Topic
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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TL;DR: The flavone propargyl ether derivatives were found to be more potent inhibitors of P450s 1A1 and 1A2, and the parent hydroxy flavones were tested for both direct inhibition and mechanism-based inhibition of cytochrome P450 enzymes.
Abstract: Naturally occurring flavonoids are known to be metabolized by several cytochrome P450 enzymes including P450s 1A1, 1A2, 1B1, 2C9, 3A4, and 3A5. In general flavonoids can act as substrates, inducers, and/or inhibitors of P450 enzymes. The position of the substituents on the flavone backbone has been shown to impact the biological activity against P450 enzymes. To explore the effect of a propargyl ether substitution on flavones and flavanones, 2´-flavone propargyl ether (2´-PF), 3´-flavone propargyl ether (3´-PF), 4´-flavone propargyl ether (4´-PF), 5-flavone propargyl ether (5-PF), 6-flavone propargyl ether (6-PF), 7-flavone propargyl ether (7-PF), 6-flavanone propargyl ether (6-PFN), and 7- flavanone propargyl ether (7-PFN) were synthesized. All of the newly synthesized compounds and the parent hydroxy flavones were tested for both direct inhibition and mechanism-based inhibition of cytochrome P450 enzymes 1A1, 1A2, 2A6, and 2B1. The flavone propargyl ether derivatives were found to be more potent inhibitors of P450s 1A1 and 1A2. None of the flavones and flavanones in our study showed any inhibition of P450 2A6. Only 2´-PF and 6-PFN inhibited P450 2B1. 3´-PF showed direct inhibition of P450 1A1 with the highest observed potency of 0.02 µM, in addition to its ability to cause mechanism-based inhibition with KI and kinactivation values of 0.24 µM and 0.09 min-1 for this enzyme. 7- Hydroxy flavone also exhibited mechanism-based inhibition of P450 1A1 with KI and kinactivation values of 2.43 µM and 0.115 min-1. Docking studies and QSAR studies on P450 enzymes 1A1 and 1A2 were performed which revealed important insights into the nature of binding of these molecules and provided us with good QSAR models that can be used to design new flavone derivatives.
20 citations
TL;DR: Two new flavonoids, (2S)-4′,5-dihydroxyl-6,7-di-O-β-D-glucopyranosyl flavanone (1) and 6-hydroxykaempferol 6,7 -di- O- β-Dglucophosphoruside (2), were isolated from Carthamus tinctorius and elucidated by spectroscopic means including 2D NMR, ESIMS and CD as mentioned in this paper.
Abstract: Two new flavonoids, (2S)-4′,5-dihydroxyl-6,7-di-O-β-D-glucopyranosyl flavanone (1) and 6-hydroxykaempferol 6,7-di-O-β-D-glucopyranoside (2), were isolated from Carthamus tinctorius. Their structures were elucidated by spectroscopic means including 2D NMR, ESIMS and CD.
20 citations
TL;DR: The HPLC application to Citrus species used as crude drugs in Japan showed that the relative ratios of naringin to the C-2 epimer were 75-93% in Kijitsu, 74-79% in Kikoku and 54-64% in Tohi, which suggested that the averages of relative ratio of (2S)-naringin incitrus species reduced according to the maturity of fruits.
20 citations
TL;DR: The isolation and antimicrobial activity of presence of Flemingiaflavanone is being reported for the first time.
Abstract: Purpose: To carry out a bioactivity guided fractionation and isolation of the antimicrobial constituent(s) of the roots of Flemingia strobilifera against some bacteria and fungi. Methods: The root of F. strobilifera was extracted with methanol, butanol and dichloromethane. Antimicrobial activity of the extracts was determined against both bacteria and fungi while the isolation and characterization of compounds of the extracts was done by column chromatography,2D spectroscopic studies and spectral data (U.V, I.R, NMR and MS). Results: Flemingiaflavanone (8, 3 ' -diprenyl-5, 7, 4 ' -trihydroxy flavanone), Genistin (5, 4 ' dihydroxy isoflavone 7-O-glucoside) and β - sitosterol-D glucoside were isolated from the extracts. Flemingiaflavanone showed significant antimicrobial activity against Gram-positive (S. aureus, S. epidermidis, MRSA), Gram-negative bacteria (Ps. aeruginosa, E. coli) and fungi (C. albicans). Genistin showed moderate activity against Gram-positive, Gram-negative bacteria and fungi. Conclusions: The isolation and antimicrobial activity of presence of Flemingiaflavanone is being reported for the first time.
20 citations
TL;DR: In this paper, the methanolic extract of the wood of Vernonia diffusa has been extracted and two flavanones were identified: hesperidin and a new flavanone, 3'-methylhesperetin (homoespeetin) and sucrose, which was identified as its acetyl derivative.
Abstract: From the methanolic extract of the wood of Vernonia diffusa two flavanones were isolated and identified: hesperidin and a new flavanone, 3'-methylhesperetin (homoesperetin) and sucrose, which was identified as its acetyl derivative. The homoesperetin was identified as the aglicone obtained in the hydrolysis of the new natural flavanone glycoside, homoesperetin-7-O-rutinoside. From the dichloromethane extract, a mixture of sitosterol and stigmasterol was isolated together with a mixture of aliphatic acids. The new octaacetylhesperidin derivative was also prepared. Structural determination was made by 1H and 13C-NMR spectrometric data including DEPT, 1Hx1H-COSY, and 1Hx13C-COSY and NOEDIFF techniques.
20 citations