Comparative study of toxic and non-toxic cyanobacterial products: Novel peptides from toxic Nodularia spumigena AV1

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5525-5528

  Fujii, Kiyonaga ^a   Sivonen, Kaarina ^b   Adachi, Kyoko ^c   Noguchi, Kazuyoshi ^d   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

CYCLOPEPTIDE; NODULAPEPTIN A; NODULAPEPTIN B; NODULARIN; SPUMIGIN A; SPUMIGIN B; SPUMIGIN C; UNCLASSIFIED DRUG;

ARTICLE; CYANOBACTERIUM; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TOXIN ANALYSIS;

CYANOBACTERIA; NODULARIA SPUMIGENA;

EID: 0030762624     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01192-1     Document Type: Article

References (19)

1. Carmicael, W. W. Scientific American 1994, 270, 64-72.
2. Matsunaga, S.; Moore, R. E.; Niemczura, W. P.; Carmichael, W. W. J. Am. Chem. Soc. 1989, 111, 8021-8023.
3. Namikoshi, M.; Rinehart, K. L. J. Ind. Microbiol. 1996, 17, 373-384.
4. Harada, K.-I.; Mayumi, T.; Shimada, T.; Suzuki, M.; Kondo, F.; Watanabe, M. F. Tetrahedron Lett. 1993, 34, 6091-6094.
5. Harada, K.-I.; Mayumi, T.; Shimada, T.; Suzuki, M.; Kondo, F.; Park, H.; Watanabe, M. F. 35th Sympo. Chem. Natur. Prod. Sympo. Paper, Kyoto, 1993; pp. 377-384.
6. Harada, K.-I.; Fujii, K.; Shimada, T.; Suzuki, M.; Sano, H.; Adachi, K.; Carmichael, W.W. Tetrahedron Lett. 1995, 36, 1511-1514.
7. 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: Sendai, 1996; pp. 559-562.
8. 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.
9. Sivonen, K.; Kononen, K.; Carmicael, W. W.; Dahlem, A. M.; Rinehart, K. L.; Kiviranta, J.; Niemelä, S. I. Appl. Eviron. Microbiol. 1989, 55, 1990-1995.
10. A fraction (95 mg) containing nodulapeptins, spumigins and nodularin was obtained from the 5% AcOH aq. extract of dried N. spumigena AV1 (4.7 g) and was separated to give nodularin (11 mg), 1 (2.0 mg), 2 (6.0 mg), 3 (1.5 mg), 4 (3.0 mg), 5 (2.1 mg) and 6 (2.0 mg) by the following chromatography: silica gel using AcOEt:i-PrOH:H20 =4:3:7 (upper layer), CHCl3:MeOH:H2O =65:25:5 (lower phase), CHCl3: MeOH:5% AcOH aq. =65:20:5 (lower phase) and CHCl3:MeOH:5% AcOH aq. =65:35:10 (lower phase) 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. Product ion spectra were taken using a JMS-HX110/110A (JEOL) instrument: ion source, FAB; matrix, glycerin-NBA.
13. Morihara, K. Bull. Chem. Soc. Jpn. 1964, 37, 1781-1784.
14. Elucidation of the absolute configuration of the sulfoxide of 2 is now in progress.
15. Murakami, M.; Okita, Y.; Matsuda, H.; Okino, T.; Yamaguchi, K. Tetrahedron Lett. 1994, 35, 3129-3132.
16. Murakami, M.; Ishida, K.; Okino, T.; Okita, Y.; Matsuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 2785-2788.
17. Matsuda, H.; Okino, T.; Murakami, M.; Yamaguchi, K. Tetrahedron 1996, 52, 14501-14506.
18. Spumigin A (3) inhibited thrombin, plasmin and trypsin with an IC50 of 4.6, 4.9 and 16.1 μg/mL, respectively, and B1 (4) inhibited trypsin with an IC50 of 20.7 μg/mL.
19. Fukushima, K.; Arai, T.; Mon, Y.; Tsuboi, M.; Suzuki, M. J. Antibiot. 1983, 36, 1613-1630.