Biosynthesis of fucoxanthin and diadinoxanthin and function of initial pathway genes in Phaeodactylum tricornutum

J Exp Bot. 2012 Sep;63(15):5607-12. doi: 10.1093/jxb/ers211. Epub 2012 Aug 9.

Abstract

The biosynthesis pathway to diadinoxanthin and fucoxanthin was elucidated in Phaeodactylum tricornutum by a combined approach involving metabolite analysis identification of gene function. For the initial steps leading to β-carotene, putative genes were selected from the genomic database and the function of several of them identified by genetic pathway complementation in Escherichia coli. They included genes encoding a phytoene synthase, a phytoene desaturase, a ζ-carotene desaturase, and a lycopene β-cyclase. Intermediates of the pathway beyond β-carotene, present in trace amounts, were separated by TLC and identified as violaxanthin and neoxanthin in the enriched fraction. Neoxanthin is a branching point for the synthesis of both diadinoxanthin and fucoxanthin and the mechanisms for their formation were proposed. A single isomerization of one of the allenic double bounds in neoxanthin yields diadinoxanhin. Two reactions, hydroxylation at C8 in combination with a keto-enol tautomerization and acetylation of the 3'-HO group results in the formation of fucoxanthin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biosynthetic Pathways
  • Carotenoids / chemistry
  • Carotenoids / metabolism
  • Diatoms / chemistry
  • Diatoms / enzymology
  • Diatoms / genetics*
  • Escherichia coli / genetics
  • Escherichia coli / metabolism
  • Genetic Complementation Test
  • Geranylgeranyl-Diphosphate Geranylgeranyltransferase / genetics
  • Geranylgeranyl-Diphosphate Geranylgeranyltransferase / metabolism
  • Intramolecular Lyases / genetics*
  • Intramolecular Lyases / metabolism
  • Oxidoreductases / genetics*
  • Oxidoreductases / metabolism
  • Phylogeny
  • Xanthophylls / biosynthesis*
  • Xanthophylls / chemistry
  • Xanthophylls / isolation & purification
  • Xanthophylls / metabolism
  • beta Carotene / chemistry
  • beta Carotene / metabolism
  • zeta Carotene / chemistry
  • zeta Carotene / metabolism

Substances

  • Xanthophylls
  • zeta Carotene
  • beta Carotene
  • fucoxanthin
  • diadinoxanthin
  • Carotenoids
  • violaxanthin
  • (all-E) phytoene
  • Oxidoreductases
  • phytoene dehydrogenase
  • zeta-carotene desaturase
  • Geranylgeranyl-Diphosphate Geranylgeranyltransferase
  • Intramolecular Lyases
  • lycopene cyclase-isomerase
  • neoxanthin