Enzymes of phenylpropanoid metabolism in the important medicinal plant Melissa officinalis L

Planta

Volumn 232, Issue 3, 2010, Pages 731-742

  Weitzel, Corinna ^a   Petersen, Maike ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

4 Coumarate:CoA ligase (4CL); Melissa; Phenylalanine ammonia lyase (PAL); Phenylpropanoid metabolism; Rosmarinic acid

Indexed keywords

4 COUMARATE COA LIGASE; 4-COUMARATE-COA LIGASE; COMPLEMENTARY DNA; LONG CHAIN FATTY ACID COENZYME A LIGASE; PHENYLALANINE AMMONIA LYASE; PHENYLPROPIONIC ACID DERIVATIVE; PRIMER DNA;

ARTICLE; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION PROFILING; GENETICS; MEDICINAL PLANT; MELISSA OFFICINALIS; METABOLISM; NUCLEOTIDE SEQUENCE; PLANT GENE; POLYMERASE CHAIN REACTION; SOUTHERN BLOTTING;

BASE SEQUENCE; BLOTTING, SOUTHERN; COENZYME A LIGASES; DNA PRIMERS; DNA, COMPLEMENTARY; ESCHERICHIA COLI; GENE EXPRESSION PROFILING; GENES, PLANT; MELISSA; PHENYLALANINE AMMONIA-LYASE; PHENYLPROPIONATES; PLANTS, MEDICINAL; POLYMERASE CHAIN REACTION;

CITRUS LIMON; ESCHERICHIA COLI; LAMIACEAE; MAGNOLIOPHYTA; MELISSA; MELISSA OFFICINALIS;

EID: 77954535498     PISSN: 00320935     EISSN: 14322048     Source Type: Journal    
DOI: 10.1007/s00425-010-1206-x     Document Type: Article

References (60)

