Asperazine, a Selective Cytotoxic Alkaloid from a Sponge-Derived Culture of Aspergillus niger

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7078-7079

  Varoglu, Mustafa ^a   Corbett, Thomas H ^b   Valeriote, Frederick A ^b   Crews, Phillip ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000260530     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970568z     Document Type: Article

References (39)

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11. Examples include: chlorocarolides [(a) Abrell, L. M.; Borgeson, B.; Crews, P. Tetrahedron Lett. 1996, 37, 2331-2334], chloriolins [(b) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348], nectriapyrones [(c) Abrell, L. M.; Cheng, X.-C.; Crews, P. Tetrahedron Lett. 1994, 35, 9159-9160], secocurvalarin [(d) Abrell, L. M.; Borgeson, B. M.; Crews, P. Tetrahedron Lett. 1996, 37, 8983-8984], trichohrazin [(e) Kobayashi, M.; Uehara, H.; Matsunami, K.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 7925-7928].
12. Examples include: chlorocarolides [(a) Abrell, L. M.; Borgeson, B.; Crews, P. Tetrahedron Lett. 1996, 37, 2331-2334], chloriolins [(b) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348], nectriapyrones [(c) Abrell, L. M.; Cheng, X.-C.; Crews, P. Tetrahedron Lett. 1994, 35, 9159-9160], secocurvalarin [(d) Abrell, L. M.; Borgeson, B. M.; Crews, P. Tetrahedron Lett. 1996, 37, 8983-8984], trichohrazin [(e) Kobayashi, M.; Uehara, H.; Matsunami, K.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 7925-7928].
13. Examples include: chlorocarolides [(a) Abrell, L. M.; Borgeson, B.; Crews, P. Tetrahedron Lett. 1996, 37, 2331-2334], chloriolins [(b) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348], nectriapyrones [(c) Abrell, L. M.; Cheng, X.-C.; Crews, P. Tetrahedron Lett. 1994, 35, 9159-9160], secocurvalarin [(d) Abrell, L. M.; Borgeson, B. M.; Crews, P. Tetrahedron Lett. 1996, 37, 8983-8984], trichohrazin [(e) Kobayashi, M.; Uehara, H.; Matsunami, K.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 7925-7928].
14. Examples include: chlorocarolides [(a) Abrell, L. M.; Borgeson, B.; Crews, P. Tetrahedron Lett. 1996, 37, 2331-2334], chloriolins [(b) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348], nectriapyrones [(c) Abrell, L. M.; Cheng, X.-C.; Crews, P. Tetrahedron Lett. 1994, 35, 9159-9160], secocurvalarin [(d) Abrell, L. M.; Borgeson, B. M.; Crews, P. Tetrahedron Lett. 1996, 37, 8983-8984], trichohrazin [(e) Kobayashi, M.; Uehara, H.; Matsunami, K.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 7925-7928].
15. Examples include: chlorocarolides [(a) Abrell, L. M.; Borgeson, B.; Crews, P. Tetrahedron Lett. 1996, 37, 2331-2334], chloriolins [(b) Cheng, X.-C.; Varoglu, M.; Abrell, L.; Crews, P.; Lobkovsky, E.; Clardy, J. J. Org. Chem. 1994, 59, 6344-6348], nectriapyrones [(c) Abrell, L. M.; Cheng, X.-C.; Crews, P. Tetrahedron Lett. 1994, 35, 9159-9160], secocurvalarin [(d) Abrell, L. M.; Borgeson, B. M.; Crews, P. Tetrahedron Lett. 1996, 37, 8983-8984], trichohrazin [(e) Kobayashi, M.; Uehara, H.; Matsunami, K.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1993, 34, 7925-7928].
16. Examples include: marine-derived leptosins [(a) Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Ito, Y.; Matsumura, E.; Tanaka, H. Phytochemistry 1995, 38, 155-158. (b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron 1995, 51, 3483-3498] which strongly resemble terrestrial fungal compounds: chaetocin A [(c) Hauser, D.; Weber, H. P.; Sigg, H. P. Helv. Chim. Acta. 1970, 53, 1061-1073], verticillin A [(d) Minato, H; Matsumoto, M.; Katayama, T. J. Chem. Soc. Perk. Trans. I 1973, 1819-1825] and the melinacidins III and IV from both a marine [(e) Furuya, K.; Okudaira, M.; Shindo, T.; Sato, A. Sankyo Kenkyusho Nempo 1985, 37, 140-142] and a terrestrial fungi [(f) Argoudelis, A. D.; Mizsak, S. A. J. Antibiot. 1977, 30, 468].
