The role of biotechnology in the production of the anticancer compound podophyllotoxin

Methods in Molecular Biology

Volumn 547, Issue , 2009, Pages 387-402

  Lata, Hemant ^a   Mizuno, Cassia S ^a   Moraes, Rita M ^a  

^a NONE

Author keywords

Lignan; Medicinal crop; Podophyllum; Secondary compounds

Indexed keywords

ANTINEOPLASTIC AGENT; PODOPHYLLOTOXIN;

ACCLIMATIZATION; ARBUSCULAR MYCORRHIZA; BIOTECHNOLOGICAL PRODUCTION; CONSERVATIONAL SEED BANK; DOMESTICATION; ENCAPSULATION; GENOTYPE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NATURAL POPULATION; NONHUMAN; PHYTOCHEMISTRY; PODOPHYLLUM; PODOPHYLLUM PELTATUM; REGULATORY MECHANISM; ARTICLE; BIOSYNTHESIS; BIOTECHNOLOGY; METABOLISM;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOTECHNOLOGY; PODOPHYLLOTOXIN; PODOPHYLLUM;

EID: 67650221636     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-60327-287-2_31     Document Type: Chapter

References (79)

1. Fukuda, Y., Namiki, M. and Osawa, T. (1985). Studies on anti-oxidative substances in sesame seed. Agric. Biol. Chem. 49, 301-306.
2. Figgitt, D.P., Denever, S.P., Dewick, P.M., Jackson, D.E. and Willians, P. (1989). Topoisomerase II: a potential target for novel antifungal agents. Biochem. Biophys. Res. Commun. 160, 257-262.
3. Bedir, E., Khan, I. and Moraes R.M. (2002). Bioprospecting for podophyllotoxin. In: Janick, J., Whipkey, A. (Eds.) Trends in New Crops and New Uses, ASHS Press, Alexandria, pp. 545-549.
4. Loike, J.D. and Horwitz, S.B. (1976). Effects of podophyllotoxin and VP 16-213 on microtubule assembly in vitro and nucleoside transport in HeLa cells. Biochemistry 15, 5435-5442.
5. Loike, J.D., Brewer, C.F., Sternlicht, H., Gensler, W.J. and Horwitz, S.B. (1978). Structure-activity study of the inhibition of microtubules assembly in vitro by podophyllotoxin and its congeners. Cancer Res. 38, 2688-2693.
6. Stahelin, H.F. and Wartburg, A.V. Von (1991). The chemical and biological route from podophyllotoxin glucoside to etoposide. Cancer Res. 51, 5-15.
7. Canel, C., Moraes, R.M., Dayan, F.E. and Ferreira, D. (2000). Molecules of interest "podophyllotoxin". Phytochemistry 54, 115-120.
8. Liu, Y.Q., Yang, L. and Tian, X. (2007). Podophyllotoxin: current perspectives. Curr. Bioact. Compd. 3, 37-66.
9. Kaplan, I.W. (1942). Condylomata acuminatum. New Orleans Med. Surg. J. 94, 388.
10. King, L.S. and Sullivan, M. (1946). The similarity of the effect of podophyllin and colchicine and their use in the treatment of condylomata acuminate. Science 104, 244-245.
11. Loike, J.D. and Horwitz, S.B. (1976). Effect of VP 16-213 on the intracellular degradation of DNA in HeLa cells. Biochemistry 15, 5443-5448.
12. Horwtiz, S.B. and Loike, J.D. (1977). A comparison of the mechanism of action of VP 16-213 and podophyllotoxin. Lloydia 40, 82-89.
13. Minocha, A. and Long, B.H. (1984). Inhibition of the DNA catenation activity of type II topoisomerase by VP 16-213, VM-26. Biochem. Biophys. Res. Commun. 122, 165-170.
14. Hartmann, J.T. and Lipp, H.P. (2006). Camptothecin and podophyllotoxin derivatives. Drug Saf. 29, 209-230.
15. Hosoi, H., Lehara, T., Tsuchiya, K., Misawa, A., Miyaji, M., Yagyu, S., Koizumi, M., Nishimura, T., Tokiwa, K. and Iwai, N. (2007). Continuous remission in an infant with chest wall malignant rhabdoid tumor after relapse. J. Pediatr. Surg. 42, e9-e12.
