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Concept: Flavones

168

Electrical penetration graphs (DC EPG) were used to monitor the feeding behavior of the pea aphid, Acyrthosiphon pisum Harris (Hemiptera: Aphididae) exposed to the flavonoids luteolin and genistein in artificial diets. The EPG patterns generated by aphids feeding on plants were used to interpret the patterns generated on the artificial diets. Addition of flavonoids to the diets generally prolonged the period of stylet probing (as indicated by EPG pattern d-C), reduced salivation (as indicated by pattern d-E1) and passive ingestion (as indicated by pattern d-E2), and also delayed the onset of salivation and passive ingestion. At higher concentrations (≥100 μg cm(-3) for luteolin, ≥1,000 μg cm(-3) for genistein), the flavonoids completely stopped salivation and passive ingestion. In most events associated with active ingestion (EPG pattern d-G), however, differences in feeding behavior did not statistically differ between the control diet and those with flavonoids; luteolin, and genistein only at 10 μg cm(-3) prolonged the time until the first d-G pattern was observed. The current findings demonstrate detrimental effects of the isoflavone genistein and the flavone luteolin on the feeding behavior of the pea aphid, A. pisum. This can be employed to create plants which are resistant to aphids and other herbivores.

Concepts: Insect, Isoflavones, Flavonoid, Hemiptera, Flavones, Aphid, Sternorrhyncha, Aphididae

168

Lipophilic flavonoids found in the Lamiaceae exhibit unusual 6- and 8-hydroxylations whose enzymatic basis is unknown. We show that crude protein extracts from peltate trichomes of sweet basil (Ocimum basilicum L.) cultivars readily hydroxylate position 6 of 7-O-methylated apigenin, but not apigenin itself. The responsible protein was identified as a P450 monooxygenase from the CYP82 family, a family not previously reported to be involved in flavonoid metabolism. This enzyme prefers flavones but also accepts flavanones in vitro, and requires a 5-hydroxyl in addition to a 7-methoxyl residue on the substrate. A peppermint (Mentha x piperita) homolog displayed identical substrate requirements, suggesting that early 7-O-methylation of flavones might be common in the Lamiaceae. This hypothesis is further substantiated by the pioneering discovery of 2-oxoglutarate-dependent flavone demethylase activity in basil, which explains the accumulation of 7-O-demethylated flavone nevadensin.

Concepts: Protein, Metabolism, Enzyme, Flavonoid, Lamiaceae, Basil, Ocimum basilicum, Flavones

28

Flavonols kaempferol, quercetin, myricetin and gossypetin, and flavones apigenin, acacetin, luteolin, orientin and tricin, are subjected to two AlCl(3) spectrophotometric methods used for determination of total flavonoid content. The method developed by Woisky and Salatino involves addition of AlCl(3) solution to the flavonoid solution and recording of optical density at 420nm. All flavonols except kaempferol have absorption maxima above 440nm and so readings at 420nm are erroneous. Among flavones, all except for luteolin and orientin, have absorption maxima below 400nm. Further, addition of CH(3)COOK and recording the absorbance at 415nm, as modified by Chang et al., works well for flavonols kaempferol, quercetin and myricetin, but not for gossypetin. The flavones luteolin and orientin absorbed above 400nm, whereas all others absorbed below 400nm. Examination of the results of both methods indicates they are inadequate, and should not to be considered as universal and standard methods for total flavonoid determination.

Concepts: Quercetin, Flavonoid, Flavones, Flavonols, Kaempferol, Myricetin, Luteolin, Rutin

26

Flavonoids in nine tissues of Nelumbo nucifera Gaertner were identified and quantified by high-performance liquid chromatography with diode array detector (HPLC-DAD) and HPLC-electrospray ionization-mass spectrometry (HPLC-ESI-MSn). Thirty-eight flavonoids were identified; eleven C-glycosides and five O-glycosides were discovered for the first time in N. nucifera. Most importantly, the C-glycosyl apigenin or luteolin detected in lotus plumules proved valuable for deep elucidation of flavonoid composition in lotus tissues and for further utilization as functional tea and medicine materials. Lotus leaves possessed the significantly highest amount of flavonoids (2.06E3±0.08 mg 100 g-1 FW) and separating and purifying the bioactive compound, quercetin 3-O-glucuronide, from leaves showed great potential. In contrast, flavonoids in flower stalks, seed coats and kernels were extremely low. Simultaneously, the optimal picking time was confirmed by comparing the compound contents in five developmental phases. Finally, we proposed the putative flavonoid biosynthesis pathway in N. nucifera.

Concepts: Chromatography, High performance liquid chromatography, Flavonoid, Glycoside, Seed, Flavones, Luteolin, Nelumbo nucifera

26

This study aims to identify and quantify the six major bioactive flavones of the traditional Chinese medicine Scutellariae Radix (RS), including baicalein, baicalin, wogonin, wogonoside, oroxylin A and oroxyloside in rat after oral administration of a standardized RS extract. A novel, sensitive and selective method for simultaneous determination of these six analytes in rat brain and plasma using solid phase extraction-liquid chromatography-tandem mass spectrometry (SPE-LC/MS/MS) was developed and fully validated. The lower limits of quantification (LLOQs) for the six RS flavones in brain tissue were 0.02nmol/g. The LLOQs in plasma were 0.005nmol/ml for B, W and OA, 0.025nmol/ml for WG and OAG, and 0.1875nmol/ml for BG. The current study provides novel evidence of the presence of all the tested RS flavones and an isoform of BG (BG', probably baicalein-6-O-glucuronide) in the rat brain after oral administration of RS extract, suggesting their ability to permeate through the blood-brain barrier. The method was also successfully applied to the pharmacokinetic study of all these analytes in plasma after oral administration of RS extract (300mg/kg) to Sprague-Dawley rats. The developed assay method provides a useful tool for both preclinical and clinical investigations on the disposition of RS flavones in brain and plasma.

