Sex pheromone of the pine sawfly, Gilpinia pallida: chemical identification, synthesis, and biological activity.
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.
Hedenström
Erik
E
Department of Natural Sciences, Mid Sweden University, 85170, 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; 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
D012724:Sex Attractants