Ypaoamide, a new broadly acting feeding deterrent from the marine cyanobacterium Lyngbya majuscula

Tetrahedron Letters

Volumn 37, Issue 35, 1996, Pages 6263-6266

  Nagle, Dale G ^a   Paul, Valerie J ^a   Roberts, Mary Ann ^b  

^a UNIVERSITY OF GUAM MARINE LABORATORY   (Guam)

^b OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TOXIN; UNCLASSIFIED DRUG; YPAOAMIDE;

ARTICLE; CYANOBACTERIUM; DRUG ISOLATION; DRUG STRUCTURE; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

CYANOBACTERIA; LYNGBYA MAJUSCULA; SCHIZOTHRIX CALCICOLA;

EID: 0030603067     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01391-3     Document Type: Article

References (13)

1. 1. Voucher specimen on file with Prof. William H. Gerwick's herbarium (Oregon State University College of Pharmacy).
2. 2. Nagle, D.G. and Paul, V.J. "Chemical Defense of a Tropical Marine Cyanobacteria Bloom" Manuscript in preparation (1996).
3. 3. Compound 1 is named to reflect the site of collection (Ypao Beach: "I-pow.")
4. 4. Cardellina, J.H. II; Marner, F-J.; Moore, R.E. J. Am. Chem. Soc. 1979, 101, 240-242.
5. 5. Simmons, C.J.; Marner, F-J.; Cardellina, J.H. II; Moore, R.E.; Seff, C. Tetrahedron Lett. 1979, 22, 2003-2006.
6. 6. Cardellina, J.H. II; Moore, R.E. Tetrahedron Lett, 1979, 22, 2007-2010.
7. 7. Moore, R.E.; Michael, E. Phytochemistry 1988, 27, 3101-3103.
8. 8. Koehn, F.E.; Longley, R.E.; Reed, J.K. J. Nat. Prod. 1992, 55, 613-619.
9. 3), 2.18 (2H; t; J = 8 Hz; H2″), 1.57 (2H; p; J = 8 Hz; H3″), 1.2 (2H; m; H4″), 1.1 (2H; m; H5″), 0.79 (3H; s; H7″-H9″).
10. R = 7.55 min, m/z 267 (6), 252 (11), 182 (99), 169 (19), 154 (5), 140 (8), 128 (100), 127 (53), 126 (47), 112 (18), 99 (22). Cultured L. majuscula extract compound: GC-EIMS retention time and spectrum were identical with that of authentic standard.
11. 11. Ryu, G.; Matsunaga, S.; Fusetani, N. Tetrahedron 1994, 50, 13409-13416.
12. 12. Talpir, R.; Benayahu, Y.; Kashman, Y.; Pannall, L.; Schleyer, M. Tetrahedron Lett. 1994, 35, 4453-4456.
13. 13. Orjala, J.; Nagle, D.G.; Hsu, V.L.; Gerwick, W.H. J. Am. Chem. Soc. 1995, 117, 8281-8282.