Peyssonenynes A and B, novel enediyne oxylipins with DNA methyl transferase inhibitory activity from the red marine alga Peyssonnelia caulifera

Journal of Natural Products

Volumn 67, Issue 6, 2004, Pages 1010-1013

  McPhail, Kerry L ^a   France, Dennis ^b   Cornell Kennon, Susan ^b   Gerwick, William H ^a  

^a OREGON STATE UNIVERSITY   (United States)

^b NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA METHYLTRANSFERASE; DNA METHYLTRANSFERASE INHIBITOR; DRUG METABOLITE; ENZYME INHIBITOR; MONOACYLGLYCEROL; OMEGA 3 FATTY ACID; OXYLIPIN DERIVATIVE; PEYSSONENYNE A; PEYSSONENYNE B; PEYSSOPYRONE; UNCLASSIFIED DRUG;

ARTICLE; BIOASSAY; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STABILITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; FRACTIONATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; METABOLITE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEYSSONNELIA CAULIFERA; PROTON NUCLEAR MAGNETIC RESONANCE; RED ALGA; STEREOCHEMISTRY; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

ALGAE, RED; DNA MODIFICATION METHYLASES; ENEDIYNES; ENZYME INHIBITORS; FATTY ACIDS, UNSATURATED; FIJI; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRONES;

ALGAE; PEYSSONNELIA; RHODOPHYTA;

EID: 3042671182     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np0400252     Document Type: Article

References (28)

1. Manez, S.; Del Carmen Recio, M. Stud. Nat. Prod. Chem. 2002, 27, 819-890.
2. (b) Singh, R. P.; Dhanalakshmi, S.; Agarwal, R. Cell Cycle 2002, 1, 156-161.
3. (c) Primiano, T.; Yu, R.; Kong, A.-N. T. Pharm. Biol. 2001, 39, 83-107.
4. (d) Cragg, G. M.; Newman D. J. Exp. Opin. Investig. Drugs 2000, 9, 2783-2797.
5. (e) Johnson, R. K.; Hertzberg, R. P. Annu. Rep. Med. Chem. 1990, 25, 129-140.
6. Milutinovic, S.; Knox, J.; Szyf, M. J. Biol. Chem. 2000, 275, 6353-6359.
7. (b) Fournel, M.; Sapieha, P.; Beaulieu, N.; Besterman, J.; MacLeod, A. J. Biol. Chem. 1999, 274, 24250-24256.
8. Yoo, H.-D.; Ketchum, S. O.; France, D.; Bair, K.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 51-53.
9. (b) Crews, P.; Slate, D. L.; Gerwick, W. H.; Schmitz, F. J.; Schatzman, R.; Strulovici, B.; Canon, P.; Hunter, L. M. In Proceedings of the 2nd Anticancer Discovery and Development Symposium, 1991; Valeriote, F., Corbett, T., Eds.; Kluwer Academic Publishers: Norwell, MA, 1991.
10. Gerwick, W. H.; Singh I.-P. In Lipid Biotechnology; Kuo, T. M., Gardner, H. W., Eds.; Marcel Dekker: New York, 2002; pp 249-275.
11. (b) Gerwick, W. H.; Bernart, M. W.; Moghaddam, M. F.; Jiang, Z. D.; Solem, M. L.; Nagle, D. G. Hydrobiologia 1990, 204-205, 621-628.
12. (c) Jiang, Z. D.; Ketchum, S. O.; Gerwick, W. H. Phytochemistry 2000, 53, 129-133.
13. (d) Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49.
14. Gerwick, W. H. Chem. Rev. 1993, 93, 1807-1823.
15. Higgs, M. D.; Mulheim, L. J. Tetrahedron 1981, 37, 4259-4262.
16. Graber, M. A.; Gerwick, W. H.; Cheney, D. P. Tetrahedron Lett. 1996, 37, 4635-4638.
17. Paul, V. J.; Fenical, W. Tetrahedron Lett. 1980, 21, 3327-3330.
18. Su, J.; Yang, X. Gaodeng Xuexiao Huaxue Xuebao 1993, 14, 951-953.
19. Jiang, Z. D.; Gerwick, W. H. Lipids 1991, 26, 960-963.
20. (b) Jiang, Z. D.; Gerwick, W. H. Phytochemistry 1990, 29, 1433-1440.
21. Talpir, R.; Rudi, A.; Kashman, Y.; Loya, Y.; Hizi, A. Tetrahedron 1994, 50, 4179-4184.
22. Su, J.; Yang, X. Zhongguo Haiyang Yaowu 1992, 11, 1-3.
23. Pfeffer, P. E.; Luddy, F. E.; Unruh, J.; Shoolery, J. N. J. Am. Oil Chem. Soc. 1977, 54, 380-386.
24. (b) Pfeffer, P. E.; Sonnet, P. E.; Schwartz, D. P.; Osman, S. F.; Weisleder, D. Lipids 1992, 27, 258-288.
25. Tada, H.; Yasuda, F. Chem. Lett. 1984, 779-780.
26. Uno, M.; Ohta, S.; Ohta, E.; Ikegami, S. J. Nat. Prod. 1996, 59, 1146-1148.
27. Hagmann, L.; Juettner, F. Tetrahedron Lett. 1996, 37, 6539-6542.
28. Bernart, M. W.; Cardellina, J. H., II; Balaschak, M. S.; Alexander, M.; Shoemaker, R. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 748-753.