Abstract
Feeding experiments with deuterium-labelled precursors to Fraxinus excelsior, Syringa josikaea and S. vulgaris have shown that the biosynthesis of the oleoside-type secoiridoids (e.g. oleuropein) proceeds via iridodial, iridotrial, deoxy-loganic acid aglucon and deoxy-loganic acid. Hydroxylation of the 7α-position is followed by oxidation and methylation of C-11 to give 7-ketologanin, the last carbocyclic iridoid precursor of the oleosides. The sequences of the steps between deoxy-loganic acid and 7-ketologanin may differ with plant species and time of year. 8-Epi-kingisidic acid and 8-epi-kingiside can be formed from 8-ketologanic acid (and its methyl ester). The secoiridoids, fliederoside and lilacoside, from S. vulgaris have been characterized.
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