Microbial paclitaxel: Advances and perspectives

Journal of Antibiotics

Volumn 63, Issue 8, 2010, Pages 460-467

  Flores Bustamante, Zoila R ^a   Rivera Ordũa, Flor N ^a   Martínez Cárdenas, Anahí ^a   Flores Cotera, Luis B ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

bacteria; fungi; genes; HPLC MS; taxol

Indexed keywords

PACLITAXEL; TAXANE DERIVATIVE;

BACTERIUM; BIOSYNTHESIS; EXERCISE; FERMENTATION; FUNGUS; GENOME; MICROORGANISM; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; REVIEW;

AMINO ACID SEQUENCE; ANTINEOPLASTIC AGENTS; BACTERIA; BIOMEDICAL RESEARCH; BIOTECHNOLOGY; FUNGI; HUMANS; MOLECULAR SEQUENCE DATA; PACLITAXEL;

BACTERIA (MICROORGANISMS); FUNGI;

EID: 77956248163     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.83     Document Type: Review

References (88)

1. Strobel, G. A., Hess, W. M., Ford, E., Sidhu, R. S. & Yang, X. Taxol from fungal endophytes and the issue of biodiversity. J. Ind. Microbiol. Biotechnol. 17, 417-423 (1996b).
2. Suffness, M. Overview of paclitaxel research: progress on many fronts. Taxane anti-cancer agents. ACS Symp. Ser. 583, 1-17 (1995).
3. Nicolaou, K. C. et al. Total synthesis of taxol. Nature 367, 630-634 (1994).
4. Holton, R. A. et al. First total synthesis of taxol. J. Am. Chem. Soc. 116, 1597-1598 (1994).
5. Baloglu, E. & Kingston, D. G. I. The taxane diterpenoids. J. Nat. Prod. 62, 1448-1472 (1999).
6. Patel, R. Tour de paclitaxel. Biocatalysis for semisynthesis. Annu. Rev. Microbiol. 52, 361-395 (1998).
7. Frense, D. Mini-review, taxanes: perspectives for biotechnological production. Appl. Microbiol. Biotechnol. 73, 1233-1240 (2006).
8. Cragg, G. M. & Snader, K. M. Taxol: the supply issue. Cancer Cells 3, 233-235 (1991).
9. Ketchum, R. E. B., Gibson, D. M., Croteau, R. B. & Shuler, M. L. The kinetics of taxoid accumulation in cell suspension cultures of Ta x u s following elicitation with methyl jasmonate. Biotechnol. Bioeng. 62, 97-105 (1999).
10. Zhong, J. J. Plant cell culture for production of paclitaxel and other taxanes. Review. J. Biosci. Bioeng. 94, 591-599 (2002).
11. Wink, M. et al. Sustainable bioproduction of phytochemicals by plant in vitro cultures: anticancer agents. Gen. Res. 3, 90-100 (2005).
12. Nguyen, T., Eshraghi, J., Gonyea, G., Ream, R. & Smith, R. Studies on factors influencing stability and recovery of paclitaxel from suspension media and cultures of Taxus cuspidata cv. densiformis by high-performance liquid chromatography. J. Chromatogra. 911, 55-61 (2001).
13. Stierle, A., Strobel, G. A. & Stierle, D. Taxol and taxane production by Taxomyces andreanae, an endophytic fungus of pacific yew. Science 260, 214-216 (1993).
14. Strobel, G. A., Stierle, A., Stierle, D. & Hess, W. M. Taxomyces andreanae a proposed new taxon for a bulbilliferous hyphomycete associated with Pacific yew. Mycotaxon 47, 71-80 (1993).
15. Stierle, A., Strobel, G., Stierle, D., Grothaus, P. & Bignami, G. The search for a taxol-producing microorgansim among the endophytic fungi of the pacific yew, Taxus brevifolia. J. Nat. Prod. LLoydia 58, 1315-1324 (1995).
