Delphinium carolinianum

Alkaloids of Delphinium carolinianum Walt.—Delcaroline (C25N41N08 amorphous m.pt of perchlorate is 160—162 °C) was the major alkaloid isolated from whole plants of D. carolinianum Walt., which is native to the south-eastern United States.50 The known bases ajaconine (103) and browniine (7) were also isolated from these plants. Acetylation of delcaroline with acetic anhydride in pyridine gave the monoacetate (104). The structure (22) for delcaroline was assigned primarily on the basis of comparison of the 13C n.m.r. spectra of (22), its monoacetate (104), browniine (7), and dictyocarpine (8). Thus delcaroline, with a hydroxyl group at C-10 and a methoxymethylene group at C-4, represents a novel substitution pattern among the known C19 diterpenoid alkaloids. 

Ajaconine, the major alkaloid of the seeds of Delphinium ajacis syn. Consolida ambigua (garden larkspur) and D. consolida, has been known since 1913 (S3). Recently, ajaconine has been isolated from the whole plants of D. virescens Nutt (84) and D. carolinianum (85), two relatively rare plants native to the southeastern United States. In 1961, Dvornik and Edwards (86) reported a full account of the structure elucidation of ajaconine as 80. 

C22H33N03 MW 359 mp 167° [ ]D -122° (EtOH) Delphinium ajacis D. consolida Consolida ambigua D. virescens D. carolinianum... 

C25H41NO7, amorphous [a]D + 25° for perchlorate (H20) Consolida ambigua, Delphinium brownii, D. carolinianum D. virescens. Chemical and spectral analysis Refs. 135-137... 

---