Biotechnological Approaches for the Production of some Promising Plant-Based Chemotherapeutics

Medicinal Plant Biotechnology: From Basic Research to Industrial Applications

Volumn , Issue , 2008, Pages 117-156

  Baldi, Ashish ^a   Bisaria, V S ^a   Srivastava, A K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Cell; Chemotherapeutics; Cultivation; Economy; Synthetic drugs

Indexed keywords

EID: 84889461799     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619771.ch7     Document Type: Chapter

References (185)

1. Farnsworth, N.R., Bingel, A.S. Problems and prospects of discovering new drugs from higher plants by pharmacological screening, Wagner, H., Wolff, P. (Eds.), New natural products with pharmacological, biological or therapeutic activity. Springer-Verlag, New York, 1977, pp. 1-22.
2. Principe, P.P. Moneterizing the pharmacological benefits of plants. In: Balick, M.J., Elisabetsky, E., Laird, S.A. (Eds.), Medicinal Plant Resources of the Tropical Forest. Columbia University Press, New York, 1996, pp. 191-218.
3. Cragg, G.M., Newman, D.J., Snader, K.M. Natural products in drug discovery and development. J. Nat. Prod. 1997, 60, 52-60.
4. Cragg, G.M., Newman, D.J. Antineoplastic agents from natural sources: Achievements and future directions. Expert Opin. Investig. Drugs 2000, 9, 2783-2797.
5. Pezzuto, J.M. Plant-derived anticancer agents. Biochem. Pharmacol. 1997, 53, 121-133.
6. Cragg, G.M., Scherpartz, S.A., Suffness, M., Grever, M.R. The Taxol supply crisis. New NCI policies for handling the largescale production of novel natural product anticancer and anti-HIV agents. J. Nat. Prod. 1993, 56, 1657-1668.
7. Verpoorte, R., Contin, A., Memelink, J. Biotechnology for the production of plant secondary metabolites. Phytochem. Rev. 2002, 1, 13-25.
8. Kadkade, P.G. Formation of podophyllotoxin by Podophyllum peltatum tissue cultures. Naturwissenschaften 1981, 68, 481-482.
9. Kadkade, P.G. Growth and podophyllotoxin production in callus tissues of Podophyllum peltatum. Plant Sci. Lett. 1982, 25, 107-115.
10. Van Uden, W., Pras, N., Visser, J.F., Malingre, T.M. Detection and identification of podophyllotoxin produced by cell cultures derived from Podophyllum hexandrum Royle. Plant Cell Rep. 1989, 8, 165-168.
11. Heyenga, A.G., Lucas, J.A., Dewick, P.M. Production of tumor-inhibitory lignans in callus cultures of Podophyllum hexandrum. Plant Cell Rep. 1990, 9, 382-385.
12. Berlin, J., Bedorf, N., Molleschott, C., Wray, V., Sasse, F., Hofle, G. On the podophyllotoxins of root cultures of Linum flavum. Planta Med. 1988, 54, 204-206.
13. Van Uden, W., Pras, N., Batterman, S., Viser, J.F., Malingre, T.M. The accumulation and isolation of coniferin from a high-producing cell suspension of Linum flavum L. Planta 1990, 183, 25-30.
14. Smollny, T., Wichers, H., De-Rijk, T., Van-Zwam, A., Shahsavari, A., Alfermann, A.W. Formation of lignans in suspension cultures of Linum album. Planta Med. 1992, 58, A622-A624.
15. Wichers, H.J., Versluis-De-Haan, G.G., Marsman, J.W., Harkes, M.P. Podophyllotoxin related lignans in plants and cell cultures of Linum flavum. Phytochemistry 1991, 30, 3601-3604.
16. Muranaka, T., Miyata, M., Kazutaka, I., Tachibana, S. Production of podophyllotoxin in Juniperus chinensis callus cultures treated with oligosaccharides and a biogenetic precursor. Phytochemistry 1998, 49, 491-496.
17. Woerdenbag, H.J., Van Uden, W., Frijlink, H.W., Lerk, C.F., Pras, N., Malingre, T.M. Increased podophyllotoxin production in Podophyllum hexandrum cell suspension cultures after feeding coniferyl alcohol as a betacyclodextrin complex. Plant Cell Rep. 1990, 9, 97-100.
18. Chattopadhyay, S., Srivastava, A.K., Bhojwani, S.S., Bisaria, V.S. Development of suspension culture of Podophyllum hexandrum for the production of podophyllotoxin. Biotechnol Lett. 2001, 23, 2063-2066.
19. Fett-Neto, A.G., Melanson, S.J., Nicholson, S.A., Pennington, J.J., Dicosmo, F. Improved taxol yield by aromatic carboxylic acid and amino acid feeding to cell cultures of Taxus cuspidata. Biotechnol Bioeng. 1994, 44, 967-971.
20. Wickremesinhe, E.R.M., Arteca, R.N. Taxus cell suspension cultures: optimizing growth and production of Taxol. J. Plant Physiol. 1994, 144, 183-188.
21. Kim, J.H., Yun, J.J., Hwang, Y.S., Byun, S.Y., Kim, D.I. Production of Taxol and related taxanes in Taxus brevifolia cell cultures: effect of sugar. Biotechnol Lett. 1995, 17, 101-106.
22. Pestchanker, L., Roberts, S.C., Shuler, M.L. Kinetics of taxol production and nutrient use in suspension cultures of Taxus cuspidata in shake flasks and a Wilson-type bioreactor. Enzyme Microb. Tech. 1996, 19, 256-260.
23. Hirasuna, T.J., Pestchanker, L.J., Srinivasan, V., Shuler, M.L. Taxol production in suspension cultures of Taxus baccata. Plant Cell Tissue Organ Cult. 1996, 44, 95-102.
