Rosmarinic acid: new aspects

Abdullah Y, Schneider B, Petersen M (2008) Occurrence of rosmarinic acid, chlorogenic acid and rutin in Marantaceae species. Phytochem Lett 1:199–203 Acar G, Dogan NM, Duru ME, Kivrak I (2010) Phenolic profiles, antimicrobial and antioxidant activity of the various extracts of Crocus species in Anatolia. Afric J Microbiol Res 4:1154–1161 Afifi MS (2003) A novel 4′-O-diglycoside of decarboxyrosmarinic acid from Blepharis ciliaris. Pharm Biol 41:487–490 Agata I, Hatano T, Nishibe S, Okuda T (1988) Rabdosiin, a new rosmarinic acid dimer with a lignan skeleton from Rabdosia japonica. Chem Pharm Bull 36:3223–3225 Agata I, Hatano T, Nishibe S, Okuda T (1989) A tetrameric derivative of caffeic acid from Rabdosia japonica. Phytochemistry 28:2447–2450 Ahmad A, Pandurangan A, Singh N, Ananad P (2012) A mini review on chemistry and biology of Hamelia patens (Rubiaceae). Pharmacogn J 4:1–4 Amzad Hossain M, Salehuddin SM, Kabir MJ, Rahman SMM, Rupasinghe HPV (2009) Sinensetin, rutin, 3′-hydroxy-5,6,7,4′-tetramethoxyflavone and rosmarinic acid contents and antioxidative effect of the skin of apple fruit. Food Chem 113:185–190 Amzad HM, Salehuddin SM, Mizanur RSM, Kabir MJ (2010) The effects of solvents on recovery of polyphenols from the pink Fuji apple skin. Afric J Food Agric Nutr Devel 10:2556–2569 Aquino R, Ciavatta ML, De Simone F, Pizza C (1990) A flavanone glycoside from Hamelia patens. Phytochemistry 29:2358–2360 Aquino R, Morelli S, Lauro MR, Abdo S, Saija A, Tomaino A (2001) Phenolic constituents and antioxidant activity of an extract of Anthurium versicolor leaves. J Nat Prod 64:1019–1023 Ariffin F, Heong Chew S, Bhupinder K, Karim AA, Huda N (2011) Antioxidant capacity and phenolic composition of fermented Centella asiatica herbal teas. J Sci Food Agric 91:2731–2739 Asakawa Y (1995) Chemical constituents of the bryophytes—chemical constituents of Anthocerotae (hornworts). In: Herz W, Kirby GW, Moore RE, Steglich W, Tamm C (eds) Progress in the chemistry of organic natural products. Springer, Wien, pp 460–464 Astani A, Reichling J, Schnitzler P (2012) Melissa officinalis extract inhibits attachment of Herpes simplex virus in vitro. Chemotherapy 58:70–77 Baczek K, Przybyl JL, Weglarz Z (2010) Intraspecific chemical variability of Eleutherococcus senticosus (Rupr. et Maxim.) Maxim Acta Hortic 869:119–122 Bassard JE, Ullmann P, Bernier F, Werck-Reichhart D (2010) Phenolamides: bridging polyamines to the phenolic metabolism. Phytochemistry 71:1808–1824 Berger A, Meinhard J, Petersen M (2006) Rosmarinic acid synthase is a new member of the superfamily of BAHD acyltransferases. Planta 224:1503–1510 Bohm BA (1968) Phenolic compounds in ferns—III. An examination of some ferns for caffeic acid derivatives. Phytochemistry 7:1825–1830 Boldizsár I, Szűcs Z, Füzfai Z, Molnár-Perl I (2006) Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography. J Chromatogr A 1133:259–274 Booth MPS, Conners R, Rumsby G, Brady RL (2006) Structural basis of substrate specificity in human glyoxylate reductase/hydroxypyruvate reductase. J Mol Biol 360:178–189 Bulgakov VP, Inyushkina YV, Fedoreyev SA (2012) Rosmarinic acid and its derivatives: biotechnology and applications. Crit Rev Biotechnol 32:203–217 Cantino PD, Harley RM, Wagstaff SJ (1992) Genera of Labiatae: status and classification. In: Hartley RM, Reynolds T (eds) Advances in Labiate sciences. Royal Botanic Gardens, Kew, pp 511–522 Chaprin N, Ellis BE (1984) Microspectrophotometric evaluation of rosmarinic acid accumulation in single cultured plant cells. Can J Bot 62:2278–2282 Cho YJ, Lee KH, Cha WS, Ju IS, Yun DH, An