The sex pheromones of two pine sawfly species, Gilpinia frutetorum and Gilpinia socia: chemical identification, synthesis and biological activity.
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.
Hedenström
Erik
E
Department of Natural Sciences, Technology and Mathematics, Mid Sweden University, SE-851 70 Sundsvall, Sweden. erik.hedenstrom@miun.se
Edlund
Helene
H
Wassgren
Ann-Britt
AB
Bergström
Gunnar
G
Anderbrant
Olle
O
Ostrand
Fredrik
F
Sierpinski
Andrzej
A
Auger-Rozenberg
Marie-Anne
MA
Herz
Annette
A
Heitland
Werner
W
Varama
Martti
M
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
D012724:Sex Attractants