Male Phyllotreta striolata (F.) produce an aggregation pheromone: Identification of male-specific compounds and interaction with host plant volatiles

Journal of Chemical Ecology

Volumn 37, Issue 1, 2011, Pages 85-97

  Beran, Franziska ^a   Mewis, Inga ^b   Srinivasan, Ramasamy ^c   Svoboda, Jiří ^d   Vial, Christian ^e   Mosimann, Hervé ^e   Boland, Wilhelm ^d   Büttner, Carmen ^a   Ulrichs, Christian ^a   Hansson, Bill S ^d   Reinecke, Andreas ^d  

^a HUMBOLDT UNIVERSITY   (Germany)

^b Inst Veg Orn Crops G Erfurt   (Germany)

^c AVRDC THE WORLD VEGETABLE CENTER   (Taiwan)

^d MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^e NONE   (Switzerland)

Author keywords

11 diene; Aggregation pheromone; Allyl isothiocyanate; Brassica; Chrysomelidae; Coleoptera; Gas chromatography mass spectrometry (GC MS); Glucosinolate hydrolysis products; Host plant volatiles; Phyllotreta striolata

Indexed keywords

ATTRACTANT; BEETLE; CROP PEST; DICOTYLEDON; ESTER; EVERGREEN TREE; GAS CHROMATOGRAPHY; HOST PLANT; INTEGRATED PEST MANAGEMENT; MASS SPECTROMETRY; PHEROMONE; PHYSIOLOGICAL RESPONSE; TRAP (EQUIPMENT); VOLATILE ORGANIC COMPOUND;

TAIWAN;

ABIES; ABIES NORDMANNIANA; BRASSICA; BRASSICACEAE; CEDRUS; CEDRUS ATLANTICA; CHRYSOMELIDAE; COLEOPTERA; PHYLLOTRETA STRIOLATA;

EID: 79251631523     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-010-9899-7     Document Type: Article

References (53)

