41 アグリコン部のF環構造のみを異にする数種のスピロスタノール配糖体の共存と,それらの高速液体クロマトグラフィーによる分離

概要

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During a study on the constituents of fresh underground parts of Rhodea japonica, two spirostanol glycosides R-3(I) and R-8(II) were obtained. I and II seemed pure on normal- and RP-TLC, and characterized, respectively, as 1-O-rhamno-xyloside and 3-O-glucoside of rhodeasapogenin(5β-25S-spirostan-1β,3β-diol)(III). They were, however, acid hydrolyzed to yield III and minor amounts of isorhodeasapogenin(25R)(IV) and convallamarogenin(Δ^<25(27)>)(V) indicating their unhomogeneity. As a method of purity control of the glycosides in situ, the CMR spectra were found to be of use, but in order to develop a new means which requires much less sample and provides much finer separation, and which could be extended to a preparative scale, application of HPLC was studied. By the method using Radial Pak C_<18> and 90% MeOH, I and II were separated, respectively, to give a new compound(I_a, II_a), the glycoside of V and a mixture of the glycosides of III and IV. Subsequent separation of the last mixture was, in the long run, successfully achieved by using TSK LS-410 column and 90% MeOH at 0℃. I_a and II_a were identified as the first natural glycosides, of which aglycones are equally 22-epi(22β-O)(22S), 25S(eq-Me) congener of III, and their properties and formation from the corresponding furostanol glycosides are discussed. The above HPLC was applied also to "dioscin," crude neotokoronin and "digitonin."
天然有機化合物討論会の論文
1982-09-10