Thaliporphinemethine: A New Phenanthrene Alkaloid from Illigera pentaphylla

Journal of Natural Products
1985.0

Abstract

We have presently studied the alkaloidal content of Illigera pentaphylla Welw. collected in southwestern Nigeria, from which we have isolated the new amorphous phenanthrene alkaloid, thaliporphinemethine (1), C21H25NO4. The 1H-nmr spectrum of thaliporphinemethine in CDCl3 solution at 360 MHz showed three aromatic proton singlets (including one at δ 9.27 representing H-5), three methoxyl singlets at δ 3.92, 4.04, and 4.08, a hydroxyl function at C-4 (as a methoxyl group there would adsorb upfield in δ 3.78-3.90), two doublets at δ 7.50 and 7.75 due to H-9 and H-10, and a six-proton singlet at δ 2.41 denoting a dimethylamino group. A strong uv bathochromic shift in basic solution confirmed the presence of a phenolic function. The mass spectrum exhibited a small molecular ion m/z 355 and a base peak m/z 58 due to the dimethyliminium cation. Fourteen known alkaloids were also found, eight of which were aporphines (including (+)-actinodaphnine, (+)-lindcarpine, (+)-boldine, (+)-norboldine, (+)-N-methylindcarpine, (+)-laurotetanine, (+)-nordicentrine, and (+)-laurelliptine) while the remaining six were oxoaporphines (including lysicamine, oxonantenine, oxocrebanine, dicentrinone, lanuginosine, and atheroline).

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