Biological transformations of steroidal compounds: A review

Steroids

Volumn 77, Issue 12, 2012, Pages 1267-1290

  Bhatti, Haq Nawaz ^a   Khera, Rasheed Ahmad ^a  

^a UNIVERSITY OF AGRICULTURE   (Pakistan)

Author keywords

Biotransformation; Fungi; Hormones

Indexed keywords

16 DEHYDROXYPROGESTERONE; 3ALPHA HYDROXY 5,6BETA CYCLOPROPANO 5BETA ANDROSTA 17 ONE; 3BETA HYDROXY 5,6ALPHA CYCLOPROPANO 5ALPHA ANDROSTA 17 ONE; 3BETA HYDROXY 5,6BETA CYCLOPROPANO 5BETA CHOLESTANE; 5,6BETA CYCLOPROPANO 5BETA ANDROSTA 3,17 DIONE; 6ALPHA CYCLOPROPANO 5ALPHA ANDROSTA 3,17 DIONE; ADRENOSTERONE; ANDROSTA 4 ENE 3,17 DIONE; BUFADIENOLIDE DERIVATIVE; BUFALIN; BUFOGENIN; CINOBUFAGIN; DANAZOL; ERGOSTEROL; ETHISTERONE; GESTONORONE; GUGGULSTERONE; MESTEROLONE; MESTRANOL; NORETHISTERONE; PHYTOSTEROL; PRASTERONE; PREGNENOLONE; PROGESTERONE; SAPOGENIN; STEROID; STEROID HORMONE; STEROL; TESTOSTERONE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ASPERGILLUS FUMIGATOUS; ASPERGILLUS NIGER; BACILLUS; BIOTRANSFORMATION; CATALYSIS; CEPHALOSPORIUM APHIDICOLA; CHEMICAL STRUCTURE; CUNNINGHAMELLA ELEGANS; CURVULARIA LUNATA; DRUG ISOLATION; DRUG METABOLISM; DRUG STRUCTURE; FERMENTATION; FUNGUS; FUSARIUM; FUSARIUM CULMORUM; FUSARIUM OXYSPORUM; GEOBACILLUS STEAROTHERMOPHILUS; GIBBERELLA FUJIKUROI; METABOLITE; MUCOR GRISEOCYANUS; MYCOBACTERIUM; NECTRIA HAEMATOCOCCA; NONHUMAN; PIMELOBACTER SIMPLEX; PLEUROTUS OESTREATUS; REVIEW; SAPROLEGNIA HYPOGYNA; STEROID HYDROXYLATION; STEROID METABOLISM; THAMNOSTYLUM PIRIFORME; TRICHOTHECIUM ROSEUM;

ANIMALS; BIOTRANSFORMATION; HORMONES; HUMANS; MICROBIOLOGY; STEROIDS; STEROLS;

FUNGI; MAMMALIA;

EID: 84865827131     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.07.018     Document Type: Review

References (115)

