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Pharmacy World and Science

, Volume 17, Issue 4, pp 113–119 | Cite as

Biosynthesis of pseudoisoeugenols in tissue cultures ofPimpinella anisum

Phenylalanine ammonia lyase and cinnamic acid 4- hydroxylase activities
  • Jürgen Reichling
  • Birgitt Kemmerer
  • Hedwig Sauer-Gürth
Articles

Abstract

The genusPimpinella contains pseudoisoeugenols, phenylpropanoids with a rare 2,5-dioxy substitution pattern on the phenyl ring. To study the biosynthesis of these compounds, we set up a leaf-differentiating tissue culture ofPimpinella anisum. These cultures mainly produce epoxy-pseudoisoeugenol-(2-methylbutyrate). To corroborate the biosynthetic pathway of epoxy-pseudoisoeugenol-(2-methylbutyrate) as proposed on the basis of investigations with13C/14C-labelled precursors, the key steps of the pathway were investigated at an enzyme level. Experiments with cell-free homogenates clearly revealed that L-phenylalanine is converted to (E)-cinnamic acid by phenylalanine ammonia lyase and that (E)-cinnamic acid is converted top-coumaric acid by cinnamic acid 4-hydroxylase. L-2-aminooxy-3-phenylpropionic acid, an analogue of L-phenylalanine, inhibited the incorporation of L-[3′-13C]phenylalanine into epoxy-pseudoisoeugenol-(2-methylbutyrate). Up to 2% of the precursor DL-[3′-13C]phenyllactate was incorporated into epoxy-pseudoisoeugenol-(2-methylbutyrate). Inhibition experiments with oxalacetic acid clearly showed that cinnamic acid is not formed by dehydration of phenyllactic acid in this leaf-differentiating tissue culture ofP. anisum.

Keywords

Biosynthesis Cell-free system Cinnamic acid 4-hydroxylase Enzyme activity Pimpinella anisum Phenylpropanoids Phenylalanine ammonia lyase Pseudoisoeugenols Tissue culture 

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Copyright information

© Royal Dutch Association for Advancement of Pharmacy 1995

Authors and Affiliations

  • Jürgen Reichling
    • 1
  • Birgitt Kemmerer
    • 1
  • Hedwig Sauer-Gürth
    • 1
  1. 1.Institut für Pharmazeutische Biologie der Universität HeidelbergHeidelbergGermany

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