Lakshminine, a new rare oxoisoaporphine alkaloid from Sciadotenia toxifera, and structural revisions of telazoline and teladiazoline, two related oxoaporphines from Telitoxicum peruvianum and T. glaziovii.
Lakshminine (1), a novel oxoisoaporphine alkaloid possessing a C-6 amine substituent, was isolated from a basic fraction from the woody vines (collected from two bush-ropes) of Sciadotenia toxifera. This compound represents the first documented occurrence of an oxoisoaporphine from any Menispermaceae species other than Menispermum dauricum. The structures of two related aporphine alkaloids, telazoline (3) and teladiazoline (5), were revised on the basis of a comparison of their spectral data with that of lakshminine (1).
Killmer
Lew
L
Department of Analytical Sciences, GlaxoSmithKline Pharmaceuticals, 709 Swedeland Road, P.O. Box 1539, King of Prussia, Pennsylvania 19406-0939, USA.
Vogt
Frederick G
FG
Freyer
Alan J
AJ
Menachery
Mary D
MD
Adelman
Clark M
CM
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D001060:Aporphines / Q000737:chemistry / Q000302:isolation & purification*; D013058:Mass Spectrometry; D029583:Menispermaceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010568:Peru; D018547:Plant Stems
D000470:Alkaloids; D001060:Aporphines; C474697:lakshminine