Molluscicidal metabolites from an assemblage of Palmyra Atoll cyanobacteria

Journal of Natural Products

Volumn 74, Issue 5, 2011, Pages 1175-1181

  Pereira, Alban R ^a   Etzbach, Lena ^a,b   Engene, Niclas ^a   Müller, Rolf ^b   Gerwick, William H ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

MOLLUSCACIDE; PALMYRROLINONE; THIOPALMYRONE; UNCLASSIFIED DRUG;

ARTICLE; BIOMPHALARIA GLABRATA; CYANOBACTERIUM; DRUG ACTIVITY; DRUG ISOLATION; HORMOSCILLA; IC 50; NONHUMAN; NUCLEOTIDE SEQUENCE; OSCILLATORIA;

ANIMALS; BIOMPHALARIA; CYANOBACTERIA; DEVELOPING COUNTRIES; HETEROCYCLIC COMPOUNDS, 1-RING; MOLECULAR STRUCTURE; MOLLUSCACIDES; NEGLECTED DISEASES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRROLES; SCHISTOSOMIASIS; SULFUR COMPOUNDS;

BIOMPHALARIA; BIOMPHALARIA GLABRATA; CYANOBACTERIA; GASTROPODA; OSCILLATORIA; PALMYRA;

EID: 79957858310     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200106b     Document Type: Article

References (54)

