Effect of precursors feeding and media manipulation on production of novel anticancer pro-drug camptothecin from endophytic fungus

Brazilian Journal of Microbiology

Volumn 43, Issue 4, 2012, Pages 1476-1489

  Amna, Touseef ^a,b   Amina, Musarat ^b   Sharma, P R ^a   Puri, S C ^a   Al Youssef, Hanan M ^b   Al Taweel, Areej M ^b   Qazi, G N ^a  

^a CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Camptothecin; Cancer; Entrophospora infrequens; Nothapodytes foetida; Precursors

Indexed keywords

EID: 84874385926     PISSN: 15178382     EISSN: 16784405     Source Type: Journal    
DOI: 10.1590/S1517-83822012000400032     Document Type: Article

References (51)

1. Aiyama, R.; Nagai, H.; Kokata, K.; Shinonara, C.; Swada, S. (1988).Camptothecin derivative from Nothapodytes foetida. Photochem. 27, 3663-3664.
2. Amna, T.; Puri, S.C.; Verma, V.; Sharma, J.P.; Khajuria, R.K.; Musarrat, J.; Spiteller, M.; Qazi, G.N. (2006). Bioreactor Studies on the Endophytic Fungus Entrophospora infrequens for the Production of an anticancer alkaloid Camptothecin. Canadian Journal of Microbiol. 52, 189-196.
3. Amna, T.; Khajuria, R.K.; Puri, S.C.; Verma, V.; Qazi, G.N. (2006). Quantification of Camptothecin in an Endophytic fungus by Liquid chromatography-Positive mode Electrospray Ionization Tandem Mass spectrometry (LC-MS/MS). Current Science. 91 (2), 208-212.
4. Arnold, A.E.; Maynard, Z.; Gilbert, G.S.; Coley, P.D.; Kursar, T.A. (2000). Are tropical fungal endophytes hyperdiverse?. Ecol. Lett. 3, 267-274.
5. Battersby, A.R.; Burnett, A.R.; Parsons, P.G. (1969a). Alkaloid biosynthesis. Partial synthesis and isolation of vincoside and isovincoside: biosynthesis of the three major classes of indole alkaloids from vincoside. J Chem Soc Chem Comm. 15, 1193-1200.
6. Battersby, A.R.; Burnett, A.R.; Parsons, P.G. (1970). Preparation and isolation of deoxyloganin: Its role as precursor of loganin and the indole alkaloids. J. Chem. Soc., Chem. Comm. 13, 826.
7. Battersby, A.R.; Brown, R.T.; Kapil, R.S.; Plunkett, A.O.; Taylor, J.B. (1966a). Biosynthesis of the indole alkaloids. Chem. Comm. 2, 46-47.
8. Battersby, A.R.; Brown, R.T.; Knight, J.A.; Martin, J.A.; Plunkett, A.O. (1966b). Biosynthesis of the indole alkaloids from a monoterpene. Chem. Comm. 12, 346-347.
9. Battersby, A.R.; Burnett, A.R.; Parsons, P.G. (1968a). Partial Synthesis and Isolation of Vincoside and Isovincoside: Biosysnthesis of the Three Major Classes of Indoles Alkaloids from the ß-Carboline System. J.Chem. Soc., Chem. Comm. 1282.
10. Battersby, A.R.; Burnett, A.R.; Parsons, P.G. (1969b). Alkaloid Biosynthesis. Part XIV. Secologanin: Its Conversion in Ipecoside and its Role as Biological Precursor of the Indole Alkaloids. J. Chem. Soc. (C), 1187.
11. Battersby, A.R.; Brown, R.T.; Kapil, R.S.; Martin, J.A.; Plunkett, A.O. (1966c) Role of loganin in the biosynthesis of indole alkaloids. Chem. Comm., 23, 890-891.
12. Bodley, J.A.; Cumming, F.N.; Shapiro, T.A. (1998). Effects of camptothecin, a topoisomerase I inhibitor on Plasmodium falciparum. Biochem. Phar. 55,709-711.
13. Christen, P. et al. (1995). Microbial lipase production on a polymeric resin. Biotechnol. Tech. 9, 597-600.
