47 クチナシカルス培養細胞によるイリドイド配糖体の生合成研究

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[10-^3H]-10-Hydroxygeraniol (7), [10-^3H]-iridodial (14), [10-^3H]-iridodial glucoside (17) and [10-^3H]-iridotrial (9) were administered to the cells of Gardenia jasminoides forma grandiflora and the incorporation of these substances into iridoid glucosides such as tarennoside (1), geniposide (2) and gardenoside (3) was examined. Consequently, it was established that 10-hydroxygeraniol (7) is incorporated into glucosides 1, 2, 3 etc. via iridodial (14) in the cultured cells of the Gardenia plant and that the nonequivalent carbons at C-9 and C-10 of 7, after the iridoid skeleton formation, randomize between the 3 and 11 positions. This fact was also confirmed by administration experiment of [9-^<13>C]-10-hydroxygeraniol (7). Administration of 3'-O-methyl derivatives (23), (21), (26) and (24) of iridodial glucoside (17), deoxyloganin (4), deoxygeniposide (20) and geniposide (2) to the cultured cells resulted in the transformation of 21 and 24 into 3'-O-methylloganin (22) and 3'-O-methylgardenoside (25), respectively, while any other conversion was not observed. These phenomena were also observed in the Gardenia cell cultures lacking the iridoid-producing ability. These results suggest that loganin (5) is not the biosynthetic precursor of 2 and 3.
天然有機化合物討論会の論文
1978-08-22