Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “FLAVONES”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 127 records · Page 7Linked to original sources
PubMed2003

Determination of flavones in Crataegus pinnatifida by capillary zone electrophoresis.

A capillary electrophoretic method for the separation of four flavones in Crataegus pinnatifida is developed. The four flavones in Crataegus pinnatifida are separated on baseline within 15 min using 50mM borax buffer containing 15% acetonitrile and adjusted to pH 8.15 with phosphoric acid. The detection limits of vitexin-2"-rhamnoside, hyperside, rutin, and vitexin are 0.35, 0.30, 0.40 and, 0.29 microg/mL, respectively. The recovery of these flavones is as follows: vitexn-2"-rhamnoside 96.8%, hyperside 99.9%, rutin 97.1%, and vitexin 97.8%. The results are in accordance with those obtained in the high-performance liquid chromatography system. The content of flavones is higher in Crataegus pinnatifida leaves than in its fruits, and hyperside is not detected in either Crataegus pinnatifida fruits or flowers.

Buffers↗
PubMed2001

Differential expression of two cytochrome P450s involved in the biosynthesis of flavones and anthocyanins in chemo-varietal forms of Perilla frutescens.

In Perilla frutescens, there are two varietal forms of anthocyanin accumulation, i.e. red and green forms. The cDNA clones encoding flavone synthase II (FSII) and flavonoid 3'-hydroxylase (F3'H), two cytochrome P450s that are involved in the biosynthesis of flavones and anthocyanins, were isolated from P. frutescens. The FSII cDNA encoded a 57.1 kDa protein designated as CYP93B6, and the F3'H cDNA encoded 57.5 kDa protein designated as CYP75B4. Recombinant CYP93B6 expressed in yeast converted flavanones to flavones with K(m) values of 8.8-11.9 microM. Recombinant CYP75B4 catalyzed 3'-hydroxylation of flavanones to the corresponding compounds with K(m) values of 18-20 microM. The CYP93B6 transcript accumulated to an equal level in leaves of both red and green forms of P. frutescens, in agreement with the accumulation pattern of flavones in the leaves. However, the CYP75B4 transcript was predominantly expressed in the red form of P. frutescens, and its expression was induced by light in conjunction with other transcripts of biosynthetic enzymes of anthocyanin. These results indicate that gene expression of a set of anthocyanin biosynthetic enzymes including F3'H is regulated coordinately only in the red form of P. frutescens but not in the green form, whilst FSII gene expression is controlled in a similar manner in red and green forms of P. frutescens.

Anthocyanins↗
PubMed2001

Intake of flavonols and flavones and risk of coronary heart disease in male smokers.

Flavonols and flavones are antioxidant polyphenolic compounds found in tea, vegetables, fruits, and wine. In experimental studies they have been effective free radical scavengers, metal chelators, and antithrombotic agents. In the few epidemiologic studies of these agents, some have suggested an inverse association between intake of flavonols and flavones and the risk of cardiovascular disease. Our study population comprised 25,372 male smokers, 50-69 years of age, with no previous myocardial infarction. They were participants of the Alpha-Tocopherol, Beta-Carotene Cancer Prevention Study, which was a randomized, double-blind, placebo-controlled trial with daily supplementation of alpha-tocopherol (50 mg per day) and/or beta-carotene (20 mg per day). The men completed a validated dietary questionnaire at baseline. After 6.1 years of follow-up, there were 1,122 nonfatal myocardial infarctions and 815 coronary deaths. In the multivariate model, the relative risk of nonfatal myocardial infarction was 0.77 (95% confidence interval = 0.64-0.93) among men in the highest (median 18 mg per day) compared with the lowest (median 4 mg per day) quintile of flavonol and flavone intake. The respective relative risk for coronary death was 0.89 (95% confidence interval = 0.71-1.11). Thus, intake of flavonols and flavones was inversely associated with nonfatal myocardial infarction, whereas there was a weaker association with coronary death.

Aged↗
PubMed2000

Relaxation to flavones and flavonols in rat isolated thoracic aorta: mechanism of action and structure-activity relationships.

