57(P23) C-13 NMRグルコシド化シフト則によるマタタビ科植物などのヨノン系配糖体の絶対構造の決定(ポスター発表の部)

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The absolute connfiguration of kiwiionoside (1), coexists with actinidioionoside (9) in Actinidiaceae, was determined to be 3S, 5R, 6R, and 9R by single crystal X-ray analysis. The absolute configuration of actinidioionoside (9) was determined by use of an aglucone of 1 by means of C-13 NMR glucosidation shift rules proposed by Tori et al.. That of roseoside, from Raphanus satives, was elucidated to be 6S and 9R by the results of X-ray diffraction method. It was clarified that the glucosidation shift rules was applied to ionone type glucosides regardless of measuring solvents by the comparison of the data of C-13 NMR between the enzymatic degradation product, (6S, 9R)- vomifoliol (2a), and the glucosides (2, 3 and 4). Furthermore, the absolute structure of (6R, 9S) and (6S, 9S)-roseosides (3 and 4) was revealed on the basis of the above fact, respectively. The absolute configuration of (6R, 9S)-3-oxo- a -ionol glucoside was revised to be (6S, 9S)-glucoside (12), by using the glucosidation shift rules. According to the avobe rules, we could lay down the proper parameters of C-13 NMR glucosidation shifts (allyl alcohol and sterically hindered case) in the field of ionone type glucosides.
天然有機化合物討論会の論文
1996-09-02