Enzyme-mediated transglycosylation of rutinose (6-O-α-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697
Language English Country United States Media print-electronic
Document type Journal Article
Grant support
7AMB13AR005
Ministerio de Ciencia, Tecnología e Innovación Productiva
7AMB13AR005
Ministry of Education, Youth and Science
LTC17009
Ministry of Education, Youth and Science
Agencia Nacional de Promoción Científica y Tecnológica
MultiGlycoNano
European Cooperation in Science and Technology
CM1102
European Cooperation in Science and Technology
Universidad Nacional de La Pampa
Consejo Nacional de Investigaciones Científicas y Técnicas
PubMed
30294837
DOI
10.1002/bab.1695
Knihovny.cz E-resources
- Keywords
- hesperidin, hydroquinone, α-rhamnosyl-β-glucosidase,
- MeSH
- Acremonium enzymology genetics MeSH
- Disaccharides chemistry genetics MeSH
- Fungal Proteins chemistry genetics metabolism MeSH
- Glycoside Hydrolases chemistry genetics metabolism MeSH
- Glycosylation MeSH
- Hydrogen-Ion Concentration MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Disaccharides MeSH
- Fungal Proteins MeSH
- Glycoside Hydrolases MeSH
- rutinose MeSH Browser
The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-l-rhamnopyranosyl-β-d-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values ≤6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 °C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds.
References provided by Crossref.org
Flavonoids as Aglycones in Retaining Glycosidase-Catalyzed Reactions: Prospects for Green Chemistry