24. Ketchum, R.E.B., Gibson, D.M. Paclitaxel production in suspension cell cultures of Taxus. Plant Cell Tissue Organ Cult. 1996, 46, 9-16.
25. Bringi, V., Kadkade, P.G., Prince, C.L., Schubmehl, B.F., Kane, E.J., Roach, B. Enhanced production of Taxol and taxanes by cell cultures of Taxus species (1995) US Patent 5407816.
26. Yakimune, Y., Tabata, H., Higashi, Y., Hara, Y. Methyl jasmonate-induced overproduction of paclitaxel and baccatin III in Taxus cell suspension cultures. Nat. Biotechnol. 1996, 14, 1129-1132.
27. Parc, G., Canaguier, A., Landre, P., Hocquemiller, R., Chriqui, D., Meyer, M. Production of taxoids with biological activity by plants and callus culture from selected Taxus genotypes. Phytochemistry 2002, 59, 725-730.
28. Fulzele, D.P., Satdive, R.K., Pol, B.B. Growth and production of camptothecin by cell suspension cultures of Nothapodytes foetida. Planta Med. 2001, 67, 150-152.
29. Sakato, K., Misawa, M. Effects of chemical and physical conditions on growth of Camptotheca acuminata cell cultures. Agric. Biol. Chem. 1974, 38, 491-497.
30. Van Hengal, A.J., Harkes, M.P., Witchers, H.J., Hesselinic, P.G.M., Buitglaar, R.M. Characterization of callus formation and camptothecin production by cell lines of Camptotheca acuminata. Plant Cell Tissue Organ Cult. 1992, 28, 11-18.
31. Wiedenfeld, H., Furmanowa, M., Roeder, E., Guzewska, J., Gustowski, W. Camptothecin and 10-hydroxycamptothecin in callus and plantlets of Camptotheca acuminata. Plant Cell Tissue Organ Cult. 1997, 49, 213-218.
32. Sakata, K., Morita, E., Takezono, T. Annual Meeting of the Society of Agricultural Chemistry. Fukuoka, Japan, March 30, 1990.
33. Arumugam, N., Bhojawani, S.S. Somatic embryogenesis in tissue cultures of Podophyllum hexandrum. Can. J. Bot. 1990, 68, 487-491.
34. Nadeem, M., Palni, L.M.S., Purohit, A.N., Pandey, H., Nandi, S.K. Propagation and conservation of Podophyllum hexandrum Royle: an important medicinal herb. Biol. Conserv. 2000, 92, 121-129
35. Moraes-Cerdeira, R.M., Burandt, C.L., Jr, Bastos, J.K., Nanayakkara, N.P.D., McChesney, J.D. In vitro propagation of Podophyllum peltatum. Planta Med. 1998, 64, 42-46.
36. Van Uden, W., Homan, B., Woerdenbag, H.J., Pras, N., Malingre, T.M., Wichers, H.J. Isolation, purification and cytotoxicity of 5-methoxypodophyllotoxin, a lignan from a root culture of Linum flavum. J. Nat. Prod. 1992, 55, 102-110.
37. Van Uden, W., Pras, N., Homan, B., Malingre, T.M. Improvement of the production of 5-methoxypodophyllotoxin using a new selected root culture of Linum flavum L. Plant Cell Tissue Organ Cult. 1991, 27, 115-121.
38. Giri, A., Giri, C.C., Dhingra, V., Narasu, M.L. Enhanced podophyllotoxin production from Agrobacterium rhizogenes transformed cultures of Podophyllum hexandrum. Nat. Prod. Lett. 2001, 15, 229-235.
39. Oostdam, A., Mol, J.N.M., van der Plas, L.H.W. Establishment of hairy root cultures of Linum flavum producing the lignan 5-methoxypodophyllotoxin. Plant Cell Rep. 1993, 12, 474-477.
40. Lin, H., Kwok, K.H., Doran, P.M. Production of podophyllotoxin using cross-species coculture of Linum flavum hairy roots and Podophyllum hexandrum cell suspensions. Biotechnol. Prog. 2003, 19, 1417-1426.
41. Han, K.H., Fleming, P., Walker, K., Loper, M., Chilton, W.S., Mocek, U., Gordon, M.P., Floss, H.G. Genetic transformation of mature Taxus: an approach to genetically control the in vitro production of the anticancer drug, taxol. Plant Sci. 1994, 95, 187-196.
42. Roja, G., Heble, M.R. The quinoline alkaloids camptothecin and 9-methoxycamptothecin from tissue cultures and mature trees of Nothapodytes foetida. Phytochemistry 1994, 36, 65-66.
43. Kitajima, M., Fischer, U., Nakamura, M., Ohsawa, M., Ueno, M., Takayama, H., Unger, M., Stöckigt, J., Aimi, N. Anthraquinones from Ophiorriza pumila tissue and cell cultures. Phytochemistry 1998, 48, 107-111.
44. Van Uden, W., The biotechnological production of podophyllotoxin and related cytotoxic lignans by plant cell cultures. Pharm. World Sci. 1993, 15, 41-43.
45. Chattopadhyay, S., Srivastava, A.K., Bisaria, V.S. Optimization of culture parameters for production of podophyllotoxin in suspension culture of Podophyllum hexandrum. Appl. Biochem. Biotechnol. 2002, 102/103, 381-393
46. Chattopadhyay, S., Srivastava, A.K., Bhojwani, S.S., Bisaria, V.S. Production of podophyllotoxin by plant cell cultures of Podophyllum hexandrum in bioreactor. J. Ferment. Bioeng. 2002, 93, 215-220.
47. Chattopadhyay, S., Mehra, R.S., Srivastava, A.K., Bhojwani, S.S., Bisaria, V.S. Effect of major nutrients on podophyllotoxin production in Podophyllum hexandrum suspension cultures. Appl. Microbiol. Biotechnol. 2003, 60, 541-546.
