The Alkaloids of Chinese Drug,Aconitum spp.——Ⅹ.New Alkaloids from Guan-Bai-Fu-Tzu,Aconitum koreanum

Six alkaloids have been isolated from the Chinese drug, Guan-Bai-Fu-Tzu, Aconitum koreanum R.Raymund. One of them was found to be identical with hypaconitine and the other five appeared to be new alkaloids, which are provisionally named as guan-fu base A,B,C,D and E respectively. Physical and chemical data of these new alkaloids are as follows:The guan-fu base A,C₂₄H₃₁O₆N, m.p. 198℃, α_D^22.8+49°(chloroform). Several crystalline salts and derivative were prepared: nitrate, m.p.265℃; hydrochloride,m.p.290℃;hydrobromide,m.p.293℃; perchlorate,m.p.272—273℃; methiodide, m.p. 284.5—285.5℃ and diacetate, m.p. 154.5—155℃. When it was hydrolysed in methanolic potassium hydroxide, an amino alcohol C₂₀H₂₇O₄N, m.p.243—244℃ and acetic acid were obtained. On oxidation with acidic permanganate it gave two crystalline products,C₂₂H₂₇O₇N, m.p. 204℃ and C₂₃H₂₉O₈N·HClO₄, m.p. 286℃ (dec.)respectively. It was easily reduced to dihydro compound C₂₄H₃₅O₆N, m.p. 200℃, in the presence of Adams platinum catalyst. The guan-fu base B has the formula C₂₂H₂₉O₅N, m.p. 204℃, α_D^26.6+16°(chloroform). The following crystalline salts and derivative were prepared: hydrobromide, m.p.257—258℃;perchlorate,m.p.255—256℃;methiodide,m.p.317—318℃ and triacetate,m.p.154—155℃. Its monoacetate was to be identical with the guan-fu base A. The guan-fu base C has the formula C₂₂H₃₃O₂N, m.p. 150℃, α_D^16.4-21.2°(alcohol).The following crystalline salts and derivative were obtained:nitrate,m.p. 222℃; hydrobtomide,m.p.235℃ and diacetatic hydrochlorate,m.p.222.5—224℃. The guan-fu base D and E have not been obtained yet in crystalline states. However,the nitrate of guan-fu base D,C₂₄H₃₅O₃N·HNO₃,m.p.210—211℃ and the perchlorate of guan-fu base E, C₂₉H₄₃O₇N·HClO₄, m.p.272℃ were prepared. The partial formula of guan-fu base A,B and C are expressed as C₁₉H₂₀(0H)₂(CH₃COO)₂(CH₃)(:N·),C₁₉H₂₀(OH)₃(CH₃COO)(CH₃)(:N·)and C₁₉H₂₃(OH)₂(CH₃)(N—C₂H₃)respectively.