Verticipyrone, a new NADH-fumarate reductase inhibitor, produced by Verticillium sp. FKI-1083

J Antibiot (Tokyo). 2006 Dec;59(12):785-90. doi: 10.1038/ja.2006.103.

Abstract

A new NADH-fumarate reductase inhibitor, verticipyrone, was isolated from the cultured broth of a fungus, Verticillium sp. FKI-1083. The structure was established as (E)-2-methoxy-3,5-dimethyl-6-(3-methyl-2-undecenyl)-4H-pyran-4-one. Verticipyrone exhibited an IC50 value of 0.88 nM against NADH-fumarate reductase of Ascaris suum. Verticipyrone inhibited both Ascaris and bovine heart complex I, and its synthetic analogue, 8,9-dihydro-8-hydroxyverticipyrone, showed good selectivity against Ascaris complex I.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Alkenes / isolation & purification*
  • Alkenes / pharmacology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Fermentation
  • Magnetic Resonance Spectroscopy
  • Oxidoreductases Acting on CH-CH Group Donors / antagonists & inhibitors*
  • Pyrones / chemistry
  • Pyrones / isolation & purification*
  • Pyrones / pharmacology
  • Verticillium / metabolism*

Substances

  • Alkenes
  • Enzyme Inhibitors
  • Pyrones
  • verticipyrone
  • Oxidoreductases Acting on CH-CH Group Donors
  • fumarate reductase (NADH)