Isolation, structure elucidation and bioactivity of schischkiniin, a unique indole alkaloid from the seeds of Centaurea schischkinii

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dc.authoridKong Thoo Lin, Paul/0000-0002-7090-246X
dc.authoridNahar, Prof Lutfun/0000-0002-1157-2405
dc.authoridJaspars, Marcel/0000-0002-2426-6028
dc.authoridShoeb, Mohammad/0000-0002-9486-2749
dc.contributor.authorShoeb, M
dc.contributor.authorCelik, S
dc.contributor.authorJaspars, M
dc.contributor.authorKumarasamy, Y
dc.contributor.authorMacManus, SM
dc.contributor.authorNahar, L
dc.contributor.authorPaul, KTLD
dc.date.accessioned2025-01-27T20:24:51Z
dc.date.available2025-01-27T20:24:51Z
dc.date.issued2005
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractReversed-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 ID 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 mu M) while with schischkiniin (1) the activity was of moderate level (IC50 = 76 mu M). (c) 2005 Elsevier Ltd. All rights reserved.
dc.identifier.doi10.1016/j.tet.2005.07.047
dc.identifier.endpage9006
dc.identifier.issn0040-4020
dc.identifier.issue38
dc.identifier.scopus2-s2.0-23944438094
dc.identifier.scopusqualityQ3
dc.identifier.startpage9001
dc.identifier.urihttps://doi.org/10.1016/j.tet.2005.07.047
dc.identifier.urihttps://hdl.handle.net/20.500.12428/22364
dc.identifier.volume61
dc.identifier.wosWOS:000231661700003
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherPergamon-Elsevier Science Ltd
dc.relation.ispartofTetrahedron
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectCentaurea schischkinii
dc.subjectAsteraceae
dc.subjectafzelin
dc.subjectapigenin
dc.subjectarctigenin
dc.subjectarctiin
dc.subjectastragalin
dc.subjectmatairesinol
dc.subjectmatairesinoside
dc.subjectschischkiniin
dc.subjectDPPH assay
dc.subjectcytotoxiciy
dc.subjectMTT assay
dc.subjectcolon cancer
dc.titleIsolation, structure elucidation and bioactivity of schischkiniin, a unique indole alkaloid from the seeds of Centaurea schischkinii
dc.typeArticle

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