1. A.G. Mensah-Nyagan, L. Meyer, V. Schaeffer, C. Kibaly, and C. Patte-Mensah Evidence for a key role of steroids in the modulation of pain Psychoneuroendocrinology 34 2009 169 177
2. L. Sedlaczek Biotransformations of steroids Crit Rev Biotechnol 7 1988 187 236
3. W. Charney, and L.H. Herzong Microbial transformations of steroids 1976 Academic Press New York pp. 5-73
4. J.A. Hogg Steroids, the steroid community and Upjohn in perspective: a profile of innovation Steroids 257 1992 593 616
5. Mukherjee Mahato Steroid transformations by microorganisms Phytochemistry 23 1984 2131 2154
6. S.B. Mahato, and A. Mukherjee Steroid transformations by microorganisms-II Phytochemistry 24 1985 1403 1421
7. S.B. Mahato, S. Banergee, and I. Mazumder Metabolism of progesterone by a Bacillus species J Chem Res Synop 6 1989 184 185
8. S. Ahmad, S.K. Garg, and B.N. Johri Biotransformation of sterols: selective cleavage of the side chain Biotechnol Adv 10 1992 1 67
9. S.B. Mahato, and I. Mazumder Current trends in microbial steroid biotransformation Phytochemistry 34 1995 883 898
10. S.B. Mahato, and S. Garai Advances in microbial steroid biotransformation Steroids 62 1997 332 345
11. P. Fernandes, A. Cruz, B. Angelova, H.M. Pinheiro, and J.M.S. Cabral Microbial conversion of steroid compounds: recent developments Enzyme Microb Technol 32 2003 688 705
12. Z. Tuba, C.W. Barden, A. Dancsi, E. Francsics-Czinege, E.C. Molnar, J. Csorgei, G. Falkay, S.S. Koide, N. Kumar, K. Sundaram, V. Dukat-Abrok, and G. Balogh Synthesis and biological activity of a new progestogen, 16-methylene-17alpha-hydroxy-18-methyl-19-norpregn-4-ene-3, 20-dione acetate Steroids 65 2000 266 274
13. D. Ko, A.S. Heiman, M. Chen, and H.J. Lee New steroidal anti-inflammatory antedrugs: methyl 21-desoxy-21-chloro-11β,17α-dihydroxy-3,20-dioxo- 1,4-pregnadiene-16α-carboxylate, methyl 21-desoxy-21-chloro-11β -hydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylate, and their 9α-fluoro derivatives Steroids 65 2000 210 218
14. C. Siemes, L.E. Visser, F.H. De-Jong, Coebergh W. Jan-Willem, and A.G. Uitterlinden Cytochrome P450 3A gene variation, steroid hormone serum levels and prostate cancer Steroids 75 2010 1024 1032
15. B.N. Diaz-Chico, F.G. Rodriguez, A. Gonzalez, R. Ramirez, C. Bilbao, A.C. Leon, A.A. Jaime, R. Chirino, and D. Navarro Androgens and androgen receptors in breast cancer J Steroid Biochem Mol Biol 105 2007 1 15
16. J.O. Hohnston Aromatase inhibitors E.J. Parish, W.D. Nes, Biochemistry and function of sterols 1987 CRC Press Boca Raton, FL 23 53
17. L.L. Frye, and D.A. Leonard Lanosterol analog: dual action inhibitors of cholesterol biosynthesis E.J. Parish, W.D. Nes, Biochemistry and function of sterols 1987 CRC Press Boca Raton, FL 23 53
18. S.K. Chung, C.H. Ryoo, H.W. Yang, J.Y. Shim, M.G. Kang, K.W. Lee, and H.I. Kang Synthesis and bioactivities of steroid derivatives as antifungal agents Tetrahedron 52 1998 15899 15914
19. Suzuki K, Nakata T, Shimizu T, Enomoto K. US Patent, 1998, 5, 712,109.
20. Dombrowski AW, Hazuda DJ, Polishook JD, Felock PJ, Singh SB, Zink DL. 2000, WO Patent, 0036132.
