Amides from Piper capense with CNS activity - A preliminary SAR analysis

Molecules

Volumn 14, Issue 9, 2009, Pages 3833-3843

  Pedersen, Mikael E ^a   Metzler, Bjørn ^a   Stafford, Gary I ^b   Van Staden, Johannes ^b   Jäger, Anna K ^a   Rasmussen, Hasse B ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF KWAZULU NATAL   (South Africa)

Author keywords

Benzodiazepine; Epilepsy; GABA; Multi target effect; Piper capense; Piperine

Indexed keywords

AMIDE;

ANIMAL; ARTICLE; CENTRAL NERVOUS SYSTEM; CHEMISTRY; DRUG EFFECT; PIPERACEAE; RAT; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; CENTRAL NERVOUS SYSTEM; PIPER; RATS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70349558295     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14093833     Document Type: Article

References (23)

1. Cacazos, J.E.; Sanchez, R. Pathophysiology of Seizures and Epilepsy. In Epilepsy; Rho, J.M., Sankar, R., Cavazos, J.E., Eds.; Marcel Dekker Inc.: New York, NY, USA, 2004.
2. Macdonald, R.L.; Meldrum, B.S. Principles of Antiepileptic Drug Action. In Antiepileptic Drugs, 4th ed.; Levy, R.H., Mattson, R.H., Meldrum, B.S., Eds.; Raven Press Ltd.: New York, NY, USA, 1995; pp. 61-79.
3. Nadkarni, S.; LaJoie, J.; Devinsky, O. Current treatments of epilepsy. Neurology 2005, S2-S11.
4. Richens, A.; Perucca, E. Clinical Pharmacology and Medical Treatment. In A Textbook of Epilepsy; Laidlaw, J., Richens, A., Chadwick, D., Eds.; Churchill Livingstone: Edinburgh, UK, 1993; pp. 495-560.
5. Van Wyk, B.E.; Gericke, N. Peoples Plants: A Guide to Useful Plants in Southern Africa; Brizza Publications: Pretoria, South Africa, 2000.
6. Stafford, G.I.; Jäger, A.K.; van Staden, J. Activity of traditional South African sedative and potentially CNS-acting plants in the GABA-benzodiazepine receptor assay. J. Ethnopharmacol. 2005, 100, 210-215.
7. De Araujo-Junior, J.O.X.; Da-Cunha, E.V.L.; Chaves, M.C.D.O.; Gray, A.I. Piperdardine, a piperidine alkaloid from Piper tuberculatum. Phytochemistry 1997, 44, 559-561.
8. Scott, I.M.; Puniani, E.; Durst, T.; Phelps, D.; Merali, S.; Assabgui, R.A.; Sànchez-Vindas, P.; Poveda, L.; Philogène, B.J.R.; Arnason, J.T. Insecticidal activity of Piper tuberculatum Jacq. extracts: synergistic interaction of piperamides. Agr. Forest Etmol. 2002, 4, 137-144.
9. Pei, Y.Q.; Tao, C. The anticonvulsant and sedative action of piperine. J. Beijing Med. College 1974, 4, 217-220.
10. Pei, Y.Q.; Yue, W.; Cui, J.; Yao, H. A study of the central pharmacological action of piperine and its derivatives. Yuo Hsueh Hsueh Puo 1980, 15, 189-205.
11. Pei, Y.Q. A review of pharmacology and clinical use of piperine and its derivatives. Epilepsia 1983, 24, 177-182.
12. Li, L.R.; Wang, S.Y. Chemical modification and structure-activity relationship studies of piperine and its analogs: An example of drug development from folk medicine. Pharmacochemistry Library 1995, 23, 321-339.
13. Dinh, L.D.; Simmen, U.; Bueter, K.B.; Bueter, B.; Lundstrom, K.; Schaffner, W. Interaction of various Piper methysticum cultivars with CNS receptors in vitro. Planta Med. 2001, 67, 306-311.
14. Yuan, C.S.; Dey, L.; Wang, A.; Mehendale, S.; Xie, J.T.; Aung, H.H.; Ang-Lee, M.K. Kavalactones and dihydrokavain modulate GABAergic activity in a rat gastric-brainstem preparation. Planta Med. 2002, 68, 1092-1096.
15. Davies, L.P.; Drew, C.A.; Duffield, P.; Johnston, G.A.R.; Jamieson, D.D. Kava pyrones and resin: studies on GABAA, GABAB and benzodiazepine binding sites in rodent brain. Pharmacol. Toxicol. 1992, 71, 120-126.
16. Schmidt, B; Ribnicky, D.M.; Poulev, A.; Logendra, S.; Cefalu, W.T.; Raskin, I. A natural history of botanical therapeutics. Metab. Clin. Exp. 2008, 57 (Suppl. 1), S3-S9.
17. Schmidt, B; Ribnicky, D.M.; Lipsky, P.E.; Raskin, I. Revisiting the ancient concept of botanical therapeutics. Nat. Chem. Biol. 2007, 3, 360-366.
18. Kahnberg, P.; Lager, E.; Rosenberg, C.; Schougaard, J.; Camet, L.; Sterner, O.; Nielsen, E.O.; Nielsen, M.; Liljefors, T. Refinement and evaluation of a pharmacophore model for flavone derivatives binding to the benzodiazepine site of the GABAA receptor. J. Med. Chem. 2002, 45, 4188-4201.
19. Pedersen, M.E.; Vestergaard, H.T.; Hansen, S.L.; Bah, S.; Diallo, D.; Jäger, A.K. Screening of Malian traditional medicine for treatment of epilepsy and convulsions. J. Ethnopharmacol. 2009, 121, 472-475.
20. Svenningsen, A.B.; Madsen, K.D.; Liljefors, T.; Stafford, G.I.; van Staden, J.; Jäger, A.K. Biflavones from Rhus species with affinity for the GABAA/benzodiazepine receptor. J. Ethnopharmacol. 2006, 103, 276-280.
21. Risa, J.; Risa, A.; Adsersen, A.; Gauguin, B.; Stafford, G.I.; van Staden, J.; Jäger, A.K. Screening of plants used in Southern Africa for epilepsy and convulsions in the GABAA-benzodiazepine receptor assay. J. Ethnopharmacol. 2004, 93, 177-182.
22. Pedersen, M.E.; Szewczyk, B.; Stachowicz, K.; Wieronska, J.; Andersen, J.; Stafford, G.I.; van Staden, J.; Pilc, A.; Jäger, A.K. Effects of South African traditional medicine in animal models for depression. J. Ethnopharmacol. 2008, 119, 542-548.
23. Das, B.; Kashinatham, A.; Venkataiah, B. Conversion of some natural dienamides to the corresponding βgamma;,y-unsaturated amides using Mg/MeOH. Synth. Commun. 1999, 29, 3799-3804.