16. Strobel, G. Rainforest endophytes and bioactive products. Crit. Rev. Biotechnol. 22, 315-333 (2002).
17. Strobel, G. et al. Taxol from Pestalotiopsis microspora, an endophytic fungus of Ta x u s wallichiana. Microbiology 142, 435-440 (1996a).
18. Shrestha, K., Strobel, G. A., Shrivastava, S. P. & Gewali, M. B. Evidence for paclitaxel from tree new endophytic fungi of Himalayan yew of Nepal. Planta Med. 67, 374-376 (2001).
19. Bashyal, B., Li, J. Y., Strobel, G. A. & Hess, W. M. Seimatoantlerium nepalense, an endophytic taxol producing coelomycete from Himalayan yew (Taxus wallachiana). Mycotaxon. 72, 33-42 (1999).
20. Noh, M. J. et al. Isolation of a novel microorganism, Pestalotia heterocornis, producing paclitaxel. Biotechnol. Bioeng. 64, 620-623 (1999).
21. Caruso, M. et al. Isolation of endophytic fungi and actinomycetes taxane producers. Annals Microbiol. 50, 3-13 (2000b).
22. Wang, J. F. et al. Taxol from Tubercularia sp. strain TF5, an endophytic fungus of Ta x u s mairei. FEMS Microbiol. Lett. 193, 249-253 (2000).
23. Wan, B., Li, A. M. & Wang, X. L. Separation of a fungus producing taxol. Sci. China Ser C. 44, 156-160 (2001).
24. Zhou, D. et al. Study on the mutagenesis of protoplasts from taxol-producing fungus Nodulisporium sylviforme. The J. Am. Sci. 1, 55-62 (2005).
25. Zhao, K., Zhou, D. P., Ping, W. X. & Jingping, G. Study on the preparation and regeneration of protoplast from taxol-producing fungus Nodulisporium sylviforme. Nat. Sci. 2, 52-59 (2004).
26. Deng, B. W., Liu, K. H., Chen, W. Q., Ding, X. W. & Xie, X. C. Fusarium solani, Tax-3, a new endophytic taxol-producing fungus from Ta xu s c h i nen s i s. World J. Microbiol. Biotechnol. 25, 139-143 (2009).
27. Zhou, X. et al. Screening of taxol-producing endophytic fungi from Taxuschinensis var. mairei. Appl. Biochem. Microbiol. 43, 439-443 (2007).
28. Miao, Z., Wang, Y., Yu, X., Guo, A. & Tang, K. New endophytic taxane production fungus from Ta x u s c h i n e n s i. Appl. Biochem. Microbiol. 45, 81-86 (2009).
29. Kumaran, R. S. & Hur, B. K. Screening of species of the endophytic fungus Phomopsis for the production of the anticancer drug taxol. Biotechnol. Appl. Biochem. 54, 21-30 (2009).
30. Zhang, P., Zhou, P. P., Jiang, C., Yu, H. & Yu, L. J. Screening of taxol-producing fungi based on PCR amplification from Ta x u s. Biotechnol. Lett. 30, 2119-2123 (2008).
31. Zhang, P., Zhou, P. P. & Yu, L. J. An endophytic Taxol-producing fungus from Ta x u s x media, Cladosporium cladosporioides MD2. Curr. Microbiol. 59, 227-232 (2009a).
32. Zhang, P., Zhou, P. P. & Yu, L. J. An edophytic Taxol-producing fungus from Ta x u s x media, Aspergillus candidus MD3. FEMS Microbiol. Lett. 293, 55-159 (2009b).
33. Li, J. Y., Strobel, G., Sidhu, R., Hess, W. M. & Ford, E. J. Endophytic taxol producing fungi from bald cypress Taxodium distichum. Microbiology 142, 2223-2226 (1996).
34. Strobel, G. A. et al. Pestalotiopsis guepinii, a taxol producing endophyte of the Wollemi Pine, Wollemia nobilis. Aust. J. Bot. 4586, 1073-1082 (1997).