14. Demain, A.L. (1961). Industrial microbiology. Sci. 214, 987-995.
15. Dewick, P.M. (2002). Medicinal Natural Products-A Biosynthetic Approach, second edition;John Wiley & sons Ltd.England, 321.
16. Escher, S.; Loew, P.; Angoni, D. (1970).The role of hydroxygeraniol and hydroxynerol in the biosynthesis of loganin and indole alkaloids, J. Chem. Soc. Chem. Commun. 823-825.
17. Facchini, P.J.; and Bird, D.A.; St-Pierre, B. (2004).Can Arabiodopsis make complex alkaloids. Trends Plant Sci. 9,116-22.
18. Goodman, R.N.; Kiraly, Z.; Wood, R.K.S. (1986).The Biochemistry and Physiology of Plant Disease. University of Missouri Press, Columbia.
19. Grayson, Y. (1982). Antibiotics, Chemotherapeutics and Antibacterial agents for disease control. New York, John Wiley & Sons.
20. Guttierrez-Rojas, M. et al. (1995). Citric acid and Polyol production by Aspergillus niger at high glucose concentration in solid-state fermentation on inert support. Biotechnol. Lett. 17, 219-222.
21. Hall, E.S.; McCapra, F.; Money, T.; Fukumoto, K.; Hansonm, J.R.; Mootoo, B.S.; Phillips, G.T.; Scott, A.I. (1966). Concerning the terpenoid origin of indole alkaloids: biosynthetic mapping by direct mass spectrometry. Chem. Commun. 12, 348-350.
22. Hall, I.R. (1977). Species and mycorrhizal infections of New Zealand Endogonaceae. Transactions of the British Mycology Soc. 68,341-356.
23. Kutney, J.P.; Beck, J.F.; Nelson, V.R.; Sood, R.S. (1971). Studies on indole alkaloid biosynthesis. VI. The eburnamine-vincamine alkaloids. J. Am. Chem. Soc. 93(1), 255-257.
24. Kutney, J.P.; Cretney, W.J.; Hadfeld, J.R.; Hall, E.S.; Nelson V.R.; Wigfield, D.C. (1968). Studies on indole alkaloid biosynthesis. J. Am. Chem. Soc. 90 (13), 3566-3567.
25. Kusari, S.; Zühlke, S.; Spiteller, M. (2009). An Endophytic Fungus from Camptotheca acuminata That Produces Camptothecin and Analogues. J. Nat. Prod. 72, 2-7.
26. Lang, A. (1970). Gibberellins: Structure and Metabolism. Annu. Rev. Plant. Physiol. 21, 537-570.
27. Larroche, C. (1996). Microbial growth and sporulation behaviour in solid-state Fermentation. J. Sci. Ind. Res. 55, 408-423.
28. Leete, E. (1961). The incorporation of tryptophan into serpentine and reserpine. Tetrahedron. 14, 1-2.
29. Leete, E.; and Ueda, S. (1966). Biosynthesis of the vinca alkaloids. The incorporation of geraniol-3-14C into catharanthine and vindoline. Tetrahedron Lett. 4915-4918.
30. Leete, E.; Ghosal, S.; Edwards, P.W.; (1962). Biosynthesis of the Non- Tryptophan Derived Portion of Ajmaline. J. Am. Chem. Soc. 84, 1068.
31. Li, S.Y.; Adair, K.T. (1994). Camptotheca acuminata Decaisne, Xi, Shu. a Promising Anti-Cancer and Anti-Viral Tree for the 21st Century. A Henry M. Rockwell Monograph (ed. Stephen, F.), Austin State University, Texas.
32. Li, S.Y.; Wang, Y.J.; Beasley, R.S.; Northrup, K. (2000). Anticancer happytrees Decaisne Research Report. Arthur Temple College of Forestry, Stephen en F. Austin State University, Texas.
33. Loew, P.; Goeggel, H.; Angoni, D. (1966). A monoterpene precursor in the biosynthesis of indole alkaloids. Chem Commun., 347.
