Novel apocarotenoid intermediates in Neurospora crassa mutants imply a new biosynthetic reaction sequence leading to neurosporaxanthin formation

Alejandro F. Estrada, Dominic Maier, Daniel Scherzinger, Javier Avalos, Salim Al-Babili*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

Neurosporaxanthin, β-apo-4′-carotenoic acid (C35), represents the end-product of the carotenoid pathway in Neurospora crassa. It is supposed to be synthesized in three steps catalyzed by sequential AL-2, CAO-2 and YLO-1 activities: (i) cyclization of 3,4-didehydrolycopene (C40); (ii) cleavage of torulene into β-apo-4′-carotenal (C35); and finally (iii) oxidation of β-apo-4′-carotenal. However, analyses of the ylo-1 mutant revealed the accumulation of intermediates other than β-apo-4′-carotenal. Here, we generated a 3,4-didehydrolycopene accumulating Escherichia coli strain and showed that CAO-2 cleaves this acyclic carotene in vivo and in vitro yielding apo-4′-lycopenal. The apocarotenoids accumulated in the ylo-1 mutant were then identified as apo-4′-lycopenal and apo-4′-lycopenol, pointing to the former as the YLO-1 substrate and indicating that cyclization is the last step in neurosporaxanthin biosynthesis. This was further substantiated by analyses of a cyclase-deficient al-2 mutant, revealing the accumulation of apo-4′-lycopenoic acid. The three acyclic apocarotenoids presented here have not been found naturally before.

Original languageEnglish (US)
Pages (from-to)1497-1505
Number of pages9
JournalFungal Genetics and Biology
Volume45
Issue number11
DOIs
StatePublished - Nov 1 2008

Keywords

  • Apocarotenoids
  • Carotenoid biosynthesis
  • Carotenoid cleavage
  • Fungi
  • Neurospora crassa
  • Neurosporaxanthin

ASJC Scopus subject areas

  • Microbiology
  • Genetics

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