21. D. Arthan, J. Svasti, P. Kittakoop, D. Pittayakhachonwut, M. Tanticharoen, and Y. Thebtaranonth Antiviral isoflavonoid sulfate and steroidal glycosides from the fruits of Solanum torvum Phytochemistry 59 2002 459 463
22. W.E. Brown The impact of biotechnology to health care industry Ann Rep Fermen Proc 7 1984 135
23. W.H. Liu, C.W. Kui, K.L. Wu, C.Y. Lee, and W.Y. Hsu Transformation of cholesterol to testosterone by Mycobacterium sp. J Ind Microbiol 13 1994 167 171
24. W.H. Liu, and C.K. Lo Production of testosterone from cholesterol using a single-step microbial transformation of Mycobacterium sp. J Ind Microbiol Biotechnol 19 1997 269 272
25. N. Phase, and S. Patil Natural oils are better than organic solvents for the conversion of soybean sterols to 17-ketosteroids by Mycobacterium fortuitum World J Microbiol Biotechnol 10 1994 228 229
26. A.C.P. Dias, J.M.S. Cabral, and H.M. Pinheiro Sterol side-chain cleavage with immobilized Mycobacterium cells in water-immiscible organic solvents Enzyme Microb Technol 16 1994 708 714
27. W.H. Liu, W.C. Horng, and M.S. Tsai Bioconversion of cholesterol to cholest-4-en-3-one in aqueous/organic solvent two-phase reactors Enzyme Microb Technol 18 1996 184 189
28. Z. Wang, F. Zhao, X. Hao, D. Chen, and D. Li Microbial transformation of hydrophobic compound in cloud point system J Mol Catal B 27 2004 147 153
29. R. Kumar, J.S. Dahiya, D. Singh, and P. Nigam Biotransformation of cholesterol using Lactobacillus bulgarius in a glucose-controlled bioreactor Bioresour Technol 78 2001 209 211
30. K. Kieslich Microbial side-chain degradation of sterols J Basic Microbiol 25 1985 461 474
31. J.L. Yan, S.S. Lee, and K.C. Wang Microbial transformation of 3-hydroxy-5, 6-cyclopropanocholestanes-An alternative route to 6-methylsteroids Steroids 65 2000 863 870
32. G. Ambrus, A. Jekkel, E. Ilky, G. Horváth, and Z. Böscskei Novel 26-oxygenated products in microbial degradation of ergosterol Steroids 60 1995 626 629
33. G. Ambrus, E. Ilky, A. Jekkel, G. Horváth, and Z. Böscskei Microbial transformation of β-sitosterol and stigmasterol into 26-oxygenated derivatives Steroids 60 1995 621 625
34. O.V. Egorova, S.A. Gulevskaya, I.F. Puntus, A.E. Filonov, and M.V. Donova Production of androstenedione using mutants of Mycobacterium sp. J Chem Technol Biotechnol 77 2002 141 147
35. A. Malaviya, and J. Gomes Androstenedione production by biotransformation of phytosterols Biores Technol 99 2008 6725 6737
36. W.H. Liu, C.P. Pan, and C.K. Lo Transformation of phytosterol to testosterone by a Mycobacterium sp. in an airlift fermentor Food Sci Agric Chem 4 2001 139 142
37. K.C. Wang, B.J. You, J.L. Yan, and S.S. Lee Microbial transformation of lanosterol derivatives with Mycobacterium sp. (NRRL B-3805) J Nat Prod 58 1995 1222 1227
38. J.F. Templeton, Y. Liang, T.H. Zeglam, and F.S. LaBella Synthesis of 20-hydroxy-, 20-amino- and 20-nitro-14-hydroxy-21-nor-5 beta, 14 beta-pregnane C-3 glycosides and related derivatives: structure-activity relationships of pregnanes that bind to the digitalis receptor J Med Chem 36 1993 42 45
39. J.F. Templeton, P. Setiloane, V.P.S. Kumar, Y. Ling, J. Jin, and M.A. Boehmer Synthesis of 3β,14-dihydroxy-5β, 14β-pregnan-20-one C-3 derivatives: ozonolysis of digitoxin and digitoxigenin and their derivatives followed by zinc-acetic acid reduction to the C-21 methyl ketone J Chem Soc Perkin Trans 1 4 1991 823 829
