-fagomine [1,2,5-trideoxy-4-O-(β-D-glucopyranosyl)-1,5-imino-D-arabino-hexitol], a novel glucoside of a polyhydroxylated piperidine alkaloid. / Evans, Stephen V.; Hayman, Alison R.; Fellows, Linda E.; Shing, Tony Kung Ming; E.Derome, Andrew; Fleet, George W.J.

In: Tetrahedron Letters, Vol. 26, No. 11, 01.01.1985, p. 1461-1464.

Research output: Contribution to journalArticle

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abstract = "A COSY spectrum has been used to determine the position of inter-residue linkage in 4-O-(β-D-glucopyranosyl) fagomine (1) an example of a new class of glycosides of polyhydroxylated piperidine alkaloids isolated from seed of the legume Xanthocercis zambesiaca. (Bak.) Dunn. Unlike a number of polyhydroxylated piperidines, neither the glucoside (1) nor free fagomine [1,2,5-trideoxy-1,5-imino-D-arabinohexitol] (3) showed any inhibitory activity towards glycosidase enzymes from a variety of sources.",
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