title: (S)-2,3-dihydrofarnesoic acid, a new component in cephalic glands of male European beewolves Philanthus triangulum.
abstract: The chemical composition and functional significance of pheromones of solitary Hymenoptera is much less well known compared to social species. Males of the genus Philanthus (Sphecidae) are territorial and scent mark their territories to attract females. Because of inconsistent results of earlier studies, we reanalyzed the content of the cephalic glands of male European beewolves, Philanthus triangulum F. Besides a variety of alkanes and alkenes, four major compounds were found. Two of these, (Z)-11-eicosen-1-ol and (Z)-10-nonadecen-2-one, had been previously described as constituents of the cephalic glands. We identified 1-octadecanol as a new component of the cephalic gland, and a fourth compound, enantiopure (S)-2,3-dihydrofamesoic acid, was identified for the first time in nature. Structural elucidation and enantiomeric analysis were performed by HRGC-MS and HRGC-FTIR as well as enantioselective gas chromatography and by means of authentic reference compounds. Occurrence and function of the four compounds in insect chemistry are discussed.
authors.affiliation: Theodor-Boveri-Institut für Biowissenschaften, Zoologie III, Biozentrum, Am Hubland, D-97074 Würzburg, G ermany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Schmitt
authors.forename: Erhard
authors.initials: E
authors.lastname: Strohm
authors.forename: Gudrun
authors.initials: G
authors.lastname: Herzner
authors.forename: Carlo
authors.initials: C
authors.lastname: Bicchi
authors.forename: Gerhard
authors.initials: G
authors.lastname: Krammer
authors.forename: Frank
authors.initials: F
authors.lastname: Heckel
authors.forename: Peter
authors.initials: P
authors.lastname: Schreier
mesh_terms: D000818:Animals; D005088:Exocrine Glands / Q000737:chemistry*; D005231:Fatty Acids, Unsaturated / Q000737:chemistry* / Q000302:isolation & purification; D008401:Gas Chromatography-Mass Spectrometry; D006927:Hymenoptera / Q000502:physiology*; D008297:Male; D010675:Pheromones / Q000737:chemistry* / Q000302:isolation & purification*; D017550:Spectroscopy, Fourier Transform Infrared
chemical_list: C482760:(S)-2,3-dihydrofarnesoic acid; D005231:Fatty Acids, Unsaturated; D010675:Pheromones