Protective Actions of Blumea Flavanones on Primary Cultured Hepatocytes and Liver Subcellular Organelle against Lipid Peroxidation

To search for the protective actions of blumea flavanones (BFs) on hepatocytes and hepatic subcellular organelle against lipid peroxidation, monkey′s hepatocytes were isolated and cultured with or without blumea flavanones, then damaged by FeSO 4 cysteine or CCl 4. The lipid peroxidation (malondialdehyde production) and alteration in hepatocyte membrane (leakage of GPT) were estimated. Hepatic subcellular organelles were also isolated and incubated with or without blumea flavanones, then injured by FeSO 4 ascorbate. The generation of malondialdehyde(MDA) was measured. It was found that BFs 10 and 100 μmol·L 1 inhibited the MDA generation and GPT (glutamic pyruvic transaminase) leakage out of hepatocytes that were induced by CCl 4 or FeSO 4 cysteine. BFs could prevent lipid peroxidation initiated by FeSO 4 ascorbate in subcellular organelle suspension. Among BFs, BF 2 possessed the strongest activity. Conclusion: Blumea flavanones possess antioxidation activities that protect monkey′s hepatocytes and hepatic subcellular organelle against injuries induced by FeSO4 or CCl 4.

Two New Antibacterial Flavanones from Sophora flavescens

Two new lavandulylated flavanones,（2R, 3R）-8-1avandulyl-2＇-methoxy-5, 7, 4＇-trihydroxyflavanonol （1） and 8-1avandulyl-5,7, 4＇-trihydroxyflavonol （2）,were isolated from the dry roots of S opharaflavescens.Their structures were eiucidated on the basis of spectroscopic data. Compounds 1 and 2 exhibited significant antibacterial activities.

Influence of Mobile Phase Composition on the Enantioseparation of Methoxyl Flavanones with Self-prepared CDMPC Column and Chiral Recognition Mechanism

The influence of different alcohol modifiers in mobile phase on the chiral separation of 4-methoxyl flavanone, 5-methoxyl flavanone and 6-methoxyl flavanone on cellulose tris (3, 5-dimethylphenylcarbamate) (CDMPC) column was studied and the chiral recognition mechanism was discussed. Using hexane-tert-butanol (1.31 mol L-1) as the mobile phase, those three methoxyl flavanones were excellently separated on CDMPC chiral column.

Chemical modification of acetaminophen：PASS assisted in vivo antiinflammatory activity of chalcones,flavanones and Schiff bases

In the present study,synthetic chalcones,flavanones and Schiff bases were prepared starting from paraceamol,and evaluated their anticipated anti-inflammatory activity.Chalcones were synthesized by reacting 3-acetyl-4-hydroxy acetanilide and aromatic aldehydes in alcoholic potassium hydroxide(KOH) solution under Claisen-Schmidt condensation conditions.The chalcones were cyclized in the presence of piperidine in isoamyl alcohol to obtain flavonone derivatives.Schiff bases were synthesized by condensing 3-acetyl-4-hydroxy anilines with aromatic aldehydes in the presence of HCl.These Schiff bases were further reacted with other aromatic aldehydes in alcoholic KOH solution.PASS cheminformatics software was used to predict the anti-inflammatory activity of synthesized compounds.PASS software predicted that chalcone-based Schiff bases 6a–d contained structural features that can exhibit anti-inflammatory activity.All the prepared derivatives of acetaminophen exhibited moderate to excellent in vivo anti-inflammatory activity in carrageenan-induced edema in rat paw.All the Schiff bases coupled chalcones showed good anti-inflammatory activity compared with the reference drug,diclofenac.Further evaluation of their therapeutic potential and safety profile is required in the future study.

