Estudo comparativo da excreção de flavonoides entre indivíduos eutróficos e obesos, após a ingestão de sucos de laranja, cv. Pera e cv. Moro / Comparative study of excretion of flavonoids among eutrophic and obese individuals, after ingestion of orange juice, cv. Pera and cv Moro

As laranjas e seus derivados, principalmente os sucos, possuem compostos bioativos, tais como os flavonoides, entre eles as flavanonas hesperidina e narirutina, que podem estar relacionados à promoção e benefícios à saúde. A absorção e metabolização de flavonoides podem ser afetadas por diversos fatores como a microbiota e fatores antropométricos, o que pode afetar a sua bioatividade. Assim, o objetivo deste estudo foi comparar o metabolismo e excreção dos flavonoides entre indivíduos eutróficos e obesos após a ingestão de sucos de laranja pasteurizado obtidos das cvs. Pera e Moro. Em um estudo cross-over randomizado 20 voluntárias eutróficas e 10 voluntárias obesas, com idade entre 19 e 40 anos, consumiram em dose única 600 mL de cada suco, que contém as flavanonas narirutina e hesperidina, além das antocianinas no suco Moro. Os metabólitos de flavanonas e de antocianinas foram identificados e quantificados em urina coletada em diferentes períodos de tempo durante 24 horas. Não foi observada diferença significativa na permeabilidade intestinal entre os grupos. Foram detectados e identificados 8 metabólitos de fase II da hesperitina e naringenina, principalmente mono e diglicuronidados e sulfatos, além de três ácidos fenólicos catabólitos de flavanonas formados pela microbiota intestinal, entre elas o ácido hipúrico, ácido protocatecuico e ácido 3-(3-hidroxifenil)-3-hidroxipropiônico. Os ácidos fenólicos foram os metabólitos majoritários recuperados na urina, principalmente o ácido hipúrico. Ainda, os metabólitos de fase II apresentaram maior excreção entre o período de 4-8h e 8-12h (13 a 27% do total de metabólitos excretados). Não foi observada diferença significante (p<0,05) no total de metabólitos de naringenina e hesperitina excretados na urina durante o período de 24 h entre os dois grupos e para os sucos de laranja, nem para o total de metabólitos, provavelmente devido à grande variabilidade interindividual na excreção. Assim, não foi observada diferença entre a metabolização de flavanonas de laranja entre os eutróficos e obesos e nenhuma correlação com os parâmetros antropométricos avaliados

Oranges and orange juices contain bioactive compounds, such as flavonoids, mainly the flavanones hesperidin and narirutin, which may be related to the promotion and health benefits. The absorption and metabolization of flavonoids can be affected by several factors such as the gut microbiota and anthropometric parameters, which may affect its bioactivity. Thus, the aim of this study was to compare the metabolism and excretion of flavonoids among eutrophic and obese people after ingestion of two pasteurized orange juice obtained from cvs. Pera and Moro. In a randomized cross-over study 20 eutrophic volunteers and 10 obese volunteers, aged 19-40 years, consumed a single dose of 600 mL of each juice. The metabolites of flavanones and anthocyanins were identified and quantified in urine collected at different time points for 24 hours. No significant difference in intestinal permeability was observed between groups. Eight Phase II metabolites of hesperitin and naringenin, mainly mono and diglycerides and sulfates, and three phenolic catabolites of flavanones formed by the gut microbiota were detected and identified, among them hippuric acid, protocatecuic acid and 3- (3-hydroxyphenyl) ) -3-hydroxypropionic acid. Phenolic acids were the major metabolites recovered in urine, mainly hippuric acid. Furthermore, phase II metabolites had greater excretion between the period of 4-8h and 8-12h (13-27% of total metabolites excreted). No significant difference (p <0.05) was observed in the total of naringenin and hesperitin metabolites excreted in the urine during the 24 h period between the two groups, probably due to interindividual variability in excretion. Thus, no difference was observed on metabolism of flavanones between the eutrophic and obese and no correlation was observed with the anthropometric parameters evaluated

Simultaneous Determination of 8 Components in Total Flavanones of Sedum sarmentosum Bunge by UPLC-MS/MS / 中国药房

