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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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TL;DR: The protein binding rates of structurally different flavonoids to human serum albumin (HSA) were elucidated by applying the high performance affinity chromatography (HPAC) and it was found that an additional methoxy group in flavone ring A would decrease the protein binding rate.
55 citations
TL;DR: Phylogenetic analyses of the subfamily of plant CYP93B enzymes indicate the evolution of a gene encoding a flavone synthase which originally catalyzed the direct conversion of flavanones into flavones, via early gene duplication into a less efficient enzyme with an altered catalytic mechanism.
55 citations
TL;DR: The inhibitory activity of naringenin was found to be comparable to that of azelastine, which is a commercially available antiallergic drug, and suggests that the flavanone glycosides can be activated by intestinal bacteria, and may be effective toward IgE-induced atopic allergies.
Abstract: This study examined the passive cutaneous anaphylaxis-inhibitory activity of the flavanones isolated from the pericarp of Citrus unshiu (Family Rutaceae) and the fruit of Poncirus trifoliata (Family Rutaceae). Naringenin, hesperetin and ponciretin potently inhibited IgE-induced beta-hexosaminidase release from RBL-2H3 cells and the PCA reaction. Among the flavanones examined, naringenin was the most potent with an IC50 value for beta-hexosaminidase release from RBL-2H3 cells of 0.029 mM. Intraperitoneally administered naringenin (5 mg/kg) inhibited PCA by 70 +/- 1.7 %, compared with the control group. The inhibitory activity of naringenin was found to be comparable to that of azelastine, which is a commercially available antiallergic drug. However, their glycosides, hesperidin, naringin and poncirin, did not inhibit the in vitro release of beta-hexosaminidase from the RBL-2H3 cells. On the other hand, these flavanones did not improve the oxazolone-induced dermatitis in the mouse ears. When the flavanone glycosides were administered to rats, the aglycones, but not the flavanone glycosides, were excreted in urine. This suggests that the flavanone glycosides can be activated by intestinal bacteria, and may be effective toward IgE-induced atopic allergies.
55 citations
TL;DR: Results demonstrated that PGE2 is an important mediator in TPA‐induced proliferation, and MAPK phosphorylation was located at the upstream of COX‐2, c‐Jun, and ODC gene expressions in Tpa‐induced responses.
Abstract: Biological functions of flavanones have been studied extensively, however, the structure-related activities of flavanones on 12-o-tetradecanoylphorbol 13-acetate (TPA)-induced promotive effects are still unclear. In this study, flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone showed the most significant dose-dependent inhibition on TPA-induced proliferative effects among eight tested flavanones in NIH3T3 cells. TPA-induced mitogen activated protein kinases (MAPK) phosphorylation, ornithine decarboxylase (ODC), c-Jun, and cyclooxygenase 2 (COX-2) protein expressions in a time-dependent manner, and the maximal inductive time point is at 1 h for MAPK phosphorylation and 6 h for others. Flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone showed the dose-dependent inhibition on TPA-stimulated MAPK phosphorylation, COX-2, ODC, c-Jun protein expressions. Induction of, prostaglandin E(2) (PGE(2)) production was detected in TPA-treated NIH3T3 cells, and flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone inhibited significantly PGE(2) production induced by TPA. Addition of PGE(2) reverses the inhibitory activities of flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone on TPA-induced proliferation. And, PD98059, a specific inhibitor of ERKs, inhibited TPA-induced MAPK phosphorylation, accompanied by decreasing COX-2, c-Jun, and ODC protein expression, and showed dose-dependent inhibition on TPA-induced proliferation in cells. These results demonstrated that PGE(2) is an important mediator in TPA-induced proliferation, and MAPK phosphorylation was located at the upstream of COX-2, c-Jun, and ODC gene expressions in TPA-induced responses. Furthermore, flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone (100 microM) suppressed TPA-induced colony formation associated with blocking MAPK phosphorylation, ODC, c-Jun, and COX-2 proteins expression. And, 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay showed that flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone did not perform potent anti-radical activities among these eight tested compounds. In conclusion, this study provided molecular evidences to demonstrate that flavanone, 2'-OH flavanone, 4'-OH flavanone, 6-OH flavanone were potent inhibitors on TPA-induced responses without notable cytotoxicity through suppression of PGE(2) production; and anti-radical activity of flavanones was not correlated with preventing the occurrence of tumor promotion. We proposed that blocking TPA-induced intracellular signaling responses might be involved in the anti-promotive mechanism of flavanones.
54 citations
TL;DR: A phenyl propanoid glycoside, cinnamoyl-β-d-glucopyranoside (CIN), characteristic of blood oranges, was isolated by column and thin layer chromatographies as discussed by the authors.
Abstract: A phenyl propanoid glycoside, cinnamoyl-β-d-glucopyranoside (CIN), characteristic of blood oranges, was isolated by column and thin layer chromatographies The structure of this compound was established using 1H and 13C NMR spectral data and by analysis of its components upon hydrolysis Flavanone glycosides (FGs) [narirutin (NAT), hesperidin (HES), and didymin (DID)] and cinnamic derivatives [CIN and trans-cinnamic acid (TCA)] of four blood orange varieties (47 samples) were analyzed by HPLC Differences in the polyphenol profiles clearly showed variety differentiation Keywords: Fruit juice; Citrus sinensis; blood orange varieties; cinnamoyl-β-d-glucopyranoside; flavanone glycoside; NMR; liquid chromatography
54 citations