Production of Paclitaxel in Plant Cell Cultures

Medicinal Plant Biotechnology: From Basic Research to Industrial Applications

Volumn , Issue , 2008, Pages 515-528

  Tabata, Homare ^a  

^a MITSUI CHEMICALS INC   (Japan)

Author keywords

Acid; Drugs; Jasmonate; Lung cancer; Stimulators

Indexed keywords

EID: 38949157021     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619771.ch22     Document Type: Chapter

References (87)

1. Rowinsky, E.K., Cazenave, L.A., Donehower, R.C. Taxol: a novel investigational antimicrotubule agent. J. Natl. Cancer Inst. 1990, 82, 1247-1259.
2. Schiff, P.B., Fant, J., Horwitz, S.B. Promotion of microtubule assembly in vitro by taxol. Nature 1979, 277, 665-667.
3. Cragg, G.M., Schepartz, S.A., Suffuess, 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.
4. Stone, A.A., Chambers, T.C. Microtubule inhibitors elicit differential effects on MAP kinase (JNK, ERK, and p38) signaling pathways in human KB-3 carcinoma cells. Exp. Cell Res. 2000, 254, 110-119.
5. Stadheim, T.A., Xiao, H., Eastman, A. Inhibition of extracellular signal-regulated kinase (ERK) mediates cell cycle phase independent apoptosis in vinblastinetreated ML-1 cells. Cancer Res. 2001, 61, 1533-1540.
6. Boldt, S., Weidle, U.H., Kolch, W. The role of MAPK pathways in the action of chemotherapeutic drugs. Carcinogenesis 2002, 23, 1831-1838.
7. Okano, J., Rustgi, A.K. Paclitaxel induces prolonged activation of the Ras/MEK/ERK pathway independently of activating the programmed cell death machinery. J. Biol. Chem. 2001, 276, 19555-19564.
8. Wolfson, M., Yang, C.P., Horwitz, S.B. Taxol induces tyrosine phosphorylation of Shc and its association with Grb2 in murine RAW 264.7 cells. Int. J. Cancer 1997, 70, 248-252.
9. Boudny, V., Nakano, S. Src tyrosine kinase augments taxotere-induced apoptosis through enhanced expression and phosphorylation of Bcl-2. Br. J. Cancer 2002, 86, 463-469.
10. Kim, Y.M., Paik, S.G. Induction of expression of inducible nitric oxide synthase by Taxol in murine macrophage cells. Biochem. Biophys. Res. Commun. 2005, 326, 410-416.
11. Wieder, T., Essmann, F., Prokop, A., Schmelz, K., Schulze-Osthoff, K., Beyaert, R., Dorken, B., Daniel, P.T. Activation of caspase-8 in drug-induced apoptosis of B-lymphoid cells is independent of CD95/Fas receptor-ligand interaction and occurs downstream of caspase-3. Blood 2001, 97, 1378-1387.
12. Ofir, R., Seidman, R., Rabinski, T., Krup, M., Yavelsky, V., Weinstein, Y., Wolfson, M. Taxol-induced apoptosis in human SKOV3 ovarian and MCF7 breast carcinoma cells is caspase-3 and caspase-9 independent. Cell Death Differ. 2002, 9, 636-642.
13. Huisman, C., Ferreira, C.G., Broker, L.E., Rodriguez, J.A., Smit, E.F., Postmus, P.E., Kruyt, F.A., Giaccone, G. Paclitaxel triggers cell death primarily via caspaseindependent routes in the non-small cell lung cancer cell line NCI-H460. Clin. Cancer Res. 2002, 8, 596-606.
14. Huang, Y., Sheikh, M.S., Fornace, A.J., Jr., Holbrook, N.J. Serine protease inhibitor TPCK prevents Taxol-induced cell death and blocks c-Raf-1 and Bcl-2 phosphorylation in human breast carcinoma cells. Oncogene 1999, 18, 3431-3439.
15. Park, S.J., Wu, C.H., Gordon, J.D., Zhong, X., Emami, A., Safa, A.R. Taxol induces caspase-10-dependent apoptosis. J. Biol. Chem. 2004, 279, 51057-51067.
16. Rodi, D.J., Janes, R.W., Sanganee, H.J., Holton, R.A., Wallace, B.A., Makowski, L. Screening of a library of phage-displayed peptides identifies human bcl-2 as a taxolbinding protein. J. Mol. Biol. 1999, 285, 197-203.
17. Von Haefen, C., Wieder, T., Essmann, F., Schulze-Osthoff, K., Dorken, B., Daniel, P.T. Paclitaxel-induced apoptosis in BJAB cells proceeds via a death receptorindependent, caspases-3/-8-driven mitochondrial amplification loop. Oncogene 2003, 22, 2236-2247.
18. Fan, W. Possible mechanisms of paclitaxel-induced apoptosis. Biochem. Pharmacol. 1999, 57, 1215-1221.
