Chemistry of antitumor isoquinolinequinone alkaloids: Unexpected oxidative degradation of saframycin S to generate simple isoquinoline alkaloids, mimosamycin and mimocin

Heterocycles

Volumn 61, Issue , 2003, Pages 79-86

  Saito, Naoki ^a   Koizumi, Yu Ichi ^a   Tanaka, Chieko ^a   Suwanborirux, Khanit ^b   Amnuoypol, Surattana ^b   Kubo, Akinori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

^b CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ISOQUINOLINE ALKALOID; ISOQUINOLINEQUINONE ALKALOID DERIVATIVE; MIMOCIN; MIMOSAMYCIN; SAFRAMYCIN S; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; STRUCTURE ANALYSIS;

EID: 0345761291     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-03-S45     Document Type: Article

References (54)

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2. Dedicated also to Professor Norio Aimi (Chiba University) on the occasion of his 65th birthday.
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23. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
24. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
25. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
26. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
27. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
28. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
29. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
30. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
31. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
32. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
33. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
34. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
35. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
36. Isolation and structure determination of mimosamycin from Streptomyces lavendulae: a) T. Arai, K. Yazawa, Y. Mikami, A. Kubo, and K. Takahashi, J. Antibiot., 1976, 29, 398; Y. Mikami, K. Yokoyama, A. Omi, and T. Arai, J. Antibiot., 1976, 29, 408; H. Fukumi, F. Maruyama, K. Yoshida, M. Arai, A. Kubo, and T. Arai, J. Antibiot., 1978, 31, 847; T. Hata, H. Fukumi, S. Sato, K. Aiba, and C. Tamura, Acta Crystallog. Sec. B., 1978, B34, 2899; Mimosamycin and related compounds have also been identified in marine organisms, see: J. M. Frincke and D. J. Faulkner, J. Am. Chem. Soc., 1982, 104, 265; T. C. Makee and C. M. Ireland, J. Nat. Prod., 1987, 50, 754; H. He and D. J. Faulkner, J. Org. Chem., 1989, 54, 5822; B. S. Davidson, Tetrahedron Lett., 1992, 33, 3721; G. R. Pettit, J. C. Collins, D. L. Herald, D. L. Doubek, M. R. Boyd, J. M. Schmidt, J. N. A. Hooper, and L. P. Tackett, Can. J. Ches., 1992, 70, 1170; Y. Venkateswarlu, M. V. R. Reddy, K. V. N. S. Srinivas, and J. V. Rao, Indian J. Chem., Sect. B, 1993, 32B, 704; M. Kobayashi, S. R. Rao, R. Chavakula, and N. S. Sarma, J. Chem. Res., 1994, 282; R. A. Edrada, P. Proksch, V. Wray, R. Christ, L. Witte, R. and W. M. Van Soest, J. Nat. Prod., 1996, 59, 973; P. S. Parameswaran, C. G. Naik, S. Y. Kamat, and B. N. Pramanik, Indian J. Chem., Sect. B, 1998, 37B, 1258; P. Ramesh, N. S. Reddy, and Y. Venkateswarlu, J. Nat. Prod., 1999, 62, 780; M. A. Rashid, K. R. Gustafson, and M. R. Boyd, J. Nat. Prod., 2001, 64, 1249.
37. b) Isolation of mimocin: A. Kubo, S. Nakahara, R. Iwata, K. Takahashi, and T. Arai, Tetrahedron Lett., 1980, 21, 3207.
38. Total synthesis of mimosamycin, see: a) H. Fukumi, H. Kurihara, T. Hata, C. Tamura, A. Kubo, and T. Arai, Tetrahedron Lett., 1977, 3825; H. Fukumi, H. Kurihara, and H. Mishima, Chem. Pharm. Bull., 1978, 26, 2175.
39. Total synthesis of mimosamycin, see: a) H. Fukumi, H. Kurihara, T. Hata, C. Tamura, A. Kubo, and T. Arai, Tetrahedron Lett., 1977, 3825; H. Fukumi, H. Kurihara, and H. Mishima, Chem. Pharm. Bull., 1978, 26, 2175.
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42. d) B. Keteleyn and N. D. Kimpe, J. Org. Chem., 2000, 65, 635.
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52. 4: 292.1423. Found: 292.1419.
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54. In the chemistry of quinocarcin A, a unified mechanism for this type of redox self-disproportionation was reported by Professor Williams, see: R. M. Williams, T. Glinka, M. E. Flanagam, R. Gallegos, H. Coffman, and D. Pei, J. Am. Chem. Soc., 1992, 114, 733.