Exolytic hydrolysis of toxic plant glucosides by guinea pig liver cytosolic beta-glucosidase.
We demonstrate that although the guinea pig liver cytosolic beta-glucosidase does not catalyze the hydrolysis of gentiobiose, it does hydrolyze, disaccharide-containing glycosides such as p-nitrophenyl-beta-D-gentiobioside (Glc beta 1----6Glc beta-pNP) and mandelonitrile-beta-D-gentiobioside (amygdalin). Furthermore, we establish that the enzyme attacks disaccharide glycosides exolytically; specifically, we document the exolytic deglucosylation of amygdalin and the generation of the intermediate monosaccharide glycoside mandelonitrile-beta-D-glucoside prior to the formation of the aglycone (mandelonitrile). We also show that the cytosolic beta-glucosidase catalyzes the hydrolysis of various phenolic (e.g. arbutin and salicin) and cyanogenic plant glucosides (e.g. prunasin). Using the everted gut-sack technique, we demonstrate that the plant glucosides, amygdalin, prunasin, and vicine, are transported across the small intestine of the guinea pig efficiently and without being hydrolyzed. Based on these data we speculate that the cytosolic beta-glucosidase may participate in biotransformation of toxic plant glucosides.
Gopalan
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V
Department of Biochemistry, School of Medicine, University of New Mexico, Albuquerque 87131.
Pastuszyn
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A
Galey
W R
WR
Glew
R H
RH
D000678:Amygdalin / Q000378:metabolism; D000818:Animals; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D003600:Cytosol / Q000201:enzymology; D004187:Disaccharides / Q000378:metabolism*; D005960:Glucosides / Q000378:metabolism*; D006168:Guinea Pigs; D007700:Kinetics; D008099:Liver / Q000201:enzymology*; D008969:Molecular Sequence Data; D010947:Plants, Toxic; D013379:Substrate Specificity; D001617:beta-Glucosidase / Q000378:metabolism
D004187:Disaccharides; D005960:Glucosides; D000678:Amygdalin; D001617:beta-Glucosidase