Microbial transformations of cytotoxic natural products

Current Organic Chemistry

Volumn 3, Issue 4, 1999, Pages 309-326

  Atta ur Rahman, ^a   Farooq, Afgan ^a   Anjum, Shazia ^a   Choudhary, M Iqbal ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

Author keywords

[No Author keywords available]

Indexed keywords

LIPIDS; METABOLITES; PEPTIDES;

APHIDICOLIN; CYTOTOXIC; DIFFERENT CLASS; DITERPENOIDS; MICROBIAL TRANSFORMATION; NATURAL PRODUCTS; NOOTKATONE; SESQUITERPENES; TAXADIENES; TERPENOIDS;

ALKALOIDS;

4 CHROMANONE DERIVATIVE; ACRONINE; ALKALOID DERIVATIVE; ALPHA SANTONIN; ANTIBIOTIC AGENT; APHIDICOLIN; AROMATIC COMPOUND; BLEOMYCIN; CYTOTOXIC AGENT; DAUNORUBICIN; DITERPENOID; FLAVONE DERIVATIVE; GLUCOPYRANOSIDE; LAPACHOL; NATURAL PRODUCT; OLIVOMYCIN; PARTHENIN; QUINONE DERIVATIVE; SCLAREOL; SESQUITERPENE DERIVATIVE; STEROID; TERPENOID DERIVATIVE; TETRANDRINE; TRITERPENOID; VINBLASTINE; VINDOLINE; VINLEUROSINE;

ARTICLE; BACTERIAL METABOLISM; BIOTRANSFORMATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; NONHUMAN;

EID: 0032772475     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (89)