48. Wang, Z.Y., Zhong, J.J. Combination of conditioned medium and elicitation enhances taxoid production in bioreactor cultures of Taxus chinensis cells. Biochem. Eng. J. 2002, 12, 93-97.
49. Choi, H.K., Kim, S.I., Son, J.S., Hong, S.S., Lee, H.S., Chung, I.S., Lee, H.J. Intermittent maltose feeding enhances paclitaxel production in suspension culture of Taxus chinensis cells. Biotechnol. Lett. 2000, 22, 1793-1796.
50. Mirjalili, N., Linden, J.C. Gas phase composition effects on suspension cultures of Taxus cuspidata. Biotechnol. Bioeng. 1995, 48, 123-132.
51. Linden, J.C., Haigh, J.R., Mirjalili, N., Phisaphalong, M. Gas concentration effects on secondary metabolite production by plant cell cultures. Adv. Biochem. Eng. Biotechnol. 2001, 72, 28-62.
52. Smith, M.A.L. Large-scale production of secondary metabolites. In: Terzi, M., Cella, R., Falavigna, A. (Eds.), Current Issues in Plant Molecular and Cellular Biology. Kluwer Academic Publishers, Dordrecht, The Netherlands, 1995, pp. 669-674.
53. Stierle, A., Strobel, G., Stierle, D. Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of pacific yew. Science 1993, 260, 214-216.
54. Altstadt, T.J., Fairchild, C.R., Golik, J., Johnston, K.A., Kadow, J.F., Lee, F.Y., Long, B.H., Rose, W.C., Vyas, D.M., Wong, H., Wu, M.J., Wittman, M.D. Synthesis and antitumor activity of novel C-7 paclitaxel ethers: discovery of BMS-184476. J. Med. Chem. 2001, 44, 4577-4583.
55. Pezzutto, J.M. Taxol production in plant cell culture comes of age. Nat. Biotechnol. 1996, 14, 1083.
56. Van Uden, W., Pras, N., Malingre, T.M. On the improvement of the podophyllotoxin production by phenylpropanoid precursor feeding to cell cultures of Podophyllum hexandrum Royle. Plant Cell Tissue Organ Cult. 1990, 23, 217-224.
57. Fett-Neto, A.G., Dicosmo, F., Reynolds, W.F., Sakata, K. Cell culture of Taxus as a source of the antineoplastic drug taxol and related taxanes. Biotechnology 1992, 10, 1572-1575.
58. Van Uden, W., Pras, N., Malingre, T.M. The accumulation of podophyllotoxin-âd-glucoside by cell suspension cultures derived from the conifer Callitris drummondii. Plant Cell Rep. 1990, 9, 257-260.
59. Wang, H.Q., Yu, J.T., Zhong, J.J. Significant improvement of taxane production in suspension cultures of Taxus chinensis by sucrose feeding strategy. Process Biochem. 2000, 35, 479-483.
60. Luo, J., Mei, X., Liu, L., Hu, D.W. Improved paclitaxel production by fed batch suspension cultures of Taxus chinensis in bioreactors. Biotechnol. Lett. 2002, 24, 561-565.
61. Fleming, P.E., Knaggs, A.R., He, X.G., Mocek, U., Floss, H.G. Biosynthesis of taxoids. Mode of attachment of the taxol side chain. J. Am. Chem. Soc. 1994, 116, 4137.
62. Srinivasan, V., Ciddi, V., Bringi, V., Shuler, M.L., Metabolic inhibitors, elicitors, and precursors as tools for probing yield limitation in taxane production by Taxus chinensis cell cultures. Biotechnol. Prog. 1996, 12, 457-465.
63. Strobel, G.A., Stierle, A., Vankujik, F.J.G.M. Factors influencing the in vitro production of radiolabelled taxol by pacific yew, Taxus brevifolia. Plant Sci. 1992, 84, 65-74.
64. Mamatha, R. Studies in tissue cultures of taxus species and other higher plants. PhD thesis, Kakatiya University, Warangal, A.P., India, 2000.
65. Silvestrine, A., Pasqua, G., Botta, B., Monacelli, B., Van der Heijden, R., Verpoorte, R. Effects of alkaloid precursor feeding on a Camptotheca acuminata cell line. Plant Physiol. Biochem. 2002, 40, 749-753.
66. Aapro, M. Docetaxel versus doxorubicin in patients with metastatic breast cancer who have failed alkylating chemotherapy: a preliminary report of the randomized phase III trial. Semin. Oncol. 1998, 25, 7-11.
67. Schmitt, J., Petersen, M. Influence of methyl jasmonate and coniferyl alcohol on pinoresinol and matairesinol accumulation in a Forsythia intermedia suspension culture. Plant Cell Rep. 2002, 20, 885-889.
68. Van Furden, B., Humburg, A., Fuss, E. Influence of methyl jasmonate on podophyllotoxin and 6-methoxypodophyllotoxin accumulation in Linum album cell suspension cultures. Plant Cell Rep. 2005, 24, 312-317.
69. Shams-Ardakani, M., Hemmati, S., Mohagheghzadeh, A. Effect of elicitors on the enhancement of podophyllotoxin biosynthesis in suspension cultures of Linum album. DARU 2005, 13, 56-60.
70. Yu, L.J., Lan, W.Z., Qin, W.M., Jin, W.W., Xu, H.B. Oxidative stress and taxol production induced by fungal elicitor in cell suspension cultures of Taxus chinensis. Biol. Plant. (Prague) 2002, 45, 459-461.
71. Yuan, Y.J., Li, C., Hu, Z.D., Wu, J.C. A Double oxidative burst for taxol production in suspension cultures of Taxus chinensis var. mairei induced by oligosaccharide from Fusarium oxysprum. Enzyme Microb. Technol. 2002, 30, 774-778.
