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Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells
dc.creator | Novaković, Miroslav | |
dc.creator | Pešić, Milica | |
dc.creator | Trifunović, Snežana | |
dc.creator | Vučković, Ivan | |
dc.creator | Todorović, Nina | |
dc.creator | Podolski-Renic, Ana | |
dc.creator | Dinić, Jelena | |
dc.creator | Stojkovic, Sonja | |
dc.creator | Tešević, Vele | |
dc.creator | Vajs, Vlatka | |
dc.creator | Milosavljević, Slobodan | |
dc.date.accessioned | 2019-01-30T17:41:58Z | |
dc.date.available | 2019-01-30T17:41:58Z | |
dc.date.issued | 2014 | |
dc.identifier.issn | 0031-9422 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1549 | |
dc.description.abstract | An extended study of minor diarylheptanoids from the bark of black alder has resulted in the isolation of twenty diarylheptanoids, ten of which have not previously been reported (14-18, 20-24). The structures and configurations of all compounds were elucidated by NMR, HRESIMS, UV, IR, and CD. The anti-cancer potency of twenty diarylheptanoids and four previously isolated compounds (7, 10, 12, 13) was investigated in human non-small cell lung carcinoma cell lines (sensitive and multi-drug resistant variants) as well as in normal human keratinocytes. Diarylheptanoids with a p-coumaroyl group, 14 and 18, platyphylloside (1), platyphyllonol-5-O-beta-D-xylopyranoside (2), alnuside B (4) and hirsutenone (9) exhibited strong anti-cancer activity, considerably higher than diarylheptanoid curcumin, which served as a positive control. Compounds 4, 9, 14, and 18 displayed significant selectivity towards the cancer cells. Structure/activity analysis of twenty-four closely related diarylheptanoids revealed a high dependence of cytotoxic action on the presence of a carbonyl group at C-3. Substitution of a heptane chain on C-5 and a number of hydroxyl groups in the aromatic rings also emerged as a significant structural feature that influenced their cytotoxic potential. | en |
dc.publisher | Oxford : Pergamon-Elsevier Science Ltd | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172053/RS// | |
dc.relation | info:eu-repo/grantAgreement/EC/FP7/256716/EU// | |
dc.rights | restrictedAccess | |
dc.source | Phytochemistry | |
dc.subject | Black alder | en |
dc.subject | Diarylheptanoids | en |
dc.subject | HPLC-DAD | en |
dc.subject | NMR analysis | en |
dc.subject | Anti-cancer activity | en |
dc.subject | Multi-drug resistance | en |
dc.title | Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells | en |
dc.type | article | |
dc.rights.license | ARR | |
dc.citation.volume | 97 | |
dc.citation.spage | 46 | |
dc.citation.epage | 54 | |
dc.citation.other | 97: 46-54 | |
dc.citation.rank | M21 | |
dc.identifier.pmid | 24290194 | |
dc.identifier.doi | 10.1016/j.phytochem.2013.11.001 | |
dc.identifier.scopus | 2-s2.0-84890436482 | |
dc.identifier.wos | 000330144600006 | |
dc.type.version | publishedVersion |