Iridoid Biosynthesis: 7-Deoxyloganetic Acid 1-O-Glucosyltransferase in Cultured Lonicera japonica Cells.

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  • YAMAMOTO Hirobumi
    Medicinal Plant Garden, School of Pharmaceutical Sciences, Nagasaki University
  • SHA Manyoung
    Medicinal Plant Garden, School of Pharmaceutical Sciences, Nagasaki University
  • KITAMURA Yoshie
    Medicinal Plant Garden, School of Pharmaceutical Sciences, Nagasaki University
  • YAMAGUCHI Misako
    Laboratory of Pharmacognosy, Gifu Pharmaceutical University
  • KATANO Nobuyuki
    Laboratory of Pharmacognosy, Gifu Pharmaceutical University
  • INOUE Kenichiro
    Laboratory of Pharmacognosy, Gifu Pharmaceutical University

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説明

Iridoid 1-O-glucosylation enzyme activities of crude cell-free extracts prepared from loganin-producing plants and nonproducing cultured cells were comparatively examined. Crude cell-free extracts from Lonicera japonica cell suspension cultures glucosylated 7-deoxyloganetic acid, 7-deoxyloganetin, and loganetin, but not iridotrial, an intermediate just preceding 7-deoxyloganetic acid. Crude cell-free extracts from Hydrangea macrophylla young leaves also glucosylated 7-deoxyloganetin and loganetin, whereas those from cultured cells induced from iridoid-nonproducing plants did not show any iridoid glucosylation activity. The partially purified glucosyltransferase from L. japonica cells showed the highest glucosylation activity for loganetin. However, kinetic studies showed that Km values for 7-deoxyloganetic acid, 7-deoxyloganetin, and loganetin were 106μM, 561μM, and 660μM, respectively, indicating that the enzyme had the highest affinity to 7-deoxyloganetic acid. These data suggest the presence of a pathway for the biosynthesis of loganin, in which 7-deoxyloganetic acid is glucosylated at the 1-O position to give 7-deoxyloganic acid, which is further hydroxylated and methylated to produce loganin.

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