Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells
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- 作者：Miroslav Novakovi膰 ; Milica Pe拧i膰 ; Sne啪ana Trifunovi膰 ; Ivan Vu膷kovi膰 ; Nina Todorovi膰 ; Ana Podolski-Reni膰 ; Jelena Dini膰 ; Sonja Stojkovi膰 ; Vele Te拧evi膰 ; Vlatka Vajs ; Slobodan Milosavljevi膰
- 关键词：Black alder ; Diarylheptanoids ; HPLC-DAD ; NMR analysis ; Anti-cancer activity ; Multi-drug resistance
- 刊名：Phytochemistry
- 出版年：January, 2014
- 年：2014
- 卷：97
- 期：Complete
- 页码：46-54
- 全文大小：468 K
文摘
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-尾-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.