galangin and myricetin

Topics: Binding Sites; Circular Dichroism; Flavonols; Kaempferols; Molecular Docking Simulation; Protein Binding; Quercetin; Spectrometry, Fluorescence; Thermodynamics; Transferrin

Single-stranded DNA (ssDNA)-binding protein (SSB) plays a crucial role in DNA replication, repair, and recombination as well as replication fork restarts. SSB is essential for cell survival and, thus, is an attractive target for potential antipathogen chemotherapy. Whether naturally occurring products can inhibit SSB remains unknown. In this study, the effect of the flavonols myricetin, quercetin, kaempferol, and galangin on the inhibition of

Topics: Bacterial Proteins; Crystallography, X-Ray; DNA-Binding Proteins; Flavonoids; Flavonols; Kaempferols; Models, Molecular; Protein Conformation; Pseudomonas aeruginosa; Quercetin

Flavonols have been studied extensively because of their interesting biological activities and excited-state intramolecular proton transfer (ESIPT) behavior. Galangin, kaempferol, quercetin, and myricetin are structurally related flavonols that differ only in the number of B-ring hydroxyl substituents. In this work, we have carried out a detailed study on the photophysical behavior of these structurally related flavonols in various solvents and a 1,2-dimyristoyl-

Topics: Dimyristoylphosphatidylcholine; Flavonoids; Flavonols; Hydroxylation; Kaempferols; Quercetin; Solvents

The angiotensin-converting enzyme (ACE)-related carboxypeptidase, ACE-II, is a type I integral membrane protein of 805 amino acids that contains 1 HEXXH-E zinc binding consensus sequence. ACE-II has been implicated in the regulation of heart function and also as a functional receptor for the coronavirus that causes the severe acute respiratory syndrome (SARS). In this study, the potential of some flavonoids presents in propolis to bind to ACE-II receptors was calculated with in silico. Binding constants of ten flavonoids, caffeic acid, caffeic acid phenethyl ester, chrysin, galangin, myricetin, rutin, hesperetin, pinocembrin, luteolin and quercetin were measured using the AutoDock 4.2 molecular docking program. And also, these binding constants were compared to reference ligand of MLN-4760. The results are shown that rutin has the best inhibition potentials among the studied molecules with high binding energy - 8.04 kcal/mol, and it is followed by myricetin, quercetin, caffeic acid phenethyl ester and hesperetin. However, the reference molecule has binding energy of - 7.24 kcal/mol. In conclusion, the high potential of flavonoids in ethanolic propolis extracts to bind to ACE-II receptors indicates that this natural bee product has high potential for COVID-19 treatment, but this needs to be supported by experimental studies.

Topics: Angiotensin-Converting Enzyme 2; Animals; Bees; Caffeic Acids; COVID-19 Drug Treatment; Flavanones; Flavonoids; Hesperidin; Humans; Luteolin; Molecular Docking Simulation; Phenylethyl Alcohol; Plant Extracts; Propolis; Quercetin; Rutin

Zika virus (ZIKV) infection is a global public health problem due to its rapid spread and the possibility of causing microcephaly. Currently, no specific antivirals against ZIKV are available for treatment. In the present study, several flavonoids (galangin, kaempferide, quercetin, myricetin and EGCG) were found to reduce ZIKV induced plaques and viral RNA copies with negligible cytotoxic effects on host cells. In addition, inhibition of ZIKV propagation by flavonoids showed structure-activity relationship. Our results demonstrate flavonoids as inhibitors of ZIKV entry and NS2B-NS3 protease. Hence, these flavonoids could be used as potential bifunctional drugs for treating ZIKV infections.

Topics: Animals; Antiviral Agents; Chlorocebus aethiops; Flavonoids; Humans; Kaempferols; Molecular Structure; Quercetin; Serine Endopeptidases; Structure-Activity Relationship; Vero Cells; Viral Nonstructural Proteins; Viral Proteins; Virus Internalization; Virus Replication; Zika Virus; Zika Virus Infection

The inhibition of recombinant CpLIP2 lipase/acyltransferase from

Topics: Acyltransferases; Algorithms; Flavonoids; Flavonols; Hydrolysis; Hydroxylation; Kaempferols; Models, Theoretical; Molecular Structure; Orlistat; Protein Binding; Quercetin; Spectrometry, Fluorescence; Structure-Activity Relationship; Thermodynamics