40. J. Manosroi, S. Saowakhon, and A. Manosroi Enhancement of 17α-hydroxyprogesterone production from progesterone by biotransformation using hydroxypropyl-β-cyclodextrin complexation technique J Steroid Biochem Mol Biol 112 2008 201 204
41. S.H. Hu, G. Genain, and R. Azerad Microbial transformation of steroids: contribution to 14α-hydroxylations Steroids 60 1995 337 352
42. K.E. Smith, F. Ahmed, R.A.D. Williams, and S.L. Kelly Microbial transformations of steroids-VIII. Transformation of progesterone by whole cells and microsomes of Aspergillus fumigatus J Steroid Biochem Mol Biol 49 1994 93 100
43. A.M. Khalil, and M.M. Eman Microbiological transformation of progesterone by some zoosporic fungi J Basic Microbiol 4 1996 255 259
44. T. Kolek, and A. Świzder Biotransformation XLV. Transformations of 4-ene-3-oxo steroids in Fusarium culmorum culture J Steroid Biochem Mol Biol 67 1998 63 69
45. S. Al-Awadi, M. Afzal, and S. Oommen Studies on Bacillus stearithermophillus. Part I. Transformation of progesterone to a new metabolite 9,10-seco-4-pregnene-3,9,20-trione J Steroid Biochem Mol Biol 78 2001 493 498
46. K.M. Madyasth, and T. Joseph Transformation of 16-dehydroprogesterone and 17α-hydroxyprogesterone by Mucor piriforme Appl Microbiol Biotechnol 41 1994 170 177
47. E.E. Baulieu, P. Robel, A. Fellous, Y. Duchossoy, V. Fontaine-Lenoir, and S. David Toward a novel approach of neuroprotection and treatment of Alzbeimerś disease J Mol Neurosci 24 2004 63 65
48. K.M. Madyasth, and T. Joseph Transformation of dehydroepianrosterone pregnenolone by Mucor piriforme Appl Microbiol Biotechnol 44 1995 339 343
49. A. Farooq, and S. Tahara Biotransformation of testosterone and pregnenolone catalyzed by the fungus Botrytis cinerea J Nat Prod 63 2000 489 491
50. O. Schaaaf, and K. Dettner Transformation of steroids by Bacillus strains isolated from the foregut of water beetles (Coleoptera: Dytiscidae): II. Metabolism of 3β-hydroxypregn-5-en-20-one (pregnenolone) J Steroid Biochem Mol Biol 75 2000 187 199
51. D. Fernandes, B. Loi, and C. Porte Biosynthesis and metabolism of steroids in molluscs J Steroid Biochem Mol Biol 127 2011 189 195
52. M.I. Choudhary, I. Batool, S.A.A. Shah, S.A. Nawaz, and Atta-ur-Rehman Microbial hydroxylation of pregnenolone derivatives Chem Pharm Bull 11 2005 1455 1459
53. M.R. Wilson, W.A. Gallimore, and P.B. Reese Steroid transformations with Fusarium oxysporum var. cubense and Colletotrichum musae Steroids 64 1999 834 843
54. S. Schwarz, S. Ring, G. Weber, H.-J. Teichmüller Palmer, C. Pfeiffer, and B. Undentsch Synthesis of 13-ethyl-11-methylene-18, 19-dinor-17α-pregn-4-en-20-yn-17-ol (desogestrel) and its metabolite 3-oxo desogestrel Tetrahedron 50 1994 10709 10720
55. S.H. Hu, X.F. Tian, Y.H. Sun, and G.D. Han Microbial hydroxylation of 13-ethyl-17β-hydroxy-18, 19-dinor-17α-pregn-4-en-20-yn-17-one Steroids 61 1996 407 410
56. S.H. Hu, X.F. Tian, and G.D. Han Novel microbial hydroxylation of 13-ethyl-17β-hydroxy-18, 19-dinor-17α-pregn-4-en-20-yn-3-one Steroids 63 1998 88 92
