Novel mammalian cell cycle inhibitors, cyclotryprostatins A-D, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase

Tetrahedron

Volumn 53, Issue 1, 1997, Pages 59-72

  Cui, Cheng Bin ^a   Kakeya, Hideaki ^a   Osada, Hiroyuki ^a  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOTRYPROSTATIN A; CYCLOTRYPROSTATIN B; CYCLOTRYPROSTATIN C; CYCLOTRYPROSTATIN D; CYTOTOXIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPERGILLUS; CELL CYCLE; CELL PROLIFERATION; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0031060189     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)00978-7     Document Type: Article

References (16)

1. Osada, H.; Cui, C.-B.; Onose, R.; Hanaoka, F. Bioorg. Med. Chem., 1996, in press.
2. Cui, C.-B.; Kakeya, H.; Okada, G.; Onose, R.; Ubukata, M.; Takahashi, I.; Isono, K.; Osada, H. J. Antibiot., 1995, 48, 1382-1384.
3. Cui, C.-B.; Ubukata, M.; Kakeya, H.; Onose, R.; Okada, G.; Takahashi, I.; Isono, K.; Osada, H. J. Antibiot., 1996, 49, 216-219.
4. Cui, C.-B.; Kakeya, H.; Okada, G.; Onose, R.; Osada, H. J. Antibiot., 1996, 49, 527-533.
5. Cui, C.-B.; Kakeya, H.; Osada, H. J. Antibiot., 1996, 49, 534-540.
6. Cui, C.-B.; Kakeya, H.; Osada, H. J. Antibiot., 1996, 49, 832-835.
7. Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron, 1996, 52, 12651-12666.
8. In the UV spectra, both the 6-O-methylindole and the indole chromophores show a strong absorption in the 220-230 nm region. While in the 250-320 nm region, two major absorption bands like the humps of a camel are typical of the 6-O-methylindole chromophore and the appearance of a major one in the same region is characteristic for the indole chromophore, respectively (cf. reference 2 and see Cole, R. J.; Cox, R. H. Handbook of Toxic Fungal Metabolites, Academic Press Inc.: New York, 1981; pp. 357-383 for the 6-O-methylindole chromophore, pp. 390 and pp. 453-462 for the indole chromophore).
9. Fayos, J.; Lokensgard, D.; Clardy, J.; Cole, R. J.; Kirksey, J. W. J. Am. Chem. Soc., 1974, 96, 6785-6787.
10. Steyn, P. S. Tetrahedron, 1973, 29, 107-120.
11. Steyn, P. S. Tetrahedron Lett., 1971, 3331-3334.
12. Steyn, P. S.; Vleggaar, R. Progress in the Chemistry of Organic Natural Products (Founded by Zechmiester, L.; Edited by Herz, W.; Grisebach, H.; Kirby, G. W.), 1985, 48, 1-80.
13. Abaraham, W.-R.; Arfmann, H.-A. Phytochem., 1990, 29, 1025-1026.
14. Yamazaki, M.; Fujimoto, H.; kawasaki, T. Chem. Pharm. Bull., 1980, 28, 245-254.
15. Cole, R. J.; Cox, R. H. Handbook of Toxic Fungal Metabolites, Academic Press Inc.: New York, 1981; pp. 355-385.
16. Kodato et al have recorded that in a mixture of the synthetic mediates for fumitremorgin B, the presence of a 13-ketocarbonyl compound having the same structural skeleton as that in 4 was revealed by the UV absorption at 294.5, 269.5 and 308 nm, corresponding to the 3-acylindole chromophore, in the UV spectrum of the mixture in an EtOH solution. But they did not isolate the compound in a pure form. Kodato, S.; Nakagawa, M.; Hongu, M.; Kawata, T.; Hino, T. Tetrahedron, 1988, 44, 359-377.