[A new lupin alkaloid, (-)-leontalbinine N-oxide, in Sophora flavescens var. angustifolia seeds and its synthesis by biomimetic transformation from (+)-matrine N-oxide].
The possibility of the biomimetic transformation of (+)-matrine N-oxide, a main alkaloid in Sophora flavescens var. angustifolia, under various oxidative conditions was examined by the use of several metallic ions. When (+)-matrine N-oxide was warmed with FeSO4, or Fe(COOH)2 in MeOH-H2O at 40 degrees C, (-)-7, 11-didehydromatrine [(-)-leontalbinine], a minor alkaloid in the same plant, was obtained along with (+)-matrine. This selective formation of (-)-leontalbinine seems to be specific to the reaction of (+)-matrine N-oxide with ferrous reagents. In addition, the structure of the newly isolated minor lupin alkaloid from the seeds of S. flavescens. was determined as (-)-leontalbinine N-oxide from its spectral comparison with the authentic sample.
Sekine
T
T
Faculty of Pharmaceutical Sciences, Chiba University, Japan.
Saito
K
K
Minami
R
R
Arai
N
N
Suzuki
H
H
Koike
Y
Y
Murakoshi
I
I
D000470:Alkaloids / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry*; D003497:Cyclic N-Oxides / Q000032:analysis / Q000138:chemical synthesis*; D004365:Drugs, Chinese Herbal / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011807:Quinolizines; D012639:Seeds / Q000737:chemistry; D000093842:Matrines
D000470:Alkaloids; D003497:Cyclic N-Oxides; D004365:Drugs, Chinese Herbal; D011807:Quinolizines; C080544:leontalbinine N-oxide; C037573:oxymatrine; D000093842:Matrines