Abstract
Suspension cultures of Coleus blumei accumulate very high amounts of rosmarinic acid, an ester of caffeic acid and 3,4-dihydroxyphenyllactate, in medium with elevated sucrose concentrations. Since the synthesis of this high level of rosmarinic acid occurs in only five days of the culture period, the activities of the enzymes involved in the biosynthesis are very high. Therefore all the enzymes necessary for the formation of rosmarinic acid from the precursors phenylalanine and tyrosine could be isolated from cell cultures of Coleus blumei: phenylalanine ammonia-lyase, cinnamic acid 4-hydroxylase, hydroxycinnamoyl:CoA ligase, tyrosine aminotransferase, hydroxyphenylpyruvate reductase, rosmarinic acid synthase and two microsomal 3- and 3′-hydroxylases. The main characteristics of these enzymes of the proposed biosynthetic pathway of rosmarinic acid will be described.
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Abbreviations
- DHPL:
-
3,4-dihydroxyphenyllactate
- DHPP:
-
3,4-dihydroxyphenylpyruvate
- pHPL:
-
4-hydroxyphenyllactate
- pHPP:
-
4-hydroxyphenylpyruvate
- RA:
-
rosmarinic acid
References
Benveniste I, Salaün JP & Durst F (1977) Wounding-induced cinnamic acid hydroxylase in Jerusalem artichoke tuber. Phytochemistry 16: 69–73
Benveniste I, Salaün JP, Simon A, Reichhardt D & Durst F (1982) Cytochrome P-450-dependent ω-hydroxylation of lauric acid by microsomes of pea seedlings. Plant Physiol. 70: 122–126
Boniwell JM & Butt VS (1986) Flavine nucleotide dependent 3-hydroxylation of 4-hydroxyphenylpropanoid carboxylic acids by particulate preparations from potato tubers. Z. Naturforsch. 41c: 56–60
Butt VS (1985) Oxygenation and oxidation in the metabolism of aromatic compounds. In: Van Sumere CF & Lea PJ (Eds) The Biochemistry of Plant Phenolics (pp 349–365). Clarendon Press, Oxford
De-Eknamkul W & Ellis BE (1987a) Tyrosine aminotransferase: the entrypoint enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis. Phytochemistry 26: 1941–1946
De-Eknamkul W & Ellis BE (1987b) Purification and characterization of tyrosine aminotransferase activities from Anchusa officinalis cell cultures. Arch. Biochem. Biophys. 257: 430–438
De-Eknamkul W & Ellis BE (1988) Rosmarinic acid: production in plant cell cultures. In: Bajaj YPS (Ed) Biotechnology in Agriculture and Forestry, Vol 4, Medicinal and Aromatic Plants I (pp 310–329). Springer-Verlag, Berlin, Heidelberg
Ellis BE, Remmen S & Goeree G (1979) Interactions between parallel pathways during biosynthesis of rosmarinic acid in cell suspension cultures of Coleus blumei. Planta 147: 163–167
Ellis BE & Towers GHN (1970) Biogenesis of rosmarinic acid in Mentha. Biochem. J. 118: 291–297
Forkmann G, Heller W & Grisebach H (1980) Anthocyanin biosynthesis in flowers of Matthiola incana. Flavanone 3- and flavonoid 3′-hydroxylases. Z. Naturforsch. 35c: 691–695
Friedrich CA, Morizot DC, Siciliano MJ & Ferell RE (1987) The reduction of aromatic alpha-keto acids by cytoplasmatic malate dehydrogenase and lactate dehydrogenase. Biochem. Genet. 25: 657–669
Friedrich CA, Ferell RE, Siciliano MJ & Kitto GB (1988) Biochemical and genetic identity of alpha-keto reductase and cytoplasmatic malate dehydrogenase from human erythrocytes. Ann. Hum. Gen. 52: 25–37
Gamborg OL, Miller RA & Ojima K (1968) Nutrient requirements of suspension cultures of soybean root cells. Exp. Cell Res. 50: 151–158
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
Hagmann ML, Heller W & Grisebach H (1983) Induction and characterization of a microsomal flavonoid 3′-hydroxylase from parsley cell cultures. Eur. J. Biochem 134: 547–554
Harborne JB (1966) Caffeic acid ester distribution in higher plants. Z. Naturforsch. 21 b: 604–605
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 (p 507). Akademie Verlag, Berlin
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
Kamsteeg J, van Brederode J, Verschuren PM & van Nigtevecht G (1981) Identification, properties and genetic control of p-coumaroyl-coenzyme A 3-hydroxylase isolated from petals of Silene dioica. Z. Pflanzenphysiol. 102: 435–442
Karwatzki B (1992) Biochemische und immunchemische Untersuchungen zur Hydroxyzimtsäure:CoA Ligase aus rosmarinsäurebildenden Zellkulturen von Coleus blumei Benth. Doctoral thesis, University of Düsseldorf
Karwatzki B, Petersen M & Alfermann AW (1989) Transient activity of enzymes involved in the biosynthesis of rosmarinic acid in cell suspension cultures of Coleus blumei. Planta Med. 55: 663–664