35. Hoffman, A. et al. Bioprospecting for taxol in angiosperm plant extracts\using high performance liquid chromatography thermospray mass spectroscopy to detect the anticancer agent and its related metabolites in Filbert trees. Spectroscopy 13, 22-32 (1998).
36. Li, J. Y. et al. The induction of taxol production in the endophytic fungus Periconia sp. from Torreya grandifolia. J. Ind. Microbiol. Biotechnol. 20, 259-264 (1998b).
37. Strobel, G. A. et al. Seimatoantlerium tepuiense gen. nov., a unique epiphytic fungus producing taxol from the Venezuelan-Guayana. System Appl. Microbiol. 22, 426-433 (1999).
38. Strobel, G. et al. Stegolerium kukenani gen, et sp nov., an endophytic taxol producing fungus from the Roraima and Kukenan tepuis of Venezuela. Mycotaxon 78, 353-361 (2001).
39. Gangadevi, V. & Muthumary, J. Taxol production by Pestalotiopsis terminaliae, an endophytic fungus of Terminalia arjuna (arjun tree). Biotech. Appl. Biochem. 52, 9-15 (2009b).
40. Gangadevi, V. & Muthumary, J. Taxol, an anticancer drug produced by an endophytic fungus Bartalinia robillardoides Tassi, isolated from a medicinal plant, Aegle marmelos Correa ex Roxb. World J. Microbiol. Biotechnol. 24, 717-724 (2008).
41. Kumaran, R. S., Muthumary, J. & Hur, B. K. Isolation and identification of an anticancer drug, taxol from Phyllosticta tabernaemontanae, a leaf spot fungus of an angiosperm, Wrightia tinctoria. J. Microbiol. 47, 40-49 (2009a).
42. Kumaran, R. S., Muthumary, J. & Hur, B. K. Production of Taxol from Phyllosticta spinarum, an endophytic fungus of Cupressus sp. Eng. Life Sci. 8, 438-446 (2008b).
43. Kumaran, R. S., Muthumary, J. & Hur, B. K. Taxol from Phyllosticta citricarpa, a leaf spot fungus of the angiosperm Citrus medica. J. Biosci. Bioeng. 106, 103-106 (2008c).
44. Kumaran, R., Muthumary, J., Kim, E. K. & Hur, B. K. Production of taxol from Phyllosticta dioscoreae, a leaf spot fungus isolated from Hibiscus rosa-sinensis. Biotechnol. Bioprocess Eng. 14, 76-83 (2009b).
45. Page, M. & Landry, N. Bacterial mass production of taxanes with Erwinia. U.S. 5,561,055 (1996).
46. Page, M. et al. Bacterial mass production of taxanes and paclitaxel. U.S. 6,030,818 (2000).
47. Caruso, M. et al. Studies on a strain of Kitasatospora sp. paclitaxel producer. Annals. Microbiol. 50, 89-102 (2000a).
48. Li, J. Y., Sidhu, R. S., Bollon, A. & Strobel, G. A. Stimulation of taxol production in liquid cultures of Pestalotiopsis microspora. Mycol. Res. 102, 461-464 (1998a).
49. Hezari, M. & Croteau, R. Taxol biosynthesis: an update. Planta Med. 63, 291-295 (1997).
50. Jennewein, S. & Croteau, R. Taxol biosynthesis: molecular genetics, and biotechno-logical applications. Appl. Microbiol. Biotechnol. 57, 13-19 (2001).
51. Walker, K. & Croteau, R. Taxol biosynthetic genes. Phytochemistry 58, 1-7 (2001).
52. Hezari, M., Lewis, N. G. & Croteau, R. Purification and characterization of taxa-4(5),11(12)-diene synthase from Pacific yew (Taxus brevifolia) that catalyzes the first committed step of taxol biosynthesis. Arch. Biochem. Biophys. 322, 437-444 (1995).
53. DeJong, J. M. et al. Genetic engineering of Taxol biosynthetic genes in Saccharomyces cerevisiae. Biotechnol. Bioeng. 93, 212-224 (2006).
