Characterisation of alkaloids from some Australian Stephania (Menispermaceae) species.
Chemical investigations of some Stephania species native to Australia and reportedly employed by Aboriginal people as therapeutic agents, are described. The alkaloids from the forest vines Stephania bancroftii F.M. Bailey and S. aculeata F.M. Bailey (Menispermaceae) have been isolated and characterised. The major alkaloids in the tuber of the former species are (-)-tetrahydropalmatine and (-)-stephanine, whereas these are minor components in the leaves, from which a C-7 hydroxylated aporphine has been identified. The major tuber alkaloids in S. aculeata are (+)-laudanidine, and the morphinoid, (-)-amurine, whose absolute stereochemistry has been established by X-ray structural analysis of the methiodide derivative. No significant levels of alkaloids were detected in S. japonica. Complete and unambiguous 1H and 13C NMR data are presented for these alkaloids.
Blanchfield
Joanne T
JT
Department of Chemistry, School of Molecular and Microbial Sciences, The University of Queensland, Brisbane, Queensland 4072, Australia. j.blanchfield@mailbox.up.edu.au
Sands
Donald P A
DP
Kennard
Colin H L
CH
Byriel
Karl A
KA
Kitching
William
W
D000470:Alkaloids / Q000032:analysis*; D001315:Australia; D009682:Magnetic Resonance Spectroscopy; D029583:Menispermaceae / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D018515:Plant Leaves; D018547:Plant Stems / Q000737:chemistry; D035281:Plant Tubers / Q000737:chemistry; D013045:Species Specificity
D000470:Alkaloids