Deoxy-[6,7,8,10-2H] loganic acid and 8-epideoxy-[6,7,8, 10-2 H] loganic acid were fed to Thunbergia alata. The former was incorporated into stilbericoside with retention of the label at H-6, H-7 and H-8. Administration of deuterium-labelled loganic acid, adoxosidic acid, capensioside and 8(S)-bisdeoxy-7,8-dihydroaucubin showed that the first steps in the biosynthesis of stilbericoside from deoxyloganic acid are most probably lo-hydroxylation followed by decarboxylation.
biosynthesis, iridoid glucosides, Thunbergia alata, Acanthaceae, stilbericoside, 2H NMR
Publication DOI: 10.1016/S0031-9422(00)89574-6Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Department of Organic Chemistry, The Technical University of Denmark, Lyngby, Denmark
Methods: 13C NMR, 1H NMR, TLC, HPLC, MPLC, radiolabelling
Found