Alkaloids, Delphinium

Lycoctonine is also the basic, hydrolytic product of some delphinium alkaloids (pp. 694-6). 

The pharmacological activities of many more Delphinium alkaloids were studied by various authors, but not included in this article. 

Mass spectral studies have also been used more extensively. Soviet investigators at Tashkent in their mass spectral analyses of the Aconitum and Delphinium alkaloids have provided a mass spectral data base of great utility in the structure elucidation of new alkaloids with the lycoctonine skeleton. A study employing trimethylsilyl derivatives in a gas chromatograph-mass spectrometer system has also been reported. A brief review of mass spectral studies on diterpene alkaloids has appeared. ... 

Aconitum and Delphinium Alkaloids. C,-Skeleton.—Oxonitine. Wiesner and Jay have re-examined the nature of the iV-acyl group of oxonitine, the... 

Aconitum and Delphinium Alkaloids. Cjo-Skeleton.—Staphisine. The structure of staphisine has been determined using A-ray crystallographic techniques. This diterpene alkaloid dimer was first isolated from the mother liquors accumulated in the extraction of delphinine from Delphinium staphisagria in 1941. Chemical studies of this compound were hindered by its instability and by the fact that attempted degradation led to complex changes involving numerous unstable products. 

Bisbenzylisoquinoline Alkaloids by Marshall Kulka The Cularine Alkaloids by R. H. F. Manske. a-Naphthaphenanthridine Alkaloids BY R. H. F. Manske The Erythrophleum Alkaloids by G. Dalma. The Aconitum and Delphinium Alkaloids by E. S. Stern... 

This occurrence in related plant species of mixtures of chemically related alkaloids is of considerable genetic interest and has stimulated research in recent years. Another reason why Delphinium alkaloids have received increasing attention is their great toxicity which makes some of the widely... 

Since related alkaloids frequently form mixtures that are not readily separable, purification of the bases obtainable has been assured only by careful application of modem techniques. For this reason much of the early work, some of which dates back to the first half of the nineteenth century, is now of historical rather than chemical interest. The examination by many early workers of impure material caused confusion and impeded, rather than aided, later chemical work. Whilst no stmcture has been established for any alkaloid discussed in this chapter, recently tentative formulations (1,2) have been put forward as a basis for the review of the properties of atisine. In spite of the lack of stmctural formulas, a great deal of information is available about the properties and chemical behavior of the Aconitum and Delphinium alkaloids, and the close interrelation of some alkaloids of the two species has been fully elucidated. 

The general approach to the elucidation of the structure of the Aconitum and Delphinium alkaloids follows that practised in many other groups of naturally occurring complex bases. The initial characterization usually provides an empirical formula and the recognition of some, at least, of the functional groups but, some of the inadequate early work has resulted in repeated revision of several empirical formulas, and it is probably safe to assume that further work, particularly on the many minor and little studied alkaloids (see Section V), will necessitate more revisions and possibly prove the identity of some of the alkaloids mentioned in the present review, which is confined to well-characterized bases. 

Further progress has been achieved with only a few of the Aconitum and Delphinium alkaloids and is based largely on the dehydrogenation to phen-anthrene derivatives and on oxidative studies little success has attended several attempts at Hofmann degradation. The complexity of the mixtures encountered in the chemical degradation of the alkaloids limits the usefulness of a general summary and necessitates detailed discussion of... 

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