Accelerated dereplication of crude extracts using HPLC-PDA-MS-SPE-NMR: quinolinone alkaloids of Haplophyllum acutifolium.
Direct hyphenation of analytical-scale high-performance liquid chromatography, photo-diode array detection, mass spectrometry, solid-phase extraction and nuclear magnetic resonance spectroscopy (HPLC-PDA-MS-SPE-NMR) has been used for accelerated dereplication of crude extract of Haplophyllum acutifolium (syn. Haplophyllum perforatum). This technique allowed fast on-line identification of six quinolinone alkaloids, named haplacutine A-F, as well as of acutine, haplamine, eudesmine, and 2-nonylquinolin-4(1H)-one. Acutine and haplacutine E, isolated by preparative-scale HPLC, showed moderate antiplasmodial activity with IC(50) values of 2.17+/-0.22 microM and 3.79+/-0.24 microM, respectively (chloroquine-sensitive Plasmodium falciparum 3D7 strain).
Staerk
Dan
D
Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark. dst@life.ku.dk
Kesting
Julie R
JR
Sairafianpour
Majid
M
Witt
Matthias
M
Asili
Javad
J
Emami
Seyed A
SA
Jaroszewski
Jerzy W
JW
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D000818:Animals; D002738:Chloroquine / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D004351:Drug Resistance / Q000187:drug effects; D007492:Iran; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010963:Plasmodium falciparum / Q000187:drug effects; D015363:Quinolones / Q000737:chemistry / Q000302:isolation & purification*; D027821:Rutaceae / Q000737:chemistry*
D000470:Alkaloids; D015363:Quinolones; D002738:Chloroquine