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Flavanone

About: Flavanone is a research topic. Over the lifetime, 1965 publications have been published within this topic receiving 54729 citations. The topic is also known as: flavanones.


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Journal ArticleDOI
TL;DR: Thirty-seven flavonoid compounds were investigated for their effect on feeding choice with bertha armyworm and flavone reduced both larval weight as well as larval and pupal development time in a no-choice bioassay.
Abstract: Thirty-seven flavonoid compounds (9 flavones, 18 flavonols, 8 flavanones, and 2 flavanonols) were investigated for their effect on feeding choice with bertha armyworm (Mamestra configurata Walker; BAW). Feeding choice was dependent upon subtle differences in biochemical structure. Unsubstituted flavone and flavanone were the strongest feeding deterrents in the choice bioassay, while 7,4′-dihydroxyflavone and dihydroquercetin stimulated BAW to feed. The constitutive flavonoids of Brassica napus, isorhamnetin-3-sophoroside-7-glucoside and kaempferol-3,7-diglucoside, were effective deterrents when supplemented at concentrations higher than endogenous levels. In a no-choice bioassay, flavone reduced both larval weight as well as larval and pupal development time.

67 citations

Journal ArticleDOI
TL;DR: It is reported here that self-cyclisation of naringenin chalcone is dramatically reduced at pH-values ⩽ 6.5 and in the presence of high concentrations of serum albumin.

67 citations

Journal ArticleDOI
TL;DR: In this paper, the authors investigated the impact of naringenin and hesperetin metabolites at 0·5, 2 and 10 μM on monocyte adhesion to TNF-α-activated human umbilical vein endothelial cells and on gene expression.
Abstract: Flavanones are found specifically and abundantly in citrus fruits. Their beneficial effect on vascular function is well documented. However, little is known about their cellular and molecular mechanisms of action in vascular cells. The goal of the present study was to identify the impact of flavanone metabolites on endothelial cells and decipher the underlying molecular mechanisms of action. We investigated the impact of naringenin and hesperetin metabolites at 0·5, 2 and 10 μM on monocyte adhesion to TNF-α-activated human umbilical vein endothelial cells (HUVEC) and on gene expression. Except hesperetin-7-glucuronide and naringenin-7-glucuronide (N7G), when present at 2 μM, flavanone metabolites (hesperetin-3'-sulphate, hesperetin-3'-glucuronide and naringenin-4'-glucuronide (N4'G)) significantly attenuated monocyte adhesion to TNF-α-activated HUVEC. Exposure of both monocytes and HUVEC to N4'G and N7G at 2 μM resulted in a higher inhibitory effect on monocyte adhesion. Gene expression analysis, using TaqMan Low-Density Array, revealed that flavanone metabolites modulated the expression of genes involved in atherogenesis, such as those involved in inflammation, cell adhesion and cytoskeletal organisation. In conclusion, physiologically relevant concentrations of flavanone metabolites reduce monocyte adhesion to TNF-α-stimulated endothelial cells by affecting the expression of related genes. This provides a potential explanation for the vasculoprotective effects of flavanones.

67 citations

Journal ArticleDOI
TL;DR: It could be shown that further mechanisms of flavonoid interaction with the overall mutagenic process may exist, such as interactions with biological membranes (luteolin, fisetin) and effects on fixation and expression ofDNA damage.
Abstract: The mutagenicity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in Salmonella typhimurium TA98 is inhibited by flavonoids with distinct structure-antimutagenicity relationships (Edenharder, R., I. von Petersdorff I. and R. Rauscher (1993). Antimutagenic effects of flavonoids, chalcones and structurally related compounds on the activity of 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) and other heterocyclic amine mutagens from cooked food, Mutation Res., 287, 261-274). With respect to the mechanism(s) of antimutagenicity, the following results were obtained here. (1) 7-Methoxy- and 7-ethoxyresorufin-O-dealkylase activities in rat liver microsomes, linked to cytochrome P-450-dependent 1A1 and 1A2 monooxygenases catalyzing oxidation of IQ to N-hydroxy-IQ (N-OH-IQ), were effectively inhibited by 16 flavonoids (IC50: 0.4-9.8 microM). Flavones and flavonols are in general more potent enzyme inhibitors than flavanones, isoflavones, and chalcones. Among flavones the presence of hydroxyl or methoxyl groups resulted in minor changes only. However, among flavonols and flavanones the parent compounds exerted the strongest inhibitory effects, which decreased in dependence on number and position of hydroxyl functions. Contrary to the results obtained in the Salmonella assay in the tests with alkoxyresorufins no extraordinary counteracting effects of isoflavones, of hydroxyl groups at carbons 6 or 2' or of the elimination of ring B (benzylideneacetone) were detected. (2) No effects of flavonoids on NADPH-dependent cytochrome P-450 reductase activity could be detected. (3) The effects of 30 flavonoids on mutagenicity induced by N-OH-IQ in S. typhimurium TA98NR were again structure dependent. The most striking feature was the, in principle, reverse structure-antimutagenicity pattern as compared to IQ: non-polar compounds were inactive and a 50% inhibition was achieved only by some flavones and flavonols (IC50: 15.0-148 nmol/ml top agar). Within the flavone and flavonol subgroups inhibitory effects increased in dependence on number and position of hydroxyl functions. Isoflavones and flavanones, however, as well as glycosides, were inactive. Hydroxyl groups at carbons 7, 3', 4', and 5' generated antimutagenic compounds, a hydroxyl function at C5 was ineffective, but hydroxyls at C3 and 6 as well as methoxyl groups at C3' (isorhamnetin) or 4' (diosmetin) generated comutagenic compounds. 4. Cytosolic activation of IQ to mutagenic metabolites as determined by experiments with the hepatic S105 fraction comprises about 10% of the mutagenicity after activation by the combined microsomal and cytosolic fractions (S9). The pattern of inhibition as produced by 20 flavonoids was closely similar to that observed with the S9 fraction. 5. In various experiments designed for modulation of the mutagenic response, it could be shown that further mechanisms of flavonoid interaction with the overall mutagenic process may exist, such as interactions with biological membranes (luteolin, fisetin) and effects on fixation and expression of.DNA damage (flavone, fisetin).

67 citations

Journal ArticleDOI
TL;DR: First total synthesis of flavocommelin, a component of the blue supramolecular pigment, commelinin, from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 angstroms in CH2Cl2 and a catalytic amount of BF3 x Et2O.
Abstract: We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 angstroms in CH2Cl2 and a catalytic amount of BF3 x Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4'-O-glycosylation, promoted with a combination of BF3 x Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.

67 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202355
2022145
202165
202049
201944
201848