Flavonoids, a class of polyphenols are known to be effective inducers of apoptosis and cytotoxicity in cancer cells. It is believed that antioxidant activity of polyphenols cannot fully account for induction of apoptosis and chemotherapeutic prevention in various cancers. In this article, by employing single cell alkaline gel electrophoresis (comet assay), we established that antioxidants, flavonoids such as (myricetin=MN, fisetin=FN, quercetin=QN, kaempferol=KL and galangin=GN) can cause cellular DNA breakage, also act as pro-oxidant in presence of transition metal ion such as copper. It was observed that the extent of cellular DNA breakage was found significantly higher in presence of copper. Hydroxyl radicals are generated as a sign of flavonoids' pro-oxidant nature through redox recycling of copper ions. Further, a dose-dependent inhibition of proliferation of breast cancer cells MDA-MB-231 by MN was found leading to pro-oxidant cell death, as assessed by MTT assay. Since levels of copper are considerably elevated in tissue, cell and serum during various malignancies, suggesting that cancer cells would be more subject to copper induced oxidative DNA breakage. Such a copper dependent pro-oxidant cytotoxic mechanism better explains the anticancer activity and preferential cytotoxicity of dietary phytochemicals against cancer cells.

Topics: Antineoplastic Agents, Phytogenic; Apoptosis; Cations, Divalent; Cell Line, Tumor; Copper; DNA Damage; Epithelial Cells; Flavonoids; Flavonols; Humans; Kaempferols; Oxidants; Oxidation-Reduction; Quercetin; Reactive Oxygen Species

Isolated and structurally confirmed, eleven flavonoids from propolis were examined for their cytotoxicity toward human colon cancer and human breast cancer cells. Their effect on induction of apoptosis and their antioxidative activities were also evaluated. Six flavonoids induced cytotoxic effects in both cell lines. Luteolin had a marked effect on both cell lines, especially on HCT-116 cells (IC

Topics: Antineoplastic Agents; Antioxidants; Apitherapy; Apoptosis; Breast; Breast Neoplasms; Cell Line, Tumor; Colon; Colonic Neoplasms; Female; Flavonoids; HCT116 Cells; Humans; Luteolin; Nitrites; Oxidants; Oxidation-Reduction; Plant Extracts; Propolis; Superoxides

The

Topics: Antineoplastic Agents, Phytogenic; Apigenin; Cell Proliferation; Cucurbitaceae; Cucurbitacins; Female; Flavanones; Flavonoids; Fruit; HeLa Cells; Humans; Inhibitory Concentration 50; Phloretin; Phytochemicals; Plant Extracts; Quercetin; Rutin; Uterine Cervical Neoplasms

It has been reported that quercetin is an activator of rat vitamin D receptor (rVDR). However, the conclusion was based on experiments performed without all the appropriate control groups, raising the possibility of a false-positive finding. Furthermore, distinct differences exist in the chemical structures of quercetin and 1α,25-dihydroxyvitamin D3, which is a prototypic agonist of VDR. Therefore, we investigated systematically whether quercetin and other flavonols are agonists of rVDR, mouse VDR (mVDR), or human VDR (hVDR). Quercetin, 3-hydroxyflavone, galangin, datiscetin, kaempferol, morin, isorhamnetin, tamarixetin, myricetin, and syringetin did not activate rVDR, mVDR, or hVDR in HEK-293 and HepG2 cells transfected with the corresponding receptor expression plasmid and either the secreted phosphoprotein 1 (Spp1) or cytochrome P450 24A1 (CYP24A1) reporter plasmid, when compared to the respective empty vector control group transfected with one or the other reporter plasmid and treated with one of the flavonols. Control analysis indicated that lithocholic acid and 1α,25-dihydroxyvitamin D3, but not rifampicin, activated rVDR, mVDR, and hVDR. As shown in transfected HEK293 and HepG2 cells, the flavonols did not influence hVDR ligand binding domain transactivation, steroid receptor coactivator-1 recruitment, or hVDR target gene expression (transient receptor potential cation channel 6 and CYP24A1) in hVDR-expressing Caco-2 or LS180 cells. The cumulative data from the cell-based experiments were corroborated by results obtained from molecular docking analysis. In conclusion, quercetin, 3-hydroxyflavone, galangin, datiscetin, kaempferol, morin, isorhamnetin, tamarixetin, myricetin, and syringetin are not agonists of rVDR, mVDR, or hVDR, as judged by cell-based and in silico evidence.