1. Q. Shi, K. Chen, S. L. Morris-Natschke and K. -H. Lee, Curr. Pharm. Design, 1998, 4, 233.
2. M. A. D. Boaventura, A. B. Oliveria, J. R. Hanson, P. B. Hitchcock and J. A. Takahashi, Phytochemistry, 1995, 40, 1667.
3. S. M. Mukhopadhyay, G. A. Handy, S. Funayama and G. A. Cordell, J. Nat. Prod., 1981, 44, 701.
4. G. R. Pettit, J. A. Hasler, K. D. Paul and C. L. Herald, J. Nat. Prod. 1981, 44, 701.
5. M. D. Antoun, D. Abramson, R. L. Tyson, C. Chang, J. L. McLaughlin, G. Peck and J. M. Cassady, J. Nat Prod., 1981, 44, 579.
6. Y. Choi, J. M. Pezutto, A. D. Kinghorn and N. R. Farnsworth, J. Nat. Prod., 1988, 51, 110.
7. P. W. LeQuesne, M. P. Pastore and R. F., Raffauf, J.Nat.Prod. 1976, 39, 391.
8. K. H. Lee, H. Nozaki, I. H. Hall, R. Kasai, T. Hirayama, H. Suzuki and R. Y. Wu, J. Nat. Prod., 1982, 45, 509.
9. A. M. Rao and D. G. I. Kingston, J. Nat. Prod., 1982, 45, 600.
10. T. A. Moskal, H. J. Woerdenbag, H. H. Kampinga, N. Press, F. S. El-Feraly, A. W. T. Konings and T. M. Malingre, Planta Med., 1992, 639.
11. D. H. Patterson, H. C. Murray, S. H. Eppstein, L. M. Reineke, A. Weintraub, P. D. Meister and H. M. Leigh, J. Am. Chem. Soc., 1952, 74, 5933.
12. A. J. Camell and S. M. Roberts, Chemistry in Britain, 1997, 33 (5), 49.
13. C. J. Sih, E. Abushanab and J. B. Jones, Ann. Rep. Med. Chem., 1977, 12, 298.
14. G. Schmidt-Kastner and P. Egerer in "Biotechnology", ed. K. Kieslich, Verlag Chemie, Weinheim, 1984, Vol. 6, p. 387.
15. A. L. Gutman, K. Zuobi and E. Guibe-Jampel, Tetrahedron Lett., 1990, 2037.
16. Y. Yamamoto, K. Yamamoto, T. Nishioka and J. Oda, Agric. Biol. Chem., 1988, 52, 3087.
17. C. A. G. M. Weijeres, A. deHaan and J. DeBont, Microbiol. Sci., 1988, 5, 156.
18. D. Mansuy and P. Battoni, in "Activation and Functionalization of Alkanes" ed. C.L. Hill, Wiley, New York, 1989.
19. S. W. May, Enzym, Microb. Technol., 1979, 1, 15.
20. D. R. Boyd, M. R. J. Dorrity, M. V. Hand, J. F. Malone N. D. Sharma, H. Dalton, D. J. Gray and G. N. Sheldrake J. Am. Chem. Soc., 1991, 113, 667.
21. G. L. Lemiere, J. A. Lepoivre and F. C. Alderweireldt, Tetrahedron Lett., 1985, 4527.
22. C. T. Walsh and Y.-C. J. Chen, Angew. Chem. Int. Ed. Engl., 1988, 27, 333.
23. R. S. Philips and S. W. May, Enzy. Microb. Technol., 1981, 3, 9.
24. M. H. Findeis and G. M. Whitesides, J. Org. Chem., 1987, 52, 2838.
25. H. M. Sweers and C. -H. Wong, J. Am. Chem. Soc., 1986, 108, 6421.
26. M. Akhtar, N. B. Botting, M. A. Cohen and D. Gani, Tetrahedron, 1987, 43, 5899.
27. M. Morrison and G. R. Schonbaum, Ann. Rev. Biochem., 1976, 45, 458.
28. F. Effenberger and T. Ziegler, Angew. Chem. Int. Ed. Engl. 1987, 26, 458.
29. C.-S. Chen and C. J. Sih, Angew. Chem. Int. Ed. Engl., 1989, 28, 695.
30. P. H. Buist and G. P. Dimnik, Tetrahedron Lett., 1986, 1457.
31. C. T. Goodhue, Microb. Transform. Bioact. Compd., 1982, 1, 9.
32. J. M. Scwab and B. S. Henerson, Chem. Rev., 1990, 90, 1203.
33. C. Fuganti and P. Grasselli, in "Biocatalysis in Agricultural Biochemistry", ACS, Symposium Series, eds. J. R. Whitaker and P. E. Sonnet, 1988, Vol. 389, p. 359.
34. E. J. Toone, E. S. Simon, M. D. Beanarski and G. M. Whitesides, Tetrahedron, 1989, 45, 5365.
35. W. D. MacLeod, Tetrahedron Lett., 1965, 4779.
36. A. Farooq, "Structural, Synthetic and Biotransformation Studies of Some Steroidal Alkaloids, Steroids and Sesquiterpenes", Ph.D. thesis, 1996, p.114, University of Karachi.
37. M. Miyazawa, T. Uemura and H. Kameoka, Phytochemistry, 1995, 40,. 793.
38. W. - R. Abraham, K. Kieslich, B. Stumpt and L. Ernst, Phytochemistry, 1992, 31, 3749.
39. J. R. Hanson, P. B. Hitchock and R. Manickanavasager, Phytochemistry, 1994, 37, 1023.
40. G. H. Rodriguez, N. Towers and J. C. Mitchell, Phytochemistry, 15, 1976, 1573.
41. Atta-ur-Rahman, M. S. Shekhani, S. Perveen, Habib-ur-Rehman, A. Yasmin, A. Z. Haq and D. Sheikh, J. Chem. Res. (M), 1989, 501.
42. J. S. Sohni, S. R. Rojatkar, M. M. Kulkami, N. N. Dhaneshawar, S. S. Tavale, T. N. Cururow and B. A. Nagasampagi, J. Chem. Soc. Perkin. Trans I, 1988, 157.