OBJECTIVE:To establish a method for simultaneous determination of hyperoside,quercitrin,luteoloside, kaempferol,quercetin,rutin,luteolin and isorhamnetin in total flavanones of Sedum sarmentosum Bunge. METHODS:UPLC-MS/MS method was adopted. The determination was performed on ZOBAX SB C18column with mobile phase consisted of methanol-5 mmol/L ammonium formate aqueous solution(45:55,V/V)at the flow rate of 0.4 mL/min. The column temperature was 30 ℃, and sample size was 2 μL. The electrospray ionization source(ESI)was used;ion source temperature was 400 ℃;desolvation temperature was 300 ℃;desolvation gas flow was 600 L/h;capillary voltage was 3 000 V;nebuliser pressure was 45 psi;the work mode was multiple reaction monitoring mode;detection mode was negative ion mode. The established method was used to determine the contents of 8 components in 3 batches of total flavanones of Sedum sarmentosum Bunge. RESULTS:The linear ranges of hyperoside,quercitrin,luteoloside,kaempferol,quercetin,rutin,luteolin and isorhamnetin were 10.0-640.0,0.5-32.0, 4.5-288.0,8.0-512.0,50.0-3 200.0,2.0-128.0,12.5-800.0 and 25.2-1 612.8 ng/mL(r≥0.991 4),respectively. The limits of detection were 5.0,0.25,2.25,4.0,25.0,1.0,6.25 and 12.6 ng/mL,respectively.The limits of quantitation were 10.0,0.5,4.5, 8.0,50.0,2.0,12.5 and 25.2 ng/mL,separately. RSDs of precision,stability(24 h)and reproducibility tests were no more than 4.3%(n=6). The recoveries were 95.9%-100.6%,and RSDs were 1.5%-3.8%(n=6). The contents of hyperoside,quercitrin, luteoloside,kaempferol,quercetin,rutin,luteolin and isorhamnetin in 3 batches of total flavanones of Sedum sarmentosum Bunge were 507.88-560.37,42.95-50.36,63.52-71.80,1 695.10-1 753.27,10 569.28-10 612.99,25.76-30.13,2 795.22-2 877.43 and 4 869.55-4 971.30 μg/g,respectively. CONCLUSIONS:The established method can be used for simultaneous determination of 8 components in total flavanones of Sedum sarmentosum Bunge.

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

Objective To identify bioactive compound in pigeon pea leaves (Cajanus cajan) that inhibits Salmonella thypi (S. thypi). Methods The 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. Results Subfraction 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. Conclusions Naringenin shows antibacterial activity and can be developed to treat typhoid.

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

Objective: To identify bioactive compound in pigeon pea leaves (Cajanus cajan) that inhibits Salmonella thypi (S. thypi). Methods: The 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 spec-trometry and the antibacterial activity was tested against S. thypi by Kirby–Bauer method. Results: Subfraction 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. Conclusions: Naringenin shows antibacterial activity and can be developed to treat typhoid.

Association between dietary flavanones intake and lipid profiles according to the presence of metabolic syndrome in Korean women with type 2 diabetes mellitus

BACKGROUND/OBJECTIVES: This study was aimed at examining the association between dietary flavanones intake and lipid profiles according to the presence of metabolic syndrome (MetS) in Korean women with type 2 diabetes mellitus (T2DM). SUBJECTS/METHODS: A cross-sectional analysis was performed among 502 female T2DM patients (non-MetS group; n = 129, MetS group; n = 373) who were recruited from the Huh's Diabetes Clinic in Seoul, Korea between 2005 and 2011. The dietary intake was assessed by a validated semi-quantitative food frequency questionnaire (FFQ) and the data was analyzed using the Computer Aided Nutritional Analysis program (CAN-Pro) version 4.0 software. The intake of flavanones was estimated on the basis of the flavonoid database. RESULTS: In the multiple linear regression analysis after adjustment for confounding factors, daily flavanones intake was negatively associated with CVD risk factors such as total cholesterol, LDL-cholesterol, and apoB and apoB/apoA1 ratio only in the MetS group but not in the non-MetS group. Multiple logistic regression analysis revealed that the odds ratio for a higher apoB/apoA1 ratio above the median (> or = 0.74) was significantly low in the 4th quartile compared to that in the 1st quartile of dietary flavanones intake [OR: 0.477, 95% CI: 0.255-0.894, P for trend = 0.0377] in the MetS group. CONCLUSIONS: Dietary flavanones intake was inversely associated with the apoB/apoA1 ratio, suggesting a potential protective effect of flavanones against CVD in T2DM women with MetS.

