36 椿の実のサポゲノールの構造

概要

論文の詳細を見る
The mixture of saponins obtained from Camellia japonica L. was hydrolyzed and separated by chromatography into camellia sapogenols, CS-A [C_<30>H_<46>(OH)_4, m. p. 282-283°], CS-B [C_<30>H_<44>(=O)(OH)_4, m. p. 200-205°], and CS-C [C_<30>H_<45>(OH)_5, m. p. 262-263°]. Structural relationships between them were established by the LiAlH_4 reduction of CS-B to CS-C and by the Huang Minion reduction of CS-B to CS-A. The existence of an olean-12-ene carbon skeleton in these compounds was deduced from the spectra of the diene-dione derived from the CS-C diacetonide acetate. The nature and the location of the oxygen functions were shown by close examination of the NMR spectra of the sapogenols and their derivatives and by the result of chemical reactions. On this basis, the sapogenols A, B, and C have been assigned the structures, olean-12-ene-3β, 16α(or β), 22(or 21)α, 27-tetraol, olean-12-ene-3β, 16α(or β), 22(or 21)α, 27-tetraol-23-al, and olean-12-ene-3β, 16α(or β), 22(or 21)α, 23, 27-pentaol, respectively. These three sapogenols have also been isolated from Camellia sinensis (L) O. Kuntse.
天然有機化合物討論会の論文
1966-09-15