1. (a) Payne, L.; Fitchett, J. R. Trends Parasitol. 2010, 26, 421-423.
2. (b) Hotez, P. J.; Fenwick, A.; Savioli, L.; Molyneux, D. H. Lancet 2009, 373, 1570-1575.
3. (c) World Health Organization Control of neglected tropical diseases (NTD). http://www.who.int/neglected-diseases/en/. Accessed October 28, 2010.
4. Molyneux, D. H.; Hotez, P. J.; Fenwick, A. PLoS Med. 2005, 2, 1064-1070.
5. Reddy, M.; Gill, S. S.; Kalkar, S. R.; Wu, W.; Anderson, P. J.; Rochon, P. A. JAMA 2007, 298, 1911-1924.
6. (a) Domling, A.; Khoury, K. ChemMedChem 2010, 5, 1420-1434.
7. (b) Feasey, N.; Wansbrough-Jones, M.; Mabey, D. C. W.; Solomon, A. W. Brit. Med. Bull. 2010, 93, 179-200.
8. (c) Trouiller, P.; Olliaro, P.; Torreele, E.; Orbinski, J.; Laing, R.; Ford, N. Lancet 2002, 359, 2188-2194.
9. Kursar, T. A.; Caballero-George, C. C.; Capson, T. L.; Cubilla- Rios, L.; Gerwick, W. H.; Gupta, M. P.; Ibañez, A.; Linington, R. G.; McPhail, K. L.; Ortega-Barria, E.; Romero, L. I.; Solis, P. N.; Coley, P. D. BioScience 2006, 56, 1005-1012.
10. (a) Perrett, S.; Whitfield, P. J. Parasitol. Today 1996, 12, 156-159.
11. (b) World Health Organization. Report of the Scientific Working Group Meeting on Schistosomiasis; Geneva, Switzerland, November 14-16, 2005.
12. (a) Bergquist, R. Acta Trop. 2008, 108, 65-68.
13. (b) Ribeiro, K. A.; de Carvalho, C. M.; Molina, M. T.; Lima, E. P.; Lopez-Montero, E.; Reys, J. R.; de Oliveira, M. B.; Pinto, A. V.; Santana, A. E.; Goulart, M. O. Acta Trop. 2009, 111, 44-50.
14. Hostettmann, K.; Kizu, H.; Tomimori, T. Planta Med. 1982, 44, 34-35.
15. Orjala, J.; Gerwick, W. H. J. Nat. Prod. 1996, 59, 427-430.
16. Singh, I. P.; Milligan, K. E.; Gerwick, W. H. J. Nat. Prod. 1999, 62, 1333-1335.
17. Pereira, A. R.; McCue, C. F.; Gerwick, W. H. J. Nat. Prod. 2010, 73, 217-220.
18. (a) Cardellina, J. H.; Dalietos, D.; Marner, F. J.; Mynderse, J. S.; Moore, R. E. Phytochemistry 1978, 17, 2091-2095.
19. (b) Kwan, J. C.; Teplitski, M.; Gunasekera, S. P.; Paul, V. J.; Luesch, H. J. Nat. Prod. 2010, 73, 463-466.
20. (c) Chen, J.; Shi, Z. F.; Zhou, L.; Xie, A. L.; Cao, X. P. Tetrahedron 2010, 66, 3499-3507.
21. (a) Wegerski, C. J.; France, D.; Cornell-Kennon, S.; Crews, P. Bioorg. Med. Chem. 2004, 12, 5631-5637.
22. (b) Eisenreich, W.; Bacher, A.; Berry, A.; Bretzel, W.; Humbelin, M.; Lopez-Ulibarri, R.; Mayer, A. F.; Yeliseev, A. J. Org. Chem. 2002, 67, 871-875.
23. (c) Englert, G.; Noack, K.; Broger, E. A.; Glinz, E.; Vecchi, M.; Zell, R. Helv. Chim. Acta 1991, 74, 969-982.
24. (d) Moss, G. P. Pure. Appl. Chem. 1976, 47, 97-102.
25. (e) Maoka, T.; Arai, A.; Shimizu, M.; Matsuno, T. Comp. Biochem. Physiol. 1986, 83B, 121-124.
26. (f) Buchecker, R.; Liaaen-Jensen, S.; Borch, G.; Siegelman, H. W. Phytochemistry 1976, 15, 1015-1018.
27. (a) Ward, D. E.; Gai, Y.; Zoghaib, W. M. Can. J. Chem. 1991, 69, 1487-1497.
28. (b) Schweiger, K. Monatsh. Chem. 1982, 113, 1283-1297.
29. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866-876.
30. Uhrin, D.; Batta, G.; Hruby, V. J.; Barlow, P. N.; Kover, K. E. J. Magn. Reson. 1998, 130, 155-161.
31. Williamson, R. T.; Marquez, B. L.; Gerwick, W. H.; Kover, K. E. Magn. Reson. Chem. 2000, 38, 265-273.
32. (a) Lightner, D. A.; Gurst, J. E. Organic Conformational Analysis and Stereochemistry from Circular Dichroism Spectroscopy; Wiley-VCH: New York, 2000; pp 337-394.
33. (b) Snatzke, G. Tetrahedron 1965, 21, 439-448.
34. (c) Snatzke, G. Tetrahedron 1965, 21, 413-419.
35. (d) Snatzke, G. Tetrahedron 1965, 21, 421-438.
36. (e) Suga, T.; Imamura, K. Bull. Chem. Soc. Jpn. 1972, 45, 2060-2064.
37. 3)}. See: Pospisil, J.; Marko, I. E. Tetrahedron Lett. 2008, 49, 1523-1526.
38. (a) Meickle, T.; Matthew, S.; Ross, C.; Luesch, H.; Paul, V. Planta Med. 2009, 75, 1427-1430.
39. (b) Edwards, D. J.; Marquez, B. L.; Nogle, L. M.; McPhail, K.; Goeger, D. E.; Roberts, M. A.; Gerwick, W. H. Chem. Biol. 2004, 11, 817-833.
40. (c) Koehn, F. E.; Longley, R. E.; Reed, J. K. J. Nat. Prod. 1992, 55, 613-619.
41. (d) Moore, R. E.; Entzeroth, M. Phytochemistry 1988, 27, 3101-3103.
42. Tidgewell, K., Clark, B. T., Gerwick, W. H. In Comprehensive Natural Products Chemistry, 2nd ed.; Moore, B.; Crews, P., Eds.; Pergamon Press: Oxford, 2010; pp 141-188.
43. (a) Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 1806-1807.
44. (b) Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 13506-13506.
45. Gomont, M. M. Ann. Sci. Nat. Bot. Ser. 1892, 16, 91-264.
46. Castenholz, R. W.; Rippka, R.; Herdman, M. In Bergey's Manual of Systematic Bacteriology; Boone, D. R.; Castenholz, R. W., Eds.; Springer: New York, 2001; Vol. 1, pp 473-599.
47. Komárek, J.; Anagnostidis, K. In Süsswasserflora von Mitteleuropa; Büdel, B.; Gärtner, G.; Krienitz, L.; Schagerl, M., Eds.; Elsevier: München, 2005; Vol 19/2, pp 441-625.
48. Taniguchi, M.; Nunnery, J. K.; Engene, N.; Esquenazi, E.; Byrum, T.; Dorrestein, P. C.; Gerwick, W. H. J. Nat. Prod. 2010, 73, 393-398.
49. Katoh, K.; Toh, H. Briefings Bioinf. 2008, 9, 286-298.
50. Cannone, J. J.; Subramanin, S.; Schnare, M. N.; Collett, J. R.; D'Souza, L. M.; Du, Y.; Feng, B.; Lin, N.; Madabusi, L. V.; Muller, K. M.; Pnde, N.; Schang,Z.;Yu, N.;Gutell, R. R. BMC Bioinf. 2002, 3, 1471-2105.
51. Posada, D. Mol. Biol. Evol. 2008, 25, 1253-1256.
52. Zwickl, D. J. Ph.D. Thesis, University of Texas at Austin, TX, 2006.
53. Ronquist, F.; Huelsenbeck, J. P. Bioinformatics 2003, 12, 1572-1574.
54. Nylander, J. A. A.; Wilgenbusch, J. C.; Warren, D. L.; Swofford, D. L. Bioinformatics 2008, 15, 581-583.