A new photosystem II electron transfer inhibitor from Sorghum bicolor

J Nat Prod. 1998 Jul;61(7):927-30. doi: 10.1021/np9800708.

Abstract

Our study of the mechanism(s) by which sorgoleone (1) acts as a photosystem II (PS II) inhibitor led to the isolation of a new benzoquinone derivative, 2-hydroxy-5-ethoxy-3-[(Z,Z)-8',11', 14'-pentadecatriene]-rho-benzoquinone (2), from the root exudate of sorghum. The structure of 2, which is being given the name 5-ethoxy-sorgoleone, was determined by spectroscopic means. A methoxy derivative (3) of 1 was also prepared. Both 2 and 3 caused a reduction in oxygen evolution by thylakoid membranes and induced variable chlorophyll fluorescence. These compounds, however, were less active inhibitors of PS II than 1.

MeSH terms

  • Benzoquinones / chemistry
  • Benzoquinones / isolation & purification*
  • Benzoquinones / toxicity
  • Carbohydrate Sequence
  • Chlorophyll / metabolism
  • Electron Transport / drug effects*
  • Herbicides / chemistry
  • Herbicides / isolation & purification*
  • Herbicides / toxicity
  • Lipids*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Sequence Data
  • Oxygen / metabolism
  • Photosynthesis / drug effects*
  • Plants, Medicinal / chemistry*
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Spinacia oleracea / metabolism

Substances

  • Benzoquinones
  • Herbicides
  • Lipids
  • sorgoleone
  • Chlorophyll
  • Oxygen