Elicited Teucrium chamaedrys cell cultures produce high amounts of teucrioside, but not the hepatotoxic neo-clerodane diterpenoids

Phytochemistry

Volumn 81, Issue , 2012, Pages 50-59

  Antognoni, Fabiana ^a   Iannello, Carmelina ^a   Mandrone, Manuela ^a   Scognamiglio, Monica ^b   Fiorentino, Antonio ^b   Giovannini, Pier Paolo ^c   Poli, Ferruccio ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b SECOND UNIVERSITY OF NAPLES   (Italy)

^c UNIVERSITY OF FERRARA   (Italy)

Author keywords

Cell cultures; Elicitation; Lamiaceae; neo Clerodane diterpenoids; NMR analysis; Phenylethanoid glycosides; Teucrium chamaedrys

Indexed keywords

ACETIC ACID DERIVATIVE; CAFFEIC ACID DERIVATIVE; CHITOSAN; CLERODANE DERIVATIVE; CYCLOPENTANE DERIVATIVE; GLYCOSIDE; HYDROXYPROLINE; JASMONIC ACID METHYL ESTER; OXYLIPIN; PLANT EXTRACT; PROLINE; SCAVENGER; TEUCRIUM EXTRACT; TEUCROSIDE;

ARTICLE; CHEMISTRY; COMPARATIVE STUDY; CULTURE TECHNIQUE; DRUG EFFECT; FUSARIUM; GERMANDER; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; METABOLISM; METABOLOME; METABOLOMICS; METHODOLOGY; MYCELIUM; PLANT CELL; PLANT LEAF; TIME; TRICHODERMA;

ACETATES; CAFFEIC ACIDS; CELL CULTURE TECHNIQUES; CHITOSAN; CYCLOPENTANES; DITERPENES, CLERODANE; FREE RADICAL SCAVENGERS; FUSARIUM; GLYCOSIDES; HYDROXYPROLINE; METABOLOME; METABOLOMICS; MYCELIUM; OXYLIPINS; PLANT CELLS; PLANT EXTRACTS; PLANT LEAVES; PROLINE; TEUCRIUM; TIME FACTORS; TRICHODERMA;

GIBBERELLA FUJIKUROI; LAMIACEAE; MYCELIUM (GENUS); TEUCRIUM; TEUCRIUM CHAMAEDRYS; TRICHODERMA; VIRUSES;

EID: 84864757361     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.05.027     Document Type: Article

References (54)

