Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: Potent V-ATPase inhibitory polyketides from the Myxobacteria cystobacter violaceus and Archangium gephyra

Journal of Natural Products

Volumn 74, Issue 5, 2011, Pages 1100-1105

  Horstmann, Nicole ^b   Essig, Sebastian ^a   Bockelmann, Svenja ^d   Wieczorek, Helmut ^d   Huss, Markus ^d   Sasse, Florenz ^c   Menche, Dirk ^a,b  

^a UNIVERSITY OF HEIDELBERG   (Germany)

^b HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^c Abteilung Chemische Biologie   (Germany)

^d UNIVERSITY OF OSNABRÜCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE TRIPHOSPHATE DEPENDENT PROTEINASE; ARCHAZOLID A 15 O BETA DEXTRO GLUCOPYRANOSIDE; ISO ARCHAZOLID B; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; VACUOLAR TYPE ATPASE;

ANIMAL CELL; ANIMAL CELL CULTURE; ARCHANGIUM GEPHYRA; ARTICLE; BACTERIAL STRAIN; CANCER CELL CULTURE; CARBON NUCLEAR MAGNETIC RESONANCE; CYSTOBACTER VIOLACEUS; CYTOTOXICITY; DEGRADATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; IC 50; MOUSE; MYXOCOCCALES; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; GLUCOSIDES; HUMANS; INHIBITORY CONCENTRATION 50; MACROLIDES; MALE; MICE; MOLECULAR STRUCTURE; MYXOCOCCALES; THIAZOLES; VACUOLAR PROTON-TRANSLOCATING ATPASES;

ARCHANGIUM GEPHYRA; CYSTOBACTER VIOLACEUS; MYXOCOCCALES;

EID: 79957808872     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200036v     Document Type: Article

References (38)

