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Evolution of Rosmarinic Acid Biosynthesis

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Evolution of Rosmarinic Acid Biosynthesis Phytochemistry 70 (2009) 1663–1679 Contents lists available at ScienceDirect Phytochemistry journal homepage: www.elsevier.com/locate/phytochem Review Evolution of rosmarinic acid biosynthesis Maike Petersen *, Yana Abdullah, Johannes Benner, David Eberle, Katja Gehlen, Stephanie Hücherig, Verena Janiak, Kyung Hee Kim, Marion Sander, Corinna Weitzel, Stefan Wolters Institut für Pharmazeutische Biologie, Philipps-Universität Marburg, Deutschhausstr. 17A, D-35037 Marburg, Germany article info abstract Article history: Rosmarinic acid and chlorogenic acid are caffeic acid esters widely found in the plant kingdom and pre- Received 24 February 2009 sumably accumulated as defense compounds. In a survey, more than 240 plant species have been Received in revised form 19 May 2009 screened for the presence of rosmarinic and chlorogenic acids. Several rosmarinic acid-containing species Available online 25 June 2009 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 Keywords: orders of mono- and dicotyledonous angiosperms. The biosyntheses of caffeoylshikimate, chlorogenic Rosmarinic acid acid and rosmarinic acid use 4-coumaroyl-CoA from the general phenylpropanoid pathway as hydroxy- Caffeoylshikimic acid cinnamoyl donor. The hydroxycinnamoyl acceptor substrate comes from the shikimate pathway: shiki- Chlorogenic acid Phenylpropanoid metabolism mic acid, quinic acid and hydroxyphenyllactic acid derived from L-tyrosine. Similar steps are involved Acyltransferase in the biosyntheses of rosmarinic, chlorogenic and caffeoylshikimic acids: the transfer of the 4-coumaroyl CYP98A 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 monooxygen- ase 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 biosyn- thesis 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. Ó 2009 Elsevier Ltd. All rights reserved. Contents 1. Rosmarinic acid ..................................................................................................... 1664 1.1. Occurrence of rosmarinic acid in the plant kingdom . ..................................................... 1664 1.2. Screening of plant species for the presence of rosmarinic acid and chlorogenic acid . .................................. 1665 2. Biosynthesis of rosmarinic acid, chlorogenic acid and caffeoylshikimic acid . ............................................ 1666 3. D-isomer-specific 2-hydroxyacid dehydrogenases . ............................................................... 1672 3.1. Hydroxy(phenyl)pyruvate reductase from C. blumei ................................................................... 1673 4. CoA-ester-dependent BAHD hydroxycinnamoyltransferases . ............................................................... 1673 4.1. Hydroxycinnamoyltransferases in phenolic metabolism . ..................................................... 1673 4.2. Properties of hydroxycinnamoyl-CoA:hydroxyphenyllactate hydroxycinnamoyltransferase (rosmarinic acid synthase; RAS) . 1675 5. Cytochrome P450 CYP98A . .................................................................................. 1675 5.1. CYP98A in phenylpropanoid metabolism . ........................................................................ 1675 5.2. Properties of 4-coumaroyl-4’-hydroxyphenyllactate 3- and 3’-hydroxylase from C. blumei (CYP98A14) . ............... 1676 6. Possible evolutionary relationship of caffeoylshikimic/chlorogenic acid and rosmarinic acid biosynthesis. ............................ 1676 Acknowledgement . .................................................................................. 1677 References . ..................................................................................................... 1677 * Corresponding author. Tel.: +49 6421 2825821; fax: +49 6421 2825828. E-mail address: [email protected] (M. Petersen). 