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.
Lee
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SS
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, Ohio 43210-1291, USA.
Doskotch
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RW
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