Enzymatic Processing of Bioactive Glycosides from Natural Sources

Weignerová, Lenka; Křen, Vladimı́r

doi:10.1007/128_2010_51

Cited by 10 publications

(6 citation statements)

References 91 publications

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“…Several polyphenols appear glycosylated in nature (4, 6) and the sugar moiety seems to play a major role in their solubility (7), partition coefficient (8), protection from oxygen, pH, temperature and/or light (9), absorption (10, 11), bioavailability (12), and bioactivity (13). Several studies demonstrated that glycosylation facilitates the diffusion of polyphenols into intestinal enterocytes (12, 14).…”

Section: Introductionmentioning

confidence: 99%

Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate

et al. 2019

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(–)-Epigallocatechin gallate (EGCG), the predominant catechin (≥50%) in green tea ( Camellia sinensis ), displays several bioactive properties but its stability and bioavailability are low. In this work, the properties of two α-glucosyl derivatives of EGCG (3′- and 7-O-α-D-glucopyranoside), obtained by enzymatic synthesis, were assessed. The α-glucosylation enhanced the pH and thermal stability of EGCG. The analysis of scavenging activity toward ABTS · + radicals showed that the α-glucosylation at C-7 of A-ring caused a higher loss of antioxidant activity compared with the sugar conjugation at C-3′ of B-ring. The 3′-glucoside also showed higher potential to alleviate intracellular reactive oxygen species (ROS) levels and to boost REDOX activity. The toxicity of EGCG and its monoglucosides was tested in human SH-S5Y5 neurons, RAW 264.7 macrophages, MRC5 fibroblasts, and HT-29 colon cancer cells. Interestingly, the 3′-O-α-D-glucoside increased the viability of neural cells in vitro (2.75-fold at 100 μM) in the presence of H 2 O 2 , whilst EGCG gave rise only to a 1.7-fold enhancement. In conclusion, the α-glucoside of EGCG at C-3′ has a great potential for nutraceutical, cosmetic and biomedical applications.

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Section: Introductionmentioning

confidence: 99%

Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate

et al. 2019

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“…Plant polyphenols constitute a large group of substances whose regular consumption may help to delay the appearance of several degenerative pathologies, including Parkinson’s and Alzheimer’s diseases, cancer, chronic inflammatory disease or atherosclerosis 1,2 . In nature, polyphenols can be found conjugated to sugars 3 , which play an important role in their solubility 4,5 , stability 6,7 , bioavailability 8 and bioactivity 9 . In fact, glycosylation is a tool to improve the bioavailability and pharmaceutical properties of polyphenols 10–14 .…”

Section: Introductionmentioning

confidence: 99%

Deciphering the molecular specificity of phenolic compounds as inhibitors or glycosyl acceptors of β-fructofuranosidase from Xanthophyllomyces dendrorhous

Ramirez-Escudero

Míguez

Gimeno-Pérez

et al. 2019

Sci Rep

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Enzymatic glycosylation of polyphenols is a tool to improve their physicochemical properties and bioavailability. On the other hand, glycosidic enzymes can be inhibited by phenolic compounds. In this work, we studied the specificity of various phenolics (hydroquinone, hydroxytyrosol, epigallocatechin gallate, catechol and p-nitrophenol) as fructosyl acceptors or inhibitors of the β-fructofuranosidase from Xanthophyllomyces dendrorhous (pXd-INV). Only hydroquinone and hydroxytyrosol gave rise to the formation of glycosylated products. For the rest, an inhibitory effect on both the hydrolytic (H) and transglycosylation (T) activity of pXd-INV, as well as an increase in the H/T ratio, was observed. To disclose the binding mode of each compound and elucidate the molecular features determining its acceptor or inhibitor behaviour, ternary complexes of the inactive mutant pXd-INV-D80A with fructose and the different polyphenols were analyzed by X-ray crystallography. All the compounds bind by stacking against Trp105 and locate one of their phenolic hydroxyls making a polar linkage to the fructose O2 at 3.6–3.8 Å from the C2, which could enable the ulterior nucleophilic attack leading to transfructosylation. Binding of hydroquinone was further investigated by soaking in absence of fructose, showing a flexible site that likely allows productive motion of the intermediates. Therefore, the acceptor capacity of the different polyphenols seems mediated by their ability to make flexible polar links with the protein, this flexibility being essential for the transfructosylation reaction to proceed. Finally, the binding affinity of the phenolic compounds was explained based on the two sites previously reported for pXd-INV.

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“…Several polyphenols appear glycosylated in nature, and the sugar moiety seems to play a significant function in their human absorption. , Glycosylation of polyphenols may thus modulate their bioavailability, bioactivity, and various physicochemical features, such as the solubility and partition coefficient . Glycosylation may also facilitate the entrance of several flavonoids into intestinal enterocytes .…”

Section: Introductionmentioning

confidence: 99%

“…4 Most polyphenols are hydrophobic molecules that exhibit poor absorption in vivo, giving rise to a negligible concentration in the circulatory streams. 5 Several polyphenols appear glycosylated in nature, 6 and the sugar moiety seems to play a significant function in their human absorption. 7,8 Glycosylation of polyphenols may thus modulate their bioavailability, 9 bioactivity, 10 and various physicochemical features, such as the solubility 11 and partition coefficient.…”

Section: ■ Introductionmentioning

confidence: 99%

Efficient α-Glucosylation of Epigallocatechin Gallate Catalyzed by Cyclodextrin Glucanotransferase from Thermoanaerobacter Species

Gonzalez

Leemans

Poveda

et al. 2018

J. Agric. Food Chem.

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The glycosylation of plant polyphenols may modulate their solubility and bioavailability and protect these molecules from oxygen, light degradation, and during gastrointestinal transit. In this work, the synthesis of various α-glucosyl derivatives of (-)-epigallocatechin gallate, the predominant catechin in green tea, was performed in water at 50 °C by a transglycosylation reaction catalyzed by cyclodextrin glycosyltransferase from Thermoanaerobacter sp. The molecular weight of reaction products was determined by high-performance liquid chromatography coupled to mass spectrometry. Using hydrolyzed potato starch as a glucosyl donor, two main monoglucosides were obtained with conversion yields of 58 and 13%, respectively. The products were isolated and chemically characterized by combining two-dimensional nuclear magnetic resonance methods. The major derivative was epigallocatechin gallate 3'- O-α-d-glucopyranoside (1), and the minor derivative was epigallocatechin gallate 7- O-α-d-glucopyranoside (2).

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Enzymatic Processing of Bioactive Glycosides from Natural Sources

Cited by 10 publications

References 91 publications

Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate

Effect of α-Glucosylation on the Stability, Antioxidant Properties, Toxicity, and Neuroprotective Activity of (–)-Epigallocatechin Gallate

Deciphering the molecular specificity of phenolic compounds as inhibitors or glycosyl acceptors of β-fructofuranosidase from Xanthophyllomyces dendrorhous

Efficient α-Glucosylation of Epigallocatechin Gallate Catalyzed by Cyclodextrin Glucanotransferase from Thermoanaerobacter Species

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