1. ANDERSEN, N. H., BISSONETTE, P., LIU, C. B., SHUNK, B., OHTA, Y., TSENG, C. L. W., MOORE, A., and HUNECK, S. 1977. Sesquiterpenes of nine European liverworts from the genera, Anastrepta, Bazzania, Jungermannia, Lepidozia, and Scapania. Phytochemistry 16:1731-1751.
2. AYRES, B. D., AYRES, M. P., ABRAHAMSON, M. D., and TEALE, S. A. 2001. Resource partitioning and overlap in thee sympatric species of Ips bark beetles (Coleoptera: Scolytidae). Oecologia 128:443-453.
3. BARTELT, R. J., WEAVER, D. K., and ARBOGAST, R. T. 1995. Aggregation pheromone of Carpophilus dimidatus (F.) (Coleoptera: Nitidulidae) and responses to Carpophilus pheromones in South Carolina. J. Chem. Ecol. 21:1763-1779.
4. BARTELT, R. J., COSSÉ, A. A., ZILKOWSKI, B. W., WEISLEDER, D., and MOMANY, F. A. 2001. Male-specific sesquiterpenes from Phyllotreta and Aphthona flea beetles. J. Chem. Ecol. 27:2397-423.
5. BARTELT, R. J., WEISLEDER, D., and MOMANY, F. A. 2003. Total synthesis of himachalene sesquiterpenes of Aphthona and Phyllotreta flea beetles. Synthesis 117-123.
6. BARTELT, R. J., COSSÉ, A. A., ZILKOWSKI, B. W., WEISLEDER, D., GRODE, S. H., WIEDENMANN, R. N., and POST, S. L. 2006. Dimethylfuran-lactone pheromone from males of Galerucella calmariensis and Galerucella pusilla. J. Chem. Ecol. 32:693-712.
7. BURGESS, L. 1977. Flea beetles (Coleoptera-Chysomelidae) attacking rape crops in the Canadian prairie provinces. Can. Entomol. 109: 21-32.
8. CHEN, C. C., SHY, J. F., KO, W. F., HWANG, T. F., and LIN, C. S. 1991. Studies on the ecology and control of Phyllotreta striolata (Fab.) (II) Developmental duration and population fluctuation. Plant Protection Bulletin (Taipei), 33:354-363.
9. COSSÉ, A. A., BARTELT, R. J., and ZILKOWSKI, B. W. 2002. Identification and electrophysiological activity of a novel hydroxy ketone emitted by male cereal leaf beetles. J. Nat. Prod. 65:1156-1160.
10. COSSÉ, A. A., BARTELT, R. J., ZILKOWSKI, B. W., BEAN, D. W., and ANDRESS, E. R. 2006. Behaviorally active green leaf volatiles for monitoring the leaf beetle, Diorhabda elongata, a biocontrol agent of saltcedar, Tamarix spp. J. Chem. Ecol. 32:2695-2708.
11. CSONKA, É., TÓTH, M., and UJVÁRY, I. 2007. Differences in host-plant related chemical communication of the flea beetles Phyllotreta cruciferae Goeze and Ph. vittula Redtenbacher (Coleoptera, Chysomelidae). Acta Phytopathol. Hun. 42:343-352.
12. DICKENS, J. C., OLIVER, J. E., HOLLISTER, B., DAVIS, J. C., and KLUN, J. A. 2002. Breaking a paradigm: Male produced aggregation pheromone for the Colorado potato beetle. J. Exp. Biol. 205:1925-1933.
13. DICKENS, J. C. 2006. Plant volatiles moderate response to aggregation pheromone in Colorado potato beetle. J. Appl. Entomol. 130: 26-31.
14. FAHEY, J. W., ZALCMANN, A. T., and TALALAY P. 2001. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56:5-51.
15. FEENY, P., PAAUWE, K. L., and DEMONG, N. J. 1970. Flea beetles and mustard oils: host plant specificity of Phyllotreta cruciferae and P. striolata adults (Coleoptera: Chysomelidae). Ann. Entomol. Soc. Am. 63:832-841.
16. GÖRNITZ, K. 1956. Weitere Untersuchungen über Insekten-Attraktivstoffe aus Cruciferen. Nachichtenblatt Deutscher Pflan-zenschutzdienst 10:137-147.
17. GRUBER, M. Y., XU, N., GRENKOW, L., LI, X., ONYILAGHA, J., SOROKA, J. J., WESTCOTT, N. D., and HEGEDUS, D. D. 2009. Responses of the crucifer flea beetle to Brassica volatiles in an olfactometer. Environ. Entomol. 38:1467-1479.
18. HOFMANN, J., ZIMMERMANN, G., and KOPINKE, F. D. 1994. The thermal aromatization of methyl-1,3-cyclohexadienes - An important argument against commonly accepted sigmatropic 1,7-H-shift reactions. J. Prakt. Chem. 336:201-206.
