title: Oleic acid is a precursor of linoleic acid and the male sex pheromone in Nasonia vitripennis.
abstract: Linoleic acid (C18:2(Δ9,12), LA) is crucial for many cell functions in organisms. It has long been a paradigm that animals are unable to synthesize LA from oleic acid (C18:1(Δ9), OA) because they were thought to miss Δ(12)-desaturases for inserting a double bound at the Δ(12)-position. Today it is clear that this is not true for all animals because some insects and other invertebrates have been demonstrated to synthesize LA. However, the ability to synthesize LA is known in only five insect orders and no examples have been reported so far in the Hymenoptera. LA plays a particular role in the parasitic wasp Nasonia vitripennis, because it is the precursor of the male sex pheromone consisting of (4R,5R)- and (4R,5S)-5-hydroxy-4-decanolides. Here we demonstrate by stable isotope labeling that N. vitripennis is able to incorporate externally applied fully (13)C-labeled OA into the male sex pheromone suggesting that they convert initially OA into LA. To verify this assumption, we produced fly hosts (Lucilia caesar) which were experimentally enriched in (13)C-labeled OA and reared male parasitoids on these hosts. Chemical analysis of transesterified lipid raw extracts from hosts and parasitoids revealed that N. vitripennis but not L. caesar contained (13)C-labeled LA methyl ester. Furthermore, male wasps from the manipulated hosts produced significant amounts of (13)C-labeled sex pheromone. These results suggest that N. vitripennis possesses a Δ(12)-desaturase. The additional fitness relevant function as pheromone precursor might have favored the evolution of LA biosynthesis in N. vitripennis to make the wasps independent of the formerly essential nutrient.
authors.affiliation: University of Regensburg, Institute of Zoology, Universitätsstraße 31, 93053 Regensburg, Germany. Electronic address: birgit.blaul@gmx.de.
authors.forename: Birgit
authors.initials: B
authors.lastname: Blaul
authors.affiliation: University of Regensburg, Institute of Biochemistry, Genetic & Microbiology, Universitätsstraße 31, 93053 Regensburg, Germany. Electronic address: robert-steinbauer@gmx.de.
authors.forename: Robert
authors.initials: R
authors.lastname: Steinbauer
authors.affiliation: University of Regensburg, Institute of Biochemistry, Genetic & Microbiology, Universitätsstraße 31, 93053 Regensburg, Germany. Electronic address: philipp.merkl@ur.de.
authors.forename: Philipp
authors.initials: P
authors.lastname: Merkl
authors.affiliation: University of Regensburg, Institute of Biophysics & Physical Biochemistry, Universitätsstraße 31, 93053 Regensburg, Germany. Electronic address: rainer.merkl@ur.de.
authors.forename: Rainer
authors.initials: R
authors.lastname: Merkl
authors.affiliation: University of Regensburg, Institute of Biochemistry, Genetic & Microbiology, Universitätsstraße 31, 93053 Regensburg, Germany. Electronic address: herbert.tschochner@ur.de.
authors.forename: Herbert
authors.initials: H
authors.lastname: Tschochner
authors.affiliation: University of Regensburg, Institute of Zoology, Universitätsstraße 31, 93053 Regensburg, Germany. Electronic address: joachim.ruther@ur.de.
authors.forename: Joachim
authors.initials: J
authors.lastname: Ruther
mesh_terms: D000818:Animals; D004175:Diptera / Q000469:parasitology; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D019787:Linoleic Acid / Q000096:biosynthesis* / Q000737:chemistry; D008297:Male; D019301:Oleic Acid / Q000378:metabolism; D010675:Pheromones / Q000096:biosynthesis* / Q000737:chemistry; D011679:Pupa; D012724:Sex Attractants / Q000096:biosynthesis* / Q000737:chemistry; D014863:Wasps / Q000378:metabolism*
chemical_list: C541356:5-hydroxy-4-decanolide; D007783:Lactones; D010675:Pheromones; D012724:Sex Attractants; D019301:Oleic Acid; D019787:Linoleic Acid
keywords: Biosynthesis; Delta-12-desaturase; Linoleic acid; Nasonia; Oleic acid; Sex pheromone