Pumiliotoxin 251D

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Pumiliotoxin 251D
IUPAC name

(8R,8aS)-8-methyl-6-[(2R)-2-methylhexylidene]-1,2,3,5,7,8a-hexahydroindolizine-8-ol

Other names

Pumiliotoxin 251D

Identifiers
CAS number 73376-35-9 N
PubChem 6440480
ChemSpider 4944741 N
ChEBI CHEBI:35596 YesY
ChEMBL CHEMBL358960 N
Jmol-3D images {{#if:O[C@]1(CC(=C\[C@H](C)CCCC)\CN2[C@H]1CCC2)C|Image 1
Properties
Molecular formula C16H29NO
Molar mass 251.41 g mol−1
Hazards
Main hazards Toxic
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Pumiliotoxin 251D is one of the toxins found in the skin of poison frogs from the Dendrobates, Epipedobates, Minyobates, and Phyllobates genera[1][2] and toads from the Melanophryniscus genus.[3][4] It is not manufactured by the amphibians, but absorbed through their insect-rich diet.[5][6] It is extremely toxic to mosquitoes.[7]

Pumiliotoxin 251D is a powerful toxin with several mechanisms of action, including blocking sodium and potassium channels in cells,[8] and inhibiting calcium-dependent ATPase.[9][10]

Some poison frogs have the ability to convert pumiliotoxin 251D into allopumiliotoxin 267A, a more potent variant of the toxin.[11]

References

  1. ↑ 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
  2. ↑ 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
  3. ↑ 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
  4. ↑ 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
  5. ↑ 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
  6. ↑ 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
  7. ↑ 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
  8. ↑ 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
  9. ↑ 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
  10. ↑ 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
  11. ↑ 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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Mechanisms
Endotoxin
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Invertebrates
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