1. Beyenbach, K. W.; Wieczorek, H. J. Exp. Biol. 2006, 209, 577-589.
2. Nishi, T.; Forgac, M. Nat. Rev. Mol. Cell Biol. 2002, 3, 94-103.
3. Jefferies, K. C.; Cipriano, D. J.; Forgac, M. Arch. Biochem. Biophys. 2008, 476, 33-42.
4. Maxfield, F. R.; McGraw, T. E. Nat. Rev. Mol. Cell Biol. 2004, 5, 121-132.
5. Hiesinger, P. R.; Fayyazuddin, A.; Mehta, S. Q.; Rosenmund, T.; Schulze, K. L.; Zhai, R. G.; Verstreken, P.; Cao, Y.; Zhou, Y.; Kunz, J.; Bellen, H. J. Cell 2005, 121, 607-620.
6. Wagner, C. A.; Finberg, K. E.; Breton, S.; Marshansky, V.; Brown, D.; Geibel, J. P. Physiol. Rev. 2004, 84, 1263-1314.
7. Brown, D.; Paunescu, T. G.; Breton, S.; Marshansky, V. J. Exp. Biol. 2009, 212, 1762-1772.
8. Toyomura, T.; Murata, Y.; Yamamoto, A.; Oka, T.; Sun-Wada, G. H.; Wada, Y.; Futai, M. J. Biol. Chem. 2003, 278, 22023-22030.
9. Pietrement, C.; Sun-Wada, G. H.; Silva, N. D.; McKee, M.; Marshansky, V.; Brown, D.; Futai, M.; Breton, S. Biol. Reprod. 2006, 74, 185-194.
10. Forgac, M. Nat. Rev. Mol. Cell Biol. 2007, 8, 917-929.
11. Niikura, K. Drug News Perspect. 2006, 19, 139-144.
12. Perez-Sayans, M.; Somoza-Martin, J. M.; Barros-Angueira, F.; Rey, J. M.; Garcia-Garcia, A. Cancer Treat. Rev. 2009, 35, 707-713.
13. Huss, M.; Wieczorek, H. J. Exp. Biol. 2009, 212, 341-346.
14. Höfle, G. R., H.; Sasse, F.; Steinmetz, H. German Patent DE 41 42 951 C1, 1993.
15. For general reviews on polyketides from myxobacteria, see: (a) Menche, D. Nat. Prod. Rep. 2008, 25, 905-918.
16. (b) Weissman, K. J.; Müller, R. Nat. Prod. Rep. 2010, 27, 1276-1295.
17. Sasse, F.; Steinmetz, H.; Hofle, G.; Reichenbach, H. J. Antibiot. 2003, 56, 520-525.
18. Huss, M.; Sasse, F.; Kunze, B.; Jansen, R.; Steinmetz, H.; Ingenhorst, G.; Zeeck, A.; Wieczorek, H. BMC Biochem. 2005, 6, 13.
19. Murata, T.; Yamato, I.; Kakinuma, Y.; Leslie, A. G.; Walker, J. E. Science 2005, 308, 654-659.
20. Muench, S. P.; Huss, M.; Song, C. F.; Phillips, C.; Wieczorek, H.; Trinick, J.; Harrison, M. A. J. Mol. Biol. 2009, 386, 989-999.
21. Bockelmann, S.; Menche, D.; Rudolph, S.; Bender, T.; Grond, S.; von Zezschwitz, P.; Muench, S. P.; Wieczorek, H.; Huss, M. J. Biol. Chem. 2010, 285, 38304-38314.
22. Menche, D.; Hassfeld, J.; Steinmetz, H.; Huss, M.; Wieczorek, H.; Sasse, F. J. Antibiot. 2007, 60, 328-331.
23. Menche, D.; Hassfeld, J.; Steinmetz, H.; Huss, M.; Wieczorek, H.; Sasse, F. Eur. J. Org. Chem. 2007, 1196-1202.
24. Hassfeld, J.; Farès, C.; Steinmetz, H.; Carlomagno, T.; Menche, D. Org. Lett. 2006, 8, 4751-4754.
25. Menche, D.; Hassfeld, J.; Li, J.; Rudolph, S. J. Am. Chem. Soc. 2007, 129, 6100-6101.
26. Menche, D.; Hassfeld, J.; Li, J.; Mayer, K.; Rudolph, S. J. Org. Chem. 2009, 74, 7220-7229.
27. Roethle, P. A.; Chen, I. T.; Trauner, D. J. Am. Chem. Soc. 2007, 129, 8960-8961.
28. Menche, D.; Hassfeld, J.; Sasse, F.; Huss, M.; Wieczorek, H. Bioorg. Med. Chem. Lett. 2007, 17, 1732-1735.
29. Saroussi, S.; Nelson, N. J. Exp. Biol. 2009, 212, 1604-1610.
30. iso-Archazolid B (6) can be detected directly in the fermentation broth before isolation, which suggests that it presents an authentic natural product and not an isolation artifact derived from archazolid B. Isomerization during extraction or detection likewise seems highly unlikely, as this has never been detected for the archazolid family under such conditions (see refs 16, 21-27). A related double-bond migration has been observed only for a ring-opened derivative but not for the macrocyclic metabolites. Also, this isomerization has occurred only under basic conditions but not under the neutral pH values present during fermentation (see ref 23). Therefore an isomerization is much more likely before ring-closure, i.e., during the biosynthesis of isoarchazolid B.
31. For leading references on the biosynthesis of myxobacterial polyketides and polyketides in general, see: (a) Staunton, J.; Weissman, K. J. Nat. Prod. Rep. 2001, 18, 380-416.
32. (b) Wenzel, S. C.; Muller, R. Nat. Prod. Rep. 2009, 26, 1385-1407.
33. (c) Hertweck, C. Angew. Chem., Int. Ed. 2009, 48, 4688-4716.
34. Fares, C.; Hassfeld, J.; Menche, D.; Carlomagno, T. Angew. Chem., Int. Ed. 2008, 47, 3722-3726.
35. Chaplin, M. F. Anal. Biochem. 1982, 123, 336-341.
36. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63.
37. Huss, M.; Ingenhorst, G.; Konig, S.; Gassel, M.; Drose, S.; Zeeck, A.; Altendorf, K.; Wieczorek, H. J. Biol. Chem. 2002, 277, 40544-40548.
38. Wieczorek, H.; Cioffi, M.; Klein, U.; Harvey, W. R.; Schweikl, H.; Wolfersberger, M. G. Methods Enzymol. 1990, 192, 608-616.