Topics: Animals; Caco-2 Cells; Calcitriol; Disaccharides; Flavonoids; Gene Expression Regulation; HEK293 Cells; Hep G2 Cells; Humans; Kaempferols; Mice; Molecular Docking Simulation; Osteopontin; Quercetin; Receptors, Calcitriol; Structure-Activity Relationship; Transgenes; Vitamin D3 24-Hydroxylase

Epidemiological studies have linked dietary consumption of plant polyphenols with lower incidence of various cancers. In particular, flavonoids (present in onion, tomato and other plant sources) induce apoptosis and cytotoxicity in cancer cells. These can therefore be used as lead compounds for the synthesis of novel anticancer drugs with greater bioavailability. In the present study, we examined the chemical basis of cytotoxicity of flavonoids by studying the structure-activity relationship of myricetin (MN), fisetin (FN), quercetin (QN), kaempferol (KL) and galangin (GN). Using single cell alkaline gel electrophoresis (comet assay), we established the relative efficiency of cellular DNA breakage as MN > FN > QN > KL > GN. Also, we determined that the cellular DNA breakage was the result of mobilization of chromatin-bound copper ions and the generation of reactive oxygen species. The relative DNA binding affinity order was further confirmed using molecular docking and thermodynamic studies through the interaction of flavonoids with calf thymus DNA. Our results suggest that novel anti-cancer molecules should have ortho-dihydroxy groups in B-ring and hydroxyl groups at positions 3 and 5 in the A-ring system. Additional hydroxyl groups at other positions further enhance the cellular cytotoxicity of the flavonoids.

Topics: Antineoplastic Agents, Phytogenic; Cations, Divalent; Chelating Agents; Comet Assay; Copper; DNA; DNA Fragmentation; Flavonoids; Flavonols; Humans; Kaempferols; Leukocytes, Mononuclear; Molecular Docking Simulation; Oxidation-Reduction; Primary Cell Culture; Quercetin; Reactive Oxygen Species; Structure-Activity Relationship

Rheumatoid arthritis (RA) patients usually exhibit immune complex (IC) deposition and increased neutrophil activation in the joint. In this study, we assessed how four flavonols (galangin, kaempferol, quercetin, and myricetin) modulate the effector functions of healthy individuals' and active RA patients' IC-stimulated neutrophils. We measured superoxide anion and total reactive oxygen species production using lucigenin (CL-luc)- and luminol (CL-lum)-enhanced chemiluminescence assays, respectively. Galangin, kaempferol, and quercetin inhibited CL-lum to the same degree (mean IC50=2.5 μM). At 2.5 μM, quercetin and galangin suppressed nearly 65% CL-lum of active RA patients' neutrophils. Quercetin inhibited CL-luc the most effectively (IC50=1.71±0.36 μM). The four flavonols diminished myeloperoxidase activity, but they did not decrease NADPH oxidase activity, phagocytosis, microbial killing, or cell viability of neutrophils. The ability of the flavonols to scavenge hypochlorous acid and chloramines, but not H2O2, depended on the hydroxylation degree of the flavonol B-ring. Therefore, at physiologically relevant concentrations, the flavonols partially inhibited the oxidative metabolism of IC-stimulated neutrophils without affecting the other investigated effector functions. Using these compounds to modulate IC-mediated neutrophil activation is a promising safe therapeutic strategy to control inflammation in active RA patients.

Topics: Adult; Anti-Inflammatory Agents; Antigen-Antibody Complex; Arthritis, Rheumatoid; Cell Degranulation; Cells, Cultured; Female; Flavonoids; Humans; Kaempferols; Middle Aged; Neutrophils; Oxidation-Reduction; Peroxidase; Quercetin; Reactive Oxygen Species; Structure-Activity Relationship

Severe acute respiratory syndrome (SARS) is an infectious disease with a strong potential for transmission upon close personal contact and is caused by the SARS-coronavirus (CoV). However, there are no natural or synthetic compounds currently available that can inhibit SARS-CoV. We examined the inhibitory effects of 64 purified natural compounds against the activity of SARS helicase, nsP13, and the hepatitis C virus (HCV) helicase, NS3h, by conducting fluorescence resonance energy transfer (FRET)-based double-strand (ds) DNA unwinding assay or by using a colorimetry-based ATP hydrolysis assay. While none of the compounds, examined in our study inhibited the DNA unwinding activity or ATPase activity of human HCV helicase protein, we found that myricetin and scutellarein potently inhibit the SARS-CoV helicase protein in vitro by affecting the ATPase activity, but not the unwinding activity, nsP13. In addition, we observed that myricetin and scutellarein did not exhibit cytotoxicity against normal breast epithelial MCF10A cells. Our study demonstrates for the first time that selected naturally-occurring flavonoids, including myricetin and scultellarein might serve as SARS-CoV chemical inhibitors.

