Steroid alkaloids Veratrum group

Jeger, O. and V. Prelog, Steroid alkaloids. Veratrum group, in The Alkaloids, Vol. 7 (R. H. F. Manske, ed.), 364-418, Academic Press, New York, 1960a. 

Several plants in the Liliaceae, notably the genus Veratrum (Liliaceae/Melanthiaceae), contain a remarkable group of steroidal alkaloids in which a fundamental change to the basic steroid nucleus has taken place. This change expands ring D by one carbon at the expense of ring C, which consequently becomes five-membered. 

Since the establishment of the structure of conessine (1), and the discovery of numerous steroidal amines, the theoretical and economic interest of the steroidal amines and alkaloids has stimulated very active chemical research on the plants of the Apocynaceae and Buxaceae families. The main points in this work are set out in two monographs. The present account is confined to the results obtained since 1966 and deals only with the Apocynaceae and Buxaceae families. The Solanaceae and Veratrum groups are not included. 

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. 

Occasionally, plant alkaloids of terpenoid origin are sequestered by insects. For example, larvae of many species of sawfly are chemically protected by toxic metabolites they sequester from their host plants. This includes iridoid glycosides (see Section 2.04.3) and a group of steroidal alkaloids produced by plants of the genus Veratrum, such as zygadenine (149). In some cases, sawfly larvae have been shown to further metabolize sequestered Veratrum alkaloids for example, zygadenine is derived from hydrolysis of the ester functionalities in sequestered protoveratrine A (150). ... 

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). 

Chapter 1. Steroid Alkaloids The Veratrum and Buxus Groups J. Tomko and Z. Voticky... 

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. 

The Steroid Alkaloids The Veratrum Group BY S. Mobbis KtrpcHAN and... 

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. 

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