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J Chem Ecol

Title:		"Sex pheromone of the pine sawfly, Gilpinia pallida: chemical identification, synthesis, and biological activity"
Author(s):		Hedenstrom E; Edlund H; Wassgren AB; Bergstrom G; Anderbrant O; Ostrand F; Sierpinski A; Auger-Rozenberg MA; Herz A; Heitland W; Varama M;
Address:		"Department of Natural Sciences, Mid Sweden University, 85170, Sundsvall, Sweden. erik.hedenstrom@miun.se"
Journal Title:		J Chem Ecol
Year:		2006
Volume:		32
Issue:		11
Page Number:		2525 - 2541
DOI:		10.1007/s10886-006-9161-5
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
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"
Keywords:		"Animals Electrophysiology Female Gas Chromatography-Mass Spectrometry Hymenoptera/*metabolism/physiology Male Sex Attractants/chemical synthesis/*metabolism/pharmacology Spectrophotometry, Infrared;"
Notes:		"MedlineHedenstrom, Erik Edlund, Helene Wassgren, Ann-Britt Bergstrom, Gunnar Anderbrant, Olle Ostrand, Fredrik Sierpinski, Andrzej Auger-Rozenberg, Marie-Anne Herz, Annette Heitland, Werner Varama, Martti eng Research Support, Non-U.S. Gov't 2006/11/01 J Chem Ecol. 2006 Nov; 32(11):2525-41. doi: 10.1007/s10886-006-9161-5"