57. D. Rosi, H.C. Neuman, R.G. Christiansen, H.P. Schane, and G.O. Potts Isolation, synthesis, and biological activity of five metabolites of danazol J Med Chem 20 1977 349 352
58. F. Ahmed, R.A.D. Williams, and K.E. Smith Microbial transformations of steroids-X. Cytochromes P-450 11α-hydroxylase and C17-C20 lyase and A 1-ene dehydrogenase transform steroids in Nectria haematococca J Steroid Biochem Mol Biol 58 1996 337 349
59. M.I. Choudhary, Azizuddin, and Atta-ur-Rehman Microbial transformation of danazol Nat Prod Lett 16 2002 101 106
60. J.R. Hanson, H. Nasir, and A. Pervez The hydroxylation of testosterone and some derivatives by Cephalosporium aphidicola Phytochemistry 42 1996 411 415
61. Atta-ur-Rehman, M.I. Choudhary, F. Asif, A. Farooq, and M. Yaqoob Microbial transformations of testosterone Nat Prod Lett 12 1998 255 261
62. A. Farooq, and S. Tahara Biotransformation of testosterone J Nat Prod 63 2000 489 491
63. S. Al-Awadi, M. Afzal, and S. Oommen Studies of Bacillus stearothermophilus. Part III. Transformation of testosterone Appl Microbiol Biotechnol 62 2003 48 52
64. K.M. Madyastha Novel microbial transformations of steroids Adv Exp Med Biol 405 1995 259 270
65. B. Angelova, S. Mutafov, T. Avramova, I. Dimova, and L. Boyadjieva 9α-Hydroxylation of 4-androstene-3,17-dione by resting Rhodococcus sp. cells Process Biochem 31 1996 179 184
66. O. Schaaaf, and K. Dettner Transformation of steroids by Bacillus strains isolated from the forefut of water beetles (Coleoptera: Dytiscidae): 1. Metabolism of androst-4-en-3,17-dione (AD) J Steroid Biochem Mol Biol 67 1998 451 465
67. M.I. Choudhary, S. Sultanl, M.T.H. Khan, A. Yasin, F. Shaheen, and Atta-ur-Rehman Biotransformation of (+)-androst-4-ene-3, 17-dione Nat Prod Res 18 2004 529 535
68. Z. Xiong, Q. Wei, H. Chen, S. Chen, W. Xu, and Liang G.S. Qiu Microbial transformation of androst-4-ene-3, 17-dione by Beauveria bassiana Steroids 71 2006 979 983
69. M.I. Choudhary, S.G. Musharraf, F. Shaheen, and Atta-ur-Rehman Microbial transformation of (+)-androsta-1, 4-diene-3, 17-dione by Cephalosporium aphidicola Nat Prod Lett 16 2002 377 382
70. M.I. Choudhary, S.A.A. Shah, S.G. Musharraf, F. Shaheen, and Atta-ur-Rehman Microbial transformation of dehydroepiandrosterone Nat Prod Res 17 2003 215 220
71. S.B. Mahato, and I. Mujumdar Current trends in microbial steroid biotransformation Phytochemistry 34 1993 883 898
72. D.C. Nonhebel The chemistry of cyclopropylmethyl and related radicals Chem Soc Rev 22 1993 347 359
73. C.S. Bensasson, J.R. Hanson, and Y.L. Huerou The microbiological hydroxylation of 3α,5-cycloandrostanes by Cephalosporium aphidicola Phytochemistry 52 1999 1279 1282
74. H.L. Holland The mechanism of the microbial hydroxylation of steroids Chem Soc Rev 11 1982 371 395
75. Hanson JR, Kiran I. The microbiological hydroxylation of 17-chloroandrosta-4,16-dien-3-one by Cephalosporium aphidicola. J Chem Res 2003; 130-1.
76. M.I. Choudhary, S. Sultan, M.T.H. Khan, and Atta-ur-Rehman Microbial transformation of 17α-ethynyl- and 17α-ethylsteroids and tyrosinase inhibitory activity of transformed products Steroids 70 2005 798 802
