title: The sex pheromones of two pine sawfly species, Gilpinia frutetorum and Gilpinia socia: chemical identification, synthesis and biological activity.
abstract: 3,7-Dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were identified in female whole body extracts from the two pine sawfly species Gilpinia frutetorum and Gilpinia socia. This is the first observation of 3-methylpentadecan-2-ol in extracts of a female pine sawfly species. Synthetic and highly pure stereoisomers of 3,7-dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were used to verify that the (2S,3R,7R)-isomer of 3,7-dimethylpentadecan-2-ol and (2S,3R)-3-methylpentadecan-2-ol were present in the extracts. The four stereoisomers of 3-methylpentadecan-2-ol and their biologically active esters were produced via chemoenzymatic methods and the synthesis is described in detail. Male G. socia antennae responded strongly in EAG recordings to the (2S,3R)-isomer of the acetate and propionate of 3-methylpentadecan-2-ol. Male antennae of both G. frutetorum and G. socia also responded to the (2S,3R,7R)- and (2S,3R,7S)-acetates of 3,7-dimethylpentadecan-2-ol.
authors: Department of Natural Sciences, Technology and Mathematics, Mid Sweden University, SE-851 70 Sundsvall, Sweden. erik.hedenstrom@miun.se
authors: Erik
authors: E
authors: Hedenström
authors: Helene
authors: H
authors: Edlund
authors: Ann-Britt
authors: AB
authors: Wassgren
authors: Gunnar
authors: G
authors: Bergström
authors: Olle
authors: O
authors: Anderbrant
authors: Fredrik
authors: F
authors: Ostrand
authors: Andrzej
authors: A
authors: Sierpinski
authors: Marie-Anne
authors: MA
authors: Auger-Rozenberg
authors: Annette
authors: A
authors: Herz
authors: Werner
authors: W
authors: Heitland
authors: Martti
authors: M
authors: Varama
mesh_terms: D000818:Animals; D002849:Chromatography, Gas; D005260:Female; D006927:Hymenoptera / Q000502:physiology*; D008297:Male; D015394:Molecular Structure; D012724:Sex Attractants / Q000096:biosynthesis* / Q000737:chemistry / Q000502:physiology; D013045:Species Specificity
chemical_list: D012724:Sex Attractants