BJ, Lee SH, Kim MU, Kim JH, Chun SS (2009) Purification and identification of inhibitory compounds from Cheongmoknosang mulberry leaves (Morus alba L.) on Helicobacter pylori. J Appl Biol Chem 52:65–69 Clé C, Hill LM, Niggeweg R, Martin CR, Guisez Y, Prinsen E, Jansen MAK (2008) Modulation of chlorogenic acid biosynthesis in Solanum lycopersicon: consequences for phenolic accumulation and UV-tolerance. Phytochemistry 69:2149–2156 Comino C, Lanteri S, Portis E, Acquadro A, Romani A, Hehn A, Larbat R, Bourgaud F (2007) Isolation and functional characterization of a cDNA coding a hydroxycinnamoyltransferase involved in phenylpropanoid biosynthesis in Cynara cardunculus L. BMC Plant Biol 7:14 D’Auria JC (2006) Acyltransferases in plants: a good time to be BAHD. Curr Opin Plant Biol 9:331–340 De Tommasi N, De Simone F, De Feo V, Pizza C (1991) Phenylpropanoid glycosides and rosmarinic acid from Momordica balsamina. Planta Med 57:201 De-Eknamkul W, Ellis BE (1987a) Purification and characterization of tyrosine aminotransferase activities from Anchusa officinalis cell cultures. Arch Biochem Biophys 257:430–438 De-Eknamkul W, Ellis BE (1987b) Tyrosine aminotransferase: the entrypoint enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis. Phytochemistry 26:1941–1946 Douce R, Joyard J (1996) Biosynthesis of thylakoid membrane lipids. In: Ort DR, Yocum CF (eds) Oxygenic photosynthesis: the light reactions. Kluwer Academic Publishers, Dordrecht, pp 69–101 Duff RJ, Villarreal JC, Cargill DC, Renzaglia KS (2007) Progress and challenges toward developing a phylogeny and classification of the hornworts. Bryologist 110:214–243 Eberle D, Ullmann P, Werck-Reichhart D, Petersen M (2009) cDNA cloning and functional characterisation of CYP98A14 and NADPH:cytochrome P450 reductase from Coleus blumei involved in rosmarinic acid biosynthesis. Plant Mol Biol 69:239–253 Ehlting J, Hamberger B, Million-Rousseau R, Werck-Reichhart D (2006) Cytochromes P450 in phenolic metabolism. Phytochem Rev 5:239–270 El Dib RA, Marzouk MS, Moharram FA, El-Shenawy SM, Elazeem RM (2009) Chemical and biological investigation of Calothamnus quadrifidus R.Br. Bull Fac Pharm (Cairo University) 47:193–202 Ellis BE, Towers GHN (1970) Biogenesis of rosmarinic acid in Mentha. Biochem J 118:291–297 Erkan N (2012) Antioxidant activity and phenolic compounds of fractions from Portulaca oleracea L. Food Chem 133:775–781 Feng L, Wanninayake U, Strom S, Geiger J, Walker KD (2011) Mechanistic, mutational, and structural evaluation of a Taxus phenylalanine aminomutase. Biochemistry 50:2919–2930 Fernandez L, Martin T, Villaescusa L, Bartolome C, Rubio B, Diaz AM (1995) Rosmarinic acid and iridoids of Scrophularia scorodonia L. Colloques – Institut National de la Recherche Agronomique 69 Franke R, Humphreys JM, Hemm MR, Denault JW, Ruegger MO, Cusumano JC, Chapple C (2002) The Arabidopsis REF8 gene encodes the 3-hydroxylase of phenylpropanoid metabolism. Plant J 30:33–45 Gang DR, Beuerle T, Ullmann P, Werck-Reichhart D, Pichersky E (2002) Differential production of meta hydroxylated phenylpropanoids in Sweet Basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases. Plant Physiol 130:1536–1544 Gertlowski C, Petersen M (1993) Influence of the carbon source on growth and rosmarinic acid production in suspension cultures of Coleus blumei. Plant Cell Tiss Org Cult 34:183–190 Goldberg JD, Yoshida T, Brick P (1994) Crystal structure of a NAD-dependent d-glycerate dehydrogenase at 2.4 Å resolution. J Mol Biol 236:1123–1140 Grant GA (1989) A new family of 2-hydroxyacid dehydrogenases. Biochem Biophys Res Commun 165:1371–1374 Grayer RJ, Eckert