Plant and Cell Physiology Advance Access published online on June 4, 2007
Plant and Cell Physiology, doi:10.1093/pcp/pcm065
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Vicianin Hydrolase Is a Novel Cyanogenic ß-Glycosidase Specific to ß-Vicianoside (6-O-
-L-arabinopyranosyl-ß-D-glucopyranoside) in Seeds of Vicia angustifolia
Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
#Corresponding author: Masaharu Mizutani. Institute for Chemical Research, Kyoto University, Gokasho, Uji, Kyoto 611-0011, Japan. Telephone: -81-774-38-3232, FAX: -81-774-38-3229, E-mail: mizutani{at}scl.kyoto-u.ac.jp
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Abstract |
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Cyanogenic disaccharide glycoside, vicianin [mandelonitrile ß-vicianoside (6-O-
-L-arabinopyranosyl-ß-D-glucopyranoside)], is accumulated in seeds of Vicia angustifolia var. segetalis. Vicianin hydrolase (VH) catalyzes the hydrolysis of vicianin into mandelonitrile and a disaccharide vicianose. VH was purified from the seeds using DEAE-, CM-, and Con A-Sepharose chromatography, and the molecular mass of the purified VH was estimated to be 56 kD on SDS-PAGE. The N-terminal amino acid sequence of the purified VH was determined, and a cDNA encoding VH was obtained. The deduced VH protein consists of a 509 amino acid polypeptide containing a putative secretion signal peptide. It shares about 50% identity with various kinds of plant ß-glycosidases including tea leaf ß-primeverosidase and furcatin hydrolase, and is classified in family 1 of the glycosyl hydrolases. The VH transcript was detected abundantly in seeds and moderately in flowers but slightly in leaves, stems, and roots, indicating that organ distribution of the VH expression is similar to that of the substrate vicianin. The recombinant VH was produced in insect cells with a baculovirus system, and was compared with the native VH in terms of substrate specificity. Both enzymes hydrolyzed vicianin to release vicianose, demonstrating that VH is a disaccharide-specific ß-glycosidase. VH also hydrolyzed the mandelonitrile ß-glucoside prunasin at some extent but did not hydrolyze the gentiobioside amygdalin, both of which contain the same aglycone as vicianin. Thus, VH is a unique cyanogenic glycosidase showing high glycone specificity to the disaccharide vicianoside.
Keywords: cyanogenesis - cyanogenic glycoside - disaccharide glycoside - disaccharide-glycoside specific glycosidase - family 1 glycosyl hydrolase - vicianin
1Present address: Department of Biological Sciences, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA
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