Probing the role of polyphenol oxidation in mediating insect-pathogen interactions. Galloyl-derived electrophilic traps for the Lymantria dispar nuclear polyhedrosis virus matrix protein polyhedrin

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5794-5803

  Feldman, Ken S ^a   Sambandam, Aruna ^a   Bowers, Katherine E ^a   Appel, Heidi M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MATRIX PROTEIN; POLYHEDRIN; POLYPHENOL; TANNIN; VIRUS PROTEIN;

ARTICLE; INSECT; MOTH; NONHUMAN; OLIGOMERIZATION; OXIDATION; PLANT; POLYHEDROSIS VIRUS; PROTEIN ANALYSIS; SPECTROFLUOROMETRY; VIRUS INFECTION;

EID: 0033529727     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982477n     Document Type: Article

References (59)

1. (a) Schultz, J. C. In Chemistry and Significance of Condensed Tannins; Hemingway, R. W., Karchesy, J. J., Eds.; Plenum Press: New York, 1989; p 417 and references therein.
2. (b) Rhoades, D. F.; Cates, R. G. Rec. Adv. Phytochem. 1976, 10, 168.
3. (c) Bernays, E. A.; Driver, G. C.; Bilgener, M. In Advances in Ecological Research; Bergon, M., Fitter, A. H., Ford, E. D., MacFadyen, Eds.; Academic Press: London, 1989; p 263.
4. (d) Feeny, P. Ecology 1970, 51, 565.
5. (e) Martin, J. S.; Martin, M. M.; Bernays, E. A. J. Chem. Ecol. 1987, 13, 605.
6. (f) Feeny, P. Phytochemistry 1969, 8, 2119.
7. (g) Mole, S.; Waterman, P. G. Phytochemistry 1987, 26, 99.
8. (h) Steinly, B. A.; Berenbaum, M. Ent. Exp. Appl. 1985, 39, 3.
9. (i) Bettolo, G. B. M.; Marta, M.; Pomponi, M.; Bernays, E. A. Biochem. Syst. Ecol. 1986, 14, 249.
10. (j) Veau de E. J. I.; Schultz, J. C. J. Chem. Ecol. 1992, 18, 1437.
11. (a) Schultz, J. C.; Hunter, M. D.; Appel, H. M. In Plant Polyphenols: Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; p 621.
12. (b) Schultz, J. C.; Keating, S. T. In Microbial Mediation of Plant-Herbivore Interactions; Barbosa, P., Krischik, V. A., Jones, C. G., Eds.; John Wiley & Sons: New York, 1991; p 489.
13. (c) Hoover, K.; Yee, J. L.; Schultz, C. M.; Rocke, D. M.; Hammock, B. D.; Duffey, S. S. J. Chem. Ecol. 1998, 24, 221.
14. (a) Felton, G. W.; Duffey, S. S. J. Chem. Ecol. 1990, 16, 1221.
15. (b) Felton, G. W.; Donato, K.; del Vecchio, R. J.; Duffey, S. S. J. Chem. Ecol. 1989, 15, 2667.
16. Nakano, H.; Tahara, S.; Iizuka, T.; Mizutani. Agric. Biol. Chem. 1987, 51, 549.
17. (a) Sugumaran, M.; Dali, H.; Semensi, V. Arch. Insect Biochem. Physiol. 1989, 11, 127.
18. (b) Salgues, M.; Cheynier, V.; Gunata, Z.; Wylde, R. J. Food Sci. 1986, 51, 1191.
19. (c) Dudley, E. D.; Hotchkiss, L. H. J. Food Biochem. 1989, 13, 65.
20. (d) Richard, F. C.; Goupy, P. M.; Nicolas, J. J.; Lacombe, J.-M.; Pavia, A. A. J. Agric. Food Chem. 1991, 39, 841.
21. (e) Cilliers, J. J. L.; Singleton, V. L. J. Agric. food Chem. 1990, 38, 1789.
22. (f) Ito, S.; Palumbo, A.; Prota, G. Experientia 1985, 41, 960.
23. (g) Abul-Hajj, Y. J.; Tabakovic, K.; Gleason, W. B.; Ojala, W. H. Chem. Res. Toxicol. 1998, 9, 434.
24. (h) Iverson, S. L.; Shen, L.; Anlar, N.; Bolton, J. L. Chem. Res. Toxicol. 1996, 9, 492.
25. (i) Quideau, S.; Feldman, K. S.; Appel, H. M. J. Org. Chem. 1996, 61, 6656.
