Polyhydroxylated steroidal constituents from the fresh rhizomes of Tupistra yunnanensis.

Six new polyhydroxylated steroidal saponins, tupistrosides A-F (1-6), together with nine known steroids, were isolated from the fresh rhizomes of Tupistra yunnanensis. Their structures were elucidated to be (25S)-1beta,4beta,5beta-trihydroxy-spirostane-3beta-yl O-alpha-l-arabinopyranoside (1), 1beta,24beta-dihydroxy-spirost-5,25(27)-dien-3alpha-yl O-beta-d-glucopyranoside (2), (22S,25S)-1alpha,2beta,3alpha,5alpha-tetrahydroxy-furo-spirostane-26-yl O-beta-d-glucopyranoside (3), 1beta,3alpha,22 xi-trihydroxy-furost-5,25(27)-dien-26-yl O-beta-d-glucopyranoside (4), 26-O-beta-d-glucopyranosyl-1beta,22-dihydroxy-furost-5-en-3alpha-yl O-beta-d-glucopyranoside (5) and 22-methoxy-1beta,2beta,3beta,4beta,5beta,7alpha-hexahydroxy-furost-25(27)-en-6-one-26-yl O-beta-d-glucopyranoside (6), respectively, by means of spectroscopic analysis and the results of acid hydrolysis.

An improved procedure for the isolation of suprasterol2 I and II from a photochemical reaction mixture of ergocalciferol (vitamin D2).

An improved procedure for the isolateion suprasterol2 I and II from a photochemical reaction mixture of ergocalciferol (vitamin D2) and their spectral data are described in this paper. When a solution of ergocalciferol in ethanol was irradiated by UV light from a high-pressure mercury lamp, the reaction mixture gave six spots, including suprasterol2 I and II, on the thin-layer chromatogram, while the peaks corresponding to pyro-D2, isopyro-D2,5,b-trans-D2, suprasterol 2 I and II were observed in the gas chromatogram obtained from a capillary column GLC (Suprasterol2 I and II were main peaks). After purifying the mixture by column chromatography on silica gel containing 12% alumina as an absorbent, two main fractins were isolated. The data of their spectra, TLC and GLC showed that the former fraction was suprasterol2 II while the latter was suprasterol2 I and that the both fractions contained the respective compound only. Both suprasterol2 were crystallized as the 3,5-dinitro-benzoates.