1. Becker-André M, Schulze-Lefert P, Hahlbrock K (1991) Structural comparison, modes of expression, and putative cis-acting elements of the two 4-coumarate: CoA ligase genes in potato. J Biol Chem 266: 8551-8559.
2. Berger A, Meinhard J, Petersen M (2006) Rosmarinic acid synthase is a new member of the superfamily of BAHD acyltransferases. Planta 224: 1503-1510.
3. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254.
4. Carnat AP, Carnat A, Fraisse D, Lamaison JL (1998) The aromatic and polyphenolic composition of lemon balm (Melissa officinalis L. subsp. officinalis) tea. Pharm Acta Helv 72: 301-305.
5. Chang A, Lim MH, Lee SW, Robb EJ, Nazar RN (2008) Tomato phenylalanine ammonia-lyase gene family, highly redundant but strongly underutilized. J Biol Chem 283: 33591-33601.
6. Chomczynski P, Sacchi N (1987) Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal Biochem 162: 156-159.
7. Cochrane FC, Davin LB, Lewis NG (2004) The Arabidopsis phenylalanine ammonia lyase gene family: kinetic characterization of the four PAL isoforms. Phytochemistry 65: 1557-1564.
8. Cramer CL, Edwards K, Dron M, Liang X, Dildine SL, Bolwell GP, Dixon RA, Lamb CJ, Schuch W (1989) Phenylalanine ammonia-lyase gene organization and structure. Plant Mol Biol 12: 367-383.
9. Cukovic D, Ehlting J, VanZiffle JA, Douglas CJ (2001) Structure and evolution of 4-coumarate: coenzyme A ligase (4CL) gene families. Biol Chem 382: 645-654.
10. De Eknamkul W, Ellis BE (1987) Tyrosine aminotransferase: the entry-point enzyme of the tyrosine-derived pathway in rosmarinic acid biosynthesis. Phytochemistry 26: 1941-1946.
11. Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7: 1085-1097.
12. 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.
13. Ehlting J, Büttner D, Wang Q, Douglas CJ, Somssich IE, Kombrink E (1999) Three 4-coumarate: coenzyme A ligases in Arabidopsis thaliana represent two evolutionary divergent classes in angiosperms. Plant J 19: 9-20.
14. Ehlting J, Shin JJK, Douglas CJ (2001) Identification of 4-coumarate: coenzyme A ligase (4CL) substrate recognition domains. Plant J 27: 455-465.
15. Ellis BE, Towers GHN (1970) Biogenesis of rosmarinic acid in Mentha. Biochem J 118: 291-297.
16. 32P-based hybridizations. Anal Biochem 210: 235-244.
17. Fecka I, Turek S (2007) Determination of water-soluble polyphenolic compounds in commercial herbal teas from Lamiaceae: peppermint, Melissa, and sage. J Agric Food Chem 55: 10908-10917.
18. Gang DR, Simon J, Lewinsohn E, Pichersky E (2002) Peltate glandular trichomes of Ocimum basilicum L. (Sweet Basil) contain high levels of enzymes involved in the biosynthesis of phenylpropenes. J Herbs Spices Med Plants 9: 189-195.
19. Hahlbrock K, Scheel D (1989) Physiology and molecular biology of phenylpropanoid metabolism. Annu Rev Plant Physiol Plant Mol Biol 40: 347-369.
20. Häusler E, Petersen M, Alfermann AW (1991) Hydroxyphenylpyruvate reductase from cell suspension cultures of Coleus blumei Benth. Z Naturforsch 46c: 371-376.
21. Heitz A, Carnat A, Fraisse D, Carnat AP, Lamaison JL (2000) Luteolin 3′-glucuronide, the major flavonoid from Melissa officinalis subsp. officinalis. Fitotherapia 71: 201-202.
22. Huang B, Yi B, Duan Y, Sun L, Yu X, Guo J, Chen W (2008) Characterization and expression profiling of tyrosine aminotransferase gene from Salvia miltiorrhiza (Dan-shen) in rosmarinic acid biosynthesis pathway. Mol Biol Rep 35: 601-612.
23. Joos HJ, Hahlbrock K (1992) Phenylalanine ammonia-lyase in potato (Solanum tuberosum L.). Eur J Biochem 204: 621-629.
24. 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.
25. Kumar A, Ellis BE (2001) The phenylalanine ammonia-lyase gene family in raspberry: structure, expression, and evolution. Plant Physiol 127: 230-239.
26. Kumar A, Ellis BE (2003) 4-Coumarate: CoA ligase gene family in Rubus idaeus: cDNA structures, evolution, and expression. Plant Mol Biol 31: 327-340.
27. Lee SW, Robb J, Nazar RN (1992) Truncated phenylalanine ammonia-lyase expression in tomato (Lycopersicon esculentum). J Biol Chem 267: 11824-11830.
28. Lindermayr C, Möllers B, Fliegmann J, Uhlmann A, Lottspeich F, Meimberg H, Ebel J (2002) Divergent members of a soybean (Glycine max L.) 4-coumarate: coenzyme A ligase gene family. Eur J Biochem 269: 1304-1315.
