Identification of fungal sphingolipid C9-methyltransferases by phylogenetic profiling

J Biol Chem. 2006 Mar 3;281(9):5582-92. doi: 10.1074/jbc.M512864200. Epub 2005 Dec 8.

Abstract

Fungal glucosylceramides play an important role in plant-pathogen interactions enabling plants to recognize the fungal attack and initiate specific defense responses. A prime structural feature distinguishing fungal glucosylceramides from those of plants and animals is a methyl group at the C9-position of the sphingoid base, the biosynthesis of which has never been investigated. Using information on the presence or absence of C9-methylated glucosylceramides in different fungal species, we developed a bioinformatics strategy to identify the gene responsible for the biosynthesis of this C9-methyl group. This phylogenetic profiling allowed the selection of a single candidate out of 24-71 methyltransferase sequences present in each of the fungal species with C9-methylated glucosylceramides. A Pichia pastoris knock-out strain lacking the candidate sphingolipid C9-methyltransferase was generated, and indeed, this strain contained only non-methylated glucosylceramides. In a complementary approach, a Saccharomyces cerevisiae strain was engineered to produce glucosylceramides suitable as a substrate for C9-methylation. C9-methylated sphingolipids were detected in this strain expressing the candidate from P. pastoris, demonstrating its function as a sphingolipid C9-methyltransferase. The enzyme belongs to the superfamily of S-adenosylmethionine-(SAM)-dependent methyltransferases and shows highest sequence similarity to plant and bacterial cyclopropane fatty acid synthases. An in vitro assay showed that sphingolipid C9-methylation is membrane-bound and requires SAM and Delta4,8-desaturated ceramide as substrates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Computational Biology
  • Fungal Proteins / classification*
  • Fungal Proteins / genetics
  • Fungal Proteins / metabolism*
  • Glucosylceramides* / chemistry
  • Glucosylceramides* / metabolism
  • Methyltransferases / classification*
  • Methyltransferases / genetics
  • Methyltransferases / metabolism*
  • Molecular Sequence Data
  • Molecular Structure
  • Phylogeny
  • Pichia / enzymology
  • Pichia / genetics
  • Sequence Alignment
  • Sphingolipids* / chemistry
  • Sphingolipids* / metabolism

Substances

  • Fungal Proteins
  • Glucosylceramides
  • Sphingolipids
  • Methyltransferases
  • cyclopropane synthetase

Associated data

  • GENBANK/AAU10084
  • GENBANK/AAU10085
  • GENBANK/AAZ08581
  • GENBANK/AY700777
  • GENBANK/AY700778
  • GENBANK/DQ070247
  • PDB/2FAY