Glycosylation of luteolin in hydrophilic organic solvents and structure–antioxidant relationships of luteolin glycosides

Xu, Tingting; Wang, Chen; Jiang, Sijie; Yang, Tingting; Wu, Xueming

doi:10.1039/d2ra03300c

Cited by 16 publications

(2 citation statements)

References 27 publications

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“…Li et al revealed that D-α-tocopheryl polyethylene glycol 1000 succinate (TPGS)-coated liposomes provide an effective cancer chemotherapy strategy for model drugs with poor water solubility. Miyashita et al found that delivering luteolin through a microemulsion system can improve its oral bioavailability without affecting its metabolite profile [146,147]. These studies suggest that if the water solubility and bioactivity of luteolin are improved by some procedures, luteolin could be developed as a therapeutic drug to treat various inflammatory and cancerous diseases caused by inflammation or oxidative stress.…”

Section: Discussionmentioning

confidence: 99%

Immunopharmacological Activities of Luteolin in Chronic Diseases

Huang

Kim

Cho

2023

IJMS

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Flavonoids have been shown to have anti-oxidative effects, as well as other health benefits (e.g., anti-inflammatory and anti-tumor functions). Luteolin (3′, 4′, 5,7-tetrahydroxyflavone) is a flavonoid found in vegetables, fruits, flowers, and herbs, including celery, broccoli, green pepper, navel oranges, dandelion, peppermint, and rosemary. Luteolin has multiple useful effects, especially in regulating inflammation-related symptoms and diseases. In this paper, we summarize the studies about the immunopharmacological activity of luteolin on anti-inflammatory, anti-cardiovascular, anti-cancerous, and anti-neurodegenerative diseases published since 2018 and available in PubMed or Google Scholar. In this review, we also introduce some additional formulations of luteolin to improve its solubility and bioavailability.

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Section: Discussionmentioning

confidence: 99%

Immunopharmacological Activities of Luteolin in Chronic Diseases

Huang

Kim

Cho

2023

IJMS

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“…Interestingly, enzymatic glycosylation in organic solvents provides some industrially attractive advantages, such as reversing the thermodynamic equilibrium of glycosidases hydrolysis reactions, improving the aqueous solubility of hydrophobic substrates, eliminating microbial contamination, and lowing industrial cost process. 20,21 By using this approach, solvent-stable glycosidase (b-fructosidase from Arthrobacter nicotianae) showed high activity and stability in hydrophilic organic solvents with more than 90% yield of puerarin glycosides. 20 In this study, we demonstrate that the solvent-stable bfructosidase can be efficiently used for the glycosylation of vitexin, and evaluate the anti-tumor activities of vitexin glycosides.…”

Section: Introductionmentioning

confidence: 99%

Enzymatic synthesis of vitexin glycosides and their activity

Fan

Lou

et al. 2022

RSC Adv.

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Design and Synthesis of β‐O‐Glucosylated 5‐(Arylidene)‐6‐Aminouracils: Towards Water‐Soluble 8‐Aryl Xanthines as Effective Enzyme Inhibitors

Poslu,

Ertik,

Abul

et al. 2024

ChemistrySelect

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Abstract8‐Aryl xanthines are selective enzyme inhibitors modified from naturally occurring methylxanthines. However, the low water solubility of substituted xanthines restricts their clinical applications. We developed a strategy to improve the water solubility of biologically privileged 8‐aryl xanthines. A series of glucosylated 5‐(arylidene)‐6‐aminouracil was synthesized as 8‐aryl‐1,3‐dimethyl xanthine precursors and fully characterized with spectroscopic methods. Koenigs‐Knorr reaction was used to synthesize β‐O‐glucosylated aromatic aldehydes which were then reacted with 5,6‐diamino‐1,3‐dimethyluracil to obtain the corresponding 5‐(arylidene)‐6‐aminouracils. The strategy was validated by the ring‐closing reaction of a β‐O‐glucosylated 5‐(arylidene)‐6‐aminouracil derivative with iodine (I2) in dimethoxyethane. The water solubility of the glucosylated 8‐aryl‐1,3‐dimethyl xanthine and its non‐glycosylated counterpart was compared. Glucosylation improved the water solubility of the compound. The effect of glucosylation on the bioactivity of the compounds was investigated by measuring their inhibition effect on some common enzymes. The glucosylated 8‐aryl xanthine demonstrated significantly better efficiency. Molecular docking was performed to elucidate the ligand‐protein interactions. Since the target enzymes are primarily related to brain disorders, the blood‐brain barrier (BBB) penetration ability of 8‐aryl xanthine partners was investigated. According to adsorption, distribution, metabolism, excretion, and toxicity (ADMET) predictions, glucosylated 8‐aryl xanthine was found to be BBB permeable.

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Glycosylation of luteolin in hydrophilic organic solvents and structure–antioxidant relationships of luteolin glycosides

Abstract: Efficient glycosylation of luteolin in organic solvents and the structure–antioxidant relationships of luteolin glycosides were reported for the first time.

Cited by 16 publications

References 27 publications

Immunopharmacological Activities of Luteolin in Chronic Diseases

Immunopharmacological Activities of Luteolin in Chronic Diseases

Enzymatic synthesis of vitexin glycosides and their activity

Design and Synthesis of β‐O‐Glucosylated 5‐(Arylidene)‐6‐Aminouracils: Towards Water‐Soluble 8‐Aryl Xanthines as Effective Enzyme Inhibitors

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