1. B. Avula, R.B. Manyam, E. Bedir, and I.A. Khan Rapid separation and determination of four phenylpropanoid glycosides from Teucrium chamaedrys by capillary electrophoresis method Chromatographia 58 2003 751 755
2. M.S. Barber, V.S. McConnell, and B.S. DeCaux Antimicrobial intermediates of the general phenylpropanoid and lignin specific pathways Phytochemistry 54 2000 53 56
3. L.S. Bates, R.P. Waldren, and I.D. Teare Rapid determination of free proline in water stress studies Plant Soil 39 1973 205 207
4. E. Bedir, R. Manyam, and I.A. Khan Neo-clerodane diterpenoids and phenylethanoid glycosides from Teucrium chamaedrys L. Phytochemistry 63 2003 977 983
5. S. Blechert, W. Brodschelm, S. Holder, L. Kamerer, T.M. Tutchan, M.J. Mueller, Z. Xia, and M.H. Zenk The octadecanoic pathway: signal molecules for the regulation of secondary pathways Proc. Natl. Acad. Sci. USA 92 1995 4099 4105
6. F. Bourgaud, A. Gravot, S. Milesi, and E. Gontier Production of plant secondary metabolites: a historical perspective Plant Sci. 161 2001 839 851
7. H. Chen, and F. Chen Effect of yeast elicitor on the secondary metabolism of Ti-transformed Salvia miltiorrhiza cell suspension cultures Plant Cell Rep. 19 2000 710 717
8. R. Chiej Enyclopedia of Medicinal Plants 1984 MacDonald London
9. T.M. Chong, M.A. Abdullah, O.M. Lai, F.M. Nor'Aini, and N.H. Lajis Effective elicitation factors in Morinda elliptica cell suspension culture Process Biochem. 40 2005 3397 3405
10. R.A. Creelman, and J.E. Mullet Biosynthesis and action of jasmonates in plants Annu. Rev. Plant Physiol. Plant Mol. Biol. 48 1997 355 381
11. B. Dell, C.L. Elsegood, and E.L. Ghisalberti Production of verbascoside in callus tissue of Eremophila spp. Phytochemistry 28 1989 1871 1872
12. B.E. Ellis Production of hydroxyphenylethanol glycosides in suspension cultures of Syringa vulgaris Phytochemistry 22 1983 1941 1943
13. Eriksson, L., Johansson, E., Kettanah-Wold, N., Wold, S., 1999. Scaling. In: Introduction to multi and megavariate data analysis using projection methods (PCA & PLS). Umetrics, Umeå, Sweden, pp. 213-225.
14. M.E. Estrada-Zúñiga, F. Cruz-Sosa, M. Rodríguez- Monroy, J.R. Verde-Calvo, and E.J. Vernon-Carter Phenylpropanoid production in callus and cell suspension cultures of Buddleja cordata Kunth. Plant Cell Tiss. Organ Cult. 97 2009 39 47
15. M. Faudale, F. Viladomat, J. Bastida, F. Poli, and C. Codina Antioxidant activity and phenolic composition of wild, edible, and medicinal fennel from different Mediterranean countries J. Agric. Food Chem. 56 2008 1912 1920
16. A. Fiorentino, B. D'Abrosca, A. Ricci, S. Pacifico, S. Piccolella, and P. Monaco Structure determination of chamaedryosides A-C, three novel nor-neo-clerodane glucosides from Teucrium chamaedrys, by NMR spectroscopy Magn. Res. Chem. 47 2009 1007 1012
17. C. Funk, K. Gugler, and P. Brodelius Increased secondary product formation in plant cell suspension cultures after treatment with a yeast carbohydrate preparation (Elicitor) Phytochemistry 26 1987 401 405
18. S. Gadzovska, S. Maury, A. Delaunay, M. Spasenoski, C. Joseph, and D. Hagège Jasmonic acid elicitation of Hypericum perforatum L. cell suspensions and effects on the production of phenylpropanoids and naphtodianthrones Plant Cell Tiss. Organ Cult. 89 2007 1 13
19. G. Godoy-Hernandez, and F.A. Vazquez-Flota Growth measurements V.M. Loyola-Vargas, F.A. Vazquez-Flota, Plant Cell Culture Protocols second ed. 2006 Humana Press Inc. Totowa 51 58
20. L. Gori, P. Galluzzi, V. Mascherini, E. Gallo, F. Lapi, F. Menniti-Ippolito, R. Raschetti, A. Mugelli, A. Vannacci, and F. Firenzuoli Two contemporary cases of hepatitis associated with Teucrium chamaedrys L. decoction use. Case reports and review of literature Basic Clin. Pharmacol. Toxicol. 109 2011 521 526
21. G.A. Gross, M.F. Lahloub, C. Anklin, H.R. Schulten, and O. Sticher Teucrioside, a phenylpropanoid glycoside from Teucrium chamaedrys Phytochemistry 27 1988 1459 1463
22. D.M. Horvath, and N.H. Chua Identification of an immediate-early salicylic acid-inducible tobacco gene and characterization of induction by other compounds Plant Mol. Biol. 31 1996 1061 1072
23. A.K. Ibrahim, S. Khalifa, I. Khafagi, D. Youssef, I. Khan, and M. Mesbaha Stimulation of oleandrin production by combined Agrobacterium tumefaciens mediated transformation and fungal elicitation in Nerium oleander cell cultures Enz. Microb. Technol. 41 2007 331 336
24. L.G. Korkina, E.V. Mikhal'chik, M.V. Suprun, S. Pastore, and R. Dal Toso Molecular mechanisms underlying wound healing and anti-inflammatory properties of naturally occurring biotechnologically produced phenylpropanoid glycosides Cell Mol. Biol. 53 2007 78 83
25. S.A. Kouzi, R.J. McMurtry, and S.D. Nelson Hepatotoxicity of germander (Teucrium chamaedrys L.) and one of its constituent neoclerodane diterpene teucrin A in the mouse Chem. Res. Toxicol. 7 1994 850 856
26. D. Kwok, and K. Shetty Effects of proline and proline analogs on total phenolic and rosmarinic acid levels in shoot clones of thyme (Thymus vulgaris L.) J. Food Biochem. 22 1998 37 51
27. V. Lattanzio, A. Cardinali, C. Ruta, I. Morone Fortunato, V.M.T. Lattanzio, V. Linsalata, and N. Cicco Relationship of secondary metabolism to growth in oregano (Origanum vulgare L.) shoot cultures under nutritional stress Env. Exp. Bot. 65 2009 54 62
