Halichlorine, an inhibitor of VCAM-1 induction from the marine sponge Halichondria okadai Kadota

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3867-3870

  Kuramoto, Makoto ^a   Tong, Chou ^b   Yamada, Kaoru ^b   Chiba, Tatsuhiko ^a   Hayashi, Yoshinori ^a   Uemura, Daisuke ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; HALICHLORINE; UNCLASSIFIED DRUG; VASCULAR CELL ADHESION MOLECULE 1;

ANGINA PECTORIS; ARTICLE; ATHEROSCLEROSIS; CORONARY ARTERY DISEASE; DRUG ISOLATION; DRUG STRUCTURE; ENDOTHELIUM CELL; HUMAN; HUMAN CELL; INFLAMMATION; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; SPONGE (PORIFERA); STEREOCHEMISTRY; UMBILICAL VEIN;

EID: 0029942922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00703-4     Document Type: Article

References (14)

1. Uemura, D.; Hirata, Y. In Studies in Natural Products Chemistry, Vol. 5, Part B, Rahman, A.-U. Ed; Elsevier; Amsterdam, 1989; pp. 377-401.
2. Uemura, D. In Bioorganic Marine Chemistry, Vol.4; Scheuer, P. J. Ed; Springer; Berlin, Heidelberg, New York, 1991; pp. 1-31
3. Uemura, D.; Takahashi, K., Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc., 1985, 107, 4796.
4. Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.-H.; Cheng, H.-S. J. Am. Chem. Soc., 1995, 117, 1155.
5. Halichondria okadai contains okadaic acid, a potent inhibitor of protein phosphatase 1 and 2A and halichondnns, which are antitumor agents that are in phase 1 clinical testing.
6. Osborn, L.; Hession, C., Tizard, R.; Vassallo, C.; Huhovoskyi, S.; Chi-Rosso, G.; Hobb, R. Cell, 1988, 59, 1203.
7. Kock, A. E., Halloran, M. M.; Haskell, C. J.; Sah, M. R.; Polverini, P. J. Nature, 1995, 376, 517 and references cited therein . Although activity of halichlorine is not so potent [Boschelli, D. H.; Karmer, J. B.; Khatana, S. S.; Sorenson, R. J.; Connor, D. T.; Ferin, M. A., Wright, C. D.; Lesch, M. E.; Imre, K.; Okonkwo, G. C.; Schrie D. J.; Conroy, M. C.; Ferguson, E.; Woelle, J.; Saxena, U. J. Med. Chem., 1995, 38, 4597.], specificity against VCAM-1 is observed, interstingly. Our bioassay and detailed data procedure will be reported elsewhere.
8. Kock, A. E., Halloran, M. M.; Haskell, C. J.; Sah, M. R.; Polverini, P. J. Nature, 1995, 376, 517 and references cited therein . Although activity of halichlorine is not so potent [Boschelli, D. H.; Karmer, J. B.; Khatana, S. S.; Sorenson, R. J.; Connor, D. T.; Ferin, M. A., Wright, C. D.; Lesch, M. E.; Imre, K.; Okonkwo, G. C.; Schrie D. J.; Conroy, M. C.; Ferguson, E.; Woelle, J.; Saxena, U. J. Med. Chem., 1995, 38, 4597.], specificity against VCAM-1 is observed, interstingly. Our bioassay and detailed data procedure will be reported elsewhere.
9. Mass spectra were measured on a JMS-AX500 mass spectrometer.
10. 1H NMR of p-bromobenzoate, δ 6.16 (1H, ddd, J= 16.9, 7.7. 1.5 Hz, H15). 5.72 (1H, ddd, J= 16.9, 5.1, 1.0 Hz, H16), 6.69 (1H, ddd, J= 8.1, 5.1, 1.5 Hz, H17), 5.65 (1H, dd, J= 8.1, 1.1 Hz, H18).
11. Breitmaier, E.; Volter, W. Carbon-13 NMR Spectroscopy, VCH: Weinheim, New York, 1990; pp. 198-206.
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14. Chou, T.; Kuramoto, M.; Ohtani, Y., Shikano, M.; Yazawa, K., Uemura, D. Tetrahedron Lett., this issue.