Allopumiliotoxin 267A
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Preferred IUPAC name (6E,7R,8R,8aS)-8-Methyl-6-[(2R)-2-methylhexylidene]octahydroindolizine-7,8-diol | |
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Properties | |
Chemical formula | C16H29NO2 |
Molar mass | 267.413 g·mol−1 |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | Highly toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references |
Chemical compound
Allopumiliotoxin 267A is a toxin found in the skin of several poison frogs of the family Dendrobates.[1] It is a member of the class of compounds known as allopumiliotoxins. The frogs produce the toxin by modifying the original version, pumiliotoxin 251D.[2] It has been tested on mice and found to be five times more potent than the former version. It has been produced synthetically through a variety of different routes.[3][4][5][6]
See also
- Pumiliotoxin
- Allopumiliotoxin
References
- ^ Edwards, M. W.; Daly, J. W.; Myers, C. W. (1988). "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. 51 (6): 1188–97. doi:10.1021/np50060a023. PMID 3236011.
- ^ Daly, J. W.; Garraffo, H. M.; Spande, T. F.; Clark, V. C.; Ma, J.; Ziffer, H.; Cover Jr, J. F. (2003). "Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates". Proceedings of the National Academy of Sciences of the United States of America. 100 (19): 11092–7. Bibcode:2003PNAS..10011092D. doi:10.1073/pnas.1834430100. PMC 196932. PMID 12960405.
- ^ Comins, D. L.; Huang, S.; McArdle, C. L.; Ingalls, C. L. (2001). "Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: A concise asymmetric synthesis of (+)-allopumiliotoxin 267A". Organic Letters. 3 (3): 469–71. doi:10.1021/ol0069709. PMID 11428041.
- ^ Franklin, Alison S.; Overman, Larry E. (1996). "Total Syntheses of Pumiliotoxin a and Allopumiliotoxin Alkaloids. Interplay of Pharmacologically Active Natural Products and New Synthetic Methods and Strategies". Chemical Reviews. 96 (1): 505–522. doi:10.1021/cr950021p. PMID 11848762.
- ^ Tang, Xiao-Qing; Montgomery, John (2000). "Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B". Journal of the American Chemical Society. 122 (29): 6950–6954. doi:10.1021/ja001440t.
- ^ Aoyagi, Sakae; Wang, Tzu Chueh; Kibayashi, Chihiro (1993). "Highly stereoselective total syntheses of (+)-allopumiliotoxins 267A and 339A via intramolecular nickel(II)/Chromium(II)-mediated cyclization". Journal of the American Chemical Society. 115 (24): 11393–11409. doi:10.1021/ja00077a044.
- v
- t
- e
- Toxins
- cardiotoxin
- cytotoxin
- enterotoxin
- hemotoxin
- hepatotoxin
- neurotoxin
- phototoxin
toxins
Exotoxin |
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Endotoxin | |||||||||||||||||||||
Virulence factor |
- Aflatoxin
- Amatoxin (alpha-amanitin, beta-amanitin, gamma-amanitin, epsilon-amanitin)
- beta-Nitropropionic acid
- Citrinin
- Cytochalasin
- Ergotamine
- Fumonisin (Fumonisin B1, Fumonisin B2, Fumonisin B3, Fumonisin B4)
- Gliotoxin
- Ibotenic acid
- Lolitrem B
- Muscimol
- Ochratoxin
- Patulin
- Phalloidin
- Sterigmatocystin
- Trichothecene
- Vomitoxin
- Zeranol
- Zearalenone
- Amygdalin
- Anisatin
- Antiarin
- Brucine
- Chaconine
- Cicutoxin
- Coniine
- Daphnin
- Delphinine
- Divicine
- Djenkolic acid
- Falcarinol
- Gossypol
- Helenalin
- Ledol
- Linamarin
- Lotaustralin
- Mimosine
- Oenanthotoxin
- Oleandrin
- Persin
- Protoanemonin
- Pseudaconitine
- Retronecine
- Resiniferatoxin
- Scopolamine
- Solamargine
- Solanidine
- Solanine
- Solasodamine
- Solasodine
- Solasonine
- Solauricidine
- Solauricine
- Strychnine
- Swainsonine
- Tagetitoxin
- Tinyatoxin
- Tomatine
- Toxalbumin
- Tutin
toxins
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spider: | |
Mollusca: |
toxins
Fish: | |
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Amphibian: | |
Reptile/ Snake venom: |
- note: some toxins are produced by lower species and pass through intermediate species
- Category