Recombinant α-l-rhamnosidase from Aspergillus terreus in selective trimming of rutin

Gerstorferová, Daniela; Fliedrová, Barbora; Halada, Petr; Marhol, Petr; Křen, Vladimı́r; Weignerová, Lenka

doi:10.1016/j.procbio.2012.02.014

Cited by 51 publications

(39 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…For this purpose recombinant a-l-rhamnosidase from A. terreus void of b-glucosidase activity (expressed in P. pastoris) can be used. [25] We have exemplified this selective enzymatic trimming of rutinosides in the preparation of quercetin 3-b-glucopyranoside from rutin. [26] We have thus provided an affordable tool for the preparation of rutinosides of various aglycones at a preparative scale, which will enable further detailed study of these compounds.…”

Section: Discussionmentioning

confidence: 99%

α‐L‐Rhamnosyl‐β‐D‐glucosidase (Rutinosidase) from Aspergillus niger: Characterization and Synthetic Potential of a Novel Diglycosidase

et al. 2014

Self Cite

View full text Add to dashboard Cite

Abstract:We report the first heterologous production of a fungal rutinosidase (6-O-a-l-rhamnopyranosyl-b-d-glucopyranosidase) in Pichia pastoris. The recombinant rutinosidase was purified from the culture medium to apparent homogeneity and biochemically characterized. The enzyme reacts with rutin and cleaves the glycosidic linkage between the disaccharide rutinose and the aglycone. Furthermore, it exhibits high transglycosylation activity, transferring rutinose from rutin as a glycosyl donor onto various alcohols and phenols. The utility of the recombinant rutinosidase was demonstrated by its use for the synthesis of a broad spectrum of rutinosides of primary (saturated and unsaturated), secondary, acyclic and phenolic alcohols as well as for the preparation of free rutinose. Moreover, the a-l-rhamnosidase-catalyzed synthesis of a chromogenic substrate for a rutinosidase assay -para-nitrophenyl b-rutinoside -is described.

show abstract

Section: Discussionmentioning

confidence: 99%

α‐L‐Rhamnosyl‐β‐D‐glucosidase (Rutinosidase) from Aspergillus niger: Characterization and Synthetic Potential of a Novel Diglycosidase

et al. 2014

Self Cite

View full text Add to dashboard Cite

show abstract

“…Isoquercitrin is widely distributed as well, but it could not until recently be prepared in sufficient amounts as a result of its low content in plant material . Hence, a new and efficient method for the production of highly pure isoquercitrin (>95 %) from rutin by the alkali‐tolerant α‐ l ‐rhamnosidase from Aspergillus terreus was developed . Isoquercitrin is a very efficient chemoprotective agent in both in vivo and in vitro experiments against cancer, allergy, cardiovascular diseases, diabetes, and oxidative stress and it displays better bioavailability than rutin and quercetin …”

Section: Introductionmentioning

confidence: 99%

“…[16] Hence, an ew and efficient method for the production of highly pure isoquercitrin (> 95 %) from rutin by the alkali-tolerant a-l-rhamnosidase from Aspergillus terreus was developed. [17][18][19] Isoquercitrin is av ery efficient chemoprotective agenti nb oth in vivo and in vitro experimentsa gainst cancer,a llergy,c ardiovascular diseases, diabetes, ando xidative stress and it displays better bioavailability than rutin and quercetin. [5] (+ +)-Taxifolin,i solated from the bark of Pinus roxburhii, Larix sibirica,o rTaxus chinensis var.…”

Section: Introductionmentioning

confidence: 99%

Prokaryotic and Eukaryotic Aryl Sulfotransferases: Sulfation of Quercetin and Its Derivatives

et al. 2015

Self Cite

View full text Add to dashboard Cite

Two types of sulfotransferases, namely recombinant rat liver aryl sulfotransferase AstIV and bacterial aryl sulfotransferase from Desulfitobacterium hafniense, were used for the sulfation of quercetin, its glycosylated derivatives (isoquercitrin and rutin), and dihydroquercetin ((+)‐taxifolin). The rat liver enzyme was able to sulfate only quercetin and taxifolin, whereas the quercetin glycosides remained intact. The D. hafniense enzyme sulfated isoquercitrin and rutin selectively at the C‐4′ position of the catechol moiety with very good yields. Taxifolin was sulfated at the C‐4′ position and a minor amount of the C‐3′ isomer was formed. Sulfation of quercetin proceeded preferentially at the C‐3′ position, but a lower proportion of the C‐4′ isomer was formed as well. A detailed analysis of the kinetics of this reaction is provided and a full structural analysis of all products is presented.

show abstract

“…This reactionh as another advantage:a ll reactants and products are nontoxic (natural) flavonoids and, thus, they do not compromise potential pharmaceutical and/or nutraceutical applications.R utinosylated substances can be used also as food additives, ingredients in cosmetics, and antiviral agents. [21] This enzyme preparation,devoid of b-glucosidaseactivity, has been shown to efficiently and selectively cleave the a(6!1) rhamnosyl unit of rutin to yield isoquercitrin (11). [20] Often, however,t he corresponding b-glucosides are required.…”

Section: Introductionmentioning

confidence: 99%

A Sustainable One‐Pot, Two‐Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides

et al. 2017

View full text Add to dashboard Cite

A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective "trimming" of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.

show abstract

Recombinant α-l-rhamnosidase from Aspergillus terreus in selective trimming of rutin

Cited by 51 publications

References 46 publications

α‐L‐Rhamnosyl‐β‐D‐glucosidase (Rutinosidase) from Aspergillus niger: Characterization and Synthetic Potential of a Novel Diglycosidase

α‐L‐Rhamnosyl‐β‐D‐glucosidase (Rutinosidase) from Aspergillus niger: Characterization and Synthetic Potential of a Novel Diglycosidase

Prokaryotic and Eukaryotic Aryl Sulfotransferases: Sulfation of Quercetin and Its Derivatives

A Sustainable One‐Pot, Two‐Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides

Contact Info

Product

Resources

About