Identification of secondary metabolites from Streptomyces violaceoruber TÜ22 by means of on-flow LC-NMR and LC-DAD-MS

Magnetic Resonance in Chemistry

Volumn 43, Issue 9, 2005, Pages 710-723

  Pham, L H ^a   Vater, J ^a   Rotard, W ^a   Mugge C ^b  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

HPLC PDA; LC DAD MS and MS MS; LC NMR; MALDI TOF MS; Microorganisms; Polyketides; Secondary metabolites; Streptomyces violaceruber T 22

Indexed keywords

BACTERIA; BIOMOLECULES; FLAVONOIDS; INDUCTIVELY COUPLED PLASMA; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

HPLC- PDA; LC-DAD-MS AND -MS/MS; LC-NMR; MALDI TOF MS; NATURAL PRODUCTS; ON-FLOW LC-NMR; POLYKETIDES; RAPID SCREENING; SECONDARY METABOLITES; STREPTOMYCES VIOLACERUBE TÜ22;

METABOLITES;

EID: 23644456560     PISSN: 07491581     EISSN: None     Source Type: Journal    
DOI: 10.1002/mrc.1633     Document Type: Article

References (73)

1. Lindon JC, Nicholson JK, Wilson ID. J. Chromatogr., B 2000; 748: 233.
2. Lee MS, Kerns EH. Mass Spectrom. Rev. 1999; 18: 187.
3. Shin YG, Van Breemen RB. Biopharm. Drug Dispos. 2001; 22: 353.
4. Johnson S, Morgan ED, Wilson ID, Spraul M, Hofmann M. J. Chem. Soc., Perkin Trans. 1 1994; 1499.
5. Albert K, Schlotterbeck G, Braumann U, Händel H, Spraul M, Krack G. Angew. Chem. 1995; 107: 1102.
6. Höltzel A, Schlotterbeck G, Albert K, Bayer E. Chromatographia 1996; 42: 499.
7. Spring O, Buschmann H, Vogler B, Schilling EE, Spraul M, Hofmann M. Phytochemistry 1995; 39: 609.
8. Pham LH. 'Isolierung und Struckturaufklärung von Alkaloiden aus Hippeastrum equestre Herb. und Crinum amabile Donn. vietnamesischer Herkunft' Dissertation, Institute of Chemistry, Humboldt University Berlin, 1997.
9. Hostettmann K, Wolfender J-L. Pestic. Sci. 1997; 51: 299.
10. Hostettmann K, Wolfender J-L, Rodriguez S. Planta Med. 1997; 63: 2.
11. Wolfender J-L, Rodriguez S, Hostettmann K, Hiller W. Phytochem. Anal. 1997; 8: 97.
12. Spring O, Hell N, Vogler B. Phytochemistry 1997; 46: 1369.
13. Bringmann G, Günther C, Schlauer J, Rückert M. Anal. Chem. 1998; 70: 2805.
14. Garo E, Wolfender J-L, Hostettmann K, Hiller W, Antus S, Mavi S. Helv. Chim. Acta 1998; 81: 754.
15. Rodriguez S, Wolfender J-L, Stoeckli-Evans H, Gupta MP, Hostettmann K. Helv. Chim. Acta 1998; 81: 1393.
16. Wolfender J-L, Rodriguez S, Hostettmann K. J. Chromatogr., A 1998; 794: 299.
17. Wilson ID, Morgan ED, Lafont R, Wright BA. J. Chromatogr., A 1998; 799: 333.
18. Vogler B, Klaiber I, Roos G, Walter CU, Hiller W, Sandor P, Kraus WJ. J. Not. Prod. 1998; 61: 175.
19. Cavin A, Pofterat O, Wolfender J-L, Hostettmann K, Dyatmyko W. J. Nat. Prod. 1998; 61: 1497.