The mechanism of the relaxant action and the structure-activity relation of flavonols (fisetin, quercetin, and 3,3',4'-trihydroxyflavone) and flavones (apigenin, chrysin, and luteolin) were examined in rat isolated thoracic aorta. The control responses to flavonols and flavones were compared with responses observed after the removal of the endothelium or in the presence of the L-type Ca2+ channel blocker, nifedipine (10(-7) M). The effects of flavonoids on contraction caused by the influx of extracellular Ca2+ and agonist-induced release of intracellular Ca2+ also were investigated. The flavones exhibited endothelium-independent vasorelaxation, whereas the removal of the endothelium significantly decreased the sensitivity of the relaxant responses to the flavonols without affecting the maximal relaxation. In the presence of nifedipine, the responses to apigenin, luteolin, and quercetin were significantly inhibited, but relaxation to chrysin, fisetin, and 3,3',4'-trihydroxyflavone was unaffected. All flavonols and flavones caused concentration-dependent inhibition of the contractile responses to exogenous application of Ca2+ and the release of intracellular Ca2+ stimulated by phenylephrine. Of the six flavonoids examined, 3,3',4'-trihydroxyflavone was the most potent when causing vasorelaxation or inhibition of contraction caused by the influx or release of Ca2+. In conclusion, these studies provide evidence that the hydroxyl substitution in the carbon 3 position that characterizes the flavonols is important in stimulating endothelium-dependent vasorelaxation, and the absence of hydroxyl substitution on the A phenolic ring enhances the relaxant action.

Animals↗
PubMed2002

Flavone glucoside uptake into barley mesophyll and Arabidopsis cell culture vacuoles. Energization occurs by H(+)-antiport and ATP-binding cassette-type mechanisms.

In many cases, secondary plant products accumulate in the large central vacuole of plant cells. However, the mechanisms involved in the transport of secondary compounds are only poorly understood. Here, we demonstrate that the transport mechanisms for the major barley (Hordeum vulgare) flavonoid saponarin (apigenin 6-C-glucosyl-7-O-glucoside) are different in various plant species: Uptake into barley vacuoles occurs via a proton antiport and is competitively inhibited by isovitexin (apigenin 6-C-glucoside), suggesting that both flavone glucosides are recognized by the same transporter. In contrast, the transport into vacuoles from Arabidopsis, which does not synthesize flavone glucosides, displays typical characteristics of ATP-binding cassette transporters. Transport of saponarin into vacuoles of both the species is saturable with a K(m) of 50 to 100 microM. Furthermore, the uptake of saponarin into vacuoles from a barley mutant exhibiting a strongly reduced flavone glucoside biosynthesis is drastically decreased when compared with the parent variety. Thus, the barley vacuolar flavone glucoside/H(+) antiporter could be modulated by the availability of the substrate. We propose that different vacuolar transporters may be responsible for the sequestration of species-specific/endogenous and nonspecific/xenobiotic secondary compounds in planta.

ATP-Binding Cassette Transporters↗
PubMed1984

Inhibition of human estrogen synthetase (aromatase) by flavones.

Several naturally occurring and synthetic flavones were found to inhibit the aromatization of androstenedione and testosterone to estrogens catalyzed by human placental and ovarian microsomes. These flavones include (in order of decreasing potency) 7,8-benzoflavone, chrysin, apigenin, flavone, flavanone, and quercetin; 5,6-benzoflavone was not inhibitory. 7,8-Benzoflavone and chrysin were potent competitive inhibitors and induced spectral changes in the aromatase cytochrome P-450 indicative of substrate displacement. Flavones may thus compete with steroids in their interaction with certain monooxygenases and thereby alter steroid hormone metabolism.

Androstenedione↗
PubMed2001

Chronic obstructive pulmonary disease and intake of catechins, flavonols, and flavones: the MORGEN Study.