Functional analysis of flavanone 3-hydroxylase(F3H)from Dendrobium officinale,which confers abiotic stress tolerance

Flavonoids are important bioactive components in Dendrobium officinale,a medicinal orchid.They are involved in many biological activities,including protecting plants against biotic and abiotic stresses.Research on the key genes related to flavonoid biosynthesis in D.officinale is limited.In this study,one of the key flavonoid biosynthesis genes,flavanone 3-hydroxylase(F3H),was characterized from D.officinale.The open reading frame of DoF3H was 1134 bp long and it encoded a 377-amino acid protein.The DoF3H protein showed considerably high homology with F3H proteins from other plant species and shared a common evolutionary ancestor with other F3Hs.DoF3H transcripts were detected in different organs of adult plants and mainly accumulated in flowers,followed by roots,stems and leaves,a pattern that was similar to the content of flavonoids.Recombinant DoF3H protein,which was localized in the cytosol,could convert naringenin to dihydrokaempferol.The mRNA levels of DoF3H were significantly induced by salt and cold stresses.Furthermore,the heterologous expression of DoF3H in Escherichia coli conferred it higher tolerance to salt and cold stresses.These results provide insight into the molecular function of DoF3H in the biosynthesis of flavonoids,and provide a new application for improvement of abiotic tolerance in D.officinale.

Flavanone and flavonoid hydroxylase genes regulate fiber color formation in naturally colored cotton

Using naturally colored cotton(NCC)can eliminate dyeing,printing and industrial processing,and reduce sewage discharge and energy consumption.Proanthocyanidins(PAs),the primary coloration components in brown fibers,are polyphenols formed by oligomers or polymers of flavan-3-ol units derived from anthocyanidins.Three essential structural genes for flavanone and flavonoid hydroxylation encoding flavanone-3-hydroxylase(F3H),flavonoid 3’-hydroxylase(F3’H)and flavonoid 3’5’-hydroxylase(F3’5’H)are initially committed in the flavonoid biosynthesis pathway to produce common precursors.The three genes were all expressed predominantly in developing fibers of NCCs,and their expression patterns varied temporally and spatially among NCC varieties.In GhF3Hi,GhF3’Hi and GhF3’5’Hi silenced lines of NCC varieties XC20 and ZX1,the expression level of the three genes decreased in developing cotton fiber,negatively correlated with anthocyanidin content and fiber color depth.Fiber color depth and type in RNAi lines changed with endogenous gene silencing efficiency and expression pattern,the three hydroxylase genes functioned in fiber color formation.GhF3H showed functional differentiation among NCC varieties and GhF3’H acted in the accumulation of anthocyanin in fiber.Compared with GhF3’H,GhF3’5’H was expressed more highly in brown fiber with a longer duration of expression and caused lighter color of fibers in GhF3’5’H silenced lines.These three genes regulating fiber color depth and type could be used to improve these traits by genetic manipulation.

Dietary flavonoid intake and risk of stomach and colorectal cancer

Stomach and colorectal cancers are common cancers and leading causes of cancer deaths.Because the alimentary tract can interact directly with dietary components,stomach and colorectal cancer may be closely related to dietary intake.We systematically searched published literature written in English via PubMed by searching for terms related to stomach and colorectal cancer risk and dietary flavonoids up to June 30,2012.Twenty-three studies out of 209 identified articles were finally selected for the analysis.Log point effect estimates and the corresponding standard errors were calculated using covariate-adjusted point effect estimates and 95%CIs from the selected studies.Total dietary flavonoid intake was not associated with a reduced risk of colorectal or stomach cancer [odds ratio(OR)(95%CI) = 1.00(0.90-1.11) and 1.07(0.70-1.61),respectively].Among flavonoid subclasses,the intake of flavonols,flavan-3-ols,anthocyanidins,and proanthocyanidins showed a significant inverse association with colorectal cancer risk [OR(95%CI) = 0.71(0.63-0.81),0.88(0.79-0.97),0.68(0.56-0.82),and 0.72(0.61-0.85),respectively].A significant association was found only between flavonols and stomach cancer risk based on a limited number of selected studies [OR(95%CI) = 0.68(0.46-0.99)].In the summary estimates from casecontrol studies,all flavonoid subclasses except flavones and flavanones were inversely associated with colorectal cancer risk,whereas neither total flavonoids nor any subclasses of flavonoids were associated with colorectal cancer risk in the summary estimates based on the cohort studies.The significant association between flavonoid subclasses and cancer risk might be closely related to bias derived from the case-control design.There was no clear evidence that dietary flavonoids are associated with reduced risk of stomach and colorectal cancer.

