C-Methylated Flavonoid Glycosides from Pentarhizidium orientale Rhizomes and Their Inhibitory Effects on the H1N1 Influenza Virus

J Nat Prod. 2017 Oct 27;80(10):2818-2824. doi: 10.1021/acs.jnatprod.7b00677. Epub 2017 Oct 6.

Abstract

Thirteen C-methylated flavonoid glycosides (1-13), along with 15 previously known flavonoids (14-28), were isolated from rhizomes of Pentarhizidium orientale. Among these compounds, matteuorienates D-K (1-8) were obtained as analogues of matteuorienates A-C (14-16), which contain a characteristic 3-hydroxy-3-methylglutaryl (HMG) moiety. The structures of 1-13 were characterized by spectroscopic analysis and chemical derivatization. The isolates were evaluated for their antiviral activities against influenza virus (H1N1), with compounds 21, 22, 23, 25, and 26 showing inhibitory effects (IC50 of 23.9-30.3 μM) against neuraminidases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemistry
  • Dogs
  • Flavonoids / chemistry
  • Flavonoids / isolation & purification*
  • Flavonoids / pharmacology*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Influenza A Virus, H1N1 Subtype / drug effects*
  • Inhibitory Concentration 50
  • Madin Darby Canine Kidney Cells
  • Molecular Structure
  • Monosaccharides
  • Neuraminidase / antagonists & inhibitors
  • Rhizome / chemistry*

Substances

  • Antiviral Agents
  • C-glycoside
  • Flavonoids
  • Glycosides
  • Monosaccharides
  • Neuraminidase