Further alkaloids common to ants and frogs: Decahydroquinolines and a quinolizidine

Journal of Chemical Ecology

Volumn 25, Issue 5, 1999, Pages 1179-1193

  Jones, Tappey H ^a   Gorman, Jeffrey S T ^a   Snelling, Roy R ^b   Delabie, Jacques H C ^c   Blum, Murray S ^d   Garraffo, H Martin ^e   Jain, Poonam ^e   Daly, John W ^e   Spande, Thomas F ^e  

^a VIRGINIA MILITARY INSTITUTE   (United States)

^b NATURAL HISTORY MUSEUM OF LOS ANGELES COUNTY   (United States)

^c CEPLAC   (Brazil)

^d UNIVERSITY OF GEORGIA   (United States)

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

Author keywords

Alkaloids; Amphibians; Ants; Decahydroquinolines; Infrared spectroscopy; Mass spectrometry; Quinolizidines

Indexed keywords

ALKALOID;

ANT; ARTICLE; CHEMICAL ANALYSIS; FROG; NONHUMAN; SPECIES DIFFERENCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

AMPHIBIA; ANURA; FORMICIDAE; PICEA; SOLENOPSIS;

EID: 0032913999     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1020898229304     Document Type: Article

References (31)

1. CALDWELL, J. P. 1996. The evolution of myrmecophagy and its correlates in poison frogs (family Dendrobatidae). J. Zool (London). 240:75-101.
2. DALY, J. W. 1995. Alkaloids from frog skin: Selective probes for ion channels and nicotinic receptors. Braz. J. Med. Biol. Res. 28:1033-1042.
3. DALY, J. W., MYERS, C. W., and WHITTAKER, N. 1987. Further classification of skin alkaloids from neotropical poison frogs (Dendrobatidae), with a general survey of toxic/noxious substances in the Amphibia. Toxicon 25:1023-1095.
4. DALY, J. W., SECUNDA, S. I., GARRAFFO, H. M., SPANDE, T. F., WISNIESKI, A., NISHIHARA, C., and COVER, J. F., JR. 1992. Variability in alkaloid profiles in neotropical poison frogs (Dendrobatidae): Genetic versus environmental determinants. Toxicon 30:887-898.
5. DALY, J. W., GARRAFFO, H. M., and SPANDE, T. F. 1993. Amphibian alkaloids, pp. 185-288, in G. A. Cordell (ed.). The Alkaloids, Vol. 43. Academic Press, San Diego.
6. DALY, J. W., SECUNDA, S. I., GARRAFFO, H. M., SPANDE, T. F., WISNIESKI, A., and COVER, J. F., JR. 1994a. An uptake system for dietary alkaloids in poison frogs (Dendrobatidae). Toxicon 32:657-663.
7. DALY, J. W., GARRAFFO, H. M., SPANDE, T. F., JARAMILLO, C., and RAND, A. S. 1994b. Dietary source for skin alkaloids of poison frogs (Dendrobatidae)? J. Chem. Ecol. 20:943-955.
8. DALY, J. W., ANDRIAMAHARAVO, N. R., ANDRIANTSIFERANA, M., and MYERS, C. W. 1996. Madagascan poison frogs (Mantella) and their skin alkaloids. Am. Mus. Novit. No. 3177:1-34.
9. DALY, J. W., GARRAFFO, H. M., and MYERS, C. W. 1997. The origin of frog skin alkaloids: An enigma. Pharm. News 4:9-14.
10. DONNELLY, M. A. 1991. Feeding patterns of the strawberry poison frog, Dendrobates pumilio (Anura: Dendrobatidae). Copeia 3:723-730.
11. GARRAFFO, H. M., CACERES, J., DALY, J. W., and SPANDE, T. F. 1993a. Alkaloids in Madagascan frogs (Mantella): Pumiliotoxins, indolizidines, quinolizidines, and pyrrolizidines. J. Nat. Prod. 56:1016-1038.
12. GARRAFFO, H. M., SPANDE, T. F., DALY, J. W., BALDESSARI, A., and GROS, E. G. 1993b. Alkaloids from bufonid toads (Melanophryniscus): Decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines and quinolizidines. J. Nat. Prod. 56:357-373.
