Sex pheromone of the pine sawfly, Gilpinia pallida: Chemical identification, synthesis, and biological activity

Journal of Chemical Ecology

Volumn 32, Issue 11, 2006, Pages 2525-2541

  Hedenström, Erik ^a   Edlund, Helene ^a   Wassgren, Ann Britt ^b   Bergström, Gunnar ^b   Anderbrant, Olle ^c   Östrand, Fredrik ^c   Sierpinski, Andrzej ^d   Auger Rozenberg, Marie Anne ^e   Herz, Annette ^f,h   Heitland, Werner ^f   Varama, Martti ^g  

^a MID SWEDEN UNIVERSITY   (Sweden)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

^c LUND UNIVERSITY   (Sweden)

^d FOREST RESEARCH INSTITUTE   (Poland)

^e CEMAGREF   (France)

^f TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^g FINNISH FOREST RESEARCH INSTITUTE   (Finland)

^h INSTITUTE FOR EPIDEMIOLOGY AND PATHOGEN DIAGNOSTICS   (Germany)

Author keywords

3,7 Dimethyl 2 tetradecanol; Electrophysiology; Field activity; Gas chromatography; Gilpinia pallida; Lipase; Mass spectrometry; Sex pheromone; Stereoisomer; Synthesis

Indexed keywords

SEX PHEROMONE;

ANTENNA; FLY; IDENTIFICATION METHOD; PHYSIOLOGICAL RESPONSE; SEX PHEROMONE;

ANIMAL; ARTICLE; ELECTROPHYSIOLOGY; FEMALE; HYMENOPTERA; INFRARED SPECTROPHOTOMETRY; MALE; MASS FRAGMENTOGRAPHY; METABOLISM; PHYSIOLOGY; SYNTHESIS;

ANIMALS; ELECTROPHYSIOLOGY; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HYMENOPTERA; MALE; SEX ATTRACTANTS; SPECTROPHOTOMETRY, INFRARED;

GILPINIA PALLIDA;

EID: 33751119255     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-006-9161-5     Document Type: Article

References (29)