19. HEIKERTINGER, F. 1941. Bestimmungstabelle der paläarktischen Phyllotreta-Arten. Kol. Rundsch. 27:15-64, 69-116.
20. JOSEPH, T. C. and DEV, S. 1968. Studies in Sesquiterpenes-XXXI Absolute stereochemistry of himachalenes. Tetrahedron 24:3841-3852.
21. KAISSLING, K. E. 1971. Insect Olfaction, pp. 351-431. in L. M Beidler (ed.). Handbook of Sensory Physiology, vol. IV. Chemical Senses Springer Verlag, Berlin.
22. LAMB, R. J. 1989. Entomology of oilseed Brassica crops. Annu. Rev. Entomol. 34:211-229.
23. LANDOLT, P. J. and PHILLIPS, T. W. 1997. Host plant influences on sex pheromone behaviour of phytophagous insects. Annu. Rev. Entomol. 42:371-391.
24. MITCHELL, B. K. 1994. The chemosensory basis of host-plant recognition in Chysomelidae, pp. 141-151. in P. H. Jolivet, M. L. Cox, and E. Petitpierre (eds.). Novel Aspects of the Biology of Chysomelidae. Kluwer Academic Pub.
25. MMOHAMEDSAID, M. S. 2004. Catalogue of the Malaysian Chysomelidae (Insecta: Coleoptera). Pensoft, Sofia-Moscow.
26. MORI, K. 2005. Synthesis of (R)-ar-turmerone and its conversion to (R)-ar-himachalene, a pheromone component of the flea beetle: (R)-ar-himachalene is dextrorotatory in hexane, while levorotatory in chloroform. Tetrahedron: Asymmetry 16:685-692.
27. MUTO, S., BANDO, M., and MORI, K. 2004. Synthesis and stereochemistry of the four himachalene-type sesquiterpenes isolated from the flea beetle (Aphthona flava) as pheromone candidates. Eur. J. Org. Chem. 1946-1952.
28. NIELSEN, J. K. 1988. Crucifer-feeding Chysomelidae: mechanisms of host plant finding and acceptance, pp. 25-40. in P. H. Jolivet, E. Petitpierre, and T. H. Hsiao (eds.). Biology of Chysomelidae. Kluwer Academic Pub.
29. NIELSEN, J. K., HANSEN, M. L., AGERBIRK, N., PETERSEN, B. L., and HALKIER, B. A. 2001. Responses of the flea beetles Phyllotreta nemorum and P. cruciferae to metabolically engineered Arabidopsis thaliana with an altered glucosinolate profile. Chemoecology 11:75-83.
30. PANDY, R. C. and DEV, S. 1968. XXX Synthesis of ar-himachalene and himachalanes. Tetrahedron 24:3829-3839.
31. PARKER, B. L., TALEKAR, N. S., and SKINNER M. 1995. Field Guide: Insect pests of selected vegetables in tropical and subtropical Asia. Asian Vegetable Research and Development Center, Shanhua, Tainan, Taiwan.
32. PENG, C. and WEISS, M. J. 1992. Evidence of an aggregation pheromone in the flea beetle, Phyllotreta cruciferae (Goeze) (Coleoptera: Chysomelidae) J. Chem. Ecol. 18:875-884.
33. PENG, C., BARTELT, R. J., and WEISS, M. J. 1999. Male crucifer flea beetles produce an aggregation pheromone. Physiol. Entomol. 24:98-99.
34. PIVNICK, K. A. and JARVIS, B. J. 1991. Rate of release of allyl isothiocyanate by intact and damaged oriental mustard plants and implications for host plant location by insects. pp. 512-517 in D. I. McGregor (ed.). Proceedings, VII International Rapeseed Congress. Groupe Consultatif International de Recherche sur le Colza. Paris, France.
35. PIVNICK, K. A., LAMB, R. J., and REED, D. 1992. Response of flea beetles, Phyllotreta spp., to mustard oils and nitriles in field trapping experiments. J. Chem. Ecol. 18:863-873.
36. RAO, S., COSSÉ, A. A., ZILKOWSKI, B. W., and BARTELT, R. J. 2003. Aggregation pheromone of the cereal leaf beetle: field evaluation and emission from males in the laboratory. J. Chem. Ecol 29:2165-2175.
37. REDDY, G. V. P. and GUERRERO, A. 2004. Interactions of insect pheromones and plant semiochemicals. Trends Plant Sci. 9:253-261.