20. Schneider B, Zhao Y, Blitzke T, Schmitt B, Nookandeh A, Sun X, Stöckigt J. Phytochem. Anal. 1998; 9: 237.
21. Strohschein S, Rentel C, Lacker T, Bayer E, Albert K. Anal. Chem. 1999; 71: 1780.
22. Bringmann G, Messer K, Wohlfahrt M, Kraus J, Dumbuya K, Rückert M. Anal. Chem. 1999; 71: 2678.
23. Hansen SH, Jensen AG, Cornett C, Bjornsdottir I, Taylor S, Wright B, Wilson ID. Anal. Chem. 1999; 71: 5235.
24. Wilson ID, Morgan ED, Lafont R, Shockor JP, Lindon JC, Nicholson JK, Wright B. Chromatographia 1999; 49: 374.
25. Bringmann G, Rückert M, Messer K, Schupp O, Louis AM. J. Chromatogr., A 1999; 837: 267.
26. Renupka T, Roos G, Klaiber I, Vogler B, Kraus W. J. Chromatogr., A 1999; 847: 109.
27. Pusecker K, Albert K, Bayer E. J. Chromatogr., A 1999; 836: 245.
28. Zhao Y, Nookandeh A, Schneider B, Sun X, Schmitt B, Stöckigt J. J. Chromatogr., A 1999; 837: 83.
29. Ndjoko K, Wolfender J-L, Röder E, Hostettmann K. Planta Med. 1999; 65: 562.
30. Ioset JR, Wolfender JL, Marston A, Gupta MP, Hostettmann K. Phytochem. Anal. 1999; 10: 137.
31. Hölscher D, Schneider B. Phytochemistry 1999; 50: 155.
32. Kleinwächter P, Luhmaan U, Schlegel B, Heinze S, Härtl A, Kiet TT, Gräfe U. J. Basic Microbiol. 1999; 39: 345.
33. Lommen A, Godejohann M, Venema DP, Hollmann PHC, Spraul M. Anal. Chem. 2000; 72: 1793.
34. Ferrari J, Terteaux C, Wolfender J-L, Hostettmann K. Chimia 2000; 54: 406.
35. Santos LC, Dachtler M, Andrade FDP, Albert K, Vilegas W. Fresenius' J. Anal. Chem. 2000; 368: 540.
36. Vilegas W, Vilegas JH, Dachtler M, Glaser T, Albert K. Phytochem. Anal. 2000; 11: 317.
37. Dachtler M, Glaser T, Kohler K, Albert K. Anal. Chem. 2001; 73: 667.
38. Bringmann G, Wohlfarth M, Rischer H, Heubes M, Saeb W, Diem S, Herderich M, Schauer J. Anal. Chem. 2001; 73: 2571.
39. Louden D, Handley A, Taylor S, Lenz E, Miller S, Wilson ID, Sage A, Lafont R. J. Chromatogr., A 2001; 910: 237.
40. Wolfender JL, Ndjoko K, Hostettmann K. Phytochem. Anal. 2001; 12: 2.
41. Gavidia I, Seitz HU, Pérez-Bermúdez P, Vogler B. Phytochem. Anal. 2002; 13: 266.
42. Dachtler M, Van de Put FHM, von Stijn F, Beindorff CM, Fritsche J. Eur. J. Lipid Sci. Technol. 2003; 105: 488.
43. Guilet D, Guntern A, Ioset JR, Queroz EF, Ndjoko K, Foggin CM, Hostettmann K. J. Nat. Prod. 2003; 66: 17.
44. Queiroz EF, Wolfender JL, Raoelison G, Hostettmann K. Phytochem. Anal. 2003; 14: 34.
45. Setzer WN, Vogler B, Bates RB, Schmidt JM, Dicus CW, Nakkiew P, Haber WA. Phytochem. Anal. 2003; 14: 54.
46. Cogne AL, Queiroz EF, Wolfender JL, Marston A, Mavi S, Hostettmann K. Phytochem. Anal. 2003; 14: 67.
