Delphinium ajacis

Delphinium ajacis L. From the seed of this species Keller and Volker isolated two crystalline alkaloids which they named ajacine and ajaconine. Their work was reviewed by Hunter, who reported the presence of four alkaloids, viz., ajacine, ajaconine and new alkaloids ajacinine and ajaci-noidine (amorphous). Goodson described ajacine in detail (1944) and later reported the isolation of ajaconine and three more bases distinguished as B, C and D. According to Hunter, lycoctonine (p. 686) is probably also present. 

Consolida stenocarpa Hussain and P.H. Davis Stenocarpine Delphinium ajacis Ajaconine Dihydroajaconine Delphinium albiflorum DC... 

Consolida ambigua (Delphinium ajacis)1 Prepared from 7a-hydroxyisoatisine2... 

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... 

Adonis vernalis Delphinium Consolida Delphinium Ajacis... 

Datura wrightii Bye—366 Daturicarpa elliptica Stapf-371 DeLsperma sp.—246 Delphinium ajacis L.-407 Delphinium nudicauleTort, et Gray—406,407 Delphinium virescens Nuttall—407 Derris trifoliata Loureiro-378 Desfontainia spinosa Ruiz et Pavon—398 Desfontainin spinosa Ruiz et Pavon var. 

Alkaloids of Delphinium ajacis.—Waller, Sastry, and Kinneberg have reported mass spectral studies of the alkaloidal components of the seeds of Delphinium ajacis. Delcosine (1), acetyldelcosine (2), and delsoline (3) were identified by mass spectral comparisons. 

Mass Spectral Studies of Ajaconine. Waller and Sastry have reported utilizing a gas chromatograph mass spectrometer in studies of ajaconine (isolated from Delphinium ajacis). A sample identified as pure ajaconine produced a mixture of five components when the [ Hgjtrimethylsilyl derivatives were analysed. The relative amounts of these compounds by peak-area estimation were (i) 477,... 

Alkaloids of Delphinium ajacis (syn. Consolida ambigua).—Waller and Lawrence" have reported further isolation and mass spectral studies of alkaloids from the common larkspur . Ajaconine (32), delcosine (18), acetyldelsosine (33),... 

This base was simultaneously reported as occurring in the seeds of Delphinium ajacis (cf. Applications of N.M.R. Spectrometry to the C19 Diterpenoid Alkaloids ). These are the first reports of this compound being isolated from plant materials. 

The alkaloids of the genus Delphinium may be classified into two distinct structural types the atisine type, represented by ajaconine, and the lycoctonine type, represented by delcosine, acetyldelcosine, and delsoline (Figure 3.18). The common larkspurs are widely distributed in the western United States and in Canada where they are a common cause of cattle poisoning. Both types of alkaloids from Delphinium ajacis have been studied (Frost et al., 1967). Plants were grown in the field on sandy loam soil at the Horticultural Farm in Stillwater with normal fertilization and... 

Figure 3.18. Structures of some diterpenoid alkaloids from Delphinium ajacis.

Figure 3.19. Variation of alkaloid content with age of Delphinium ajacis plants (Frost et al. 1967). Courtesy of The Chemical Society Publications.

Figure 3.20a. Alkaloid composition of Delphinium ajacis plants (190 days old) (Waller and...

Figure 3.20b. The ratio of lycoctonine-type to ajaconine alkaloids in Delphinium ajacis. These results were obtained using the direct probe-mass spectrometer LKB-9000P and a crude alkaloid fraction. Major fragment ions that are characteristic of the compound and which have low cross contribution from the other compounds were selected. The cross contribution was determined as were the response factors from known amounts of pure compounds. Samples were then analyzed by repetitive scans in the high mass range (where most of the important fragment ions occur). The ion intensities of the interpretive fragment ions are plotted, and the area under each curve is determined and corrected for cross contributions and response factors to arrive at a total microgram estimation for each known compound. Unknowns are monitored by their characteristic fragment ions and estimated relative to the knowns (from Waller and Lawrence, 1975).

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