Aphrodisiac pheromones from the wings of the small cabbage white and large cabbage white butterflies, Pieris rapae and Pieris brassicae

ChemBioChem

Volumn 10, Issue 10, 2009, Pages 1666-1677

  Yildizhan, Selma ^a   van Loon, Joop ^b   Sramkova, Anna ^c   Ayasse, Manfred ^c   Arsene, Christian ^a   ten Broeke, Cindy ^b   Schulz, Stefan ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c UNIVERSITY OF ULM   (Germany)

Author keywords

Lepidoptera; Macrolides; Metathesis; Pheromones; Terpenoids

Indexed keywords

ALKANE DERIVATIVE; APHRODISIAC AGENT; ISOPRENE; MACROLIDE; PHEROMONE; PHYTOL;

ARTICLE; BEETLE; BIOASSAY; BIOLOGICAL ACTIVITY; BUTTERFLY; CONTROLLED STUDY; CUTICLE; DIASTEREOISOMER; FEMALE; FORELIMB; GAS CHROMATOGRAPHY; MALE; MATING; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; RING CLOSING METATHESIS; SPECIES DIFFERENCE;

ANIMALS; CHROMATOGRAPHY, GAS; FEMALE; LACTONES; LEPIDOPTERA; MALE; PHYTOL; SEX ATTRACTANTS; SEXUAL BEHAVIOR, ANIMAL; TERPENES; WING;

COLEOPTERA; LEPIDOPTERA; PAPILIONOIDEA; PIERIS BRASSICAE; PIERIS RAPAE;

EID: 70349554683     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900183     Document Type: Article

References (57)

