Haplaphine — A new alkaloid ofHaplophyllum perforatum

Chemistry of Natural Compounds
1986.0

Abstract

The epigeal part of the plant Haplophyllum perforatum (M.B.) Kar. et Kir. was collected by K. Taizhanov in the Dzhambul province, Kazakh SSR, close to the Kuyuk Pass in the flowering phase on June 17, 1984. The air-dry epigeal part (3100 g) was extracted by steeping with ethanol eight times. The treatment of a small amount of the evaporated ethanolic extract with 10% sulfuric acid showed that the alkaloids were not extracted by an acid solution, and the extract of the raw material, after the ethanol had been distilled off, was therefore boiled with ether. The concentrated ethereal extract was chromatographed on a column of silica gel. The first ethereal eluates yielded the lignan eudesmin, mp 105-106°C (acetone), and the later ones the alkaloid haplamine, mp 201-202°C (decomp., ethanol), with yields of 0.02 and 0.07%, respectively, on the weight of the dry raw material. The mother liquor from the haplamine, after its recrystallization, was chromatographed twice on silica gel. Ethereal eluates yielded 15 mg of a substance with mp 159-160°C (acetone), M+ 229 (mass spectrometry), which we have called haplaphine (I). Structure (la) has been proposed in [i] for the alkaloid nitraramine N-oxide (I) from the epigeal part of Nitraria schoberi, this being a hydroxylamine derivative of nitraramine (Ib). Recently [2], on the basis of an x-ray structural investigation of a crystalline salt, structure (II) was proposed for nitraramine. In the present communication we give the results of a chemical correlation of (I) with nitramine.

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