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, MiroslavPešić, Milica
Trifunović, Snežana
Vučković, Ivan
Todorović, Nina
Podolski-Renic, Ana
Dinić, Jelena
Stojkovic, Sonja
Tešević, Vele
Vajs, Vlatka
Milosavljević, Slobodan
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.
Кључне речи:
Black alder / Diarylheptanoids / HPLC-DAD / NMR analysis / Anti-cancer activity / Multi-drug resistanceИзвор:
Phytochemistry, 2014, 97, 46-54Издавач:
- Oxford : Pergamon-Elsevier Science Ltd
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)
DOI: 10.1016/j.phytochem.2013.11.001
ISSN: 0031-9422
PubMed: 24290194
WoS: 000330144600006
Scopus: 2-s2.0-84890436482
Институција/група
IHTMTY - JOUR AU - Novaković, Miroslav AU - Pešić, Milica AU - Trifunović, Snežana AU - Vučković, Ivan AU - Todorović, Nina AU - Podolski-Renic, Ana AU - Dinić, Jelena AU - Stojkovic, Sonja AU - Tešević, Vele AU - Vajs, Vlatka AU - Milosavljević, Slobodan PY - 2014 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/1549 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. PB - Oxford : Pergamon-Elsevier Science Ltd 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 and Pešić, Milica and Trifunović, Snežana and Vučković, Ivan and Todorović, Nina and Podolski-Renic, Ana and Dinić, Jelena and Stojkovic, Sonja and Tešević, Vele and Vajs, Vlatka and Milosavljević, Slobodan", 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.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", 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., Pešić, M., Trifunović, S., Vučković, I., Todorović, N., Podolski-Renic, A., Dinić, J., Stojkovic, S., Tešević, V., Vajs, V.,& Milosavljević, S.. (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 Oxford : Pergamon-Elsevier Science Ltd., 97, 46-54. https://doi.org/10.1016/j.phytochem.2013.11.001
Novaković M, Pešić M, Trifunović S, Vučković I, Todorović N, Podolski-Renic A, Dinić J, Stojkovic S, Tešević V, Vajs V, Milosavljević S. 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, Pešić, Milica, Trifunović, Snežana, Vučković, Ivan, Todorović, Nina, Podolski-Renic, Ana, Dinić, Jelena, Stojkovic, Sonja, Tešević, Vele, Vajs, Vlatka, Milosavljević, Slobodan, "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 . .