1. L. P. Brower, J. V. Z. Brower, E. P. Cranston, Zoologica 1965, 50, 1-39.
2. T. E. Pliske, T. Eisner, Science 1969, 164, 1170-1172.
3. J. Meinwald, Y. C. Meinwald, P. H. Mazzocchi, Science 1969, 164, 1174-1175.
4. D. Schneider, U. Seibt, Science 1969, 164, 1173-1174.
5. R. Nishida, S. Schulz, C. H. Kim, H. Fukami, Y. Kuwahara, K. Honda, N. Hayashi, J. Chem. Ecol. 1996, 22, 949-972.
6. C. Arsene, S. Schulz, J. J. A. van Loon, J. Chem. Ecol. 2002, 28, 2627-2631.
7. J. Watson, Mem. Lit. Philos. Soc. Manchester 1865, 3, 63.
8. G. Bergström, L. Lundgren, Zoon 1973, Suppl. 1, 67-75.
9. M. Boppré, Chemically Mediated Interactions Between Butterflies, The Biology of Butterflies, Academic Press, London, 1984.
10. A. Yoshida, A. Noda, A. Yamana, H. Numata, J. Entomol. Sci. 2000, 3, 345-349.
11. J. Andersson, A. K. Borg-Karlson, N. Vongvanich, C. Wiklund, J. Exp. Biol. 2007, 210, 964-970.
12. R. L. Rutowski, J. Comp. Physiol. A 1977, 115, 75-85.
13. R. L. Rutowski, J. Chem. Ecol. 1980, 6, 13-26.
14. J. W. Grula, J. D. McChesney, O. R. Taylor, J. Chem. Ecol. 1980, 6, 241-256.
15. R. S. Papke, D. J. Kemp, R. L. Rutowski, Anim. Behav. 2007, 73, 47-54.
16. T. W. Sappington, O. R. Taylor, J. Chem. Ecol. 1990, 16, 2771-2786.
17. T. W. Sappington, O. R. Taylor, J. Chem. Ecol. 1990, 16, 2755-2770.
18. E. Kan, T. Hidaka, J. Ethol. 1997, 15, 87-93.
19. O. Ohguchi, T. Hidaka, J. Ethol. 1988, 6, 49-53.
20. K. Honda, M. Kawatoko, Appl. Entomol. Zool. 1982, 17, 325-331.
21. J. Andersson, A. K. Borg-Karlson, C. Wiklund, Proc. R. Soc. London Ser. B 2000, 267, 1271-1275.
22. J. Andersson, A. K. Borg-Karlson, C. Wiklund, Proc. R. Soc. London Ser. B 2004, 271, 1765-1770.
23. J. Andersson, A. K. Borg-Karlson, C. Wiklund, J. Chem. Ecol. 2003, 29, 1489-1499.
24. S. Schulz, C. Estrada, S. Yildizhan, M. Boppré, L. E. Gilbert, J. Chem. Ecol. 2008, 34, 82-93.
25. J. W. Wong, V. Verigin, A. C. Oehlschlager, H. J. Borden, H. D. Pierce, Jr., A. M. Pierce, L. Chong, J. Chem. Ecol. 1983, 9, 451-474.
26. P. Baumhof, R. Mazitschek, A. Giannis, Angew. Chem. 2001, 113, 3784-3786;
27. P. Baumhof, R. Mazitschek, A. Giannis, Angew. Chem. Int. Ed. 2001, 40, 3672-3674.
28. A. K. Chatterjee, R. H. Grubbs, Org. Lett. 1999, 1, 1751-1753.
29. A. F. Barrero, E. J. Alvarez-Manzaneda, P. L. Palomino, Tetrahedron 1994, 50, 13239-13250.
30. E. J. Corey, M. C. Noe, W. C. Shieh, Tetrahedron Lett. 1993, 34, 5995-5998.
31. P. A. Zoretic, H. Fang, A. A. Ribeiro, J. Org. Chem. 1998, 63, 7213-7217.
32. B. O'Connor, G. Just, Tetrahedron Lett. 1987, 28, 3235-3236.
33. A. C. Oehlschlager, J. W. Wong, V. G. Verigin, H. D. Pierce, J. Org. Chem. 1983, 48, 5009-5017.
34. B. A. Cheskis, N. A. Shpiro, A. M. Moiseenkov, J. Org. Chem. 1989, 25, 2389-2393.
35. I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem. 2004, 69, 1822-1830.
36. S. Schulz, R. Nishida, Bioorg. Med. Chem. 1996, 4, 341-349.
37. S. Schulz, Lipids 2001, 36, 637-647.
38. F. P. Schiestl, M. Ayasse, H. F. Paulus, C. Löfstedt, B. S. Hansson, F. Ibarra, W. Francke, J. Comp. Physiol. A 2000, 186, 567-574.
39. R. Bloch, C. Brillet, Synlett 1991, 11, 829-830.
40. Y. Sasaerila, R. Gries, G. Gries, G. Khaskin, S. King, S. Takacs, Hardi, Chemoecology 2003, 13, 89-93.
41. S. Schulz, M. Boppré, R. I. Vane-Wright, Phil. Trans. R. Soc. B 1993, 342, 161-181.
42. N. V. Vendilo, K. V. Lebedeva, V. L. Ponomarev, V. A. Pletnev, Agrokhimiya 1998, 12, 52-56.
43. M. A. Mohamed, S. S. Quisenberry, D. J. Moellenbeck, J. Chem. Ecol. 1992, 18, 673-682.
44. C. M. Nieberding, H. Vos, M. V. Schneider, J.-M. Lassance, N. Estramil, J. Andersson, J. Bfng, E. Hedenström, C. Löfstedt, P. M. Brakefield, PLoS One 2008, 3, e2751.
45. P. L. Phelan, P. J. Silk, C. J. Northcott, S. H. Tan, T. C. Baker, J. Chem. Ecol. 1986, 12, 135-146.
46. J. R. Rocca, J. L. Nation, L. Strekowski, M. A. Battiste, J. Chem. Ecol. 1992, 18, 223-244.
47. K. E. Espelie, B. A. Bernays, J. Chem. Ecol. 1989, 15, 2003-2017.
48. P. G. Hatcher, B. R. T. Simoneit, F. T. Mackenzie, A. C. Neumann, D. C. Thorstenson, S. M. Gerchakov, Org. Geochem. 1982, 4, 93-112.
49. K. Mori, Y. Nakazano, Liebigs Ann. Chem. 1988, 167-174.
50. A. X. Huang, Z. Xiong, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 9999-10003.
51. R. J. Anderson, C. A. Henrick, J. B. Siddall, R. Zurflueh, J. Am. Chem. Soc. 1972, 94, 5379-5386.
52. Z. Liu, W. Z. Li, L. Peng, Y. Li, Y. Li, J. Chem. Soc. Perkin Trans. 1 2000, 4250-4257.
53. F.-D. Boyer, P.-H. Ducrot, Eur. J. Org. Chem. 1999, 1201-1211.
54. K. Tago, M. Arai, H. Kogen, J. Chem. Soc. Perkin Trans. 1 2000, 2073-2078.
55. R. Neidlein, E. Koch, Arch. Pharm. 1980, 313, 193-198.
56. L. Zhao, C. Jin, Z. Mao, M. B. Gopinathan, K. Rehder, R. D. Brinton, J. Med. Chem. 2007, 50, 4471-4481.
57. S. H. Kang, S. B. Lee, C. M. Park, J. Am. Chem. Soc. 2003, 125, 15748-15749.