Antibacterial activity of naringenin-rich fraction of pigeon pea leaves toward Salmonella thypi

To identify bioactive compound in pigeon pea leaves (Cajanus cajan) that inhibits Salmonella thypi (S. thypi).MethodsThe leaf sample was powdered and macerated with methanol and fractioned by liquid-liquid extraction using ethyl acetate. The fraction was chromatographed and the isolates were identified for major component with liquid chromatography-mass spectrometry and the antibacterial activity was tested against S. thypi by Kirby-Bauer method.ResultsSubfraction 1 from the ethyl acetate fraction formed a yellowish solid with m/z 272, identified as naringenin. The naringenin-rich fraction shows fairly well inhibitory toward S. thypi in comparison with chloramphenicol.ConclusionsNaringenin shows antibacterial activity and can be developed to treat typhoid.

Desmosflavanone Ⅱ: A New Flavanone from Desmos cochinchinensis Lour

A new flavanone was isolated from the roots of Desmos cochinchinensis Lour Its chemical structure was elucidated by spectral analysis as 7 hydroxy 5 methoxy 8 formyl 6 methylflavanone, named desmosflavanone Ⅱ

First total synthesis of (±)-abyssinoflavanone V

The total synthesis of （±）-abyssinoflavanone V was first achieved through C-prenylation, selective protection of phenolic hydroxyl group, aldol condensation, cyclization and deprotection starting from cheap 4-hydroxybenzaldehyde and 2,4,6- trihydroxyacetophenone, with total yield 24%. All structures of new compounds were confirmed by IR, 1^H NMR and MS.

A New Flavanone and a New Flavanone Glycoside from Scutellaria baicalensis

A new flavanone （2S）-5, 7, 2＇, 5＇-tetrahydroxy-flavanone 1 together with a new flavanone glycoside （2S）-5, 7, 2＇, 5＇-tetrahydroxy-flavanone 7-O-13-D-glucopyranoside 2, were isolated from the dry roots of Scutellaria baicalensis. Their structures were elucidated on the basis of spectroscopic data.

First total synthesis of (±)-puyanin and (±)-4'-O-methylbonannione

A facile approach for the first total synthesis of two naturally occurring geranylated flavonoids,（±）-puyanin 1 and（±）-4＇-O- methylbonannione 2 has been obtained with total yield 27%and 21%,respectively.The key steps were regioselective cyclization of geranylated trihydroxychalcone and regioselective geranylation of 2,4,6-trihydroxyacetophenone.

Isolation, Crystal Structure, and Anti-inflammatory Activity of Sakuranetin from Populus tomentosa

The title compound of sakuranetin, a main active flavanone component, was first isolated from Populus tomentosa Carr. and characterized by X-ray single-crystal diffraction analysis It crystallizes in the monoclinic lattice, space group P21/c with a = 12.8531（12）, b = 5.7141（3）, c = 18.0355（12） A, β = 97.333（8）°, V = 1313.77（16） A^3, Z= 4, Mr = 286.27, C16H14O5,μ（MoKa） = 0.108 mm^-1, Dc = 1.447 g/cm^3, F（000） = 600, the final R = 0.0350 and wR = 0.0859 for 2571 independent reflections （Rint = 0.0246） which were used in all calculations. The molecular crystal structure of sakuranetin shows relative stereochemistry of 5,4′-dihydroxy-7-methoxyflavanone. Intermolecular hydrogen bonds together with the continuous π-π interactions construct the three-dimensional architecture of the title compound. The preliminary bioassay reveals that the title compound exhibits moderate anti-inflammatory activity in vitro against the nitric oxide release.

Solvent-free Synthesis of Flavanone over New Hybrid Mesoporous Base Catalysts

Benzyl and anthracenemethyl groups were respectively bonded to the N atoms of 3-aminopropyl functionalized mesoporous SBA-15（APS-SBA-15） to obtain two new base catalysts over which the condensation reaction of benzaldehyde and 2＇-hydroxyacetophenone was studied.Good catalytic activities and high selectivities for flavanones were obtained in solvent-free reactions,which is attributed to the effect of benzyl and anthracenemetyl groups on the base sites of catalysts and the steric hindrance of futher reaction of flavanone with benzaldehyde.

