Cytochrome P450 Monooxygenases of DIBOA Biosynthesis: Specificity and Conservation Among Grasses

Phytochemistry. 1999 Mar;50(6):925-30. doi: 10.1016/s0031-9422(98)00318-5.

Abstract

DIBOA and DIMBOA are secondary metabolites of grasses which function as natural pesticides. The four maize genes BX2 through BX5 encode cytochrome P450-dependent monooxygenases that catalyse four consecutive reactions in the biosynthesis of these secondary products. Although BX2-BX5 share significant sequence homology, the four enzymes have evolved into specific enzymes each catalysing predominantly only one reaction in the pathway. In addition to these natural reactions, BX3 hydroxylates 1,4-benzoxazin-3-one and BX2 shows pCMA demethylase activity. With respect to DIBOA biosynthesis, identical enzymatic reactions have been found in rye as compared to maize, indicating early evolution of the P450 enzymes in the grasses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoxazines
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism*
  • DNA, Complementary / genetics
  • Edible Grain / enzymology
  • Edible Grain / genetics
  • Edible Grain / metabolism*
  • Hordeum / enzymology
  • Hordeum / genetics
  • Hordeum / metabolism
  • Isoenzymes / genetics
  • Isoenzymes / metabolism
  • Kinetics
  • Oxazines / metabolism*
  • Saccharomyces cerevisiae / enzymology
  • Saccharomyces cerevisiae / genetics
  • Secale
  • Substrate Specificity
  • Zea mays / enzymology
  • Zea mays / genetics
  • Zea mays / metabolism

Substances

  • Benzoxazines
  • DNA, Complementary
  • Isoenzymes
  • Oxazines
  • 2,4-dihydroxy-1,4-benzoxazin-3-one
  • Cytochrome P-450 Enzyme System