Phenolic compounds in Catharanthus roseus

Phytochemistry Reviews

Volumn 6, Issue 2-3, 2007, Pages 243-258

  Mustafa, Natali Rianika ^a   Verpoorte, Robert ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Catharanthus roseus; Phenolic compounds

Indexed keywords

4 AMINOBENZOATE SYNTHASE; 4 HYDROXBENZOIC ACID SYNTHASE; ANTHRANILATE SYNTHASE; BENZOIC ACID; CHLOROGENIC ACID; CHORISMATE MUTASE; CHORISMATE PYRUVATE LYASE; CINNAMIC ACID; ENZYME; FERULIC ACID; GALLIC ACID; GLUCOVANILLIC ACID; GLUCOVANILLIN; HIRSUTIDIN; HIRSUTIDIN 3 O (6 O 4 COUMAROYL); HIRSUTIDIN 3 O GLUCOSIDE; HIRSUTINE; HYDROXYTYROSOL; INDOLE ALKALOID; ISOCHORISMATE SYNTHASE; KAEMPFEROL; MALVIDIN CHLORIDE; PHENOL DERIVATIVE; PROPANE; QUERCETIN; QUERCETIN DERIVATIVE; TRISACCHARIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANILLIC ACID; VANILLYL ALCOHOL;

ABIOTIC STRESS; BIOSYNTHESIS; CELL DENSITY; CELL SUSPENSION; METHYLATION; MOLECULAR INTERACTION; NONHUMAN; PHYTOCHEMISTRY; PLANT CELL; PRIORITY JOURNAL; REGULATORY MECHANISM; REVIEW;

CATHARANTHUS ROSEUS;

EID: 34249951277     PISSN: 15687767     EISSN: 1572980X     Source Type: Journal    
DOI: 10.1007/s11101-006-9039-8     Document Type: Review

References (82)