19. Tudor, G., Aguilera, A., Halverson, D.O., Laing, N.D., Sausville, E.A. Susceptibility to drug-induced apoptosis correlates with differential modulation of Bad, Bcl-2 and Bcl-xL protein levels. Cell Death Differ. 2000, 7, 574-586.
20. Ding, A., Porteu, F., Sanchez, E., Nathan, C.F. Shared actions of endotoxin and taxol on TNF receptors and TNF release. Science 1990, 248, 370-372.
21. Croom, E.M., Jr. Taxus for taxol and taxoids. In: Suffness, M. (Ed.), TAXOL science and applications. CRC Press, New York, 1995, pp. 37-70.
22. Kikuchi, Y., Yatagai, M. The commercial cultivation of Taxus species and production of taxoids. In: Itokawa, H., Lee, K.-H. (Eds.), Taxus: The genus Taxus. Taylor & Francis, London, 2003, pp. 151-178.
23. Holton, R.A., Somoza, C., Kim, H.-B., Liang, F., Biediger, R.J., Boatman, P.D. First total synthesis of taxol. J. Am. Chem. Soc. 1994, 116, 1597-1599.
24. Nicolaou, K.C., Yang, Z., Liu, J.J., Ueno, H., Nantermet, P.G., Guy, R.K. Total synthesis of taxol. Nature 1994, 367, 630-634.
25. Gibson, D.M., Ketchum, R.E.B., Hirasuna, T.J., Shuler, M.L. Potential of plant cell culture for taxane production. In: Suffness, M. (Ed.), TAXOL science and applications. CRC Press, New York, 1995, pp. 71-95.
26. Christen, A.A., Gibson, D.M., Bland, J. Production of taxol or taxol-like compounds in cell culture. US Patent 5,019,504, 1991.
27. Gibson, D.M., Ketchum, R.E.B., Vance, N.C., Christen, A.A. Initiation and growth of cell lines of Taxus brevifolia (Pacific yew). Plant Cell Rep. 1993, 12, 479-482.
28. Kim, J.H., Yun, J.H., 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.
29. Srinivasan, V., Pestchanker, L., Moser, S., Hirasuna, T.J., Taticek, R.A., Shuler, M.L. Taxol production in bioreactors: Kinetics of biomass accumulation, nutrient uptake, and taxol production by cell suspensions of Taxus baccata. Biotechnol. Bioeng. 1995, 47, 666-676.
30. Mirjalili, N., Linden, J.C. Gas phase composition effects on suspension cultures of Taxus cuspidata. Biotechnol. Bioeng. 1995, 48, 123-132.
31. Mirjalili, N., Linden, J.C. Methyl jasmonate induced production of taxol in suspension cultures of Taxus cuspidata: ethylene interaction and induction models. Biotechnol. Prog. 1996, 12, 110-118.
32. Fett-Neto. A.G., Pennington, J.J., DiCosmo, F. Effect of white light on taxol and baccatin III accumulation in cell cultures of Taxus cuspidata Sieb and Zucc. J. Plant Physiol. 1995, 146, 584-590.
33. 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.
34. 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.
35. Bringi, V., Kadkade, P. Enhanced production of taxol and taxanes by cell cultures of Taxus species. WO patent 93/17121, 1993.
36. Choi, H., Kim, S., Son, J., Hong, S., Lee, H., Lee, H. Enhancement of paclitaxel production by temperature shift in suspension culture of Taxus chinensis. Enzyme Microb. Technol. 2000, 27, 593-598.
37. Wang, H.Q., Yu, J.T., Zhong, J.J. Significant improvement of taxane production in suspension cultures of Taxus chinensis by sucrose feeding strategy. Proc. Biochem. 1999, 35, 479-483.
38. Wang, C., Wu, J., Mei, X. Enhancement of Taxol production and excretion in Taxus chinensis cell culture by fungal elicitation and medium renewal. Appl. Microbiol. Biotechnol. 2001, 55, 404-410.
39. 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.
40. Wickremesinhe, E.R.M., Arteca, R.N. Taxus callus cultures: Initiation, growth optimization, characterization and taxol production. Plant Cell Tiss. Organ Cult. 1993, 35, 181-193.
41. Wickremesinhe, E.R.M., Arteca, R.N. Taxus cell suspension cultures: optimizing growth and production of taxol. J. Plant Physiol. 1994, 144, 183-188.
42. Yukimune, 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.
43. Dewick, P.M. The mevalonate and deoxyxylulose phosphate pathways: terpenoids and steroids. In: Medicinal Natural Products: A Biosynthetic Approach, 2nd edition. John Wiley & Sons Ltd, Chichester, UK, 2002, pp. 167-289.
