Abstract
The structures and absolute configuration of two unique alkaloids isolated from the Colombian frog, Dendrobates histrionicus, have been elucidated by Roentgen-ray (x-ray) crystallography. Histrionicotoxin is (2pR, 6S, 7pS, 8aS)-7-(cis-1-buten-3-ynyl)-8-hydroxy-2-(cis-2-penten-4- ynyl)-1-azaspiro[5.5] undecane, while in dihydro-isohistrionicotoxin 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 histrionico-toxins are the third class of alkaloids isolated from the defensive skin secretions of Neotropical (Dendrobatidae) frogs.
Keywords: x-ray crystallography
Full text
PDF
Images in this article
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Albuquerque E. X., Daly J. W., Witkop B. Batrachotoxin: chemistry and pharmacology. Science. 1971 Jun 4;172(3987):995–1002. doi: 10.1126/science.172.3987.995. [DOI] [PubMed] [Google Scholar]
- Bohlmann F. Biogenetische Beziehungen der natürlichen Acetylenverbindungen. Fortschr Chem Org Naturst. 1967;25:1–62. [PubMed] [Google Scholar]
- Chen K. K., Kovaríková A. Pharmacology and toxicology of toad venom. J Pharm Sci. 1967 Dec;56(12):1535–1541. doi: 10.1002/jps.2600561202. [DOI] [PubMed] [Google Scholar]
- Daly J. W., Tokuyama T., Habermehl G., Karle I., Witkop B. Froschgifte. Isolierung und Struktur von Pumiliotoxin C. Justus Liebigs Ann Chem. 1969;729:198–204. doi: 10.1002/jlac.19697290124. [DOI] [PubMed] [Google Scholar]
- Djerassi C. Applications of mass spectrometry in the steroid field. Pure Appl Chem. 1970;21(2):205–225. doi: 10.1351/pac197021020205. [DOI] [PubMed] [Google Scholar]
- Meinwald J., Meinwald Y. C., Chalmers A. M., Eisner T. Dihydromatricaria acid: acetylenic acid secreted by soldier beetle. Science. 1968 May 24;160(3830):890–892. doi: 10.1126/science.160.3830.890. [DOI] [PubMed] [Google Scholar]
- Tokuyama T., Daly J., Witkop B. The structure of batrachotoxin, a steroidal alkaloid from the Colombian arrow poison frog, Phyllobates aurotaenia, and partial synthesis of batrachotoxin and its analogs and homologs. J Am Chem Soc. 1969 Jul 2;91(14):3931–3938. doi: 10.1021/ja01042a042. [DOI] [PubMed] [Google Scholar]