13. GARRAFFO, H. M., SIMON, L. D., DALY, J. W., SPANDE, T. F., and JONES, T. H. 1994. cis- and trans-Configurations of α, α′-disubstituted piperidines and pyrrolidines by GC-FTIR; application to decahydroquinoline stereochemistry. Tetrahedron 50:11329-11338.
14. GARRAFFO, H. M., JAIN, P., SPANDE, T. F., and DALY, J. W. 1997. Alkaloid 223A: The first trisubstituted indolizidine from dendrobatid frogs. J. Nat. Prod. 60:2-5.
15. GRIECO, P. A., and PARKER, D. T. 1988. Octahydroquinoline synthesis via immonium ion based Diels-Alder chemistry: Synthesis of (-)-8a-epi-pumiliotoxin C. J. Org. Chem. 53:3658-3662.
16. GRIERSON, D. S., ROYER, J., GUERRIER, L., and HUSSON, H.-P. 1986. Asymmetric synthesis. 6. Practical synthesis of (+)-solenopsin A. J. Org. Chem. 51:4475-4477.
17. JAIN, P., GARRAFFO, H. M., YEH, H. J. C., SPANDE, T. F., DALY, J. W., ANDRIAMAHARAVO, N. R., and ANDRIANTSIFERANA, M. 1996. A 1,4-disubstituted quinolizidine from a Madagascan mantelline frog (Mantella). J. Nat. Prod. 59:1174-1178.
18. JOHNS, S. R., LAMBERTON, J. A., SIOUMIS, A. A., and SUARES, H. 1974. The alkaloids of Poranthera corymbosa (Euphorbiacae). Aust. J. Chem. 27:2025-2034.
19. JONES, T. H., and BLUM, M. S. 1983. Arthropod alkaloids: Distribution, functions, and chemistry, pp. 33-84, in S. W. Pelletier (ed.). Alkaloids, Chemical and Biological Perspectives, Vol. 1. John Wiley & Sons, New York.
20. JONES, T. H., BLUM, M. S., and ROBERTSON, H. G. 1990. Novel dialkylpiperidines in the venom of the ant Monomorium delagoense. J. Nat. Prod. 53:429-435.
21. JONES, T. H., TORRES, J. A., SPANDE, T. F., GARRAFFO, H. M., BLUM, M. S., and SNELLING, R. R. 1996. Chemistry of venom alkaloids in some Solenopsis (Diplorhoptrum) species from Puerto Rico. J. Chem. Ecol. 22:1221-1236.
22. MACCONNELL, J. G., BLUM, M. S., and FALES, H. M. 1971. The chemistry of fire ant venom. Tetrahedron 27:1129-1139.
23. MATSUNAGA, T., KAWASAKI, I., and KANEKO, T. 1967. 2-Hydroxy-4-phenylquinolizidine. Tetrahedron Lett. 2471-2473.
24. SILVERSTONE, P. A. 1975. A revision of the poison-arrow frogs of the genus Dendrobates Wagler. Nat. Hist. Mus. Los Angeles Cty. Sci. Bull. 21:1-55.
25. SILVERSTONE, P. A. 1976. A revision of the poison-arrow frogs of the genus Phyllobates Bibron in Sagra (family Dendrobatidae). Nat. Hist. Mus. Los Angeles Cty. Sci. Bull. 27:1-53.
26. 13-CNMR in their conformational analysis. J. Nat. Prod. 65:5-21.
27. TOFT, C. A. 1980. Feeding ecology of thirteen syntopic species of anurans in a seasonal tropical environment. Oecologia 45:131-141.
28. TOFT, C. A. 1995. Evolution of diet specialization in poison-dart frogs (Dendrobatidae). Herpetologica 51:202-216.
29. TOKUYAMA, T., TSUJITA, T., SHIMADA, A., GARRAFFO, H. M., SPANDE, T. F., and DALY, J. W. 1991. Alkaloids from dendrobatid poison frogs: Further cis-decahydroquinolines and 8-methylindolizidines. Tetrahedron 47:5401-5414.
30. YASUDA, S., HANAOKA, M., and ARATA, Y. 1977. A new synthesis of (±)-7-epideoxynupharidine and (±)-1-epi-7-epi-deoxynupharidine. Heterocycles 6:391-394.
31. YU, C. K., OLDFIELD, D., and MACKLEAN, D. B. 1970. Mass spectra of decahydroquinolines. Org. Mass Sped. 4:147-155.