HPLC-based activity profiling: discovery of piperine as a positive GABAA receptor modulator targeting a benzodiazepine-independent binding site

Journal of Natural Products

Volumn 73, Issue 2, 2010, Pages 185-191

  Zaugg, Janine ^a,c   Baburin, Igor ^b,c   Strommer, Barbara ^b   Kim, Hyun Jung ^a   Hering, Steffen ^b   Hamburger, Matthias ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

^b Departement of Pharmacology and Toxicology   (Switzerland)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID A RECEPTOR; 4 AMINOBUTYRIC ACID A RECEPTOR STIMULATING AGENT; FLUMAZENIL; PIPERAMIDE DERIVATIVE; PIPERANINE; PIPERETTINE; PIPERINE; PIPERLONGUMININE; PLANT EXTRACT; PROTEIN SUBUNIT; TRICHOSTACHINE; UNCLASSIFIED DRUG;

ALLOSTERISM; ANIMAL CELL; ARTICLE; BLACK PEPPER; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ASSAY; CHLORIDE CONDUCTANCE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG BINDING SITE; DRUG IDENTIFICATION; DRUG RECEPTOR BINDING; DRUG SCREENING; GABAERGIC TRANSMISSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICROELECTRODE; MOLECULAR LIBRARY; NONHUMAN; OOCYTE; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; VOLTAGE CLAMP; XENOPUS LAEVIS;

ALKALOIDS; ANIMALS; BENZODIAZEPINES; BENZODIOXOLES; BINDING SITES; CHLORIDE CHANNELS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; FLUMAZENIL; FRUIT; GABA MODULATORS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OOCYTES; PIPER NIGRUM; PIPERIDINES; POLYUNSATURATED ALKAMIDES; RATS; RECEPTORS, GABA-A; XENOPUS LAEVIS;

PIPER NIGRUM; PIPERACEAE; XENOPUS LAEVIS;

EID: 77749267982     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np900656g     Document Type: Article

References (46)

