SONGORINE

Description

Both Aconitum karakoZicum and A. soongoricum contain this atisine type alkaloid which is strongly laevorotatory with [α]_D - 139.89°. The ultraviolet spectrum contains a single absorption maximum at 290 mil. Several crystalline salts and derivatives are known including the hydrochloride, m.p. 257-8°C; [α]_D - 113.99° (H20); hydrobromide, m.p. 261°C; nitrate, m.p. 230-l oC (dec.); perchlorate, m.p. 234-5°C (dec.); methiodide, m.p. 2l3-4°C (dec.) and the semicarbazone, m.p. 247-8°C (dec.). Catalytic hydrogenation over Pt02 gives the dihydro derivative, m.p. 205-6°C, giving a hydrochloride, m.p. 286- 7°C and a methiodide, m.p. 255-6°C. With AcCl the alkaloid yields the diacetyl derivative, m.p. l80-2°C, forming a hydrochloride dihydrate, m.p. 239-240°C. When boiled with KOH for 2 hours, the base gives des-N-methylsongorine, isolated as the hydrochloride, m.p. 285°C.

Biological Activity

Aconitum is a genus rich of diverse alkaloids. More than 450 alkaloids have been identified in a variety of species. Songorine is a C20 diterpenoid alkaloid and 12-keto analog of napelline, isolated from Aconitum soongaricum and was associated with a heterogeneous panel of biological functions.
Alkaloids are well-studied secondary metabolites, with recent preclinical studies evidencing that many of them exhibit anti-cancer, anti-depressant, anti-nociceptive, anti-inflammatory, anti-pyretic, anti-platelet, anti-oxidant, and anti-bacterial properties.

References

Yunusov.,J. Gen. Chem., USSR, 18, 515 (1948)
Wiesner et al., Chem. Ind., 173 (1957)
Yunusovetal., Khim. Prir. Soedin., 6, 101 (1970)
Structure: Wiesner, Ito, Valenta., Experientia, 14,167 (1958)
Sugasawa., Chem. Pharm. Bull. (Tokyo), 9, 897 (1961)
Absolute configuration: Okamoto et al., Chem. Pharm. Bull. (Tokyo), 13, 1270 (1965)

Raw materials

Preparation Products