An effective biphase system accelerates hesperidinase-catalyzed conversion of rutin to isoquercitrin

Isoquercitrin is a rare, natural ingredient with several biological activities that is a key precursor for the synthesis of enzymatically modified isoquercitrin (EMIQ). The enzymatic production of isoquercitrin from rutin catalyzed by hesperidinase is feasible; however, the bioprocess is hindered by...

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Bibliographic Details
Published in:Scientific reports 2015-03, Vol.5 (1), p.8682, Article 8682
Main Authors: Wang, Jun, Gong, An, Yang, Cai-Feng, Bao, Qi, Shi, Xin-Yi, Han, Bei-Bei, Wu, Xiang-Yang, Wu, Fu-An
Format: Article
Language:English
Subjects:
Benign
Biosynthesis
Biotransformation
Catalysis
Circular dichroism
Conversion
Enzymes
Glycine
Glycoside Hydrolases - chemistry
Glycoside Hydrolases - metabolism
Hydrogen-Ion Concentration
Kinetics
Liquid chromatography
Mass spectroscopy
pH effects
Quercetin - analogs & derivatives
Quercetin - chemistry
Rutin
Rutin - chemistry
Sodium
Sodium hydroxide
Solvents
Temperature
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Summary:Isoquercitrin is a rare, natural ingredient with several biological activities that is a key precursor for the synthesis of enzymatically modified isoquercitrin (EMIQ). The enzymatic production of isoquercitrin from rutin catalyzed by hesperidinase is feasible; however, the bioprocess is hindered by low substrate concentration and a long reaction time. Thus, a novel biphase system consisting of [Bmim][BF4]:glycine-sodium hydroxide (pH 9) (10:90, v/v) and glyceryl triacetate (1:1, v/v) was initially established for isoquercitrin production. The biotransformation product was identified using liquid chromatography-mass spectrometry, and the bonding mechanism of the enzyme and substrate was inferred using circular dichroism spectra and kinetic parameters. The highest rutin conversion of 99.5% and isoquercitrin yield of 93.9% were obtained after 3 h. The reaction route is environmentally benign and mild, and the biphase system could be reused. The substrate concentration was increased 2.6-fold, the reaction time was reduced to three tenths the original time. The three-dimensional structure of hesperidinase was changed in the biphase system, which α-helix and random content were reduced and β-sheet content was increased. Thus, the developed biphase system can effectively strengthen the hesperidinase-catalyzed synthesis of isoquercitrin with high yield.
ISSN:2045-2322
2045-2322
DOI:10.1038/srep08682