Flavonoids have been suggested to protect against chronic lung disease. We studied intake of catechins, flavonols, and flavones in relation to pulmonary function and COPD symptoms in 13,651 adults from three Dutch cities examined from 1994 to 1997. Dietary intake was estimated using a food frequency questionnaire, and flavonoid intake was calculated using specific food composition tables. Pulmonary function (FEV1) was determined by spirometry and COPD symptoms by questionnaire. Associations were presented for the fifth versus the first quintile of intake (Q5-Q1), adjusted for age, height (for FEV1 only), sex, smoking, BMI, and energy intake. Smoking was strongly associated with COPD, independent of dietary effects. Average catechin, flavonol, and flavone intake was 58 mg/d (SD = 46) with tea and apples as main sources. Total catechin, flavonol, and flavone intake was positively associated with FEV1 (beta(Q5-Q1) = 44 ml, 95% CI = 18-69) and inversely associated with chronic cough (OR(Q5-Q1) = 0.80, 95% CI = 0.66-0.97) and breathlessness (OR(Q5-Q1) = 0.74, 95% CI = 0.58- 0.94), but not chronic phlegm. Catechin intake was independently associated with FEV1 (beta(Q5-Q1) = 130 ml, 95% CI = 101-159) and all three COPD symptoms (OR(Q5-Q1) = 0.60-0.72, p < 0.001). Flavonol and flavone intake was independently associated with chronic cough only. Solid fruit, but not tea, intake was beneficially associated with COPD. Our results suggest a beneficial effect of a high intake of catechins and solid fruits against COPD.

Adult↗
PubMed1998

Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study.

Flavone and isoflavone phytoestrogens are plant chemicals and are known to be competitive inhibitors of cytochrome P450 aromatase with respect to the androgen substrate. Aromatase is the enzyme that converts androgen to estrogen; therefore, these plant chemicals are thought to be capable of modifying the estrogen level in women. In this study, the inhibition profiles of four flavones [chrysin (5, 7-dihydroxyflavone), 7,8-dihydroxyflavone, baicalein (5,6,7-trihydroxyflavone), and galangin (3,5,7-trihydroxyflavone)], two isoflavones [genistein (4,5,7-trihydroxyisoflavone) and biochanin A (5,7-dihydroxy-4-methoxyisoflavone)], one flavanone [naringenin (4, 5,7-trihydroxyflavanone)], and one naphthoflavone (alpha-naphthoflavone) on the wild-type and six human aromatase mutants (I133Y, P308F, D309A, T310S, I395F, and I474Y) were determined. In combination with computer modeling, the binding characteristics and the structure requirement for flavone and isoflavone phytoestrogens to inhibit human aromatase were obtained. These compounds were found to bind to the active site of aromatase in an orientation in which rings A and C mimic rings D and C of the androgen substrate, respectively. This study also provides a molecular basis as to why isoflavones are significantly poorer inhibitors of aromatase than flavones.

Animals↗
PubMed1980

Stimulation of mammalian epoxide hydrase activity by flavones.

1. A series of flavones have been examined for the ability to stimulate the activity in vitro of rat liver microsomal epoxide hydrase. Flavone and 7,8-benzoflavone both stimulate epoxide hydrase activity in vitro with styrene oxide as the substrate. The stimulation by flavone itself was several times that of 7,8-benzoflavone. 2. When tested in vitro under the same conditions, the stimulation by 7,8-benzoflavone was significantly greater than the stimulation by metyrapone, a recognized stimulator of the activity of epoxide hydrase in vitro. The stimulation by 6,7-benzoflavone was barely detectable; the 5,6-benzoflavone isomer did not stimulate epoxide hydrase activity. 3. Exposure of rate to either 7,8- or 5,6-benzoflavone for 4 days before killing did not increase the epoxide hydrase specific activity in the subsequently isolated microsomes. Exposure to flavone, however, did induce epoxide hydrase activity. 4. The possible relevance of these observations to the effects of benzoflavone upon arylhydrocarbon-induced tumours is discussed.

Animals↗
PubMed1988

Flavones in citrus exhibit antiadhesive action on platelets.

