Veratrum VOLUMES

Many of the alkaloids from Veratrum, Zygadenus and related genera are based on the cevane structure 1. The chemistry of the Veratrum alkaloids has been reviewed from time to time both in this treatise (1-3) and elsewhere (4-6). The most recent of these articles was published in 1973, and many new compounds have been discovered since then. Recent years have seen the announcement of many X-ray crystal structure determinations on these stereochemically complex alkaloids. A total synthesis has been reported for only one of the natural products, namely, verticine (7). The work that lead to this notable achievement has been reviewed (8). The pharmacology of both the alkaloids (9-12) and their synthetic derivatives (13) has been reviewed, although not since 1977. This chapter takes a different approach from previous reviews. The chemical reactions used for structure determination and modification are first summarized, but the main part of the chapter is a series of tables which include all the known cevane derivatives, both old and new. This is intended as a reference source for future workers in the field. The literature has been covered to the end of Volume 113 of Chemical Abstracts (1990). 

The alkaloid literature has been reviewed up to the end of June 1970, but for convenience most authors have started their literature surveys from January 1969 this inaugural volume, therefore, properly represents a summary of developments in the subject during an eighteen-month period. The whole field of alkaloid chemistry has been reviewed with the exception of the steroidal alkaloids of the Solarium and Veratrum groups. It has not proved possible owing to limitations of space to include these sub-groups in the present volume, and it is therefore planned to include a review of developments in this area during a two-year period in the second volume. 

This second volume, which reviews the alkaloid literature from July 1970 to June 1971, approaches more closely the standard Specialist Periodical Report originally envisaged by the Chemical Society and adopts a form which, with minor variations, will very probably be followed in subsequent volumes. Once again the whole field of alkaloid chemistry has been reviewed, with the exception of the Steroidal Alkaloids of the Solanum and Veratrum Groups. The omission of these groups in the first volume was deliberate their inclusion in the second volume was intended, but proved to be impracticable, and we hope to remedy this omission in the third volume. It is fortunate, however, that this particular area can quite properly be discussed in a volume devoted to alkaloids or in one devoted to steroids and for a brief review of recent developments in this subject the reader is meanwhile referred to the Specialist Periodical Report on Terpenoids and Steroids, Volume One (Senior Reporter Dr. K. H. Overton). 

Bezold and Hirt (20) showed that injections of extracts of Viscum or Veratrum species induced circulatory effects (bradycardia and vasodilatation) and respiratory (apnea) effects (Bezold effect). Since these effects are absent after section of the vagus nerves, the authors concluded that Veratrum provokes its effects reflexly by stimulation of receptors located in the heart and pulmonary circulations. Many alkaloids have been isolated from Veratrum species (Volume III) and the characteristic actions of these have been described by a number of authors (21-24). 

This third volume in the series of Specialist Periodical Reports on Alkaloids comprises reviews of progress in the whole field of alkaloid chemistry for the period July 1971 to June 1972. For the first time we include a summary of recent developments in the chemistry of the Steroidal Alkaloids of the Solatium and Veratrum Groups. In this chapter, contributed by R. B. Herbert, the emphasis has properly been given to the period of review adopted for the volume as a whole, but in order to fill in the gap between existing reviews and July 1971 the salient literature references in this area from the beginning of 1970 have also been included. 

Thus, the C2 7-steroid alkaloids with C-nor-D-homo ring system, that is, with a jervane or cevane skeleton, with 18-nor-17j8-methylcholestane skeleton (23-27) or other alterations of the C27-carbon skeleton of cholestane, found in Liliaceae but not yet in Solanaceae, are not included. They are described exhaustively in other volumes of this series by Kupuchan and By (28) as well as by Tomko and Voticky (29). On the other hand, some Veratrum bases, for instance, teinemine and baikeine, belong to the 5o/amim-type alkaloids and are mentioned in this chapter. 

Philipp Heretsch and Athanassios Giannis summarize the scientific progress in the area of veratrum and solanum alkaloids. Previously, solanum and veratmm alkaloids have been covered in this series by V. Prelog and O. Jeger in Chapter 21 of Volume 3 (pubHshed in 1953) and in the Chapters 16 and 17 ofVolume 7 (1960), Klaus Schreiber in Chapter 1 and S. Morris Kupchan and Arnold W. By in Chapter 2 of Volume 10 (1968), and... 

J. Tomko and Z. Voticky in Chapter 1 of Volume 14 (1973). Most recendy, the cevane subgroup of the veratrum alkaloids has been covered by John V. Greenhill and Paul Grayshan in Chapter 4 of Volume 41 (1992). Chapter 4 of the present volume compiles newly isolated alkaloids of the solanum and veratrum groups, their chemistry including recent total syntheses, and their biological properties. 

Volume 10 in the series "The Alkaloids" edited by R.H.F. Manske appeared of which almost half was devoted to the steroid alkaloids of the Solanum and Veratrum groups. The remainder includes sections on Rrythro-phleum, lycopodium, benzyllsoquinollne. Indole and Taxus alkaloids. 

Thus, the C27-steroid alkaloids with C-nor-D-homo [14(13->-12)-abeo] ring system, that is, with a jervane (5) or cevane (6) skeleton, found in Liliaceae but until now not in Solanaceae, are not included they will be described exhaustively in another chapter of this volume by S. M. Kupchan. On the other hand, the tertiary Veratrum bases rubijervine, isorubijervine, and veralobine belong to the solanidanes and will be mentioned briefly in this chapter, but a detailed description of these alkaloids and their derivatives will also be given by S. M. Kupchan. 

During the period since the publication of Volume VII of this series, significant contributions have been made to our knowledge of the chemistry, and especially, the stereochemistry of several subgroups among the Veratrum alkaloids. 

In one respect, the order of discussion in this supplement has been modified as compared w ith Chapter 17 of Volume VII. The logical names jerveratrum and ceveratrum, proposed by Fieser and Fieser ) for the two distinct chemical groups of Veratrum alkaloids, are adopted. The jerveratrum alkamines contain onlj 1 to 3 atoms of oxygen and are found in unhydrolyzed plant extracts in part as the free alkamines and in part in... 

No new jerveratrum glycoalkaloids appear to have been isolated since the last review (Volume VII). However, Tomko and collaborators have reported isolation of pseudojervine from Veratrum album subsp. lobelianum (Bernh.) Suessenguth (9). 

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