1. Aerts RJ, Alarco AM, De Luca V (1992) Auxins induce tryptophan decarboxylase activity in radicles of Catharanthus roseus seedlings. Plant Physiol 100:1014-1019
2. Boudet AM, Lapierre C, Grima-Pettenati J (1995) Biochemistry and molecular biology of lignification. New Phytol 129:203-236
3. Bruneton J (1999) Pharmacognosy: phytochemistry medicinal plants, 2 edn. Intercept Ltd., Hampshire, UK, pp 227-231
4. Brun G, Dijoux MG, David B, Mariotte AM (1999) A new flavonol glycoside from Catharanthus roseus. Phytochemistry 50:167-169
5. Budi Muljono RA (2001) The isochorismate pathway as a route to 2,3-dihydroxybenzoic acid in Catharanthus roseus cell cultures. Leiden University, The Netherlands, pp 73-76
6. Budi Muljono RA, Looman AMG, Verpoorte R, Scheffer JJC (1998) Assay of salicylic acid and related compounds in plant cell cultures by capillary GC. Phytochem Anal 9:35-38
7. Budi Muljono RA, Scheffer JJC, Verpoorte R (2002) Isochorismate is an intermediate in 2,3-dihydroxybenzoic acid biosynthesis in Catharanthus roseus cell cultures. Plant Physiol Biochem 40:231-234
8. Cacace S, Schroeder G, Wehinger E, Strack D, Schmidt J, Schroeder J (2003) A flavonol O-methyltransferase from Catharanthus roseus performing two sequential methylations. Phytochemistry 62:127-137
9. Carew DP, Krueger RJ (1976) Anthocyanidins of Catharanthus roseus callus cultures. Phytochemistry 15:442
10. Cary AJ, Liu W, Howell SH (1995) Cytokinin action is coupled to ethylene in its effects on the inhibition of root and hypocotyl elongation in Arabidopsis thaliana seedlings. Plant Physiol 107:1075-1082
11. 1H-NMR spectroscopy and multivariate data analysis. Plant Physiol 135:2398-2410
12. Chong J, Pierrel MA, Atanassova R, Werck-Reichhart D, Fritig B, Saindrenan P (2001) Free and conjugated benzoic acid in tobacco plants and cell cultures. Induced accumulation upon elicitation of defense responses and role as salicylic acid precursors. Plant Physiol 125:318-328
13. Dean JV, Mills JD (2004) Uptake of salicylic acid 2-O-β-D-glucose into soybean tonoplast vesicles by an ATP-binding cassette transporter-type mechanism. Physiol Plant 120:603-612
14. Dempsey DA, Shah J, Klessig DF (1999) Salicylic acid and disease resistance in plants. Crit Rev Plant Sci 18:547-575
15. Dewick PM (2002) Medicinal natural products: a biosynthetic approach, 2nd edn. John Wiley & Sons Ltd, England, pp 149-151
16. Dixon RA (2001) Natural products and disease resistance. Nature 411:843-847
17. El-Basyouni SZ, Chen D, Ibrahim RK, Neish AC, Towers GHN (1964) The biosynthesis of hydroxybenzoic acids in higher plants. Phytochemistry 3:485-492
18. El-Sayed M, Verpoorte R (2002) Effect of phytohormones on growth and alkaloid accumulation by a Catharanthus roseus cell suspension cultures fed with alkaloid precursors tryptamine and loganin. Plant Cell Tiss Org Cult 68:265-270
19. El-Sayed M, Verpoorte R (2004) Growth, metabolic profiling and enzymes activities of Catharanthus roseus seedlings treated with plant growth regulators. Plant Growth Regul 44:53-58
20. Filippini R, Caniato R, Piovan A, Cappelletti EM (2003) Production of anthocyanins by Catharanthus roseus. Fitoterapia 74:62-67
21. Forsyth WGC, Simmonds NW (1957) Anthocyanidins of Lochnera rosea. Nature 180:247
22. Friedman H, Meir S, Halevy AH, Philosoph-Hadas S (2003) Inhibition of the gravitropic bending response of flowering shoots by salicylic acid. Plant Sci 165:905-911
23. Glazebrook J, Chen W, Estes B, Chang HS, Nawrath C, Metraux JP, Zhu T, Katagiri F (2003) Topology of the network integrating salicylate and jasmonate signal transduction derived from global expression phenotyping. Plant J 34:217-228
24. Godoy-Hernandez GC, Loyola-Vargas VM (1991) Effect of fungal homogenate, enzyme inhibitors and osmotic stress on alkaloid content of Catharanthus roseus. Plant Cell Rep 10:537-540
25. Godoy-Hernandez GC, Vazquez-Flota FA, Loyola-Vargas VM (2000) The exposure to trans-cinnamic acid of osmotically stressed Catharanthus roseus cells cultured in a 14-L bioreactor increases alkaloid accumulation. Biotechnol Let 22:921-925
26. Hall RD, Yeoman MM (1986) Factors determining anthocyanin yield in cell cultures of Catharanthus roseus (L.) G.Don. New Phytol 103:33-43
27. Harborne JB, Williams CA (2000) Advances in flavonoid research since 1992. Phytochemistry 55:481-504
28. Herrmann KM, Weaver LM (1999) The shikimate pathway. Annu Rev Plant Physiol Plant Mol Biol 50:473-503
29. 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 278:95-103
30. 450 reductase in Escherichia coli. FEBS Lett 374:345-350
31. Ibrahim RK, Towers GHN (1959) Conversion of salicylic acid to gentisic acid and o-pyrocathechuic acid, all labeled with Carbon-14, in plants. Nature 184:1803