16. Schacter, L. (1996). Etoposide phosphate: what, why, where, and how? Semin. Oncol. 6(Suppl 13), 1-7.
17. Gordaliza, M., Garcia, P.A., Miguel del Corral, J.M., Castro, M.A. and Gomez-Zurita, M.A. (2004). Podophyllotoxin: distribution, source, application and new cytotoxic derivatives. Toxicon 44, 441-459.
18. Ekimoto, H., Okamoto, K. and Maruyama, S. (1992). Preclinical characterization of NK611, a novel water-soluble etoposide analog. Ann. Oncol. 3 (Suppl 1), 98.
19. Lee, K.H. (1999). Novel antitumor agents from higher plants. Med. Res. Rev. 19(6), 569-596.
20. Huang, T.S., Lee, C.C., Chao, Y., Shu, C.H., Chen, L.T., Chen, L.L., Chen, M.H., Yuan, C.C. and Whang-Peng, J. (1999). A novel podophyllotoxin-derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells. Pharm. Res. 16(7), 997-1002.
21. Terada, T., Fujimoto, K., Nomura, M.A., Yamashita, J., Wierzba, K., Yamazaki, R., Shibata, J., Sugimoto, Y. and Yamada, Y. (1993). Antitumor agents. 3. Synthesis and biological activity of 4 β-alkyl derivatives containing hydroxy, amino, and amido groups of 4 ¢-O-demethyl-4-desoxypodophyllotoxin as antitumor agents. J. Med. Chem. 36(12), 1689-1699.
22. Yoshida, M., Kobunai, T., Aoyagi, K., Saito, H., Utsugi, T., Wierzba, K. and Yamada, Y. (2000). Specific distribution of TOP-53 to the lung and lung-localized tumor is determined by its interaction with phospholipids. Clin. Cancer Res. 6 (11), 4396-4401.
23. Utsugi, T., Shibata, H., Kumio, S., Aoyagi, K., Wierzba, K., Kobunai, T., Terada, T., Oh-hara, T., Tsuruo, T. and Yamada, Y. (1996). Antitumor activity of a novel podophyllotoxin derivative (TOP-53) against lung cancer and lung metastatic cancer. Cancer Res. 56(12), 2809-2814.
24. Kruczynski, A., Etievant, C., Perrin, D., Imbert, T., Colpaert, F. and Hill, B.T. (2000). Preclinical antitumour activity of F 11782, a novel dual catalytic inhibitor of topoisomerases. Br. J. Cancer 83(11), 1516-1524.
25. Jensen, L.H., Renodon-Corniere, A., Nitiss, K.C., Hill, B.T., Nitiss, J.L., Jensen, P.B. and Sehested, M. (2003). A dual mechanism of action of the anticancer agent F 11782 on human topoisomerase II. Biochem. Pharm. 66 (4), 623-631.
26. Chen, S.W., Wang, Y.H., Jin, Y., Tian, X., Zeng, Y.T., Lou, D.Q. and Tu, Y.Q. (2007). Synthesis and anti-HIV 1 activities of novel podophyllotoxin derivatives. Bioorg. Med. Chem. Lett. 17, 2091-2095.
27. Pugh, N., Khan, I., Moraes, R.M. and Pasco, D. (2001). Podophyllotoxin lignans enhance IL-1 but suppress TNF-a mRNA expression in LPS-treated monocytes. Immunopharmacol. Immunotoxicol. 23, 83-95.
28. Leander, K. and Rosen, B. (1988). Medicinal use for podophyllotoxin. US Patent 4 (788), 216.
29. Bohlin, L. and Rosen, B. (1996). Podophyllotoxin derivatives: drug discovery and development. Drug Discover. Today 1, 343-351.
30. Di, X., Liu, Y., Liu, Y., Yu, X., Xiao, H., Tian, X. and Gao, R. (2007). Synthesis and insectidal activities of pyridine ring derivatives of podophyllotoxin. Pestic. Biochem. Physiol. 89, 81-87.
31. Oliva, A., Moraes, R.M., Watson, S.B., Duke, S.O. and Dayan, F.E. (2002). Aryltetralin lignans inhibit plant growth by affecting the formation of mitotic microtubular organizing centers. Pestic. Biochem. Physiol. 72, 45-54.
