South African Senecio alkaloids. Part 6. The toxic alkaloids of Senecio scleratus sp. nov. Schweikerdt

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Peer-Reviewed Research
  • SDG 12
  • Abstract:

    (1) Senecio sceleratus sp. nov. 'Schweickerdt is an extremely toxic Senecio species. It contains at least three more or less toxic alkaloids, viz., isatidine, retrorsine and a new alkaloid, sceleratine, (2) Sceleratine, C₁₈H₂₇O₇N, crystallizes with one molecule of water of of crystallization from water and apparently three molecules of ethanol of crystallization from ethyl alcohol. M.P. 178°C, [α]D/21 = +54·0° (ethanol). (3) Upon catalytic hydrogenation sceleratine undergoes hydrogenolysis at the B-hydroxyl and retronecanol and sceleranecic dilactone acid are isolated. (4) Hydrolysis of sceleratine leads to the isolation of the well-known necine base, retronecine and a new dilactone necic acid viz. sceleranecic acid. (5) Sceleranecic acid has the formula C₁₀H₁₄O₅, the m.p. 156°C. (also 213°C.) and [α]24/D = -9.3 (water). (6) Sceleratine is bitter, fairly soluble in water and readily forms addition compounds with hydrochloric acid, nitric acid, picric acid, perchloric acid, methyl-iodide and aurichloride. (7) Experiments to determine the relative toxicity of the alkaloids mentioned are being carried out.