Explorative solid-phase extraction (E-SPE) for accelerated microbial natural product discovery, dereplication, and purification

Journal of Natural Products

Volumn 73, Issue 6, 2010, Pages 1126-1132

  Månsson, Maria ^a   Phipps, Richard K ^a   Gram, Lone ^a   Munro, Murray H G ^b   Larsen, Thomas O ^a   Nielsen, Kristian F ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCT;

ARTICLE; BIOASSAY; DRUG PURIFICATION; ION EXCHANGE CHROMATOGRAPHY; PH MEASUREMENT; PKA; SOLID PHASE EXTRACTION;

BACTERIA; BIOLOGICAL PRODUCTS; CHROMATOGRAPHY, ION EXCHANGE; DATABASES, FACTUAL; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; SOLID PHASE EXTRACTION;

EID: 77954067426     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np100151y     Document Type: Article

References (62)

1. Houghton, P. J. and Raman, A. Laboratory Handbook for the Fractionation of Natural Extracts, 1st ed.; Chapman & Hall: London, 1998.
2. Cannell, R. J. P., Dufresne, C., Gailliot, F. P., Venkat, E., Kothandaraman, S., Salituro, G. M., Stead, P., Gibbons, S., Gray, A. I., McAlpine, J., Shankland, N., Florence, A. J., VanMiddlesworth, F., Shimizu, Y., Silva, G. L., Lee, I.-S., Kinghorn, A. D., Wright, A., Verrall, M. S., and Warr, S. R. C. Natural Products Isolation, 1st ed.; Humana Press Inc.: Totowa, NJ, 1998; Vol. 4.
3. Lang, G., Mayhudin, N. A., Mitova, M. I., Sun, L., Van der Sar, S., Blunt, J. W., Cole, A. L. J., Ellis, G., Laatsch, H., and Munro, M. H. G. J. Nat. Prod. 2008, 71, 1595-1599
4. Bugni, T. S., Harper, M. K., McCulloch, M. W. B., Reppart, J., and Ireland, C. M. Molecules 2008, 13, 1372-1383
5. Blunt, J. W., Calder, V. L., Fenwick, G. D., Lake, R. J., Mccombs, J. D., Munro, M. H. G., and Perry, N. B. J. Nat. Prod. 1987, 50, 290-292
6. Ghisalberti, E. L. Bioactive Natural Products: Detection, Isolation, and Structural Determination, 1st ed.; CRC Press, Inc.: Boca Raton, FL, 1993.
7. Lang, G., Mayhudin, N. A., Mitova, M. I., Sun, L., van der Sar, S., Blunt, J. W., Cole, A. L. J., Ellis, G., Laatsch, H., and Munro, M. H. G. J. Nat. Prod. 2008, 71, 1595-1599
8. Fenical, W. Chem. Rev. 1993, 93, 1673-1683
9. Jarvis, B. B. Phytochem. Anal. 1992, 3, 241-249
10. Hinkley, S. F. and Jarvis, B. B. Chromatographic method for Stachybotrys toxins. In Methods Molecular Biology. 157. Mycotoxin Protocols; Pohland, A. and Trucksess, M. W., Eds.; Humana Press: Totowa, NJ, 2000; pp 173-194.
11. Northcote, P. T., Blunt, J. W., and Munro, M. H. G. Tetrahedron Lett. 1991, 32, 6411-6414
12. Kelm, M. A., Johnson, J. C., Robbins, R. J., Hammerstone, J. F., and Schmitz, H. H. J. Agric. Food Chem. 2006, 54, 1571-1576
13. Samuelsson, G., Kyerematen, G., and Farah, M. H. J. Ethnopharmacol. 1985, 14, 193-201
14. Bjerg, B., Olsen, O., Rasmussen, K. V., and Sørensen, H. J. Liq. Chromatogr. 1984, 7, 691-707
15. Guo, J. C. and Gould, S. J. Phytochemistry 1993, 32, 535-541
16. MacKenzie, S. E., Savard, M. E., Blackwell, B. A., Miller, J. D., and Apsimon, J. W. J. Nat. Prod. 1998, 61, 367-369
17. Hennion, M. C. J. Chromatogr., A 1999, 856, 3-54
18. Nielsen, K. F., Dalsgaard, P. W., Smedsgaard, J., and Larsen, T. O. J. Agric. Food Chem. 2005, 53, 2908-2913
19. Kanaujia, P. K., Pardasani, D., Gupta, A. K., Kumar, R., Srivastava, R. K., and Dubey, D. K. J. Chromatogr., A 2007, 1161, 98-104
20. Wilson, T. J. and Romer, T. R. J. AOAC 1991, 74, 951-956
21. Nielsen, K. F., Mogensen, J. M., Johansen, M., Larsen, T. O., and Frisvad, J. C. Anal. Bioanal. Chem. 2009, 395, 1225-1242
22. Laven, M., Alsberg, T., Yu, Y., Adolfsson-Erici, M., and Sun, H. W. J. Chromatogr., A 2009, 1216, 49-62
23. Cardellina, J. H., Munro, M. H. G., Fuller, R. W., Manfredi, K. P., Mckee, T. C., Tischler, M., Bokesch, H. R., Gustafson, K. R., Beutler, J. A., and Boyd, M. R. J. Nat. Prod. 1993, 56, 1123-1129
24. Larsen, T. O., Smedsgaard, J., Nielsen, K. F., Hansen, M. E., and Frisvad, J. C. Nat. Prod. Rep. 2005, 22, 672-695