MR, Veitch NC, Kite GC, Marin PD, Kokubun T, Simmonds MSJ, Paton AJ (2003) The chemotaxonomic significance of two bioactive caffeic acid esters, nepetoidins A and B, in the Lamiaceae. Phytochemistry 64:519–528 Guo D, Du G, Li L, Li R (2004) Inhibitory activities of rosmarinic acid against plant pathogenic fungi. Weishengwuxue Tongbao 31:71–76 Harborne JB (1966) Caffeic acid ester distribution in higher plants. Z Naturforsch 21b:604–605 Haslam E (1993) Shikimic acid—metabolism and metabolites. Wiley, Chichester Häusler E, Petersen M, Alfermann AW (1991) Hydroxyphenylpyruvate reductase from cell suspension cultures of Coleus blumei Benth. Z Naturforsch 46c:371–376 Häusler E, Petersen M, Alfermann AW (1992) Rosmarinsäure in Blechnum-Spezies. In: Haschke HP, Schnarrenberger C (eds) Botanikertagung 1992 Berlin. Akademie-Verlag, Berlin, p 507 Häusler E, Petersen M, Alfermann AW (1993) Isolation of protoplasts and vacuoles from cell suspension cultures of Coleus blumei Benth. Plant Cell Rep 12:510–512 Hawas UW, Ibrahim LF, Farrag ARH, Hussein JS, Elshiekh I (2009) Evaluation of antiulcer activity of Chenopodium moquinianum and kaempferol glycosides in rats. World J Chem 4:73–82 Heller W, Kühnl T (1985) Elicitor induction of a microsomal 5-O-(4-coumaroyl)shikimate 3′-hydroxylase in parsley cell suspension cultures. Arch Biochem Biophys 241:453–460 Hess JL (1993) Vitamin E, α-tocopherol. In: Alscher RG, Hess JL (eds) Antioxidants in higher plants. CRC, Boca Raton, pp 111–134 Hiller K (1965) Zur Kenntnis der Inhaltsstoffe einiger Saniculoidae. 1. Mitteilung: Sanicula europaea L.—Isolierung und quantitative Erfassung von Chlorogen- und Rosmarinsäure. Pharmazie 20:574–579 Hiller K, Kothe N (1967) Chlorogen- und Rosmarinsäure—Vorkommen und quantitative Verteilung in Pflanzen der Saniculoideae. Pharmazie 22:220–221 Hippolyte I, Marin B, Baccou JC, Jonard R (1992) Growth and rosmarinic acid production in cell suspension cultures of Salvia officinalis L. Plant Cell Rep 11:109–112 Ho LK, Chang CR, Chang YS (1995) Chemical components from Triumfetta bartramia. J Chin Chem Soc (Taipei) 42:93–95 Hoffmann L, Maury S, Martz F, Geoffroy P, Legrand M (2003) Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism. J Biol Chem 278:95–102 Holzmannová V (1995) Kyselina rosmarinová a její biologická aktivita. Chem Listy 90:486–496 Hörhammer L, Wagner H, Schilcher H (1962) Zur Kenntnis der Inhaltsstoffe von Lycopus europaeus 1. Mitteilung: Über die Inhaltsstoffe von Arzneipflanzen mit hormon- und antihormonähnlicher Wirkung. Arneimittelforschung 12:1–7 Hounsome N, Hounsome B, Tomos D, Edwards-Jones G (2009) Changes in antioxidant compounds in white cabbage during winter storage. Postharvest Biol Tec 52:173–179 Hu H, Wang G, Liu J, Cao H, Zheng X (2006) Studies on phenolic compounds from Polygonum aviculare. Zhongguo Zhongyao Zazhi 31:740–742 Hu Y, Gai Y, Yin L, Wang X, Feng C, Feng L, Li D, Jiang XN, Wang DC (2010) Crystal structures of a Populus tomentosa 4-coumarate: CoA ligase shed light on its enzymatic mechanisms. Plant Cell 22:3093–3104 Huang HL, Li DL, Li XM, Xu B, Wang BG (2007) Antioxidative principals of Jussiaea repens: an edible medicinal plant. Int J Food Sci Technol 42:1219–1227 Huang B, Duan Y, Yi B, Sun L, Yu X, Sun H, Zhang H, Chen W (2008a) Characterization and expression profiling of cinnamate 4-hydroxylase gene from Salvia miltiorrhiza in rosmarinic acid biosynthesis pathway. Russ J Plant Physiol 55:390–399 Huang B, Yi B, Duan Y, Sun L, Yu X, Guo J, Chen W (2008b) Characterization and expression profiling of tyrosine aminotransferase gene from Salvia miltiorrhiza (Dan-shen) in rosmarinic acid