Alkaloid 223A: the first trisubstituted indolizidine from dendrobatid frogs.
The structure of alkaloid 223A (1), the first member of a new class of amphibian alkaloids, purified by HPLC from a skin extract of a Panamanian population of the frog Dendrobates pumilio Schmidt (Dendrobatidae) has been established as (5R,6S,8R,9S)- or (5S,6R,8S,9R)-6,8-diethyl-5-propylindolizidine, based on GC-MS, GC-FTIR, and 1H-NMR spectral studies. Three higher homologs of 223A, namely alkaloids 237L (2), 251M (3), and 267J (4), have been detected in other extracts, and tentative structures are proposed.
Garraffo
H M
HM
Laboratory of Bioorganic Chemistry, NIDDK, Natioinal Institutes of Health, Bethesda, Maryland 20892-0820, USA.
Jain
P
P
Spande
T F
TF
Daly
J W
JW
D000818:Animals; D001001:Anura / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D007212:Indolizines / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010176:Panama; D012867:Skin / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
C104548:6,8-diethyl-5-propylindolizidine; D007212:Indolizines