Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

Gonzalez, Jose L. Ugia; Míguez, Noa; Padilla, J. Daniel; Leemans, Laura; Poveda, Ana; Jiménez‐Barbero, Jesús; Ballesteros, Antonio; Sandoval, Georgina; Plou, Francisco J.

doi:10.3390/molecules23112885

Cited by 22 publications

(16 citation statements)

References 49 publications

(62 reference statements)

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“…Hesperetin (5,7,3ʹ-trihydroxy-4ʹ-methoxyflavanone) is a natural flavanone glycoside, abundant in citrus fruits, including lemons, limes, mandarins, and oranges (Liu et al, 2016;Shirzad et al, 2017;González-Alfonso et al, 2018). Hesperetin represents various pharmacological characters, including anti-inflammatory, anti-oxidative, anti-tumor potentials (Parhiz et al, 2015;Alu'datt et al, 2017;Chen et al, 2019a;Li et al, 2020a).…”

Section: Flavonoidsmentioning

confidence: 99%

Natural Anti-Inflammatory Compounds as Drug Candidates for Inflammatory Bowel Disease

et al. 2021

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Inflammatory bowel disease (IBD) represents chronic recurrent intestinal inflammation resulting from various factors. Crohn’s disease (CD) and ulcerative colitis (UC) have been identified as the two major types of IBD. Currently, most of the drugs for IBD used commonly in the clinic have adverse reactions, and only a few drugs present long-lasting treatment effects. Moreover, issues of drug resistance and disease recurrence are frequent and difficult to resolve. Together, these issues cause difficulties in treating patients with IBD. Therefore, the development of novel therapeutic agents for the prevention and treatment of IBD is of significance. In this context, research on natural compounds exhibiting anti-inflammatory activity could be a novel approach to developing effective therapeutic strategies for IBD. Phytochemicals such as astragalus polysaccharide (APS), quercetin, limonin, ginsenoside Rd, luteolin, kaempferol, and icariin are reported to be effective in IBD treatment. In brief, natural compounds with anti-inflammatory activities are considered important candidate drugs for IBD treatment. The present review discusses the potential of certain natural compounds and their synthetic derivatives in the prevention and treatment of IBD.

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Section: Flavonoidsmentioning

confidence: 99%

Natural Anti-Inflammatory Compounds as Drug Candidates for Inflammatory Bowel Disease

et al. 2021

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“…(CGTase) Hesperidin monoglucoside 9.0 40 °C 75 [ 75 ] Hesperetin 3′- O-α-glucosides Hesperetin 5- O-α-glucosides Hesperetin 7-O-α-glucosides Starch CGTase Hesperetin 3′-O-α-maltoside Hesperetin 5-O-α-maltoside Hesperetin 7-O-α-maltoside 7.0 40 °C 49 62 50 [ 139 ] Hesperidin Soluble Starch Thermoanaerobacter sp . (CGTase) Hesperetin 7-O-α-D-glucopyranoside 5.0 60 °C 4.1 [ 40 ] 4-hydroxyphenyl α-glucopyranoside (α-arbutin) Soluble Starch Bacillus macerans (CGTase) Arbutin-α-glycosides -4-hydroxyphenyl β -maltoside ( β -Ab-α-G1) -4-hydroxyphenyl β -maltotrioside ( β -Ab-α-G2) 7.0 40 °C 70 [ 149 ] Genistin Soluble Starch alkalophilic Bacillus sp. I-5 (CGTase) Glucosyl-α(1–4)-genistin Maltosyl-α(1–4)-genistin 6.0 60 °C - [ 87 ] Genistin α-CD Paenibacillus macerans (CGTase) Genistin diglucoside 6.5 30 °C [ 42 ] Quercetin 7-O- β -D-glucoside Starch CGTase Quercetin 7-O- β -maltoside 7.0 40 °C 36 [ 141 ] Quercetin 7-O- β -maltotrioside 10 Quercetin 3-O- β -D-glucoside Quercetin 3-O- β -maltoside 40 ...…”

Section: Catalytic Mechanism Of Cgtasementioning

confidence: 99%

Comprehensive study on transglycosylation of CGTase from various sources

Lim

Rasti

Sulistyo

et al. 2021

Heliyon

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Transglycosylation is the in-vivo or in-vitro process of transferring glycosyl groups from a donor to an acceptor, which is usually performed by enzymatic reactions because of their simplicity, low steric hindrance, high region-specificity, low production cost, and mild processing conditions. One of the enzymes commonly used in the transglycosylation reaction is cyclodextrin glucanotransferase (CGTase). The transglycosylated products, catalyzed by CGTase, are widely used in food additives, supplements, and personal care and cosmetic products. This is due to improvements in the solubility, stability, bioactivity and length of the synthesized products. This paper's focus is on the importance of enzymes used in the transglycosylation reaction, their characteristics and mechanism of action, sources and production yield, and donor and acceptor specificities. Moreover, the influence of intrinsic and extrinsic factors on the enzymatic reaction, catalysis of glycosidic linkages, and advantages of CGTase transglycosylation reactions are discussed in detail.

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“…Furthermore, the formation of a homologous series of polyglucosylated products is normally described with this enzyme [20][21][22]. As a result, a low yield of the desired glycosylated product is typically obtained [23]. Several strategies have been assessed to improve the transglycosylation activity of CGTases, including protein engineering [24][25][26], chemical modification [7], immobilization [27,28], and the addition of cosolvents and additives [29][30][31].…”

Section: Introductionmentioning

confidence: 99%

“…Typical cosolvents for transglycosylation reactions include acetonitrile, DMSO, ethers, tertiary alcohols, etc. [22,23,36], and more recently, biomass-derived solvents and ionic liquids [37,38].…”

Section: Introductionmentioning

confidence: 99%

Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase

et al. 2019

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While testing the ability of cyclodextrin glucanotransferases (CGTases) to glucosylate a series of flavonoids in the presence of organic cosolvents, we found out that this enzyme was able to glycosylate a tertiary alcohol (tert-butyl alcohol). In particular, CGTases from Thermoanaerobacter sp. and Thermoanaerobacterium thermosulfurigenes EM1 gave rise to the appearance of at least two glycosylation products, which were characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) as tert-butyl-α-D-glucoside (major product) and tert-butyl-α-D-maltoside (minor product). Using partially hydrolyzed starch as glucose donor, the yield of transglucosylation was approximately 44% (13 g/L of tert-butyl-α-D-glucoside and 4 g/L of tert-butyl-α-D-maltoside). The synthesized tert-butyl-α-D-glucoside exhibited the typical surfactant behavior (critical micellar concentration, 4.0–4.5 mM) and its properties compared well with those of the related octyl-α-D-glucoside. To the best of our knowledge, this is the first description of an enzymatic α-glucosylation of a tertiary alcohol.

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Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

Cited by 22 publications

References 49 publications

Natural Anti-Inflammatory Compounds as Drug Candidates for Inflammatory Bowel Disease

Natural Anti-Inflammatory Compounds as Drug Candidates for Inflammatory Bowel Disease

Comprehensive study on transglycosylation of CGTase from various sources

Production and Surfactant Properties of Tert-Butyl α-d-Glucopyranosides Catalyzed by Cyclodextrin Glucanotransferase

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