BIOSYNTHESIS OF IRIDOID GLUCOSIDES IN HEBENSTRETIA DENTATA
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.
Damtoft, Soeren,Jensen, Soeren Rosendal,Nielsen, Bent Juhl,Thorsen, Jesper
Get Best Price for27934-98-1(1S)-1α-(β-D-Glucopyranosyloxy)-1,4a,5,6,7,7aα-hexahydro-4aα,7α-dihydroxy-7-methylcyclopenta[c]pyran-4-carboxylic acid methyl ester