Amides from Piper capense with CNS activity: a preliminary SAR analysis

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Mikael Egebjerg Pedersen, Bjørn Metzler, Gary Ivan Stafford, Johannes van Staden, Anna Katharina Jäger, Hasse Bonde Rasmussen

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 GABA(A) receptor (IC(50) 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.
Original languageEnglish
JournalMolecules
Volume14
Issue number9
Pages (from-to)3833-3843
ISSN1420-3049
DOIs
Publication statusPublished - 2009

Bibliographical note

Keywords: Piper capense; piperine; GABA; benzodiazepine; epilepsy; multi target effect

ID: 14856700