Metabolomic alterations in elicitor treated Silybum marianum suspension cultures monitored by nuclear magnetic resonance spectroscopy

Journal of Biotechnology

Volumn 130, Issue 2, 2007, Pages 133-142

  Sánchez Sampedro, Angeles ^a   Kim, Hye Kyong ^b   Choi, Young Hae ^b   Verpoorte, Robert ^b   Corchete, Purificación ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b LEIDEN UNIVERSITY   (Netherlands)

Author keywords

Flavonolignans; Metabolic difference; Methyl jasmonate; Nuclear magnetic resonance spectroscopy; Silybum marianum; Yeast elicitor

Indexed keywords

AMINO ACIDS; CARBOHYDRATES; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUSPENSIONS (FLUIDS); YEAST;

FLAVONOLIGNANS; METABOLIC DIFFERENCES; METHYL JASMONATE; SILYBUM MARIANUM; YEAST ELICITOR;

CELL CULTURE;

JASMONIC ACID METHYL ESTER; SILYMARIN;

AMINO ACID METABOLISM; ARTICLE; CARBOHYDRATE METABOLISM; CELL CULTURE; DRUG SYNTHESIS; METABOLOMICS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT CELL; PRIORITY JOURNAL; PROTEIN SYNTHESIS; QUANTITATIVE ANALYSIS; SILYBUM MARIANUM; YEAST;

ACETIC ACIDS; ALANINE; ALPHA-LINOLENIC ACID; AMINO ACIDS; CARBOHYDRATE METABOLISM; CELL CULTURE TECHNIQUES; CELLS, CULTURED; CHOLINE; CYCLOHEXIMIDE; CYCLOPENTANES; GLUCOSE; GLUTAMIC ACID; MILK THISTLE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT GROWTH REGULATORS; PROTEIN SYNTHESIS INHIBITORS; SILYMARIN; SUCROSE; YEASTS;

SILYBUM MARIANUM;

EID: 34249101291     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2007.03.007     Document Type: Article

References (45)

