6,7-diepicastanospermine, a tetrahydroxyindolizidine alkaloid inhibitor of amyloglucosidase

Journal Article · Tue Oct 15 04:00:00 EDT 1991 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00105a024· OSTI ID:5820977

Molyneux, R J; Benson, M ^[1]; Pan, Y T; Tropea, J E; Kaushal, G P; Elbein, A D ^[2]

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1. Dept. of Agriculture, Albany, CA (United States)
2. Univ. of Texas, San Antonio (United States)

A tetrahydroxyindolizidine alkaloid, 6,7-diepicastanospermine, was isolated from the seeds of Castanospermum australe by extraction with methanol and purified to homogeneity using ion-exchange, preparative thin-layer, and radial chromatography. A very low yield of a pyrrolidine alkaloid, N-(hydroxyethyl)-2-(hydroxymethyl)-3-hydroxypyrrolidine, was also obtained by analogous methods. The purity of both alkaloids was established by gas chromatography of their trimethylsilyl (TMS) derivatives as better than 99%. The molecular weight of each alkaloid was established as 189 and 161, respectively, by mass spectrometry, and the structure of each was deduced from their {sup 1}H and {sup 13}C NMR spectra. The structure of the pyrrolidine alkaloids which co-occur in C. australe. 6,7-Diepicastanospermine was found to be a moderately good inhibitor of the fungal {alpha}-glucosidase, amyloglucosidase and a relatively weak inhibitor of {beta}-glucosidase. It failed to inhibit {alpha}-glucosidase. It failed to inhibit {alpha}- or {beta}-galactosidase, {alpha}- or {beta}-mannosidase, or {alpha}-L-fucosidase. Comparison of its inhibitory activity toward amyloglucosidase with those of its isomers, castanospermine and 6-epicastanospermine, demonstrated that epimerization of a single hydroxyl group can produce significant alteration of such inhibitory properties.

• OSTI ID: 5820977
• Journal Information: Biochemistry; (United States), Journal Name: Biochemistry; (United States) Vol. 30:41; ISSN 0006-2960; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

550600* -- Medicine
62 RADIOLOGY AND NUCLEAR MEDICINE
ALKALOIDS
AMINES
BARYONS
BIOCHEMICAL REACTION KINETICS
CARBON 13
CARBON ISOTOPES
CHROMATOGRAPHY
ELEMENTARY PARTICLES
ENZYME INHIBITORS
ENZYMES
EVEN-ODD NUCLEI
FERMIONS
GAS CHROMATOGRAPHY
GLUCOSIDASE
GLYCOSYL HYDROLASES
HADRONS
HYDROLASES
ISOTOPES
KINETICS
LIGHT NUCLEI
MAGNETIC RESONANCE
MOLECULAR STRUCTURE
MOLECULAR WEIGHT
NUCLEAR MAGNETIC RESONANCE
NUCLEI
NUCLEONS
O-GLYCOSYL HYDROLASES
ORGANIC COMPOUNDS
PROTEINS
PROTONS
PURIFICATION
REACTION KINETICS
RESONANCE
SEEDS
SEPARATION PROCESSES
SPERMINE
STABLE ISOTOPES