77. M. Yashihama, K. Tamura, M. Nakakoshi, J. Nakamura, N. Fujise, and G. Kawanishe 14 alpha-Hydroxyandrost-4-ene-3,6,17-trione as a mechanical-based irreversible inhibitor of estrogen biosynthesis Chem Pharm Bull 38 1990 2834 2837
78. T. Matsumoto, A.M. Nakamura, K. Mori, I. Akiyama, H. Hirose, and Y. Takahashi Gland of the pulmonate snail Lymnaea stagnalis Gen Comp Endocrinol 151 2007 195 201
79. S.G. Musharraf, Atta-ur-Rehman, M.I. Choudhary, and S. Sultan Microbial transformation of (+)-adrenosterone Nat Prod Lett 16 2002 345 349
80. M.I. Choudhary, S. Sultan, S. Jalil, S. Anjum, A.A. Rahman, H.K. Fun, and Atta-ur-Rehman Microbial transformation of mesterolone Chem Biodivers 2 2005 392 400
81. M.I. Choudhary, S.G. Musharraf, Z.A. Siddiqui, N.T. Khan, R.A. Ali, and Atta-ur-Rehman Microbial transformation of mestranol by Cunninghamella elegans Chem Pharm Bull 53 2005 1011 1013
82. Choudhary MI, Musharraf SG, Ali RA, Atif M, Atta-ur-Rehman. Microbial transformation of antifertility agents, norethisterone nad 17α- ethylnylestradiol. Z Naturforsch 2004; 59B: 319-23.
83. M.I. Choudhary, S.A. Shah, Atta-ur-Rahman, S.N. Khan, and M.T. Khan Steroids 75 2010 956 966
84. M.A. Faramarzi, M.T. Yazdi, A. Shafiee, and G. Zarrini Microbial transformation of hydrocortisone by Acremonium strictum PTCC 5282 Steroids 67 2002 869 872
85. Hardman JG, Limbird LE, Gilam AG. The pharmacological basis of therapeutics. Medicinal Publishing Division, New York; 2001. p. 733.
86. M.I. Choudhary, Z.A. Siddiqui, S.G. Musharraf, S.A. Nawaz, and Atta-ur-Rehman Microbial transformation of prednisone Nat Prod Res 19 2005 311 317
87. M.I. Choudhary, S. Sultan, M. Yaqoob, S.G. Musharraf, A. Yasin, F. Shaheen, and Atta-ur-Rehman Microbial transformation of cortisol and prolyl endopeptidase inhibitory activities of its transformed products Nat Prod Res 17 2003 389 395
88. I. Kiran, J.R. Hanson, and A.C. Hunter The microbiological hydroxylation of some methoxysteroids by Cephalosporium aphidicola J Chem Res 5 2004 362 363
89. T. Hung, H. Stuppner, E.P. Ellmerer-Muller, D. Scholz, D. Eigner, and M.P. Manandhar Steroids and terpenoids from the gum resin of Ailanthus grandis Phytochemistry 39 1995 1403 1409
90. Marg KSK. The Wealth of India, National Institute of Science Communication, vol. 2. CSIR, New Delhi; 2001. p. 162.
91. J. Malikova, J. Swaczynova, Z. Kolar, and M. Strnad Anticancer and antiproliferative activity of natural Brassinosteroids Phytochemistry 69 2008 418 426
92. Atta-ur-Rehman, M.I. Choudhary, F. Shaheen, M. Ashraf, and S. Jahan Microbial transformations of hypolipemic E-guggulsterone J Nat Prod 61 1998 428 431
93. M.I. Choudhary, S.A.A. Shah, A. Sami, A. Ajaz, F. Shaheen, and Atta-ur-Rehman Fungal metabolites of (E)-guggulsterone and their antibacterial and radical scavenging activities Chem Biodivers 2 2005 516 524
94. A. Jekkel, E. Ilky, G. Horváth, I. Pallagi, J. Süt, and G. Ambrus Microbial hydroxylation of 13β-ethyl-4-gonene-3, 17-dione J Mol Catal B 5 1998 385 387
95. R.M. Weier, and L.F. Hofmann Synthesis and antimineralocorticoid activities of some 6-substituted 7α-carboalkoxy steroidal spirolactones J Med Chem 20 1977 1304 1308
96. C.L. Preisig, J.A. Laakso, U.M. Mocek, P.T. Wang, J. Baez, and G. Byng Biotransformations of the cardiovascular drugs mexrenone and canrenone J Nat Prod 66 2003 350 356