54. Walker, K., Long, R. & Croteau, R. The final acylation step in Taxol biosynthesis: cloning of the taxoid C13-side-chain N-benzoyltransferase from Ta x u s. Proc. Natl Acad. Sci. (USA) 99, 9166-9171 (2001).
55. Croteau, R. B., Ketchum, R. E. B., Long, R., Kaspera, R. & Wildung, M. Taxol biosynthesis and molecular genetics. Phytochem. Rev. 5, 75-97 (2006).
56. 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) 98, 13595-13600 (2001).
57. Schoendorf, A., Rithner, C. D., Williams, R. M. & Croteau, R. B. Molecular cloning of a cytochrome P450 taxane 10 beta-hydroxylase cDNA from Tax u s and functional expression in yeast. Proc. Natl Acad. Sci. USA 98, 1501-1506 (2001).
58. Staniek, A., Woerdenbag, H. J. & Kayser, O. Taxomyces andreanae: a presumed paclitaxel producer demystified? Planta Med. 75, 1561-1566 (2009).
59. Zhao, K. et al. Aspergillus niger var. taxi, a new species variant of taxol-producing fungus isolated from Ta x u s c u s p i d a t a in China. J. Appl. Microbiol. 107, 1202-1207 (2009).
60. Withers, S. T. & Keasling, J. D. Biosynthesis and engineering of isoprenoid small molecules. Appl. Microbiol. Biotechnol. 73, 980-990 (2007).
61. 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. 271, 9201-9204 (1996).
62. Walker, K., Schoendorf, A. & Croteau, R. Molecular cloning of a taxa-4(20), 11(12)-dien-5 alpha-ol-O-acetyl transferase cDNA from Ta x u s and functional expression in Escherichia coli. Arch. Biochem. Biophys. 374, 371-380 (2000).
63. 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) 99, 12715-12720 (2002).
64. Jennewein, S., Wildung, M. R., Chau, M., Walker, K. & Croteau, R. Random sequencing of an induced Ta x u s cell cDNA library for identification of clones involved in taxol biosynthesis. Proc. Natl Acad. Sci. (USA) 101, 9149-9154 (2004a).
65. Jennewein, S., Long, R. M., Williams, R. M. & Croteau, R. Cytochrome P450 taxadiene 5a-hydroxylase, a mechanistically unusual monooxygenase catalyzing the first oxygena-tion step of taxol biosynthesis. Chem. Biol. 11, 379-387 (2004b).
66. Walker, K. & Croteau, R. Molecular cloning of a 10-deacetylbaccatin III-10-O-acetyl transferase cDNA from Ta x u s and functional expression in Escherichia coli. Proc. Natl Acad. Sci. (USA) 97, 583-587 (2000a).
67. Walker, K. & Croteau, R. Taxol biosynthesis: molecular cloning of a benzoyl-CoA: taxane 2 alpha-O-benzoyltransferase cDNA from Ta x u s and functional expression in Escher-ichia coli. Proc. Natl Acad. Sci. (USA) 97, 13591-13596 (2000b).
68. Williams, D. C. et al. Heterologous expression and characterization of a 'pseudomature' form of taxadiene synthase involved in paclitaxel (Taxol) biosynthesis and evaluation of a potential intermediate and inhibitors of the multistep diterpene cyclization reaction. Arch. Biochem. Biophys. 379, 137-146 (2000).
69. Hahn, F. M. & Poulter, C. D. Isolation of Schizosaccharomyces pombe isopentenyl diphosphate isomerase cDNA clones by complementation and synthesis of the enzyme in Escherichia coli. J. Biol. Chem. 270, 11298-11303 (1995).
70. Hefner, J., Ketchum, R. E. B. & 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. 360, 62-74 (1998).
