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dc.creatorNovaković, Miroslav M.
dc.creatorPešić, Milica
dc.creatorTrifunović, Snežana S.
dc.creatorVučković, Ivan M.
dc.creatorTodorović, Nina
dc.creatorPodolski-Renić, Ana
dc.creatorDinić, Jelena
dc.creatorStojković, Sonja
dc.creatorTešević, Vele
dc.creatorVajs, Vlatka
dc.creatorMilosavljević, Slobodan M.
dc.date.accessioned2018-11-22T00:26:58Z
dc.date.available2018-11-22T00:26:58Z
dc.date.issued2014
dc.identifier.issn0031-9422
dc.identifier.urihttp://cherry.chem.bg.ac.rs/handle/123456789/1492
dc.description.abstractAn 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. (C) 2013 Elsevier Ltd. All rights reserved.en
dc.publisherPergamon-Elsevier Science Ltd, Oxford
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172053/RS//
dc.relationinfo:eu-repo/grantAgreement/EC/FP7/256716/EU//
dc.rightsrestrictedAccess
dc.sourcePhytochemistry
dc.subjectBlack alderen
dc.subjectDiarylheptanoidsen
dc.subjectHPLC-DADen
dc.subjectNMR analysisen
dc.subjectAnti-cancer activityen
dc.subjectMulti-drug resistanceen
dc.titleDiarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cellsen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractТрифуновић, Снежана; Тешевић, Веле; Песиц, Милица; Новаковиц, Мирослав; Милосављевиц, Слободан; Стојковиц, Соња; Тодоровиц, Нина; Диниц, Јелена; Подолски-Рениц, Aна; Вајс, Влатка; Вуцковиц, Иван;
dc.citation.volume97
dc.citation.spage46
dc.citation.epage54
dc.identifier.wos000330144600006
dc.identifier.doi10.1016/j.phytochem.2013.11.001
dc.citation.other97: 46-54
dc.citation.rankM21
dc.identifier.pmid24290194
dc.description.otherSupplementary material: [http://cherry.chem.bg.ac.rs/handle/123456789/3662]
dc.type.versionpublishedVersionen
dc.identifier.scopus2-s2.0-84890436482
dc.identifier.rcubKon_2612


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