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Z Naturforsch C J Biosci

Title:		"The sex pheromones of two pine sawfly species, Gilpinia frutetorum and Gilpinia socia: 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, Technology and Mathematics, Mid Sweden University, SE-851 70 Sundsvall, Sweden. erik.hedenstrom@miun.se"
Journal Title:		Z Naturforsch C J Biosci
Year:		2009
Volume:		64
Issue:		9-Oct
Page Number:		733 - 742
DOI:		10.1515/znc-2009-9-1020
ISSN/ISBN:		0939-5075 (Print) 0341-0382 (Linking)
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"
Keywords:		"Animals Chromatography, Gas Female Hymenoptera/*physiology Male Molecular Structure Sex Attractants/*biosynthesis/chemistry/physiology Species Specificity;"
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 Germany 2009/12/05 Z Naturforsch C J Biosci. 2009 Sep-Oct; 64(9-10):733-42. doi: 10.1515/znc-2009-9-1020"