71. 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. 13, 90-96 (1998).
72. Huang, Q. L., Roessner, C. A., Croteau, R. & Scott, A. I. Engineering Escherichia coli for the synthesis of taxadiene, a key intermediate in the biosynthesis of taxol. Bioorganic Med. Chem. 9, 2237-2242 (2001).
73. Engels, B., Dahm, P. & Jennewein, S. Metabolic engineering of taxadiene biosynthesis in yeast as a first step towards Taxol (paclitaxel) production. Metabolic Eng. 10, 201-206 (2008).
74. Muralidhar, R. V. & Panda, T. Fungal protoplast fusion\a revisit. Bioproc. Biosyt. Eng. 22, 429-431 (2000).
75. Zhao, K., Ping, W. X. Ma, X. Liu, J. & Zhou, D. P. Breeding of high-yield strain of taxol by mutagenesis of protoplast and primary discussion of genetic differences between mutants and their parent strain. Acta. Microbiol. Sin. 45, 355-358 (2005).
76. Zhao, K. et al. Screening and breeding of high taxol producing fungi by genome suffling. Sci. China Ser. C-Life Sci. 5, 222-231 (2008).
77. Zhou, D. P., Sun, J. Q., Yu, H. Y., Zheng, X. Q. & Ping, W. X. Nodulisporium, a genus new to China. Mycosystema 20, 277-278 (2001).
78. Williams, R. B., Henrikson, J. C., Hoover, A. R., Lee, A. E. & Cichewicz, R. H. Epigenetic remodeling of the fungal secondary metabolome. Org. Biomol. Chem. 6, 1895-1897 (2008).
79. Grothaus, P. G., Raybould, T. J. G., Bignami, G. S., Lazo, C. B. & Byrnes, J. B. An enzyme immunosassay for the determination of taxol and taxanes in Ta x u s sp. tissues and human plasma. J. Immunol. Meth. 158, 5-15 (1993).
80. Theodoridis, G. & Verpoorte, R. Taxol analysis by high performance liquid chromato-graphy: a review. Phytochem. Anal. 7, 169-184 (1996).
81. Li, S. et al. Determination of paclitaxel and other six taxoids in Ta x u s species by high-performance liquid chromatography-tandem mass spectrometry. J. Pharma. Biomed. Anal. 49, 81-89 (2009).
82. n, the top-down/bottom-up approach, and HPLC ESI capillary-skimmer CID FTMS. Anal. Chem. 75, 2730-2739 (2003).
83. Guo, B. H. et al. An endophytic taxol-producing fungus BT2 isolated from Ta x u s chiniensis var. mairei. African J. Biotechnol. 5, 875-877 (2006).
84. Xu, F., Tao, W., Cheng, L. & Guo, L. Strain improvement and optimization of the media of taxol-producing fungus Fusarium maire. Biochem. Eng. J. 31, 67-73 (2006).
85. Chi, Y., Zhao, D. L. & Zhou, D. P. Identification of taxol biosynthesis stage-enriched transcripts in Nodulisporium sylviforme, using suppression subtractive hybridization. World J. Microbiol. Biotechnol. 24, 2601-2605 (2008).
86. Kumaran, R. S., Muthumary, J. & Hur, B. K. Isolation and identification of taxol, an anticancer drug from Phyllosticta melochiae Yates, an endophytic fungus of Melochia corchorifolia L. Food Sci. Biotechnol. 17, 1246-1253 (2008a).
87. Gangadevi, V. & Muthumary, J. A novel endophytic Taxol-producing fungus Chaetomella raphigera isolated from a medicinal plant, Terminalia arjuna. Appl. Biochem. Biotech-nol. 158, 675-684 (2009a).
88. Larkin, M. A. et al. Clustal W and Clustal X version 2.0. Bioinformatics 23, 2947-2948 (2007).