32. Bush, E.J. and Jones, D.W. (1995). Asymmetric total synthesis of (-)-podophyllotoxin. J. Chem. Soc. Perkin Trans. 1, 151-155.
33. Hartwel, J.L. and Shear, M.J. (1947). Chemotherapy of cancer: class of compound under investigation and the active components of podophyllin Cancer Res. 7, 716.
34. Fransen, M.C.R. and Walton, M.J. (1999). Biotransformations. In: Walton, M.J., Brawn, D.E. (Eds.), Chemicals from Plants, Perspectives on Plant Secondary Products, Imperial College Press, London, pp. 277-325.
35. Gordaliza, M., Castro, M.A, Miguel del Corral, J.M. and San Feliciano, A. (2000). Antitumor properties of podophyllotoxin and related compounds. Curr. Pharm. Des. 6, 1811-1839.
36. Petersen, M. and Alfermann, A.W. (2001). The production of cytotoxic lignans by plant cell cultures. Appl. Microbiol. Biotechnol. 55, 135-142.
37. Puricelli, L., Innocenti, G., Piacente, S., Caniato, R., Filippini, R. and Capelletti, E.M. (2002). Production of lignans by Haplophyllum patavinum in vivo and in vitro. Heterocycles 56, 607-612.
38. Meijer, W. (1974). Podophyllum peltatum-mayapple a potential new cash-crop plant of Eastern North America. Econ. Bot. 28, 68-72.
39. Jackson, D.E. and Dewick, P.M. (1984). Aryltetralin lignans from Podophyllum hexandrum and Podophyllum peltatum. Phytochemistry 23(5), 1147-1152.
40. Bhadula, S.K., Singh, A., Lata, H., Kuniyal, C.P. and Purohit, A.N. (1996). Genetic resources of Podophyllum hexandrum Royle, an endangered medicinal species from Garhwal Himalaya, India. Int. Plant. Gen. Resour. Newslett. 106, 26-29.
41. Foster, S. (1993). Medicinal plant conservation and genetic resources: examples from the temperate northern hemisphere. Acta Hortic. 330, 67-73.
42. Nadeem, M., Palni, L.M.S., Purohit, A.N., Pandey, H. and Nandi, S.K. (2000). Propagation and conservation of Podophyllum hexandrum Royle: an important medicinal herb. Biol. Conserv. 92, 121-129.
43. Moraes, R.M., Burandt, C. Jr., Ganzera, M., Li, X., Khan, I. and Canel, C. (2000). The American mayapple revisited-Podophyllum peltatum-still a potential cash crop? Econ. Bot. 54, 471-476.
44. Moraes, R.M., Momm, H.G., Silva, B., Maddox, V., Easson, G.L., Lata, H. and Ferreira, D. (2005). Geographic information system method for assessing chemo-diversity in medicinal plants. Planta Med. 71, 1157-1164.
45. Canel, C., Dayan, F.E., Ganzera, M., Khan, I.A., Rimando, A., Burandt, C.L. and Moraes, R.M. (2001). High yield of podophyllotoxin from leaves of Podophyllum peltatum by in situ conversion of podophyllotoxin 4-O-β-D-glucopyranoside. Planta Med. 67, 97-99.
46. Dayan, F., Kuhajek, J., Canel, C., Watson, S. and Moraes R. (2003). Podophyllum peltatum possesses a β-glucosidase with high substrate specificity for the aryltetralin lignan podophyllotoxin. Biochim. Biophys. Acta 1645 (1-2), 157-163
47. Jackson, D.E. and Dewick, P.M. (1985). Tumor-inhibitory aryltetralin lignans from Podophyllum pleianthum. Phytochemistry 24, 2407-2409.
48. Moraes, R.M., Bedir, E., Barrett, H., Burandt, C., Canel, C. and Khan, I.A. (2002). Evaluation of Podophyllum peltatum accessions for podophyllotoxin production. Planta Med. 68, 341-344.
