Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells
Само за регистроване кориснике
2014
Аутори
Novaković, Miroslav M.Pešić, Milica
Trifunović, Snežana S.
Vučković, Ivan M.
Todorović, Nina
Podolski-Renić, Ana
Dinić, Jelena
Stojković, Sonja
Tešević, Vele
Vajs, Vlatka
Milosavljević, Slobodan M.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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. (C) 2013 Elsevier Ltd. All rights reserved.
Кључне речи:
Black alder / Diarylheptanoids / HPLC-DAD / NMR analysis / Anti-cancer activity / Multi-drug resistanceИзвор:
Phytochemistry, 2014, 97, 46-54Издавач:
- Pergamon-Elsevier Science Ltd, Oxford
Финансирање / пројекти:
- Биоактивни природни производи самониклих, гајених и јестивих биљака: одређивање структура и активности (RS-MESTD-Basic Research (BR or ON)-172053)
- Reinforcement of the Faculty of Chemistry, University of Belgrade, towards becoming a Center of Excellence in the region of WB for Molecular Biotechnology and Food research (EU-FP7-256716)
Напомена:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3662
DOI: 10.1016/j.phytochem.2013.11.001
ISSN: 0031-9422
PubMed: 24290194
WoS: 000330144600006
Scopus: 2-s2.0-84890436482
Колекције
Институција/група
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Novaković, Miroslav M. AU - Pešić, Milica AU - Trifunović, Snežana S. AU - Vučković, Ivan M. AU - Todorović, Nina AU - Podolski-Renić, Ana AU - Dinić, Jelena AU - Stojković, Sonja AU - Tešević, Vele AU - Vajs, Vlatka AU - Milosavljević, Slobodan M. PY - 2014 UR - https://cherry.chem.bg.ac.rs/handle/123456789/1492 AB - 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. (C) 2013 Elsevier Ltd. All rights reserved. PB - Pergamon-Elsevier Science Ltd, Oxford T2 - Phytochemistry T1 - Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells VL - 97 SP - 46 EP - 54 DO - 10.1016/j.phytochem.2013.11.001 ER -
@article{ author = "Novaković, Miroslav M. and Pešić, Milica and Trifunović, Snežana S. and Vučković, Ivan M. and Todorović, Nina and Podolski-Renić, Ana and Dinić, Jelena and Stojković, Sonja and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan M.", year = "2014", 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. (C) 2013 Elsevier Ltd. All rights reserved.", publisher = "Pergamon-Elsevier Science Ltd, Oxford", journal = "Phytochemistry", title = "Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells", volume = "97", pages = "46-54", doi = "10.1016/j.phytochem.2013.11.001" }
Novaković, M. M., Pešić, M., Trifunović, S. S., Vučković, I. M., Todorović, N., Podolski-Renić, A., Dinić, J., Stojković, S., Tešević, V., Vajs, V.,& Milosavljević, S. M.. (2014). Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells. in Phytochemistry Pergamon-Elsevier Science Ltd, Oxford., 97, 46-54. https://doi.org/10.1016/j.phytochem.2013.11.001
Novaković MM, Pešić M, Trifunović SS, Vučković IM, Todorović N, Podolski-Renić A, Dinić J, Stojković S, Tešević V, Vajs V, Milosavljević SM. Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells. in Phytochemistry. 2014;97:46-54. doi:10.1016/j.phytochem.2013.11.001 .
Novaković, Miroslav M., Pešić, Milica, Trifunović, Snežana S., Vučković, Ivan M., Todorović, Nina, Podolski-Renić, Ana, Dinić, Jelena, Stojković, Sonja, Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan M., "Diarylheptanoids from the bark of black alder inhibit the growth of sensitive and multi-drug resistant non-small cell lung carcinoma cells" in Phytochemistry, 97 (2014):46-54, https://doi.org/10.1016/j.phytochem.2013.11.001 . .