Isolation of funiferine dimethiodide and oblongine from Tiliacora funifera

Phytochemistry
1980.0

Abstract

In previous papers [1-5] we have reported the isolation of various dimeric benzylisoquinoline alkaloids from the roots and leaves of Tiliacora funifera Engl. ex Diels (Menispermaceae). In this paper we wish to present the isolation and identification of funiferine dimethiodide (2) and the novel quaternary benzylisoquinoline monomer oblongine (3) from the water-soluble alkaloid fraction of an extract of the roots of T. funifera. The identity of funiferine dimethiodide (2) was established by a comparison of its physical and spectral properties with those of funiferine (1). The identity was confirmed by direct comparison of the properties of the isolated 2 with those of a specimen prepared by treating funiferine (1) with methyl iodide in acetone. The 'H NMR and MS of oblongine (3) suggested that it was a quaternary benzylisoquinoline alkaloid of the petaline type (4) [6]. That the isolated compound was oblongine (3) was indicated by a comparison of its spectral data with those published for oblongine (3) [7,8]. The identity was confirmed by a direct comparison of the properties of the isolated compound with a synthetic racemic sample prepared by an unambiguous route [8]. Funiferine dimethiodide (2) is a new natural product that, to our knowledge, has not been reported previously. This is also the first report of a naturally-occurring quaternary bisbenzylisoquinoline biphenyl alkaloid. Funiferine dimethiodide (2) has previously been shown to be a slightly more potent muscle-relaxing agent than (+)-tubocurarine chloride [9]. Oblongine (3) has been found previously in Berberis oblonga [7] and another Tiliacora species, T. dinklagei [7].

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