72. Yuan, Y.J., Li, C., Hu, Z.D., Wu, J.C., Zeng, A.P. Fungal elicitor-induced cell apoptosis in suspension cultures of Taxus chinensis var. mairei for taxol production. Process Biochem. 2002, 38, 193-198.
73. Mirajilili, N., Linden, J.C. Methyl jasmonate induced production of taxol in suspension cultures of Taxus cuspidate: ethylene interaction and induction models. Biotechnol. Prog. 1996, 12, 110-118.
74. Ketchum, R.E.B., Gibson, D.M., Croteau, R.B., Shuler, M.L. The kinetics of taxoid accumulation in cell suspension cultures of Taxus following elicitation with methyl jasmonate. Biotechnol. Bioeng. 1999, 62, 97-105.
75. Baebler, S., Camloh, M., Kovac, M., Ravnikar, M., Zel, J. Jasmonic acid stimulates taxane production in cell suspension culture of yew (Taxus media). Planta Med. 2002, 68, 475-476.
76. Yuan, Y.J., Hu, G.W., Wang, C.G., Jing, Y., Zhou, Y.Q., Shen, P.W. Effect of rare earth compounds on the growth, taxol biosynthesis and release in Taxus cuspidata cell culture. J. Chin. Rare Earth Soc. 1998, 16, 56-60.
77. Wu, J., Wang, C., Mei, X. Stimulation of taxol production and excretion in Taxus spp. cell cultures by rare earth chemical lanthanum. J. Biotechnol. 2001, 85, 67-73.
78. Ciddi, V., Srinivasan, V., Shuler, M.L. Elicitation of Taxus sp. cell cultures for production of taxol. Biotechnol. Lett. 1995, 17, 1343-1346.
79. Wang, C., Wu, J., Mei, X. Enhanced taxol production and release in Taxus chinensis cell suspension cultures with selected organic solvents and sucrose feeding. Biotechnol. Prog. 2001, 17, 89-94.
80. Yu, L.J., Lan, W.Z., Qin, W.M., Xu, B.H. Effects of salicylic acid on fungal elicitor induced membrane-lipid peroxidation and taxol production in cell suspension cultures of Taxus chinensis. Process Biochem. 2001, 37, 477-482.
81. Dong, H.D., Zhong, J.J. Enhanced taxane production in bioreactor cultivation of Taxus chinensis cells by combining elicitation, sucrose feeding and ethylene incorporation. Enzyme Microb. Technol. 2002, 31, 116-121.
82. Cusido, R.M., Palazo, M., Bonfill, M., Navia-Osorio, A., Morales, M., Pinol, M.T. Improved paclitaxel and baccatin III production in suspension cultures of Taxus media. Biotechnol. Prog. 2002, 18, 418-423.
83. Zhang, C.H., Wu, J.Y. Ethylene inhibitors enhance elicitor-induced paclitaxel production in suspension cultures of Taxus spp. cells. Enzyme Microb. Technol. 2003, 32, 71-77.
84. Laskaris, G., Bounkhay, M., Theodoridis, G., Van der Heijden, R., Verpoorte, R., Jaziri, M. Induction of geranylgeranyl diphosphate synthase activity and taxane accumulation in Taxus baccata cell cultures after elicitation by methyl jasmonate. Plant Sci. 1999, 147, 1-8.
85. Luo, J., He, G.Y. Optimization of elicitors and precursors for paclitaxel production in cell suspension culture of Taxus chinensis in the presence of nutrient feeding. Process Biochem. 2004, 39, 1073-1079.
86. Khosroushahi, A.Y., Valizadeh, M., Ghasempour, A., Khosrowshahli, M., Naghdibadi, M., Dadpour, M.R., Omidi, Y. Improved Taxol production by combination of inducing factors in suspension cell culture of Taxus baccata. Cell Biol. Inter. 2005, 30, 262-269.
87. Kwon, I.C., Yoo, Y.J., Lee, J.H., Hyun, J.O. Enhancement of taxol production by in situ recovery of product. Process Biochem. 1998, 33, 701-707.
88. Kondo, O., Honda, H., Taya, M., Kobayashi, T. Comparison of growth properties of carrot hairy root in various bioreactors. Appl. Microbiol. Biotechnol. 1989, 32, 291-294.
89. Kutney, J.P., Hewitt, G., Jarvis, T.C., Palaty, J., Retting, S.J. Studies with plant cell cultures of Catharanthus roseus. Oxidative coupling of dibenzylbutanolides catalyzed by plant cell culture extracts. Can. J. Chem. 1992, 70, 2115-2133.
90. Van Uden, W., Holidi Oeij, K., Woerdenbag, H.J., Pras, N. Glucosylation of cyclodextrin-complexed podophyllotoxin by cell cultures of Linum flavum. Plant Cell Tissue Organ Cult. 1993, 34, 169-175.
91. Kutney, J.P. Biotechnology and synthetic chemistry routes to clinically important compounds. Pure Appl. Chem. 1999, 71, 1025-1032.
92. Puricelli, L., Caniato, R., Delle Monache, G. Biotransformation of a dibenzylbutanolide to podophyllotoxin analogues by shoot cultures of Haplophyllum patavinum. Chem. Pharm. Bull. 2003, 51, 848-850.
93. Koulman, A., Beekman, A.C., Pras, N., Quax, J.W. The bioconversion process of deoxypodophyllotoxin with Linum flavum cell cultures. Planta Med. 2003, 69, 739-744.
94. Chen, T.S., Li, X., Bollag, D., Liu, Y.C., Chang, C.J. Biotransformation of taxol. Tetrahedron Lett. 2001, 42, 3787-3789.
95. Hamada, H., Furaya, T. Recent advances in plant biotransformation. Plant Tiss. Cult. Biotech. 1996, 2, 52-60.
96. Veeresham, C., Rao, M.A., Babu, P.C., Mamatha, R., Kokate, C.K. Biotransformation of paclitaxel (Taxol) by plant cell cultures. Indian Drugs 2000, 37, 86-89.
