GUAYEWUANINE B

GUAYEWUANINE B Chemische Eigenschaften,Einsatz,Produktion Methoden

• Beschreibung

  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.

• Einzelnachweise

  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)

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