Two methoxylated flavones isolated from citrus, sinensetin (5 methoxyls) and heptamethoxy flavone (7 methoxyls), were compared in vitro with nobiletin for antiadhesive activity on rat platelets. Nobiletin (a hexamethoxyflavone also isolated from citrus) has been previously shown by several workers to have antiadhesive and antithrombogenic activity. The penta- and heptamethoxylated flavones exhibited anti-adhesive activity similar to that of nobiletin. However, activity did not parallel number of methoxyl groups which appear to indicate some degree of specificity between flavone structure and antiadhesive activity on platelets.

Animals↗
PubMed1998

In vitro and in vivo study of the clastogenicity of the flavone cirsitakaoside extracted from Scoparia dulcis L. (Scrophulariaceae).

The mutagenic effect of the flavone cirsitakaoside extracted from the medicinal herb Scoparia dulcis was evaluated in vitro by using human peripheral blood cultures treated with doses of 5, 10, and 15 microg of the flavone/ml culture medium for 48 h. The compound proved to be mutagenic at the highest concentration tested (15 microg/ml). Furthermore, the proliferative index was significantly reduced in all cultures treated with the flavone, although the mitotic index was not reduced. However, the clastogenic activity of the flavone cirsitakaoside was not observed when Swiss mice were treated orally with doses of 10, 20, and 30 mg/animal for 24 h.

Adult↗
PubMed2005

Synthesis, and cytotoxic and antiplatelet activities of oxime- and methyloxime-containing flavone, isoflavone, and xanthone derivatives.

A series of oxime- and methyloxime-containing flavone, isoflavone, and xanthone derivatives (1-12) were synthesized (Scheme) and evaluated for their cytotoxic (Table 1) and antiplatelet activities (Table 2). The in vitro anticancer assay indicated that the cytotoxicity of structurally related compounds decreases in the order isoflavones (7a-7c) > flavones (8a-8c) > xanthones (9a-9c), electron-releasing substituents (R) on the Ph ring being favorable (mean GI50 values of 2.84, 12.3, and 20.9 microM for 7c, 8c, and 9c, resp.). The inhibition of platelet aggregation induced by arachidonic acid (AA) similarly decreased from the isoflavone 1 (IC50 = 2.97 microM) to the flavone 2 (7.70 microM) to the xanthone 3 (inactive). Thereby, compound 1 seems to be a promising lead, since it was not only the most-potent aggregation inhibitor (IC50 = 2.97 microM), but was also found to be noncytotoxic at a concentration of 100 microM.

Antineoplastic Agents↗
PubMed2004

Antioxidant properties of flavone-6(4')-carboxaldehyde oxime ether derivatives.

The in vitro antioxidant properties of some flavone-6(4)-carboxaldehyde oxime ether derivatives (Ia-f, IIa-f) were determined by their effects on the rat liver microsomal NADPH-dependent lipid peroxidation (LP) levels by measuring the formation of 2-thiobarbituric acid reactive substances. The free radical scavenging properties of the compounds were also examined in vitro by determining their capacity to scavenge superoxide anions and interact with the stable free radical 2, 2-diphenyl-1-picrylhydrazyl (DPPH). The most active compounds, IIb (Flavone-4'-carboxaldehyde-O-ethyl oxime) and Id (Flavone-6-carboxaldehyde-O-[2-(1-pyrolidino) ethyl] oxime), caused 98 and 79% inhibition of superoxide anion production and DPPH stable free radical at 10(-3) M, respectively.

Animals↗
PubMed2005

Combinatorial biosynthesis of flavones and flavonols in Escherichia coli.

(2S)-Flavanones (naringenin and pinocembrin) are key intermediates in the flavonoid biosynthetic pathway in plants. Recombinant Escherichia coli cells containing four genes for a phenylalanine ammonia-lyase, cinnamate/coumarate:CoA ligase, chalcone synthase, and chalcone isomerase, in addition to the acetyl-CoA carboxylase, have been established for efficient production of (2S)-naringenin from tyrosine and (2S)-pinocembrin from phenylalanine. Further introduction of the flavone synthase I gene from Petroselinum crispum under the control of the T7 promoter and the synthetic ribosome-binding sequence in pACYCDuet-1 caused the E. coli cells to produce flavones: apigenin (13 mg/l) from tyrosine and chrysin (9.4 mg/l) from phenylalanine. Introduction into the E. coli cells of the flavanone 3beta-hydroxylase and flavonol synthase genes from the plant Citrus species led to production of flavonols: kaempferol (15.1 mg/l) from tyrosine and galangin (1.1 mg/l) from phenylalanine. The combinatorial biosynthesis of the flavones and flavonols in E. coli is promising for the construction of a library of various flavonoid compounds and un-natural flavonoids in bacteria.