0031-9422/$ - see front matter Ó 2009 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2009.05.010 1664 M. Petersen et al. / Phytochemistry 70 (2009) 1663–1679 COOH COOH NH2 NH2 HO L-phenylalanine L-tyrosine PAL OH COOH HO TAT O OH HO O COOH COOH t-cinnamic acid C4H homogentisic acid HO O HPPD COOH HO caffeoyl-5'-O-quinic acid = chlorogenic acid 4-hydroxyphenylpyruvic acid OH HO 4C-S/Q 3H tocopherols HO 4-coumaric acid HPPR O 4CL O plastoquinones OH COOH SCoA O COOH HO H HO HO HO 4-coumaroyl-5'-O-quinic acid 4-coumaroyl-CoA 4-hydroxyphenyllactic acid + quinic acid RAS + shikimic acid HCS/QT OH O COOH OH H HO O O 4-coumaroyl-4'-hydroxyphenyllactic acid HO O COOH 4C-pHPL 3H 4C-pHPL 3'H HO OH OH 4-coumaroyl-5'-O-shikimic acid O COOH O COOH H H HO 4C-S/Q 3H OH O O OH HO caffeoyl-4'-hydroxy- 4-coumaroyl-3',4'-dihydroxy- O HO phenyllactic acid HO phenyllactic acid HO O COOH Caf-pHPL 3'H 4C-DHPL 3H OH O COOH HO H HO caffeoyl-5'-O-shikimic acid O OH + CoA HCS/QT (?) rosmarinic acid caffeoyl-CoA + shikimic acid HO Fig. 1. Proposed biosynthetic pathways to rosmarinic acid, caffeoylshikimic acid and chlorogenic acid as well as some other phenylpropanoid pathway-derived compounds. The involved enzymes are: PAL = phenylalanine ammonia lyase; C4H = cinnamic acid 4-hydroxylase; 4CL = 4-coumaric acid CoA-ligase; TAT = tyrosine aminotransferase; HPPR = hydroxyphenylpyruvate reductase; RAS = ‘‘rosmarinic acid synthase”, hydroxycinnamoyl-CoA:hydroxyphenyllactate hydroxycinnamoyltransferase; 4C-pHPL 3H, 4C- pHPL 30H = 4-coumaroyl-40-hydroxyphenyllactate 3/30-hydroxylases; Caf-pHPL 30H = caffeoyl-40-hydroxyphenyllactate 30-hydroxylase; 4C-DHPL 3H = 4-coumaroyl-30,40- dihydroxyphenyllactate 3-hydroxylase; HPPD = hydroxyphenylpyruvate dioxygenase; HCS/QT = hydroxycinnamoyl-CoA: shikimate/quinate hydroxycinnamoyltransferase; 4C-S/Q 3H = 4-coumaroylshikimate/quinate 3-hydroxylase. 1. Rosmarinic acid phyletic according to Grayer et al. (2003). The presence of RA in the Lamiaceae outside of the subfamily Nepetoideae was, however, re- 1.1. Occurrence of rosmarinic acid in the plant kingdom ported by Pedersen (2000) in Teucrium scorodonia and Aegiphila mollis of the sub-family Teucrioideae and Hymenopyramis brachiata The tanning compounds of Labiates have been known as Labiate of uncertain affinity within the family (according to Olmstead tannins (‘‘Labiatengerbstoffe”) for a long time. Research into the (2005)). On the other hand, RA was found in many species outside identification of these compounds started around 1950, and a com- the Lamiaceae and Boraginaceae (Petersen and Simmonds, 2003; pound named rosmarinic acid (RA) was isolated from Rosmarinus Table 1). The use of RA occurrence as a chemotaxonomical marker officinalis (Lamiaceae) by Scarpati and Oriente (1958). Rosmarinic therefore is not recommendable. As can be seen from Table 1,RAis acid is an ester of caffeic acid and 3,4-dihydroxyphenyllactic acid already present in the Anthocerotaceae (hornworts), one of the (Fig. 1). It was isolated from many species of the families Lamia- earliest land plant families. Own unpublished investigations could ceae and Boraginaceae and was identified as one of the active com- not show the occurrence of RA in the genus Chara of the green al- ponents of several medicinal plants (e.g. Salvia officinalis, Mentha x gae family Charophyceae which is seen as the algal predecessor of piperita, Thymus vulgaris, Melissa officinalis, Symphytum officinale) land plants. Within the land plants RA was found in species of the within these families. Not all members of the Lamiaceae, however, hornworts (family Anthocerotaceae), ferns (family Blechnaceae) as contain RA. The occurrence is mainly restricted to the subfamily well as some orders of the monocotyledonous plants and the Nepetoideae (Litvinenko et al., 1975), which is regarded as mono- rosids and asterids within the eudicotyledonous plants (Fig. 2). M. Petersen et al. / Phytochemistry 70 (2009) 1663–1679 1665 Table 1 Published occurrence of rosmarinic acid in the plant kingdom. Systematics are according to ‘‘Strasburger – Lehrbuch der Botanik” (Bresinsky et al., 2008). Subclass Order Family Reference Anthocerophytina Anthocerotales Anthocerotaceae Takeda et al. (1990), Petersen (2003) and Vogelsang et al. (2005) Filicophytina Blechnales Blechnaceae Harborne (1966), Bohm (1968) and Häusler et al. (1992) Spermatophytina, class Magnoliopsida Basal orders Chloranthales Chloranthaceae Zhu et al. (2008) Monocoty ledonous Alismatales Araceae Aquino et al. (2001) plants Potamogetonaceae Petersen (unpublished) Zosteraceae Ravn et al. (1994) and Achamlale et al. (2009) Zingiberales Cannaceae Petersen and Simmonds (2003) and Yun et al. (2004) Marantaceae Abdullah et al. (2008) Liliales Melianthaceae Lee et al. (2008) Eudicoty ledons Myrtales Onagraceae Huang et al. (2007) Celastrales Celastraceae Ly
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