Kneusel RE, Matern U & Nicolay K (1989) Formation of trans-caffeoyl-CoA from trans-4-coumaroyl-CoA by Zn2+-dependent enzymes in cultured plant cells and its activation by an elicitor-induced pH-shift. Arch. Biochem. Biophys. 269: 455–462
Kojima M & Takeuchi W (1989) Detection and characterization of p-coumaric acid hydroxylase in mung bean, Vigna mungo, seedlings. J. Biochem. 105: 265–270
Kojima M & Villegas RJA (1984) Detection of the enzyme in sweet potato which catalyzes trans-esterification between 1-O-p-coumaroyl-d-glucose and d-quinic acid. Agric. Biol. Chem. 48: 2397–2399
Kreuzaler F & Hahlbrock K (1972) Enzymatic synthesis of aromatic compounds in higher plants: formation of naringenin (5,7,4′-trihydroxyflavanone) from p-coumaroyl-coenzyme A and malonyl-coenzyme A. FEBS Letters 28: 69–72
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
Larson RL & Bussard JB (1986) Microsomal flavonoid 3′-hydroxylase from maize seedlings. Plant Physiol. 80: 483–486
Litvinenko VI, Popova TP, Simonjan AV, Zoz IG & Sokolov VS (1975) “Gerbstoffe” und Oxyzimtsäureabkömmlinge in Labiaten. Planta Med. 27: 372–380
Lloyd AM, Walbot V & Davis RW (1992) Arabidopsis and Nicotiana anthocyanin production activated by maize regulators R and Cl. Science 258: 1773–1775
Meinhard J, Petersen M & Alfermann AW (1992) Purification of hydroxyphenylpyruvate reductase from cell cultures of Coleus blumei. Planta Med. 58: A598-A599
Mizukami H & Ellis BE (1991) Rosmarinic acid formation and differential expression of tyrosine aminotransferase isoforms in Anchusa officinalis cell suspension cultures. Plant Cell Rep. 10: 321–324
Mölgaard P & Ravn H (1988) Evolutionary aspects of caffeoyl ester distribution in dicotyledons. Phytochemistry 27: 2411–2421
Petersen M (1991) Characterization of rosmarinic acid synthase from cell cultures of Coleus blumei. Phytochemistry 30: 2877–2881
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, 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 & Metzger JW (1993) Identification of the reaction products of rosmarinic acid synthase from cell cultures of Coleus blumei by ion spray mass spectrometry and tandem mass spectrometry. Phytochem. Anal., 4: 131–134
Razzaque A & Ellis BE (1977) Rosmarinic acid production in Coleus cell cultures. Planta 137: 287–291
Scarpati ML & Oriente G (1958) Isolamento e costituzione dell'acido rosmarinico (dal Rosmarinus off.). Ric. Sci. 28: 2329–2333
Scarpati ML & Oriente G (1960) Costituzione stereochimica dell'acido β(3,4-diossifenil)α-lattico dal Rosmarinus off.. Ric. Sci. 30: 255–259
Stöckigt J & Zenk MH (1974) Enzymatic synthesis of chlorogenic acid from caffeoyl coenzyme A and quinic acid. FEBS Letters 42: 131–134
Stotz G & Forkmann G (1982) Hydroxylation of the B-ring of flavonoids in the 3′- and 5′-position with enzyme extracts from flowers of Verbena hybrida. Z. Naturforsch. 37c: 19–23
Strack D, Gross W, Wray V & Grotjahn L (1987) Enzymic synthesis of caffeoylglucaric acid from chlorogenic acid and glucaric acid by a protein preparation from tomato cotyledons. Plant Physiol. 83: 475–478
Takeda R, Hasegawa J & Sinozaki K (1990) Phenolic compounds from Anthocerotae. In: Zinsmeister HD & Mues R (Eds) Bryophytes. Their chemistry and chemical taxonomy (pp 201–207). Oxford Science Publications, Oxford
Tkotz N & Strack D (1980) Enzymatic synthesis of sinapoyl-1-malate from 1-sinapoylglucose and 1-malate by a protein preparation from Raphanus sativus cotyledons. Z. Naturforsch. 35c: 835–837
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 (pp 293–303). Springer-Verlag, Berlin, Heidelberg
Villegas RJA, Shimokawa T, Okuyama H & Kojima M (1987) Purification and characterization of chlorogenic acid:chlorogenate caffeoyl transferase in sweet potato roots. Phytochemistry 26: 1577–1581
Zenk MH (1991) Chasing the enzymes of secondary metabolism: Plant cell cultures as a pot of gold. Phytochemistry 30: 3861–3863
Zenk MH, El-Shagi H & Ulbrich B (1977) Production of rosmarinic acid by cell-suspension cultures of Coleus blumei. Naturwissenschaften 64: 585–586
Zinsmeister HD, Becker H & Eicher T (1991) Moose, eine Quelle biologisch aktiver Naturstoffe? Angew. Chemie 103: 134–151
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Petersen, M., Häusler, E., Meinhard, J. et al. The biosynthesis of rosmarinic acid in suspension cultures of Coleus blumei . Plant Cell Tiss Organ Cult 38, 171–179 (1994). https://doi.org/10.1007/BF00033875
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DOI: https://doi.org/10.1007/BF00033875