Callystatin a, a potent cytotoxic polyketide from the marine sponge, callyspongia truncata

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2859-2862

  Kobayashi, Motomasa ^a   Higuchi, Kouichi ^a   Murakami, Nobutoshi ^a   Tajima, Hisashi ^a   Aoki, Shunji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; POLYKETIDE;

ANIMAL TISSUE; ARTICLE; CELL STRAIN KB; CONTROLLED STUDY; CYTOTOXICITY; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE;

EID: 0030969012     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00482-6     Document Type: Article

References (18)

1. a) Kobayashi, M.; Wang, W.; Ohyabu, N.; Kurosu, M.; Kitagawa, I. Chem. Pharm. Bull., 1995, 43, 1598-1600.
2. b) Kobayashi, M.; Aoki, S.; Gato, K.; Kitagawa, I. Chem. Pharm. Bull., 1996, 44, 2142-2149 and preceding papers.
3. Kusumi, T.; Ohtani, I.; Inoue, M.; Kakisawa, H. Tetrahedron Lett., 1988, 29, 4731-4734.
4. 3, δ); 5.13 (br d, J=9.9 Hz, H-15), 3.55 (dq, J=9.9, 6.6, H-16), 3.00 (qd, J=7.1, 4.3, H-18), 5.49 (dd, J=6.6, 4.3, H-19), 1.43 (m, H-20), 1.27 (m, H-21), 0.80 (t, J=7.3, H-22), 1.82 (d, J=1.2, H-26), 1.13 (d, J=6.6, H-27), 1.01 (d, J=7.1, H-28), 0.69 (d, J=6.4, H-29).
5. 3, δ); 5.11 (br d, J=9.9 Hz, H-15), 3.53 (dq, J=9.9, 6.6, H-16), 2.98 (qd, J=7.1, 4.3, H-18), 5.50 (dd, J=6.6, 4.3, H-19), 1.46 (m, H-20), 1.28 (m, H-21), 0.80 (t, J=7.3, H-22), 1.81 (d, J=1.2, H-26), 1.11 (d, J=6.6, H-27), 0.95 (d, J=7.1, H-28), 0.74 (d, J=6.4, H-29).
6. Uotani, K.; Naganawa, H.; Kondo, S.; Aoyagi, T.; Umezawa, H. J. Antibiotics, 1982, 35, 1495-1499.
7. Paterson, I.; Hulme, A. N. J. Org. Chem., 1995, 60, 3288-3300.
8. a) Anteunis, M. J. O. Bioorg. Chem., 1976, 5, 327-337.
9. b) Manker, D. C.; Faulkner, D. J.; Stout, T. J.; Clardy, J. J. Org. Chem., 1989, 54, 5371-5374.
10. c) Blanchfield, J. T.; Brecknell, D. J.; Brereton, I. M.; Garson, M. J.; Jones, D. P. Aust J. Chem., 1994, 47, 2255-2269.
11. 6) of 4 and 5 are assigned as follows. 4: δ 2.84 (qd, J= 7.3, 2.3 Hz, 10-H), 3.49 (dt, J=8.9, 2.3 Hz, 11-H), 1.47-1.40 (m, 12-H); δc 217.7 (9-C), 44.9 (10-C). 5: δ 2.86 (qd, J= 7.1, 4.1 Hz, 10-H), 3.59-3.53 (m, 11-H), 1.44-1.32 (2H, m, 12-H); δc 216.9 (9-C), 45.7 (10-C).
12. a) Hamamoto, T.; Seto, H.; Beppu, T. J. Antibiotics, 1983, 36, 646-650.
13. b) Hurley, T. R.; Bunge, R. H.; Willer, N. E.; Hokanson, G. C.; French, J. C. J. Antibiotics, 1986, 39, 1651-1656.
14. Schaumberg, J. P.; Hokanson, G. C.; French, J. C. J. Chem. Soc. Chem. Commun., 1984, 1450-1452.
15. Komiyama, K.; Okada, K.; Oka, H.; Tomisaka, S.; Miyano, T.; Funayama, S. Umezawa, I.; J. Antibiotics, 1985, 38, 220-223.
16. a) Hayakawa, Y.; Adachi, K.; Komeshima, N. J. Antibiotics, 1987, 40, 1349-1352.
17. b) Hayakawa, Y.; Sohda, K.; Shin-ya, K.; Hidaka, T.; Seto H. J. Antibiotics, 1995, 48, 954-961.
18. Hayakawa, Y.; Sohda, K.; Seto H. J. Antibiotics, 1996, 49, 980-984.