Senecio platyphyllus

C18H23N0, Senkirkine Senecio platyphyllus D.C. (116) Senecio kirkii Hook (136) 197-198 -6.2° ... 

Platynecine (III), C8H15NO2, first obtained by Orekhov and Tiedebel (38) on alkaline hydrolysis of platyphylline (from Senecio platyphyllus), was degraded to heliotridane by Konovalova and Orekhov (40). The method was as follows Dichloroplatynecine, CgHisChN, m.p. 63-64° (hydrochloride, m.p. 186-187° picrate, m.p. 205-206°) was obtained in low yield when platynecine was treated with thionyl chloride. When dichloroplatynecine was reduced with sodium and ethanol followed by hydrogen over platinum oxide catalyst, heliotridane was the product. Identity was established by specific rotation and mixed melting points of all derivatives (54). The formation of heliotridane from platynecine proved that this alkaloid hydrolysis product also has the same basic skeleton that is present in heliotridine and retronecine. 

Seneciphylline was obtained together with platyphylline in a total crude yield of about 1.0% from Senecio platyphyllus. It was obtained together with a small amount of spartioidine in a total crude yield of 0.54%. It was found to be the only alkaloid present (0.04%) in Senecio stenocephalus. 

Senecio. Alkaloids accumulate in the roots of S. platyphyllus DC. and reach a maximum at the flowering stage when they disappear from the aerial parts except from the seeds (357). During vigorous growth in spring they appear as W-oxides. 

---