Molecules 2009, 14(9), 3833-3843; doi:10.3390/molecules14093833
Communication

Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis

1email, 1email, 2email, 2email, 1email and 1,* email
Received: 8 September 2009; in revised form: 25 September 2009 / Accepted: 25 September 2009 / Published: 25 September 2009
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Piper capense L.f. (Piperaceae) is used traditionally in South Africa as a sleep inducing remedy. Bioassay-guided fractionation of the roots of P. capense led to the isolation of piperine (1) and 4,5-dihydropiperine (2), which showed moderate affinity for the benzodiazepine site on the GABAA receptor (IC50 values of 1.2 mM and 1.0 mM, respectively). The present study suggests that strict structural properties of the amides are essential for affinity. Taken together, these observations suggest that the carbon chain must contain not less than four carbons, and that a conjugated double bond, adjacent to the amide group, is necessary for binding to the receptor and that the amine part should be bulky.
Keywords: Piper capense; piperine; GABA; benzodiazepine; epilepsy; multi target effect
PDF Full-text Download PDF Full-Text [322 KB, uploaded 18 June 2014 19:30 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

Pedersen, M.E.; Metzler, B.; Stafford, G.I.; Van Staden, J.; Jäger, A.K.; Rasmussen, H.B. Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis. Molecules 2009, 14, 3833-3843.

AMA Style

Pedersen ME, Metzler B, Stafford GI, Van Staden J, Jäger AK, Rasmussen HB. Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis. Molecules. 2009; 14(9):3833-3843.

Chicago/Turabian Style

Pedersen, Mikael E.; Metzler, Bjørn; Stafford, Gary I.; Van Staden, Johannes; Jäger, Anna K.; Rasmussen, Hasse B. 2009. "Amides from Piper capense with CNS Activity – A Preliminary SAR Analysis." Molecules 14, no. 9: 3833-3843.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert