Recent insights into oxidative metabolism of quercetin: catabolic profiles, degradation pathways, catalyzing metalloenzymes and molecular mechanisms

Article Medicine, Research & Experimental

Quercetin for managing type 2 diabetes and its complications, an insight into multitarget therapy

R. Dhanya

Summary: Quercetin, a bioflavonoid, shows promising potential in managing Type 2 diabetes and its complications. Further studies are needed to establish optimal dosing regimen and improve bioavailability.

BIOMEDICINE & PHARMACOTHERAPY (2022)

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Review Chemistry, Medicinal

Quercetin derivatives: Drug design, development, and biological activities, a review

Seyedeh Roya Alizadeh et al.

Summary: More studies are needed to develop new drugs that can overcome drug resistance and minimize side effects. Quercetin, a natural flavonoid, has shown diverse biological activities, but its poor solubility and bioavailability limit its applicability. Researchers have been exploring the modification of quercetin by designing and synthesizing novel derivatives to overcome these limitations. The physico-chemical properties of quercetin's molecular scaffold make it attractive for drug development, and the investigation of its derivatives' activities, chemical structure-activity relationship, and mechanism of action is crucial. Quercetin-based molecules have the potential to contribute to the discovery of medications for various diseases.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (2022)

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Article Biochemistry & Molecular Biology

Protection against indomethacin-induced loss of intestinal epithelial barrier function by a quercetin oxidation metabolite present in onion peel: In vitro and in vivo studies

Jocelyn Fuentes et al.

Summary: The quercetin oxidation metabolite 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (BZF) and its rich onion peel aqueous extract (OAE) can protect against the loss of intestinal epithelial barrier function (IEBF) induced by NSAIDs. The protective effect may involve the dual capacity of activating Nrf2 while inhibiting NF- K B activation.

JOURNAL OF NUTRITIONAL BIOCHEMISTRY (2022)

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Review Biochemistry & Molecular Biology

Revisiting the Oxidation of Flavonoids: Loss, Conservation or Enhancement of Their Antioxidant Properties

Herna Speisky et al.

Summary: Flavonoids have the ability to act as antioxidants, but their phenolic moieties are easily oxidized, compromising their antioxidant capacity. However, the oxidation of certain flavonoids can actually enhance their antioxidant properties. This apparent paradox is due to the pro-oxidant and/or electrophilic character of the oxidation-derived metabolites, which activate the cell's endogenous antioxidant capacity or prevent the activation of pro-oxidant pathways.

ANTIOXIDANTS (2022)

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Review Pharmacology & Pharmacy

Non-P450 Drug-Metabolizing Enzymes: Contribution to Drug Disposition, Toxicity, and Development

Tatsuki Fukami et al.

Summary: This review provides an overview of the metabolism of clinically used drugs and highlights the roles of cytochrome P450 enzymes and non-P450 phase I enzymes in drug metabolism. It emphasizes the importance of studying non-P450 phase I enzymes for improving drug efficacy and reducing adverse reactions.

ANNUAL REVIEW OF PHARMACOLOGY AND TOXICOLOGY (2022)

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Review Pharmacology & Pharmacy

Drug-oxidizing and conjugating non-cytochrome P450 (non-P450) enzymes in cynomolgus monkeys and common marmosets as preclinical models for humans

Yasuhiro Uno et al.

Summary: Many drug oxidations and conjugations in humans and non-human primates are mediated by various non-P450 enzymes, which have similar enzymatic profiles and substrate recognitions in cynomolgus macaques and common marmosets. However, these enzymes also exhibit some limited functional differences between species.

BIOCHEMICAL PHARMACOLOGY (2022)

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Review Biotechnology & Applied Microbiology

Discovery and mining of enzymes from the human gut microbiome

Baolei Jia et al.

Summary: This article discusses the recent efforts and technologies used for discovering and mining enzymes from the human gut microbiota. The wealth of knowledge on metabolites, reactions, genome sequences, and protein structures may lead to the development of strategies for enzyme mining. Ongoing efforts to annotate gut microbiota enzymes may elucidate catalytic mechanisms that could guide the clinical applications of the gut microbiome for diagnostic and therapeutic purposes.

TRENDS IN BIOTECHNOLOGY (2022)

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Article Chemistry, Applied

Investigation of new products of quercetin formed in boiling water via UPLC-Q-TOF-MS-MS analysis

Shiye Lin et al.

Summary: This study investigated the stability of quercetin in boiling water using UPLC-Q-TOF-MS-MS and identified the major degradation products. The results showed that quercetin gradually degraded with increasing boiling time, resulting in the formation of various degradation products.

FOOD CHEMISTRY (2022)

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Review Chemistry, Medicinal

A role for quercetin in coronavirus disease 2019 (COVID-19)

Giuseppe Derosa et al.

Summary: COVID-19, caused by novel coronavirus (SARS-CoV-2), was first detected in Wuhan City, China. Quercetin has the potential to inhibit virus replication and possesses anti-inflammatory and thrombin-inhibitory actions.

PHYTOTHERAPY RESEARCH (2021)

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Review Biochemistry & Molecular Biology

Similar but Still Different: Which Amino Acid Residues Are Responsible for Varying Activities in Type-III Copper Enzymes?

Loannis Kampatsikas et al.

Summary: The article reviews the role of amino acid residues affecting the different activities of PPOs, with the structural similarity between TYRs and COs complicating the elucidation of their modes of action on a structural basis.

CHEMBIOCHEM (2021)

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Article Agriculture, Multidisciplinary

Quercetin Attenuated Myeloperoxidase-Dependent HOCl Generation and Endothelial Dysfunction in Diabetic Vasculature

Rong Tian et al.

Summary: The study found that quercetin effectively inhibited MPO-mediated HOCl generation and cytotoxicity to vascular endothelial cells. Quercetin limited MPO/H2O2-dependent HOCl production by inhibiting MPO activity, reducing H2O2 generation in endothelial cells, and acting as a competitive substrate for MPO.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2021)

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Article Agriculture, Multidisciplinary

Prospective Selective Mechanism of Emerging Senolytic Agents Derived from Flavonoids

Yijun Wang et al.

Summary: Senescent cells play a role in the development of multiple chronic diseases, and selective clearance through senolytic drugs could be a potential therapeutic option. Quercetin and fisetin, both flavonoids, show promise as senolytic agents due to their prooxidant activities which may selectively target apoptosis-resistant senescent cells.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2021)

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Article Chemistry, Applied

Polyphenol oxidase dominates the conversions of flavonol glycosides in tea leaves

Xiao-Yuan Guo et al.

Summary: The study revealed that PPO plays a significant role in catalyzing flavonol glycosides in tea leaves, with the addition of POD enhancing the oxidation process. Myricetin glycosides showed the highest sensitivity to PPO, and sugar moieties enhanced the binding affinity of flavonol glycosides for PPO.

FOOD CHEMISTRY (2021)

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Article Agriculture, Multidisciplinary

Quercetin Oxidation Metabolite Present in Onion Peel Protects Caco-2 Cells against the Oxidative Stress, NF-κB Activation, and Loss of Epithelial Barrier Function Induced by NSAIDs

Jocelyn Fuentes et al.

Summary: The study investigated the protective effects of BZF and BZF-rich OAE against oxidative stress and increased permeability induced by NSAIDs, finding that the prevention of NSAIDs-induced oxidative stress and NF-kappa B activation plays no fundamental role in the IP-protecting effect of OAE, except for with indomethacin.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2021)

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Review Cell Biology

Quercetin Impact in Pancreatic Cancer: An Overview on Its Therapeutic Effects

Parina Asgharian et al.

Summary: Pancreatic cancer is a deadly malignancy with increasing mortality rates worldwide. The use of flavonoids like quercetin has shown promising anticancer abilities in controlling and treating pancreatic cancer.

OXIDATIVE MEDICINE AND CELLULAR LONGEVITY (2021)

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Article Multidisciplinary Sciences

Discovery of an ene-reductase for initiating flavone and flavonol catabolism in gut bacteria

Gaohua Yang et al.

Summary: This study identified an ene-reductase, FLR, from the gut bacterium Flavonifractor plautii ATCC 49531 that catalyses the hydrogenation of flavones and flavonols, shedding light on microbial metabolism of flavonoids in the human gut. The crystal structure analysis provided insights into the distinct catalytic property of FLR, which represents a new class of ene-reductases. Genetic and biochemical analyses highlighted the significance of FLR in the gut microbial consumption of dietary and medicinal flavonoids, offering potential implications for personalized nutrition and medicine.

NATURE COMMUNICATIONS (2021)

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Review Pharmacology & Pharmacy

Activation of Nrf2 signaling pathway by natural and synthetic chalcones: a therapeutic road map for oxidative stress

Melford Chuka Egbujor et al.

Summary: The Nrf2 signaling pathway is important for protecting the body from oxidative stress and xenobiotics. Chalcones, which are compounds with a common chemical structure of 1,3-diaryl-2-propen-1-one, have various pharmacological properties and can activate the Nrf2 signaling pathway. They are considered to be potential drug candidates for targeting Nrf2-dependent diseases due to their low toxicity, structural diversity, and ability to upregulate protective proteins.

EXPERT REVIEW OF CLINICAL PHARMACOLOGY (2021)

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Article Chemistry, Physical

Directed Evolution of a Plant Glycosyltransferase for Chemo- and Regioselective Glycosylation of Pharmaceutically Significant Flavonoids

Zexing Wen et al.

Summary: Plant glycosyltransferase MiCGT was engineered by directed evolution to catalyze the glycosylation of flavonoids for pharmaceutical applications, resulting in mutants with enhanced selectivity and activity towards seven different flavonoids. The best quadruple mutant VFAH showed strict 3-O glycosylation selectivity and a 120-fold activity enhancement towards the model substrate quercetin.

ACS CATALYSIS (2021)

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Review Biology

Role of Pirin, an Oxidative Stress Sensor Protein, in Epithelial Carcinogenesis

Francisco Perez-Dominguez et al.

Summary: Pirin is a protein detected at low levels in normal tissues, but at high levels in multiple cancers, particularly melanomas, cervical cancer, and squamous cell lung carcinomas. Its role in cancer is related to the host response against factors causing oxidative stress, favoring cell migration and metastasis. Pirin is a potential therapeutic target as it is an oxidative stress sensor and transcriptional activator of the NF-kappa B pathway.

BIOLOGY-BASEL (2021)

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Review Plant Sciences

Phenoloxidases in Plants-How Structural Diversity Enables Functional Specificity

Leonard Blaschek et al.

Summary: The metabolism of polyphenolic polymers is crucial for the development and response to environmental changes in organisms, with particular diversity observed in plants. Phenoloxidases, such as laccases, play a key role in polyphenolic metabolism and exhibit diverse functional roles and structures. Understanding the differences and similarities between phenoloxidases provides insights into their evolutionary trajectories and importance for plant metabolism.

FRONTIERS IN PLANT SCIENCE (2021)

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Article Biochemistry & Molecular Biology

Novel Quercetin Derivative of 3,7-Dioleylquercetin Shows Less Toxicity and Highly Potent Tyrosinase Inhibition Activity

Moon-Hee Choi et al.

Summary: A novel quercetin derivative, 3,7-dioleylquercetin, was synthesized and showed low cytotoxicity in skin-whitening applications. It acts as a competitive inhibitor, inhibits melanin-related gene expression, and is suitable for development of novel skin-whitening agents.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

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Article Agriculture, Multidisciplinary

Chelation of Iron and Copper by Quercetin B-Ring Methyl Metabolites, Isorhamnetin and Tamarixetin, and Their Effect on Metal-Based Fenton Chemistry

Zuzana Lomozova et al.

Summary: Quercetin metabolites show differences in their interactions with transition metals, affecting processes like the Fenton reaction and hemolysis. Isorhamnetin is more effective in attenuating copper-triggered hemolysis.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2021)

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Article Biochemical Research Methods

Mechanism of reactivation of the peroxidase catalytic activity of human cyclooxygenases by reducing cosubstrate quercetin*

Chengxi Yang et al.

Summary: The study shows that flavonoids like quercetin can reactivate the peroxidase activity of COX-1/2 at nanomolar concentrations, with the C-3'-OH group of quercetin effectively donating electrons to heme Fe ion. This mechanistic explanation could aid in the rational design of drugs targeting the peroxidase sites of COX-1/2.

JOURNAL OF MOLECULAR GRAPHICS & MODELLING (2021)

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Review Biochemistry & Molecular Biology

Protein Adducts and Protein Oxidation as Molecular Mechanisms of Flavonoid Bioactivity

P. Matthew Joyner

Summary: Flavonoids have complex chemistry in aqueous solutions at neutral pH, with acidic protons and redox activity, and they exhibit high affinity interactions with proteins. Under neutral pH conditions, flavonoids may exert their bioactivity in cells by forming protein-flavonoid adducts or inducing protein oxidation.

MOLECULES (2021)

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Review Chemistry, Medicinal

Quercetin as a protective agent for liver diseases: A comprehensive descriptive review of the molecular mechanism

Xingtao Zhao et al.

Summary: Quercetin, as a major flavonoid compound, exhibits good pharmacological activities in treating liver diseases by influencing multiple targets and pathways, including anti-fat accumulation, anti-inflammatory, and antioxidant effects. It inhibits inflammation mainly through NF-kappa B/TLR/NLRP3, reduces oxidative stress mediated by PI3K/Nrf2, and affects autophagy activation by mTOR. The compound also shows different mechanisms of action at different stages of liver diseases, targeting factors related to PPAR, UCP, and PLIN2 in steatosis, and inhibiting stromal ECM deposition in fibrosis, among others.

PHYTOTHERAPY RESEARCH (2021)

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Review Plant Sciences

The role of quercetin in plants

Priyanka Singh et al.

Summary: Flavonoids are a special category of hydroxylated phenolic compounds with an aromatic ring structure, and quercetin is a subclass known for its bioactive properties in promoting plant physiological processes and antioxidant functions. Quercetin plays a crucial role in enhancing various physiological and biochemical processes in plants under stress and non-stress conditions, while also showing potential in mitigating biotic and abiotic stresses such as salt, heavy metal, and UV stress. Additionally, the biosynthesis of flavonoids, their signaling pathways, and quercetin's involvement in plant signaling are discussed in this review.

PLANT PHYSIOLOGY AND BIOCHEMISTRY (2021)

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Article Multidisciplinary Sciences

Long-term treatment with senolytic drugs Dasatinib and Quercetin ameliorates age-dependent intervertebral disc degeneration in mice

Emanuel J. Novais et al.

Summary: Intervertebral disc degeneration is a common issue in the elderly population, leading to chronic back pain and disability. The study shows that long term treatment with senolytic compounds Dasatinib and Quercetin can reduce disc senescence burden and ameliorate age-dependent degeneration in mice.

NATURE COMMUNICATIONS (2021)

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Review Biochemistry & Molecular Biology

Transit and Metabolic Pathways of Quercetin in Tubular Cells: Involvement of Its Antioxidant Properties in the Kidney

Daniel Munoz-Reyes et al.

Summary: Quercetin, a flavonoid compound with antioxidant properties, is considered to have therapeutic potential in protecting against oxidative stress, particularly in the kidney. However, the specific metabolic processes and effects in the kidney remain unclear.

ANTIOXIDANTS (2021)

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Article Chemistry, Multidisciplinary

Molecular Simulation Study on the Interaction between Tyrosinase and Flavonoids from Sea Buckthorn

Xiaofang Li et al.

Summary: The study demonstrates that isorhamnetin, kaempferol, myricetin, and quercetin in sea buckthorn can interact with tyrosinase, inhibiting its catalytic activity. Among these compounds, quercetin shows the lowest binding energy and the most stable complex with tyrosinase, potentially serving as a natural inhibitor for tyrosinase.

ACS OMEGA (2021)

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Review Biochemistry & Molecular Biology

The Flavonoid Biosynthesis Network in Plants

Weixin Liu et al.

Summary: Flavonoids are important secondary metabolites found in plants, with biosynthesis pathways that have been extensively researched. This review provides a comprehensive overview of the biosynthetic pathways of flavonoids in plants, offering a detailed map of the process.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2021)

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Review Food Science & Technology

A minireview of quercetin: from its metabolism to possible mechanisms of its biological activities

Hande Gul Ulusoy et al.

CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION (2020)

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Review Pharmacology & Pharmacy

Enhancing the potential preclinical and clinical benefits of quercetin through novel drug delivery systems

Rubiya Khursheed et al.

DRUG DISCOVERY TODAY (2020)

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Review Food Science & Technology

Bioactivity of dietary polyphenols: The role of metabolites

Simon Vlad Luca et al.

CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION (2020)

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Review Medicine, Research & Experimental

Pharmacological basis and new insights of quercetin action in respect to its anti-cancer effects

Si-Min Tang et al.

BIOMEDICINE & PHARMACOTHERAPY (2020)

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Review Biotechnology & Applied Microbiology

A Review on Structure, Modifications and Structure-Activity Relation of Quercetin and Its Derivatives

Rubin Thapa Magar et al.

JOURNAL OF MICROBIOLOGY AND BIOTECHNOLOGY (2020)

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Article Chemistry, Applied

Low nanomolar concentrations of a quercetin oxidation product, which naturally occurs in onion peel, protect cells against oxidative damage

Jocelyn Fuentes et al.

FOOD CHEMISTRY (2020)

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Article Biochemistry & Molecular Biology

Personalized Mapping of Drug Metabolism by the Human Gut Microbiome

Bahar Javdan et al.

CELL (2020)

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Article Chemistry, Physical

Mechanistic insights into the crucial roles of Glu76 residue in nickel-dependent quercetin 2,4-dioxygenase for quercetin oxidative degradation

Xueyuan Yan et al.

JOURNAL OF CATALYSIS (2020)

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Review Biochemistry & Molecular Biology

Redox reactions of heme proteins with flavonoids

Lidia Gebicka

JOURNAL OF INORGANIC BIOCHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Decomposition of Flavonols in the Presence of Saliva

Malgorzata Rogozinska et al.

APPLIED SCIENCES-BASEL (2020)

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Review Cell Biology

Quercetin: Its Main Pharmacological Activity and Potential Application in Clinical Medicine

Dengyu Yang et al.

OXIDATIVE MEDICINE AND CELLULAR LONGEVITY (2020)

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Review Microbiology

Breakthroughs in the discovery and use of different peroxidase isoforms of microbial origin

Pontsho Patricia Twala et al.

AIMS MICROBIOLOGY (2020)

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Review Food Science & Technology

MicroRNAs as molecular targets of quercetin and its derivatives underlying their biological effects: A preclinical strategy

Dan Wang et al.

CRITICAL REVIEWS IN FOOD SCIENCE AND NUTRITION (2019)

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Article Agriculture, Multidisciplinary

Intracellular Polyphenols: How Little We Know

Joe A. Vinson

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2019)

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Article Multidisciplinary Sciences

Separating host and microbiome contributions to drug pharmacokinetics and toxicity

Michael Zimmermann et al.

SCIENCE (2019)

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Article Chemistry, Applied

Five individual polyphenols as tyrosinase inhibitors: Inhibitory activity, synergistic effect, action mechanism, and molecular docking

Qun Yu et al.

FOOD CHEMISTRY (2019)

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Review Pharmacology & Pharmacy

Predicting and Understanding the Human Microbiome's Impact on Pharmacology

Reese Hitchings et al.

TRENDS IN PHARMACOLOGICAL SCIENCES (2019)

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Article Biochemistry & Molecular Biology

Structure-Dependent Modulation of Substrate Binding and Biodegradation Activity of Pirin Proteins toward Plant Flavonols

Bin Guo et al.

ACS CHEMICAL BIOLOGY (2019)

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Article Biochemistry & Molecular Biology

Redox properties of individual quercetin moieties

Eva Hermankova et al.

FREE RADICAL BIOLOGY AND MEDICINE (2019)

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Review Nutrition & Dietetics

Dietary Quercetin and Kaempferol: Bioavailability and Potential Cardiovascular-Related Bioactivity in Humans

Wijdan M. Dabeek et al.

NUTRIENTS (2019)

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Article Chemistry, Multidisciplinary

Theoretical Study of the Antioxidant Activity of Quercetin Oxidation Products

Alejandro Vasquez-Espinal et al.

FRONTIERS IN CHEMISTRY (2019)

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Review Food Science & Technology

Bioavailability of Quercetin in Humans with a Focus on Interindividual Variation

A. Filipa Almeida et al.

COMPREHENSIVE REVIEWS IN FOOD SCIENCE AND FOOD SAFETY (2018)

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Review Pharmacology & Pharmacy

Insights into the intestinal bacterial metabolism of flavonoids and the bioactivities of their microbe-derived ring cleavage metabolites

Xinchi Feng et al.

DRUG METABOLISM REVIEWS (2018)

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Review Food Science & Technology

Quercetin and iron metabolism: What we know and what we need to know

Lin Xiao et al.

FOOD AND CHEMICAL TOXICOLOGY (2018)

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Article Agriculture, Multidisciplinary

Inhibitive Effects of Quercetin on Myeloperoxidase-Dependent Hypochlorous Acid Formation and Vascular Endothelial Injury

Naihao Lu et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2018)

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Article Biotechnology & Applied Microbiology

Pirin: A novel redox-sensitive modulator of primary and secondary metabolism in Streptomyces

Adelfia Tala et al.

METABOLIC ENGINEERING (2018)

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Article Chemistry, Physical

Insights into the dioxygen activation and catalytic mechanism of the nickel-containing quercetinase

Hong Li et al.

CATALYSIS SCIENCE & TECHNOLOGY (2018)

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Article Food Science & Technology

Formation and biological targets of botanical o-quinones

Judy L. Bolton et al.

FOOD AND CHEMICAL TOXICOLOGY (2018)

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Article Multidisciplinary Sciences

Flavonols control pollen tube growth and integrity by regulating ROS homeostasis during high-temperature stress

Joelle K. Muhlemann et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2018)

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Review Biochemistry & Molecular Biology

Oxygen activation by mononuclear Mn, Co, and Ni centers in biology and synthetic complexes

Adam T. Fiedler et al.

JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY (2017)

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Article Chemistry, Applied

Quercetin and related flavonoids conserve their antioxidant properties despite undergoing chemical or enzymatic oxidation

Elias Atala et al.

FOOD CHEMISTRY (2017)

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Article Food Science & Technology

Quercetin as a tyrosinase inhibitor: Inhibitory activity, conformational change and mechanism

Meihui Fan et al.

FOOD RESEARCH INTERNATIONAL (2017)

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Article Agriculture, Multidisciplinary

Quercetin Oxidation Paradoxically Enhances its Antioxidant and Cytoprotective Properties

Jocelyn Fuentes et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2017)

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Article Chemistry, Analytical

Systematization of the results of the chromatography-mass spectrometry identification of the products of quercetin oxidation by atmospheric oxygen in aqueous solutions

I. G. Zenkevich et al.

JOURNAL OF ANALYTICAL CHEMISTRY (2017)

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Article Biochemistry & Molecular Biology

Redox-Specific Allosteric Modulation of the Conformational Dynamics of κB DNA by Pirin in the NF-κB Supramolecular Complex

Charles Adeniran et al.

BIOCHEMISTRY (2017)

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Article Chemistry, Multidisciplinary

Laccase-Mediated Enhancement of the Antioxidant Activity of Propolis and Poplar Bud Exudates

Lorenzo Botta et al.

ACS OMEGA (2017)

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Article Chemistry, Multidisciplinary

Quercetin 2,4-Dioxygenase Activates Dioxygen in a Side-On O2-Ni Complex

Jae-Hun Jeoung et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2016)

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Review Pharmacology & Pharmacy

Molecular targets of quercetin with anti-inflammatory properties in atopic dermatitis

Vengadeshprabhu Karuppagounder et al.

DRUG DISCOVERY TODAY (2016)

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Article Chemistry, Inorganic & Nuclear

Dioxygen Binding, Activation, and Reduction to H2O by Cu Enzymes

Edward I. Solomon

INORGANIC CHEMISTRY (2016)

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Article Multidisciplinary Sciences

In Vitro Antioxidant versus Metal Ion Chelating Properties of Flavonoids: A Structure-Activity Investigation

Sabri Ahmed Cherrak et al.

PLOS ONE (2016)

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Article Biochemistry & Molecular Biology

Independent evolution of four heme peroxidase superfamilies

Marcel Zamocky et al.

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS (2015)

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Review Biotechnology & Applied Microbiology

Microbial biotransformation of bioactive flavonoids

Hui Cao et al.

BIOTECHNOLOGY ADVANCES (2015)

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Review Biochemistry & Molecular Biology

Three-dimensional structures of laccases

N. Hakulinen et al.

CELLULAR AND MOLECULAR LIFE SCIENCES (2015)

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Review Chemistry, Medicinal

Quercetin: A flavonol with multifaceted therapeutic applications?