44. Lloyd, G., McCown, B. Commercially feasible micropropagation of mountain laurel, Kalmia latifolia, by the use of shoot-tip culture. Int. Plant Prop. Soc. Proc. 1981, 30, 421-427.
45. Gamborg, O.L., Miller, R.A., Ojima, K., Nutrient requirements of suspension cultures of soybean root cells. Exp. Cell Res. 1968, 50, 151-158.
46. Hezari, M., Ketchum, R.E., Gibson, D.M., Croteau, R. Taxol production and taxadiene synthase activity in Taxus canadensis cell suspension cultures. Arch. Biochem. Biophys. 1997, 337, 185-190.
47. Tabata, H. Paclitaxel production by plantcell-culture technology. Adv. Biochem. Eng./Biotechnol. 2004, 87, 1-23.
48. Tabata, H., Higashi, Y. Taxol production by plant cell culture technology. Catalysts Catalysis 2001, 43, 207-211 (in Japanese).
49. 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. Proc. Natl. Acad. Sci. USA 1996, 93, 6431-6436.
50. Zheng, Q.P., Yu, L.J., Liu, Z., Li, M.Y., Xiang, F., Yang, Q. Cloning and analysis of cDNA encoding key enzyme gene (dxr) of the non-MVA pathway in Taxus chinensis cells. Sheng Wu Gong Cheng Xue Bao 2004, 20, 548-553 (in Chinese).
51. Jennewein, S., Wildung, M.R., Chau, M., Walker, K., Croteau, R. Random sequencing of an induced Taxus cell cDNA library for identification of clones involved in Taxol biosynthesis. Proc. Natl. Acad. Sci. USA 2004, 101, 9149-9154.
52. Hefner, J., Ketchum, R.E., Croteau, R. Cloning and functional expression of a cDNA encoding geranylgeranyl diphosphate synthase from Taxus canadensis and assessment of the role of this prenyltransferase in cells induced for taxol production. Arch. Biochem. Biophys. 1998, 360, 62-74.
53. Okada, K., Saito, T., Nakagawa, T., Kawamukai, M., Kamiya, Y. Five geranylgeranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis. Plant Physiol. 2000, 122, 1045-1056.
54. 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.
55. Lesburg, C.A., Zhai, G., Cane, D.E., Christianson, D.W. Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science 1997, 277, 1820-1824.
56. Tarshis, L.C., Yan, M., Poulter, C.D., Sacchettini, J.C. Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution. Biochemistry 1994, 33, 10871-10877.
57. Li, S.H., Zhan, H.J., Yao, P., Niu, X.M., Xiang, W., Sun, H.D. Non-taxane compounds from the bark of Taxus yunnanensis. J. Asian Nat. Prod. Res. 2002, 4, 147-154.
58. Monacelli, B., Pasqua, G., Botta, B., Vinciguerra, V., Gacs-Baitz, E., Monache, G.D. Abietane diterpenoids from callus cultures of Taxus baccata. Planta Med. 2002, 68, 764-766.
59. Bai, J., Kitabatake, M., Toyoizumi, K., Fu, L., Zhang, S., Dai, J., Sakai, J., Hirose, K., Yamori, T., Tomida, A., Tsuruo, T., Ando, M. Production of biologically active taxoids by a callus culture of Taxus cuspidata. J. Nat. Prod. 2004, 67, 58-63.
60. Jennewein, S., Long, R.M., Williams, R.M., Croteau, R. Cytochrome p450 taxadiene 5alpha-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygenation step of taxol biosynthesis. Chem. Biol. 2004, 11, 379-387.
61. Schoendorf, A., Rithner, C.D., Williams, R.M., Croteau, R.B. Molecular cloning of a cytochrome P450 taxane 10betahydroxylase cDNA from Taxus and functional expression in yeast. Proc. Natl. Acad. Sci. USA 2001, 98, 1501-1506.
62. Chau, M., Croteau, R. Molecular cloning and characterization of a cytochrome P450 taxoid 2alpha-hydroxylase involved in Taxol biosynthesis. Arch. Biochem. Biophys. 2004, 427, 48-57.
63. Jennewein, S., Rithner, C.D., Williams, R.M., Croteau, R.B. Taxol biosynthesis: taxane 13alpha-hydroxylase is a cytochrome P450-dependent monooxygenase. Proc. Natl. Acad. Sci. USA 2001, 98, 13595-13600.
64. Chau, M., Jennewein, S., Walker, K., Croteau, R. Taxol biosynthesis: Molecular cloning and characterization of a cytochrome P450 taxoid 7betahydroxylase. Chem. Biol. 2004, 11, 663-672.
65. Walker, K., Schoendorf, A., Croteau, R. Molecular cloning of a taxa-4(20),11(12)-dien-5alpha-ol-O-acetyl transferase cDNA from Taxus and functional expression in Escherichia coli. Arch. Biochem. Biophys. 2000, 374, 371-380.
