title: Epimerisation of chiral hydroxylactones by short-chain dehydrogenases/reductases accounts for sex pheromone evolution in Nasonia.
abstract: Males of all species of the parasitic wasp genus Nasonia use (4R,5S)-5-hydroxy-4-decanolide (RS) as component of their sex pheromone while only N. vitripennis (Nv), employs additionally (4R,5R)-5-hydroxy-4-decanolide (RR). Three genes coding for the NAD+-dependent short-chain dehydrogenases/reductases (SDRs) NV10127, NV10128, and NV10129 are linked to the ability of Nv to produce RR. Here we show by assaying recombinant enzymes that SDRs from both Nv and N. giraulti (Ng), the latter a species with only RS in the pheromone, epimerise RS into RR and vice versa with (4R)-5-oxo-4-decanolide as an intermediate. Nv-derived SDR orthologues generally had higher epimerisation rates, which were also influenced by NAD+availability. Semiquantitative protein analyses of the pheromone glands by tandem mass spectrometry revealed that NV10127 as well as NV10128 and/or NV10129 were more abundant in Nv compared to Ng. We conclude that the interplay of differential expression patterns and SDR epimerisation rates on the ancestral pheromone component RS accounts for the evolution of a novel pheromone phenotype in Nv.
authors.affiliation: Institute of Zoology, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Joachim
authors.initials: J
authors.lastname: Ruther
authors.affiliation: Department of Biology, Lund University, SE-22362 Lund, Sweden.
authors.forename: Åsa K
authors.initials: ÅK
authors.lastname: Hagström
authors.affiliation: Institute of Zoology, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Birgit
authors.initials: B
authors.lastname: Brandstetter
authors.affiliation: Department of Chemistry, Kenyon College, Gambier, OH 43022, USA.
authors.forename: John
authors.initials: J
authors.lastname: Hofferberth
authors.affiliation: Institute of Biochemistry, Genetics and Microbiology, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Astrid
authors.initials: A
authors.lastname: Bruckmann
authors.affiliation: Institute of Biophysics and Physical Biochemistry, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Florian
authors.initials: F
authors.lastname: Semmelmann
authors.affiliation: Institute of Zoology, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Michaela
authors.initials: M
authors.lastname: Fink
authors.affiliation: Institute of Zoology, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Helena
authors.initials: H
authors.lastname: Lowack
authors.affiliation: Institute of Biophysics and Physical Biochemistry, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Sabine
authors.initials: S
authors.lastname: Laberer
authors.affiliation: Centre for Molecular Biodiversity Research, Zoological Research Museum Alexander Koenig, 53113 Bonn, Germany.
authors.forename: Oliver
authors.initials: O
authors.lastname: Niehuis
authors.affiliation: Institute of Biochemistry, Genetics and Microbiology, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Rainer
authors.initials: R
authors.lastname: Deutzmann
authors.affiliation: Department of Biology, Lund University, SE-22362 Lund, Sweden.
authors.forename: Christer
authors.initials: C
authors.lastname: Löfstedt
authors.affiliation: Institute of Biophysics and Physical Biochemistry, University of Regensburg, 93053 Regensburg, Germany.
authors.forename: Reinhard
authors.initials: R
authors.lastname: Sterner
mesh_terms: D000818:Animals; D019143:Evolution, Molecular; D019476:Insect Proteins / Q000235:genetics / Q000378:metabolism; D007783:Lactones / Q000737:chemistry*; D008297:Male; D010088:Oxidoreductases / Q000235:genetics* / Q000378:metabolism; D010675:Pheromones / Q000737:chemistry / Q000378:metabolism*; D011994:Recombinant Proteins / Q000378:metabolism; D012726:Sexual Behavior, Animal; D053719:Tandem Mass Spectrometry; D014863:Wasps / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*
chemical_list: C541356:5-hydroxy-4-decanolide; D019476:Insect Proteins; D007783:Lactones; D010675:Pheromones; D011994:Recombinant Proteins; D010088:Oxidoreductases