97. Chattopadhyay, S., Bisaria, V.S., Srivastava, A.K. Enhanced production of podophyllotoxin by Podophyllum hexandrum using in situ cell retention bioreactor. Biotechnol. Prog. 2003, 19, 1026-1028.
98. Chattopadhyay, S., Bisaria, V.S., Bhojwani, S.S., Srivastava, A.K. Enhanced production of podophyllotoxin by fed-batch cultivation of Podophyllum hexandrum. Can. J. Chem. Eng. 2003, 81, 1-8.
99. Arroo, R.R.J., Alfermann, A.W., Medarde, M., Petersen, M., Pras, N., Woolley, J.G. Plant cell factories as a source for anti-cancer lignans. Phytochem. Rev. 2002, 1, 27-35.
100. Srinivasan, V.L., Pestchanker, L., Moser, S., Hirasuna, T., Tatlcek, R.A., Schular, M.L. Taxol production in bioreactors: Kinetics of biomass accumulation, nutrient uptake, and taxol production by cell suspensions of Taxus baccata. Biotech. Bioeng. 1995, 47, 666-676.
101. Seki, M., Ohzora, C., Takede, M., Furasaki, S. Taxol (paclitaxel) production using free and immobilized cells of Taxus cuspidata. Biotech. Bioeng. 1997, 53, 214-219.
102. Wang, S.J., Zhong, J.J. A novel centrifugal impeller bioreactor. I. Fluid circulation, mixing, and liquid velocity profiles. Biotechnol. Bioeng. 1996, 51, 511-519.
103. Zhong, J.J., Wang, S.J., Wang, H.Q. A new centrifugal impeller reactor and its application to plant cell cultures. In: Horizon of biochemical engineering. The Society of Chemical Engineers, Japan, Tokyo, 1997, pp. 175-179.
104. Navia-Osorio, A., Garden, H., Cusido, R.M., Palazon, J., Alfermann, A.W., Pinol, M.T. Taxol and baccatin III production in suspension cultures of Taxus baccata and Taxus wallichiana in an airlift bioreactor. J. Plant Physiol. 2002, 159, 97-102.
105. Son, S.H., Choi, S.M., Lee, Y.H., Choi, K.B., Yun, S.R., Kim, J.K., Park, H.J., Kwon, O.W., Noh, E.W., Seon, J.H., Park, Y.G. Large-scale growth and taxane production in cell cultures of Taxus cuspidata (Japanese yew) using a novel bioreactor. Plant Cell Rep. 2000, 19, 628-633.
106. Hu, W.W., Zhong, J.J. Effect of bottom clearance on performance of airlift bioreactor in high-density culture of Panax notoginseng cells. J. Biosci. Bioeng. 2001, 92, 389-392.
107. Pan, Z.W., Wang, H.Q., Zhong, J.J. Scale-up study on suspension cultures of Taxus chinensis cells for production of taxane diterpene. Enzyme Microb. Technol. 2000, 27, 714-723.
108. Zhong, J.J., Pan, Z.W., Wang, Z.Y., Wu, J.Y., Chen, F., Takagi, M., Yoshida, A.T Effect of mixing time on taxoid production in suspension cultures of Taxus chinensis in a centrifugal impeller bioreactor. J. Biosci. Bioeng. 2002, 94, 244-250.
109. Xia, Z.Q., Costa, M.A., Proctor, J., Davin, L.B., Lewis, N.G. Dirigent-mediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum. Phytochemistry 2000, 55, 537-549.
110. Larsen, K. Cloning and characterization of a ryegrass (Lolium perenne) gene encoding cinnamoyl-CoA reductase (CCR). Plant Sci. 2004, 166, 569-581.
111. Windhövel, J., Fuss, E., Alfermann, A.W. The biosynthesis of lignans in Linum album: Cinnamoyl-CoA: NADP oxidoreductase: Abstract (Biochemistry) (2001) www.biologie.uni-erlangen.de/pharmabiol/Abstract/Biochemistry.
112. Hoshida, H., Nakao, M., Kazava, N., Kubo, K., Hakukawa, T., Morimasa, K., Akada, R., Nishizawa, Y. Isolation of five lactase gene sequences from the whiterot fungus Trametes sanguinea by PCR, and cloning, characterization and expression of the laccase cDNA in yeasts. J. Biosci. Bioeng. 2001, 92, 372-380.
113. De Melis, L.E., Whiteman, P.H., Stevenson, T.W. Isolation and characterisation of a cDNA clone encoding cinnamyl alcohol dehydrogenase in Eucalyptus globulus Labill. Plant Sci. 1999, 143, 173-182.
114. Schwelm, A., Fuss, E., Schönell, B., Windhövel, J., Alfermann, A.W. The biosynthesis of cytotoxic lignans in Linum album: phenylalanine ammonia lyase and cinnamoyl alcohol dehydrogenase: Abstract (Biochemistry) (2001) www.biologie.uni-erlangen.de/pharmabiol/Abstract/Biochemistry.
115. Seidel, V., Windhövel, J., Eaton, G., Alfermann, A.W., Arroo, R.R.J., Woolley, J.G. Podophyllotoxin biosynthesis in Linum album cell cultures-the role of phenylpropanoid ring substitution patterns: Abstract (Biochemistry) (2001) www.biologie.uni-erlangen.de/pharmabiol/Abstract/Biochemistry.
116. Hegener, U., Fuss, E., Alfermann, A.W. Biosynthesis of cytotoxic lignans in Linum album: caffeic acid 3-O-methyltransferase: Abstract (Biochemistry) (2001) www.biologie.uni-erlangen.de/pharmabiol/Abstract/Biochemistry.
