Purification of an isoflavonoid 7-O-β-apiosyl-glucoside β-glycosidase and its substrates from Dalbergia nigrescens Kurz

A β-glycosidase which hydrolyzes isoflavonoid glycosides, removing β-apiosyl glucose, and two substrates were purified from Dalbergia nigrescens seeds, and the glycoside substrate structures were identified. A β-glycosidase was purified from the seeds of Dalbergia nigescens Kurz based on its ability...

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Bibliographic Details
Published in:Phytochemistry (Oxford) 2005-08, Vol.66 (16), p.1880-1889
Main Authors: Chuankhayan, Phimonphan, Hua, Yanling, Svasti, Jisnuson, Sakdarat, Santi, Sullivan, Patrick A., Ketudat Cairns, James R.
Format: Article
Language:English
Subjects:
Apiosyl glucoside
beta-fucosidase
beta-fucoside
beta-glucosidase
beta-jucosidase
Biological and medical sciences
Catalysis
Dalbergia
Dalbergia - enzymology
Dalbergia nigrescens
Dalbergia nigrescens Kurz
dalpatein
Disaccharides - chemistry
Disaccharides - metabolism
enzyme kinetics
enzyme substrates
Enzymes
Fundamental and applied biological sciences. Psychology
glucosides
Glycoside Hydrolases - isolation & purification
Glycoside Hydrolases - metabolism
Hydrolysis
Isoflavones - chemistry
Isoflavones - metabolism
Isoflavonoid glycoside
isoflavonoids
Kinetics
Leguminosae
Metabolism
p-nitrophenyl beta-glucoside
plant biochemistry
Plant physiology and development
plant proteins
seeds
Seeds - enzymology
Substrate Specificity
β-Glucosidase
β-Glycosidase substrate
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Description
Summary:A β-glycosidase which hydrolyzes isoflavonoid glycosides, removing β-apiosyl glucose, and two substrates were purified from Dalbergia nigrescens seeds, and the glycoside substrate structures were identified. A β-glycosidase was purified from the seeds of Dalbergia nigescens Kurz based on its ability to hydrolyse p-nitrophenyl β-glucoside and β-fucoside. This enzyme did not hydrolyze various glycosidic substrates efficiently, so it was used to identify its own natural substrates. Two substrates were identified, isolated and their structures determined as: compound 1, dalpatein 7-O-β- d-apiofuranosyl-(1 → 6)-β- d-glucopyranoside and compound 2, 6,2′,4′,5′-tetramethoxy-7-hydroxy-7-O-β- d-apiofuranosyl-(1 → 6)-β- d-glucopyranoside (dalnigrein7-O-β- d-apiofuranosyl-(1 → 6)-β- d-glucopyranoside). The β-glycosidase removes the sugar from these glycosides as a disaccharide, despite its initial identification as a β-glucosidase and β-fucosidase.
ISSN:0031-9422
1873-3700
DOI:10.1016/j.phytochem.2005.06.024