Isolation of Amentoflavone fromGinkgo biloba

Lobstein-Guth, A.; Briançon-Scheid, Françoise; Victoire, C.; Haag–Berrurier, M.; Anton, Robert

doi:10.1055/s-2006-962549

Cited by 35 publications

(26 citation statements)

References 6 publications

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“…29) Amentoflavone were also isolated from the whole herbs of S. sinensis and the leaves of Celaenodendron mexicanum, Cupressocyparis leylandii, Ginkgo biloba, Rhus succedanea and Garcinia multiflora. 11,[30][31][32][33] Hinokiflavone (5) did not show any antiviral activities against RSV, PIV 3, and Flu A and B.…”

Section: Uncinoside a And B Two New Antiviral Chromone Glycosides Frmentioning

confidence: 99%

Uncinoside A and B, Two New Antiviral Chromone Glycosides from Selaginella uncinata

Wei

et al. 2003

Chem. Pharm. Bull.

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Viruses are the leading cause of respiratory infections in children and adults and are a major cause of morbidity and mortality worldwide. Respiratory viral infections contribute to be leading cause of morbidity, mortality, and economic loss throughout the world.1) Respiratory syncytial virus (RSV) is a major cause of pneumonia and bronchiolitis in infants, in children, and even in adults.2) Ribavirin and immunoglobulin preparations with high titers of RSV-specific neutralizing antibodies are currently approved for use to treat and prevent RSV infections. However, neither of these is cost-effective and simple to administer.3) Parainfluenza type 3 virus (PIV 3) is another respiratory virus caused infections in children. No chemotherapy agents and vaccine have been used to treat PIV 3 infections. 4) Therefore, the development of new antiviral agents with different mechanisms is most desirable. Traditional medicines utilizing natural products have been shown to contain antiviral compounds. [5][6][7][8][9] The screening of plants as a possible source of antiviral has led to the discovery of potent inhibitors of in vitro viral growth and the use of the ethnopharmacological approach enhances the probability of identifying new bioactive plant compounds. 10)Our interest has focused on the treatments for respiratory viral infections. In order to find more potent inhibitors of RSV and PIV 3, we have been looking for some inhibitory substances from natural sources. 11-17)Selaginella uncinata SPRING is a Chinese herb medicine widely distributed in south China, which has been used to treat infectious diseases and tumors. Previous phytochemical studies on the constituents of genus Selaginella led to the discovery of many compounds, including flavonoids and lignans. 18,19) As part of our continuous searching for novel antivial agents from medicinal plants, ethanol extract of the whole plants of S. uncinata was found to show significant inhibitory activities against RSV. The active extract led to the isolation and characterization of two new compounds, named uncinoside A (1) and uncinoside B (2) 20) together with three known compounds. Here we report the isolation and structure elucidation of the two new chromone glycosides and their antiviral activities against RSV, PIV 3, and influenza type A virus (Flu A). Results and DiscussionAn EtOH extract of the whole plant of S. uncinata was concentrated and partitioned with CHCl 3 and EtOAc. The CHCl 3 fraction was separated by silica gel column chromatography to yield two new chromone glycosides uncinoside A (1) and uncinoside B (2), and one known 5,7-dihydroxy-2,6-8-trimethylchromone (8-methyleugenitol) (3). The EtOAc fraction was separated by silica gel and polyamide column chromatography and prepared thin-layer chromatography (TLC) to afford two known biflavonoids: amentoflavone (4) 11,21) and hinokiflavone (5) 21,22) (Chart 1). The structure of the compound 3 was determined by the Xray diffraction analysis and spectral data. The structures of the other two known biflavonoids were...

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Section: Uncinoside a And B Two New Antiviral Chromone Glycosides Frmentioning

confidence: 99%

Uncinoside A and B, Two New Antiviral Chromone Glycosides from Selaginella uncinata

Wei

et al. 2003

Chem. Pharm. Bull.

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“…Among them, the main compound was the plant biflavonoid, amentoflavone. 10) Bioassays demonstrated potent inhibitory activity against RSV. The IC 50 value of amentoflavone was 5.5 mg/ml in vitro (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…[12][13][14][15] The other three known compounds from the ethanol extract were identified as 4Ј,7Љ-di-O-methylamentoflavone, 7Љ-O-methylrobustaflavone, and robustaflavone by spectroscopic analysis and comparison with published data. 16) Amentoflavone had been recently reported to have significant activity against influenza A and B viruses and exhibit moderate anti-herpes simplex virus (HSV)-1 and anti-HSV-2 activities with EC 50 values of 17.9 mg/ml (HSV-1) and 48.0 mg/ml (HSV-2).…”