Synthesis of New Flavanone Derivatives of Farrerol and Preliminary SAR Studies on Anti-VSMCs Vegetation Activity

A series of new flavanone derivatives of farrerol was designed and synthesized as a potent inhibitor of vascular smooth muscle cells（VSMCs） vegetation according to a convenient method. The structures of all the synthesized compounds were confirmed by 1H NMR, 13C NMR and EIHR-MS. The biological activities of these compounds against VSMCs in vitro were evaluated. The assay results indicate that two compounds, 5,7-dihydroxy-6,8-dimethyl- 2-（2-nitrophenyl）chroman-4-one（7f） and 2,3-dibromo-4,5-dihydroxydiphenylmethanone（7j） exhibited high activity against VSMCs in vitro with IC50 values of 9.9 and 6.7 μmol/L, respectively, and the preliminary structure-activity relationship（SAR） was described.

Two new flavanone glycosides from Macrothelypteris torresiana (Gaud.) Ching

Two new flavanone glycosides 1 and 2 were isolated from the aerial parts of Macrothelypteris torresiana （Gaud.） Ching. The structures of two products were identified as （2S）-5,7,2＇,5＇-tetrahydroxyflavanone-2＇-O-β-D-6＂-O-acetylglucopyranoside and （2S）- 5,7,2＇,5＇-tetrahydroxyflavanone-2＇-O-β-D-glucopyranoside on the basis of their chemical and spectral analysis, respectively.

New flavonoids from bioactive extract of Algerian medicinal plant Launeae arborescens

Objective:To investigate the butanol fraction of the water/acetone extract and isolate of the new flavonoids from Launeae arboescens.Methods:The compounds were isolated by liquid chromatographic methods and their structures were identified by using spectroscopic analysis.Results:The isolated compounds were identified as:7-0-[α-rhamnopyranosyl 4',5,6-Trihydroxy flavone 1,4',5'-Di-Methoxy 7-(5"-Me Hexan)1-oyl flavanone 2,3"-isopropyl pyrano[1":7,4":6]3',4',5',5-Tetrahydroxy flavanone 3,5,4',5'-Tri-Hydroxy 7-(3"-Me butan)-yl flavanone 4.5,7-Dihydroxy-2',4',5'-trimethoxy-isoflavanone 5,5,6,7,4'-tetrahydroxy flavonol 6,7-O-[α-rhamnopyranosyl-(1->6)-β-glucopyranosyl]-4',5,7-tri-hydroxy-flavanone 7,7-O-[α-rhamnopyranosyl-(1->6)-β-glucopyranosyl]3',5-Dihydroxy 4'-Methoxy flavanone 8.Conclusions:The presence of different types of bioactive flavonoids in Launeae arhoescens extract can explain the large ethnopharmacological uses and the potential activity of this medicinal plant.

A new lavandulyl flavonoid from Sorphora flavescens Ait

A new lavandulyl flavonoid was isolated from the rhizome of Sorphora flavescens. The structure of new compound was elucidated on the basis of spectral methods including 2D NMR. And it showed potent cytotoxic activity against Hela ceils with IC50 of 1.1 μmol/L.

Studies on the Reaction of Benzopyran-4-one with Hydroxylamine Hydrochloride

It is reported that 6-methyl-flavanone oxime would rearrange to isoxazoline in the presence of trifluroacetic acid and the rearrangement would not take place in anhydrous ethanol with catalytic amount of pyridine. However, 6-nitro-benzopyran-4-one when treated with hydroxylamine hydrochloride, gave oxime and its isomeric isoxazoline through rearrangement under acid or alkali condition.

Therapeutic Applications of Naringenin, a Flavanone Enriched in Citrus Fruits, for Disorders beyond Diabetes

In recent years,there has been an increase in epidemiological studies to highlight the health benefits of plant secondary metabolites.Flavonoids(polyphenolic plant secondary metabolites)are recently emerging as an important source for the discovery of new drugs increasing their pharmaceuticals,nutraceutical and medicinal applications.Naringenin is a flavanone,enriched in citrus fruits,tomatoes,bergamot,etc.which has been evaluated extensively for managing diabetes.However,in addition to this,naringenin had been ascribed to various important biological activities like antioxidant,antiviral,anticancer,anti-inflammatory,antiestrogenic,etc.This article aims at highlighting the therapeutic value of naringenin in managing disorders other than diabetes and its role in regulating gene expression by altering chromatin structure as histone deacetylase inhibitor.The understanding of these phenomena will increase the overall knowledge of the various health-promoting effects of citrus fruits.