Pumiliotoxin_251D Knowpia

Pumiliotoxin 251D
Nombre IUPAC
	(8R,8aS)-8-methyl-6-[(2R)-2-methylhexylidene]-1,2,3,5,7,8a-hexahydroindolizine-8-ol
General
Otros nombres	Pumiliotoxin 251D
Fórmula estructural
Fórmula molecular	C; 16H29NO
Identificadores
Número CAS	73376-35-9
ChEBI	35596
ChEMBL	358960
ChemSpider	4944741
PubChem	6440480
UNII	P2LPB87CKN
	SMILES O[C@]1(CC(=C\[C@H](C)CCCC)\CN2[C@H]1CCC2)C
	InChI InChI=1S/C16H29NO/c1-4-5-7-13(2)10-14-11-16(3,18)15-8-6-9-17(15)12-14/h10,13,15,18H,4-9,11-12H2,1-3H3/b14-10-/t13-,15+,16+/m1/s1; Key: OKTQTXDNHCOLHT-AJKPHIATSA-N
Propiedades físicas
Masa molar	251,41 g/mol
	Valores en el SI y en condiciones estándar; (25 ℃ y 1 atm), salvo que se indique lo contrario.
	[editar datos en Wikidata]

Pumiliotoxin 251D es una de las toxinas que se encuentran en la piel de las ranas venenosas de los géneros Dendrobates, Epipedobates, Minyobates, y Phyllobates^[2]^[3] y los sapos del género Melanophryniscus.^[4]^[5] No es fabricada por los anfibios, pero lo absorben a través de la dieta de rica en insectos.^[6]^[7] Es extremadamente tóxico para los mosquitos.^[8]

Pumiliotoxin 251D es una toxina potente con varios mecanismos de acción, incluyendo el bloqueo de los canales de sodio y de potasio en las células,^[9] y la inhibición de la bomba de calcio del retículo sarcoplasmático.^[10]^[11]

Algunos venenos de las ranas tienen la posibilidad de convertir pumiliotoxin 251D en allopumiliotoxin 267A, una variante de toxina más potente.^[12]

Referencias

↑ Número CAS
↑ Edwards MW, Daly JW, Myers CW. Alkaloids from a panamanian poison frog, Dendrobates speciosus: identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products. 1988 Nov-Dec;51(6):1188-97. PMID 3236011
↑ Mortari MR, Schwartz EN, Schwartz CA, Pires OR Jr, Santos MM, Bloch C Jr, Sebben A. Main alkaloids from the Brazilian dendrobatidae frog Epipedobates flavopictus: pumiliotoxin 251D, histrionicotoxin and decahydroquinolines. Toxicon. 2004 Mar 1;43(3):303-10. PMID 15033329
↑ Mebs D, Pogoda W, Maneyro R, Kwet A. Studies on the poisonous skin secretion of individual red bellied toads, Melanophryniscus montevidensis (Anura, Bufonidae), from Uruguay. Toxicon. 2005 Nov;46(6):641-50. PMID 16157358
↑ Mebs D, Maneyro R, Pogoda W. Further studies on pumiliotoxin 251D and hydroquinone content of the skin secretion of Melanophryniscus species (Anura, Bufonidae) from Uruguay. Toxicon. 2007 Jul;50(1):166-9. PMID 17433395
↑ Saporito RA, Garraffo HM, Donnelly MA, Edwards AL, Longino JT, Daly JW. Formicine ants: An arthropod source for the pumiliotoxin alkaloids of dendrobatid poison frogs. Proceedings of the National Academy of Sciences USA. 2004 May 25;101(21):8045-50. doi 10.1073/pnas.0402365101 PMID 15128938
↑ Takada W, Sakata T, Shimano S, Enami Y, Mori N, Nishida R, Kuwahara Y. Scheloribatid mites as the source of pumiliotoxins in dendrobatid frogs. Journal of Chemical Ecology. 2005 Oct;31(10):2403-15. PMID 16195851
↑ Weldon PJ, Kramer M, Gordon S, Spande TF, Daly JW. A common pumiliotoxin from poison frogs exhibits enantioselective toxicity against mosquitoes. Proceedings of the National Academy of Sciences USA. 2006 Nov 21;103(47):17818-21. PMID 17095598
↑ Vandendriessche T, Abdel-Mottaleb Y, Maertens C, Cuypers E, Sudau A, Nubbemeyer U, Mebs D, Tytgat J. Modulation of voltage-gated Na+ and K+ channels by pumiliotoxin 251D: a "joint venture" alkaloid from arthropods and amphibians. Toxicon. 2008 Mar 1;51(3):334-44. PMID 18061227
↑ Tamburini R, Albuquerque EX, Daly JW, Kauffman FC. Inhibition of calcium-dependent ATPase from sarcoplasmic reticulum by a new class of indolizidine alkaloids, pumiliotoxins A, B, and 251D. Journal of Neurochemistry. 1981 Sep;37(3):775-80. PMID 6456330
↑ Daly JW, McNeal ET, Overman LE, Ellison DH. A new class of cardiotonic agents: structure-activity correlations for natural and synthetic analogues of the alkaloid A new class of A new class of cardiotonic agents: structure-activity correlations for natural and synthetic analogues of the alkaloid pumiliotoxin B (8-hydroxy-8-methyl-6-alkylidene-1-azabicyclo[4.3.0]nonanes). Journal of Medicinal Chemistry. 1985 Apr;28(4):482-6. PMID 3981541
↑ Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences USA. 2003 Sep 16;100(19):11092-7. PMID 12960405