Section: Resultsmentioning

confidence: 99%

Antiviral Amentoflavone from Selaginella sinensis

But

Ooi

et al. 2001

Biological & Pharmaceutical Bulletin

126

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Upper respiratory infection, especially in infants and children, is a common disease worldwide. Respiratory syncytial virus (RSV) has been recognized as a major cause of such infections.1) The nucleoside analog ribavirin has been used widely for treating RSV infections in healthcare settings such as hospitals and nursing homes. However, the treatment protocol, the potentially severe side effects and the emergence of drug-resistant mutants during long-term medication with this drug have often limited its administration to patients. 2)Therefore, the development of new antiviral agents with different mechanisms is most desirable. Traditional medicines utilizing natural products have been shown to contain antiviral compounds. [3][4][5][6][7] We screened for such compounds from natural products. In this paper, we report the isolation of active compounds from the whole herb of Selaginella sinensis (Selaginellaceae) and the content determination of amentoflavone in nine different species of Selaginella. Antiviral Assays The antiviral activity of test sample against RSV was measured by the plaque reduction assay. 8,9) Briefly, two-days old confluent monolayers of Hep 2 cells were infected with RSV at 100 plaque-forming units (PFU) per well in 0.5 ml maintenance medium . The inoculated cultures were incubated at 37°C in a CO 2 incubator with gentle agitation at 10-15 intervals to ensure uniform virus adsorption. Following 1 h virus adsorption, the inoculum was removed and 1.5 ml of agarose overlay medium containing 0.6% agarose in DMEM and 2% FBS were added to each well. When the agarose overlay became well-solidified, 1.5 ml of diluted test samples in maintenance medium were added to each well. A minimum of three different concentrations of each test sample was tested. One well per plate was added with 1.5 ml of maintenance medium without the test sample as control. The culture plates were incubated in the humidified CO 2 incubator for 4-5 d. The cultures were then fixed with 10% formalin in PBS and subsequently stained with 1% crystal violet in 20% ethanol upon removal of the agarose overlay. The number of plaques per well was enumerated macroscopically. The 50% inhibitory concentration (IC 50 ) was determined as the concentration of the test sample that reduced 50% of the plaque formation in the control wells. MATERIALS AND METHODS MaterialsExtraction and Isolation of Main Compound from the Herb of S. sinensis Air dried herb (5.0 kg) was extracted by refluxing with 90 l ethanol for three times, each time for 2 h. The ethanol solution was filtered and evaporated under reduced pressure to give a brownish ethanol extract (660 g). The ethanol extract was dissolved in water containing 0.5 N HCl and filtered. The precipitate was dissolved in water containing 0.5 N NaOH and filtered. The basic solution was adjusted to pH 1-3 with HCl, stayed overnight and filtered. The precipitate was washed with water to give a yellowish powder (195 g). Then this yellowish powder was extracted with chloroform, ethyl acetate and methanol by ...

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“…6 Os biflavonoides são compostos polifenólicos de ocorrência natural que são onipresentes nas plantas vasculares e têm apresentado propriedades biológicas promissoras. 7,8 Os dímeros de flavonoides resultam da ligação de duas unidades de flavona, flavanona, flavanonol, flavonol ou auronas ou misturas destas, além de ocorrerem, menos comumente, os dímeros de chalconas e isoflavonas. 9,10 Esta classe de metabolitos foi originalmente encontrada por Furukawa em 1929 no extrato das folhas de Ginkgo biloba, na forma de um sólido amarelo, posteriormente denominado de gingentina.…”

Section: Introductionunclassified

Ocorrência de biflavonoides em Clusiaceae: aspectos químicos e farmacológicos

Ferreira¹,

Carvalho²,

Silva³

2012

Quím. Nova

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Recebido em 10/4/12; aceito em 10/7/12; publicado na web em 5/10/12 OCCURRENCE OF BIFLAVONOIDS IN Clusiaceae: CHEMICAL AND PHARMACOLOGICAL ASPECTS. This work describes the biflavonoids found in species of Clusiaceae, particularly the genera Garcinia and Calophyllum, emphasizing the importance of these metabolites as chemical markers of this family, their contribution to the pharmacological potential of these species, besides the promising potential of these compounds in the search for new drugs.

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Isolation of Amentoflavone fromGinkgo biloba

Cited by 35 publications

References 6 publications

Uncinoside A and B, Two New Antiviral Chromone Glycosides from <i>Selaginella uncinata</i>

Uncinoside A and B, Two New Antiviral Chromone Glycosides from <i>Selaginella uncinata</i>

Antiviral Amentoflavone from Selaginella sinensis

Ocorrência de biflavonoides em Clusiaceae: aspectos químicos e farmacológicos

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