Topics: Adenosine Triphosphate; Antiviral Agents; Apigenin; Breast; Cell Line; Cell Proliferation; Colorimetry; DNA; DNA Helicases; Epithelial Cells; Female; Flavonoids; Fluorescence Resonance Energy Transfer; Hepacivirus; Humans; Hydrolysis; Inhibitory Concentration 50; Kinetics; Methyltransferases; RNA Helicases; Severe acute respiratory syndrome-related coronavirus; Species Specificity; Viral Nonstructural Proteins; Viral Proteins

It has been suggested that the increasing glycation in diabetes can influence the ability of plasma proteins to bind to small molecules. Herein, the influence of flavonoids on the glycation of plasma proteins was investigated. After being incubated with glucose at 37 °C, the levels of glycated albumin (HGA) were significantly improved in healthy human plasma proteins (HPP). The inhibitory effects of flavonoids against the formation of advanced glycation products (AGEs) in HPP were determined as: galangin > apigenin > kaempferol ≈ luteolin > myricetin > quercetin. After being combined with 20 μmol L⁻¹ of quercetin for 11 days, the fresh plasma with δ-glucose caused 323.05-32.07% inhibition of HGA formation in type II diabetes plasma proteins (TPP). Luteolin showed weak inhibition of HGA formation in TPP. However, kaempferol, galangin and apigenin hardly inhibited the formation of HGA in TPP. These results showed that more hydroxyl groups on ring B of flavonoids will enhance the inhibitory effects on the HGA formation in TPP.

Topics: Apigenin; Blood Proteins; Diabetes Mellitus, Type 2; Flavonoids; Glucose; Glycation End Products, Advanced; Glycosylation; Humans; Kaempferols; Luteolin; Quercetin

The potential of three natural flavonols (galangin, kaempferol and myricetin) to protect against D-galactose-induced cognitive impairment in mice was investigated. After 8 weeks treatment, the mice were assessed by behavioural tests. The levels of oxidative stress, the amount of Na(+),K(+)-ATPase and extracellular signal-regulated kinases (ERK)-cyclic AMP response element binding protein (CREB) signaling pathway in hippocampus were also analysed. It was found that all the three dietary flavonols could ameliorate the oxidative stress, enhance the activity of Na(+),K(+)-ATPase and regulate the expression of ERK-CREB pathway in mice. However, only kaempferol and myricetin could significantly improve the learning and memory capability when compared with D-galactose model. Our results suggest that the presence of hydroxyl groups in the B ring of flavonols may have contribution to the neuroprotective activity.

Topics: Animals; Behavior, Animal; Cognition Disorders; Cyclic AMP Response Element-Binding Protein; Extracellular Signal-Regulated MAP Kinases; Flavonoids; Galactose; Hippocampus; Humans; Kaempferols; Male; Mice; Neuroprotective Agents; Oxidative Stress; Signal Transduction

Klebsiella pneumoniae is a ubiquitous opportunistic pathogen that colonizes at the mucosal surfaces in humans and causes severe diseases. Many clinical strains of K. pneumoniae are highly resistant to antibiotics. Here, we used fluorescence quenching to show that the flavonols galangin, myricetin, quercetin, and kaempferol, bearing different numbers of hydroxyl substituent on the aromatic rings, may inhibit dNTP binding of the primary replicative DnaB helicase of K. pneumoniae (KpDnaB), an essential component of the cellular replication machinery critical for bacterial survival. The binding affinity of KpDnaB to dNTPs varies in the following order: dCTP ~ dGTP > dTTP > dATP. Addition of 10 μM galangin significantly decreased the binding ability of KpDnaB to dATP, whereas the binding affinity of KpDnaB to dGTP that was almost unaffected. Our analyses suggest that these flavonol compounds may be used in the development of new antibiotics that target K. pneumoniae and other bacteria.