29. Lozoya E, Hoffmann H, Douglas C, Schulz W, Scheel D, Hahlbrock K (1988) Primary structures and catalytic properties of isoenzymes encoded by the two 4-coumarate: CoA ligase genes in parsley. Eur J Biochem 176: 661-667.
30. Mahesh V, Rakotomalala JJ, Gal LL, Vigne H, de Kochko A, Hamon S, Noirot M, Campa C (2006) Isolation and genetic mapping of a Coffea canephora phenylalanine ammonia-lyase gene (CcPAL1) and its involvement in the accumulation of caffeoyl quinic acids. Plant Cell Rep 25: 986-992.
31. Matsumoto S, Takeuchi A, Hayatsu M, Kondo S (1994) Molecular cloning of phenylalanine ammonia-lyase cDNA and classification of varieties and cultivars of tea plants (Camellia sinensis) using the tea PAL cDNA probe. Theor Appl Genet 89: 671-675.
32. 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.
33. 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 23: 1433-1440.
34. Mulkens A, Kapetanidis I (1987) Flavonoids from leaves of Melissa officinalis L. (Lamiaceae). Pharm Acta Helv 62: 19-22.
35. Murin A (1997) Karyotaxonomy of some medicinal and aromatic plants. Thaiszia 7: 75-88.
36. Parnham MJ, Kesselring K (1985) Rosmarinic acid. Drugs Future 10: 756-757.
37. Patora J, Klimek B (2002) Flavonoids from lemon balm (Melissa officinalis L., Lamiaceae). Acta Pol Pharm 59: 139-143.
38. Petersen M (1991) Characterization of rosmarinic acid synthase from cell cultures of Coleus blumei. Phytochemistry 30: 2877-2881.
39. Petersen M (1994) Coleus spp.: in vitro culture and the production of forskolin and rosmarinic acid. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, medicinal and aromatic plants VI. Springer, Berlin, pp 69-92.
40. Petersen M (1997) Cytochrome P-450-dependent hydroxylation in the biosynthesis of rosmarinic acid in Coleus. Phytochemistry 45: 1165-1172.
41. 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.
42. Petersen M, Simmonds MSJ (2003) Molecules of interest: rosmarinic acid. Phytochemistry 62: 121-125.
43. 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.
44. 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.
45. Ritter H, Schulz GE (2004) Structural basis for the entrance into the phenylpropanoid metabolism catalyzed by phenylalanine ammonia-lyase. Plant Cell 16: 3426-3436.
46. Rogers SO, Bendich AJ (1985) Extraction of DNA from milligram amounts of fresh, herbarium and mummified tissues. Plant Mol Biol 5: 69-76.
47. Scarpati ML, Oriente G (1958) Isolamento e costituzione dell'acido rosmarinico (dal rosmarinus off.). Ric Sci 28: 2329-2333.
48. Schneider K, Hövel K, Witzel K, Hamberger B, Schomburg D, Kombrink E, Stuible HP (2003) The substrate specificity-determining amino acid code of 4-coumarate: CoA ligase. Proc Natl Acad Sci USA 100: 8601-8606.
49. 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.
50. Strid A (1983) IOPB chromosome number reports LXXVIII. Taxon 32: 138-140.
51. Stuible HP, Büttner D, Ehlting J, Hahlbrock K, Kombrink E (2000) Mutational analysis of 4-coumarate: CoA ligase identifies functionally important amino acids and verifies its close relationship to other adenylate-forming enzymes. FEBS Lett 467: 117-122.
52. Szabo E, Thelen A, Petersen M (1999) Fungal elicitor preparations and methyl jasmonate enhance rosmarinic acid accumulation in in vitro-cultures of Coleus blumei. Plant Cell Rep 18: 485-489.
53. Tamura K, Dudley J, Nei M, Kumar S (2007) MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4. 0. Mol Biol Evol 24: 1596-1599.
54. Wanner LA, Li G, Ware D, Somssich IE, Davis KR (1995) The phenylalanine ammonia-lyase gene family in Arabidopsis thaliana. Plant Mol Biol 27: 327-338.
55. Wölbling RH, Leonhardt K (1994) Local therapy of herpes simplex with dried extracts from Melissa officinalis. Phytomedicine 1: 25-31.
56. Xu F, Cai R, Cheng S, Du H, Wang Y, Cheng S (2008) Molecular cloning, characterization and expression of phenylalanine ammonia-lyase gene from Ginkgo biloba. Afr J Biotechnol 7: 721-729.
57. 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.
58. 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.
59. Zhang XH, Chiang VL (1997) Molecular cloning of 4-coumarate: coenzyme A ligase in loblolly pine and the roles of this enzyme in the biosynthesis of lignin in compression wood. Plant Physiol 113: 65-74.
60. 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.