Solatium alkaloids

In addition to tomatidine (183), the /V-acetyl derivate (185) was epimerized at C-3 to give 186, and both soladulcidine (solasodanol, 196) and dihydro-tomatidine B (201) were transformed in a similar manner, giving 197 and 203, respectively. The Solatium alkaloid demissidine (213) was not epimerized at C-3 by N. restrictus (187). 

A large number of steroidal alkaloids have been described in the literature. Recent reviews covering Solatium alkaloids [619] and the anticancer activity of solasodine glycosides [620] are available. 

Advances in the chemistry of three groups of alkaloids are reviewed in this volume. The Sceletium and Phenanthroindolizidine-Phenanthro-quinolizidine groups were previously reviewed in Volume IX of this series and a chapter on the Solatium alkaloids appeared in Volume X. The present reports deal with the considerable research activity in these areas over the intervening years. 

Thus, it may be assumed, that steroidal alkaloids, i.e., alkamines and/or glycoalkaloids, represent a common and consistent ttait in the genus Solarium. This was already assumed by Heftmann (1983) ( It is quite possible that they occur in all representatives of this genus ) and Hegnauer (1990) Solatium alkaloids are hardly absent in any species of the genus . 

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. 

Aside from the steroid alkaloids from Solatium, little work has been done on other groups of steroid alkaloids (Table XLVII). Roddick and Butcher (802) reported the isolation of tomatine from a callus culture of tomato cell suspension cultures and several other callus cell lines did not contain this glycoalkaloid. 

Chapter 2. Solatium Steroid Alkaloids Helmut Ripperger and Klaus Schreiber... 

El Sayed KA, Hamann MT, Abd El-Rahman HA, Zaghloul AM (1998) New pyrrole alkaloids from Solarium sodomaeum. 1 Nat Prod 61 848-850 Evans WC, Somanabandhu A (1977) Bases from roots of Solatium carolinense. Phytochemistry 16 1859-1860... 

Table 7.3 Steroidal alkaloids (alkamines) alphabetically listed within the different structural types For 41 out of altogether 115 compounds from Solatium spp. (113 compounds), Lycianthes biflora, and Saracha punctata (one compound each) at least one corresponding glycoalkaloid was found and structurally elucidated, i.e., for 36% of the alkamines also corresponding glycosides are known (continued)...

The huge number (422) of Solatium spp. already proven to contain steroidal alkaloids (for details on the count see Sect. 7.8.2)... 

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