Topics: Anti-Bacterial Agents; DnaB Helicases; Flavonoids; Kaempferols; Klebsiella pneumoniae; Nucleotides; Protein Binding; Quercetin

The impact of Zn(2+) ion on interactions of flavonols galangin (Gal), kaempferol (Kae), quercetin (Que) and myricetin (Myr) with bovine serum albumin (BSA) in aqueous solution were studied by fluorescence quenching technique. The results exhibited that Zn(2+) ion affected significantly the interactions and the effect was distinct for the flavonol bearing different number of B-ring hydroxyl. Each flavonol can quench the fluorescence of BSA, displaying a quenching extent of Myr>Que>Kae>Gal, which is in good agreement with the number variation of the B-ring hydroxyl. The presence of Zn(2+) ion promoted the quenching for the flavonols, exhibiting an extent of Que>Myr>Kae>Gal. The values of K(a) for Kae, Que and Myr decreased whereas K(SV) and k(q) for Gal, Kae and Que increased with the number of B-ring hydroxyl. The type of BSA fluorescence quenching for Gal, Kae and Que hardly changed but the preference of static quenching increased. The values of K(SV) and k(q) for Myr remarkably decreased and the fluorescence quenching of BSA alternatively occurred via both static and dynamic type instead of only one (static or dynamic). The results suggest the key role of the B-ring hydroxyl and the distinct effect of its number in the interactions. Each flavonol may capture the BSA-bound Zn(II) in the solution, forming Zn(II)-flavonol complex that is possibly responsible for BSA fluorescence quenching. The B-ring hydroxyl could establish hydrogen bonds with BSA in the absence of Zn(2+) and act as donors for chelating in the presence of Zn(2+). The formation of dinuclear Zn(II)-Myr complex together with the hydrogen bonds between the free B-ring hydroxyl and BSA may contribute to the exceptional behavior of Myr.

Topics: Animals; Binding Sites; Binding, Competitive; Cattle; Flavonoids; Flavonols; Fluorescence; Hydrogen Bonding; Kaempferols; Kinetics; Molecular Structure; Protein Binding; Quercetin; Serum Albumin, Bovine; Spectrometry, Fluorescence; Zinc

Random Forest screening of the phytochemical constituents of 240 herbs used in traditional Chinese medicine identified a number of compounds as potential inhibitors of the human aromatase enzyme (CYP19). Molecular modelling/docking studies indicated that three of these compounds (myricetin, liquiritigenin and gossypetin) would be likely to form stable complexes with the enzyme. The results of the virtual screening studies were subsequently confirmed experimentally, by in vitro (fluorimetric) assay of the compounds' inhibitory activity. The IC-50s for the flavones, myricetin and gossypetin were determined as 10 and 11 microM, respectively, whilst the flavanone, liquiritigenin, gave an IC-50 of 0.34 microM--showing about a 10-fold increase in potency, therefore, over the first generation aromatase inhibitor, aminoglutethimide.

Topics: Algorithms; Aminoglutethimide; Aromatase Inhibitors; Drug Evaluation, Preclinical; Drugs, Chinese Herbal; Flavanones; Flavonoids; Fluorometry; Humans; Inhibitory Concentration 50; Models, Molecular; Structure-Activity Relationship

Tissue damage in autoimmune diseases involves excessive production of reactive oxygen species (ROS) triggered by immune complexes (IC) and neutrophil (PMN) interactions via receptors for the Fc portion of IgG (FcgammaR) and complement receptors (CR). Modulation of both the effector potential of these receptors and ROS generation may be relevant to the maintenance of body homeostasis. In the present study, the modulatory effect of four flavonols (myricetin, quercetin, kaempferol, galangin) on rabbit PMN oxidative metabolism, specifically stimulated via FcgammaR, CR or both classes of receptors, was evaluated by luminol- and lucigenin-dependent chemiluminescence assays. Results showed that flavonol inhibitory effect was not dependent on the cell membrane receptor class stimulated but related to the lipophilicity of the compounds (their apparent partition coefficient values were obtained by high-performance liquid chromatography), and was also inversely related to the number of hydroxyl groups in the flavonol B ring and the ROS-scavenger activity (assessed by the luminol--H2O2--horseradish peroxidase reaction). Under the experimental conditions the flavonols tested were not toxic to PMNs (evaluated by lactate dehydrogenase release and trypan blue exclusion) and did not interfere with IC-induced phagocytosis (evaluated by transmission electron microscopy). Our results suggested that inhibition of IC-stimulated PMNs effector functions by the flavonols tested herein was the result of cooperation of different cellular mechanisms.

