(−)-Epilamprolobine and its N-oxide, lupin alkaloids from Sophora tomentosa

Phytochemistry
1981.0

Abstract

From the fresh leaves of Sophora tomentosa, three new lupin alkaloids, (- )-epilamprolobine, (+ ) epilamprolobine N-oxide and 5-(3'-methoxycarbonylbutyroyl)aminomethyl-trans-quinolizidine N-oxide, have further been isolated along with ( + )-matrine, ( + )-matrine N-oxide, ( + )-sophocarpine N-oxide, ( - )-anagyrine, ( - ) baptifoline, (- )-cytisine, ( - )-N-methylcytisine, (- )-N-formylcytisine, (- )-N-acetylcytisine and ( ± )-ammodendrine. The absolute configurations of ( + )-epilamprolobine N-oxide (1R: 5R: 6S) and ( - )-epilamprolobine (5R:6S) have also been established by spectroscopic data and by comparison with synthetic (+ )-epilamprolobine (5S: 6R) derived from ( - )-lupinine (5R: 6R). ( - )-Epilamprolobine is a diastereomer of ( + )-lamprolobine (5R: 6R) in Lamprolobium fruticosum and 5-(3'-methoxycarbonylbutyroyl)aminomethyl-trans-quinolizidine N-oxide is presumed to be an artefact. A biosynthetic pathway for the formation of (- )-epilamprolobine is also proposed.

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