Transformation of presumptive precursors to frontalin and exo-brevicomin by bark beetles and the West Indian sugarcane weevil (Coleoptera)

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 3, 1996, Pages 445-450

  Perez, Alice L ^a   Gries, Regine ^a   Gries, Gerhard ^a   Oehlschlager, Allan C ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ARUNDINARIA; COLEOPTERA; DENDROCTONUS PONDEROSAE; DENDROCTONUS RUFIPENNIS; IPS PINI; IPS TRIDENS; METAMASIUS HEMIPTERUS; PICEA; PINUS MUGO; SACCHARUM; SACCHARUM HYBRID CULTIVAR; SCOLYTINAE; TRIDENS;

BREVICOMIN; FRONTALIN;

ANIMAL TISSUE; ARTICLE; BEETLE; BIOSYNTHESIS; CHIRALITY; FEMALE; GAS CHROMATOGRAPHY; INSECT; MALE; MASS SPECTROMETRY; NONHUMAN; REACTION ANALYSIS; SEX DIFFERENCE;

ACETALS; ANIMALS; BEETLES; BICYCLO COMPOUNDS, HETEROCYCLIC; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; KETONES; MALE; PHEROMONES; STEREOISOMERISM;

EID: 0029887613     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00024-7     Document Type: Article

References (31)

1. (a) White, R. A.; Agosin, M.; Franklin, R. T.; Webb, J. W. Z. Angew. Entomol. 1980, 90, 254;
2. (b) Borden, J. H. Aggregation Pheromones: Comprehensive Insect Physiology, Biochemistry and Pharmacology; Kerkut, G. A.; Gilbert, L. I., Eds; Pergamon; Oxford, 1985; Vol. 9;
3. (c) Vanderwel, D.; Oehlschlager, A. C. In Pheromone Biochemistry; Prestwich, D. G.; Blomquist, G. J., Eds; Academic; Orlando, 1987;
4. (d) Bestmann, H. J.; Vostrowsky, O. In Handbook of Natural Pesticides, Pheromones Part A; Morgan, E. D.; Mandava, N. B., Eds; CRC; Boca Raton, 1988, Vol. IV.
5. (a) Hughes, P. R.; Renwick, J. A. A. Physiol. Entomol. 1977, 2, 117;
6. (b) Renwick, J. A. A.; Dickens, J. C. Physiol. Entomol. 1979, 4, 377;
7. (c) Byers, J. Science 1983, 220, 624;
8. (d) Byers, J. A. J. Insect Physiol. 1983, 29, 5;
9. (e) Hunt, D. W. A.; Borden, J. H.; Pierce, H. D. Jr; Slessor, K. N.; King, G. G. S.; Czyzewska, E. J. Chem. Ecol. 1986, 12, 1579.
10. (a) Renwick, J. A. A; Hughes, P. R.; Pitman, G. B.; Vité, J. P. J. Insect Physiol. 1976, 22, 725;
11. (b) Borden, J. H.; Nair, K. K.; Slater, C. E. Science 1969, 1626;
12. (c) Klimetzek, D.; Francke, W. Experientia 1980, 36, 1343;
13. (d) Lindströn, M; Norim, T.; Birgersson, G.; Schlyter, F. J. Chem. Ecol. 1989, 15, 541.
14. Byers, J. A.; Birgersson, G. Naturwissenschaften 1990, 77, 385.
15. Tumlinson, J. H.; Gueldner, R. C.; Hardee, D. D.; Thompson, A. C.; Hedin, P. A.; Minyard, J. P. In Chemicals Controling Insect Behavior, Beroza, M., Ed.; Academic; New York, 1970.
16. Mitlin, N.; Hedin, P. A. J. Insect Physiol. 1974, 20, 1825.
17. (a) Vanderwel, D.; Gries, G.; Singh, S. M.; Borden, J. H.; Oehlschlager, A. C. J. Chem. Ecol. 1992, 18, 1389;
18. (b) Vanderwel, D.; Oehlschlager, A. C. J. Am. Chem. Soc. 1992, 114, 5081.
19. Brand, J. M.; Young, J. C.; Silverstein, R. M. Fortsch. Chem. Org. Naturst. 1979, 37, 1.
20. Francke, W.; Bartels, J.; Meyer, H.; Schröder, F.; Kohnle, U.; Baader, E.; Vité, J. P. J. Chem. Ecol. 1995, 27, 1043.
21. Kinzer, G. W.; Fentiman, A. F. Jr; Page, T. F. Jr; Foltz, R. L.; Vité, J. P.; Pitman, G. B. Nature 1969, 221, 477.
22. Gries, G.; Pierce, H. D. Jr; Lindgren, B. S.; Borden, J. H. J. Econ. Entomol. 1988, 81, 1715.
23. Gries, G. J. Appl. Entomol. 1992, 114, 240.
24. Armstrong, R. N. CRC Crit. Rev. Biochem. 1987, 22, 39.
25. Vité, J. P.; Bakke, A.; Renwick, J. A. A. Can. Entomol. 1972, 104, 1967.
26. Gries, G.; Bowers, W. W.; Gries, R.; Noble, M.; Borden, J. H. J. Insect Physiol. 1990, 36, 819.
27. Still, W. C.; Kanh, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
28. Pearce, G. T.; Gore, W. E.; Silverstein, R. M. J. Org. Chem. 1976, 41, 2797.
29. Serebryakov, E. P.; Gamalevich, G. D. Bull. Acad. Sci. USSR 1987, 36, 116.
30. Fujisawa, T.; Sato, T.; Gotoh, Y.; Kanashima, M.; Kanara, T. Bull. Chem. Soc. Jpn 1982, 55, 3555.
31. Oppolzer, W.; Kündig, E. P.; Bishop, P. M.; Perret, C. Tetrahedron Lett. 1982, 3901.