43. Atta-ur-Rahman, M. I. Choudhary, A. Ata, M. Alam, A. Farooq, S. Parveen, M. S. Shekhani and N. Ahmed, J. Nat. Prod., 1994, 57, 1251.
44. T. J. Schmidt, C. M. Passreiter, D. Wendisch and G. Willuhn, Phytochemistry, 1995, 40, 1213.
45. M. Stoll and M. Hinder, Helv. Chim. Acta., 1953, 36, 1984.
46. A. G. Grandos, A. Martinez, A. Ortiz, M. E. Onorato and J. M. Arias, J. Nat. Prod., 1990, 53, 441.
47. Atta-ur-Rahman, A. Farooq and M. I. Choudhary, J. Nat. Prod., 1997, 60, 1038.
48. K. K. Bhutani and R. N. Thakur, Phytochemistry, 1991, 30, 3599.
49. H. Hikino, Y. Tokuoka and T. Takemoto, Chem. Pharm. Bull., (Japan), 1970, 2127.
50. Atta-ur-Rahman, M. I. Choudhary, F. Shaheen, A. Rauf and A. Farooq, Nat. Prod. Lett., 1998, 12(3), 215.
51. Y. Garcia, A. G. Granados, A. Martnez, A. Parra and F. Rivas, J. Nat. Prod., 1995, 58, 1498.
52. G. P. Noy and S. Spadari, Biochem. Biophys. Res. Commun., 1979, 88, 1194.
53. R. A. Bucknall-H. Moores, R. Simms and B. Hesp., Antimicrob. Agents Chemother., 1973, 4, 294.
54. A. N. Starrat and S. R. Loschiavo, Can. J. Microbiol., 1974, 20, 416.
55. R. L. Cargill, D. F. Bushey, J. R. Dalton, R. S. Parasad, R. D. Dyer and J. Bordner, J. Org. Chem., 1981, 46, 3389.
56. R. E. Ireland, D. J. Godfrey and S. Thaisrivongs, J. Am. Chem. Soc., 1981, 103, 2446.
57. W. Dalziel, B. Hesp, K. M. Stevenson and J. A. J. Jarvis, J. Chem. Soc., Perkin Trans 1, 1973, 2841.
58. J. Ipsen, J. Fuska, A. Foskova and J. P. Rosazza, J. Org. Chem., 1982, 47, 3278.
59. J. R. Hanson, A. G. Jarvis and A. H. Ratcliffe, Phytochemistry, 1992, 31, 799.
60. J. R. Hanson and A. G. Jarvis, Phytochemistry, 1994, 36, 1395.
61. J. R. Hanson, A. G. Jarvis, F. Laboret and J. Takahashi, Phytochemistry, 1995, 38, 73.
62. J. R. Hanson, P. B. Hitchcock and A. G. Jaruis, Phytochemistry, 1997, 44, 1055.
63. G. N. Kumar, J. E. Oatis, K. R. Thornburg, F. J. Heldrich, E. S. Hazard and T. Walle, Drug Metab. Dispos., 1994, 22, 177.
64. S. H. Hu, X. F. Tian, W. H. Zhu and Q. C. Fang, J. Nat. Prod., 1996, 59. 1006.
65. S. H. Hu, X. F. Tian, W. H. Zhu and Q. C. Fang, Tetrahedron, 1996, 52, 8739.
66. C. R. Carreras, J. Rodriguez, H. J. Silva, P. Rossomando, O. S. Giordano and E. Guerreiro, Phytochemistry, 1996, 41, 473.
67. F. A. Bardria and C. D. Hufford, Phytochemistry, 1991, 30, 2265.
68. J. R. Hanson, P. B. Reese, J. A. Takahashi, and M. R. Wilson, Phytochemistry, 1994, 36, 1391.
69. G. Maatooq, S. E. Sharkaway, M. S. Afifi and J. P. Rosazza, J. Nat. Prod., 1995, 58, 165.
70. J. Fuska, J. Prousek, J. P. Rosazza and M. Budesinsky, Steroids, 1982, 40, 157.
71. J. Fuska, A. Fuskova, J. P. Rosazza and A. W. Nicholas, Neoplasma, 1984, 31, 31.
72. Atta-ur-Rahman, M. I. Choudhary, M. Jabeen and A. Farooq (unpublished work).
73. J. Fuska, B. Proksa, M. Sturdikova and A. Fuskova, Phytochemistry, 1986, 25, 1613.
74. N. Neuss, G. E. Mallet, D. R. Brannon, J.A. Mabe, H.R. Horton and L. L. Huckstep, Helv. Chim. Acta, 1974, 57, 1886.
75. J. P. Schaumberg and J. P. Rosazza, J. Nat. Prod., 1981, 44, 478.
76. P.J. Davis and J. P. Rosazza, J. Org. Chem., 1976, 41, 2548.
77. P. J. Davis, D. Wiese and J. P. Rosazza, J. Nat. Prod., 1977, 40, 239.
78. J. P. Rosazza, J. Nat. Prod., 1978, 41, 297.
79. S. L. Otten and J. P. Rosazza, J. Nat. Prod., 1981, 44, 562.
80. A. R. Ibrahim and Y. J. Abul-Hajj, J. Nat. Prod., 1990, 53, 1471.
81. S. R. Udupa, A. Banerji and M. S. Chadha, Tetrahedron Lett., 1969, 37, 4003.
82. S. R. Udupa and M. S. Chadha, Indian J. Biochem. Biophys., 1972, 9, 141.
83. S. R. Udupa and M. S. Chadha, Indian J. Biochem. Biophys., 1978, 15, 329.
84. S. R. Udupa and M. S. Chadha, Indian, J. Biochem. Biophys., 1978, 115, 333.
85. H. Umezawa, Y. Takahashi, A. Fujii, T. Saino, T. Shirai and T. Takita, J. Antibiot., 1973, 26, 1117.
86. P. F. Wiley, and V. P. Marshall, J. Antibiot., 1975, 28, 838.
87. N. R. Bachur, M. Steele, W.D. Meriwether and R. Hildebrand, J. Med. Chem., 1976, 19, 651.
88. H. Schmitz and C. A. Claridge, J. Antibiot., 1977, 30, 635.
89. M. S. Raju, G-S. Wu, A. Gard and J. P. Rosazza, J. Nat. Prod., 1982, 45, 321.