title: Sex pheromone of the pine sawfly, Gilpinia pallida: chemical identification, synthesis, and biological activity.
abstract: We present the identification of the sex pheromone in the pine sawfly, Gilpinia pallida, including analysis of the female pheromone content, male antennal response and attraction in the field, and synthesis of the most active pheromone component. Several 3,7-dimethyl-2-alkanols were identified from female whole-body extracts, including some compounds with a 2R configuration. This is the first observation of such compounds in a pine sawfly species. Antennae of male G. pallida responded strongly in electroantennograph (EAG) recordings to the (2S,3R,7R)-isomers of the propionates of 3,7-dimethyl-2-tridecanol, 3,7-dimethyl-2-tetradecanol, and 3,7-dimethyl-2-pentadecanol, as well as to the acetates of the tri- and pentadecanols (the acetate of the tetradecanol was not tested). The propionate of (2S,3R,7R)-3,7-dimethyl-2-tetradecanol caught more males in the field than the corresponding isomer of tri- or pentadecanol. We suggest that the (2S,3R,7R)-isomer of 3,7-dimethyl-2-tetradecanol is likely the main sex pheromone precursor in G. pallida, with a subsidiary role for the (2S,3R,7R)-isomer of the tridecanol. Preparation of highly pure (2R,3R,7R)- and (2S,3R,7R)-stereoisomers of 3,7-dimethyl-2-tetradecanol, including the biological active esters, was performed via chemoenzymatic methods and is described in detail.
authors.affiliation: Department of Natural Sciences, Mid Sweden University, 85170, Sundsvall, Sweden. erik.hedenstrom@miun.se
authors.forename: Erik
authors.initials: E
authors.lastname: Hedenström
authors.forename: Helene
authors.initials: H
authors.lastname: Edlund
authors.forename: Ann-Britt
authors.initials: AB
authors.lastname: Wassgren
authors.forename: Gunnar
authors.initials: G
authors.lastname: Bergström
authors.forename: Olle
authors.initials: O
authors.lastname: Anderbrant
authors.forename: Fredrik
authors.initials: F
authors.lastname: Ostrand
authors.forename: Andrzej
authors.initials: A
authors.lastname: Sierpinski
authors.forename: Marie-Anne
authors.initials: MA
authors.lastname: Auger-Rozenberg
authors.forename: Annette
authors.initials: A
authors.lastname: Herz
authors.forename: Werner
authors.initials: W
authors.lastname: Heitland
authors.forename: Martti
authors.initials: M
authors.lastname: Varama
mesh_terms: D000818:Animals; D004594:Electrophysiology; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006927:Hymenoptera / Q000378:metabolism* / Q000502:physiology; D008297:Male; D012724:Sex Attractants / Q000138:chemical synthesis / Q000378:metabolism* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
chemical_list: D012724:Sex Attractants