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

Šimčíková, Daniela; Kotik, Michael; Weignerová, Lenka; Halada, Petr; Pelantová, Helena; Adamcová, Kateřina; Křen, Vladimı́r

doi:10.1002/adsc.201400566

Cited by 43 publications

(56 citation statements)

References 31 publications

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“…The recombinant rutinosidase was prepared using a Pichia pastoris expression system. [17] Rutin was used as a universal glycosyl donor throughout all experiments. The primary screening was performed under the same conditions that proved to be effective for polyphenol rutinosylation.…”

Section: Resultsmentioning

confidence: 99%

“…This enzyme, the rutinosidase from Aspergillus niger (EC 3.2.1.168, CAZY GH5_23), is capable of transferring rutinosyl (6-O-α-l-rhamnopyranosyl-β-d-glucopyranosyl) residue onto various alcohols, but most interestingly also to phenolic acceptors, which are generally difficult to glycosylate with glycosidases. [17] A major advantage of this transglycosylation reaction is the use of inexpensive and biocompatible rutin (1) as the glycosyl donor, while quercetin (2) as a byproduct of the reaction precipitates and can be easily removed from the reaction mixture by filtration. The produced rutinosides can be conveniently transformed in situ via a telescoping reaction with α-l-rhamnosidase to yield the respective β-glucopyranosides.…”

Section: Introductionmentioning

confidence: 99%

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Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

et al. 2019

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Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. Scheme 2. Glycosylation of (E)-p-coumaric acid (3). Scheme 3. Proposed mechanism of rutinosylation of hydroxycinnamic acids at the carboxy moiety.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

et al. 2019

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“…This may be overcome by whole-cell biotransformation setup, where the cells producing the glycosyltransferase activity can provide the required recycling of the costly donors in situ [ 14 , 15 ]. In the past decade, both natural and engineered glycosidases [ 16 ] have come into play as some of them have been shown to possess the ability of transferring glycosyl moieties onto phenolic hydroxyls [ 17 , 18 , 19 ]. They offer robustness, stability, scalable production, affordable substrates and a simple reaction design without the need of in situ regeneration of nucleotide sugar substrates [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

“Sweet Flavonoids”: Glycosidase-Catalyzed Modifications

Slámová

Kapešová

Valentová

2018

IJMS

166

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Natural flavonoids, especially in their glycosylated forms, are the most abundant phenolic compounds found in plants, fruit, and vegetables. They exhibit a large variety of beneficial physiological effects, which makes them generally interesting in a broad spectrum of scientific areas. In this review, we focus on recent advances in the modifications of the glycosidic parts of various flavonoids employing glycosidases, covering both selective trimming of the sugar moieties and glycosylation of flavonoid aglycones by natural and mutant glycosidases. Glycosylation of flavonoids strongly enhances their water solubility and thus increases their bioavailability. Antioxidant and most biological activities are usually less pronounced in glycosides, but some specific bioactivities are enhanced. The presence of l-rhamnose (6-deoxy-α-l-mannopyranose) in rhamnosides, rutinosides (rutin, hesperidin) and neohesperidosides (naringin) plays an important role in properties of flavonoid glycosides, which can be considered as “pro-drugs”. The natural hydrolytic activity of glycosidases is widely employed in biotechnological deglycosylation processes producing respective aglycones or partially deglycosylated flavonoids. Moreover, deglycosylation is quite commonly used in the food industry aiming at the improvement of sensoric properties of beverages such as debittering of citrus juices or enhancement of wine aromas. Therefore, natural and mutant glycosidases are excellent tools for modifications of flavonoid glycosides.

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“…Transglycosylation is the method of choice for the synthesis of numerous rutinosides. Two main approaches using α‐ l ‐rhamnosyl‐β‐ d ‐glucosidases, which are diglycosidases, have been pursued from either rutin or hesperidin as a rutinose donor . In this work, we explored the transglycosylation specificity of the α‐rhamnosyl‐β‐glucosidase from the fungus Acremonium sp.…”

Section: Introductionmentioning

confidence: 99%

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

Mazzaferro

Weiz

Braun

et al. 2018

Biotech and App Biochem

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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-rhamnopyranosylβ-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 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. C 2018 International

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

Cited by 43 publications

References 31 publications

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

Glycosidase‐Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

“Sweet Flavonoids”: Glycosidase-Catalyzed Modifications

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

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