Keramamides M and N, two new cyclic peptides with a sulfate ester from Theonella sponge

Tetrahedron

Volumn 55, Issue 43, 1999, Pages 12543-12548

  Tsuda, Masashi ^a   Ishiyama, Haruaki ^a   Masuko, Kanami ^a   Takao, Toshifumi ^a,b   Shimonishi, Yasutsugu ^a,b   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CYCLOPEPTIDE; KERAMAMIDE M; KERAMAMIDE N; SULFATE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; SPECTRAL SENSITIVITY; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION;

EID: 0033595875     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00744-9     Document Type: Article

References (22)

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16. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.
17. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.
18. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.
19. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.
20. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.
21. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.
22. Discodermins, polydiscamide A, and halicylindramides contained a sulfonate group in the cysteic acid residue. Discodermins: Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1984, 25, 5165-5168; Matsunaga, S.; Fusetani, N.; Konosu, S. Tetrahedron Lett. 1985, 26, 855-858; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron Lett. 1994, 35, 8251-8254; Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416. Polydiscamide A: Gulavita, N. K.; Gunesekera, S. P.; Pomponi, S. A.; Robinson, E. V. J. Org. Chem. 1992, 57, 1767-1772. Halicylindramides: Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Med. Chem. 1995, 38, 338-343; Li, H.-Y.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., 1996, 59, 163-166.