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

  1. John W. Daly*,
  2. Isabella Karle†,
  3. Charles W. Myers‡,
  4. Takashi Tokuyama,
  5. James A. Waters*, and
  6. Bernhard Witkop*
  1. *National Institute of Arthritis and Metabolic Diseases, NIH, Bethesda, Maryland 20014
  2. †Naval Research Laboratory, Washington, D.C.
  3. ‡American Museum of Natural History, New York, N.Y.
  4. Osaka City University, Osaka, Japan

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.

« Previous | Next Article »Table of Contents

This Article

  1. PNAS August 1, 1971 vol. 68 no. 8 1870-1875
  1. » Abstract
  2. Full Text (PDF)
About Our New Site Design >>
Link: Advanced Search

This Week's Issue

  1. November 25, 2008, 105 (47)
  1. Current Issue
  1. Alert me to new issues of PNAS

Most