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Accelerated dereplication of crude extracts using HPLC-PDA-MS-SPE-NMR: Quinolinone alkaloids of Haplophyllum acutifolium |
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| Authors: | Dan Staerk Julie R Kesting Matthias Witt Seyed A Emami |
| Institution: | a Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, Universitetsparken 2, DK-2100 Copenhagen, Denmark b Department of Basic Sciences and Environment, Faculty of Life Sciences, University of Copenhagen, Thorvaldsensvej 40, DK-1871 Frederiksberg, Denmark c Bruker Daltonik GmbH, Fahrenheitstrasse 4, D-28359 Bremen, Germany d Department of Pharmacognosy, School of Pharmacy, Mashhad University of Medical Sciences, P.O. Box 91775-1365, Mashhad, Iran |
| Abstract: | 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 IC50 values of 2.17 ± 0.22 μM and 3.79 ± 0.24 μM, respectively (chloroquine-sensitive Plasmodium falciparum 3D7 strain). |
| Keywords: | Haplophyllum acutifolium Haplohpyllum perforatum Rutaceae HPLC-PDA-MS-SPE-NMR Haplacutines A-F NMR Dereplication |
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