Recent trends in the modification of polyphenolic compounds using hydroxylation and glycosylation

Lee, Uk‐Jae; Sohng, Jae Kyung; Kim, Byung‐Gee; Choi, Kwon‐Young

doi:10.1016/j.copbio.2023.102914

Cited by 9 publications

(2 citation statements)

References 61 publications

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“…Plants contain a broad variety of natural phenolics, which serve as important compounds in food and pharmaceutical industry due to their diverse biological activities 1 – 3 . Glycosylation presents an effective method for mitigating the challenges posed by low solubility, poor stability, and limited bioavailability of phenolic compounds in their applications 4 – 6 . Uridine diphosphate (UDP)-dependent glycosyltransferases (UGTs) play a pivotal role in the natural glycosylation and biosynthesis of various phenolic glycosides by transferring UDP-sugars to acceptor substrates 7 – 10 .…”

Section: Introductionmentioning

confidence: 99%

Discovery, characterization, and comparative analysis of new UGT72 and UGT84 family glycosyltransferases

Li,

Borg,

Krammer

et al. 2024

Commun Chem

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Glycosylated derivatives of natural product polyphenols display a spectrum of biological activities, rendering them critical for both nutritional and pharmacological applications. Their enzymatic synthesis by glycosyltransferases is frequently constrained by the limited repertoire of characterized enzyme-catalyzed transformations. Here, we explore the glycosylation capabilities and substrate preferences of newly identified plant uridine diphosphate (UDP)-dependent glycosyltransferases (UGTs) within the UGT72 and UGT84 families, with particular focus on natural polyphenol glycosylation from UDP-glucose. Four UGTs are classified according to their phylogenetic relationships and reaction products, identifying them as biocatalysts for either glucoside (UGT72 enzymes) or glucose ester (UGT84 members) formation from selected phenylpropanoid compounds. Detailed kinetic evaluations expose the unique attributes of these enzymes, including their specific activities and regio-selectivities towards diverse polyphenolic substrates, with product characterizations validating the capacity of UGT84 family members to perform di-O-glycosylation on flavones. Sequence analysis coupled with structural predictions through AlphaFold reveal an unexpected absence of a conserved threonine residue across all four enzymes, a trait previously linked to pentosyltransferases. This comparative analysis broadens the understood substrate specificity range for UGT72 and UGT84 enzymes, enhancing our understanding of their utility in the production of natural phenolic glycosides. The findings from this in-depth characterization provide valuable insights into the functional versatility of UGT-mediated reactions.

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Section: Introductionmentioning

confidence: 99%

Discovery, characterization, and comparative analysis of new UGT72 and UGT84 family glycosyltransferases

Li,

Borg,

Krammer

et al. 2024

Commun Chem

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“…As people continue to pursue nature, green alternatives, and health, the demand for natural products in fields such as pharmaceuticals, food, and cosmetics is continuously increasing, and there is an urgent need to obtain more naturally produced high-quality active substances . A large variety of polyphenolic compounds are widely distributed in plants, such as Euphorbiaceae, Umbelliferae, and Leguminosae plants, and have various effects, such as antioxidant, antitumor, antimicrobial, anti-inflammatory, hypoglycemic, lipid-lowering, and liver protection, , with abundant reserves. , In addition to polyphenolic compounds, some researchers have discovered various amide compounds with rich biological activity from natural plants such as capsaicin, camptothecin, and colchicine. Their excellent antioxidant, antibacterial, anti-inflammatory, antitumor, and hypoglycemic activities have allowed them to have a significant role in the fields of food and medicine. − …”

Section: Introductionmentioning

confidence: 99%

Antiultraviolet, Antioxidant, and Antimicrobial Properties and Anticancer Potential of Novel Environmentally Friendly Amide-Modified Gallic Acid Derivatives

Wang,

Cong,

Zhang

et al. 2023

J. Agric. Food Chem.

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Polyphenols and amides isolated from natural products have various biological functions, such as antioxidant, antimicrobial, anticancer, and antiviral activities, and they are widely used in the fields of food and medicine. In this work, four novel and environmentally friendly amide-modified gallic acid derivatives (AMGADs), which were prepared by using different amides to modify gallic acid (GA) from Polygonaceae plants, displayed good antiultraviolet (anti-UV), antioxidant, antimicrobial, and anticancer effects. Significantly, the anti-UV capability of compounds n1 and n2 was notably superior to that of the UV absorber GA. Moreover, compound n2 possessed better 2,2-diphenyl-1-picrylhydrazyl radical (DPPH•) scavenging ability and ferric reducing antioxidant power than vitamin C. The antibacterial activities of all AMGADs, with inhibition rates of more than 96.00 and 79.00% for Escherichia coli and Staphylococcus aureus, respectively, were better than those of GA. Compound n1 had broad-spectrum anticancer activity, and its inhibitory effect on HepG2 cells exceeded that of 5-fluorouracil. The good and rich bioactivities of these AMGADs revealed that combining GA with amides is conducive to improving the activity of GA, and this study laid a good foundation for their scientific application in the fields of food and medicine.

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Key-enzymes involved in the biosynthesis of resveratrol-based stilbenes in Vitis spp.: a review

Marant,

Crouzet,

Flourat

et al. 2024

Phytochem Rev

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Recent trends in the modification of polyphenolic compounds using hydroxylation and glycosylation

Cited by 9 publications

References 61 publications

Discovery, characterization, and comparative analysis of new UGT72 and UGT84 family glycosyltransferases

Discovery, characterization, and comparative analysis of new UGT72 and UGT84 family glycosyltransferases

Antiultraviolet, Antioxidant, and Antimicrobial Properties and Anticancer Potential of Novel Environmentally Friendly Amide-Modified Gallic Acid Derivatives

Key-enzymes involved in the biosynthesis of resveratrol-based stilbenes in Vitis spp.: a review

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