49 イリドイド配糖体の生合成におけるイリダン骨格形成機構について

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Various combinations of ^<13>C-labeled and non-labeled acyclic monoterpenes including the following compounds were administered to the iridoid-producing cell suspension cultures of Gardenia jasminoides f. qrandiflora: 10-hydroxygeraniol (4), 9,10-dihydroxygeraniol (21), 10-hydroxycitronellol (19), 9,10-dihydroxycitronellol (22) or a pair of (10-^2H)-iridodial (13) and (11-^2H_2)-7,8-dehydroiridodial (17). The incorporation of ^<13>C or ^2H label of these substances into tarennoside (14), a major iridoid glucoside of the cultured cells, was traced by means of ^<13>C- or ^2H-NMR spectrometry. The results revealed that 10-hydroxygeraniol (4) and 7,8-dehydroiridodial (17) are the obligatory precursors of the iridoid glucosides of the Gardenia cells and that the ^2H label of (11-^2H_2)-17 was incorporated into 3 and 11 positions of tarennoside (14) with extensive randomization. Administration experiments of ^3H-labeled compounds including 10-hydroxygeraniol (4), 10-oxogeranial (11), 9,10-dihydroxygeraniol (21), 9-hydroxy-10-oxogeranial (24), 10-hydroxycitronellol (19), and iridodial (13) to Catharanthus roseus showed that incorporations of 10-hydroxygeraniol (4) and iridodial (13) into vindoline (23) are much greater than those of the other compounds. It is therefore highly probable that indole alkaloids, and therefore, secoiridoids are biosynthesized via iridodial (13) formed by way of the cyclization of 10-oxoneral (12). It has thus been clarified that all the iridoids are biosynthesized via the intermediate cation (16) formed through the cyclization of 10-oxogeranial (11) or 10-oxoneral (12).
天然有機化合物討論会の論文
1980-09-10

49 イリドイド配糖体の生合成におけるイリダン骨格形成機構について

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