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Isolation, structure elucidation and bioactivity of schischkiniin, a unique indole alkaloid from the seeds of Centaurea schischkinii |
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| Authors: | Mohammad Shoeb Marcel Jaspars Stephen M MacManus Paul K Thoo-Lin |
| Institution: | a School of Pharmacy, The Robert Gordon University, Schoolhill, Aberdeen AB10 1FR, UK b Department of Biology, Faculty of Science and Literature, Canakkale 18 Mart University, 17020 Canakkale, Turkey c Marine Natural Products Laboratory, Department of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, UK d School of Life Sciences, The Robert Gordon University, St Andrew Street, Aberdeen AB25 1HG, UK e Pharmaceutical Biotechnology Research Group, School of Biomedical Sciences, University of Ulster at Coleraine, Cromore Road, Coleraine BT52 1SA, Co. Londonderry, Northern Ireland, UK |
| Abstract: | Reversed-phase HPLC analysis of the methanol extract of the seeds of Centaurea schischkinii afforded a novel indole alkaloid, named schischkiniin (1), together with four lignans, arctiin (2), matairesinoside (3), matairesinol (4), and arctigenin (5), and three flavonoids, astragalin (6), afzelin (7) and apigenin (8). While the structure of schiskiniin (1) was established unequivocally by UV, HRFABMS and a series of 1D and 2D NMR analyses, all known compounds were readily identified by comparison of their spectroscopic data with literature data. The free radical scavenging properties of these compounds were assessed using the DPPH assay, and their general toxicity and cytotoxicity were evaluated, respectively, by brine shrimp lethality and MTT cytotoxicity assays with CaCo-2 colon cancer cell lines. Arctigenin (5) exhibited promising in vitro anticancer activity (IC50=7 μM) while with schischkiniin (1) the activity was of moderate level (IC50=76 μM). |
| Keywords: | Centaurea schischkinii Asteraceae Afzelin Apigenin Arctigenin Arctiin Astragalin Matairesinol Matairesinoside Schischkiniin DPPH assay Cytotoxiciy MTT assay Colon cancer |
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