Showing papers on "Flavanone published in 2021"
TL;DR: A type IV CHI from citrus is identified which enhances the accumulation of citrus flavanones and flavones (CFLs) and reveals a new DREB‐RAV transcriptional complex regulating flavonoid production.
Abstract: Flavanones and flavones are excellent source of bioactive compounds but the molecular basis of their highly efficient production remains elusive. Chalcone isomerase (CHI) family proteins play essential roles in flavonoid biosynthesis but little are known about the transcription factors controlling their gene expression. Here, we identified a type IV CHI (designated as CitCHIL1) from citrus which enhances the accumulation of citrus flavanones and flavones (CFLs). CitCHIL1 participates in a CFL biosynthetic metabolon and assists the cyclization of naringenin chalcone to (2S)-naringenin, which leads to the efficient influx of substrates to chalcone synthase (CHS) and improves the catalytic efficiency of CHS. Overexpressing CitCHIL1 in Citrus and Arabidopsis significantly increased flavonoid content and RNA interference-induced silencing of CitCHIL1 in citrus led to a 43% reduction in CFL content. Three AP2/ERF transcription factors were identified as positive regulators of the CitCHIL1 expression. Of these, two dehydration-responsive element binding (DREB) proteins, CitERF32 and CitERF33, activated the transcription by directly binding to the CGCCGC motif in the promoter, while CitRAV1 (RAV: related to ABI3/VP1) formed a transcription complex with CitERF33 that strongly enhanced the activation efficiency and flavonoid accumulation. These results not only illustrate the specific function that CitCHIL1 executes in CFL biosynthesis but also reveal a new DREB-RAV transcriptional complex regulating flavonoid production.
64 citations
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
TL;DR: NP and its phenolic constituents exhibited in vitro free radical scavenging activity together with a promising antidiabetic effect against α-amylase and α-glucosidase enzymes, suggesting that NP could be a good candidate in nutraceuticals and food products.
18 citations
TL;DR: It is demonstrated that NGEN decreased neuronal apoptosis and improved antioxidant defense in MG-treated NSC34 cells, suggesting the potential benefits of NGEN on the prevention of MG-induced or diabetes/hyperglycemia-related neurotoxicity.
Abstract: Objectives: Recent studies revealed the neuroprotective effects of naringenin (NGEN), a common dietary bioflavonoid contained in citrus fruits. However, there are limited data on its protection aga...
16 citations
TL;DR: In this paper, the anti-MRSA properties of 23 prenylated (iso)flavonoids were assessed in-vitro using a QSAR model having a good fit (R2adj 0.61), low average prediction errors and a good predictive power (Q2LOO 0.57).
Abstract: High resistance towards traditional antibiotics has urged the development of new, natural therapeutics against methicillin-resistant Staphylococcus aureus (MRSA). Prenylated (iso)flavonoids, present mainly in the Fabaceae, can serve as promising candidates. Herein, the anti-MRSA properties of 23 prenylated (iso)flavonoids were assessed in-vitro. The di-prenylated (iso)flavonoids, glabrol (flavanone) and 6,8-diprenyl genistein (isoflavone), together with the mono-prenylated, 4′-O-methyl glabridin (isoflavan), were the most active anti-MRSA compounds (Minimum Inhibitory Concentrations (MIC) ≤ 10 µg/mL, 30 µM). The in-house activity data was complemented with literature data to yield an extended, curated dataset of 67 molecules for the development of robust in-silico prediction models. A QSAR model having a good fit (R2adj 0.61), low average prediction errors and a good predictive power (Q2) for the training (4% and Q2LOO 0.57, respectively) and the test set (5% and Q2test 0.75, respectively) was obtained. Furthermore, the model predicted well the activity of an external validation set (on average 5% prediction errors), as well as the level of activity (low, moderate, high) of prenylated (iso)flavonoids against other Gram-positive bacteria. For the first time, the importance of formal charge, besides hydrophobic volume and hydrogen-bonding, in the anti-MRSA activity was highlighted, thereby suggesting potentially different modes of action of the different prenylated (iso)flavonoids.
