S. Friederich, U. H. Maier, B. Deus-Neumann
Feb 24, 1999
Citations
1
Influential Citations
61
Citations
Journal
Phytochemistry
Abstract
Abstract Using sterile thallus tissue of Marchantia polymorpha , the biosynthesis of the cyclic bis(bibenzyl) marchantin A was investigated. The synthesis of the radioactively and 13 C-labelled precursors for the application experiments is described. Feeding experiments showed that rings A and C of the marchantin molecule are derived from the benzene ring of l -phenylalanine via trans -cinnamic acid and p -coumaric acid. Further application of 13 C-labelled precursor with subsequent 13 C NMR spectroscopy proved that dihydro- p -coumaric acid is an intermediate in marchantin biosynthesis. A phenylpropane/polymalonate pathway using dihydro- p -coumaric acid and acetate/malonate is proposed for the biosynthesis of the bibenzyl monomers which were confirmed to be the building blocks of the marchantin molecule. The bibenzyls in turn are coupled in a unique way to form the bis(bibenzyl) structure.