Concepts: Brain, Phase, Rat, Flavones, Laboratory rat, Oroxylum indicum, Wogonin, Baicalein

25

The influence of phenological stages on chemical composition of Scutellariae Radix (SR), the root of Scutellaria baicalensis Georgi, was investigated. In order to deal with a large quantity of samples, a rapid ultra-performance liquid chromatographic (UPLC) was first developed and validated for the simultaneous quantification of five flavonoids, namely baicalin (baicalein-7-O-β-D-glucuronide, BG), wogonoside (wogonin-7-O-β-D-glucuronide, WG), baicalein (BA), wogonin (WO), oroxylin A (OA) in the samples. Good linearity was obtained in the range of 0.742-389 ng (r (2)  > 0.9999) and satisfactory recoveries were obtained (101.72-104.56 %) with the RSD value below 5.0 %, for all analytes. Also, extraction conditions were optimized to obtain maximum extractive contents of the five flavonoids. Content variations of the five active ingredients in 225 samples from three different origins were investigated in five major phenological periods. It was found that the effect of phenology on the contents of the tested five flavonoids was similar in the three origins. The contents of flavone O-glycosides, i.e., BG and WG accumulated to the highest level in leaf expansion period, while flavonoid aglycones, i.e., BA, WO and OA appeared a maximum concentration in flowering period. The UPLC method established in this study was rapid and of good accuracy, repeatability and resolution, and hence can assist in the quality control of SR.

Concepts: Time, Stage, Flavonoid, Flavones, Oroxylum indicum, Scutellaria baicalensis, Wogonin, Baicalein

24

A simple and sensitive liquid chromatography method with diode array detector was established for simultaneous determination of 11 components (geniposidic acid, chlorogenic acid, caffeic acid, geniposide, luteoloside, isochlorogenic acid C, baicalin, luteolin, wogonoside, baicalein and wogonin) in various commercial Yinzhihuang preparations and their herbs by optimizing the extraction, separation and analytical conditions. Eleven components were identified on the basis of their retention times and mass spectra. Chromatographic separation was performed on a C18 analytical column with a gradient elution of acetonitrile and 0.1% formic acid water solution at a flow rate of 1.0 mL/min. The linearity, precision and accuracy of the data obtained were acceptable. The method was used to analyze four Yinzhihuang preparations (powder, capsule, oral liquid and injection) and related herbs (Radix Scutellariae, Flos Lonicerae, Herba Artemisiae Scopariae and Fructus gardeniae). Results suggested that the optimized method could be considered as a good approach to control the quality of Yinzhihuang preparations and their herbs.

Concepts: Protein, Chromatography, High performance liquid chromatography, Analytical chemistry, Gas chromatography, Caffeic acid, Flavones, Chlorogenic acid

2

Flavones found in plants display various biological activities, including anti-allergic, anti-viral, anti-inflammatory, anti-oxidation, and anti-tumor effects. In this study, we investigated the anti-tumor effects of flavone, apigenin and luteolin on human breast cancer cells.

Concepts: Cancer, Breast cancer, Metastasis, Cancer staging, Organism, Chemotherapy, Pleural effusion, Flavones

1

Flavones are a major group of flavonoids with diverse functions and extensively distributed in land plants. There are two different classes of flavone synthase (FNS) enzymes that catalyze the conversion of the flavanones into flavones. The FNSI class comprises soluble Fe2+/2-oxoglutarate-dependent dioxygenases, and FNSII enzymes are oxygen- and NADPH-dependent cytochrome P450 membrane-bound monooxygenases. Here, we describe the identification and characterization of two FNSI enzymes from Zea mays and Arabidopsis thaliana. In maize, ZmFNSI-1 is expressed at significantly higher levels in silks and pericarps expressing the 3-deoxy flavonoid R2R3-MYB regulator P1, suggesting that ZmFNSI-1 could be the main enzyme for the synthesis of flavone O-glycosides. We also show here that AtDMR6, the Arabidopsis homologous enzyme to ZmFNSI-1, has FNSI activity. While dmr6 mutants show loss of susceptibility to Pseudomonas syringae, transgenic dmr6 plants expressing ZmFNSI-1 show similar susceptibility as WT plants, demonstrating that ZmFNSI-1 can complement the mutant phenotype. AtDMR6 expression analysis showed a tissue and developmental stage-dependent pattern, with high expression in cauline and senescing leaves. Finally, we show that Arabidopsis cauline and senescing leaves accumulate apigenin, demonstrating that Arabidopsis thaliana plants have a FNSI activity involved in the biosynthesis of flavones. The results presented here also suggest a cross-talk between the flavone and salicylic acid pathways in Arabidopsis; in this way, pathogens would induce flavones to decrease salicylic acid and hence increase susceptibility.

Concepts: Bacteria, Metabolism, Developmental biology, Model organism, Starch, Arabidopsis thaliana, Flavonoid, Flavones

0

Two flavone di-C-glycosides, a pair of isomers, were isolated from Scutellaria baicalensis. The structures of compounds 1 and 2 were elucidated by means of physical data, including 1D and 2D NMR and HR-ESI-MS. Supporting theoretical calculations of the compound conformational landscape has also been conducted for geometry optimization. This is the first report of the natural occurrence of β-furanoarabinoside. In addition, the effects of compounds 1 and 2 on NO, pro-inflammatory cytokines, PGE2 and COX-2 levels were measured in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. The pair of isomers exhibited significant inhibitory effects on inflammation.

Concepts: Enzyme, Mathematics, Anti-inflammatory, Flavones, Scutellaria baicalensis, Wogonin