42 数種のモクセイ科植物のセコイリドイド配糖体の構造と生合成(口頭発表の部)

概要

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Secoiridoid glucosides of three types, oleoside (1)-, 10-hydroxyoleoside (4)- and ligustaloside (5)-type occur only in oleaceous plants. We had proposed the bisynthesis pathway of these glucosides.3) In order to examine the proposed pathway, a pair of respective stereoisomers of 8,10- epoxysecoxyloganin (6, 6a) and 8,10-epoxysecologanin (7, 7a), and their labeled derivatives were synthesized from secologanin (3) and fed to three oleaceous plants, Olea europaea, Osmanthus fragrans and Ligustrum japonicum. 8S,10-Epoxysecologanin (7) was incorporated into oleuropein (15), 10-acetoxyoleuropein (16) and ligustalosides A (13) and B (14) more efficiently than three other epoxides (6, 6a, 7a). Based on these results, we have proposed the possible biosynthetic rout of these glucosides as shown in Scheme 2. Further studies on the secoiridoids from oleaceous plants in connection with the biosynthesis resulted in the isolation of 8-epikingiside (17) from L. lucidum and five new glucosides (20, 21, 22, 23, 24) from Jasminum mesnyi.
天然有機化合物討論会の論文
1988-09-26