Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers

Arch Biochem Biophys. 1988 May 15;263(1):191-8. doi: 10.1016/0003-9861(88)90627-3.

Abstract

A microsome preparation from elicitor-challenged soybean cell suspension cultures catalyzed an NADPH-dependent and oxygen-dependent cyclization of a mixture of 2- and 4-dimethylallylglycinols to the glyceollin isomers I-III. This is the last committed step in glyceollin biosynthesis. The cyclase was inhibited in a light-reversible manner by carbon monoxide in the presence of oxygen. Cyclase was also inhibited by cytochrome c, NADP+, and a number of inhibitors of cytochrome P-450 enzymes. NADH in the presence of low concentrations of NADPH had a synergistic effect. On a Percoll gradient, the position of cyclase coincided with marker enzymes for the endoplasmic reticulum. These properties identify the cyclase as a cytochrome P-450-dependent monooxygenase. Unstimulated soybean cell culture did not contain detectable cyclase activity. Challenge with either a glucan elicitor from Phytophthora megasperma f.sp. glycinea or with yeast extract caused strong stimulation of cyclase activity with a maximum at about 24 h after elicitor addition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / metabolism*
  • Cells, Cultured
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Dimethylallyltranstransferase / metabolism
  • Isomerism
  • Microsomes / enzymology
  • NADP / metabolism
  • Oxygen / metabolism
  • Phytoalexins
  • Plant Extracts / biosynthesis*
  • Plant Extracts / metabolism
  • Plants / enzymology*
  • Pterocarpans*
  • Sesquiterpenes
  • Terpenes

Substances

  • Benzopyrans
  • Plant Extracts
  • Pterocarpans
  • Sesquiterpenes
  • Terpenes
  • NADP
  • glyceollin
  • 3,6,9-trihydroxypterocarpan
  • Dimethylallyltranstransferase
  • Oxygen
  • Phytoalexins