Effect of wogonin on spatial memory and its possible mechanisms in chronic cerebral ischemia in rats / 国际脑血管病杂志

Objective To investigate the effect of wogonin on ethology and its possible mechanisms in chronic cerebral ischemia in rats.Methods Rats were randomly divided into a sham operation group,a wogonin intervention group,and a phosphate buffered solution (PBS) control group.A rat model of chronic cerebral ischemia was induced by the two-vessel occlusion method.Six weeks after modeling,the rats in the wogonin intervention group and the PBS control group were intragastric administrated with wogonin (50 μmol/L,10 ml/kg,once a day) and PBS with equal volume for 14 days.Morris water maze test was used to evaluate the spatial learning and memory function.Laser confocal three-dimensional vascular imaging was used to detect the vascular proliferation of ischemic brain tissue.5-Bromo-2-deoxyuridine (BrdU)immunochemical staining was used to detect the cell proliferation in ischemic brain tissue.Transmission electron microscope was used to observe the morphological changes of neural cells in cerebral ischernic region.Results The Morris water maze (n =8) showed that the trains of escape latency from the second to the fifth day in the wogonin intervention group were 43.45 ± 8.64 s,37.12 ± 1.31 s,34.75 ± 5.36 s,and 24.36 ± 5.43 s,respectively.They were significantly shorter than 51.69 ± 5.32 s,43.65 ± 9.21 s,50.19 ± 10.31 s,and 53.65 ± 7.15 s in the PBS control group (all P ＜ 0.05).The first quadrant swimming time of the wogonin intervention group was significantly longer than that of the PBS control group (26.16 ±3.29 s vs.14.38 ±2.16 s; P＜0.01).Laser confocal three-dimensional vascular imaging (n=4) showed that the capillary inner diameter in cerebral ischemia region of the wogonin intervention group was reduced significantly compared to the PBS control group (3.02 ±0.21 μm vs.3.35 ±0.18 μm; P ＜0.05),vascular density was increased significantly (205.80 ± 12.70/0.002 mm3vs.158.42 ± 10.92/0.002 mm3; P＜0.01),and total microvascular area was increased significantly (83 389 ± 4 026 μm2/0.002 mm3 vs.73 349 ±3 986 μm2/0.002 mm3; P＜0.01).Immunohistochemical staining (n =6) showed that the number of BrdU positive cells in the ischemic brain tissue of the wogonin intervention group was increased significantly compared to the PBS control group (24.62 ±3.25/HPF vs.9.87 ±2.89/HPF; P＜0.01).The observation of transmission electron microscope showed that the inflammatory edema in the intercellular spaces of the wogonin intervention group was significantly reduced compare to the PBS control group.Conclusions Wogonin can significantly improve the spatial learning and memory ability of chronic cerebral ischemia in rats,and its possible mechanisms may include the promotion of proliferation and angiogenesis in ischemic region and angiogenesis,and reduce inflammatory response.

Chemical constituents from rhizome of Matteuccia orientalis / 中草药

Objective: To study the chemical constituents from 60% ethanol extract of the rhizomes of Matteuccia orientalis. Methods: Chromatographic methods were used for the isolation and purification. Structures were identified on the basis of spectroscopic analysis. Results: Eleven compounds were isolated from M. orientalis and identified as (±)-thunberginol C (1), (2S)-5, 7, 3′, 5′-tetrahydroxyflavanone (2), naringenin (3), strobopinin (4), farrerol (5), leptorumol (6), cis-3, 5-dihydroxystilbene (7), dihydropinosylvin (8), paeonol (9), 3, 4-dihydroxybenzalacetone (10), and caffeic acid methyl ester (11). Conclusion: Compounds 1-11 are isolated from the plants of Matteuccia Todaro for the first time.

Antioxidant and antibacterial activity of extracts, fractions and isolated substances from the flowers of Acacia podalyriifolia A. Cunn. ex G. Don

The extracts and fractions from the flowers of A. podalyriifolia were analyzed previously for antibacterial activity using diffusion in disk, Antioxidant properties were evaluated by determining radical scavenging power (DPPH test) and total phenol content was measured (Folin method). The present study describes the in vitro antibacterial (determining minimum inhibitory concentration) and antioxidant activities (by thiobarbituric acid reactive species - TBARS method) for the ethanol extract, dichloromethane and ethyl acetate fractions and two flavanones (naringenin and 5-β-D-glycosyl-naringenin) isolated from the flowers of Acacia podalyriifolia A. Cunn. ex G. Don. The flavanones naringenin and 5-β-D-glycosyl-naringenin had not previously been obtained from this species. The most effective antibacterial activity was observed in the ethyl acetate fraction (MIC=0.25 mg mL-1 against Staphylococcus aureus ATCC 6538, MIC = 0.125 mg mL-1 against Staphylococcus epidermidis ATCC 12229, MIC=0.5 mg mL-1 against Streptococcus pyogenes ATCC 19615, Klebsiella pneumoniae ATCC 13883 and Proteus mirabilis ATCC 43071). The evaluated samples showed antioxidant activity on the TBARS test, especially for ethanol extract (1000 ppm), which was the most active (29.43% ± 0.65) followed by ethyl acetate fraction (1000 ppm, 24.84% ± 1,28), both demonstrating higher activity than that presented by ascorbic acid (1000 ppm, 21.73% ± 1.77), although lower than the BHT (1000 ppm 35.15% ± 3.42), both reference compounds. Naringenin and 5-β-D-glycosyl-naringenin demonstrated antioxidant action, but only naringenin inhibited the growth of gram-positive and gram-negative bacteria.

