Bisbenzylisoquinoline Alkaloids

Journal of Natural Products
1983.0

Abstract

The bisbenzylisoquinoline alkaloids are represented by approximately two hundred compounds which occur primarily in the Families Berberidaceae, Menispermaceae, Monimiaceae and Ranunculaceae (1). Although a number of reviews or books have been published concerning these alkaloids (1-14), the review of Guha et al. (1), which was published in this journal in early 1979 and reported on the literature through 1977, was the first comprehensive tabular compilation of spectral and related data for this group of alkaloids. This present review is concerned with the literature from 1978 through 1981 (Chemical Abstracts volumes 88 through 95) and is, likewise, presented principally in a tabular form. The numbers of the alkaloids and the structural type nomenclature have been retained according to the review of Guha et al. (1) in order to maintain a consistency between that review and this one. Since the publication of the Guha review, approximately thirty-eight new bisbenzylisoquinoline alkaloids have been isolated and characterized. Furthermore, structural revision for several alkaloids has occurred with additional physiochemical and spectral data becoming available for numerous other alkaloids. Each alkaloid in the tabular section is described according to its name, molecular formula, molecular weight, melting point, specific rotation, and available spectral data, the last of which may include infrared, ultraviolet, proton magnetic resonance, carbon magnetic resonance, circular dichroism and mass spectra. The numbering of the skeleton and the systematic numerical classification describing the oxygenation and dimerization patterns of the alkaloids follow the convention established by Shamma and Moniot (162). Unless otherwise stated, the ultraviolet spectra (nm, log ε), the circular dichroism spectra, and the optical rotatory dispersion spectra were obtained in methanol, the infrared spectra (cm⁻¹) in chloroform, and both the proton magnetic resonance and carbon magnetic resonance spectra in deuteriochloroform. Chemical shifts are in δ units and coupling constants in Hz. The fluorescence spectra were measured in ethanol at 285nm (φf=fluorescence quantum yield and τf/ns = fluorescence lifetime), while the phosphorescence spectra were measured in ethanol at 285nm and 77°K (φp =phosphorescence quantum yield and τp/ns = phosphorescence lifetime).

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