Enlaces externos

Esta obra contiene una traducción derivada de «Pumiliotoxin 251D» de Wikipedia en inglés, publicada por sus editores bajo la Licencia de documentación libre de GNU y la Licencia Creative Commons Atribución-CompartirIgual 4.0 Internacional.

Datos: Q1241582

[1] Número CAS

[2] Edwards MW, Daly JW, Myers CW. Alkaloids from a panamanian poison frog, Dendrobates speciosus: identification of pumiliotoxin-A and allopumiliotoxin class alkaloids, 3,5-disubstituted indolizidines, 5-substituted 8-methylindolizidines, and a 2-methyl-6-nonyl-4-hydroxypiperidine. Journal of Natural Products. 1988 Nov-Dec;51(6):1188-97. PMID 3236011

[3] Mortari MR, Schwartz EN, Schwartz CA, Pires OR Jr, Santos MM, Bloch C Jr, Sebben A. Main alkaloids from the Brazilian dendrobatidae frog Epipedobates flavopictus: pumiliotoxin 251D, histrionicotoxin and decahydroquinolines. Toxicon. 2004 Mar 1;43(3):303-10. PMID 15033329

[4] Mebs D, Pogoda W, Maneyro R, Kwet A. Studies on the poisonous skin secretion of individual red bellied toads, Melanophryniscus montevidensis (Anura, Bufonidae), from Uruguay. Toxicon. 2005 Nov;46(6):641-50. PMID 16157358

[5] Mebs D, Maneyro R, Pogoda W. Further studies on pumiliotoxin 251D and hydroquinone content of the skin secretion of Melanophryniscus species (Anura, Bufonidae) from Uruguay. Toxicon. 2007 Jul;50(1):166-9. PMID 17433395

[6] Saporito RA, Garraffo HM, Donnelly MA, Edwards AL, Longino JT, Daly JW. Formicine ants: An arthropod source for the pumiliotoxin alkaloids of dendrobatid poison frogs. Proceedings of the National Academy of Sciences USA. 2004 May 25;101(21):8045-50. doi 10.1073/pnas.0402365101 PMID 15128938

[7] Takada W, Sakata T, Shimano S, Enami Y, Mori N, Nishida R, Kuwahara Y. Scheloribatid mites as the source of pumiliotoxins in dendrobatid frogs. Journal of Chemical Ecology. 2005 Oct;31(10):2403-15. PMID 16195851

[8] Weldon PJ, Kramer M, Gordon S, Spande TF, Daly JW. A common pumiliotoxin from poison frogs exhibits enantioselective toxicity against mosquitoes. Proceedings of the National Academy of Sciences USA. 2006 Nov 21;103(47):17818-21. PMID 17095598

[9] Vandendriessche T, Abdel-Mottaleb Y, Maertens C, Cuypers E, Sudau A, Nubbemeyer U, Mebs D, Tytgat J. Modulation of voltage-gated Na+ and K+ channels by pumiliotoxin 251D: a "joint venture" alkaloid from arthropods and amphibians. Toxicon. 2008 Mar 1;51(3):334-44. PMID 18061227

[10] Tamburini R, Albuquerque EX, Daly JW, Kauffman FC. Inhibition of calcium-dependent ATPase from sarcoplasmic reticulum by a new class of indolizidine alkaloids, pumiliotoxins A, B, and 251D. Journal of Neurochemistry. 1981 Sep;37(3):775-80. PMID 6456330

[11] Daly JW, McNeal ET, Overman LE, Ellison DH. A new class of cardiotonic agents: structure-activity correlations for natural and synthetic analogues of the alkaloid A new class of A new class of cardiotonic agents: structure-activity correlations for natural and synthetic analogues of the alkaloid pumiliotoxin B (8-hydroxy-8-methyl-6-alkylidene-1-azabicyclo[4.3.0]nonanes). Journal of Medicinal Chemistry. 1985 Apr;28(4):482-6. PMID 3981541

[12] Daly JW, Garraffo HM, Spande TF, Clark VC, Ma J, Ziffer H, Cover JF Jr. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates. Proceedings of the National Academy of Sciences USA. 2003 Sep 16;100(19):11092-7. PMID 12960405

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Summary

Referencias

Enlaces externos