26. (j) Merritt, M. E.; Christensen, A. M.; Kramer, K. J.; Hopkins, T. L.; Schaefer, J. J. Am. Chem. Soc. 1996, 118, 11278.
27. (k) Shen, X.-M.; Dryhurst, G. J. Med. Chem. 1996, 39, 2018.
28. (a) Keating, S. T.; Hunter, M. D.; Schultz, J. C. J. Chem. Ecol. 1990, 16, 1445.
29. (b) Rossiter, M.; Schultz, J. C.; Baldwin, I. T. Ecology 1988, 69, 267.
30. (a) Keating, S. T.; Yendol, W. G. Environ. Entomol. 1987, 16, 459.
31. (b) Keating, S. T.; Yendol, W. G.; Schultz, J. C. Environ. Entomol. 1988, 17, 952.
32. (c) Foster, M. A.; Schultz, J. C.; Hunter, M. D. J. Anim. Ecol. 1992, 61, 509.
33. (d) Keating, S. T.; Hunter, M. D.; Schultz, J. C. J. Chem. Ecol. 1990, 16, 1445.
34. (a) Schultz, J. C.; Lechowicz, M. J. Oecologia 1986, 71, 133.
35. (b) Appel, H. M.; Maines, L. W. J. Insect Physiol. 1995, 41, 241.
36. (c) Appel, H. M.; Martin, M. M. J. Chem. Ecol. 1990, 16, 3277.
37. Quideau, S.; Feldman, K. S., J. Org. Chem. 1997, 62, 8809.
38. (a) Matheis, G., Whitaker, J. R. J. Food Biochem. 1984, 137.
39. (b) Hanzlik, R. P.; Harriman, S. P.; Frauenhoff, M. M. Chem. Res. Toxicol. 1994, 7, 177.
40. (c) Xu, R.; Huang, X.; Hopkins, T. L.; Kramer, K. Insect Biochem. Mol. Biol. 1997, 27, 101.
41. (a) Kalyanaraman, B.; Premovic, P. I.; Sealy, R. C. J. Biol. Chem. 1987, 262, 11080.
42. (b) Brunet, P. C. J.; Coles, B. C. Proc. R. Soc. London B. 1974, 187, 133.
43. (c) Sugumaran, M. In Advances in Insect Physiology; Evans, P. D., Wigglesworth, V. L., Eds.; Academic Press: London: 1988; p 179.
44. McMinn, D. L.; Greenberg, M. M. Tetrahedron 1996, 52, 3827.
45. Venkatesan, H.; Greenberg, M. M. J. Org. Chem. 1996, 61, 525.
46. Gegg, C. V.; Bowers, K. E.; Matthews, C. R. In Techniques in Protein Chemistry VII; Academic Press: Orlando, FL, 1996; p 439.
47. Iwakura, M.; Jones, B. J.; Luo, J.; Matthews, C. R. J. Biochem. 1995, 117, 480.
48. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70.
49. (a) Bilimoria, S. L. In Viruses of Invertebrates; Kurstak, E., Ed.; Marcel Dekker: New York, 1991; p 1.
50. (b) Vlak, J. M.; Rohrmann, G. F. In Viral Insecticides for Biological Control; Maramorosch, K., Sherman, K. E., Eds.; Academic Press: Orlando, FL, 1985; p 489.
51. (c) Kozlov, E. A.; Levitina, T. L.; Gusak, N. M. In The Molecular Biology of Baculoviruses; Doerfler, W., Bihm, P., Eds.; Springer-Verlag Berlin: Heidelberg, Germany, 1986; Vol. 131, p 135.
52. (d) Smith, I. R. L.; van Beek, N. A. M.; Podgwaite, J. D.; Wood, H. A. Gene 1988, 71, 97.
53. (e) Chang, M. T.; Lanner-Herrera, C.; Fikes, M. J. Invert. Path. 1989, 53, 241.
54. (f) McCarthy, W. J.; Liu, S. J. Invert. Path. 1976, 28, 57.
55. Circular dichroism measurements of native polyhedrin and polyhedrin in 6 M urea revealed that the native protein possessed a number of elements of secondary structure which were altered upon urea treatment.
56. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
57. Schelme, R. R. Acta Chem. Scand. 1966, 20, 1182.
58. Chhabra, S. C.; Gupta, S. R.; Sharma, N. D. Ind. J. Chem. Sect. B 1978, 16, 1079.
59. Gill, S. C.; von Hippel, P. H. Anal. Biochem. 1989, 182, 319.