Gabriele D'Andrea

FITOTERAPIA (2015)

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Review Chemistry, Applied

Role of quercetin as an alternative for obesity treatment: You are what you eat!

Seyed Fazel Nabavi et al.

FOOD CHEMISTRY (2015)

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Review Agriculture, Multidisciplinary

Degradation of Curcumin: From Mechanism to Biological Implications

Claus Schneider et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2015)

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Review Biochemistry & Molecular Biology

Endogenous and exogenous mediators of quercetin bioavailability

Yi Guo et al.

JOURNAL OF NUTRITIONAL BIOCHEMISTRY (2015)

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Article Chemistry, Physical

Computational Study of Catalytic Reaction of Quercetin 2,4-Dioxygenase

Tom Saito et al.

JOURNAL OF PHYSICAL CHEMISTRY B (2015)

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Review Biochemistry & Molecular Biology

Quercetin and related polyphenols: new insights and implications for their bioactivity and bioavailability

Kyuichi Kawabata et al.

FOOD & FUNCTION (2015)

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Review Chemistry, Multidisciplinary

Properties and applications of flavonoid metal complexes

Maria M. Kasprzak et al.

RSC ADVANCES (2015)

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Review Biochemistry & Molecular Biology

Tyrosinase: The four oxidation states of the active site and their relevance to enzymatic activation, oxidation and inactivation

Christopher A. Ramsden et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2014)

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Review Biochemistry & Molecular Biology

Flavonoids and Melanins: A Common Strategy across Two Kingdoms

Giorgia Carletti et al.

INTERNATIONAL JOURNAL OF BIOLOGICAL SCIENCES (2014)

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Article Agriculture, Multidisciplinary

Oxidative Degradation of Quercetin with Hydrogen Peroxide Using Continuous-Flow Kinetic Electrospray-Ion Trap-Time-of-Flight Mass Spectrometry

Jeremy S. Barnes et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2014)

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Article Chemistry, Multidisciplinary

Mechanism of the Reduction of the Native Intermediate in the Multicopper Oxidases: Insights into Rapid Intramolecular Electron Transfer in Turnover

David E. Heppner et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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Article Multidisciplinary Sciences

Pirin1 (PRN1) Is a Multifunctional Protein that Regulates Quercetin, and Impacts Specific Light and UV Responses in the Seed-to-Seedling Transition of Arabidopsis thaliana

Danielle A. Orozco-Nunnelly et al.

PLOS ONE (2014)

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Article Pharmacology & Pharmacy

The complex degradation and metabolism of quercetin in rat hepatocyte incubations

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XENOBIOTICA (2014)

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Review Chemistry, Inorganic & Nuclear

Structure and function of atypically coordinated enzymatic mononuclear non-heme-Fe(II) centers

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COORDINATION CHEMISTRY REVIEWS (2013)

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Article Biochemistry & Molecular Biology

Bioavailability of Quercetin: Problems and Promises

X. Cai et al.

CURRENT MEDICINAL CHEMISTRY (2013)

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Article Chemistry, Physical

Deprotonation Mechanism and Acidity Constants in Aqueous Solution of Flavonols: a Combined Experimental and Theoretical Study

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JOURNAL OF PHYSICAL CHEMISTRY B (2013)

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Article Biochemical Research Methods

Thermally Accelerated Oxidative Degradation of Quercetin Using Continuous Flow Kinetic Electrospray-Ion Trap-Time of Flight Mass Spectrometry

Jeremy S. Barnes et al.

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY (2013)

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Review Chemistry, Medicinal

A New Perspective on the Quercetin Paradox in Male Reproductive Dysfunction

Pavitra Ranawat et al.

PHYTOTHERAPY RESEARCH (2013)

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Review Plant Sciences

The flavonoid biosynthetic pathway in Arabidopsis: Structural and genetic diversity

Kazuki Saito et al.

PLANT PHYSIOLOGY AND BIOCHEMISTRY (2013)

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Article Multidisciplinary Sciences

Pirin is an iron-dependent redox regulator of NF-κB

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PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2013)

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Review Biotechnology & Applied Microbiology

Ring-Cleaving Dioxygenases with a Cupin Fold

Susanne Fetzner

APPLIED AND ENVIRONMENTAL MICROBIOLOGY (2012)

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Article Pharmacology & Pharmacy

The flavonoid quercetin in disease prevention and therapy: Facts and fancies

Maria Russo et al.

BIOCHEMICAL PHARMACOLOGY (2012)

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Article Chemistry, Multidisciplinary

The oxidation of natural flavonoid quercetin

Romana Sokolova et al.

CHEMICAL COMMUNICATIONS (2012)

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Article Agriculture, Multidisciplinary

UHPLC-(ESI)QTOF MS/MS Profiling of Quercetin Metabolites in Human Plasma Postconsumption of Applesauce Enriched with Apple Peel and Onion

Jihyun Lee et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2012)

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Review Plant Sciences

Life or death: Neuroprotective and anticancer effects of quercetin

Federico Dajas

JOURNAL OF ETHNOPHARMACOLOGY (2012)

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Review Plant Sciences

Flavonols: old compounds for old roles

Susanna Pollastri et al.