1. ANDERBRANT, O. 1993. Pheromone biology of sawflies, pp. 119-154, in M. R. Wagner and K. F. Raffa (eds.). Sawfly Life History Adaptations to Woody Plants. Academic Press, New York.
2. ANDERBRANT, O. 1999. Sawflies and seed wasps, pp. 199-226, in J. Hardie and A. K. Minks (eds.). Pheromones of Non-Lepidopteran Insects Associated with Agricultural Plants. CAB International, Wallingford, UK.
3. ANDERBRANT, O., LÖFQVIST, J., JÖNSSON, J., and MARLING, E. 1989. Effects of pheromone trap type, position and colour on the catch of the pine sawfly Neodiprion sertifer (Geoff.) (Hym., Diprionidae). J. Appl. Entomol. 107:365-369.
4. ANDERBRANT, O., LÖFQVIST, J., BENGTSSON, M. and BAECKSTRÖM, P. 1992. Field response of the pine sawfly Neodiprion sertifer to controlled release of diprionyl acetate, diprionyl propionate and transperillenal. J. Chem. Ecol. 18:1707-1725.
5. ANDERBRANT, O., ÖSTRAND, F., BERGSTRÖM, G., WASSGREN, A.-B., AUGER-ROZENBERG, M.-A., GERI, C., HEDENSTRÖM, E., HÖGBERG, H.-E., HERZ, A., and HEITLAND, W. 2005. Release of sex pheromone and its precursors in the pine sawfly Diprion pini. Chemoecology 15:147-151.
6. BERGSTRÖM, G., WASSGREN, A.-B., ANDERBRANT, O. HEDENSTRÖM, E., HÖGBERG, H.-E., FÄGERHAG, J., EDLUND, H., GERI, C. AUGER, M. A., VARAMA, M., HANSSON, B. S., and LÖFQVIST, J. 1995. Sex pheromone of the pine sawfly Diprion pini (Hymenoptera: Diprionidae): Chemical identification, synthesis and biological activity. Experientia 51:370-380.
7. BERGSTRÖM, G., WASSGREN, A.-B., ANDERBRANT, O., OCHIENG, S. A., ÖSTRAND, F., HANSSON, B. S., HEDENSTRÖM, E., and HÖGBERG, H.-E. 1998. The sex pheromone of the pine sawfly Microdiprion pallipes (Hymenoptera: Diprionidae). Naturwissenschaften 85:244-248.
8. HEDENSTRÖM, E. and ANDERSSON, F. 2002. Synthesis of female sex pheromone precursors of pine sawfly species and of some structurally related methyl-branched long-chain 2-alkanols. J. Chem. Ecol. 28:1237-1254.
9. HEDENSTRÖM, E., HÖGBERG, H.-E., WASSGREN, A.-B., BERGSTRÖM, G., LÖFQVIST, J., HANSSON, B., and ANDERBRANT, O. 1992. Sex pheromone of pine sawflies. Chiral synthesis of some active minor components isolated from Neodiprion sertifer and some chiral analogues of diprionyl acetate. Tetrahedron 48:3139-3146.
10. HEDENSTRÖM, E., EDLUND, H., LUND, S., ABERSTEN, M., and PERSSON, D. 2002. Synthesis and lipase catalysed stereoselective acylation of some 3-methylalkan-2-ols, identified as sex pheromone precursors in females of pine sawfly species. J. Chem. Soc., Perkin Trans. 1 2002:1810-1817.
11. HEDENSTRÖM, E., NGUYEN, B.-V., and SILKS, L. A. III. 2002. Do enzymes recognise remotely located stereocentres? Highly enantioselective Candida rugosa lipase-catalysed esterification of the 2- to 8-methyldecanoic acids. Tetrahedron: Asymmetry 13:835-844.
12. HEDENSTRÖM, E., EDLUND, H., and LUND, S. 2003. Stereoselective esterification of 2,6-dimethyl-1,7-heptanedioic acid, catalysed by Candida rugosa lipase. J. Mol. Catal., B Enzym. 23:53-59.
13. HERZ, A. and HEITLAND, W. 2002. Comparison of the fat allocation patterns in female pine sawflies (Hymenoptera: Diprionidae). Eur. J. Entomol. 99:117-120.
14. HERZ, A., HEITLAND, W., ANDERBRANT, O., EDLUND, H., and HEDENSTRÖM, E. 2000. First use of pheromones to detect phenology patterns and density relationships of pine sawflies in German forests. Agric. For. Entomol. 2:123-129.
15. HÖGBERG, H. -E., HEDENSTRÖM, E., WASSGREN, A. -B., HJALMARSSON, M., BERGSTRÖM, G., LÖFQVIST, J., and NORIN, T. 1990. Synthesis and gas chromatographic separation of the eight stereoisomers of diprionol and their acetates, components of the sex pheromone of pine sawflies. Tetrahedron 46:3007-3018.
16. HÖGBERG, H.-E., HEDENSTRÖM, E., FÄGERHAG, J., and SERVI, S. 1992. Enantioselective synthesis of (S)-2-methyl-1-alkanols via bakers' yeast mediated reduction of α-methyl-2-thiophenepropenals. J. Org. Chem. 57:2052-2059.
17. JEWETT, D. M., MATSUMURA, F., and COPPEL, H. C. 1976. Sex pheromone specificity in the pine sawflies: Interchange of acid moieties in an ester. Science 192:51-53.
18. KARLSSON, S. and HEDENSTRÖM, E. 1999. Sex pheromone of the pine sawfly, Macrodiprion nemoralis. Stereoselective synthesis of the sixteen stereoisomers of 3,7,9-trimethyl-2-tridecyl acetate. Acta Chem. Scand. 53:620-630.
19. KIKUKAWA, T., MATSUMURA, F., KRAEMER, M., COPPEL, H. C., and TAI, A. 1982. Field attractiveness of chirally defined synthetic attractants to males of Diprion similis and Gilpinia frutetorum. J. Chem. Ecol. 8:301-314.
20. KÖNIG, W. A., FRANCKE, W., and BENECKE, I. 1982. Gas chromatographic enantiomer separation of chiral alcohols. J. Chromatogr. 239:227-231.
21. LARSSON, M., NGUYEN, B.-V., HEDENSTRÖM, E., and HÖGBERG, H.-E. 2001. Syntheses of the sixteen stereoisomers of 3,7,11-trimethyl-2-tridecanol, including the (2S,3S,7S,11R)- and (2S,3S,7S,11S)-stereoisomers identified as pheromone precursors in females of the pine sawfly Microdiprion pallipes (Hymenoptera: Diprionidae). Eur. J. Org. Chem. 2001:353-363.
22. LEVENE, P. A. and MARKER, R. E. 1932. Maximum rotations and correlation of disubstituted acetic acids containing a methyl group. J. Biol. Chem. 98:1-7.
23. NIKISHIN, G. I., OGIBINI, Y. N., and RAKHMATULLINA, L. K. 1974. Peroxydisulfate-initiated reactions of 1-heptene with acetic and propionic acids. Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 23:1479-1483.
24. ÖSTRAND, F., WASSGREN, A.-B., ANDERBRANT, O., BERGSTRÖM, G., HEDENSTRÖM, E., HÖGBERG, H.-E., NGUYEN, B.-V., and LARSSON, M. 2003. Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae). Chemoecology 13:155-162.
25. PSCHORN-WALCHER, H. 1982. Unterordnung Symphyta, Pflanzenwespen, pp. 4-234, in W. Schwenke (ed.). Die Forstschädlinge Europas, Bd 4. Paul-Parey Verlag, Hamburg.
26. SMITH, D. R. 1993. Systematics, life history, and distribution of sawflies, pp. 3-32, in M. R. Wagner and K. F. Raffa (eds.). Sawfly Life History Adaptations to Woody Plants. Academic Press, New York.
27. WASSGREN, A.-B. and BERGSTRÖM, G. 1995. Quantitative high-resolution gas chromatographic determination of stereoisomeric composition of chiral volatile compounds in the picogram range by EC-detection. J. Chem. Ecol. 21:987-994.
28. WASSGREN, A.-B., ANDERBRANT, O., LÖFQVIST, J., HANSSON, B. S., BERGSTRÖM, G., HEDENSTRÖM, E., and HÖGBERG, H.-E. 1992. Pheromone related compounds in pupal and adult female pine sawflies, Neodiprion sertifer, of different age and in different parts of the body. J. Insect Physiol. 38:885-893.
29. WASSGREN, A.-B., BERGSTRÖM, G., SIERPINSKI, A., ANDERBRANT, O., HÖGBERG, H.-E., and HEDENSTRÖM, E. 2000. Sex pheromone of the pine sawfly Macrodiprion nemoralis (Hymenoptera: Diprionidae): Identification of the precursor (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecanol and the active pheromone (2S,3R,7R,9S)-3,7,9-trimethyl-2-tridecyl acetate. Naturwissenschaften 87:24-29.