biosynthesis pathway. Mol Biol Rep 35:601–612 Huang Y, Chen Y, Wen Y, Li D, Chen W, Liu J, Lu F (2010) Chemical constituents of Picria fel-terrae. Guangxi Zhiwu 30:887–890 Hücherig S (2010) RNAi-Untersuchungen und Überexpression von Genen der Rosmarinsäurebiosynthese. Dissertation, Philipps-Universität Marburg Hücherig S, Petersen M (2012) RNAi suppression and overexpression studies of hydroxyphenylpyruvate reductase (HPPR) and rosmarinic acid synthase (RAS) genes related to rosmarinic acid biosynthesis in hairy root cultures of Coleus blumei. Plant Cell Tiss Org Cult. doi:10.1007/s11240-012-0277-8 Janiak V, Petersen M, Zentgraf M, Klebe G, Heine A (2010) Structure and substrate docking of a hydroxy(phenyl)pyruvate reductase from the higher plant Coleus blumei Benth. Acta Cryst D66:593–603 Janicsák G, Máthé I, Miklóssy-Vári V, Blunden G (1999) Comparative studies of the rosmarinic and caffeic acid contents of Lamiaceae species. Biochem Syst Ecol 27:733–738 Jiang RW, Lau KM, Hon PM, Mak TCW, Woo KS, Fung KP (2005) Chemistry and biological activities of caffeic acid derivatives from Salvia miltiorrhiza. Curr Med Chem 12:237–246 Kanlayavattanakul M, Lourith N (2012) Biologically active phenolics in seed coat of three sweet Tamarindus indica varieties grown in Thailand. Adv Sci Engin Med 4:511–516 Kanlayavattanakul M, Ospondpant D, Ruktanonchai U, Lourith N (2012) Biological activity assessment and phenolic compounds characterization from the fruit pericarp of Litchi chinensis for cosmetic applications. Pharm Biol 50:1384–1390 Kelley CJ, Mahajan JR, Brooks LC, Neubert LA, Breneman WR, Carmack M (1975) Polyphenolic acids of Lithospermum ruderale Dougl. ex Lehm. (Boraginaceae). 1. Isolation and structure determination of lithospermic acid. J Org Chem 40:1804–1815 Kelley CJ, Harruff RC, Carmack M (1976) The polyphenolic acids of Lithospermum ruderale. II. Carbon-13 nuclear magnetic resonance of lithospermic and rosmarinic acids. J Org Chem 41:449–455 Kim KH, Janiak V, Petersen M (2004) Purification, cloning and functional expression of hydroxyphenylpyruvate reductase involved in rosmarinic acid biosynthesis in cell cultures of Coleus blumei. Plant Mol Biol 54:311–323 Kochan E, Wyoskinska H, Chmiel A, Grabias B (1999) Rosmarinic acid and other phenolic acids in hairy roots of Hyssopus officinalis. Z Naturforsch 54c:11–16 Kowalczyk A (1996) HPLC analysis of polyphenolic compounds in Knautia arvensis Coult. Beitr Züchtungsforsch 2:389–392 Kühnl T, Koch U, Heller W, Wellmann E (1987) Chlorogenic acid biosynthesis: characterization of a light-induced microsomal 5-O-(4-coumaroyl)-d-quinate/shikimate 3′-hydroxylase from carrot (Daucus carota L.) cell suspension cultures. Arch Biochem Biophys 258:226–232 Kumaraswamy GK, Bollina V, Kushalappa AC, Choo TM, Dion Y, Rioux S, Mamer O, Faubert D (2011) Metabolomics technology to phenotype resistance in barley against Gibberella zeae. Eur J Plant Pathol 130:29–43 Kuzma L, Wysokinska H (2003) Production of secondary metabolites in shoots of Salvia nemorosa L. cultured in vitro. Biotechnologia 4:154–159 Lallemand LA, McCarthy JG, McSweeney S, McCarthy AA (2012a) Purification, crystallization and preliminary x-ray diffraction analysis of a hydroxycinnamoyl-CoA shikimate/quinate hydroxycinnamoyltransferase (HCT) from Coffea canephora involved in chlorogenic acid biosynthesis. Acta Cryst F68:824–828 Lallemand LA, Zubieta C, Lee SG, Wang Y, Acajjaoui S, Timmins J, McSweeney S, Jez JM, McCarthy JG, McCarthy AA (2012b) A structural basis for the biosynthesis of the major chlorogenic acids found in coffee. Plant Physiol 160:249–260 Landmann C, Hücherig S, Fink