GUAYEWUANINE B

Description

A aconite alkaloid present in Aconitum fischeri Reich, A. sachalinense, Fr. Schmidt (Saghalien) and A. subcuneaturn, Nakai, this base is amorphous but yields crystalline salts, e.g. the perchlorate, m.p. 230-2°C (dec.); aurich10ride, m.p. 208-9°C (dec.) and a perbromide, m.p. 181-2°C (dec.). Boiling dilute H2S04 causes hydrolysis with the production of acetic acid and jesanisaconine (p-anisoylaconine) forming a crystalline hydrochloride, m.p. 209- 21 O°C (dec.).Alkaline hydrolysis gives acetic and p-anisic acids and aconine. Pyrolysis furnishes pyrojesaconitine, obtained as the crystalline perchlorate, m.p. 171-2°C; [α]¹³_D - 27.4° (MeOH). Oxidation with KMn04 yields acetaldehyde, indicative of an ethylimino group. The structure of the alkaloid has been determined by con_x0002_tinuous monitoring of the pyrolysis and an examination of the products produced.
Jesaconitine is, like all of the aconitines, highly toxic producing raspiratory paralysis and a direct toxic action on the heart, the latter often terminating in ventricular fibrillation.

Occurrence

A complex aconitine alkaloid, yunaconitine has been isolated from Aconitum hemsJeyanum.

References

Makoshi., Arch. Pharm., 247,243 (1909)
Majima, Suginome, Morio., Ber., 57B, 1486 (1924)
Majima, Morio.,Annalen., 476,171,194,203 (1929)
Tamura., ibid, 533,183 (1937)
Structure:
Keith, Pelletier., Chem. Commun., 993 (1967)
Keith, Pelletier., ibid, 161 (1968)
Keith, Pelletier., 1. Org. Chem., 33, 2497 (1968)