25. Horinouchi, S. Biosci., Biotechnol., Biochem. 2007, 71, 283-299
26. Keller, N. P., Turner, G., and Bennett, J. W. Nat. Rev. Microbiol. 2005, 3, 937-947
27. David, H., Ozcelik, I. S., Hofmann, G., and Nielsen, J. BMC Genomics 2008, 9
28. Fox, E. M. and Howlett, B. J. Curr. Opin. Microbiol. 2008, 11, 481-487
29. Laatsch, H. AntiBase 2008; Wiley-VCH: Weinheim, Germany, 2008; http://www.users.gwdg.de/∼ucoc/laatschAntibase.htm.
30. Claeson, P., Goransson, U., Johansson, S., Luijendijk, T., and Bohlin, L. J. Nat. Prod. 1998, 61, 77-81
31. Toth, G. B. and Pavia, H. J. Chem. Ecol. 2001, 27, 1899-1910
32. Kupchan, S. M., Doskotch, R. W., Bollinge, P., McPhail, A. T., Sim, G. A., and Renauld, J. A. S. J. Am. Chem. Soc. 1965, 87, 5805-&
33. Hougaard, L., Anthoni, U., Christophersen, C., Larsen, C., and Nielsen, P. H. Comp. Biochem. Physiol., Part B: Biochem. Mol. Biol. 1991, 99, 469-472
34. Nielsen, K. F. and Smedsgaard, J. J. Chromatogr., A 2003, 1002, 111-136
35. Bowman, J. P. Marine Drugs 2007, 5, 220-241
36. Andersen, R. J., Wolfe, M. S., and Faulkner, D. J. Marine Biol. 1974, 27, 281-285
37. Kalinovskaya, N. I., Ivanova, E. P., Alexeeva, Y. V., Gorshkova, N. M., Kuznetsova, T. A., Dmitrenok, A. S., and Nicolau, D. V. Curr. Microbiol. 2004, 48, 441-446
38. McCarthy, S. A., Johnson, R. M., and Kakimoto, D. J. Appl. Bacteriol. 1994, 77, 426-432
39. Gauthier, M. J. and Flatau, G. N. Can. J. Microbiol. 1976, 22, 1612-1619
40. Gomez, D., Espinosa, E., Bertazzo, M., Lucas-Elio, P., Solano, F., and Sanchez-Amat, A. Appl. Microbiol. Biotechnol. 2008, 79, 925-930
41. Jiang, Z., Boyd, K. G., Mearns-Spragg, A., Adams, D. R., Wright, P. C., and Burgess, J. G. Nat. Prod. Lett. 2000, 14, 435-440
42. Lichstein, H. C. and Vandesand, V. F. J. Infect. Dis. 1945, 76, 47-51
43. Duran, N., Justo, G. Z., Ferreira, C. V., Melon, P. S., Cordi, L., and Martins, D. Biotechnol. Appl. Biochem. 2007, 48, 127-133
44. Hurdle, J. G., O'Neill, A. J., and Chopra, I. J. Antimicrob. Chemother. 2004, 54, 549-552
45. VonWittenau, M. S. and Els, H. J. Am. Chem. Soc. 1961, 83, 4678-
46. Laatsch, H., Thomson, R. H., and Cox, P. J. J. Chem. Soc., Perkin Trans. 2 1984, 1331-1339
47. Preobraz, M. N., Balashov, E. G., Turchin, K. F., Padeiska, E. N., Uvarova, N. V., Pershin, G. N., and Suvorov, N. N. Tetrahedron 1968, 24, 6131-&
48. Sutou, N., Kato, K., and Akita, H. Tetrahedron: Asymmetry 2008, 19, 1833-1838
49. Frisvad, J. C., Smedsgaard, J., Larsen, T. O., and Samson, R. A. Stud. Mycol. 2004, 201-241
50. Nielsen, K. F., Sumarah, M. W., Frisvad, J. C., and Miller, J. D. J. Agric. Food Chem. 2006, 54, 3756-3763
51. Sorensen, L. M., Nielsen, K. F., Jacobsen, T., Koch, A. G., Nielsen, P. V., and Frisvad, J. C. J. Chromatogr., A 2008, 1205, 103-108
52. Hook, D. J., Pack, E. J., Yacobucci, J. J., and Guss, J. J. Biomol. Screening 1997, 2, 145-152
53. Wagenaar, M. M. Molecules 2008, 13, 1406-1426
54. Bugni, T. S., Richards, B., Bhoite, L., Cimbora, D., Harper, M. K., and Ireland, C. M. J. Nat. Prod. 2008, 71, 1095-1098
55. Appleton, D. R., Buss, A. D., and Butler, M. S. Chimia 2007, 61, 327-331
56. Rebacz, B., Larsen, T. O., Clausen, M. H., Ronnest, M. H., Loffler, H., Ho, A. D., and Kramer, A. Cancer Res. 2007, 67, 6342-6350
57. Lang, G., Mitova, M. I., Ellis, G., Van der Sar, S., Phipps, R. K., Blunt, J. W., Cummings, N. J., Cole, A. L. J., and Munro, M. H. G. J. Nat. Prod. 2006, 69, 621-624
58. Mori, S. and Barth, H. G. Size Exclusion Chromatography, 1st ed.; Springer-Verlag: Berlin, Heidelberg, 1999.
59. Shimizu, Y. J. Nat. Prod. 1985, 48, 223-235
60. Sorensen, J. L., Nielsen, K. F., and Thrane, U. J. Agric. Food Chem. 2007, 55, 9764-9768
61. Hjelm, M., Bergh, O., Riaza, A., Nielsen, J., Melchiorsen, J., Jensen, S., Duncan, H., Ahrens, P., Birkbeck, H., and Gram, L. Syst. Appl. Microbiol. 2004, 27, 360-371
62. Gram, L., Melchiorsen, J., and Bruhn, J. B. Mar. Biotechnol. 2010, DOI: 10.1007/s10126-009-9233-y.