B, Hoffmann T, Dittlein D, Coiner HA, Schwab W (2011) Substrate promiscuity of a rosmarinic acid synthase from lavender (Lavandula angustifolia L.). Planta 234:305–320 Lasure A, Van Poel B, Pieters L, Claeys M, Gupta M, Vanden Berghe D, Vlietinck AJ (1994) Complement-inhibiting properties of Apeiba tibourbou. Planta Med 60:276–277 Le Claire E, Schwaiger S, Banaigs B, Stuppner H, Gafner F (2005) Distribution of a new rosmarinic acid derivative in Eryngium alpinum L. and other Apiaceae. J Agric Food Chem 53:4367–4372 Lee KH, Yang MC, Kim KH, Kwon HC, Choi SU, Lee KR (2008) A new phenolic amide from the roots of Paris verticillata. Molecules 13:41–45 Lee HJ, Yang SW, Park SR, Yang JH, Chae BS, Eun JS, Jeon H, Lim JP, Hwang YH, Park JH, Kim DK (2009) Antioxidative constituents of Cyperus difformis L. Nat Prod Sci 15:241–245 Li X, Zhang Y, Yang L, Feng Y, Liu Y, Zeng X (2012) Studies of phenolic acid constituents from the whole plant of Sarcandra glabra. Zhongyao Xinyao Yu Linchuang Yaoli 23:295–298 Litvinenko VI, Popova TP, Simonjan AV, Zoz IG, Sokolov VS (1975) “Gerbstoffe” und Oxyzimtsäureabkömmlinge in Labiaten. Planta Med 27:372–380 Lu Y, Foo Y (1999) Rosmarinic acid derivatives from Salvia officinalis. Phytochemistry 51:91–94 Lu Y, Foo LY, Wong H (1999) Sagecoumarin, a novel caffeic acid trimer from Salvia officinalis. Phytochemistry 52:1149–1152 Ly TN, Shimoyamada M, Yamauchi R (2006) Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth. leaves and their antioxidative activity. J Agric Food Chem 54:3786–3793 Males Z, Plazibat M (2000) Investigation of chemical composition of Zostera noltii Hornem. Farmaceutski Glasnik 56:109–118 Maskovic P, Solujic S, Mihailovic V, Mladenovic M, Cvijovic M, Mladenovic J, Acamovic-Dokovic G, Kurcubic V (2011) Phenolic compounds and biological activity of Kitaibelia vitifolia. J Med Food 14:1617–1623 Matsuno M, Nagatsu A, Ogihara Y, Ellis BE, Mizukami H (2002) CYP98A6 from Lithospermum erythrorhizon encodes 4-coumaroyl-4′-hydroxyphenyllactic acid 3-hydroxylase involved in rosmarinic acid biosynthesis. FEBS Lett 514:219–224 Mau CJ, Karp F, Ito M, Honda G, Croteau RB (2010) A candidate cDNA clone for (−)-limonene-7-hydroxylase from Perilla frutescens. Phytochemistry 71:373–379 Mazzanti G, Battinelli L, Pompeo C, Serrilli AM, Rossi R, Sauzullo I, Mengoni F, Vullo V (2008) Inhibitory activity of Melissa officinalis L. extract on Herpes simplex virus type 2 replication. Nat Prod Res 22:1433–1440 Melillo de Magalhaes P, Dupont I, Hendrickx A, Joly A, Raas T, Dessy S, Sergent T, Schneider YJ (2012) Anti-inflammatory effect and modulation of cytochrome P450 activities by Artemisia annua tea infusions in human intestinal Caco-2 cells. Food Chem 134:864–871 Míka V, Kubáň V, Klejdus B, Odstrčilová V, Nerušil P (2005) Phenolic compounds as chemical markers of low taxonomic levels in the family Poaceae. Plant Soil Environm 51:506–512 Morant M, Schoch GA, Ullmann P, Ertunc T, Little D, Olsen CE, Petersen M, Negrel J, Werck-Reichhart D (2007) Catalytic activity, duplication and evolution of the CYP98 cytochrome P450 family in wheat. Plant Mol Biol 63:1–19 Murakami Y, Omoto T, Asai I, Shimomura K, Yoshihira K, Ishimaru K (1998) Rosmarinic acid and related phenolics in hairy root cultures of Hyssopus officinalis. Plant Cell Tiss Org Cult 53:75–78 Nickrent DL, Parkinson CL, Palmer JD, Duff RJ (2000) Multigene phylogeny of land plants with special reference to bryophytes and the earliest land plants. Mol Biol Evol 17:1885–1895 Niggeweg R, Michael AJ, Martin C (2004) Engineering plants with increased levels of the antioxidant chlorogenic acid. Nature Biotechnol 