Citrus↗
PubMed2005

Synthesis, antiproliferative, and antiplatelet activities of oxime- and methyloxime-containing flavone and isoflavone derivatives.

Certain oxime- and methyloxime-containing flavone and isoflavone derivatives were synthesized and evaluated for their antiproliferative activity against three solid cancer cells, human cervical epithelioid carcinoma (HeLa), hepatocellular carcinoma (SKHep1), and oral squamous cell carcinoma (SAS), which are commonly seen in Asian countries, including Taiwan. Selective compounds were also evaluated in the full panel of 60 human tumor cell lines and their mean GI50 values were obtained. The preliminary assays indicated flavone-6-yl derivatives are the most cytotoxic while isoflavone-7-yl derivatives are the best antiplatelet agents. Among them, (E)-6-(2-methoxyiminopropoxy)-2-phenyl-4H-1-benzopyran-4-one (14), (Z)-6-(2-hydroxyimino-2-phenylethoxy)-2-phenyl-4H-1-benzopyran-4-one (18a), and (Z)-6-[2-hydroxyimino-2-(4-methoxyphenyl)ethoxy]-2-phenyl-4H-1-benzopyran-4-one (18c) are three of the best antiproliferative agents with GI50 values of 0.8, 0.7, and 0.8 microM, respectively, against the growth of SKHep1; 0.9, 0.8, and 1.0 microM, respectively, against the growth of HeLa cells. Compound 18c is not only the most cytotoxic with a mean GI50 value of 0.08 microM against the full panel of 60 human tumor cell lines but also the only flavone derivative that exhibited a GI50 value of less than 1 microM against the growth of SAS. Flow cytometric analyses revealed that growth inhibition by 18c was due to accumulation in G2/M phase arrest and followed by apoptosis.

Cell Line, Tumor↗
PubMed2026

Flavones in osteosarcoma: Molecular mechanisms, antitumor activity, and translational challenges.

Osteosarcoma remains the most common primary malignant bone tumor, and survival has improved little over recent decades because of metastasis and therapeutic resistance. Flavones exhibit diverse anti-osteosarcoma activities by suppressing proliferation, inducing apoptosis, ferroptosis and autophagy, inhibiting metastasis, and modulating oncogenic signaling pathways, including PI3K-Akt, Wnt-&#x3b2;-catenin, STAT3, MAPK, and NF-&#x3ba;B. This review summarizes the cell-line-specific molecular mechanisms of representative flavones, critically evaluates current experimental limitations, and discusses strategies to improve clinical translation through nanotechnology-based delivery and combination therapy. Although clinical evidence remains lacking, flavones represent promising adjunctive candidates for overcoming chemoresistance and improving osteosarcoma treatment.

apoptosis and metastasis↗
PubMed2004

Variation in synergistic activity by flavone and its related compounds on the increased susceptibility of various strains of methicillin-resistant Staphylococcus aureus to beta-lactam antibiotics.

We found that some flavonoids had a weak antibacterial effect on methicillin-resistant Staphylococcus aureus (MRSA), but that at sub-MIC concentrations they greatly increased the susceptibility of these strains to beta-lactam antibiotics. Flavone showed diverse synergistic effects on the susceptibility of MRSA to beta-lactam antibiotics. The variation of the synergistic effects of the flavones to increase the susceptibility of strains of MRSA to beta-lactam antibiotics coincided with their varying effects on growth-inhibition of these strains. Based on these findings, we have proposed a model for the mechanisms of high resistance of MRSA to beta-lactams and the massive reduction in the beta-lactams MIC caused by flavones.

Anti-Bacterial Agents↗