28. L.Z. Lin, J.M. Harnly, and R. Upton Comparison of the phenolic component profiles of skullcap (Scutellaria lateriflora) and germander (Teucrium canadense and T. chamaedrys), a potentially hepatotoxic adulterant Phytochem. Anal. 20 2009 298 306
29. M.B. Lu, H.L. Wong, and W.L. Teng Effects of elicitation on the production of saponin in cell culture of Panax ginseng Plant Cell Rep. 20 2001 674 677
30. D. Mares, E. Andreotti, M.E. Maldonado, P. Pedrini, C. Colalongo, and C. Romagnoli Three new species of Aspergillus from Amazonian forest soil (Ecuador) Appl. Microbiol. 57 2008 222 229
31. H. Mizukami, T. Ogawa, H. Ohashi, and B.E. Ellis Induction of rosmarinic acid biosynthesis in Lithospermum erythrorhizon cell suspension cultures by yeast extract Plant Cell Rep. 11 1992 480 483
32. T. Mulder-Krieger, R. Verpoorte, A. Baerheim Svendsen, and J.J.C. Scheffer Production of essential oils and flavours in plant cell and tissue cultures. A review Plant Cell Tiss. Organ Cult. 13 1988 85 154
33. T. Murashige, and F. Skoog A revised medium for rapid growth and bioassays with tobacco tissue cultures Physiol. Plant. 15 1962 473 497
34. A. Namdeo, S. Patil, and D.P. Fulzele Influence of fungal elicitors on production of Ajmalicine by cell cultures of Catharanthus roseus Biotechnol. Prog. 18 2002 159 162
35. L. Nezbedova, M. Hesse, J. Dušek, and C. Werner Chemical potential of Aphelandra sp. cell cultures Plant Cell Tiss. Organ Cult. 58 1999 133 140
36. S. Pacifico, B. D'Abrosca, M.T. Pascarella, M. Letizia, P. Uzzo, V. Piscopo, and A. Fiorentino Antioxidant efficacy of iridoid and phenylethanoid glycosides from the medicinal plant Teucrium chamaedris in cell-free systems Bioorg. Med. Chem. 17 2009 6173 6179
37. G. Pasqua, P. Avato, B. Monacelli, A.R. Santamaria, and M.P. Argentieri Metabolites in cell suspension cultures, calli, and in vitro regenerated organs of Hypericum perforatum cv. Topas. Plant Sci. 165 2003 977 982
38. S. Rajabalian Methanolic extract of Teucrium polium L. potentiates the cytotoxic and apoptotic effects of anticancer drugs of vincristine, vinblastine and doxorubicin against a panel of cancerous cell lines Exp. Oncol. 30 2008 133 138
39. S. Ramachandra Rao, and G.A. Ravishankar Plant cell cultures: chemical factories of secondary metabolites Biotechnol. Adv. 20 2002 101 153
40. K. Shetty Role of proline-linked pentose phosphate pathway in biosynthesis of plant phenolics for functional food and environmental applications: a review Process Biochem. 39 2004 789 803
41. Z. Skrzypek, and H. Wysokinska Accumulation of phenylethanoids in suspension cultures of Penstemon serrulatus Menz. Biotechnol. Lett. 21 1999 691 693
42. M.S. Stankovic, M.G. Curcic, J.B. Zizic, M.D. Topuzovic, S.R. Solujic, and S.D. Markovic Teucrium plant species as natural sources of novel anticancer compounds: antiproliferative, proapoptotic and antioxidant properties Int. J. Mol. Sci. 12 2011 4190 4205
43. M.S. Stankovic, M. Topuzovic, S. Solujic, and V. Mihailovic Antioxidant activity and concentration of phenols and flavonoids in the whole plant and plant parts of Teucrium chamaedrys L. var. glanduliferum Haussk J. Med. Plant Res. 4 2010 2092 2098
44. K. Thaipong, U. Boonprakob, K. Crosby, L. Cisneros-Zevallos, and D.H. Byrne Comparison of ABTS, DPPH, FRAP, and ORAC assays for estimating antioxidant activity from guava fruit extracts J. Food Comp. Anal. 19 2006 669 675
45. A. Ulubelen, G. Topcu, and U. Sonmez Chemical and biological evaluation of genus Teucrium A. Rahman, Studies in Natural Products Chemistry - Bioactive Natural Products (Part D) 2000 Elsevier Amsterdam 591 648
46. A. Vazquez-Flota, and V. De Luca Jasmonate modulates development and light-regulated alkaloid biosynthesis in Catharanthus roseus Phytochemistry 49 1998 395 402
47. C. Wang, J. Wu, and X. Mei Enhancement of Taxol production and excretion in Taxus chinensis cell culture by fungal elicitation and medium renewal Appl. Microbiol. Biotechnol. 55 2001 404 410
48. J.F. Xu, C.B. Liu, A.M. Han, P.S. Feng, and Z.G. Su Strategies for the improvement of salidroside production in cell suspension cultures of Rhodiola sachalinensis Plant Cell Rep. 17 1998 288 293
49. R. Yang, and K. Shetty Stimulation of rosmarinic acid in shoot cultures of oregano (Origanum vulgare) clonal line in response to proline, proline analogue, and proline precursors J. Agric. Food Chem. 46 1998 2888 2893
50. K. Yazaki, K. Takeda, and M. Tabata Effects of methyl jasmonate on shikonin and dihydroechinofuran production in Lithospermum cell cultures Plant Cell Physiol. 38 1997 776 782
51. Y. Yukimune, H. Tabata, Y. Higashi, and Y. Hara Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures Nat. Biotechnol. 14 1996 1129 1132
52. C.H. Zhang, J.Y. Wu, and G.Y. He Effects of inoculum size and age on biomass growth and paclitaxel production of elicitor-treated Taxus yunnanensis cell cultures Appl. Microbiol. Biotechnol. 60 2002 396 402
53. J. Zhao, Q. Hu, and W.H. Zhu Enhanced catharanthine production in Catharanthus roseus cell cultures by combined elicitor treatment in shake flasks and bioreactors Enz. Microb. Technol. 28 2001 673 681
54. A. Zuppini, B. Baldan, R. Millioni, F. Favaron, L. Navazio, and P. Mariani Chitosan induces Ca2+-mediated programmed cell death in soybean cells New Phytol. 161 2003 557 568