Phytochemistry p. 3839 - 3844 (1992)
Update date:2022-09-26
Topics:
Damtoft, Soeren
Jensen, Soeren Rosendal
Nielsen, Bent Juhl
Thorsen, Jesper
Deuterium-labelled samples of 8-epi-iridodial, 8-epi-iridotrial and their glucosides were fed to Hebenstretia dentata.The aglucones were better precursors than their glucosides of ipolamiide and lamiide, the iridoid glucosides of the plant.A feeding experiment with (13)C-labelled 10-hydroxy-geraniol showed that C-3 and C-11 are equivalent during biosynthesis of the iridoid glucosides and, thus, glucosidation must take place after formation of 8-epi-iridotrial.Isolation of the minor metabolites after feeding with 8-epi-deoxyloganic acid suggested that the route from this compound proceeds by oxidation at C-8 followed by esterification and that oxidation at C-5 is the final step. Key Word Index: Hebenstretia dentata; Scrophulariaceae; iridoid glucosides; ipolamiide; lamiide; biosynthesis; (2)H NMR.
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