Jervanine alkaloids

This survey on steroidal alkaloids of the Veratrum and Solanum family isolated between 1974 and 2014 includes 187 compounds and 197 references. New developments in the chemistry and biology of this family of natural products with a special focus on the medicinal relevance of the jervanine alkaloid cyclopamine are discussed. 

The crystal structure of 3-O-acetylveramarine (30) has been reported.63 Pseudojervine, veratrosine, veratramine, jervine, and a new alkaloid, verdine, have been isolated from V. dahuricum. It was suggested that the new alkaloid possesses the jervanine skeleton.64 Underground parts of V. nigrum have yielded... 

In agreement with the lUPAC Corrected Tentative Rules 7) for Steroid Nomenclature the Verairum alkaloids are classified in the jervanine (1), veratranine (2), cevanine (3), and solanidanine (4) groups. 

In accordance with the nomenclature in this chapter the alkaloids veratrobasine, jervine, 11-deoxojervine (identical with cyclopamine), veratramine, verarine and the glycoalkaloids veratrosine, pseudo-jervine, and cycloposine belong to the bases of jervanine and veratra-nine type. 

A synthetic approach to the alkaloids of C-nor-D-homo steroidal skeleton (veratramine, jervanine, and cevanine type) has been examined by Huffman and associates (57). They attempted to prepare compounds 75 and 76 from the exocyclic olefin 77. 

Acetate [1- C] was incorporated into alkaloids of the solanidanine, jervanine, veratranine, and cevanine groups. Nonradioactive 11-deoxo-jervine inhibited the incorporation of acetate [l- - C] into jervine. The biosynthetic activity of veratramine was affected by the concentration of jervine in the plant organ which synthesized the steroidal alkaloids. 

C-nor-D-homo- or [14(13 2)-abeo] systems. The latter, also referred to as Solanum alkaloids, share a common ABCD steroid skeleton, i.e., six-membered C-rings and five-membered D-rings. The Veratrum alkaloids are further divided into three subgroups (see Figure 1) the jervanine, the veratramine, and the cevanine. The Solanum alkaloids on the other hand, are further divided into the solanidine and verazine subgroups (see Figure 1). 

The steroidal alkaloids of the jervanine subgroup are composed of a hexacyclic framework with a tetrahydrofuran E-ring, spiro-cormected to the C-nor-D-homo ABCD-system and fused to a piperidine F-ring (see F pre 1). 

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