New classes of amidine, indolizidine and quinolizidine alkaloids from a poison-frog, dendrobates pumilio (dendrobatidae)
✍ Scribed by T. Tokuyama; N. Nishimori; A. Shimada; M.W. Edwards; J.W. Daly
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 619 KB
- Volume
- 43
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Skin extracts From the Panamanian poison-Frog Dendrobates pumilio afforded three major alkaloids of known structure, namely the 6-ylidene-8-hydroxy-8-methylindollzidines pumillotoxin A and B and the cis-decahydroqulnoline pumlliotoxln C. Other alkaloids include congeners 307F and 321 of pumillotoxln A, allopumillotoxins 267A. 3238 and 339A. a 7-alkylidene-9-hydroxy-9-methylqulnolizldlne 2230, homologous to the pumillotoxin-A class of dendrobatid alkaloids, a 5-alkynyl-8-methyllndolizidine 205A. a 5-alkenyl-a-methylindolizidlne 2358, a 3,6,8-trimethyl-12-azatrlcycloC7.2.l.O5~~2l-2-dodecene 2058. a 6hydroxy analog (211A) of the cls-decahydroqulnollne pumlllotoxin C, and three trlcycllc amldines 222, 236, 252. The allopumiliotoxins 3238 and 339A are 7-axial-hydroxy congeners of pumiliotoxin A and B, respectively. and allopumiliotoxln 267A is the 7-axial-hydroxy analog of pumiliotoxin 251D. Structures are proposed for 307F. 321, 223G, 205A. 235B. 2058. 211A. 222. 236 and 252, based primarily on mass and nuclear magnetic resonance spectral analysis.