Structure of batrachotoxin, a steroidal alkaloid from the Colombian arrow poison frog, phyllobates aurotaenia, and partial synthesis of batrachotoxin and its analogs and homologs

Tokuyama, Takashi; Daly, J W; Witkop, B.

doi:10.1021/ja01042a042

Cited by 148 publications

(62 citation statements)

References 1 publication

(2 reference statements)

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“…One important difference is that the depolarization induced by grayanotoxin I is reversible after T. NARAHASHI AND I. SEYAMA washing whereas that by batrachotoxin is not. These two toxins are chemically different also; batrachotoxin is a steroid (Tokuyama, Daly & Witkop, 1969) whereas grayanotoxin I is not (Fig. 1).…”

Section: Discussionmentioning

confidence: 99%

Mechanism of nerve membrane depolarization caused by grayanotoxin I

Narahashi¹,

Seyama²

1974

The Journal of Physiology

101

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SUMMARY1. The mechanism of depolarization of squid axon membranes caused by grayanotoxin I has been studied by means of internal perfusion and voltage clamp techniques.2. The depolarization induced by either internal or external application of grayanotoxin I was reversed by decreasing the external sodium concentration from 449 to 1 mmw.3. No depolarization was observed when both external and internal media were devoid of sodium ions, indicating that the depolarization by grayanotoxin I in normal media is due to a specific increase in resting sodium permeability.4. The resting sodium permeability as measured by voltage clamp was increased to 1'31 x 106 cm/sec by internal application of 1 x 10-5 M arayanotoxin I, an increase by a factor of about 90.5. The apparent dissociation constant of internally applied grayanotoxin I in increasing the resting sodium permeability was estimated to be 412 x 10-5 M, and the toxin interacts with the membrane receptor on a one-to-one stoichiometric basis.6. Tetrodotoxin antagonized the action of grayanotoxin I in increasing the resting sodium permeability in a non-competitive manner.

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Section: Discussionmentioning

confidence: 99%

Mechanism of nerve membrane depolarization caused by grayanotoxin I

Narahashi¹,

Seyama²

1974

The Journal of Physiology

101

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“…The proportions of histrionicotoxin, dihydroisohistrionicotoxin, and another major alkaloid of unknown structure (fraction [6][7][8] in Methods) are 13:9:6. In addition, the skin of each frog contains about 1 (20). Histrionicotoxins and pumiliotoxins occur together in certain species of Dendrobates and may share a common precursor, possibly a disubstituted unsaturated piperidine (either an enamine or imine), which could undergo cyclization to either the spiro-ring system of the histrionicotoxins or the decahydroquinoline ring system of pumiliotoxin C.…”

Section: Roentgen-ray Crystallographic Analysismentioning

confidence: 99%

“…Two classes of alkaloids have been isolated from the defensive skin secretions of these frogs: batrachotoxin (Fig. 1A) from Phyllobates species is a novel steroidal alkaloid (1) and the most toxic nonprotein substance known; it selectively increases the permeability of electrogenic membranes to sodium ions and is a valuable research tool (2). Frogs of the genus Dendrobates, by contrast, contain a wide range of simpler alkaloids (3,4), which, like batrachotoxin, are irritating to buccal and mucous tissues of animals as diverse as men and snakes.…”

mentioning

confidence: 99%

Histrionicotoxins: Roentgen-Ray Analysis of the Novel Allenic and Acetylenic Spiroalkaloids Isolated from a Colombian Frog, Dendrobates histrionicus

Daly

Karle

Myers

et al. 1971

Proc. Natl. Acad. Sci. U.S.A.

Self Cite

181

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The structures and absolute configuration of two unique alkaloids isolated from the Colombian frog, Dendrobates histrionicus, have been elucidated by Roent-gen-ray (x-ray) crystallography. Histrionicotoxin is (2pll, 6S, 7pS, 8aS)-7-(cis-l-buteni-3-ynyl)-8-h-ydroxy-2-(cis-2-petiteni-4-ynlyl)-1-azaspiro[5.5] undecane, while in dihydroisohistrionicotoxin the acetylenic 2-pentenynyl side chain is replaced by an allenic 2-(3,4 pentadienyl) substituent. Dendrobates histrionicus exhibits remarkable interpopulational variations in amounts and composition of skin toxins, in behavior, and in phenotypic characters, aspects of which are illustrated in a color plate. The histrionicotoxins are the third class of alkaloids isolated from the defensive skin secretions of Neotropical (Dendrobatidae) frogs.

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“…Pitohui ͉ Ifrita ͉ Phyllobates ͉ APCI mass spectrometry ͉ dietary arthropods B atrachotoxins (BTXs) were discovered in the mid-1960s in skin extracts from a Colombian poison-dart frog (family Dendrobatidae) (1,2). The name for these unique steroidal alkaloids was derived from the Greek ''batrachos,'' meaning frog.…”

mentioning

confidence: 99%

Melyrid beetles ( Choresine ): A putative source for the batrachotoxin alkaloids found in poison-dart frogs and toxic passerine birds

Dumbacher

Wako²,

Derrickson³

et al. 2004

Proc. Natl. Acad. Sci. U.S.A.

157

124

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Batrachotoxins are neurotoxic steroidal alkaloids first isolated from a Colombian poison-dart frog and later found in certain passerine birds of New Guinea. Neither vertebrate group is thought to produce the toxins de novo, but instead they likely sequester them from dietary sources. Here we describe the presence of high levels of batrachotoxins in a little-studied group of beetles, genus Choresine (family Melyridae). These small beetles and their high toxin concentrations suggest that they might provide a toxin source for the New Guinea birds. Stomach content analyses of Pitohui birds revealed Choresine beetles in the diet, as well as numerous other small beetles and arthropods. The family Melyridae is cosmopolitan, and relatives in Colombian rain forests of South America could be the source of the batrachotoxins found in the highly toxic Phyllobates frogs of that region.Pitohui ͉ Ifrita ͉ Phyllobates ͉ APCI mass spectrometry ͉ dietary arthropods

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Structure of batrachotoxin, a steroidal alkaloid from the Colombian arrow poison frog, phyllobates aurotaenia, and partial synthesis of batrachotoxin and its analogs and homologs

Cited by 148 publications

References 1 publication

Mechanism of nerve membrane depolarization caused by grayanotoxin I

Mechanism of nerve membrane depolarization caused by grayanotoxin I

Histrionicotoxins: Roentgen-Ray Analysis of the Novel Allenic and Acetylenic Spiroalkaloids Isolated from a Colombian Frog, Dendrobates histrionicus

Melyrid beetles ( Choresine ): A putative source for the batrachotoxin alkaloids found in poison-dart frogs and toxic passerine birds

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