Piatak, David M.
M.S. (Master of Science)
Department of Chemistry
Amorpha canescens; Plants--Analysis
The hexane extract of Amornha canes cens. roots has been studied. Pour substances were isolated and characterized. The first substance was isolated by various chromatography techniques and recrystallization. It was unresolvable by chromatographic means and resembled β-sitosterol in physical properties. It is believed to be a mixture of β-sitosterol and stigmasterol. A pentacyclic triterpene, acetylursolic acid, was isolated via recrystallization of crude chromatography fractions. Identification was made on the basis of infrared and nuclear magnetic resonance spectrometry, mass spectroscopy, and melting point values. A new rotenoid, termed amorpholone, was isolated by column and thin layer chromatography along with a known related compound called rotenonone. This latter substance was prepared from amorpholone via oxidation, Amorpholone was assigned the structure, l,2-dihydro-12-hydroxy-2-isopropeny1-8,9-dimethoxy-(1)benzopyrano(3,4-b)furo(2,3-h)-(1)benzopyran-6-one, from its physical and spectroscopic data. The synthesis of amorpholone was also accomplished from commercially available rotenone using dehydrorotenone as the key intermediate.
Flynn, Gary A., "A phytochemical investigation of Amorpha canescens" (1973). Graduate Research Theses & Dissertations. 469.
vii, 49 pages
Northern Illinois University
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