117. Xue, Z., Brodellius, P. Kinetin induced caffeic acid O-methyltransferases in cell suspension cultures of Vanila planifolia Andr. and isolation of caffeic acid O-methyltransferases cDNAs. Plant Physiol. Biochem. 1998, 36, 779-788.
118. Xia, Z.Q., Costa, M.A., Pellisier, H., Davin, L.B., Lewis, N.G. Secoisolariciresinol dehydrogenase purification, cloning and functional expression. J. Biol. Chem. 2001, 276, 12614-12623.
119. Kranz, K., Petersen, M. Â-Peltatin 6-Omethyltransferase from suspension cultures of Linum nodiflorum. Phytochemistry 2003, 64, 453-458.
120. Kuhlmann, S., Molog, G., Empt, U., Van Uden, W., Pras, N., Alfermann, A.W., Petersen, M. characterisation of deoxypodophyllotoxin 5-hydroxylase (dop5h), a cytochrome p450-dependent enzyme in lignan biosynthesis of Linum species: Abstract (Biochemistry) (2001) www.biologie.uni-erlangen.de/pharmabiol/Abstract/Biochemistry.
121. Gavnholt, B., Larsen, K., Rasmussen, S.K. Isolation and characterisation of laccase cDNAs from meristematic and stem tissues of ryegrass (Lolium perenne). Plant Sci. 2002, 162, 873-885.
122. Piquemal, J., Lapierre, C., Myton, K., O'Connell, A., Schuch, W., Grima-Pettenati, J., Boudet, A.M. Downregulation of cinnamoyl-CoA reductase induces significant changes of lignin profiles in transgenic tobacco plants. Plant J. 1998, 13, 71-83.
123. Eisenreich, W., Menhard, B., Hylands, P.J., Zenk, M.H., Bacher, A. Studies on the biosynthesis of Taxol: the taxane carbon skeleton is not of mevalonoid origin of special interest. Proc. Natl. Acad. Sci. USA 1996, 93, 6431-6436.
124. Rohmer, M., Knani, M., Simonin, P., Sutter, B., Sahm, H. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate. Biochem. J. 1993, 295, 517-524.
125. Lichtenthaler, H.K., Rohmer, M., Schwender, J. Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiol. Plant. 1997, 101, 643-652.
126. Lichtenthaler, H.K. The 1-deoxy-Dxylulose-5-phosphate pathway of isoprenoid biosynthesis in plants. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1999, 50, 47-65.
127. Koepp, A.E., Hezari, M., Zajicek, J., Vogel, B.S., Lafever, R.E., Lewis, N.G., Croteau, R. Cyclization of geranylgeranyl diphosphate to taxa-4(5),11(12)-diene is the first committed step of Taxol biosynthesis in Pacific yew. J. Biol. Chem. 1995, 270, 8686-8690.
128. Hezari, M., Lewis, N.G., Croteau, R. Purification and characterization of tax-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of Taxol biosynthesis. Arch. Biochem. Biophys. 1995, 322, 437-444.
129. Hefner, J., Rubenstein, S.M., Ketchum, R.E.B., Gibson, D.M., Williams, R.M., Croteau, R. Cytochrome P450-catalyzed hydroxylation of taxa-4(5),11(12)-diene to taxa-4(20),11(12)-dien-5a-ol: the first oxygenation step in Taxol biosynthesis. Chem. Biol. 1996, 3, 479-489.
130. Vazquez, A., Williams, R.M. Studies on the biosynthesis of taxol. Synthesis of taxa-4(20),11(12)-diene-2,5-diol. J. Org. Chem. 2000, 65, 7865-7869.
131. Floss, H.G., Mocek, U. Biosynthesis of taxol. In: Suffness, M. (Ed.), Taxol science and applications. CRC Press, Boca Raton, 1995, pp. 191-298.
132. Kingston, D.G.I., Molinero, A.A., Rimoldi, J.M. The taxane diterpenoids. Prog. Chem. Org. Nat. Prod. 1993, 61, 1-206.
133. Baloglu, E., Kingston, D.G.I. The taxane diterpenoids. J. Nat. Prod. 1999, 62, 1448-1472.
134. Wildung, M.R., Croteau, R. A cDNA clone for taxadiene synthase, the diterpene cyclase that catalyzes the committed step of Taxol biosynthesis. J. Biol. Chem. 1996, 271, 9201-9204.
135. Schoendorf, A., Rithner, C.D., Williams, R.M., Croteau, R.B. Molecular cloning of a cytochrome P450 taxane 10-hydroxylase cDNA from Taxus and functional expression in yeast. Proc. Natl. Acad. Sci. USA 2001, 98, 1501-1506.
136. Jennewein, S., Croteau, R. Taxol: biosynthesis, molecular genetics, and biotechnological applications. Appl. Microbiol. Biotechnol. 2001, 57, 13-19.
137. Jennewein, S., Rithner, C.D., Williams, R.M., Croteau, R.B. Taxol biosynthesis: taxane 13 alpha-hydroxylase is a cytochrome P450-dependent monooxygenase. Proc. Natl. Acad. Sci. USA 2001, 98, 13595-13600.
138. Walker, K., Ketchum, R.E., Hezari, M., Gatfield, D., Goleniowski, M., Barthol, A., Croteau, R. Partial purification and characterization of acetyl coenzyme A: taxa-4(20),11(12)-dien-5-alpha-ol O-acetyl transferase that catalyzes the first acylation step of taxol biosynthesis. Arch. Biochem. Biophys. 1999, 364, 273-279.
139. Walker, K., Croteau, R. Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Proc. Natl. Acad. Sci. USA 2000, 97, 583-587.
140. Walker, K., Scboendorf, A., Croteau, R. Molecular cloning of a taxa-4(20),11(12)-dien-5-ol-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Arch. Biochem. Biophys. 2000, 374, 371-380.
