Two cytochromes P450 catalyze S-heterocyclizations in cabbage phytoalexin biosynthesis

Nat Chem Biol. 2015 Nov;11(11):837-9. doi: 10.1038/nchembio.1914. Epub 2015 Sep 21.

Abstract

Phytoalexins are abundant in edible crucifers and have important biological activities, yet no dedicated gene for their biosynthesis is known. Here, we report two new cytochromes P450 from Brassica rapa (Chinese cabbage) that catalyze unprecedented S-heterocyclizations in cyclobrassinin and spirobrassinin biosynthesis. Our results provide genetic and biochemical insights into the biosynthesis of a prominent pair of dietary metabolites and have implications for pathway discovery across >20 recently sequenced crucifers.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Base Sequence
  • Biocatalysis
  • Brassica rapa / enzymology*
  • Brassica rapa / genetics
  • Brassicaceae / enzymology*
  • Brassicaceae / genetics
  • Cyclization
  • Cytochrome P-450 Enzyme System / chemistry
  • Cytochrome P-450 Enzyme System / genetics
  • Cytochrome P-450 Enzyme System / metabolism*
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Gene Expression
  • High-Throughput Nucleotide Sequencing
  • Indoles / chemistry
  • Indoles / metabolism*
  • Isoenzymes / chemistry
  • Isoenzymes / genetics
  • Isoenzymes / metabolism
  • Kinetics
  • Microsomes / chemistry
  • Microsomes / metabolism
  • Molecular Sequence Data
  • Phytoalexins
  • Plant Leaves / chemistry
  • Plant Leaves / metabolism
  • Plant Proteins / chemistry
  • Plant Proteins / genetics
  • Plant Proteins / metabolism*
  • RNA, Messenger / genetics
  • RNA, Messenger / metabolism
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / genetics
  • Recombinant Proteins / metabolism
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / metabolism*
  • Spiro Compounds / chemistry
  • Spiro Compounds / metabolism*
  • Thiazoles / chemistry
  • Thiazoles / metabolism*
  • Thiocarbamates / chemistry
  • Thiocarbamates / metabolism*
  • Vegetables / chemistry
  • Vegetables / metabolism

Substances

  • Indoles
  • Isoenzymes
  • Plant Proteins
  • RNA, Messenger
  • Recombinant Proteins
  • Sesquiterpenes
  • Spiro Compounds
  • Thiazoles
  • Thiocarbamates
  • cyclobrassinin
  • spirobrassinin
  • Cytochrome P-450 Enzyme System
  • Phytoalexins

Associated data

  • GENBANK/BK009360
  • GENBANK/BK009361
  • GENBANK/BK009362
  • GENBANK/BK009363
  • GENBANK/BK009364
  • GENBANK/BK009365
  • GENBANK/BK009366
  • GENBANK/BK009367
  • GENBANK/BK009368
  • GENBANK/BK009369
  • GENBANK/BK009370
  • GENBANK/BK009371
  • GENBANK/BK009372
  • GENBANK/BK009373
  • GENBANK/BK009374
  • GENBANK/BK009375
  • GEO/GSE69785