ABSOLUTE CONFIGURATION OF (-) -LUSITANINE, A NEW LUPIN ALKALOID in MAACKIA SPECIES

Kazuki Saito; Takaaki Yoshino; Shi Tsai; Shigeru Ohmiya; Hajime Kubo; Hirotaka Otomasu; Isamu Murakoshi

doi:10.1248/cpb.35.1308

Kazuki Saito, Takaaki Yoshino, Shi Tsai, Shigeru Ohmiya, Hajime Kubo, Hirotaka Otomasu, Isamu Murakoshi

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Keywords: lupin alkaloid, quinolizidine alkaloid, (-) -lusitanine (1R, 6R), (+) -lusitanine (1R, 6S), absolute configuration, Maackia amurensis, Maackia tashiroi, Leguminosae, (+) -acetamidomethylquinolizidine (1R, 5R, 6R), (-) -acetamidomethylquinolizidine (1R, 5S

JOURNAL FREE ACCESS

1987 Volume 35 Issue 3 Pages 1308-1310

DOI https://doi.org/10.1248/cpb.35.1308

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Abstract

A new lupin alkaloid, (-) -lusitanine (I), has been isolated from the fresh stems of Maackia amurensis var. buergeri and M. tashiroi (Leguminosae), together with other types of the alkaloids. Its absolute configuration has also been established as (1R, 6R) -5- (E) -acetamidomethylidenequinolizidine (I) on the basis of chemical transformation into its dihydro-derivatives II ((1R, 5R, 6R) - (+) -acetamidomethylquinolizidine) and III ((1 R, 5S, 6R) - (-) -acetamidomethylquinolizidine) and of their spectral evidence.

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