Document Detail


Biosynthesis of pseudoisoeugenols in tissue cultures of Pimpinella anisum. Phenylalanine ammonia lyase and cinnamic acid 4-hydroxylase activities.
MedLine Citation:
PMID:  7581216     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The genus Pimpinella 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 of Pimpinella 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 with 13C/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 to p-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 of P. anisum.
Authors:
J Reichling; B Kemmerer; H Sauer-Gürth
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Pharmacy world & science : PWS     Volume:  17     ISSN:  0928-1231     ISO Abbreviation:  Pharm World Sci     Publication Date:  1995 Jul 
Date Detail:
Created Date:  1995-12-07     Completed Date:  1995-12-07     Revised Date:  2009-11-19    
Medline Journal Info:
Nlm Unique ID:  9307352     Medline TA:  Pharm World Sci     Country:  NETHERLANDS    
Other Details:
Languages:  eng     Pagination:  113-9     Citation Subset:  IM    
Affiliation:
Institut für Pharmazeutische Biologie, Universität Heidelberg, Germany.
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MeSH Terms
Descriptor/Qualifier:
Angiosperms / cytology,  metabolism
Cell-Free System
Cinnamates / metabolism*
Enzyme Activation
Phenylalanine / metabolism*
Phenylalanine Ammonia-Lyase / biosynthesis*
Plants / cytology,  metabolism*
Time Factors
Chemical
Reg. No./Substance:
0/Cinnamates; 621-82-9/cinnamic acid; 63-91-2/Phenylalanine; EC 4.3.1.24/Phenylalanine Ammonia-Lyase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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