ANNALS OF BOTANY (2011)

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Review Chemistry, Medicinal

Antioxidant and prooxidant properties of flavonoids

D. Prochazkova et al.

FITOTERAPIA (2011)

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Article Biochemistry & Molecular Biology

Polyphenols activate Nrf2 in astrocytes via H2O2, semiquinones, and quinones

Hilla Erlank et al.

FREE RADICAL BIOLOGY AND MEDICINE (2011)

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Review Biochemistry & Molecular Biology

Mechanisms of catalase activity of heme peroxidases

Jutta Vlasits et al.

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS (2010)

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Review Biotechnology & Applied Microbiology

The rutin catabolic pathway with special emphasis on quercetinase

Sylvain Tranchimand et al.

BIODEGRADATION (2010)

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Article Multidisciplinary Sciences

Structural Basis for Certain Naturally Occurring Bioflavonoids to Function as Reducing Co-Substrates of Cyclooxygenase I and II

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PLOS ONE (2010)

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Article Biochemistry & Molecular Biology

UVA and UVB radiation-induced oxidation products of quercetin

Brian M. Fahlman et al.

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B-BIOLOGY (2009)

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Review Biochemistry & Molecular Biology

Dietary phenolics: chemistry, bioavailability and effects on health

Alan Crozier et al.

NATURAL PRODUCT REPORTS (2009)

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Article Chemistry, Medicinal

Flavonoids as substrates and inhibitors of myeloperoxidase: Molecular actions of aglycone and metabolites

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CHEMICAL RESEARCH IN TOXICOLOGY (2008)

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Article Agriculture, Multidisciplinary

Comparative Analysis of Quercetin Oxidation by Electrochemical, Enzymatic, Autoxidation, and Free Radical Generation Techniques: A Mechanistic Study

Ailing Zhou et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2008)

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Article Biochemistry & Molecular Biology

Investigation on biocatalytic properties of a peroxidase-active homogenate from onion solid wastes: An insight into quercetin oxidation mechanism

Ali Osman et al.

PROCESS BIOCHEMISTRY (2008)

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Review Biochemistry & Molecular Biology

Nutritionally essential fatty acids and biologically indispensable cyclooxygenases

William L. Smith

TRENDS IN BIOCHEMICAL SCIENCES (2008)

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Review Agriculture, Multidisciplinary

Onions: A source of unique dietary flavonoids

Rune Slimestad et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2007)

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Article Electrochemistry

Electrochemical degradation of quercetin: Isolation and structural elucidation of the degradation products

Ailing Zhou et al.

ELECTROCHEMISTRY COMMUNICATIONS (2007)

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Article Biochemistry & Molecular Biology

Molecular simulations bring new insights into flavonoid/quercetinase interaction modes

Sebastien Fiorucci et al.

PROTEINS-STRUCTURE FUNCTION AND BIOINFORMATICS (2007)

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Article Chemistry, Multidisciplinary

The effect of a water molecule on the mechanism of formation of compound 0 in horseradish peroxidase

Etienne Derat et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2007)

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Article Biochemistry & Molecular Biology

Identification of the products of oxidation of quercetin by air oxygen at ambient temperature

Igor G. Zenkevich et al.

MOLECULES (2007)

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Review Plant Sciences

Flavonoid oxidation in plants: from biochemical properties to physiological functions

Lucille Pourcel et al.

TRENDS IN PLANT SCIENCE (2007)

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Review Biochemistry & Molecular Biology

Flavonoids: Hemisynthesis, reactivity, characterization and free radical scavenging activity

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MOLECULES (2007)

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Article Chemistry, Applied

A DFT study of the reactivity of OH groups in quercetin and taxifolin antioxidants: The specificity of the 3-OH site

P Trouillas et al.

FOOD CHEMISTRY (2006)

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Article Agriculture, Multidisciplinary

Antibacterial and antioxidant activities of quercetin oxidation products from yellow onion (Allium cepa) skin

Freddy A. Ramos et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2006)

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Article Agriculture, Multidisciplinary

Gas and liquid phase acidity of natural antioxidants

M Leopoldini et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2006)

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Article Biochemistry & Molecular Biology

Oxidative modification of quercetin by hemeproteins

EM Cherviakovsky et al.

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS (2006)

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Review Plant Sciences

Microbial and enzymatic transformations of flavonoids

S Das et al.

JOURNAL OF NATURAL PRODUCTS (2006)

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Article Biochemical Research Methods

Effect of thermal processing on the flavonols rutin and quercetin

Nadja Buchner et al.

RAPID COMMUNICATIONS IN MASS SPECTROMETRY (2006)

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Article Biochemistry & Molecular Biology

Enzymatic polymerization of phenolic compounds using laccase and tyrosinase from Ustilago maydis

Rosa Martha Desentis-Mendoza et al.

BIOMACROMOLECULES (2006)

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Article Chemistry, Multidisciplinary

Electrochemical oxidation of quercetin in hydro-alcoholic solution

AK Timbola et al.

JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY (2006)

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Article Chemistry, Medicinal

Formation of transient covalent protein and DNA adducts by quercetin in cells with and without oxidative enzyme activity

H van der Woude et al.

CHEMICAL RESEARCH IN TOXICOLOGY (2005)

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Article Biochemistry & Molecular Biology

Structural and biochemical analysis reveal pirins to possess quercetinase activity

M Adams et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2005)

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Article Biochemistry & Molecular Biology

The crystal structure of a quercetin 2,3-dioxygenase from Bacillus subtilis suggests modulation of enzyme activity by a change in the metal ion at the active site(s)

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BIOCHEMISTRY (2005)

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Article Biochemistry & Molecular Biology

Crystal structure of human pirin - An iron-binding nuclear protein and transcription cofactor

H Pang et al.

JOURNAL OF BIOLOGICAL CHEMISTRY (2004)

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Article Chemistry, Inorganic & Nuclear

Hybrid DFT study of the mechanism of quercetin 2,3-dioxygenase

PEM Siegbahn

INORGANIC CHEMISTRY (2004)

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Article Biochemical Research Methods

Study of the reaction products of flavonols with 2,2-diphenyl-1-picrylhydrazyl using liquid chromatography coupled with negative electrospray ionization tandem mass spectrometry

E Hvattum et al.

JOURNAL OF MASS SPECTROMETRY (2004)

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Article Chemistry, Medicinal

In vitro flavon-3-ol oxidation mediated by a B ring hydroxylation pattern

V Krishnamachari et al.

CHEMICAL RESEARCH IN TOXICOLOGY (2004)

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Article Biochemistry & Molecular Biology

Oxidation products of quercetin catalyzed by mushroom tyrosinase

I Kubo et al.

BIOORGANIC & MEDICINAL CHEMISTRY (2004)

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Article Agriculture, Multidisciplinary

Kinetic study of the oxidation of quercetin by mushroom tyrosinase

LG Fenoll et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2003)

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Article Multidisciplinary Sciences

Anaerobic enzyme-substrate structures provide insight into the reaction mechanism of the copper-dependent quercetin 2,3-dioxygenase

RA Steiner et al.

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2002)

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Article Agriculture, Multidisciplinary

Radiolysis of quercetin in methanol solution: Observation of depside formation

A Marfak et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2002)

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Article Agriculture, Multidisciplinary

Flavonoid oxidation by the radical generator AIBN:: A unified mechanism for quercetin radical scavenging

V Krishnamachari et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2002)

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Article Agriculture, Multidisciplinary

Kinetics of mushroom tyrosinase inhibition by quercetin

QX Chen et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2002)

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Article Biochemical Research Methods

Assay and analysis for anti- and pro-oxidative effects of ascorbic acid on DNA with the bulk acoustic wave impedance technique

B Guo et al.

ANALYTICAL BIOCHEMISTRY (2002)

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Article Multidisciplinary Sciences

The catalytic pathway of horseradish peroxidase at high resolution

GI Berglund et al.

NATURE (2002)

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Article Chemistry, Applied

An investigation on structural aspects influencing product formation in enzymic and chemical oxidation of quercetin and related flavonols

DP Makris et al.

FOOD CHEMISTRY (2002)

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Article Agriculture, Multidisciplinary

Quercetin derivatives are deconjugated and converted to hydroxyphenylacetic acids but not methylated by human fecal flora in vitro

AM Aura et al.

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY (2002)

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Review Nutrition & Dietetics

Dietary flavonols: Chemistry, food content, and metabolism

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NUTRITION (2002)

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Article Chemistry, Organic

Kinetics and mechanism of the base-catalyzed oxygenation of flavonol in DMSO-H2O solution

É Balogh-Hergovich et al.

JOURNAL OF ORGANIC CHEMISTRY (2001)

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Article Nutrition & Dietetics

Carbon dioxide is the major metabolite of quercetin in humans

T Walle et al.

JOURNAL OF NUTRITION (2001)

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Article Biochemical Research Methods

Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry

N Fabre et al.

JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY (2001)

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Article Plant Sciences

Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus

M Hosny et al.

JOURNAL OF NATURAL PRODUCTS (2001)

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Article Biochemistry & Molecular Biology

Peroxidative metabolism of apigenin and naringenin versus luteolin and quercetin: Glutathione oxidation and conjugation

G Galati et al.

FREE RADICAL BIOLOGY AND MEDICINE (2001)

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Review Plant Sciences

Flavonoids as antioxidants

PG Pietta

JOURNAL OF NATURAL PRODUCTS (2000)

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Article Biochemistry & Molecular Biology

Peroxidase-catalyzed formation of quercetin quinone methide-glutathione adducts

HM Awad et al.

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS (2000)

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Article Chemistry, Medicinal

Regioselectivity and reversibility of the glutathione conjugation of quercetin quinone methide

MG Boersma et al.

CHEMICAL RESEARCH IN TOXICOLOGY (2000)

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Article Chemistry, Organic

Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media

G Jungbluth et al.

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 (2000)

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Recent insights into oxidative metabolism of quercetin: catabolic profiles, degradation pathways, catalyzing metalloenzymes and molecular mechanisms

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