Studies on asterosaponins—V : A novel steroid conjugate, 5α-pregn-9(11)-ene-3β,6α-diol-20-one-3-sulfate,from a starfish saponin,asterosaponin A |
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Authors: | S Ikegami Y Kamiya S Tamura |
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Institution: | Department of Agricultural Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo 113, Japan |
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Abstract: | A new crystalline steroid conjugate was obtained by partial acid hydrolysis of asterosaponin A, a steroidal saponin from the starfish, Asterias amurensis. The structure of the conjugate was established as 5α-pregn-9(11)-ene-3β,6α-diol-20-one-3-sulfate (2) on the basis of elemental analysis, IR and PMR spectra measurement and chemical reaction. Solvolysis of compound 2 yielded 5α-pregn-9(11)-ene-3β,6α-diol-20-one. Oxidation with chromium trioxide-pyridine complex followed by solvolysis afforded a new steroid, 5α-pregn-9(11)-ene-3β-ol-6,20-dione, whose structure was deduced by the measurement of ORD curve and PMR spectra. Thus, the location of carbohydrate moiety in asterosaponin A has been assigned to 6α-hydroxy group of the steroid conjugate. |
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