14 citations
TL;DR: In this paper, the authors explored the possible antidiabetic action of narirutin, a flavanone family member, using in-silico and in-vivo methods.
Abstract: Citrus fruits and juices have been studied extensively for their potential involvement in the prevention of various diseases. Flavanones, the characteristic polyphenols of citrus species, are the primarily compounds responsible for these studied health benefits. Using in silico and in vitro methods, we are exploring the possible antidiabetic action of narirutin, a flavanone family member. The goal of the in silico research was to anticipate how narirutin would interact with eight distinct receptors implicated in diabetes control and complications, namely, dipeptidyl-peptidase 4 (DPP4), protein tyrosine phosphatase 1B (PTP1B), free fatty acid receptor 1 (FFAR1), aldose reductase (AldR), glycogen phosphorylase (GP), alpha-amylase (AAM), peroxisome proliferator-activated receptor gamma (PPAR-γ), alpha-glucosidase (AGL), while the in vitro study looked into narirutin's possible inhibitory impact on alpha-amylase and alpha-glucosidase. The results indicate that the studied citrus flavanone interacted remarkably with most of the receptors and had an excellent inhibitory activity during the in vitro tests suggesting its potent role among the different constituent of the citrus compounds in the management of diabetes and also its complications.
12 citations
TL;DR: Liquid chromatography-mass spectrometry approach is utilized and it is shown that within the leaves of Bidens pilosa plant the two okanin glycosides exist in unusual equal proportional distribution, which indicates that Bidens Pilosa plant is an alternative rich source of these highly sought-after antioxidant molecules.
Abstract: Bidens pilosa plant has been shown to produce okanin flavanone glycoside and its chalcone derivative. In most other plants, due to chalcone isomerase enzyme, the flavanone tends to exist in higher ...
11 citations
TL;DR: The results provide a novel and valuable strategy to reduce HAs via a low additive level of medicinal and edible plants and the correlation between experimental and calculated data could be applied to predict the inhibitory ability of inhibitors.
11 citations
TL;DR: In this article, a fast and accurate methodology for the quantification of the most abundant flavanone glycosides in citrus beverages has been developed, which relies on the use of paper spray mass spectrometry.
10 citations
10 citations
TL;DR: The results revealed E. africanus to be a rich source of flavonoids and natural anticancer agents, which could potentially be used in the development of new therapeutics for cancer treatment.
TL;DR: Hexanic fraction and chalcone 2′,4′-dihydroxy-5′-prenylchalcone showed potent results against human cancer cell lines tested and were identified by nuclear magnetic resonance of 1H and 13C data in comparison with literature.
TL;DR: In this article, the influence of different drying techniques, namely freeze drying and hot air oven drying, on flavonoids namely flavanone glycosides, antioxidant potential and total phenol content in immature dropped fruits of Citrus reticulata Blanco was investigated.
Abstract: Physiologically dropped immature Citrus reticulata Blanco fruits are regarded as waste and discarded in the citrus orchard but are a good source of bioactive compounds including flavonoids, antioxidants and total phenols. A study was undertaken to identify and quantify these bioactive compounds and to investigate the influence of different drying techniques, namely freeze drying and hot air oven drying, on flavonoids namely flavanone glycosides, antioxidant potential and total phenol content in immature dropped fruits of Citrus reticulata Blanco. Flavonoids were quantified in high-performance liquid chromatography (HPLC). The antioxidant activity were investigated with three assays azino-bis [3-ethylbenzthiazoline-6-sulfonic acid]) (ABTS), 2,2-diphenyl-1-picrylhydrazyl radical (DPPH), Ferric Reducing Ability of Plasma (FRAP) and total phenol content was determined. Freeze dried samples of 12 and 14 mm size retained maximum hesperidin flavonoid content (27.03% and 27.20%) as compared to the hot air dried samples (17.99%) and retained higher phenolic content ranged from 50.54–54.19 mg GAEL−1. The antioxidant activity in freeze dried fruits was from 12.21–13.55 mM L−1 Trolox and 15.27–16.72 mM L−1 Trolox with ABTS, DPPH assay and FRAP values ranging from 7.31–9.07 mM L−1 Trolox. Significant positive correlation was found between the flavonoid hesperidin with antioxidant assays and total phenolic content (TPC). The results showed that waste citrus fruits can act as potential source of bioflavonoids, especially hesperidin, and antioxidants for pharmaceutical as well as nutraceutical industry.
