Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F19%3A00504259" target="_blank" >RIV/61388971:_____/19:00504259 - isvavai.cz</a>

Výsledek na webu

<a href="https://iubmb.onlinelibrary.wiley.com/doi/full/10.1002/bab.1695" target="_blank" >https://iubmb.onlinelibrary.wiley.com/doi/full/10.1002/bab.1695</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/bab.1695" target="_blank" >10.1002/bab.1695</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

Popis výsledku v původním jazyce

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-alpha-rhamnosyl-beta-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-alpha-l-rhamnopyranosyl-beta-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-beta-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-beta-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 degrees 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 pK(a) value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds.

Název v anglickém jazyce

Enzyme-mediated transglycosylation of rutinose (6-O-alpha-l-rhamnosyl-d-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697

Popis výsledku anglicky

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-alpha-rhamnosyl-beta-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-alpha-l-rhamnopyranosyl-beta-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-beta-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-beta-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 degrees 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 pK(a) value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10608 - Biochemistry and molecular biology

Projekt

<a href="/cs/project/LTC17009" target="_blank" >LTC17009: Karotenoidy a flavonoidy: interakce a hybridní antioxidanty</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Biotechnology and Applied Biochemistry

ISSN

0885-4513

e-ISSN

—

Svazek periodika

66

Číslo periodika v rámci svazku

1

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

53-59

Kód UT WoS článku

000458289100006

EID výsledku v databázi Scopus

2-s2.0-85055577840