Bisditerpenoid Alkaloids from Delphinium staphisagria

Staphisagnine, C44H62N2O3 (resin), and staphisagrine, C43H60N2O2, m.p. 229— 231 °C, each contain an oxazolidine ring system reminiscent of atisine (108) in one unit of the dimer they differ only in the methoxy-group at C-13 in staphisagnine. 

Staphigine, C43HS8N2O3, m.p. 225—227 °C, and staphirine, C42H56N2O2, m.p. 222—225 °C, occur in extremely small amounts in the seeds of D. staphisagria, and are the C-19 lactam derivatives of staphisine and staphidine, respectively. 

In all of the reports on the structures of these novel bisditerpenoid bases the n.m.r. data are tabulated. 

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The alkaloids of Delphinium staphisagria have been reviewed. Delphidine has been shown to possess the structure (106) whilst delphirine (107) possesses the unusual C-1 hydroxy-group. Staphigine and staphirine are bisditerpenoid alkaloids which have been obtained " from D. staphisagria. Examination of D. tricorne afforded " a new alkaloid tricornine (108) which was shown to be 18-acetyl-... 

Diterpenoid Alkaloids.— The alkaloids of Delphinium staphisagria include some bisditerpenoid alkaloids such as staphidine, staphinine, and staphimine. The full paper has appeared on the structure and stereochemistry of delphisine, neoline, chasmanine, and homochasmanine. The application of n.m.r. measurements to these alkaloids has led to the revision of the structure of the alkaloid A from D. bicolor... 

Recently, a new class of diterpenoid alkaloids, known as bisditerpenoid alkaloids, has been isolated from the seeds of Delphinium staphisagria (2). The bisditerpenoid alkaloids (e.g., staphisine, iv) may be formally derived by... 

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