4.7 Article

Mumefural and related HMF derivatives from Japanese apricot fruit juice concentrate show multiple inhibitory effects on pandemic influenza A (H1N1) virus

Journal

FOOD CHEMISTRY
Volume 127, Issue 1, Pages 1-9

Publisher

ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2010.12.031

Keywords

Pancemic; Influenza; Japanese apricot; Fruit-juice concentrate; Mumefural; Hemagglutination; Sialidase

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology [20390028]
  2. Ministry of Health, Labor and Welfare, Japan
  3. Grants-in-Aid for Scientific Research [20390028] Funding Source: KAKEN

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Fruit-juice concentrate of Japanese apricot (Prunus mume Sieb. et Zucc.) has been shown to be effective against influenza A infection in MOCK cells. In this study, we isolated five components from the fruit-juice concentrate of Japanese apricot, 5-(hydroxymethyl)-2-formylfuran (HMF), 1-[5-(2-formylfuryl)methyl]dihydrogen 2-hydroxypropane-1,2,3-tricarboxylate (mumefural, MF), 2-[5-(2-formylfuryl)methyl]dihydrogen 2-hydroxypropane-1,2,3-tricarboxylate (MF), 1-[5-(2-formylfuryl)methyl]hydrogen 1-hydroxyethane-1,2-dicarboxylate (MM) and 2-[5-(2-formylfuryl)methyl]hydrogen 1-hydroxyethane-1, 2-dicarboxylate (MA2), and investigated their inhibitory activities against the novel influenza A/Narita/1/2009 (H1N1) pandemic virus hemagglutinin and neuraminidase functions, which are essential for viral attachment and budding, respectively. An hemagglutination inhibition assay indicated that MF and MF were effective at minimum hemagglutination concentrations of 3.1 and 6.3 mM, respectively. An inhibition study for sialidase activity of the neuraminidase spike showed that MF was the most active anti-sialidase compound with an IC50 value of 0.21 +/- 0.01 mM, followed by MA2 (IC50, 0.71 +/- 0.09 mM), MA1 (IC50, 1.64 +/- 0.31 mM) and MF(IC50, 1.62 +/- 0.22 mM). Furthermore. MF was shown to inhibit the growth of the pandemic virus in a dose-dependent manner (62 +/- 3% inhibition at 5 mM). The results suggest that MF, a citric acid ester linked to HMF at the 1-position of the propane backbone, might be a lead compound for the development of anti-influenza A inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

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