141. Huang, K.X., Huang, Q.L., Wildung, M.R., Croteau, R., Scott, A.I. Overproduction, in Escherichia coli, of soluble taxadiene synthase, a key enzyme in the Taxol biosynthetic pathway. Protein Expr. Purif. 1998, 13, 90-96.
142. Stockigt, J., Zenk, M.H. Strictosidine (isovincoside): the key intermediate in the biosynthesis of monoterpenoid indole alkaloids. J. Chem. Soc. Chem. Commun. 1977, 646-648.
143. Scott, A.I., Lee, S.L. Biosynthesis of the indole alkaloids-A cell-free system from Catharanthus roseus. J. Am. Chem. Soc. 1975, 97, 6906-6908.
144. Stockigt, J., Ruppert, M. Strictosidine-the biosynthetic key to monoterpenoid indole alkaloids. In: Barton, S.D., Nakanishi, K., Meth-Cohn, O. (Eds.), Comprehensive Natural Products Chemistry, Volume 4. Pergamon, Oxford, 1999, pp. 109-138.
145. Verpoorte, R., Van Der Heijden, R., Moreno, P.R.H. Biosynthesis of terpenoid indole alkaloids in Catharanthus roseus cells. In: Cordell, G.A. (Ed.), The Alkaloids. Academic Press, San Diego, 1997, pp. 221-299.
146. Hutchinson, C.R., Heckendorf, A.H., Straughn, J.L., Daddona, P.E., Cane, D.E. Biosynthesis of camptothecin: Definition of strictosamide as the penultimate biosynthetic precursor assisted by 13C and 1H NMR spectroscopy. J. Am. Chem. Soc. 1979, 101, 3358-3369.
147. Hemscheidt, T., Zenk, M.H. Glucosidases involved in indole alkaloid biosynthesis of Catharanthus cell cultures. FEBS Lett. 1980, 110, 187-191.
148. De Luca, V. Metabolic engineering of crops with the tryptophan decarboxylase of Catharanthus roseus. In: Verpoorte, R., Alfermann, A.W. (Eds.), Metabolic engineering of plant secondary metabolism. Kluwer Academic Press, Dordrecht, 2000, pp. 179-194.
149. Kutchan, T.M. Alkaloid biosynthesis-The basis for metabolic engineering of medicinal plants. Plant Cell 1995, 7, 1059-1070.
150. Canel, C., Lopez-Cardoso, M.I., Whitmer, S., Van Der Fits, L., Pasquali, G., Van Der Heijden, R., Hoge, J.H.C., Verpoorte, R. Effects of over-expression of strictosidine synthase and tryptophan decarboxylase on alkaloid production by cell cultures of Catharanthus roseus. Planta 1998, 205, 414-419.
151. Whitmer, S., Canel, C., Hallard, D., Goncalves, C., Verpoorte, R. Influence of precursor availability on alkaloid accumulation by transgenic cell lines of Catharanthus roseus. Plant Physiol. 1998, 116, 853-857.
152. Geerlings, A., Hallard, D., Martinez, C.A., Lopez, C.I., Van der Heijden, R., Verpoorte, R. Alkaloid production by a Cinchona officinalis 'Ledgeriana' hairy root culture containing constitutive expression constructs of tryptophan decarboxylase and strictosidine synthase cDNAs from Catharanthus roseus. Plant Cell Rep. 1999, 19, 191-196.
153. Whitmer, S. Aspects of terpenoid indole alkaloid formation by transgenic cell lines of Catharanthus roseus over-expressing tryptophan decarboxylase and strictosidine synthase. PhD Thesis, University of Leiden, The Netherlands, 1999.
154. Hallard, D. Transgenic plant cells for the production of indole alkaloids. PhD Thesis, University of Leiden, The Netherlands, 2000.
155. Menke, F.L.H., Champion, A., Kijne, J.W., Memelink, J. A novel jasmonateand elicitor-responsive element in the periwinkle secondary metabolite biosynthetic gene Str interacts with a jasmonate-and elicitor-inducible AP2-domain transcription factor, ORCA2. EMBO J. 1999, 18, 4455-4463.
156. Menke, F.L.H., Parchmann, S., Mueller, M.J., Kijne, J.W., Memelink, J. Involvement of the octadecanoid pathway and protein phosphorylation in fungal elicitor-induced expression of terpenoid indole alkaloid biosynthetic genes in Catharanthus roseus. Plant Physiol. 1999, 119, 1289-1296.
157. Menke, F.L.H. Elicitor signal transduction in Catharanthus roseus leading to terpenoid indole alkaloid biosynthetic gene expression. PhD Thesis, University of Leiden, The Netherlands, 1999.
158. Van Der Fits, L. Transcriptional regulation of stress-induced plant secondary metabolism. PhD Thesis, University of Leiden, The Netherlands, 2000.
159. Yamazaki, Y., Urano, A., Sudo, H., Kitajima, M., Takayama, H., Yamazaki, M., Aimi, N., Saito, K. Metabolite profiling of alkaloids and strictosidine synthase activity in camptothecinproducing plants. Phytochemistry 2003, 62, 461-470.
160. Misawa, M., Sakato, K., Tanaka, H., Hayashi, M., Samejima, M., Production of physiologically active substances by plant cell suspension cultures. In: Street, H.E. (Ed.), Tissue culture and Plant Science. Academic Press, London, New York, 1974, pp. 235-246.
161. Stahelin, H.F., Von Wartburg, A.V. The chemical and biological route from podophyllotoxin glucoside to etoposide. Cancer Res. 1991, 51, 5-15.