47. Karagianis G, Viljoen A, Wattermann PG. Phytochem. Anal. 2003; 14: 275.
48. Wolfender JL, Verotta L, Belvisi L, Fuzzati N, Hostettmann K. Phytochem. Anal. 2003; 14: 290.
49. Unger M, Dreyer M, Specker S, Laug S, Pelzing M, Neusüss C, Holzgrabe U, Bringmann G. Phytochem. Anal. 2004; 15: 21.
50. Gaub M, von Brocke A, Roos G, Kovar KA. Phytochem. Anal. 2004; 15: 300.
51. De Rijke E, De Kanter F, Ariese F, Brinkman UAT, Gooijer C. J. Sep. Sci. 2004; 27: 1061.
52. Cannell RJP, Rashid T, Ismail IM, Sidebottom PJ, Knaggs AR, Marsall PS. Xenobiotica 1997; 27: 147.
53. Abel CBL, Lindon JC, Noble D, Rudd BAM, Sidebottom PJ, Nicholson JK. Anal. Biochem. 1999; 270: 220.
54. Bobzin SC, Yang S, Kasten TP. J. Chromatogr., B 2000; 748: 259.
55. Kleinwächter P, Martin K, Groth I, Dornberger K. J. High Resolut. Chromatogr. 2000; 23: 609.
56. Sandvoss M, Pham LH, Levsen K, Preiss A, Muegge C, Wuensch G. Eur. J. Org. Chem. 2000; 1253.
57. Sandvoss M, Weltring W, Preiss A, Levsen K, Wuensch G. J. Chromatogr., A 2001; 917: 75.
58. Sandvoss M, Preiss A, Levsen K, Weismann R, Spraul M. Magn. Reson. Chem. 2003; 41: 949.
59. Duarte IF, Godejohann M, Braumann U, Spraul M, Gil A. J. Agric. Food Chem. 2003; 51: 4847.
60. Niessen WMA. J. Chromatogr., A 1999; 856: 179.
61. Sandvoss M. 'LC-NMR for Natural Products Analysis'. In On-line LC-NMR and related techniques, Albert K (ed). John Wiley & Sons: 2002.
62. Pham LH, Mügge C, Krause E, Zaspel I, Zocher R. Rapid identification of metabolites in the extract of Fusarium sambucinum by using a combination of MALDI-MS, LC-PDA-MS and LC-NMR (in preparation July 2005).
63. Pham LH, Mügge C, Zocher R, Ly HK, Veth J, Zocher R. Rapid identification of intermediates of ozonolysed ethidium bromide by using a combination of LC-PDA-MS and LC-NMR (in preparation July 2005).
64. Leenders F, Stein TH, Kablitz B, Frank P, Vater J. Rapid Commun. Mass Spectrom. 1999; 13: 943.
65. Russell DH, Edmondson RD. J. Mass Spectrom. 1997; 32: 263.
66. Corbaz R, Ettlinger L, Gäumann E, Kalvoda J, Keller-Schierlein W, Kradolfer F, Manukian BK, Neipp L, Prelog V, Reusser P, Zähner H. Helv. Chim. Acta 1957; 40: 1262.
67. Keller-Schierlein W, Brufani M, Barcza S. Helv. Chim. Acta 1968; 51: 1257.
68. Brufani M, Dobler M. Helv. Chim. Acta 1968; 51: 1269.
69. Krone B, Zeeck A. Liebigs Ann. Chem. 1987; 1987: 751.
70. Sherman DH, Malpartida F, Bibb MJ, Kieser HM, Bibb MJ, Hopwood DA. EMBO J. 1989; 8: 2717.
71. Maehr H. Monatsh. Chem. 1979; 110: 531.
72. Markham KR, Mabry TJ. Phytochemistry 1968; 7: 791.
73. Barcza S, Brufani M, Keller-Schierlein W, Zähner H. Helv. Chim. Acta 1966; 49: 1736.