Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates

Proceedings of the National Academy of Sciences of the United States of America

Volumn 100, Issue 19, 2003, Pages 11092-11097

  Daly, John W ^a   Garraffo, H Martin ^a   Spande, Thomas F ^a   Clark, Valerie C ^a,c   Ma, Jingyuan ^a,d   Ziffer, Herman ^a   Cover Jr , John F ^b  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b National Aquarium in Baltimore   (United States)

^c Och Spine at New York Presbyterian Hospitals   (United States)

^d Metabolex Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ALLOPUMILIOTOXIN; ANTICONVULSIVE AGENT; CARBAMAZEPINE; COCCINELLINE; CONVULSANT AGENT; DECAHYDROQUINOLINE DERIVATIVE; DIAZEPAM; DIZOCILPINE; OXYGENASE; PHENOBARBITAL; PROLINE DERIVATIVE; PUMILIOTOXIN; PUMILIOTOXIN 7 HYDROXYLASE; SPIROPYRROLIZIDINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTHROPOD; ARTICLE; CONTROLLED STUDY; CONVULSION; DENDROBATES; DENDROBATES AURATUS; DENDROBATID POISON FROG; DIET; DRUG ACCUMULATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; EPIPEDOBATES; EVOLUTION; FROG; GENUS; HYDROXYLATION; HYPERALGESIA; INGESTION; ISOMER; MALE; MOUSE; NONHUMAN; PHYLLOBATES; PREDATOR; PRIORITY JOURNAL; SKIN; SPECIES; STEREOCHEMISTRY;

ANIMALS; ANURA; HYDROXYLATION; MIXED FUNCTION OXYGENASES; STEREOISOMERISM;

ANIMALIA; ANURA; ARTHROPODA; DENDROBATES; DENDROBATES AURATUS; DENDROBATIDAE; EPIPEDOBATES; PHYLLOBATES;

EID: 0141813794     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.1834430100     Document Type: Article

References (45)

