Flavanone Glycosides from <i>Citrus junos</i> and their Anti-Influenza Virus Activity

Kim, Ho Kyoung; Jeon, Won Kyung; Ko, Byoung‐Seob

doi:10.1055/s-2001-16484

Cited by 47 publications

(40 citation statements)

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“…By bioactivityguided fractionation, a new flavanone triglycoside, naringenin 7-O-(2′,6′-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (1), as well as hesperetin 7-O-(2′,6′-di-O-alpha-rhamnopyranosyl)-beta-glucopyranoside (2), hesperidin (3) and narirutin (4) were isolated from the fruits of Citrus junos v. Tanaka, Rutaceae) (Kim et al, 2001). In addition, (2) was reported for the first time from this plant and was found to inhibit the influenza A virus.…”

Section: Flavonoidsmentioning

confidence: 99%

Anti‐influenza agents from plants and traditional Chinese medicine

Wang

Zhao

et al. 2006

Phytotherapy Research

197

134

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Influenza is a serious threat to health in all parts of the world. The control and treatment of influenza depends mainly on chemical or biochemical agents and, to date, some anti-influenza agents have been isolated from plants as a result of chemical and pharmacological studies. These agents include a variety of polyphenols, flavonoids, saponins, glucosides and alkaloids. Traditional medicine focuses on the use of herbs and traditional Chinese medicine has performed well in clinical practice and shows a potential in the therapy of influenza and its symptoms. The present paper reviews some constituents and extracts from plants and traditional Chinese medicine with anti-influenza activity.

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Section: Flavonoidsmentioning

confidence: 99%

Anti‐influenza agents from plants and traditional Chinese medicine

Wang

Zhao

et al. 2006

Phytotherapy Research

197

134

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“…Recently, the existing bibliography on biological and pharmacological of these fl avonoids was reviewed (Tripoli et al, 2007). Several pharmacological studies have also shown that these fl avonoids possess anti-allergic (Inoue et al, 2002), anti-oxidant (Wang et al, 2003;Rajadurai et al, 2006), anti-infl uenza (Kim et al, 2001), anti-tumor (Vanamala et al, 2006) and anti-infl ammatory (Panthong et al, 2007) eff ects. Therefore, the screening and analysis of the fl avonoids, and extraction, separation and purifi cation of the abundant fl avonoids (narirutin, naringin and neohesperidin), is very important for the quality control and standardization of Fructus Aurantii Immaturus.…”

Section: Introductionmentioning

confidence: 99%

Application of an efficient strategy based on MAE, HPLC‐DAD‐MS/MS and HSCCC for the rapid extraction, identification, separation and purification of flavonoids from Fructus Aurantii Immaturus

Wang

Pan

Fan

et al. 2009

Biomedical Chromatography

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This study presents an efficient strategy based on microwave-assisted extraction (MAE), HPLC-DAD-MS/MS and high-speed counter-current chromatography (HSCCC) for the rapid extraction, identification, separation and purification of active components from the traditional Chinese medicine Fructus Aurantii Immaturus. An LC-DAD-MS/MS method was applied for the screening and structural identification of main components in crude extract, and five components were preliminarily identified as neoeriocitrin, narirutin, naringin, hesperidin and neohesperidin according to their UV and mass spectra. An efficient MAE method for the extraction of the three most abundant components (narirutin, naringin and neohesperidin) was optimized by the combination of univariate and multivariate approaches. The crude extract was then separated and purified by HSCCC and a total of 61.6 mg of narirutin, 207.3 mg of naringin and 159.5 mg of neohesperidin at high purities of 98.1, 97.2 and 99.5%, respectively, were obtained from 1.42 g of crude extract. The recoveries of these compounds were 86, 93 and 89%, respectively.

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“…In addition, plaque reduction assay were carried out. 8) Briefly, BHK-21 clone 15 at a final concentration of 2ϫ10 5 cell was seeded in 24-wells plates and stabilized for 24 h. Viral suspension at moi 0.02 and serial dilutions of the compounds were incubated for 1 h at 37°C, then 50 ml of each solution were added to the cells. After the 3 h of infection, cells were overlaid with 3% carboxymethylcellulose; after 24 h cells were fixed and stained with naphthol blue black, and the numbers of plaques were counted.…”

Section: Chemicalsmentioning

confidence: 99%

“…Flavanones, also called citrus flavonoids, possess many biological activities, 4) previous studies have shown its antiviral activity, hesperetin was found to inhibit the replication of herpes simplex virus type 1, poliovirus type 1, parainfluenza virus type 3 and influenza. 5,6) Hesperidin and Naringin had inhibitory activity on rotavirus infection. …”

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confidence: 99%

Anti-Sindbis Activity of Flavanones Hesperetin and Naringenin.