1. Simon, J.; Wakimoto, H.; Fujita, N.; Lalande, M.; Barnard, E. A. J. Biol. Chem. 2004, 279, 41422-41435.
2. Olsen, R. W.; Sieghart, W. Pharmacol. Rev. 2008, 60, 243-260.
3. Barrera, N. P.; Edwardson, J. M. Trends Neurosci. 2008, 31, 569-576.
4. Sieghart, W.; Sperk, G. Curr. Top. Med. Chem. 2002, 2, 795-1616
5. Whiting, P. J. Curr. Opin. Pharmacol. 2006, 6, 24-29.
6. Riss, J.; Cloyd, J.; Gates, J.; Collins, S. Acta Neurol. Scand. 2008, 118, 69-86.
7. Johnston, G. A. R.; Hanrahan, J. R.; Chebib, M.; Duke, R. K.; Mewett, K. N. Adv. Pharmacol. 2006, 54, 286-316.
8. Tsang, S. Y.; Xue, H. Curr. Pharm. Des. 2004, 10, 1035-1044.
9. Pei, Y. Q. Epilepsia 1983, 24, 177-182.
10. Szallasi, A. Trends Pharmacol. Sci. 2005, 26, 437-439.
11. Sunila, E.; Kuttan, G. J. Ethnopharmacol. 2004, 90, 339-346.
12. Potterat, O.; Hamburger, M. Curr. Org. Chem. 2006, 10, 899-920.
13. Potterat, O.; Wagner, K.; Gemmecker, G.; Mack, J.; Puder, C.; Vettermann, R.; Streicher, R. J. Nat. Prod. 2004, 67, 1528-1531.
14. Danz, H.; Stoyanova, S.; Wippich, P.; Brattstroem, A.; Hamburger, M. Planta Med. 2001, 67, 411-416.
15. Dittmann, K.; Gerhaeuser, C.; Klimo, K.; Hamburger, M. Planta Med. 2004, 70, 909-913.
16. Kim, H. J.; Baburin, I.; Khom, S.; Hering, S.; Hamburger, M. Planta Med. 2008, 74, 521-526.
17. Baburin, I.; Beyl, S.; Hering, S. Pflug. Arch. Eur. J. Phys. 2006, 453, 117-123.
18. Chapman, J. Chapman and Hall Dictionary of Natural Products; CRC Press, Hampden Data Services Ltd., 2008.
19. Chen, J.-J.; Huang, Y.-C.; Chen, Y.-C.; Huang, S.-W.; Wang, S.-W.; Peng, C.-Y.; Teng, C.-M.; Chen, I.-S. Planta Med. 2002, 68, 980-985.
20. De Araujo-Junior, J. X.; Da-Cunha, E. V. L.; De O. Chaves, M. C.; Gray, A. I. Phytochemistry 1997, 44, 559-561.
21. Hussain, S. F.; Goezler, B.; Shamma, M.; Goezler, T. Phytochemistry 1982, 21, 2979-2980.
22. Lee, S. W.; Rho, M.-C.; Park, H. R.; Choi, J.-H.; Kang, J. Y.; Lee, J. W.; Kim, K.; Lee, H. S.; Kim, Y. K. J. Agric. Food Chem. 2006, 54, 9759-9763.
23. Min, K. R.; Kim, K.-S.; Ro, J. S.; Lee, S. H.; Kim, J. A.; Son, J. K.; Kim, Y. Planta Med. 2004, 70, 1115-1118.
24. Olsen, R. A.; Spessard, G. O. J. Agric. Food Chem. 1981, 29, 942-944.
25. Park, I.-K.; Lee, S.-G.; Shin, S.-C.; Park, J.-D.; Ahn, Y.-J. J. Agric. Food Chem. 2002, 50, 1866-1870.
26. Strunz, G. M.; Finlay, H. Tetrahedron 1994, 50, 11113.
27. Traxler, J. T. J. Agric. Food Chem. 1971, 19, 1135-1138.
28. Wu, S.; Sun, C.; Pei, S.; Lu, Y.; Pan, Y. J. Chromatogr. 2004, 1040, 193.
29. Wei, K.; Li, W.; Koike, K.; Pei, Y.; Chen, Y.; Nikaido, T. J. Nat. Prod. 2004, 67, 1005-1009.
30. Friedman, M.; Levin, C. E.; Lee, S. U.; Lee, J. S.; Ohnisi-Kameyama, M.; Kozukue, N. J. Agric. Food Chem. 2008, 56, 3028-3036.
31. Pedersen, M. E.; Metzler, B.; Stafford, G. I.; van Staden, J.; Jaeger, A. K.; Rasmussen, H. B. Molecules 2009, 14, 3833-3843.
32. Kaplan, E. M.; DuPont, R. L. Curr. Med. Res. Opin. 2005, 21, 941-950.
33. Rupprecht, R.; Eser, D.; Zwanzger, P.; Moeller, H.-J. World J. Biol. Psychiatry 2006, 7, 231-237.
34. Li, S.; Wang, C.; Li, W.; Koike, K.; Nikaido, T.; Wang, M.-W. J. Asian Nat. Prod. Res. 2007, 9, 421.
35. Wattanathorn, J.; Chonpathompikunlert, P.; Muchimapura, S.; Priprem, A.; Tankamnerdthai, O. Food Chem. Toxicol. 2008, 46, 3106-3110.
36. Hou, T. J.; Li, Y. Y.; Liao, N.; Xu, X. J. J. Mol. Model. 2000, 6, 438-445.
37. D'Hooge, R.; Pei, Y. Q.; Raes, A.; Lebrun, P.; Van Bogaert, P. P.; De Deyn, P. P. Arzneim.-Forsch. 1996, 46, 557-560.
38. Awad, R.; Ahmed, F.; Bourbonnais-Spear, N.; Mullally, M.; Ta, C. A.; Tang, A.; Merali, Z.; Maquin, P.; Caal, F.; Cal, V.; Poveda, L.; Vindas, P. S.; Trudeau, V. L.; Arnason, J. T. J. Ethnopharmacol. 2009, 125, 257-264.
39. Bajad, S.; Bedi, K. L.; Singla, A. K.; Johri, R. K. Planta Med. 2001, 67, 176-179.
40. McNamara, F. N.; Randall, A.; Gunthorpe, M. J. Br. J. Pharmacol. 2005, 144, 781-790.
41. Bhardwaj, R. K.; Glaeser, H.; Becquemont, L.; Klotz, U.; Gupta, S. K.; Fromm, M. F. J. Pharmacol. Exp. Ther. 2002, 302, 645-650.
42. Volak, L. P.; Ghirmai, S.; Cashman, J. R.; Court, M. H. Drug Metab. Dispos. 2008, 36, 1594-1605.
43. Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Adv. Drug Delivery Rev. 1997, 23, 3-25.
44. Anand, P.; Kunnumakkara, A. B.; Newman, R. A.; Aggarwal, B. B. Mol. Pharmacol. 2007, 4, 807-818.
45. Khom, S.; Baburin, I.; Timin, E. N.; Hohaus, A.; Sieghart, W.; Hering, S. Mol. Pharmacol. 2006, 69, 640-649.
46. Methfessel, C.; Witzemann, V.; Takahashi, T.; Mishina, M.; Numa, S.; Sakmann, B. Pflug. Arch. Eur. J. Phys. 1986, 407, 577-588.