32. Knobloch KH, Bast G, Berlin J (1982) Medium-and light-induced formation of serpentine and anthocyanins in cell suspension cultures of Catharanthus roseus. Phytochemistry 21:591-594
33. Knobloch KH, Berlin J (1981) Effects of media constituents on the formation of secondary products in cell suspension cultures of Catharanthus roseus. In: Moo-Young M, Robinson CW, Vezina C (eds) Adv. Biotechnol. [Proceedings of International Ferment. Symp.], 6th, Pergamon, Toronto
34. Kunkel BN, Brooks DM (2002) Cross talk between signaling pathways in pathogen defense. Curr Opin Plant Biol 5:325-331
35. Leduc C, Birgel I, Muller R, Leistner E (1997) Isochorismate hydroxymutase from cell suspension culture of Galium mollugo. Planta 202:206-210
36. Lee HI, Raskin I (1998) Glucosylation of salicylic acid in Nicotiana tabacum cv. Xanthi-nc. Phytopathology 88:692-697
37. Leon J, Shulaev V, Yalpani N, Lawton MA, Raskin I (1995) Benzoic acid 2-hydroxylase, a soluble oxygenase from tobacco, catalyzes salicylic acid biosynthesis. Proc Natl Acad Sci USA 92:10413-10417
38. Leslie CA, Romani RJ (1986) Salicylic acid: a new inhibitor of ethylene biosynthesis. Plant Cell Rep 5:144-146
39. Loescher R, Heide L (1994) Biosynthesis of p-hydroxybenzoate from p-coumarate and p-coumaroyl-coenzyme A in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 106:271-279
40. Matern U, Grimmig B, Kneusel RE (1995) Plant cell wall reinforcement in the disease-resistance response: molecular composition and regulation. Can J Bot 73:S511-S517
41. Mitchell HJ, Hall SA, Stratford R, Hall JL, Barber MS (1999) Differential induction of cinnamyl alcohol dehydrogenase during defensive lignification in wheat (Triticum aestivum L.): characterization of the major inducible form. Planta 208:31-37
42. Moreno PRH (1995) Influence of stress factors on the secondary metabolism in suspension cultured Catharanthus roseus cells. Leiden University, The Netherlands, pp 64-65
43. Moreno PRH, Poulsen C, van der Heijden R, Verpoorte R (1996) Effects of elicitation on different metabolic pathways in Catharanthus roseus (L.) G. Don cell suspension cultures. Enzyme Microb Technol 18:99-107
44. Moreno PRH, van der Heijden R, Verpoorte R (1994a) Elicitor-mediated induction of isochorismate synthase and accumulation of 2,3-dihydroxybenzoic acid in Catharanthus roseus cell suspension and shoot cultures. Plant Cell Rep 14:188-191
45. Moreno PRH, van der Heijden R, Verpoorte R (1994b) Induction of the secondary metabolism in Catharanthus roseus cell suspension cultures in response to UV irradiation and the addition of a benzoic acid derivative. Heterocycles 39:457-465
46. Mustafa NR, Verpoorte R (2005) Chorismate derived C6C1 compounds in plants. Planta 222:1-5
47. Nishibe S, Takenaka T, Fujikawa T, Yasukawa K, Takido M, Morimitsu Y, Hirota A, Kawamura T, Noro Y (1996) Bioactive phenolic compounds from Catharanthus roseus and Vinca minor. Natural Medicines (Tokyo) 50:378-383
48. Ohlsson AB, Berglund T, Komlos P, Rydstrom J (1995) Plant defense metabolism is increased by the free radical-generating compound AAPH. Free Rad Biol Med 19:319-327
49. Ossipov V, Salminen JP, Ossipova S, Haukioja E, Pihlaja K (2003) Gallic acid and hydrolysable tannins are formed in birch leaves from an intermediate compound of the shikimate pathway. Biochem System Ecol 31:3-16
50. Papon N, Bremer J, Vansiri A, Andreu F, Rideau M, Creche J (2005) Cytokinin and ethylene control indole alkaloid production at the level of the MEP/Terpenoid pathway in Catharanthus roseus suspension cells. Planta Med 71:572-574
51. Pasquali G, Goddijn OJM, De Waal A, Verpoorte R, Schilperoort RA, Hoge JHC, Memelink J (1992) Coordinated regulation of two indole alkaloid biosynthetic genes from Catharanthus roseus by auxin and elicitors. Plant Mol Biol 18:1121-1131
52. Pieterse CMJ, Ton J, Van Loon LC (2001) Cross-talk between plant defense signaling pathways: boost or burden? Ag Biotech Net 3:1-8
53. Poulsen C, van der Heijden R, Verpoorte R (1991) Assay of isochorismate synthase from plant cell cultures by high performance liquid chromatography. Phytochemistry 30:2873-2878
54. Proestos C, Chorianopoulos N, Nychas G-JE, Komaitis M (2005) RP-HPLC analysis of phenolic compounds of plant extracts. Investigation of their antioxydant capacity and antimicrobial activity. J Agricult Food Chem 53:1190-1195
55. Raskin I (1992) Role of salicylic acid in plants. Annu Rev Plant Physiol Plant Mol Biol 43:439-463
56. Ryals JA, Neuenschwander UH, Willits MG, Molina A, Steiner HY, Hunt MD (1996) Systemic acquired resistance. Plant Cell 8:1809-1819
57. 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
