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.
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.
Export to BibTeX
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.
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.
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.