Isolation and structure of prorocentrolide B, a fast-acting toxin from Prorocentrum maculosum

Journal of Natural Products

Volumn 59, Issue 11, 1996, Pages 1010-1014

  Hu, Tingmo ^a   DeFreitas, Anthony S W ^a   Curtis, Jonathan M ^a   Oshima, Yasukatsu ^b   Walter, John A ^a   Wright, Jeffrey L C ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PROROCENTROLIDE B; TOXIN; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; DIARRHEA; DINOFLAGELLATE; DRUG ISOLATION; DRUG STRUCTURE; INTOXICATION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SHELLFISH; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ANIMALS; CARBOHYDRATE SEQUENCE; DINOFLAGELLIDA; FEMALE; MAGNETIC RESONANCE SPECTROSCOPY; MARINE TOXINS; MASS SPECTROMETRY; MICE; MOLECULAR SEQUENCE DATA; PYRANS;

DINOPHYCEAE; PROROCENTRUM LIMA; PROROCENTRUM MACULOSUM;

EID: 0029963727     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np960439y     Document Type: Article

References (19)

1. Yasumoto, T.; Oshima, Y.; Sugawara, W.; Fukuyo, Y.; Oguri, H.; Igarishi, T.; Fujita, N. Bull. Jpn. Soc. Sci. Fish. 1980, 46, 1405-1411.
2. Lee, J. S.; Igarishi, T.; Fraga, S.; Dabi, E.; Hovgaard, P.; Yasumoto, T. J. Appl. Phycol. 1989, 1, 147-152.
3. Dickey, R. W.; Bobzin, S. C.; Faulkner, D. J.; Bencsath F. A.; Andrzejewski, D. Toxicon 1990, 28, 371-377.
4. For a review, see Cohen P.; Holmes, C. F. B.; Sukitani, Y. Trends Biol. Sci. 1990, 15, 98.
5. Tindall, D. R.; Dickey, R. W.; Carlson, R. D.; Morey-Gaines, G. In Seafood Toxins; Ragelis, E. P., Ed.; ACS Symposium Series 262; American Chemical Society: Washington DC, 1984; pp 225-240.
6. Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.; Chen, H. J. Am. Chem. Soc. 1995, 117, 1155-1156.
7. Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H. F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096.
8. Hu, T.; Curtis, J. M.; Oshima, Y.; Quilliam, M. A.; Walter, J. A.; Watson-Wright, W.; Wright, J. L. C. J. Chem. Soc., Chem. Commun. 1995, 2159-2161.
9. Originally referred to as Prorocentrum concavum Fukuyo; Hu, T.; Marr, J.; deFreitas, A. S. W.; Quilliam, M. A.; Walter, J. A.; Wright, J. L. C. J. Nat. Prod. 1992, 55, 1631-1637; later revised to P. maculosum Faust (class, Dinophyceae; family, Prorocentraceae); Faust, M. A. Phycologia 1993, 32, 410-418.
10. Originally referred to as Prorocentrum concavum Fukuyo; Hu, T.; Marr, J.; deFreitas, A. S. W.; Quilliam, M. A.; Walter, J. A.; Wright, J. L. C. J. Nat. Prod. 1992, 55, 1631-1637; later revised to P. maculosum Faust (class, Dinophyceae; family, Prorocentraceae); Faust, M. A. Phycologia 1993, 32, 410-418.
11. Hu, T.; Curtis, J. M.; Walter, J. A.; McLachlan, J. L.; Wright, J. L. C. Tetrahedron Lett. 1995, 36, 9273-9276.
12. Socrates, G. Infrared Characteristic Group Frequencies; John Wiley & Sons: New York, 1980; p 115
13. Pfeffer, P. E.; Valentine, K. M.; Parrish, F. W. J. Am. Chem. Soc. 1979, 101, 1265-1274
14. Christofides, J. C.; Davies, D. B. J. Chem. Soc., Chem. Commun. 1983, 324-326.
15. Torigoe, K.; Murata, M.; Yasumoto T.; Iwashita, T. J. Am. Chem. Soc. 1988, 110, 7876-7877.
16. Falk, M.; Spierenburg, P.; Walter, J. A. J. Comput. Chem. 1996, 17, 409-417.
17. Falk, M.; Sedgwick, J. Personal communication.
18. Hu, T.; Curtis, J. M.; Walter J. A.; Wright, J. L. C. J. Chem. Soc., Chem. Commun. 1995, 597-599.
19. Wright, J. L. C.; van Dolah, F.; Hu, T. Unpublished results.