Biotransformation of phloretin by amylosucrase yields three novel dihydrochalcone glucosides

Overwin, Heike; Wray, Victor; Höfer, Bernd

doi:10.1016/j.jbiotec.2015.07.002

Cited by 26 publications

(14 citation statements)

References 39 publications

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“…The ratio of donor to acceptor suggests that the conversion yield is affected even if a sufficient amount of enzyme is supplied. Similar to the results of this study (Table 1), previous studies reported that the conversion efficiency increased when the concentration of the donor was higher than that of the acceptor [31,39,40]. The enzyme-modified glycosylation of lipophilic compounds is known to be complex because of the low solubility of lipophilic compounds in aqueous systems [41].…”

Section: Transglycosylation Of Ifas With Dgassupporting

confidence: 90%

Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation

Jung

Kim

et al. 2020

Molecules

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Isoflavones in soybeans are well-known phytoestrogens. Soy isoflavones present in conjugated forms are converted to aglycone forms during processing and storage. Isoflavone aglycones (IFAs) of soybeans in human diets have poor solubility in water, resulting in low bioavailability and bioactivity. Enzyme-mediated glycosylation is an efficient and environmentally friendly way to modify the physicochemical properties of soy IFAs. In this study, we determined the optimal reaction conditions for Deinococcus geothermalis amylosucrase-mediated α-1,4 glycosylation of IFA-rich soybean extract to improve the bioaccessibility of IFAs. The conversion yields of soy IFAs were in decreasing order as follows: genistein > daidzein > glycitein. An enzyme quantity of 5 U and donor:acceptor ratios of 1000:1 (glycitein) and 400:1 (daidzein and genistein) resulted in high conversion yield (average 95.7%). These optimal reaction conditions for transglycosylation can be used to obtain transglycosylated IFA-rich functional ingredients from soybeans.

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Section: Transglycosylation Of Ifas With Dgassupporting

confidence: 90%

Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation

Jung

Kim

et al. 2020

Molecules

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“…Then, glycosyltransferase enzymes transfer a saccharide moiety from an activated nucleotide sugar molecule to a nucleophilic acceptor (Faber 2011, Huang et al 2015. Glycosylation as a biocatalytic process is important because it can greatly influence the biological activity of natural products, increasing both chemical and biological stability of the compound (Overwin et al 2015).…”

mentioning

confidence: 99%

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Santos

Takahashi

2017

An. Acad. Bras. Ciênc.

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The in vitro metabolism of a widespread natural product, trachyloban-19-oic acid (1), by the fungal species Mucor plumbeus was studied in a sucrose-yeast liquid medium. Two products were isolated, and their structures were determined by spectroscopic means as 7β-hydroxytrachyloban-19-oic acid (5) and trachyloban-19-O-β-D-glucopyranosyl ester (6). To the best of our knowledge, compound 6 is herein reported by the first time in the literature. These compounds were assayed for acetylcholinesterase inhibition along with some related compounds. Compound 6 showed the highest acetylcholinesterase inhibitory activity at 10000 µg/mL among the tested compounds, a result (92.89%) comparable to the activity of the positive control, galanthamine (94.21%). Therefore, biotransformation of the natural product 1 by M. plumbeus produced a novel compound with potential as a new lead to develop anti-Alzheimer medicines.

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“…Phloretin and its glycosides belong to a subclass of polyphenols within a larger group of plant-based phenolic bioactive natural products. They exhibit a wide variety of beneficial biological activities, such as anti-oxidant 1 , anti-inflammatory 2 , anti-cancer 3 and anti-diabetic activities 4 . Phloretin, a precursor of phloridzin, exhibits additional pharmacologically biological functions like anti-tumor 5 and anti-estrogen activities 6 , and inhibition of cardiovascular disease 3 .…”

mentioning

confidence: 99%

“…Phloretin, a precursor of phloridzin, exhibits additional pharmacologically biological functions like anti-tumor 5 and anti-estrogen activities 6 , and inhibition of cardiovascular disease 3 . However, the use of phloretin as a drug and food additive has been limited due to its weak aqueous solubility, chemical and/or biological instability, and low absorbability 1 3 7 8 . Attachment of sugar moieties to phloretin by glycosylation reactions can increase its aqueous solubility and in vivo half life, and typically exerts profound direct or indirect effects on its biological activity 1 3 7 9 10 .…”

mentioning

confidence: 99%

“…Phloridzin, a phloretin glycoside, is biosynthesized via a glycosylation reaction towards phloretin and UDPG catalyzed by phloretin-2′- O -glycosyltransferases (P2′GTs) 11 12 . Phloridzin is comparable to phloretin in the bioactive properties, but it exhibits greater bioavailability and lower toxicity 1 2 10 13 14 and is thus widely used in diverse commercial products as an alternative to phloretin 7 8 . To date, commercial available phloridzin is extracted from non-renewable sources using traditional solvent-based approaches 15 16 17 18 , which restrict its efficient availability.…”

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confidence: 99%

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Purification and characterization of a novel phloretin-2′-O-glycosyltransferase favoring phloridzin biosynthesis

Zhang

Liang

Wang

et al. 2016

Sci Rep

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Phloretin-2′-O-glycosyltransferase (P2′GT) catalyzes the last glycosylation step in the biosynthesis of phloridzin that contributes to the flavor, color and health benefits of apples and processed apple products. In this work, a novel P2′GT of Malus x domestica (MdP2′GT) with a specific activity of 46.82 μkat/Kg protein toward phloretin and uridine diphosphate glucose (UDPG) at an optimal temperature of 30 °C and pH 8.0 was purified from the engineered Pichia pastoris broth to homogeneity by anion exchange chromatography, His-Trap affinity chromatography and gel filtration. The purified MdP2′GT was low N-glycosylated and secreted as a stable dimer with a molecular mass of 70.7 kDa in its native form. Importantly, MdP2′GT also exhibited activity towards quercetin and adenosine diphosphate glucose (ADPG), kaempferol and UDPG, quercetin and UDP-galactose, isoliquiritigenin and UDPG, and luteolin and UDPG, producing only one isoquercitrin, astragalin, hyperoside, isoliquiritin, or cynaroside, respectively. This broad spectrum of activities make MdP2′GT a promising biocatalyst for the industrial preparation of the corresponding polyphenol glycosides, preferably for their subsequent isolation and purification. Besides, MdP2′GT displayed the lowest Km and the highest kcat/Km for phloretin and UDPG compared to all previously reported P2′GTs, making MdP2′GT favor phloridzin synthesis the most.

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Biotransformation of phloretin by amylosucrase yields three novel dihydrochalcone glucosides

Cited by 26 publications

References 39 publications

Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation

Enrichment of Polyglucosylated Isoflavones from Soybean Isoflavone Aglycones Using Optimized Amylosucrase Transglycosylation

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Purification and characterization of a novel phloretin-2′-O-glycosyltransferase favoring phloridzin biosynthesis

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