49. Maqbool, M., Cushman, K.E. and Moraes, R.M. (2004). Mayapple: a review of the literature from a horticultural perspective. Annual Report of the North Mississippi Research and Extension Center. Miss. Agric. For. Expt Sta. Info. Bull. 375, 313-319.
50. Cushman, K.E., Maqbool, M., Bedir, E., Lata, H., Khan, I.A. and Moraes, R.M. (2005). Growth and lignin content of American mayapple under increasing levels of shade. Hortic. Sci. 40, 60-63.
51. Cushman, K.E., Moraes, R.M., Gerard, P.D., Bedir, E., Silva, B. and Khan, I.A. (2006). Frequency and timing of leaf removal affect growth and podophyllotoxin content of Podophyllum peltatum in full sun. Planta 72, 824-829.
52. Giri, A. and Narasu, M.L. (2000). Production of podophyllotoxin from Podophyllum hexandrum: a potential natural product for clinically useful anticancer drugs. Cytotechnology 34, 17-26.
53. Fuss, E. (2003). Lignans in plant cell and organ cultures: an overview. Phytochem. Rev. 2 (3), 307-320.
54. Wink, M., Alfermann, W., Franke, R., Wetterauer, B., Distl, M., Windhovel, J., Krohn, O., Fuss, E., Garden, H., Mohagheghzadeh Eildi, E. and Ripplinger, P. (2005). Sustainable bioproduction of phytochemicals by plant in vitro cultures: anticancer agents. Plant Genet. Resour. 3, 90-100.
55. Guillon, S., Tremouillaux-Guiller, J., Pati, P.K., Rideau, M. and Gantet, P. (2006). Harnessing the potential of hairy roots: down of a new era. Trends Biotech. 24(9), 403-409.
56. Kutney, J.P. (1999). Biotechnology and synthetic chemistry-routes to clinically important compounds. Pure Appl. Chem. 71, 1025-1032.
57. Uden, W. van, Bos, J.A., Boeke, G.M., Woerdenbag, H.J. and Pras, N. (1997). The large-scale isolation of deoxypodophyllotoxin from rhizomes of Anthriscus sylvestris followed by its bioconversion into 5-vethoxypodophyllotoxin β-D-glucoside by cell cultures of Linum flavum. Nat. Prod. 60 (4), 401-403.
58. Kadakade, P.G. (1982). Growth and podophyllotoxin production in callus tissues of Podophyllum peltatum. Plant Sci. Lett. 25, 107-115.
59. Uden, W. van, Pras, N., Visser, J.F. and Malingre, T.M. (1989). Detection and identification of podophyllotoxin produced by cell cultures derived from Podophyllum hexandrum Royle. Plant Cell Rep. 8 (3), 165-168.
60. Uden, W. van, Pras, N. and Malingre, T.M. (1990). The accumulation of podophyllotoxin β-D-glucosidase by cell suspension cultures derived from the conifer Callistris drummondii. Plant Cell Rep. 9, 257-260.
61. Uden, W. van, Pras, N., Homan, B. and Malingre, T.M. (1991). Improvement of the production of 5-methoxypodophyllotoxin using a new selected root culture of Linum flavum L. Plant Cell Tiss. Org. Cult. 27, 115-121.
62. Konuklugil, B., Schmidt, R.J. and Alfermann, A.W. (1999). Accumulation of aryltetralin lactone lignans in cell suspension cultures of Linum nidiflorum. Planta Med. 65, 587-588.
63. Chattopadhyay, S., Srivastava, A.K., Bhojwani, S.S. and Bisaria, V.S. (2001). Development of suspension culture of Podophyllum hexandrum for the production of podophyllotoxin. Biotechnol. Lett. 23, 2063-2066.
64. Chattopadhyay, S., Srivastava, A.K. and Bisaria, V.S. (2002). Optimization of culture parameters for production of podophyllotoxin in suspension culture of Podophyllum hexandrum. Appl. Biochem. Biotechnol. 102/103, 381-393.
