Isolation and structure of pinnatoxin D, a new shellfish poison from the Okinawan bivalve Pinna muricata

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4027-4030

  Chou, Tong ^b   Haino, Takeharu ^b   Kuramoto, Makoto ^a   Uemura, Daisuke ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FISH VENOM; PINNATOXIN D; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SHELLFISH;

BIVALVIA; PINNA MURICATA;

EID: 0030013558     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00753-8     Document Type: Article

References (18)

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2. a) Uemura, D.; Ueda, K.; Hirata, Y.; Naoki, H.; Iwashita, T. Tetrahedron Lett. 1981, 22, 2781.
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7. Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S. Z.; Chen, H. S. J. Am. Chem. Soc. 1995, 117, 1155 and Chou, T.; Kamo, O.; Uemura, D. Tetrahedron Lett., this issue.
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9. Pinnatoxins B and C are the most potent toxins in this series. Their structures will be reported soon.
10. 3CN/0.1% TFA) to give 2.0 mg pinnatoxin D (1).
11. 3OD, δppm) : 52.0 (t, C-1), 39.5 (d, C-2) 35.7 (d, C-3), 36.3 (t, C-4), 52.1 (s, C-5), 203.3 (s, C-6), 35.3 (t, C-7) 21.6 (t, C-8), 33.6 (t, C-9), 145.3 (s, C-10), 46.5 (t, C-11), 69.6 (d, C-12), 29.8 (t, C-13), 35.6 (t, C-14), 71.6 (s, C-15), 113.7 (s, C-16), 32.6 (t, C-17), 38.8 (t, C-18), 110.1 (s, C-19), 37.6 (t, C-20), 32.4 (d, C-21), 69.9 (d, C-22), 73.2 (d, C-23), 40.5 (t, C-24), 110.6 (s, C-25), 45.0 (t, C-26), 26.0 (d, C-27), 33.6 (t, C-28), 77.1 (d, C-29), 80.1 (d, C-30), 45.6 (d, C-31), 136.0 (d, C-32), 141.4 (s, C-33), 200.0 (s, C-34), 33.2 (t, C-35), 22.7 (t, C-36), 176.8 (s, C-37), 33.2 (t, C-38), 22.7 (q, C-39), 18.4 (q, C-40), 23.1 (q, C-41), 112.6 (t, C-42), 33.8 (t, C-43), 21.4 (q, C-44), 20.0 (q, C-45).
12. 13C-NMR spectrum of Schiff base, the carbon signal of iminum salt was observed approximately 200 ppm downfield.
13. Davis, D. G.; Bax, A. J. Am. Chem. Soc. 1985, 107, 2820.
14. Bax, A.; Griffey, R. H.; Hawkins, B. L. J. Am. Chem. Soc. 1983, 105, 7188.
15. Hurd, R. E.; John, B. K. J. Magn. Reson. 1991, 91, 648.
16. 6 homoallylic coupling correlation between H1/H7 and hetero long-range coupling correlation between H7/C6 were observed in the spectra of the corresponding methyl ester.
17. 3OD with mixing times of 400ms.
18. The J value was assigned using a triple resonance homodecoupling technique and a homodecoupling difference spectrum.