Os extratos e frações de Acacia podalyriifolia foram analisados previamente para a atividade antibacteriana através da difusão em disco e as propriedades antioxidantes foram verificadas pela determinação da capacidade removedora do radical livre DPPH e pela mensuração do conteúdo de fenólicos totais (Método de Folin). O presente estudo descreve as atividades antibacteriana (determinação da concentração inibitória mínima) e antioxidante (espécies reativas do ácido tiobarbitúrico - teste TBARS) para o extrato etanólico e as frações diclorometano e acetato de etila e para duas flavanonas (naringenina e 5-β-D-glicosil-naringenina) isoladas das flores de Acacia podalyriifolia A. Cunn. ex G. Don. As flavanonas naringenina e 5-β-D-glicosil-naringenina ainda não haviam sido obtidas desta espécie. A atividade antibacteriana mais efetiva foi observada com a fração acetato de etila (CIM=0,25 mg/mL contra Staphylococcus aureus ATCC 6538; CIM=0,125 mg/mL, contra Staphylococcus epidermidis ATCC 12229; CIM=0,5 mg/mL contra Streptococcus pyogenes ATCC 19615, Klebsiella pneumoniae ATCC 13883 e Proteus mirabilis ATCC 43071). As amostras avaliadas demonstraram atividade pelo teste TBARS, especialmente o extrato etanólico (1000 ppm), que foi o mais ativo (29,43% ± 0.65), seguido pela fração acetato de etila (1000 ppm, 24,84% ± 1,28), ambos demonstrando atividade mais elevada que a apresentada pelo ácido ascórbico (1000 ppm, 21,73% ± 1,77), ainda que menor que a do BHT (1000 ppm, 35,15% ± 3,42), ambas substâncias de referência. Naringenina e 5-β-D-glicosil-naringenina demonstraram ação antioxidante, porém somente a naringenina inibiu o crescimento de bactérias gram-positivas e gram-negativas.

Flavanones from aerial parts of Cordia globosa (Jacq.) Kunth, Boraginaceae / Flavanonas isoladas das partes aéreas de Cordia globosa (Jacq.) Kunth (Boraginaceae)

The phytochemical analysis of aerial parts of Cordia globosa, collected in the Municipality of Picuí, State of Paraíba, Brazil, resulted in the isolation and structural identification of narigenin-4',7-dimethyl ether (0.025 g) and eriodictyol (0.015 g). These compounds are the first flavanones aglycones isolated from the genus Cordia.

A análise fitoquímica das partes aéreas de Cordia globosa, coletadas no município de Picuí, PB, Brasil, resultou no isolamento e identificação estrutural da 7,4'-dimetilnarigenina (0,025 g) e eriodictiol (0,015 g). Estas duas flavanonas são as primeiras agliconas, desta classe, isoladas no gênero Cordia.

Chemical constituents of Rannunculus chinensis Bunge / 军事医学科学院院刊

Objective To investigate the chemical constituents of Rannunculus chinensis Bunge..Methods The chemical constituents of R.chinensis were isolated by chromatography on silica gel and Sephadex LH-20. The structures of compounds were identified by phytochemical properties and spectral analysis(MS and NMR).Results Ten compounds were isolated and identified as quercetin(1),kaempferol(2),luteolin(3),quercitrin(4), protocatechuic acid(5),gallic acid(6),ellagic acid(7),kaempferol-3-O-β-rutinoside (8),β-sitosterol (9) and 7-ketologanin (10). Conclusion Compound 10 is isolated from R.chinensis for the first time. Compounds 1,2,3,4,5,6,7 and 8 are obtained from the title plant for the first time.

