Document Detail

Evolution of rosmarinic acid biosynthesis.
MedLine Citation:
PMID:  19560175     Owner:  NLM     Status:  MEDLINE    
Rosmarinic acid and chlorogenic acid are caffeic acid esters widely found in the plant kingdom and presumably accumulated as defense compounds. In a survey, more than 240 plant species have been screened for the presence of rosmarinic and chlorogenic acids. Several rosmarinic acid-containing species have been detected. The rosmarinic acid accumulation in species of the Marantaceae has not been known before. Rosmarinic acid is found in hornworts, in the fern family Blechnaceae and in species of several orders of mono- and dicotyledonous angiosperms. The biosyntheses of caffeoylshikimate, chlorogenic acid and rosmarinic acid use 4-coumaroyl-CoA from the general phenylpropanoid pathway as hydroxycinnamoyl donor. The hydroxycinnamoyl acceptor substrate comes from the shikimate pathway: shikimic acid, quinic acid and hydroxyphenyllactic acid derived from l-tyrosine. Similar steps are involved in the biosyntheses of rosmarinic, chlorogenic and caffeoylshikimic acids: the transfer of the 4-coumaroyl moiety to an acceptor molecule by a hydroxycinnamoyltransferase from the BAHD acyltransferase family and the meta-hydroxylation of the 4-coumaroyl moiety in the ester by a cytochrome P450 monooxygenase from the CYP98A family. The hydroxycinnamoyltransferases as well as the meta-hydroxylases show high sequence similarities and thus seem to be closely related. The hydroxycinnamoyltransferase and CYP98A14 from Coleus blumei (Lamiaceae) are nevertheless specific for substrates involved in RA biosynthesis showing an evolutionary diversification in phenolic ester metabolism. Our current view is that only a few enzymes had to be "invented" for rosmarinic acid biosynthesis probably on the basis of genes needed for the formation of chlorogenic and caffeoylshikimic acid while further biosynthetic steps might have been recruited from phenylpropanoid metabolism, tocopherol/plastoquinone biosynthesis and photorespiration.
Maike Petersen; Yana Abdullah; Johannes Benner; David Eberle; Katja Gehlen; Stephanie H??cherig; Verena Janiak; Kyung Hee Kim; Marion Sander; Corinna Weitzel; Stefan Wolters
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Review     Date:  2009-06-25
Journal Detail:
Title:  Phytochemistry     Volume:  70     ISSN:  1873-3700     ISO Abbreviation:  Phytochemistry     Publication Date:    2009 Oct-Nov
Date Detail:
Created Date:  2009-11-13     Completed Date:  2010-01-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0151434     Medline TA:  Phytochemistry     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1663-79     Citation Subset:  IM    
Institut f??r Pharmazeutische Biologie, Philipps-Universit??t Marburg, Marburg, Germany.
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MeSH Terms
Acyltransferases / genetics,  metabolism*
Chlorogenic Acid / metabolism*
Cinnamates / chemistry,  metabolism*
Cytochrome P-450 Enzyme System / genetics,  metabolism*
Depsides / chemistry,  metabolism*
Evolution, Molecular*
Molecular Structure
Plants / enzymology,  genetics,  metabolism*
Shikimic Acid / analogs & derivatives,  chemistry,  metabolism
Reg. No./Substance:
0/Cinnamates; 0/Depsides; 138-59-0/Shikimic Acid; 327-97-9/Chlorogenic Acid; 537-15-5/rosmarinic acid; 73263-62-4/5-O-caffeoylshikimic acid; 9035-51-2/Cytochrome P-450 Enzyme System; EC 1.14.-/cytochrome P-450 CYP98A1 (Sorghum bicolor); EC 2.3.-/Acyltransferases

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

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