TL;DR: In this article, a transcriptomic and metabolite profiling analysis of licorice seedlings was conducted to identify 3,664 differentially expressed genes (DEGs) including transcription factor family MYB and basic helix-loop-helix (bHLH).
Abstract: Salinity stress significantly affects the contents of bioactive constituents in licorice Glycyrrhiza uralensis. To elucidate the molecular mechanism underlying the difference in the accumulation of these constituents under sodium chloride (NaCl, salt) stress, licorice seedlings were treated with NaCl and then subjected to an integrated transcriptomic and metabolite profiling analysis. The transcriptomic analysis results identified 3,664 differentially expressed genes (DEGs) including transcription factor family MYB and basic helix-loop-helix (bHLH). Most DEGs were involved in flavonoid and terpenoid biosynthesis pathways. In addition, 121 compounds including a triterpenoid and five classes of flavonoids (isoflavone, flavone, flavanone, isoflavan, and chalcone) were identified, and their relative levels were compared between the stressed and control groups using data from the ultrafast liquid chromatography (UFLC)-triple quadrupole-time of flight-tandem mass spectrometry (TOF-MS/MS) analysis. Putative biosynthesis networks of the flavonoids and triterpenoids were created and combined with structural DEGs such as phenylalanine ammonia-lyase (PAL), 4-coumarate-CoA ligase [4CL], cinnamate 4-hydroxylase [C4H], chalcone synthase [CHS], chalcone-flavanone isomerase [CHI], and flavonoid-3',5' hydroxylase (F3',5'H) for flavonoids, and CYP88D6 and CYP72A154 for glycyrrhizin biosynthesis. Notably, significant upregulation of UDP-glycosyltransferase genes (UGT) in salt-stressed licorice indicated that postmodification of glycosyltransferase may participate in downstream biosynthesis of flavonoid glycosides and triterpenoid saponins. Accordingly, the expression trend of the DEGs is positively correlated with the accumulation of glycosides. Our study findings indicate that key DEGs and crucial UGT genes co-regulate flavonoid and saponin biosynthesis in licorice under salt stress.
TL;DR: In this article, a total of 36 flavanones, including polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions.
TL;DR: In this paper, three new diglycosides (1-3), one new flavan-3-ol glycoside (4), and 12 previously reported compounds of the flavonol (5, 9), flavon-3ol (15), flavanone (8), 1,4napthoquinone (6, 7, 13, 14), 2,3-dehydroxynapthalene-1,4-dione (10-12), and phenolic acid (16) structure classes were isolated and identified.
Abstract: Phytochemical profiling was undertaken on the crude extracts of Drosera magna to determine the nature of the chemical constituents present. In total, three new flavonol diglycosides (1-3), one new flavan-3-ol glycoside (4), and 12 previously reported compounds of the flavonol (5, 9), flavan-3-ol (15), flavanone (8), 1,4-napthoquinone (6, 7, 13, 14), 2,3-dehydroxynapthalene-1,4-dione (10-12), and phenolic acid (16) structure classes were isolated and identified. Compounds 1-9, 13, 17, and 18 were assessed for antimicrobial activity, with compounds 6, 7, 8, and 9 showing significant activity. Compounds 1, 2, and 6 were also evaluated for anthelmintic activity against larval forms of Hemonchus contortus, with compound 6 being active.