58. Schroeder G, Wehinger E, Lukacin R, Wellmann F, Seefelder W, Schwab W, Schroeder J (2004) Flavonoid methylation: a novel 4′-O-methyltransferase from Catharanthus roseus, and evidence that partially methylated flavanones are substrates of four different flavonoid dioxygenases. Phytochemistry 65:1085-1094
59. Seitz HU, Eilert U, De Luca V, Kurz WGW (1989) Elicitor-mediated induction of phenylalanine ammonia-lyase and tryptophan decarboxylase: accumulation of phenols and indole alkaloids in cell suspension cultures of Catharanthus roseus. Plant Cell Tiss Org Cult 18:71-78
60. Shah J (2003) The salicylic acid loop in plant defense. Curr Opin Plant Biol 6:365-371
61. Shimoda K, Kubota N, Sano T, Hirakawa H, Hirata T (2004) A novel hydroxylase from Catharanthus roseus participating in the hydroxylation of 2-hydroxybenzoic acid. J Biosci Bioeng 98:67-70
62. Shimoda K, Yamane S-y, Hirakawa H, Ohta S, Hirata T (2002) Biotransformation of phenolic compounds by the cultured cells of Catharanthus roseus. J Mol Catal B Enzym 16:275-281
63. Sommer J, Schroeder C, Stoeckigt J (1997) In vivo formation of vanillin glucoside. Plant Cell Tiss Org Cult 50:119-123
64. Stalman M, Koskamp AM, Luderer R, Vernooy JHJ, Wind JC, Wullems GJ, Croes AF (2003) Regulation of anthraquinone biosynthesis in cell cultures of Morinda citrifolia. J Plant Physiol 160:607-614
65. Sudheer BK, Seeta Ram Rao S (1998) Effect of phenolic compounds on growth and total alkaloid content of Catharanthus roseus (L.) G.Don. Indian J Plant Physiol 3:300-302
66. Talou JR, Verberne MC, Budi Muljono RA, van Tegelen LJP, Bernal BG, Lnthorst HJM, Wullems GJ, Bol JF, Verpoorte R (2001) Isochorismate synthase transgenic expression in Catharanthus roseus cell suspensions. Plant Physiol Biochem 39:595-602
67. Torsell KBG (1997) Natural product chemistry, a mechanistic, biosynthetic and ecological approach, 2nd edn. Apotekarsocieteten-Swedish Pharmaceutical Society, Swedish Pharmaceutical Press, Stockholm, pp 117-173
68. Van der Fits L, Memelink J (2000) ORCA3, a jasmonate-responsive transcriptional regulator of plant primary and secondary metabolism. Science 289:295-297
69. Van Tegelen LJP, Moreno PRH, Croes AF, Verpoorte R, Wullems GJ (1999) Purification and cDNA cloning of isochorismate synthase from elicited cell cultures of Catharanthus roseus. Plant Physiol 119:705-712
70. Van Wees SCM, de Swart EAM, van Pelt JA, van Loon LC, Pieterse CMJ (2000) Enhancement of induced disease resistance by simultaneous activation of salicylate-and jasmonate-dependent defense pathways in Arabidopsis thaliana. PNAS 97:8711-8716
71. Verberne MC, Budi Muljono RA, Verpoorte R (1999) Salicylic acid biosynthesis. In: Libbenga K, Hall M, Hooykaas PJJ (eds) Biochemistry and molecular biology of plant hormones, vol 33. Elsevier, London, pp 295-312
72. Verberne MC, Verpoorte R, Bol JF, Mercado-Blanco J, Linthorst HJM (2000) Overproduction of salicylic acid in plants by bacterial transgenes enhances pathogen resistance. Nat Biotechnol 18:779-783
73. Verpoorte R, Contin A, Memelink J (2002) Biotechnology for the production of plant secondary metabolites. Phytochem Rev 1:13-25
74. 13C-labeled glucose. J Biol Chem 272:25474-25482
75. Wildermuth MC, Dewdney J, Wu G, Ausubel FM (2001) Isochorismate synthase is required to synthesize salicylic acid for plant defense. Nature 414:562-565
76. Wink M (2000) Biochemistry of plant secondary metabolism: annual plant reviews, vol 2. Sheffield Academic Press, Sheffield UK, pp 151-221
77. Woeste KE, Vogel JP, Kieber JJ (1999) Factors regulating ethylene biosynthesis in etiolated Arabidopsis thaliana seedlings. Physiol Plant 105:478-484
78. - from elicitor-induced oxidative burst is necessary for triggering phenylalanine ammonia-lyase activation and catharanthine synthesis in Catharanthus roseus cell cultures. Enzyme Microb Technol 36:280-284
79. Yahia A, Kevers C, Gaspar T, Chenieux JC, Rideau M, Creche J (1998) Cytokinins and ethylene stimulate indole alkaloids accumulation in cell suspension cultures of Catharanthus roseus by two distinct mechanisms. Plant Sci 133: 9-15
80. Yamane S-y, Shimoda K, Watanabe K, Hirata T (2002) Purification and characterization of gentisic acid glucosyltransferase from the cultured cells of Catharanthus roseus. J Mol Catal B: Enzym 17:59-63
81. Young IG, Batterham T, Gibson F (1969) The isolation, identification and properties of isochorismic acid an intermediate in the biosynthesis of 2,3-dihydroxybenzoic acid. Biochim Biophys Acta 177:389-400
82. Yuana, Dignum MJW, Verpoorte R (2002) Glucosylation of exogenous vanillin by plant cell cultures. Plant Cell Tiss Org Cult 69:177-182