A 1,4-disubstituted quinolizidine from a Madagascan mantelline frog (Mantella).
A major alkaloid, 217A, in skin extracts of a mantelline frog (Mantella baroni) was isolated by HPLC and the structure defined by 1H-NMR spectral analysis as (1R,4S,10S)- or (1R,4R,10R)- 1-methyl-4-(Z)-(1-pent-2-en-4-ynyl) quinolizidine (1). Four other alkaloids-207I (2), 231A (3), 233A (4), and 235E' (5)-detected in frog skin extracts are proposed to be 1,4-disubstituted quinolizidines based on diagnostic mass and FTIR spectra.
Jain
P
P
Laboratory of Bioorganic Chemistry, National Institute of Diabetes, and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892-0820, USA.
Garraffo
H M
HM
Yeh
H J
HJ
Spande
T F
TF
Daly
J W
JW
Andriamaharavo
N R
NR
Andriantsiferana
M
M
D000818:Animals; D001001:Anura / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D011807:Quinolizines / Q000737:chemistry* / Q000302:isolation & purification; D012867:Skin / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared
C103982:1-methyl-4-(1-pent-2-en-4-ynyl)quinolizidine; D011807:Quinolizines