Topics: Acridines; Animals; Antigen-Antibody Complex; Benzene Derivatives; Complement System Proteins; Flavonoids; Flavonols; Free Radical Scavengers; Hydrophobic and Hydrophilic Interactions; Hydroxylation; Immune Complex Diseases; Immunologic Factors; Kaempferols; Luminescent Measurements; Luminol; Molecular Structure; Neutrophils; Oxidation-Reduction; Phagocytosis; Quercetin; Rabbits; Receptors, Complement; Receptors, Fc; Structure-Activity Relationship

The antioxidant activity of flavonoids has been suggested to contribute to several health benefits associated with the consumption of fruits and vegetables. Four flavonols - myricetin (M), quercetin (Q), kaempferol (K) and galangin (G), all with different numbers of hydroxyl moieties (-OH) - were examined for their antioxidant activity and cytotoxicity on human umbilical vein endothelial cells (HUVECs) and for their potential antiangiogenic and cell adhesion effects. The relative antioxidant capacity of these flavonols in cell culture medium (cell-free system) and their intracellular antioxidant activity were M = Q > K = G, which correlated respectively with the presence of 3, 2, 1 and 0 moieties of -OH on their B-ring. The higher the numbers of -OH moieties on the B-ring the less toxic the flavonol was to HUVEC, and the LD50 was determined as: M (100 microM) > Q (50 microM) > K (20 microM) > G (10 microM). These flavonols at approximately 0.5 LD50 doses suppressed the vascular endothelial growth factor (VEGF)-stimulated HUVEC tubular structure formation by: M (47%) > Q (37%) > K (15%) > G (14%), which was not linearly associated with their numbers of -OH moieties. However, the magnitude of flavonols' suppression of activated U937 monocytic cells adhesion to HUVEC was associated with the number of -OH moieties on the B-ring. This was prominent when U937 cells were pretreated with these flavonols. In contrast, the numbers of -OH moiety had no apparent influence on the adhesion or expression of adhesion molecules when activated HUVECs were pretreated with these flavonols. The presence of different numbers of -OH moieties on the B-ring of the flavonols may contribute to their antioxidant activity as well as their toxicity and may play an important role in their potency for biological action such as angiogenesis and immune-endothelial cell adhesion, which, respectively, are important processes in the development of cancer and atherosclerosis.

Topics: Antioxidants; Cell Adhesion; Cell Adhesion Molecules; Cell Death; Cell Division; Cell Line; Cells, Cultured; Endothelial Cells; Flavonoids; Flavonols; Gene Expression; Humans; Kaempferols; Monocytes; Neovascularization, Physiologic; Quercetin; Structure-Activity Relationship; Tetradecanoylphorbol Acetate; Umbilical Veins; Vascular Endothelial Growth Factor A

Some flavonoids induce phase II enzymes both in vivo and in vitro. We have determined the structural requirements for this activity by examining the ability of naturally-occurring flavonoids to induce the phase II enzyme, quinone reductase (NAD(P)H:quinone oxidoreductase; EC 1.6.99.2), in murine Hepalclc7 cells. Hydroxylation of the B ring is not essential for induction, since galangin and kaempferol (with 0 and 1 hydroxyl in the B ring, respectively) are better inducers than quercetin (2 B ring hydroxyls). A 2,3 double bond in the C ring is essential for induction, since taxifolin, which has the same substitution pattern as quercetin but lacks the 2,3 double bond, is not an inducer. This is supported by catechin and epicatechin, which do not possess the 2,3 double bond and are also not inducers. A 3-hydroxyl group increases the activity but is not essential for induction, since apigenin is an inducer but kaempferol (which has the same structure as apigenin but possesses a 3-hydroxyl group) is more effective. The data show that, of the flavonoids, the flavonols are the most effective inducers of quinone reductase activity in Hepa1c1c7 cells (kaempferol approximately galangin > quercetin > myricetin approximately apigenin (a flavone)) and that flavanols and flavans are ineffective.

Topics: Animals; Catechin; Chamomile; Enzyme Induction; Enzyme Inhibitors; Flavonoids; Flavonols; Kaempferols; Liver Neoplasms, Experimental; Mice; NAD(P)H Dehydrogenase (Quinone); Oils, Volatile; Plants, Medicinal; Quercetin; Tumor Cells, Cultured