Identification and characterization of pectenotoxin (PTX) 4 and PTX7 as spiroketal stereoisomers of two previously reported pectenotoxins

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2475-2480

  Sasaki, Katsunori ^b   Wright, Jeffrey L C ^b   Yasumoto, Takeshi ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

PECTENOTOXIN; PECTENOTOXIN 4; PECTENOTOXIN 7; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; ARTIFACT REDUCTION; CHEMICAL ANALYSIS; NONHUMAN; SHELLFISH; STEREOISOMERISM; STRUCTURE ANALYSIS; TOXIN ANALYSIS;

EID: 0032540486     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971310b     Document Type: Article

References (23)

1. Yasumoto, T.; Murata, M.; Oshima, Y.; Sano, M.; Matsumoto, G. K.; Clardy, J. Tetrahedron 1985, 41, 1019.
2. Murata, M.; Sano, M.; Iwashita, T.; Naoki, H.; Yasumoto, T. Agric. Biol. Chem. 1986, 50, 2693.
3. Yasumoto, T.; Murata, M.; Lee, J.-S.; Torigoe, K. in Bioactive Molecules: Mycotoxins and Phycotoxins '88; Natori, S., Hashimoto, K., Ueno, Y., Eds.; Elsevier: New York, 1989; Vol 10, p 375.
4. Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
5. Ishige, M.; Satoh, N.; Yasumoto, T. Reps. Hokkaido Inst. Health, 1988, 38, 15.
6. (a) Takai, A.; Bialojan, C.; Troschka M.; Rüegg, J. C. FEBS Lett. 1987, 217, 81.
7. (b) Cohen, P.; Holmes, C. F. B.; Tsukitani, Y. Trends Biochem. Sci. 1990, 15, 98.
8. Sasaki, K.; Satake, M.; Yasumoto, T. Biosci. Biotech. Biochem. 1997, 61, 1783.
9. (a) Shimizu, Y. Chem. Rev. 1993, 93, 1685,
10. (b) Garson, M. J. ibid. 1699.
11. Lee, J.-S.; Igarashi, T.; Fraga, S.; Dabl, E.; Hovgaard, P.; Yasumoto, T. J. Appl. Phycol. 1989, 1, 147.
12. Draisci, R.; Lucentini, L.; Gianetti, L.; Boria, P.; Poletti, R. Toxicon 1996, 34, 923.
13. For a detailed review of spiroketal chemistry: Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617.
14. Satake, M.; Ishibashi, Y.; Legrand, A. M.; Yasumoto, T. Biosci. Biotech. Biochem. 1997, 60, 2103.
15. Relevant examples can be found in: (a) Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796.
16. (b) Murata, M.; Legrand, A. M.; Scheuer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525.
17. (c) Pettit, G. R.; Ichihara, Y.; Wurzel, G.; Williams, M. D.; Schmidt, J. M.; Chapuis, J. J. Chem. Soc., Chem. Commun. 1995, 383.
18. Lee, J.-S.; Yanagi, T.; Kenma, R.; Yasumoto, T. Agric. Biol. Chem. 1987, 51, 877.
19. (a) Uemura, D.; Takahashi, K.; Yamamoto, T.; Katayama, C.; Tanaka, J.; Okumura, Y.; Hirata, Y. J. Am. Chem. Soc. 1985, 107, 4796.
20. (b) Pettit, G. R.; Tan. R.; Gao, F.; Williams, M. D.; Doubek, D. L.; Boyd, M. R.; Schmidt, J. M.; Chapuis, J.-C.; Hamel, E.; Bai, R.; Hooper, J. N. A.; Tackett, L. P. J. Org. Chem. 1993, 58, 2538.
21. (c) Litaudon, M.; Hart, J. B.; Blunt, J. W.; Lake, R. J.; Munro, M. H. G. Tetrahedron Lett. 1994, 35, 9435.
22. Moore, R. E.; Blackman, A. J.; Cheuk, C. E.; Mynderse, J. S.; Matsumoto, G. K.; Clardy, J.; Woodard, R. W.; Craig, J. C. J. Org. Chem. 1984, 49, 2484.
23. Hart, J. B.; Blunt, J. W.; Munro, M. H. G. J. Org. Chem. 1996, 61, 2888.