ABSOLUTE STRUCTURE OF (+)-13β-HYDROXYMAMANITE, A POSSIBLE METABOLINE OF (-)-BAPTIFOLINE

Hajime KUBO; Shigeru OHMIYA; Kimio HIGASHIYAMA; Ken-ichi KAWAI; Kazuki SAITO; Isamu MURAKOSHI

doi:10.1248/cpb.42.1706

Hajime KUBO, Shigeru OHMIYA, Kimio HIGASHIYAMA, Ken-ichi KAWAI, Kazuki SAITO, Isamu MURAKOSHI

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Keywords: lupin alkaloid, quinolizidine alkaloid, Maackia amurensis, absolute configuration, X-ray analysis, (+)-13β-hydroxymamanine

JOURNAL FREE ACCESS

1994 Volume 42 Issue 8 Pages 1706-1708

DOI https://doi.org/10.1248/cpb.42.1706

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Abstract

The absolute structure of (+)-13β-hydroxymamanine (1), isolated from an alkaloidal component of Maackia amurensis (Leguminosae), has been established as (7R, 9S, 11R, 13R) by the X-ray analysis of its hydrobromide. The absolute stereochemistry of 1 is the same as that of the structure corresponding to an oxidative product derived from (-)-baptifoline (7R, 9R, 11R, 13R) coexisting in the same plant. It was strongly suggested that 1 might be an oxidative metabolite of (-)-baptifoline.

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