Panaxadiol, C
30H
52O
3, a sapogenin of Ginseng roots was acetylated to afford monoacetate, C
32H
54O
4, which was oxidized with chromium trioxide to give panaxanolone acetate, C
52H
52O
4. On Wolff-Kishner reduction, panaxanolone acetate was converted into panaxanol, C
30H
52O
2, which was heated with hydrochloric acid in glacial acetic acid to furnish anhydropanaxanol acetate, C
32H
52O
2. On catalytic hydrogenation of anhydropanaxanol, isotirucallenol (X) was obtained, which was established by infrared and gaschromatography. A trimethyltetrahydropyrane ring system in panaxadiol was proved by mass-spectrometry, and the oxygen ring was cleaved by the action of hydrochloric acid on panaxanol. The α, β-unsaturated ketonic system was proved ultraviolet spectroscopically in the product derived from panaxanolone acetate by the action of sulfuric acid in glacial acetic acid. Thus the hindered hydroxyl of panaxadiol should be present at the 12-position. Consequently, it has been concluded that panaxadiol is a new tetracyclic triterpene of dammarane series having hydroxyls at the 3- and 12-positions and trimethyltetrahydropyrane ring at C
(17), as represented by the formula (T).
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