TL;DR: In this article, the authors identify virucidal compounds, chemical constituents of plants from the genus Dracocephalum, which are rich in flavonoids and phenylpropanoid oligomers.
TL;DR: In this paper, the effect of water stress on the profile of flavonoids was evaluated in three tannin-containing (SC115, SC60, and SC720) and in three TANNIN-free (B.Tx635, SA 5330-MARTIN and SC373) sorghum genotypes.
TL;DR: In this article, the use of marine-derived fungi for enantioselective reduction of halogenated flavanones has been explored to obtain enantioenriched compounds with biological activities.
TL;DR: In this article, the chemical structures of isolated compounds were identified as four known flavanone derivatives (1-4), one new curcubinoyl derivative, jasmogin A (5), and six new curcinoyl-flavanone conjugates (6-11) by extensive spectroscopic analysis.
Abstract: Wild ginseng (Panax ginseng) adventitious root cultures were prepared by elicitation using methyl jasmonate and investigated further to find new secondary metabolites. Chromatographic fractionation of wild ginseng adventitious root cultures led to the isolation of eleven compounds. The chemical structures of isolated compounds were identified as four known flavanone derivatives (1-4), one new curcubinoyl derivative, jasmogin A (5) and six new curcubinoyl-flavanone conjugates, jasmoflagins A-F (6-11) by extensive spectroscopic analysis. Newly isolated curcubinoyl derivatives showed inhibitory activity against lipopolysaccharide-stimulated nitric oxide production in RAW 264.7 macrophages. Therefore, our present study suggested that elicitor stimulated plant cell cultures might contribute to the production of new metabolites.
TL;DR: In this paper, natural flavanone 1 (extracted from Eysenhardtia platycarpa) as lead compound and flavanones 1a-1d as its structural analogues were screened for anti-inflammatory activity using Molinspiration® and PASS Online in a computational study.
Abstract: There are a large number of remedies in traditional medicine focused on relieving pain and inflammation. Flavanones have been a potential source in the search for leading compounds and biologically active components, and they have been the focus of much research and development in recent years. Eysenhardtia platycarpa is used in traditional medicine for the treatment of kidney diseases, bladder infections, and diabetes mellitus. Many compounds have been isolated from this plant, such as flavones, flavanones, phenolic compounds, triterpenoid acids, chalcones, sugars, and fatty acids, among others. In this paper, natural flavanone 1 (extracted from Eysenhardtia platycarpa) as lead compound and flavanones 1a–1d as its structural analogues were screened for anti-inflammatory activity using Molinspiration® and PASS Online in a computational study. The hydro alcoholic solutions (FS) of flavanones 1, 1a–1d (FS1, FS1a–FS1d) were also assayed to investigate their in vivo anti-inflammatory cutaneous effect using two experimental models, a rat ear edema induced by arachidonic acid (AA) and a mouse ear edema induced by 12-O-tetradecanoylphorbol acetate (TPA). Histological studies and analysis of pro-inflammatory cytokines TNF-α, IL-1β, and IL-6 were also assessed in AA-inflamed rat ear tissue. The results showed that the flavanone hydro alcoholic solutions (FS) caused edema inhibition in both evaluated models. This study suggests that the evaluated flavanones will be effective when used in the future in skin pathologies with inflammation, with the results showing 1b and 1d to be the best.
TL;DR: In this article, the authors discuss the citrus naringenin reactivity, evaluating the chemo-and regioselective conditions, and the factors that lead to ring-opening isomerization.
TL;DR: In this paper, the authors used recombinant Escherichia coli expressing a C-glucosyltransferase from wasabi (WjGT1) to produce flavonol and flavone 6-C-glocosides by bioconversion.
