Four dimeric aporphine-containing alkaloids from Thalictrum fauriei.
Four dimeric alkaloids (1-4) containing an aporphine unit and representing unique structural features were obtained from Thalictrum fauriei and were characterized by spectral and chemical methods. Fauripavine (1), with a munitagine pavine unit, is the first such dimer with an aporphine C-1 diphenyl ether connection; although fauridine (2), also the first of its class, has codamine, a benzyl tetrahydroisoquinoline, linked at the same position. Faurithaline (3) and its 3-methoxy analogue 4, both with reticuline, a benzyl tetrahydroisoquinoline as the second unit, are the first dimers with the diphenyl ether linkage at C-8 of an aporphine oxygenated at C-10 and C-11. Oconovine (8) was converted to 8-hydroxy-O-methyloconovine (12) to determine the effect of oxygenation at C-8 on the proton chemical shift of the C-7 hydrogens in a study to support the C-8 ether linkage of alkaloids 3 and 4. All the alkaloids have the S-configuration at their asymmetric centers as established from their CD spectra when compared with those of model compounds.
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210-1291, USA.
S S
SS
Lee
R W
RW
Doskotch
D000470:Alkaloids / Q000737:chemistry*; D001060:Aporphines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000470:Alkaloids; D001060:Aporphines; D010936:Plant Extracts