66. 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.
67. Walker, K., Croteau, R. Taxol biosynthesis: molecular cloning of a benzoyl-CoA:taxane 2alpha-O-benzoyltransferase cDNA from Taxus and functional expression in Escherichia coli. Proc. Natl. Acad. Sci. USA 2000, 97, 13 591-13 596.
68. Jennewein, S., Rithner, C.D., Williams, R.M., Croteau, R. Taxoid metabolism: Taxoid 14â-hydroxylase is a cytochrome P450-dependent monooxygenase. Arch. Biochem. Biophys. 2003, 413, 262-270.
69. Walker, K.D., Klettke, K., Akiyama, T., Croteau, R. Cloning, heterologous expression, and characterization of a phenylalanine aminomutase involved in Taxol biosynthesis. J. Biol. Chem. 2004, 279, 53947-53954.
70. Long, R.M., Croteau, R. Preliminary assessment of the C13-side chain 2'-hydroxylase involved in Taxol biosynthesis. Biochem. Biophys. Res. Commun. 2005, 338, 410-417.
71. Walker, K., Fujisaki, S., Long, R., Croteau, R. Molecular cloning and heterologous expression of the C-13 phenylpropanoid side chain-CoA acyltransferase that functions in Taxol biosynthesis. Proc. Natl. Acad. Sci. USA 2002, 99, 12715-12720.
72. Walker, K., Long, R., Croteau, R. The final acylation step in taxol biosynthesis: cloning of the taxoid C13-side-chain Nbenzoyltransferase from Taxus. Proc. Natl. Acad. Sci. USA 2002, 99, 9166-9171.
73. Mukherjee, S., Ghosh, B., Jha, S. Establishment of forskolin yielding transformed cell suspension cultures of Coleus forskohlii as controlled by different factors. J. Biotechnol. 2000, 76, 73-81.
74. Chen, H., Yuan, J.P., Chen, F., Zhang, Y.L., Song, J.Y. Tanshinone production in Ti-transformed Salvia miltiorrhiza cell suspension cultures. J. Biotechnol. 1997, 58, 147-156.
75. Bauer, N., Leljak-Levanic, D., Jelaska, S. Rosmarinic acid synthesis in transformed callus culture of Coleus blumei benth. Z. Naturforsch. C. 2004, 59, 554-560.
76. 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.
77. Yoshimatsu, K., Shimomura, K. Isoquinoline alkaloid production by transformed cultures of Papaver somniferum. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku 2001, 119, 52-56.
78. Shu, W., Yoshimatsu, K., Yamaguchi, H., Shimomura, K. High production of ginsenosides by transformed root cultures of Panax ginseng: effect of basal medium and Agrobacterium rhizogenes strains. Kokuritsu Iyakuhin Shokuhin Eisei Kenkyusho Hokoku 1999, 117, 148-154.
79. 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.
80. Matsubayashi, Y., Sakagami, Y. Phytosulfokine, sulfated peptides that induce the proliferation of single mesophyll cells of Asparagus officinalis L. Proc. Natl. Acad. Sci. USA 1996, 93, 7623-7627.
81. Matsubayashi, Y., Hanai, H., Hara, O., Sakagami, Y. Active fragments and analogs of the plant growth factor, phytosulfokine: structure-activity relationships. Biochem. Biophys. Res. Commun. 1996, 225, 209-214.
82. Yang, H., Matsubayashi, Y., Nakamura, K., Sakagami, Y. Oryza sativa PSK gene encodes a precursor of phytosulfokinealpha, a sulfated peptide growth factor found in plants. Proc. Natl. Acad. Sci. USA 1999, 96, 13560-13565.
83. Matsubayashi, Y., Takagi, L., Sakagami, Y. Phytosulfokine-alpha, a sulfated pentapeptide, stimulates the proliferation of rice cells by means of specific highand low-affinity binding sites. Proc. Natl. Acad. Sci. USA 1997, 94, 13357-13362.
84. Tabata, H., Hara, Y. Prevention of browning of plant cultured cell. JP patent 11/196863, 1999.
85. Kwon, T.H., Seo, J.E., Kim, J., Lee, J.H., Jang, Y.S., Yang, M.S. Expression and secretion of the heterodimeric protein interleukin-12 in plant cell suspension culture. Biotechnol. Bioeng. 2003, 81, 870-875.
86. Fischer, R., Liao, Y.C., Drossard, J. Affinity-purification of a TMV-specific recombinant full-size antibody from a transgenic tobacco suspension culture. J. Immunol. Methods 1999, 226, 1-10.
87. Gomord, V., Faye, L. Posttranslational modification of therapeutic proteins in plants. Curr. Opin. Plant Biol. 2004, 7, 171-181.