Evolution of rosmarinic acid biosynthesis.
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.
Petersen
Maike
M
Institut für Pharmazeutische Biologie, Philipps-Universität Marburg, Marburg, Germany. petersen@staff.uni-marburg.de
Abdullah
Yana
Y
Benner
Johannes
J
Eberle
David
D
Gehlen
Katja
K
Hücherig
Stephanie
S
Janiak
Verena
V
Kim
Kyung Hee
KH
Sander
Marion
M
Weitzel
Corinna
C
Wolters
Stefan
S
D000217:Acyltransferases / Q000235:genetics / Q000378:metabolism*; D002726:Chlorogenic Acid / Q000378:metabolism*; D002934:Cinnamates / Q000737:chemistry / Q000378:metabolism*; D003577:Cytochrome P-450 Enzyme System / Q000235:genetics / Q000378:metabolism*; D053630:Depsides / Q000737:chemistry / Q000378:metabolism*; D019143:Evolution, Molecular; D015394:Molecular Structure; D010944:Plants / Q000201:enzymology / Q000235:genetics / Q000378:metabolism*; D012765:Shikimic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D000097123:Rosmarinic Acid
D000217:Acyltransferases; D002726:Chlorogenic Acid; D002934:Cinnamates; D003577:Cytochrome P-450 Enzyme System; D053630:Depsides; D012765:Shikimic Acid; D000097123:Rosmarinic Acid; C036792:5-O-caffeoylshikimic acid; C110890:cytochrome P-450 CYP98A1 (Sorghum bicolor)