Paredes

Alzuru

Méndez

et al. 2003

Biological & Pharmaceutical Bulletin

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Sindbis virus is a positive single stranded RNA virus of the Togaviridae family. Wild type and a neurovirulent strain, NSV, have provided a valuable model system for studying alphavirus induced encephalomyelitis in mice. [1][2][3] In recent years, there has been a growing interest in search for antiviral substances with high efficacy, low toxicity and minor side effects, one approach is the search for viral inhibitors of plant origin. Flavanones, also called citrus flavonoids, possess many biological activities, 4) previous studies have shown its antiviral activity, hesperetin was found to inhibit the replication of herpes simplex virus type 1, poliovirus type 1, parainfluenza virus type 3 and influenza. 5,6) Hesperidin and Naringin had inhibitory activity on rotavirus infection. 7)Here, we report the effects of hesperetin, naringenin and its glycosides on BHK-21 clone 15 cells, as well as their inhibitory effect on the replication of a neuro-adapted strain of Sindbis (NSV). MATERIALS AND METHODS ChemicalsThe four flavanones studied were hesperidin, naringin and its aglycones hesperetin and naringenin, purchased from Sigma Chemical, St. Louis, Mo, U.S.A. A stock solution of each compound was prepared by dissolved in dimethyl sulfoxide (DMSO) and stored at Ϫ20°C.Cells and Virus BHK-21 clone 15 cells were kindly provided by Dr. Guadalupe Guzmán (Virology Department of the Pedro Kourí Institute, Havana, Cuba). The neurovirulent strain (NSV) of Sindbis virus was donated by Dr. Dianne Griffin (Medical School, John Hopkins University, Baltimore, U.S.A.). BHK-21 cells were grown in Eagle's minimal essential medium (MEM) supplemented with 5% inactivated fetal bovine serum (FBS), 2 mM glutamine and 50 mg/ml gentamicine (growth medium). The cells were maintained in a humidified atmosphere containing 5% CO 2 at 37°C. Virus stock NSV was grown in BHK-21 cells with maintenance medium (MEM, 1% FBS, 2 mM glutamine and 50 mg/ml gentamicine) for 24 h. Viral titer was obtained by plaque assay. 8)Cytotoxic Assay The effect of the compounds over cell viability was determined by a modified MTT assay. 9) Briefly, cells were adjusted to 4ϫ10 4 cells/100 ml in growth medium and seeded in a 96-well plate. Cells were stabilized for 24 h and then incubated with twofold serial dilutions of each compound from 25-0.09 mg/ml in maintenance medium. After 24 h 10 ml (10 mg/ml) of MTT were added to each well; it was metabolized for 3 h, and 100 ml of the lysis buffer (20% SDS, 50% N,N-dimethylformamide) was added. Plates were read at 570 nm after 18 h. Antiviral Activity The effect of these compounds over the mammalian cells was assayed in the same conditions as the cytotoxic assay. BHK cells were infected with NSV at a multiplicity of infection (moi) of 0.1 pfu/cell. The infections were carried out in the presence or absence of different concentrations of compound. After 24 h, the viability of the cells was determined by MTT assay as described before. In addition, plaque reduction assay were carried out. 8) Briefly, BHK-21 clone 15 at a final c...

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Flavanone Glycosides from Citrus junos and their Anti-Influenza Virus Activity

Cited by 47 publications

References 0 publications

Anti‐influenza agents from plants and traditional Chinese medicine

Anti‐influenza agents from plants and traditional Chinese medicine

Application of an efficient strategy based on MAE, HPLC‐DAD‐MS/MS and HSCCC for the rapid extraction, identification, separation and purification of flavonoids from Fructus Aurantii Immaturus

Anti-Sindbis Activity of Flavanones Hesperetin and Naringenin.

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