Identification of a novel casbane-type diterpene phytoalexin, ent-10-oxodepressin, from rice leaves

Biosci Biotechnol Biochem. 2013;77(4):760-5. doi: 10.1271/bbb.120891. Epub 2013 Apr 7.

Abstract

A 70% methanol extract of UV-irradiated rice leaves (400 g) was separated by chromatographic methods to give UV-induced compound 1 (2.1 mg) which showed a possible molecular ion at m/z 300 in the GC/MS analysis. Its structure was determined by NMR and MS methods. The 1H- and 13C-NMR spectra of 1 were identical to those of 10-oxodepressin (2), a casbane-type diterpene derived from the soft coral, Sinularia depressa. The specific rotation of 1 was positive, whereas that of 2 was negative. We therefore established 1 as ent-10-oxodepressin. The accumulation of 1 was also induced by an inoculation of the rice blast fungus. Compound 1 inhibited spore germination (IC50 30 ppm) and germ tube growth (IC50 10 ppm) of the rice blast fungus. We thus concluded that 1 was a novel rice phytoalexin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / analysis*
  • Antifungal Agents / chemistry
  • Antifungal Agents / metabolism
  • Antifungal Agents / pharmacology
  • Diterpenes / analysis*
  • Diterpenes / chemistry
  • Diterpenes / metabolism
  • Diterpenes / pharmacology
  • Magnaporthe / drug effects
  • Magnaporthe / physiology
  • Oryza / chemistry*
  • Oryza / metabolism
  • Oryza / microbiology
  • Oryza / radiation effects
  • Phytoalexins
  • Plant Leaves / chemistry*
  • Plant Leaves / metabolism
  • Plant Leaves / microbiology
  • Plant Leaves / radiation effects
  • Sesquiterpenes / analysis*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / metabolism
  • Sesquiterpenes / pharmacology
  • Ultraviolet Rays

Substances

  • Antifungal Agents
  • Diterpenes
  • Sesquiterpenes
  • ent-10-oxodepressin
  • Phytoalexins