Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis

Ryu, Young Bae; Kim, Young Ho; Park, Su‐Jin; Chang, Jong Sun; Rho, Mun‐Chual; Bae, KiHwan; Park, Ki Hun; Lee, Woo Song

doi:10.1016/j.bmcl.2009.12.106

Cited by 88 publications

(53 citation statements)

References 28 publications

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“…11,12) This is because NA inhibitors from natural plants as these can be readily applied to neutraceutics for the prevention of virus infection. For instance, our previously reported that polyphenols derived from Rhodiola rosea 13) and Glycyrrhiza uralensis 14) exhibit potent NA-inhibitory activity and Du and co-workers 15) suggested the order of potency for NA inhibition in flavonoids. A recent study reported that sappanchalcone (1) and brazilin (12) …”

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confidence: 99%

Homoisoflavonoids from <i>Caesalpinia sappan</i> Displaying Viral Neuraminidases Inhibition

Jeong

Kim

et al. 2012

Biological & Pharmaceutical Bulletin

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In this study, twelve neuraminidase (NA) inhibitory compounds 1-12 were isolated from heartwood of Caesalpinia sappan on the basis of their biological activities against three types of viral NAs. Of isolated homoisoflavonoids, sappanone A (2) showed the most potent NAs inhibitory activities with IC 50 values of 0.7 µM [H1N1], 1.1 µM [H3N2], and 1.0 µM [H9N2], respectively, whereas saturated homoisoflavonoid (3) did not show significantly inhibition. This result revealed that α,β-unsaturated carbonyl group in A-ring was the key requirements for viral NAs inhibitory activity. In our enzyme kinetic study, all NA inhibitors screened were found to be reversible noncompetitive types.

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confidence: 99%

Homoisoflavonoids from <i>Caesalpinia sappan</i> Displaying Viral Neuraminidases Inhibition

Jeong

Kim

et al. 2012

Biological & Pharmaceutical Bulletin

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“…Column chromatography was carried out using 230-400 mesh Silica Gel. Silica gel 1 H and 13 C NMR were obtained on a Bruker AM 500 ( 1 H NMR at 500 MHz, 13 C NMR at 125 MHz) spectrometer. Liquid chromatography-mass spectrometry (LC-MS) analyzes were performed using an LC-MS-UPLC-TQD (ESI and APCI) instrument.…”

Section: General Apparatus and Chemicalsmentioning

confidence: 99%

“…The structural characteristics of flavonoids from the root of Cudrania tricuspidata and Sophora flavescens required for neuraminidase inhibition has studied and compared with commercially available flavonoids [11,12]. Four coumarins has isolated from methanol extracts of Glycyrrhiza uralensis roots and they have neuraminidase inhibitory activity [13].…”

Section: Isolation Of Neuraminidase Inhibitors From Aqueous Extract Omentioning

confidence: 99%

Molecular Structure Studies of Neuraminidase Inhibitors from Eleusine Aegyptiaca L

K.Poonkuzhali¹,

V.Princy²,

T.Jebastin³

et al. 2017

International Journal of Medicinal Plants and Natural Products

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“…In the search we have selected chalcone, a phytoconstituent derived from roots of Glycyrrhiza, which have been reported to be active against H1N1-NA. However they show lesser NA inhibitory activity as compared to commercial drugs [6]. We have further developed this scaffold based on electronic and steric properties with substituents on benzylidene ring of chalcone moiety (1, 3-diphenyl-prop-3-ene-1-one) keeping 2'-Hydroxy group at phenyl moiety constant.…”

Section: Introductionmentioning

confidence: 99%

Virucidal Activity of Newly Synthesized Chalcone Derivatives against H1N1 Virus Supported by Molecular Docking and Membrane Interaction Studies

Pradip¹,

Khushboo²,

Devanshi³

et al. 2016

J Antivir Antiretrovir

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Oseltamivir and zanamivir are the commercially successful neuraminidase (NA) inhibitors approved for treatment of influenza, caused by highly pathogenic H1N1 influenza virus. Being transition state analogs of sialic acid, an endogenous ligand of NA, many scaffolds were developed based on similar structural features. But high rate of mutation in H1N1 necessitates extra search of a novel drug which can withstand drug resistance. Considering this we have developed a known naturally occurring scaffold chalcone, which is not a transition state analog, by incorporating various substituents based on their electronic and steric properties. With the help of computational drug design few promising molecules are screened and synthesized further. All the compounds under study showed different mode of binding in the active cavity. The inhibition of cytopathic effect of H1N1 by synthesized derivatives has been evaluated by in vitro cell based technique using oseltamivir as a standard. To gain insight into molecular mechanism of interaction of the derivatives with H1N1-NA, we have investigated the effect of these molecules on thermotropic properties and organization of membrane bilayer prepared from lipids using nuclear magnetic resonance (NMR) and differential scanning calorimetric (DSC) techniques. The compounds under study point towards stabilization of the membrane bilayer as expected for antiviral activity. Almost all derivatives showed activity parallel to the standard. Among all derivative ChmN showed highest activity at 0.67 nM whereas lowest activity was displayed by derivative ChmM at 10.35 nM. Derivative ChpH showed activity almost equivalent to oseltamivir.

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Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis

Cited by 88 publications

References 28 publications

Homoisoflavonoids from <i>Caesalpinia sappan</i> Displaying Viral Neuraminidases Inhibition

Homoisoflavonoids from <i>Caesalpinia sappan</i> Displaying Viral Neuraminidases Inhibition

Molecular Structure Studies of Neuraminidase Inhibitors from Eleusine Aegyptiaca L

Virucidal Activity of Newly Synthesized Chalcone Derivatives against H1N1 Virus Supported by Molecular Docking and Membrane Interaction Studies

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