FLAVONOIDES AISLADOS DE LAS INFLORESCENCIAS DE Piper hispidum Kunth (PIPERACEAE) Y DERIVADOS ACETILADOS ISOLATED / FLAVONOIDS FROM INFLORESCENCES OF Piper hispidum Kunth (PIPERACEAE) AND ACETYLATED DERIVATIVES / DERIVATIVES FLAVONOIDES ISOLADOS DAS INFLORESCÊNCIAS DE Piper hispidum Kunth (PIPERACEAE) E DERIVADOS ACETILADOS

A partir del extracto etanílico de las inflorescencias de la especie Piper hispidum Kunth (Piperaceae) fueron aislados tres flavonoides: 5-hidroxi-7-metoxiflavanona, 5-hidroxi-4,7-dimetoxiflavanona y 2,4,6-trimetoxidihidrochalcona. De las flavanonas aisladas fueron obtenidos los derivados acetilados: 5-acetoxi- 7-metoxiflavanona y 5-acetoxi-4,7- dimetoxiflavanona. Las estructuras fueron elucidadas empleando técnicas espectrocópicas y por comparacióncon datos de literatura. Los compuestos naturales y sus derivados fueron sometidos al bioensayo de letalidad frente a Artemia salina. El flavonoide 5-hidroxi-7-metoxiflavanona presenta la mayor actividad tóxica frente a los microcrustáceos CL50 1.8 [1]g/ml.

From the ethanolic extract of the inflorescences of Piper hispidum Kunth (Piperaceae) were isolated three flavonoids 5-hydroxy-7-methoxyflavanone, 5-hydroxy-4,7-dimethoxyflavanone and 2,4,6-trimethoxydihydrochalcone. The acetylated derivatives 5-acetoxy- 7-methoxyflavanone and 5-acetoxy- 4,7- dimethoxyflavanone were synthesized from the isolated pure flavanones. Characterization was mainly achieved by spectroscopic techniques and compared with literature data. Natural compounds and derivatives were subjected to brine shrimp lethality bioassay. The most toxic compound was the flavonoid 5-hydroxy- 7-methoxyflavanone with a LC50 1,8 [1]g/ml.

A partir do extracto etanílico das inflorescancias da especie Piper hispidum Kunth (Piperaceae) foram isolados tras flavonoides: 5-hidroxi-7-metoxiflavanona, 5-hidroxi-4,7-dimetoxiflavanona y 2,4,6-trimetoxidihidrochalcona. Das flavanonas isoladas foram sintetizados os derivados acetilados 5-acetoxi-7-metoxiflavanona y 5-acetoxi-4,7-dimetoxiflavanona. As estruturas foram elucidadas empregando técnicas espectrocópicas e por comparasau com dados da literatura. Os compostos naturais e seus derivados foram submetidos a bioensaáos de letalidade frente a Artemia salina. O flavonoide 5-hidroxi-7-metoxiflavanona presenta uma major atividad toxica frente aos microcrustaceos CL50 1,8 [1]g/ml.

Determination of Three Flavanones in the Effective Fraction of Flavone in Fructus Aurantii Immaturus by HPLC / 中国药房

OBJECTIVE:To establish an HPLC method for simultaneous determination of Naringin,Hesperidin and Neohesperidin in the effective fraction of flavone in Fructus Aurantii Immaturus.METHODS:Hypersil C18 column(250 mm?4.6 mm,5 ?m) was used with the mobile phase consisted of acetonitrile -0.1% phosphoric acid solution(20∶80) at a flow rate of 1.0 mL?min-1,and the detection wavelength was set at 283 nm and the column temperature was maintained at 30 ℃.RESULTS:The calibration curves of Naringin,Hesperidin and Neohesperidin were in good linearity over the ranges of 0.44～2.20 ?g(r=0.999 5),0.025 6～0.128 0 ?g(r=0.999 3),0.54 ～ 2.70 ?g(r=0.999 9),respectively.And the average recoveries for the three constituents were 99.41%,100.33% and 99.69%,respectively with RSD at 1.14%,1.47%,and 1.16%,respectively.CONCLUSION:The method is simple,accurate and reliable,and can be used for the quality control of Fructus Aurantii Immaturus.

Purification extraction of water-extraction solution of Ginkgo leaves with chitosan / 中成药

AIM:In order to improve the clarity and quality of Ginkgo leaf water-extraction solution,and optimize the production process. METHODS:The experiment was based on the optical absoiption and scattering rate,flocculation rate and loss in flavanones were used as two main parameters to estimate the effect of influencing factors on flocculation.It could be proved by analyzing the particle size in water-extraction solution before and after flocculation. RESULTS:The best flocculation technological parameters of water-extraction solution of Ginkgo leaf with chitosan were as follows:at flocculant concentration of 1.071 g/L,flocculation temperature of 40(?C),pH of 4.9. CONCLUSION:The flocculation of water-extraction solution of Ginkgo leaf with chitosan is effective and selective,it has the advantage over ethanol precipitation method.