22:746–754 Nishizawa M, Tsuda M, Hayashi K (1990) Two caffeic acid tetramers having enantiomeric phenyldihydronaphthalene moieties from Macrotomia euchroma. Phytochemistry 29:2645–2649 Ogata A, Tsuruga A, Matsuno M, Mizukami H (2004) Elicitor-induced rosmarinic acid biosynthesis in Lithospermum erythrorhizon cell suspension cultures: activities of rosmarinic acid synthase and the final two cytochrome P450-catalyzed hydroxylations. Plant Biotechnol 21:393–396 Olivier DK, van Wyk BE, van Heerden FR (2008) The chemotaxonomic and medicinal significance of phenolic acids in Arctopus and Alepidea (Apiaceae subfamily Saniculoideae). Biochem Syst Ecol 36:724–729 Parejo I, Viladomat F, Bastida J, Schmeda-Hirschmann G, Burillo J, Codina C (2004) Bioguided isolation and identification of the nonvolatile antioxidant compounds from fennel (Foeniculum vulgare Mill.) Waste. J Agric Food Chem 52:1890–1897 Parnham MJ, Kesselring K (1985) Rosmarinic acid. Drugs Fut 10:756–757 Petersen MS (1991) Characterization of rosmarinic acid synthase from cell cultures of Coleus blumei. Phytochemistry 30:2877–2881 Petersen M (1997) Cytochrome P-450-dependent hydroxylation in the biosynthesis of rosmarinic acid in Coleus. Phytochemistry 45:1165–1172 Petersen M (2003) Cinnamic acid 4-hydroxyase from cell cultures of the hornwort Anthoceros agrestis. Planta 217:96–101 Petersen M, Alfermann AW (1988) Two new enzymes of rosmarinic acid biosynthesis from cell cultures of Coleus blumei: hydroxyphenylpyruvate reductase and rosmarinic acid synthase. Z Naturforsch 43c:501–504 Petersen M, Simmonds MSJ (2003) Molecules of interest: rosmarinic acid. Phytochemistry 62:121–125 Petersen M, Häusler E, Karwatzki B, Meinhard J (1993) Proposed biosynthetic pathway for rosmarinic acid in cell cultures of Coleus blumei Benth. Planta 189:10–14 Petersen M, Abdullah Y, Benner J, Eberle D, Gehlen K, Hücherig S, Janiak V, Kim KH, Sander M, Weitzel C, Wolters S (2009) Evolution of rosmarinic acid biosynthesis. Phytochemistry 70:1663–1679 Petersen M, Hans J, Matern U (2010) Biosynthesis of phenylpropanoids and related compounds. In: Wink M (ed) Annual plant reviews—Biochemistry of plant secondary metabolism. Wiley-Blackwell, Chichester, pp 182–257 Ravn H, Pedersen MF, Andary JBC, Anthoni U, Christophersen C, Nielsen PH (1994) Seasonal variation and distribution of two phenolic compounds, rosmarinic acid and caffeic acid, in leaves and roots-rhizomes of eelgrass (Zostera marina L.). Ophelia 40:51–61 Razzaque A, Ellis BE (1977) Rosmarinic acid production in Coleus cell cultures. Planta 137:287–291 Rebey IB, Bourgou S, Ben Slimen Debez I, Karoui IJ, Hamrouni Sellami I, Msaada K, Limam F, Marzouk B (2012) Effects of extraction solvents and provenances on phenolic contents and antioxidant activities of cumin (Cuminum cyminum L.) seeds. Food Bioprocess Technol 5:2827–2836 Ritter H, Schulz GE (2004) Structural basis for the entrance into the phenylpropanoid metabolism catalyzed by phenylalanine ammonia-lyase. Plant Cell 16:3426–3436 Rubio B, Diaz AM, Martin T, Zaragoza F, Villaescusa L (1992) Phenolic compounds in Scolymus hispanicus L. Ars Pharm 33:462–465 Sander M, Petersen M (2011) Distinct substrate specificities and unusual substrate flexibilities of two hydroxycinnamoyltransferases, rosmarinic acid synthase and hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyltransferase, from Coleus blumei Benth. Planta 233:1157–1171 Satake T, Kamiya K, Saiki Y, Hama T, Fujimoto Y, Kitanaka S, Kimura Y, Uzawa J, Endang H, Umar M (1999) Studies on the constituents of fruits of Helicteres isora L. Chem Pharm Bull 47:1444–1447 Scarpati ML, Oriente G (1958) Isolamento e costituzione dell’acido rosmarinico (dal rosmarinus off.). Ric Sci 28:2329–2333 Schoch G, Goepfert S, Morant M, Hehn A, Meyer D, Ullmann P, Werck-Reichhart D (2001) CYP98A3 from Arabidopsis thaliana is a 3′-hydroxylase of phenolic esters, a missing link in the phenylpropanoid pathway. J Biol Chem 276:36566–36574 Song J, Wang Z (2009) Molecular cloning, expression and characterization of a phenylalanine ammonia-lyase gene (SmPAL1) from Salvia miltiorrhiza. Mol Biol Rep 36:939–952 Souza SMM, Moraes CSS, Couto RO, Gil ES, Fonseca YM, Conceicao EC (2012) In vitro antioxidant activity of Apeiba tibourbou Aubl. (Tiliaceae): a powerful antioxidant source of rosmarinic acid. J Pharm Res 5:1414–1417 St. Pierre B, De Luca V (2000) Evolution of acyltransferase genes: origin and diversification of the BAHD superfamily of acyltransferases involved in secondary metabolism. Rec Adv Phytochem 34:285–316 Štěrbová D, Vlček J, Kubáň V (2006) Capillary zone electrophoretic determination of phenolic compounds in chess (Bromus inermis L.) plant extracts. J Sep Sci 29:308–313 Szabo E (1994) Lokalisation, Transport und Akkumulation von Rosmarinsäure in Zellkulturen von Coleus blumei. Dissertation, Heinrich-Heine-Universität Düsseldorf Szabo E, Thelen A, Petersen M (1999) Fungal elicitor preparations and methyl jasmonate enhance rosmarinic acid accumulation in suspension cultures of Coleus blumei. Plant Cell Rep 18:485–489 Tada H, Murakami Y, Omoto T, Shimomura K, Ishimaru K (1996) Rosmarinic acid and related phenolics in hairy root cultures of Ocimum basilicum. Phytochemistry 42:431–434 Takeda R, Hasegawa J, Shinozaki M (1990) The first isolation of lignans, megacerotonic acid and anthocerotonic acid, from non-vascular plants, Anthocerotae (hornworts). Tetrahedron Lett 31:4159–4162 Tanaka T, Morimoto S, Nonaka G, Nishioka I, Yokozawa T, Chung HY, Oura H (1989) Magnesium and ammonium-potassium lithospermates B, the active principles having a uremia-preventive effect from Salvia miltiorrhiza. Chem Pharm Bull 37:340–344 Tanaka T, Nishimura A, Kouno I, Nonaka G, Young TJ (1996) Isolation and characterization of yunnaneic acids A-D, four novel caffeic acid metabolites from Salvia yunnanensis. J Nat Prod 59:843–849 Timm S, Nunes-Nesi A, Pärnik T, Morgenthal K, Wienkoop S, Keerberg O, Weckwerth W, Kleczkowski LA, Fernie AR, Bauwe H (2008) A cytosolic pathway for the conversion of hydroxypyruvate to glycerate during photorespiration in Arabidopsis. Plant Cell 20:2848–2859 Trennheuser F (1992) Phytochemische Untersuchung und in vitro Kultur ausgewählter Vertreter der Anthocerotopsida. Dissertation, University of Saarbrücken Trennheuser F, Burkhard G, Becker H (1994) Anthocerodiazonin, an alkaloid from Anthoceros agrestis. Phytochemistry 37:899–903 Trute A, Nahrstedt A (1996) Separation of rosmarinic acid enantiomers by three different chromatographic methods (HPLC, CE, GC) and the determination of rosmarinic acid in Hedera helix L. Phytochem Anal 7:204–208 Tsumbu CN, Deby-Dupont G, Tits M, Angenot L, Frederich M, Kohnen S, Mouithys-Mickalad A, Serteyn D, Franck T (2012) Polyphenol content and modulatory activities of some tropical dietary plant extracts on the oxidant activities of neutrophils and myeloperoxidase. Int J Mol Sci 13:628–650 Ulbrich B, Wiesner W, Arens H (1985) Large-scale production of rosmarinic acid from plant cell cultures of Coleus blumei Benth. In: Neumann KH, Barz W, Reinhard E (eds) Primary and secondary metabolism of plant cell cultures. Springer, Berlin, pp 293–303 Umezawa T (2010) The cinnamate/monolignol pathway. Phytochem Rev 9:1–17 Velazquez Fiz MP, Diaz Lanza AM, Fernandez