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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
24 Mar 2021
TL;DR: In this paper, the authors applied the density functional theory (DFT) to investigate the properties of seven flavonoid structures with well-reported antioxidant activity: flavan, anthocyanidin, flavanone, isoflavone, flavone, and flavan-3-ol.
Abstract: Understanding the antioxidant activity of flavonoids is important to investigate their biological activities as well as to design novel molecules with low toxicity and high activity. Aromaticity is a chemical property found in cyclic structures that plays an important role in their stability and reactivity, and its investigation can help us to understand the antioxidant activity of some heterocyclic compounds. In the present study, we applied the density functional theory (DFT) to investigate the properties of seven flavonoid structures with well-reported antioxidant activity: flavan, anthocyanidin, flavanone, flavonol, isoflavone, flavone, and flavan-3-ol. Conformational, structural, magnetic, and electronic analyses were performed using nuclear magnetic resonance, ionization potentials, electron affinity, bond dissociation energy, proton affinity, frontier molecular orbitals (highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO)), and aromaticity through nucleus-independent chemical shifts to analyze these seven flavonoid structures. We revised the influence of hydroxyl groups on the properties of flavonoids and also investigated the influence of the aromaticity of these seven flavonoids on the antioxidant activity.

31 citations

Journal ArticleDOI
TL;DR: A new flavanone, named euchrestalfavanone A (I), mp 145-147°C, C25H28O5, was isolated from the root of Euchresta japonica HOOK as mentioned in this paper.
Abstract: A new flavanone, named euchrestalfavanone A (I), mp 145-147°C, C25H28O5, was isolated from the root of Euchresta japonica HOOK. f. ex REGEL (Leguminosae) together with l-maackiain, medicagol and trifolirhizin. The structure of I was established to be 6, 3'-di-γ, γ-dimethylallyl-5, 7, 4'-trihydroxyflavanone on the basis of chemical and spectral evidence.

31 citations

Journal ArticleDOI
TL;DR: It is suggested that flavanone derivatives control the expression of cell cycle regulatory proteins, which blocks G1 cell cycle progression and inhibits the clonogenicity of HCT116 cells.
Abstract: Naringenin has been shown to display various biological effects such as antioxidant, anticancer, anti-inflammatory, and antiviral activities. Taxifolin inhibits the production of lipopolysaccharide-induced prostaglandin E, and fustin suppresses the activity of acetylcholinesterase. They all belong to flavanone which is a class of flavonoids with a C6-C3-C6 skeleton. Since the anticancer activities of flavanone derivatives have rarely been reported, we examined the effects of 26 flavanone derivatives on HCT116 colorectal cancer cells. Our results suggest that flavanone derivatives control the expression of cell cycle regulatory proteins, which blocks G1 cell cycle progression and inhibits the clonogenicity of HCT116 cells. In addition, in order to design flavanone derivatives that show better anticancer activity, structure-activity relationships were examined.

31 citations

Journal ArticleDOI
TL;DR: The hydrolytic activity of the recombinant β-glucosidase from Pyrococcus furiosus for the flavanone glycoside hesperidin was optimal at pH 5.5 and 95 °C and the conversion yields, concentrations, and productivities in this study are the highest among those obtained from citrus extracts.
Abstract: The hydrolytic activity of the recombinant β-glucosidase from Pyrococcus furiosus for the flavanone glycoside hesperidin was optimal at pH 5.5 and 95 °C in the presence of 0.5% (v/v) dimethyl sulfoxide (DMSO) and 0.1% (w/v) Tween 40 with a half-life of 88 h, a Km of 1.6 mM, and a kcat of 68.4 1/s. The specific activity of the enzyme for flavonoid glycosides followed the order hesperidin > neohesperidin > naringin > narirutin > poncirin > diosmin > neoponcirin > rutin. The specific activity for flavanone was higher than that for flavone or flavonol. DMSO at 10% (v/v) was used to increase the solubility of flavanone glycosides as substrates. The enzyme completely converted flavanone glycosides (1 g/L) to flavanone aglycones and disaccharides via one-step reaction. The major flavanone in grapefruit peel, grapefruit pulp, or orange peel extract was naringin (47.5 mg/g), naringin (16.6 mg/g), or hesperidin (18.2 mg/g), respectively. β-Glucosidase from P. furiosus completely converted naringin and narirutin in 100% (w/v) grapefruit peel extract to 22.5 g/L naringenin after 12 h, with a productivity of 1.88 g L(-1) h(-1); naringin and narirutin in 100% (w/v) grapefruit pulp extract to 8.1 g/L naringenin after 9 h, with a productivity of 0.90 g L(-1) h(-1); and hesperidin in 100% (w/v) orange peel extract to 9.0 g/L hesperetin after 9 h, with a productivity of 1.00 g L(-1) h(-1). The conversion yields, concentrations, and productivities of flavanone aglycones in this study are the highest among those obtained from citrus extracts. Thus, this enzyme may be useful for the industrial hydrolysis of flavanone glycosides in citrus extracts.

31 citations

Journal ArticleDOI
01 Sep 1995
TL;DR: Three new flavonoids were isolated and identified from the roots of Tephrosia emoroides and showed strong feeding deterrent activity against C. partellus larvae with a mean percentage deterrence of 66.1% at a dose of 100 μg/disc.
Abstract: Three new and two previously known flavonoids were isolated and identified from the roots o/Tephrosia emoroides A Rich The new flavonoids included the flavanone 4″,5″-dihydro-5-methoxy-5″-isopropenylfurano-[2″,3″:7,8]-flavanone, the flavone 7-hydroxy-5-methoxy-8-(3″-hydroxy)-isopent-1-eneflavone and the pterocarpan 4′, S'-dihydro-5′-isopropenyl-8, 9-methylenedioxyfurano-[2′,3′:2,3]-pterocarpan The three new compounds were named emoroidenone, emoroidone, and emoroidocarpan, respectively The previously known flavonoids that were isolated were the flavanone, 5-methoxyisolonchocarpin and the flavene, hildegardtene The flavonoids were tested for antifeedant activity against the larvae of Chilo partellus Swinhoe using the maize leaf disc bioassay The flavanone emoroidenone showed strong feeding deterrent activity against C partellus larvae with a mean percentage deterrence of 661% at a dose of 100 μg/disc The other flavonoids showed little or no feeding deterrent activity against C partellus l

31 citations


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