Comparative study of toxic and non-toxic cyanobacterial products: A novel glycoside, suomilide, from non-toxic Nodularia spumigena HKVV

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5529-5532

  Fujii, Kiyonaga ^a   Sivonen, Kaarina ^b   Adachi, Kyoko ^c   Noguchi, Kazuyoshi ^d   Shimizu, Youhei ^a   Sano, Hiroshi ^c   Hirayama, Kazuo ^d   Suzuki, Makoto ^a   Harada, Ken Ichi ^a  

^a MEIJO UNIVERSITY   (Japan)

^b UNIVERSITY OF HELSINKI   (Finland)

^c MARINE BIOTECHNOLOGY INSTITUTE   (Japan)

^d AJINOMOTO CO INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; NODULARIN; SUOMILIDE; UNCLASSIFIED DRUG;

ARTICLE; CYANOBACTERIUM; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CYANOBACTERIA; NODULARIA SPUMIGENA;

EID: 0030836340     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01193-3     Document Type: Article

References (21)

1. Fujii, K.; Sivonen, K.; Adachi, K.; Koguchi, K.; Sano, H.; Hirayama, K.; Suzuki, M.; Harada, K.-I. Tetrahedron Lett. to be submitted.
2. Rinehart, K. L.; Harada, K.-I.; Namikoshi, M.; Chen, C.; Harvis, C A..; Munro, M. H. G.; Blunt, J. W.; Mulligan, P. E.; Beasley, V. R.; Dahlem, A. M.; Carmichael, W. W. J. Am. Chem. Soc. 1988, 110, 8557-8558.
3. Harada, K-I.; Fujii, K.; Shimada, T.; Suzuki, M.; Sano, H.; Adachi, K.; Carmichael, W.W. Tetrahedron Lett., 1995, 36, 1511-1514.
4. Fujii, K.; Harada, K.-I.; Suzuki, M.; Kondo, F.; Ikai, Y.; Oka, H.; Carmichael, W. W.; Sivonen, K. "Harmful and Toxic Algal Blooms" Yasumoto, T.; Oshima, Y.; Fukuyo, Y. Eds. Intergovernmental Oceanographic Commission of UNESCO, 1996, 559-562.
5. Murakami, M.; Shin, H. J.; Matsuda, H.; Ishida, K.; Yamaguchi, K. Phytochemistry., 1997, 44, 449-452.
6. Murakami, M.; Okita, Y.; Matsuda, H.; Okino, T.; Yamaguchi, K. Tetrahedron Lett., 1994, 35, 3129-3132.
7. Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett., 1995, 36, 2785-2788.
8. Matsuda, H.; Okino, T.; Murakami, M.; Yamaguchi, K. Tetrahedron 1996, 52, 14501-14506.
9. Sivonen, K.; Kononen, K.; Esala, A.-L.; Niemelä, S. I. Hydrobiologia, 1989, 185, 3-8.
10. A fraction (145 mg) containing suomilide (1) was obtained from the 5% AcOH aq. extract of dried N. spumigena HKVV (16 g) and was separated to give 1 (28 mg) by the following chromatography: silica gel using CHCl3:MeOH:H2O =65:20:5 (lower phase) and AcOEt:i-PrOH:H2O =4:1:2 (upper layer) and TOYOPEARL HW-40F using MeOH.
11. Harada, K.-I.; Fujii, K.; Hyashi, K.; Suzuki, M.; Ikai, Y.; Oka, H. Tetrahedron Lett., 1996, 37, 3001-3004.
12. 1H-NMR 1 (CD3OD) α-glucose δ 5.01 (d, J= 4.2 Hz, H-1), 4.48 (dd, J= 4.2 and 10.2 Hz, H-2), 3.77 (dd, J= 10.2 and 9.0 Hz, H-3), 3.33 (dd, J= 9.0 and 12.0 Hz, H-4), 3.82 (ddd, J= 12.0, 6.6 and 2.4 Hz, H-5), 4.15 (dd. J= 11.5 and 5.4 Hz, H-6), 4.43 (dd, J= 10.2, and 1.8 Hz, H-6′).
13. Shin, H. J.; Murakami, M.; Matsuda, H.; Ishida, K.; Yamaguchi, K. Tetrahedron Lett., 1995, 36, 5235-5238.
14. Product ion spectra were taken using a JMS-HX110/110A (JEOL) instrument: ion source, FAB; matrix, glycerin-NBA.
15. Ohtani, I.; Moore, R. E.; Runnegar, M. T. C. J. Am. Chem. Soc., 1992, 114, 7941-7942.
16. + calcd. for C32H67O8, Δ -1.1 mmu.
17. A fraction (400 mg) containing the glycolipid was obtained from the EtOH extract of residue after the 5% AcOH aq. extraction of dried N. spumigena HKVV (5 g) and was separated to give the glycolipid (23.9 mg) by silica gel chromatography using CHCl3:MeOH:H2O =65:10:5 (lower phase) and CHCl3:MeOH: H2O =65:20:5 (lower phase).
18. Soriente, A.; Sodano, G.; Gambacorta, A.; Trincone, A. Tetrahedron, 1992, 48, 5375-5384.
19. Suomilide (1) inhibited thrombin, plasmin and trypsin with an IC50 of 20.3 μg/mL, 6.8 μg/mL and 1.9 μg/mL, respectively.
20. Namikoshi, M.; Rinehart, K. L. J. Ind. Microbiol., 1996, 17, 373-384.
21. Sivonen, K.; Himberg, K.; Luukkainen, R.; Niemelä, S. I.; Poon, G. K.; Codd, G. A. Toxicity Assessment, 1989, 4, 339-352.