RRC ID 67305
Author Lei J, Burgess EJ, Richardson AT, Hawkins BC, Baird SK, Smallfield BM, van Klink JW, Perry NB.
Title Cytotoxic Amides from Fruits of Kawakawa, Macropiper excelsum.
Journal Planta Med
Abstract Cytotoxic amides have been isolated from the fruits of the endemic New Zealand medicinal plant kawakawa, Macropiper excelsum (Piperaceae). The main amide was piperchabamide A and this is the first report of this rare compound outside the genus Piper. Eleven other amides were purified including two new compounds with the unusual 3,4-dihydro-1(2H)-pyridinyl group. The new compounds were fully characterized by 2D NMR spectroscopy, which showed a slow exchange between two rotamers about the amide bond, and they were chemically synthesized. In view of the antitumor activity of the related piperlongumine, all of these amides plus four synthetic analogs were tested for cytotoxicity. The most active was the piperine homolog piperdardine, with an IC50 of 14 µM against HT 29 colon cancer cells.
Volume 81(12-13)
Pages 1163-8
Published 2015-8-1
DOI 10.1055/s-0035-1546106
PMID 26039266
MeSH Alkaloids / chemistry* Alkaloids / isolation & purification Alkaloids / pharmacology Amides / chemistry* Amides / isolation & purification Amides / pharmacology Benzodioxoles / chemistry* Benzodioxoles / isolation & purification Benzodioxoles / pharmacology Cell Survival / drug effects Fruit / chemistry HT29 Cells Humans Inhibitory Concentration 50 Molecular Structure Piperaceae / chemistry* Piperidines / chemistry* Piperidines / isolation & purification Piperidines / pharmacology Plant Extracts / chemistry* Plant Extracts / isolation & purification Plant Extracts / pharmacology Plants, Medicinal Polyunsaturated Alkamides / chemistry* Polyunsaturated Alkamides / isolation & purification Polyunsaturated Alkamides / pharmacology
IF 2.687
Human and Animal Cells UBE6T-7(RCB2157)