38. REINECKE, A., RUTHER, J., TOLASCH, T., FRANCKE, W., and HILKER, M. 2002a. Alcoholism in cockchafers: orientation of male Melolontha melolontha towards green leaf alcohols. Naturwissenschaften 89:265-269.
39. REINECKE, A., RUTHER, J., and HILKER, M. 2002b. The scent of food and defence: green leaf volatiles and toluquinone as sex attractant mediate mate finding in the European cockchafer Melolontha melolontha. Ecol. Lett. 5:257-263.
40. REINECKE, A., RUTHER, J,. and HILKER, M. 2006. Pre-copulatory isolation in sympatric Melolontha species (Coleoptera: Scarabaeidae). Agr. For. Entomol. 8:289-293.
41. RENWICK, J. A. A. 2002. The chemical world of crucivores: lures, treats and traps. Entomol. Exp. Appl. 104:35-42.
42. RUTHER, J., REINECKE, A., THIEMANN, K., TOLASCH, T., FRANCKE, W., and HILKER, M. 2000. Mate finding in the forest cockchafer, Melolontha hippocastani, mediated by volatiles from plants and females. Physiol. Entomol. 25:172-179.
43. RUTHER, J., REINECKE, A., and HILKER, M. 2002. Plant volatiles in the sexual communication of Melolontha hippocastani: response towards time-dependent bouquets and novel function of (Z)-3-hexen-1-ol as a sexual kairomone. Ecol. Entomol. 27:76-83.
44. SANO, S. and MORI, K. 1999. Pheromone Synthesis, CXCV, Synthesis of (1R*,3R*,7R*)-3-mhimachalene, the racemate of the male-produced sex pheromone of the sandfly Lutzomyia longipalpis from Jacobina, Brazil. Eur. J. Org. Chem. 1679-1686.
45. SEYBOLD, S. J., HUBER, D. P. W., LEE, J. C., GRAVES, A. D., and BOHLMANN, J. 2006. Pine monoterpenes and pine bark beetles: A marriage of convenience for defense and chemical communication. Phytochem. Rev. 5:143-178.
46. SOROKA, J. J., BARTELT, R. J., ZILKOWSKI, B. W., and COSSÉ, A. A. 2005. Responses of flea beetle Phyllotreta cruciferae to synthetic aggregation pheromone components and host plant volatiles in field trials. J. Chem. Ecol. 31:1829-1843.
47. TÓTH, M., CSONKA, E., BARTELT, R. J., COSSÉ, A. A., ZILKOWSKI, B. W., MUTO, S. E., and MORI, K. 2005. Pheromonal activity of compounds identified from male Phyllotreta cruciferae: field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate. J. Chem. Ecol. 31:2705-2720.
48. TÓTH, M., CSONKA, È., BAKCSA, F., BENEDEK, P., SZARUKÁN, I., GOMBOC, S., TOSHOVA, T., SUBCHEV, M., and UJVÁRY, I. 2007. Species spectrum of flea beetles (Phyllotreta spp., Coleoptera: Chrysomelidae) attracted to allyl isothiocyanate-baited traps. Z. Naturforsch. C. 62:772-778.
49. VAN DEN DOOL, H. and KRATZ, P. D. 1963. A generalization of the retention index system including linear temperature programmed gas-liquid partition chromatography. J. Chromatogr. 11:463-471.
50. VAN EPP JR., J. E., BOYD, D. R., and BERCHTOLD, G. A. 1981. Aromatization of arene 1,2-oxides. 1-(trimethylsilyl)benzene 1,2-oxide. J. Org. Chem. 46:1817-1820.
51. VERKERK, R., SCHEINER, M., KRUMBEIN, A., CISKA, E., HOLST, B., ROWLAND, I., DE SCHIJVER, R., HANSEN, M., GERHÄUSER, C., MITHEN R., and DEKKER M. 2009. Glucosinolates in Brassica vegetables: The influence of the food supply chain on intake, bioavailability and human health. Mol. Nutr. Food Res. 53:219-265.
52. WERTHEIM, B., VAN BAALEN, E.-J., DICKE, M., and VET, L. E. M. 2004. Pheromone-mediated aggregation in non-social arthopods: an evolutionary ecological perspective. Annu. Rev. Entomol. 50:321-346.
53. ZILKOWSKI, B. W., BARTELT, R. J., COSSÉ, A. A., and PETROSKI, R. J. 2006. Male-produced aggregation pheromone compounds from the eggplant flea beetle (Epitrix fuscula): identification, synthesis, and field bioassays. J. Chem. Ecol. 32:2543-2558.