1. Agarwal C., Singh R.P., Dhanalakshmi S., Tyagi A.K., Tecklenburg M., Sclafani R.A., and Agarwal R. Silibinin upregulates the expression of cyclin-dependent kinase inhibitors and causes cell cycle arrest and apoptosis in human colon carcinoma HT-29 cells. Oncogene 22 (2003) 8271-8282
2. Becker H., and Schrall R. Callus und suspensionskulturen von Silybum marianum. Planta Med. 31 (1977) 185-192
3. Boerjan W., Ralph J., and Baucher M. Lignin biosynthesis. Annu. Rev. Plant Biol. 54 (2003) 519-546
4. Bostock R.M., Laine R., and Kuc A. Factors affecting the elicitation of sesquiterpenoid phytoalexin accumulation by eicosapentaenoic and arachidonic acid in potato. Plant Physiol. 70 (1982) 1417-1424
5. Broeckling C.D., Huhman D.V., Farag M.A., Smith J.T., May G.D., Mendes P., Dixon R.A., and Sumner L.W. Metabolic profiling of Medicago truncatula cell cultures reveals the effects of biotic and abiotic elicitors on metabolism. J. Exp. Bot. 56 (2004) 323-336
6. Cacho M., Morán M., Corchete P., and Fernández-Tárrago J. Influence of medium composition on the accumulation of flavonolignans in cultured cells of Silybum marianum (L.) Gaertn. Plant Sci. 144 (1999) 63-68
7. 1H NMR and multivariate analysis technique. Phytochemistry 65 (2004) 857-864
8. 1H NMR spectroscopy and multivariate data analysis. Plant Physiol. 135 (2004) 2398-2410
9. Choi Y.H., Kim H.K., Linthorst H.J.M., Hollander J.G., Lefeber A.W.M., Erkelens C., Nuzillard J.-M., and Verpoorte R. NMR metabolomics to revisit the tobacco mosaic virus infection in Nicotiana tabacum leaves. J. Nat. Prod. 69 (2006) 742-748
10. Conrath U., Domard A., and Kauss H. Chitosan-elicited synthesis of callose and of coumarin derivatives in parsley cell suspension cultures. Plant Cell Rep. 8 (1989) 152-155
11. Dangl J.L., and Jones J.D.G. Plant pathogens and integrated defence responses to infection. Nature 411 (2001) 826-833
12. Dewick P.M. Medicinal natural products. A Biosynthetic Approach (2002), John Wiley & Sons, Ltd, Chichester, UK
13. Ferreiro P., Pais M.S.S., and Cabral J.M.S. Production of silybin-like compounds in cell suspension cultures of Silybum marianum. Planta Med. 57 (1991) 2-3
14. Flora K., Hahn M., and Benner K. Milk thistle (Silybum marianum) for the therapy of liver disease. Am. J. Gastroenterol. 93 (1998) 139-143
15. Gorham, J., 1995. Betaines in higher plants-biosynthesis and role in stress metabolism. In: Wallsgrove, R.M. (Ed.), Amino acids and Their Derivatives in Higher Plants. Society for Experimental Biology Seminar Series, vol. 56, Cambridge University Press, Cambridge, pp. 173-203.
16. Griffin J.L., and Shockcor J.P. Metabolic profiles of cancer cells. Nat. Rev. Cancer 4 (2004) 551-561
17. Hanson A.D., Rivoal J., Burnet M., and Rathinasabapathi B. Biosynthesis of quaternary ammonium and tertiary sulphonium compounds in response to water deficit. In: Smirnoff N. (Ed). Environment and Plant Metabolism: Flexibility and Acclimation (1995), Bios Scientific, Oxford 189-198
18. Hendrawati O., Yao Q., Kim H.K., Linthorst H.J.M., Erkelens C., Lefeber A.W.M., Choi Y.H., and Verpoorte R. Metabolic differentiation of Arabidopsis treated with methyl jasmonate using nuclear magnetic resonance spectroscopy. Plant Sci. 170 (2006) 1118-1124
19. Henkes S., Sonnewald U., Badur R., Flachmann R., and Stitt M. A small decrease of plastid transketolase activity in antisense tobacco transformants has dramatic effects on photosynthesis and phenylpropanoid metabolism. Plant Cell 13 (2001) 535-551
20. Khatib A., Wilson E.G., Kim H.K., Lefeber A.W.M., Erkelens C., Choi Y.H., and Verpoorte R. Application of two dimensional J-resolved nuclear magnetic resonance spectrum to differentiation of beer. Anal. Chim. Acta 559 (2006) 264-270
21. Kim N.C., Graf T.N., Sparacino C.M., Wani M.C., and Wall M.E. Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum). Org. Biomol. Chem. 1 (2003) 1684-1689
22. Kraemer K.H., Schenkel E.P., and Verpoorte R. Glucosylation of ethanol in Ilex paraguariensis cell suspension cultures. Plant Cell Rep. 18 (1999) 509-513
23. Krishnan P., Kruger N.J., and Ratcliffe R.G. Metabolite fingerprinting and profiling in plants using NMR. J. Exp. Bot. 56 (2005) 255-265
24. Lee D.Y.W., and Liu Y.Z.J. Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle). Nat. Prod. 66 (2003) 1171-1174
