Pumiliotoxin 251D

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 ^Y
Jmol-3D images	Image 1
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 ^Y Key: OKTQTXDNHCOLHT-AJKPHIATSA-N ^Y InChI=1/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-AJKPHIATBP
Properties
Molecular formula	C₁₆H₂₉NO
Molar mass	251.41 g mol⁻¹
Hazards
Main hazards	Toxic
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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^[1]^[2] and toads from the Melanophryniscus families.^[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, both 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

Toxins (enterotoxin · neurotoxin · hemotoxin · cardiotoxin · phototoxin)

Bacterial
toxins

Exotoxin

Gram
positive

Bacilli	Clostridium: tetani (Tetanospasmin) · perfringens (Alpha toxin, Enterotoxin) · difficile (A, B) · botulinum (Botox) other: Anthrax toxin · Listeriolysin O

Cocci	Streptolysin · Leukocidin (Panton-Valentine leukocidin) · Staphylococcus (Staphylococcus aureus alpha/beta/delta, Exfoliatin, Toxic shock syndrome toxin, SEB)

Actinobacteria	Cord factor · Diphtheria toxin

Gram
negative

Shiga toxin · Verotoxin/shiga-like toxin (E. coli) · E. coli heat-stable enterotoxin/enterotoxin · Cholera toxin · Pertussis toxin · Pseudomonas exotoxin · Extracellular adenylate cyclase

Mechanisms

type I (Superantigen) · type II (Pore-forming toxin) · type III (AB toxin/AB5)

Endotoxin

Lipopolysaccharide (Lipid A) · Bacillus thuringiensis delta endotoxin

Virulence
factor

Clumping factor A · Fibronectin binding protein A

Mycotoxins

Aflatoxin · Amatoxin (alpha-amanitin, beta-amanitin, · Beta-nitropropionic acid · gamma-amanitin, epsilon-amanitin) · Citrinin · Cytochalasin · Ergotamine · Fumonisin (Fumonisin B1, Fumonisin B2) · Gliotoxin · Ibotenic acid · Muscimol · Ochratoxin · Patulin · Phalloidin · Sterigmatocystin · Trichothecene · Vomitoxin · Zeranol · Zearalenone

Invertebrates

scorpion: Androctonus australis hector insect toxin, Charybdotoxin, Maurotoxin, Agitoxin, Margatoxin, Slotoxin, Scyllatoxin, Hefutoxin, Lq2, Birtoxin, Bestoxin, BmKAEP, Phaiodotoxin, Imperatoxin ·
spider: Latrotoxin (Alpha-latrotoxin) · CSTX · Cupiennins · PhTx3 · Stromatoxin · Vanillotoxin · Huwentoxin
mollusca: Conotoxin · Eledoisin · Onchidal · Saxitoxin · Tetrodotoxin

Vertebrates

fish: Ciguatera · Tetrodotoxin

amphibian: (+)-Allopumiliotoxin 267A · Batrachotoxin · Bufotoxins (Arenobufagin, Bufotalin, Bufotenin · Cinobufagin, Marinobufagin) · Epibatidine · Histrionicotoxin · Pumiliotoxin 251D · Samandarin · Samandaridine · Tarichatoxin

reptile/snake venom: Bungarotoxin (Alpha-Bungarotoxin, Beta-Bungarotoxin) · Calciseptine · Taicatoxin · Calcicludine · Cardiotoxin III

note: some toxins are produced by lower species and pass through intermediate species

M: TOX

gen / txn

pto

ant

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Pumiliotoxin 251D

Pumiliotoxin 251D

References

Suggestions

Phyllobates

Encyclopedia Article