Abstract: To produce flavonol and flavone 6-C-glucosides by bioconversion using recombinant Escherichia coli expressing a C-glucosyltransferase from wasabi (WjGT1). Escherichia coli expressing WjGT1 (Ec-WjGT1) converted flavones (apigenin and luteolin) and flavonols (quercetin and kaempferol) into their 6-C-glucosides in M9 minimal media supplemented with glucose, and released these products into the culture media. Ec-WjGT1 system also converts a flavanone (naringenin) into its C-glucoside at a conversion rate of 60% in 6 h. For scale-up production, apigenin, kaempferol, and quercetin were sequentially fed into the Ec-WjGT1 system at concentrations of 20–50 µM every 15–60 min, and the system was then able to produce isovitexin, kaempferol 6-C-glucoside, and quercetin 6-C-glucoside at an 89–99% conversion rate. The Ec-WjGT1 system quickly and easily produces flavone and flavonol 6-C-glucosides at high conversion rates when using sequential administration to avoid precipitation of substrates.
TL;DR: This is the first report on the insecticidal activity of the Cu2+ complexes of the flavanones naringin, naringenin and hesperidin of flavanone derivatives complexed to copper (II).
TL;DR: In this paper, an engineered strain of S. albus was used for the heterologous production of a large diversity of plant metabolites of the flavonoid family, including garbanzol and fustin, using Streptomyces albus as the production host.
Abstract: Flavonoids are important plant secondary metabolites, which were shown to have antioxidant, anti-inflammatory or antiviral activities. Heterologous production of flavonoids in engineered microbial cell factories is an interesting alternative to their purification from plant material representing the natural source. The use of engineered bacteria allows to produce specific compounds, independent of soil, climatic or other plant-associated production parameters. The initial objective of this study was to achieve an engineered production of two interesting flavanonols, garbanzol and fustin, using Streptomyces albus as the production host. Unexpectedly, the engineered strain produced several flavones and flavonols in the absence of the additional expression of a flavone synthase (FNS) or flavonol synthase (FLS) gene. It turned out that the heterologous flavanone 3-hydroxylase (F3H) has a 2-hydroxylase side activity, which explains the observed production of 7,4'-dihydroxyflavone, resokaempferol, kaempferol and apigenin, as well as the biosynthesis of the extremely rare 2-hydroxylated intermediates 2-hydroxyliquiritigenin, 2-hydroxynaringenin and probably licodione. Other related metabolites, such as quercetin, dihydroquercetin and eriodictyol, have also been detected in culture extracts of this recombinant strain. Hence, the enzymatic versatility of S. albus can be conveniently exploited for the heterologous production of a large diversity of plant metabolites of the flavonoid family.
TL;DR: A new dihydrochalcone, 2',4'-dimethoxydihydri-rochcones (2), together with 7 known compounds, 2,4'-dihydroxydi-drug-decomposition (2, 4), 2,3,4,7-tetramethoxy-9,10-dihdrophenanthrene (6), 5,hydroxy-2,3-4,4-trimethoxy (9, 10-dhydrophenanone) and 5,
TL;DR: In this article, 30 semi-synthetic DMC derivatives including 4′-O-monosubstituted-DMC (2), 7 O-acylated-4-hydroxycoumarin derivatives (3), stilbene-couMARIN derivatives (4), 2′,4′-disubstitized-dMC (5), and flavanone derivatives (6), were synthesised through acylation, alkylations, and sulfonylation.
Abstract: 2′,4′-Dihydroxy-6′-methoxy-3′,5′-dimethylchalcone (DMC, 1) was isolated from seeds of Syzygium nervosum A.Cunn. ex DC. exhibiting intriguing biological activities. Herein, thirty three DMC derivatives including 4′-O-monosubstituted-DMC (2), 7-O-acylated-4-hydroxycoumarin derivatives (3), stilbene–coumarin derivatives (4), 2′,4′-disubstituted-DMC (5), and flavanone derivatives (6), were synthesised through acylation, alkylations, and sulfonylation. These semi-synthetic DMC derivatives were evaluated for in vitro cytotoxicity against six carcinoma cell lines. It was found that most derivatives exhibited higher cytotoxicity than DMC. In particular, 4′-O-caproylated-DMC (2b) and 4′-O-methylated-DMC (2g) displayed the strongest cytotoxicity against SH-SY5Y with IC50 values of 5.20 and 7.52 μM, respectively. Additionally, 4′-O-benzylated-DMC (2h) demonstrated the strongest cytotoxicity against A-549 and FaDu with IC50 values of 9.99 and 13.98 μM, respectively. Our structure–activity relationship (SAR) highlights the importance of 2′-OH and the derivatisation pattern of 4′-OH. Furthermore, molecular docking simulation studies shed further light on how these bioactive compounds interact with cyclin-dependent kinase 2 (CDK2).
