Prenylated and benzylated flavonoids from the fruits of Cudrania tricuspidata

J Nat Prod. 2009 Jan;72(1):164-7. doi: 10.1021/np800418j.

Abstract

Three new prenylated isoflavones, 5,7-dihydroxy-6-(2''-hydroxy-3''-methylbut-3''-enyl)-4'-methoxylisoflavone (1), 5,4'-dihydroxy-6-(3''-methylbut-2''-enyl)-2'''-(4'''-hydroxy-4'''-methylethyl)-3'''-methoxydihydrofurano-[4''',5''';7,8]isoflavone (2), and 5,4'-dihydroxy-8-(3''-methylbut-2''-enyl)-2'''-(4'''-hydroxy-4'''-methylethyl)furano-[4''',5''';6,7]isoflavone (3), a benzylated dihydroflavonol, 5,7,4'-trihydroxy-8-p-hydroxybenzyldihydroflavonol (4), and eight known flavonoids (5-12) were isolated from the fruits of Cudrania tricuspidata. The structures of these compounds were determined on the basis of MS and (1)H and (13)C NMR spectroscopic data, including 2D NMR experiments. Compounds 2, 3, 6, 7, 8, 10, 11, and 12 inhibited LPS-induced nitric oxide production, with IC(50) values of 11.8-41.8 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry
  • Benzene Derivatives / isolation & purification*
  • Benzene Derivatives / pharmacology
  • Fruit / chemistry
  • Inhibitory Concentration 50
  • Isoflavones / chemistry
  • Isoflavones / isolation & purification*
  • Isoflavones / pharmacology
  • Lipopolysaccharides / pharmacology
  • Molecular Structure
  • Moraceae / chemistry*
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide / metabolism
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*

Substances

  • Benzene Derivatives
  • Isoflavones
  • Lipopolysaccharides
  • Nitric Oxide