97. M.D. Antoun, D. Abramson, L.R. Tyson, C. Chang-jer, J.L. MacLaughlin, and G. Peck Potential antitumor agents. XVII. Physalin B and 25,26- epidihydrophysalin C from Witheringia coccoloboides J Nat Prod 44 1981 579 584
98. M.B.P. Soares, M.C. Bellintani, M.I. Ribeiro, T.C. Tomassini, and D.S.R. Ribeiro Inhibition of macrophage activation and lipopolysaccharide-induced death by seco-steroids purified from Physalis angulata L. Eur J Pharmacol 459 2003 107 112
99. R.C. Pietro, S.D. Kashima, N. Sato, A.H. Januario, and S.C. Franca In vitro antimycobacterial activities of Physalis angulata L. Phytomedicines 7 2000 335 338
100. R.D. Budhiraja, K.N. Garg, S. Sudhir, and B. Arora Protective effect of 3-ss-hydroxy-2,3-dihydrowithanolide F against CCl4-induced hepatotoxicity Planta Med 52 1986 28 32
101. E. Glotter Withanolides and related ergostane-type steroids Nat Prod Rep 8 1991 415 440
102. M.I. Choudhary, S. Yousaf, Samreen, S.A.A. Shah, S. Ahmad, and Atta-ur-Rehman Biotransformation of physalin H and leishmanicidal activity of its transformed products Chem Pharm Bull 54 2006 927 930
103. L. Krenn, and B. Kopp Bufadienolides from animal and plant sources Phytochemistry 48 1998 1 29
104. P.S. Steyn, and F.R. Van Heerden Bufadienolides of plant and animal origin Nat Prod Rep 15 1998 397 413
105. T. Nogawa, Y. Kamano, A. Yamashita, and G.R. Pettit Isolation and structure of five new cancer cell growth inhibitory bufadienolides from the Chinese traditional drug Ch, an Su J Nat Prod 64 2001 1148 1152
106. M. Ye, G.Q. Qu, H.Z. Guo, and D.A. Guo Specific 12β-hydroxylation of cinobufagin by filamentous fungi Appl Environ Microbiol 70 2004 3521 3527
107. A. William, A. Ricke, Y. Wang, and R. Gerald Smooth muscle differentiation and patterning in the urinary bladder Differentiation 75 2007 871 882
108. M. Ye, G. Qu, H. Guo, and D. Guo Novel cytotoxic bufadienolides derived from bufalin by microbial hydroxylation and their structure-activity relationships J Steroid Biochem Mol Biol 91 2004 87 98
109. M. Ye, J. Han, G. Tu, D. An, and D. Guo Microbial hydroxylation of bufalin by Cunninghamella blakesleana and Mucor spinosus J Nat Prod 68 2005 628
110. L. Krenn, and B. Kopp Bufadienolides from animal and plant sources Phytochemistry 48 1998 1 29
111. J.T. Xie, H.S. Wang, A.S. Attele, and C.S. Yuan Effect of resibufogenin from toad venom on isolated purkinje fibres Am J Chin Med 28 2000 187 196
112. J.T. Xie, L. Dey, J.A. Wu, T.K. Lowell, and C.S. Yuan Cardiac toxicity of resibufogenin: electrophysiological evidence Acta Pharmacol Sin 22 2001 289 297
113. Y. Kamano, A. Kotaki, H. Hashima, M. Inoue, H. Morita, and K. Takeya Structure-toxicity relationship for the toad poison bufadienolides Bioorg Med Chem 6 1998 1103 1115
114. P. Terness, D. Novalon, C. Dufter, B. Kopp, and G. Opelz The T-cell suppressive effect of bufadienolides: structural requirements for the immunoregulatory activity Int Immunopharmacol 1 2001 119 134
115. W. Zhang, M. Ye, G.Q. Qu, W.Y. Wu, Y.J. Chin, and D.A. Guo Microbial hydroxylation of cinobufagin by Mucor spinosus J Asian Nat Prod Res 7 2005 225 229