34. McCapra, F.; Money, T.; Scott, A.I.; Wright, I.G. (1965). Biosynthesis of the indole alkaloids: vindoline. Chem. Comm. 537.
35. Money, T.; Wright, I.G.; McCapra, F.; Hall, E.S.; Scott, A.I. (1968). Biosynthesis of indole alkaloids. Vindoline. J.Am. Chem. Soc., 90, 4144-4150.
36. Okami, Y.; Okazaki, T.; Kitahara, T.; Umezawa, H.J. (1976). Studies on marine microorganisms. A new antibiotic aplasmomycin, produced by a streptomyces isolated from shallow sea mud. J. Antibiot. 32, 1019-1025.
37. Okami, Y. (1986). Marine microorganisms as a source of bioactive agents. Microb. Ecol. 12, 65-78.
38. Priel, E.; Showalter, S.D.; Blair, D.G. (1991). Inhibition of human immunodeficiency virus (HIV-1) replication in vitro by non-cytotoxic doses of camptothecin a topoisomerase -I inhibitor, AIDS Res. Hum. Retroviruses. 7, 65-72.
39. Puri, S.C.; Verma, V.; Amna, T.; Qazi, G.N.; Spiteller, M. (2005). An Endophytic Fungus from Nothapodytes foetida that Produces Camptothecin. J. Nat. Prod. 68 (12), 1717-1719.
40. Puri, S.C.; Amna, T.; Khajuria, A.; Gupta, A.; Arora, R.; Spiteller, M.; Qazi, G.N., (2008). Immunomodulatory activity of the novel fungal endophyte Entrophospora infrequens isolated Nothapodytes foetida (Wight) Sleumer., Acta. Microbiologica Immunologica Hungarica. 54(3), 237-260.
41. Rehman, S.; Shawl, A.S.; Kour, A.; Andrabi, R.; Sudan, P.; Sultan, P.; Verma, V.;Qazi, G.N. (2008). An Endophytic Neurospora sp. from Nothapodytes foetida Producing Camptothecin. Applied Biochemistry and Microbiol. 44(2),203-209.
42. Sheriha, G.M.; Rapoport, H.; (1976). Biosynthesis of Camptotheca acuminate alkaloids, Phytochem.15, 505-508.
43. Stowe, B.B.; and Yamaki, T. (1957). The History and physiological action of the Gibberellins, Annu. Rev. Plant. Physiol. 8, 181-216.
44. Tanaka Y. (1992). In: The Search for bioactive Compounds from Microorganisms; Omura S. Ed: Springer -Verlag: New York; 303-324.
45. Van, A.J.; Hengel, M.P.; Harkes, H.J.; Wichers, P.; Hesselink, G.M.; Buitelaar, R.M. (1992). Characterization of callus formation and camptothecin production by cell lines of Camptotheca acuminate. Plant Cell Tissue Org. Culture. 28, 11-18.
46. Verpoorte, R. Van der Heijden, R.; Schripsema, J.; Hoge, J.H.C.; Hoopen, H.J.G. (1993). Plant cell biotechnology for the production of alkaloids: present status and prospects. J. Nat. Prod. 56, 186-207.
47. Wall, M.E.; Wani, M.C.; Cook, C.E.; Palmer, K.H. (1966). Plant Antitumor Agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J. Amer. Chem. Soc. 88, 3888-3890.
48. Wang, J.C. (1985). DNA Topoisomerases. Annu. Rev. Biochem. 54, 665-697.
49. Washo-Stultz, D.; Crowley-Weber, C.L.; Dvorakova, K.; Bernstein, C.; Bernstein, H.; Kunke, K.; Waltmire, C.N.; Garewal, H.; Payne, C.M. (2002). Role of mitochondrial complexes I and II reactive oxygen species and arachidonic acid metabolism in deoxycholate-induced apoptosis. Cancer Lett. 177, 129-144.
50. Wyllie, A.H.; Kerr, J.F.; Currie, A.R. (1980). Cell death: the significance of apoptosis. Int. Rev. Cyt. 68: 251-306.
51. Young, D.H.; Michelotti, E.J.; Sivendell, C.S.; Krauss, N.E. (1992). Antifungal properties of taxol and various analogues. Experientia. 48, 882-885.