25. Liang Y.-S., Kim H.K., Lefeber A.W.M., Erkelens C., Choi Y.H., and Verpoorte R. Identification of phenylpropanoids in Brassica rapa leaves treated with methyl jasmonate using two-dimensional nuclear magnetic resonance spectroscopy. J. Chromatogr. A. 1112 (2006) 148-155
26. Morazzoni P., and Bombardelli E. Silybum marianum (Carduus marianum). Fitoterapia 66 (1995) 3-42
27. Mou Z., Wang X., Fu Z., Dai Y., Han C., Ouyang J., Bao F., Hu Y., and Li J. Silencing of phosphoethanolamine N-methyltransferase results in temperature-sensitive male sterility and salt hipersensitiviy in Arabidopsis. Plant Cell 14 (2002) 2031-2043
28. Murashige T., and Skoog F. A revised medium for rapid growth and bioassays with tobacco tissue cultures. Physiol. Plant. 15 (1962) 473-497
29. Norman E., De Smet K.A.L., Stoker N.G., Ratledge C., Wheeler P.R., and Dale J.W. Lipid synthesis in Mycobacteria: characterization of the biotin carboxyl carrier protein genes from Mycobacterium leprae and M. tuberculosis. J. Bacteriol. 176 (1994) 2525-2531
30. Rhodes D., and Hanson A.D. Quaternary ammonium and tertiary sulfonium compounds in higher plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 44 (1993) 357-384
31. Rontein D., Nishida I., Tashiro G., Yoshioka K., Wu W.I., Voelker D.R., Basset G., and Hanson A.D. Plants synthesize ethanolamine by direct decarboxylation of serine using a pyridoxal phosphate enzyme. J. Biol. Chem. 276 (2001) 35523-35529
32. Sánchez-Sampedro M.A., Fernández-Tárrago J., and Corchete P. Yeast extract and methyl jasmonate-induced silymarin production in cell cultures of Silybum marianum (L.) Gaernt. J. Biotech. 119 (2005) 60-69
33. Scheel D. Resistance response physiology and signal transduction. Curr. Opin. Plant Biol. 1 (1998) 305-310
34. Schumacher H.M., Gundlach H., Fiedler F., and Zenk M.H. Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia cell cultures. Plant Cell Rep. 6 (1987) 410-413
35. Seigler D.S. Plant Secondary Metabolism (1998), Kluwer Academic Publishers, Boston, Dordrecht, London
36. Sembdner G., and Parthier B. The biochemistry and the physiological and molecular actions of jasmonates. Ann. Rev. Plant Physiol. Plant Mol. Biol. 44 (1993) 569-589
37. Sudha G., and Ravishankar G.A. Involvement and interaction of various signaling compounds on the plant metabolic events during defense response, resistance to stress factors, formation of secondary metabolites and their molecular aspects. Plant Cell Tissue Organ Cult. 71 (2002) 181-212
38. Sumner L.W., Mendes P., and Dixon R.A. Plant metabolomics: large-scale phytochemistry in the functional genomics era. Phytochemistry 62 (2003) 817-836
39. Tamari G., Borochov A., Atzorn R., and Weiss D. Methyl jasmonate induces pigmentation and flavonoid gene expression in petunia corollas: a possible role in wound response. Physiol. Plant. 94 (1995) 45-50
40. Tyler R.T., Eilert U., Rijnders C.O.M., Roewe I.A., McNabb C.K., and Kurz W.G.W. Studies on benzophenanthrid in alkaloid production in elicited cell cultures of Papaver somniferum L. In: Kurz W.G.W. (Ed). Primary and Secondary Metabolism of Plant Cell Cultures (1989), Springer-Verlag, Berlin 200-207
41. Valenzuela, A., Guerra R., Videla, L.A., 1986. Antioxidant properties of the flavonoids silybin and silibinin, an active constituent of milk thistle: comparison with silymarin. Cancer Lett. 147, 77-84. (+)-cyanidanol-3: comparison with butylated hydroxytoluene. Planta Med. 52, 438-440.
42. Xiaolin Z., Grasso A.W., Hsing-Jien K., and Agarwal R. A flavonoid antioxidant, silymarin, inhibits activation of erbB1 signaling and induces cyclin-dependent kinase inhibitors, G1 arrest, and anticarcinogenic effects in human prostate carcinoma DU145 cells. Cancer Res. 59 (1999) 622-632
43. Yanaida Y., Kohno Y., Yoshida K., Hirose Y., Yamada Y., Mori H., and Tanaka T. Dietary silymarin suppresses 4-nitroquinoline 1-oxide-induced tongue carcinogenesis in male F344 rats. Carcinogenesis 23 (2002) 787-794
44. Yang S.Y., Kim H.K., Lefeber A.W.M., Erkelens C., Angelova N., Choi Y.H., and Verpoorte R. Application of two dimensional nuclear magnetic resonance spectroscopy to quality control of ginseng commercial products. Planta Med. 72 (2006) 364-369
45. Zhao B., Wolf D.M., and Agrawal R. Inhibition of human carcinoma cell growth and DNA synthesis by silibinin, an active constituent of milk thistle: comparison with silymarin. Cancer Lett. 147 (1999) 77-84