Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Structural Elucidation and Chemical Conversion of Amorphispironone, a Novel Spironone form Amorpha fruticosa, to Rotenoids
Hiroki TERADA, Midori KOKUMAI, Takao KONOSHIMA, Mutsuo KOZUKA, Mitsumasa HARUNA, Kazuo ITO, James R ESTES, Leping LI, Hui-Kang WANG, Kuo-Hsiung LEE
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Keywords: Amorpha fruticosa, amorphispironone, rotenoid, Leguminosae, tephrosin, deguelin
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1993 Volume 41 Issue 1 Pages 187-190

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Abstract

To search for possible antiumor promoters, we carried out an investigation of the leaves of Amorpha fruticosa L. (Leguminosae). The novel spironone type rotenoid, amorphispironone (1), isolated together with four known rotenoids, tephrosin (2), amorphigenin (3), 12a-hydroxyamorphigenin (4) and 12a-hydroxydalpanol (5). Some of these compounds were inhibitors of Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate. The structure of 1 was derermined from 2D-NMR spectral data and difference NOE experiments.Amorphispironone (1) was also converted to know rotenoids in order to confirm the proposed structure.

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