17. Examples include: marine-derived leptosins [(a) Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Ito, Y.; Matsumura, E.; Tanaka, H. Phytochemistry 1995, 38, 155-158. (b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron 1995, 51, 3483-3498] which strongly resemble terrestrial fungal compounds: chaetocin A [(c) Hauser, D.; Weber, H. P.; Sigg, H. P. Helv. Chim. Acta. 1970, 53, 1061-1073], verticillin A [(d) Minato, H; Matsumoto, M.; Katayama, T. J. Chem. Soc. Perk. Trans. I 1973, 1819-1825] and the melinacidins III and IV from both a marine [(e) Furuya, K.; Okudaira, M.; Shindo, T.; Sato, A. Sankyo Kenkyusho Nempo 1985, 37, 140-142] and a terrestrial fungi [(f) Argoudelis, A. D.; Mizsak, S. A. J. Antibiot. 1977, 30, 468].
18. Examples include: marine-derived leptosins [(a) Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Ito, Y.; Matsumura, E.; Tanaka, H. Phytochemistry 1995, 38, 155-158. (b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron 1995, 51, 3483-3498] which strongly resemble terrestrial fungal compounds: chaetocin A [(c) Hauser, D.; Weber, H. P.; Sigg, H. P. Helv. Chim. Acta. 1970, 53, 1061-1073], verticillin A [(d) Minato, H; Matsumoto, M.; Katayama, T. J. Chem. Soc. Perk. Trans. I 1973, 1819-1825] and the melinacidins III and IV from both a marine [(e) Furuya, K.; Okudaira, M.; Shindo, T.; Sato, A. Sankyo Kenkyusho Nempo 1985, 37, 140-142] and a terrestrial fungi [(f) Argoudelis, A. D.; Mizsak, S. A. J. Antibiot. 1977, 30, 468].
19. Examples include: marine-derived leptosins [(a) Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Ito, Y.; Matsumura, E.; Tanaka, H. Phytochemistry 1995, 38, 155-158. (b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron 1995, 51, 3483-3498] which strongly resemble terrestrial fungal compounds: chaetocin A [(c) Hauser, D.; Weber, H. P.; Sigg, H. P. Helv. Chim. Acta. 1970, 53, 1061-1073], verticillin A [(d) Minato, H; Matsumoto, M.; Katayama, T. J. Chem. Soc. Perk. Trans. I 1973, 1819-1825] and the melinacidins III and IV from both a marine [(e) Furuya, K.; Okudaira, M.; Shindo, T.; Sato, A. Sankyo Kenkyusho Nempo 1985, 37, 140-142] and a terrestrial fungi [(f) Argoudelis, A. D.; Mizsak, S. A. J. Antibiot. 1977, 30, 468].
20. Examples include: marine-derived leptosins [(a) Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Ito, Y.; Matsumura, E.; Tanaka, H. Phytochemistry 1995, 38, 155-158. (b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron 1995, 51, 3483-3498] which strongly resemble terrestrial fungal compounds: chaetocin A [(c) Hauser, D.; Weber, H. P.; Sigg, H. P. Helv. Chim. Acta. 1970, 53, 1061-1073], verticillin A [(d) Minato, H; Matsumoto, M.; Katayama, T. J. Chem. Soc. Perk. Trans. I 1973, 1819-1825] and the melinacidins III and IV from both a marine [(e) Furuya, K.; Okudaira, M.; Shindo, T.; Sato, A. Sankyo Kenkyusho Nempo 1985, 37, 140-142] and a terrestrial fungi [(f) Argoudelis, A. D.; Mizsak, S. A. J. Antibiot. 1977, 30, 468].
21. Examples include: marine-derived leptosins [(a) Takahashi, C.; Takai, Y.; Kimura, Y.; Numata, A.; Shigematsu, N.; Ito, Y.; Matsumura, E.; Tanaka, H. Phytochemistry 1995, 38, 155-158. (b) Takahashi, C.; Minoura, K.; Yamada, T.; Numata, A.; Kushida, K.; Shingu, T.; Hagishita, S.; Nakai, H.; Sato, T.; Harada, H. Tetrahedron 1995, 51, 3483-3498] which strongly resemble terrestrial fungal compounds: chaetocin A [(c) Hauser, D.; Weber, H. P.; Sigg, H. P. Helv. Chim. Acta. 1970, 53, 1061-1073], verticillin A [(d) Minato, H; Matsumoto, M.; Katayama, T. J. Chem. Soc. Perk. Trans. I 1973, 1819-1825] and the melinacidins III and IV from both a marine [(e) Furuya, K.; Okudaira, M.; Shindo, T.; Sato, A. Sankyo Kenkyusho Nempo 1985, 37, 140-142] and a terrestrial fungi [(f) Argoudelis, A. D.; Mizsak, S. A. J. Antibiot. 1977, 30, 468].
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