162. Imbert, T.F. Discovery of podophyllotoxins. Biochimie 1998, 80, 207-222.
163. Sjostrom, J., Blomqvist, C., Mouridsen, H., Pluzanska, A., Ottosson-Lonn, S., Bengtsson, N.O., Ostenstad, B., Mjaaland, I., Palm-Sjovall, M., Wist, E., Valvere, V., Anderson, H., Bergh, J. Docetaxel compared with sequential methotrexate and 5-fluorouracil in patients with advanced breast cancer after anthracycline failure: a randomized phase III study with crossover on progression by the Scandinavian Breast Group. Eur. J. Cancer 1999, 35, 1194-1201.
164. Fan, W. Possible mechanisms of paclitaxel-induced apoptosis. Biochem. Pharmacol. 1999, 57, 1215-1221.
165. Huang, Y., Fan, W. IkB kinase activation is involved in regulation of paclitaxelinduced apoptosis in human tumour cell lines. Mol. Pharmacol. 2002, 61, 105-113.
166. Johnson, K.R., Fan, W. Reduced expression of p53 and p21WAF1/CIP1 sensitizes human breast cancer cells to paclitaxel and its combination with 5-fluorouracil. Anticancer Res. 2002, 22, 1-8.
167. Johnson, K.R., Wang, L., Miller, M.C., Willingham, M.C., Fan, W. 5-Fluorouracil interferes with paclitaxel cytotoxicity against human solid tumour cells. Clin. Cancer Res. 1997, 3, 1739-1745.
168. Chabot, G.G. Clinical pharmacokinetics of irinotecan. Clin. Pharmacokinet. 1997, 33, 245-259.
169. Friedman, H.S., Petros, W.P., Friedman, A.H., Schaaf, L.J., Kerby, T., Lawyer, J., Parry, M., Houghton, P.J., Lovell, S., Rasheed, K., Cloughsey, T., Stewart, E.S., Colvin, O.M., Provenzale, J.M., Mclendon, R.E., Bigner, D.D., Cokgor, I., Haglund, M., Rich, J., Ashley, D., Malczyn, J., Elfring, G.L., Miller, L.L. Irinotecan therapy in adults with recurrent or progressive malignant glioma. J. Clin. Oncol. 1999, 17, 1516-1525.
170. Jiang, J.F., Lui, W.J., Ding, J. Regulation of telomerase activity in camptothecin induced apoptosis of leukemia HL-60 cells. Acta Pharmacol. Sin. 2000, 21, 759-764.
171. Van Uden, W., Pras, N., Malingre, T.M. The accumulation of podophyllotoxin-âd-glucoside by cell suspension cultures derived from the conifer Callitris drummondii. Plant Cell Rep. 1990, 9, 257-260.
172. Empt, U., Alfermann, A.W., Pras, N., Peterson, M. The use of plant cell cultures for the production of podophyllotoxin and related lignans. J. Appl. Bot. 2000, 74, 145-150.
173. Van Uden, W., Pras, N., Vossebeld, E.M., Mol, J.N.M., Malingre, T.M. Production of 5-methoxypodophyllotoxin in cell suspension cultures of Linum flavum L. Plant Cell Tissue Organ Cult. 1990, 20, 81-87.
174. Konuklugil, B., Schimdt, T.J., Alfermann, A.W. Accumulation of aryltetralin lactone lignans in cell suspension cultures of Linum nodiflorum. Planta Med. 1999, 65, 587-588.
175. Kutney, J.P., Arimoto, M., Hewitt, G.M., Jarvis, T.C., Sakata, K. Studies with plant cell cultures of Podophyllum peltatum L. I. Production of podophyllotoxin, deoxypodophyllotoxin, podophyllotoxone, and 4'-demethylpodophyllotoxin. Heterocycle 1991, 32, 2305-2309.
176. Dong, H.D., Zhong, J.J. Significant improvement of taxane production in suspension cultures of Taxus chinensis by combining elicitation with sucrose feed. Biochem. Eng. J. 2001, 8, 145-150.
177. Hermann, K.M. The shikimate pathway: Early steps in biosynthesis of aromatic compounds. Plant Cell 1995, 7, 907-910.
178. Hahlbrock, K., Scheel, D. Physiology and molecular biology of phenylpropanoid metabolism. Annu. Rev. Plant Physiol. Plant Mol. Biol. 1989, 40, 347-369.
179. Seidel, V., Windhövel, J., Eaton, G., Alfermann, A.W., Arroo, R.R.J., Medarde, M., Petersen, M., Wolley, J.G. Biosynthesis of podophyllotoxin in Linum album cell cultures. Planta 2002, 215, 1013-1039.
180. Lauvergeat, V., Lacomme, C., Lacombe, E., Lasserre, E., Roby, D., Grima-Pettenati, J. Two cinnamoyl-CoA reductase (CCR) genes from Arabidopsis thaliana are differentially expressed during development and in response to infection with pathogenic bacteria. Phytochemistry 2001, 57, 1187-1195.
181. Henges, A. Biosynthese und Kompartimentierung von Lignanen in Zellkulturen von Linum album. Dissertation, University of Dusseldorf, 1999.
182. Molog, M.G., Empt, U., Petersen, M., Van Uden, W., Pras, N., Alfermann, A.W. Deoxypodophyllotoxin 6-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum flavum involved in biosynthesis of cytotoxic lignans. Planta 2001, 214, 288-294.
183. Kuhlmann, S., Kranz, K., Lücking, B., Alfermann, A.W., Petersen, M. Aspects of cytotoxic lignan biosynthesis in suspension cultures of Linum nodiflorum. Phytochem. Rev. 2002, 1, 37-43.
184. Hezari, M., Croteau, R. Taxol biosynthesis: an update. Planta Med. 1997, 63, 291-295.
185. Collu, G., Unver, N., Peltenburg-Looman, A.M.G., Van der Heijden, R., Verpoorte, R., Memelink, J. Geraniol 10-hydroxylase, a cytochrome P450 enzyme involved in terpenoid indole alkaloid biosynthesis. FEBS Lett. 2001, 508, 215-220.