65. Chattopadhyay, S., Srivastava, A.K., Bhojwani, S.S. and Bisaria, V.S. (2002). Production of podophyllotoxin by plant cell cultures of Podophyllum hexandrum in bioreactor. J. Ferment. Bioeng. 93, 215-220.
66. Chattopadhyay, S., Bisaria, V.S. and Srivastava, A.K. (2003). Enhanced production of podophyllotoxin by Podophyllum hexandrum using in situ cell retention bioreactor. Biotechnol. Prog. 19, 1026-1028.
67. Pandey, H., Nandi, S.K., Chandra, B., Nadeem, M. and Palni, L.M.S. (2001). GA(3) induced flowering in Podophyllum hexandrum Royle: a rare alpine medicinal herb. Acta Physiol. Plant. 23, 467-474.
68. Xia, Z.Q., Costa, M.A., Proctor, J., Davin, L.B. and Lewis, N.G. (2000). Dirigentmediated podophyllotoxin biosynthesis in Linum flavum and Podophyllum peltatum. Phytochemistry 55, 537-549.
69. Molog, G., Empt, U., Kuhlmann, S., Uden, W. van, Pras, N., Alfermann, A. and Petersen, M. (2001). Deoxypodophyllotoxin 6-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum flavum involved in the biosynthesis of cytotoxic lignans. Planta 214(2), 288-294.
70. Hemmati, S., Schmidt, T. and Fuss, E. (2007). (+)-Pinoresinol/(-)-lariciresinol reductase from Linum perenne Himmelszelt involved in the biosynthesis of justicidin B. FEBS Lett. 581, 603-610.
71. Hemmati, S., Schneider, B., Schmidt, T.J., Federolf, K., Alfermann, A.W. and Fuss, E. (2007). Justicidin B 7-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum perenne Himmelszelt involved in the biosynthesis of diphyllin. Phytochemistry 68, 22-24.
72. Oostdam, A., Mol, J.N.M. and van der Plas, L.H.W. (1993). Establishment of hairy root cultures of Linum flavum producing the lignan 5-methoxypodophyllotoxin. Plant Cell Rep. 12, 474-477.
73. Schmitt, J. and Petersen, M. (2002). Influence of methyl jasmonate and coniferyl alcohol on pinoresinol and matairesinol accumulation in a Forsythia intermedia suspension culture. Plant Cell Rep. 20, 885-889.
74. Moraes, R.M., de Andrade, Z., Bedir, E., Dayan, F., Lata, H. and Khan, I. (2004). Arbuscular mycorrhiza improves acclimatization and increases lignan content of micropropagated mayapple (Podophyllum peltatum L.). Plant Sci. 166, 23-29.
75. Bedir, E., Tellez, M., Lata, H., Khan, I., Cushman, K.E. and Moraes, R.M. (2006). Post-harvest and scale up extraction of American mayapple leaves for podophyllotoxin production. Ind. Crops Prod. 24, 3-7.
76. Moraes-Cedeira, R.M., Burandt, C.L. Jr, Bastos, J.K., Nanayakkara, N.P.D. and McChesney, J.D. (1998). In vitro propagation of Podophyllum peltatum. Planta Med. 64, 42-46.
77. Cousins, M.M. and Adelberg, J.W. (2007). In vitro plant and organ culture of medicinal and nutraceutical species in laboratory and industrial scales. ISHS Acta Hortic. 756, 95-102.
78. Eyberger, A.L., Dondapati, R. and Porter, J.R. (2006). Endophyte fungal isolates from Podophyllum peltatum produces podophyllotoxin. J. Nat. Prod. 69(8), 1121-1124.
79. Puri, S.C., Nazir, A., Chawla, A., Arora, R., Riyaz-ul-Hasan, S., Amna, T., Ahmed, B., Verma, V., Singh, S., Sagar, R., Sharma, A., Kumar, R., Sharma, R.K. and Qazi, G.N. (2005). The endophytic fungus Trametes hirsuta as a novel alternative source of podophyllotoxin and related aryl tetralin lignans. J. Biotechnol. 122, 494-510.