A phytochemical study of Achlys triphylla (Smith) DC., (Berberidaceae) Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/ff365830q

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  • Achlys triphylla, a member of a medicinally active family containing alkaloids, was examined phytochemically to determine its possible value as a source of medicinal agents. Pharmacological testing of the crude ethanol extract exhibited a competitive inhibition of acetylcholine and histamine. Purification of alkaloid 'A' from the crude ethanol extract and subsequent pharmacological testing showed a lack of any biological activity. The alkaloid responded to typical alkaloid reagents and was isolated by means of alumina column chromatography. Preliminary data indicated that the alkaloid's identity was magnoflorine, a quaternary alkaloid commonly occurring in the plants of this family. However, its IR spectrum was different from that of magnoflorine and it could be precipitated from its acidic solution by ammonium hydroxide. Similarly, its iodide salt could not be prepared by the method commonly used for preparing the derivative for quaternary bases. The data suggested the alkaloid may be the tertiary analog of magnoflorine, namely, corytuberine. Co-chromatography and the UV spectrum of alkaloid 'A' and authentic corytuberine showed that the two compounds were not identical. The empirical formula C₁₈H₁₉O₄N was determined for alkaloid 'A' (melting point 243-5°C. decomp.) from elemental analysis and available spectral data. The presence of the simple quaternary base, choline, in the ethanol extract was noted by a characteristic purple coloration with Dragendorff's reagent. This simple base was not isolated, but its identity was established by means of extensive co-spotting experiments. Four different TLC developing systems (three acidic and one alkaline) and four different visualizing reagents were used to identify the choline spots. A carbohydrate was isolated from the ethanol extract. Its identity was concluded to be sucrose from its melting point, its behavior on acidic and enzymatic hydrolysis, and the melting points of its osazone and octa-acetate derivatives. The commonly occurring phytosterol, β-sitosterol, was isolated from the roots and rhizomes. Melting point, mixed melting point, IR spectra, and co-chromatography in three solvent systems confirmed its identity.
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