Matellano L (2000) Polyphenolic compounds from Plantago lagopus L. Z Naturforsch 55c:877–880 Vilnet AA, Konstantinova NA, Troitsky AV (2009) Genosystematics and new insight into the phylogeny and taxonomy of liverworts. Mol Biol 43:783–793 Vogelsang K, Schneider B, Petersen M (2006) Production of rosmarinic acid and a new rosmarinic acid 3′-O-β-d-glucoside in suspension cultures of the hornwort Anthoceros agrestis Paton. Planta 223:369–373 Wang BQ (2010) Salvia miltiorrhiza: chemical and pharmacological review of a medicinal plant. J Med Plants Res 4:2813–2820 Wang FY, Li D, Han ZC, Gao HY, Wu LJ (2007) Chemical constituents of Rhodiola rosea and inhibitory effect on UV-induced A375–S2 cell death. Shenyang Yaoke Daxue Xuebao 24(280–283):287 Weitzel C, Petersen M (2010) Enzymes of phenylpropanoid metabolism in the important medicinal plant Melissa officinalis L. Planta 232:731–742 Weitzel C, Petersen M (2011) Cloning and characterisation of rosmarinic acid synthase from Melissa officinalis L. Phytochemistry 72:572–578 Wölbling RH, Leonhardt K (1994) Local therapy of Herpes simplex with dried extracts from Melissa officinalis. Phytomedicine 1:25–31 Wu B, Szymanski W, Wybenga GG, Heberling MM, Bartsch S, De Wildeman S, Poelarends GJ, Feringa BL, Dijkstra BW, Janssen DB (2012) Mechanism-inspired engineering of phenylalanine aminomutase for enhanced β-regioselective asymmetric amination of cinnamates. Angew Chem Int Ed Engl 51:482–486 Xiao Y, Gao S, Di P, Chen J, Chen W, Zhang L (2009) Methyl jasmonate dramatically enhances the accumulation of phenolic acids in Salvia miltiorrhiza hairy root cultures. Physiol Plantarum 137:1–9 Yamamura Y, Ogihara Y, Mizukami H (2001) Cinnamic acid 4-hydroxylase from Lithospermum erythrorhizon: cDNA cloning and gene expression. Plant Cell Rep 2:655–662 Yazaki K, Ogawa A, Tabata M (1995) Isolation and characterization of two cDNAs encoding 4-coumarate:CoA ligase in Lithospermum cell cultures. Plant Cell Physiol 36:1319–1329 Yazaki K, Kataoka M, Honda G, Severin K, Heide L (1997) cDNA cloning and gene expression of phenylalanine ammonia-lyase in Lithospermum erythrorhizon. Biosci Biotechnol Biochem 61:1995–2003 Yoshida M, Fuchigami M, Nagao T, Okabe H, Matsunaga K, Takata J, Karube Y, Tsuchihashi R, Kinjo J, Mihashi K, Fujioka T (2005) Antiproliferative constituents from Umbelliferae plants VII. Active triterpenes and rosmarinic acid from Centella asiatica. Biol Pharm Bull 28:173–175 Yun YS, Satake M, Katsuki S, Kunugi A (2004) Phenylpropanoid derivatives from edible canna, Canna edulis. Phytochemistry 65:2167–2171 Zadra M, Piana M, Faccim de Brum T, Augusti Boligon A, Borba de Freitas R, Mansur Machado M, Terra Stefanello S, Antunes Soares FA, Linde Athayde M (2012) Antioxidant activity and phytochemical composition of the leaves of Solanum guaraniticum A. St.-Hil. Molecules 17:12560–12574 Zenk MH, El-Shagi H, Ulbrich B (1977) Production of rosmarinic acid by cell-suspension cultures of Coleus blumei. Naturwissenschaften 64:585–586 Zhang J, Wang ZW, Mi Q (2011) Phenolic compounds from Canna edulis Ker residue and their antioxidant activity. Food Sci Technol-LEB 44:2091–2096 Zhao SJ, Hu ZB, Liu D, Leung FCC (2006) Two divergent members of 4-coumarate: coenzyme A ligase from Salvia miltiorrhiza Bunge: cDNA cloning and functional study. J Integr Plant Biol 48:1355–1364 Zheng Q, Sun Z, Zhang X, Yuan J, Wu H, Yang J, Xu X (2012) Clerodendranoic acid, a new phenolic acid from Clerodendranthus spicatus. Molecules 17:13656–13661 Zhu L, Li Y, Yang J, Zuo L, Zhang D (2008) Studies on chemical constituents of Sarcandra glabra. Zhongguo Zhongyao Zazhi 33:155–157