1. Daly, J. W., Myers, C. W. & Whittaker, N. (1987) Toxicon 25, 1023-1095.
2. Daly, J. W., Brown, C. B., Mensah-Dwumah, M. & Myers, C. W. (1978) Toxicon 16, 163-188.
3. Daly, J. W., Garraffo, H. M. & Spande, T. F. (1999) in Alkaloids: Chemical and Biological Perspectives, ed. Pelletier, S. W. (Pergamon, New York), pp. 1-161.
4. Daly, J. W., Myers, C. W., Warnick, J. E. & Albuquerque, E. X. (1980) Science 208, 1383-1385.
5. Daly, J. W., Secunda, S. I., Garraffo, H. M., Spande, T. F., Wisnieski, A., Nishihara, C. & Cover, J. F., Jr. (1992) Toxicon 30, 887-898.
6. Daly, J. W., Secunda, S. I., Garraffo, H. M., Spande, T. F., Wisnieski, A. & Cover, J. F., Jr. (1994) Toxicon 32, 657-663.
7. Daly, J. W., Garraffo, H. M., Spande, T. F., Jaramillo, C. & Rand, S. (1994) J. Chem. Ecol. 20, 943-955.
8. Myers, C. W. & Daly, J. W. (1976) Bull. Am. Mus. Nat. Hist. 157, 173-262.
9. Myers, C. W., Daly, J. W. & Malkin, B. (1978) Bull. Amer. Mus. Nat. Hist. 161, 307-366.
10. Garraffo, H. M., Caceres, J., Daly, J. W., Spande, T. F., Andriamaharavo, N. R. & Andriantsiferana, M. (1993) J. Nat. Prod. 56, 1016-1038.
11. Daly, J. W., Andriamaharavo, N. R., Andriantsiferana, M. & Myers, C. W. (1996) Am. Mus. Novitates 3177, 1-34.
12. Garraffo, H. M., Spande, T. F., Daly, J. W., Baldessari, A. & Gros, E. G. (1993) J. Nat. Prod. 56, 357-373.
13. Daly, J. W., Garraffo, H. M., Pannell, L. K. & Spande, T. F. (1990) J. Nat. Prod. 53, 407-421.
14. Daly, J. W., Garraffo, H. M., Hall, G. S. E. & Cover, J. F., Jr. (1997) Toxicon 35, 1131-1135.
15. Smith, B. P., Tyler, M. J., Kaneko, T., Garraffo, H. M., Spande, T. F. & Daly, J. W. (2002) J. Nat. Prod. 65, 439-447.
16. Daly, J. W., Garraffo, H. M., Jain, P., Spande, T. F., Snelling, R. R., Jaramillo, C. & Rand, A. S. (2000) J. Chem. Ecol. 26, 73-85.
17. Daly, J. W., Kaneko, T., Wilham, J., Garraffo, H. M., Spande, T. F., Espinosa, A. & Donnelly, M. A. (2002) Proc. Natl. Acad. Sci. USA 99, 13996-14001.
18. McCloskey, P. J. & Schultz, A. G. (1988) J. Org. Chem. 53, 1380-1383.
19. Overman, L. E. & Bell, K. L. (1981) J. Am. Chem. Soc. 103, 1851-1853.
20. Overman, L. E., Bell, K. L. & Ito, F. (1984) J. Am. Chem. Soc. 106, 4192-4201.
21. Caderas, C., Lett, R., Overman, L. E., Rabinowitz, M. H., Robinson, L. A., Sharp, M. J. & Zablocki, J. (1996) J. Am. Chem. Soc. 118, 9073-9083.
22. Barger, T. M., Lett, R. M., Johnson, P. L., Hunter, J. E., Chang, C. P., Pernich, D. J., Sabol, M. R. & Dick, M. R. (1995) J. Agric. Food Chem. 43, 1044-1051.
23. Daly, J. W. (1998) J. Nat. Prod. 61, 162-172.
24. Webb, G. A. (1995) Herpetofauna 25, 36-44.
25. Jones, T. H., Gorman, J. S. T., Snelling, R. R., DeLabie, H. C., Blum, M. S., Garraffo, H. M., Jain, P., Daly, J. W. & Spande, T. F. (1999) J. Chem. Ecol. 25, 1179-1193.
26. Garraffo, H. M., Jain, P., Spande, T. F., Daly, J. W., Jones, T. H., Smith, L. J. & Zottig, V. E. (2001) J. Nat. Prod. 64, 421-427.
27. Silverstone, P. A. (1975) Nat. Hist. Mus. Los Angeles County Sci. Bull. 27, 1-55.
28. Caldwell, J. P. & Myers, C. W. (1990) Am. Mus. Novitates 2988, 1-21.
29. Myers, C. W., Daly, J. W. & Martinez, V. (1984) Am. Mus. Novitates 2783, 1-20.
30. Myers, C. W. (1987) Papéis Avulsos Zool. S. Paulo 36, 301-306.
31. Vences, M., Kosuch, J., Lötters, S., Widmer, A., Jungfor, K.-H., Köhler, J. & Veith, M. (2000) Mol. Phylogenet. Evol. 15, 34-40.
32. Clough, M. & Summers, K. (2000) Biol. J. Linnean Soc. 70, 515-540.
33. Jungfer, K.-H., Weygoldt, P. & Jurasko, N. (1996) Herpetofauna 18, 17-26.
34. Jungfer, K.-H., Lötters, S. & Jörgens, D. (2000) Herpetofauna 22, 11-18.
35. Daly, J. W., Tokuyama, T., Fujiwara, T., Highet, R. J. & Karle, I. L. (1980) J. Am. Chem. Soc. 102, 830-836.
36. Simon, M. P. & Toft, C. A. (1991) Oikos 61, 263-278.
37. Caldwell, J. P. (1996) J. Zool. 240, 75-101.
38. Donnelly, M. A. (1991) Copeia 3, 723-730.
39. Toft, C. A. (1995) Herpetologica 51, 202-216.
40. Gusovsky, F., Rossignol, D. P., McNeal, E. T. & Daly, J. W. (1988) Proc. Natl. Acad. Sci. USA 85, 1272-1276.
41. Gusovsky, F., Padgett, W. L., Creveling, C. R. & Daly, J. W. (1992) Mol. Pharmacol. 42, 1104-1108.
42. Daly, J. W., McNeal, E. T., Overman, L. E. & Ellison, D. H. (1985) J. Med. Chem. 28, 482-486.
43. Daly, J. W., Gusovsky, F., McNeal, E. T., Secunda, S. S., Bell, M., Creveling, C. R., Nishizawa, Y., Overman, L. E., Sharp, M. J. & Rossignol, D. P. (1990) Biochem. Pharmacol. 40, 315-326.
44. Daly, J. W., McNeal, E., Gusovsky, F., Ito, F. & Overman, L. E. (1988) J. Med. Chem. 31, 477-480.
45. McNamara, J. O. (1995) in Goodman and Gilman's The Pharmacological Basis of Therapeutics, eds. Hardman, J. G., Gilman, A. G. & Limbird, L. E. (McGraw-Hill, New York), pp. 461-486.