Prymnesin-2: A potent ichthyotoxic and hemolytic glycoside isolated from the red tide alga Prymnesium parvum

Journal of the American Chemical Society

Volumn 118, Issue 2, 1996, Pages 479-480

  Igarashi, Tomoji ^a,b   Satake, Masayuki ^b   Yasumoto, Takeshi ^b  

^a JAPAN FOOD RESEARCH LABORATORIES   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; PRYMNESIN 2; TOXIN; UNCLASSIFIED DRUG;

ALGA; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; DRUG TOXICITY; FISH; HEMOLYSIS; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0030070097     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9534112     Document Type: Article

References (16)

1. (a) Otterström, C. V.; Steemann-Nielsen, E. Rep. Dan. Biol. Sta. 1939, 44, 5-24.
2. (b) Eikrem, W.; Throndsen, J. In Toxic Phytoplankton Blooms in the Sea; Smayde, T. J., Shimizu, Y., Eds.; Elsevier: Amsterdam, 1993; pp 687-692.
3. Yariv, J.; Hestrin, S. J. Gen. Microbiol. 1961, 24, 165-175.
4. Paster, Z. Rev. Int. Oceanogr. Med. 1968, 10, 249-258.
5. Ulitzur, S.; Shilo, M. Biochim. Biophys. Acta, 1970, 201, 350-363.
6. Igarashi, T.; Oshima, Y.; Murata, M.; Yasumoto, T. In Harmful Marine Algal Blooms; Lassus, P., et al., Eds.; Lavoisier Publishing: Paris, 1994; pp 303-308.
7. 5N (1:1) for 2 and for peracetyl- and perhydro-PRM2.
8. (a) Hirsh, S.; Carmely, S.; Kashman, Y. Tetrahedron 1987, 43, 3257-3261.
9. (b) Cimino, G.; De Stefano, S. Tetrahedron Lett. 1977, 1325-1328.
10. Chemical shifts of C88 (δ 68.4) and C89 (δ 69.7) are interchangeable.
11. Kreevoy, M. M.; Charman, H. B.; Vinard, D. R. J. Am. Chem. Soc. 1961, 83, 1978-1983.
12. Wright, A. E.; McConnell, O. J.; Kohmoto, S.; Lui, M. S.; Thompson, W.; Snader, K. M. Tetrahedron Lett. 1987, 28, 1377-1380.
13. Murata, M.; Naoki, H.; Iwashita, T.; Matsunaga, S.; Sasaki, M.; Yokoyama, A.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 2060-2062.
14. The stereochemical data for these two structures calculated by MM2 were very similar, except for the relative positions of H69 and H70 (see supporting information).
15. 13C NMR data were as follows: Cl′ (δ 5.38, 106.2); C2′ (δ 4.20, 74.6); C3′ (δ 4.18, 72.8); C4′ (δ 4.41, 88.2); C5′ a.b (δ 3.68, 3.73, 64.5).
16. We believe that a mechanical problem inherent to a quadrupole mass spectrometer in measuring a chlorinated large molecule resulted in the smaller difference (32 instead of 34 u) than it should have been.