TL;DR: Enzymatic extraction is indicated as a good choice for recovering aglycone flavanones from CPB, and increased knowledge on the biological activity of this agroindustrial waste is increased, amplifying their application in food and pharmaceutical field.
Abstract: The citrus pectin by-product (CPB), generated from pectin industry, is a rich-source of flavanones, but not explored until now. As most of these compounds are inside vacuoles or bound to cell wall matrix, enzymatic hydrolysis was applied on their recovery, followed by hydroalcoholic and ultrasound extraction. Different parameters were studied: enzymes (β-glucosidase, tannase, and cellulase), their concentration (5, 10, and 20 U g−1 CPB), and reaction time (6, 12, and 24 h). Extracts were characterized in total phenolic content (TPC), antioxidant capacity (ORAC and DPPH assays), and polyphenolic profile (HPLC–DAD). All enzymatic treatments significantly improved CPB antioxidant capacity and TPC, compared with hydroalcoholic and ultrasound extraction. β-glucosidase (5 U) for 24 h was the most effective in polyphenol extraction and bioconversion, followed by β-glucosidase (5 U) for 12 h and tannase (5 U) for 24 h. Thus, the concentration of these enzymes was increased (10 and 20 U) to improve flavanones extraction. β-glucosidase at 20 U offered the highest amount of naringenin (77.63 mg 100 g−1 of CPB) and hesperetin (766.44 mg 100 g−1) obtained so far by biological processes. According to Person’s correlation analysis, TPC and antioxidant activity were highly correlated with CPB contents of hesperetin and naringenin. The aglycone flavanones are rarely found in natural sources and have higher biological potential than their glycosylated forms. Our results indicated enzyme-assisted extraction as a good choice for recovering aglycone flavanones from CPB, and increased knowledge on the biological activity of this agroindustrial waste, amplifying their application in food and pharmaceutical field.
TL;DR: In this article, four flavanone Schiff bases (E)-1-(2-phenylchroman-4-ylidene)thiosemicarbazide (FTSC) were synthesized and evaluated for their electronic and physicochemical properties using experimental and theoretical methods.
Abstract: Four flavanone Schiff bases (E)-1-(2-phenylchroman-4-ylidene)thiosemicarbazide (FTSC) (1), N′,2-bis((E)-2-phenylchroman-4-ylidene)hydrazine-1-carbothiohydrazide (FTCH) (2), (E)-N’-(2-phenylchroman-4-ylidene)benzohydrazide (FHSB) (3) and (E)-N′-(2-phenylchroman-4-ylidene)isonicotinohydrazide (FIN) (4) were synthesized and evaluated for their electronic and physicochemical properties using experimental and theoretical methods. One of them, (2), consists of two flavanone moieties and one substituent, the rest of the compounds (1, 3, 4) comprises of a flavanone-substituent system in relation to 1:1. To uncover the structural and electronic properties of flavanone Schiff bases, computational simulations and absorption spectroscopy were applied. Additionally, binding efficiencies of the studied compounds to serum albumins were evaluated using fluorescence spectroscopy. Spectral profiles of flavanone Schiff bases showed differences related to the presence of substituent groups in system B of the Schiff base molecules. Based on the theoretically predicted chemical descriptors, FTSC is the most chemically reactive among the studied compounds. Binding regions within human and bovine serum albumins of the ligands studied are in the vicinity of the Trp residue and a static mechanism dominates in fluorescence quenching.