Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
Само за регистроване кориснике
2020
Аутори
Novaković, MiroslavSimić, Stefan
Koračak, Ljiljana
Zlatović, Mario
Ilić-Tomić, Tatjana
Asakawa, Yoshinori
Nikodinović-Runić, Jasmina
Opsenica, Igor
Чланак у часопису (Објављена верзија)
,
Elsevier B.V.
Метаподаци
Приказ свих података о документуАпстракт
Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME...3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.
Кључне речи:
Marchantin A / Lipase / Esterification / Cytotoxicity / Cytotoxicity / Lung / cell lines / breast cancerИзвор:
Fitoterapia, 2020, 142, 104520-Издавач:
- Elsevier
Финансирање / пројекти:
- Биоактивни природни производи самониклих, гајених и јестивих биљака: одређивање структура и активности (RS-MESTD-Basic Research (BR or ON)-172053)
- Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (RS-MESTD-Basic Research (BR or ON)-172008)
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-MESTD-Basic Research (BR or ON)-173048)
Напомена:
- The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/3449
DOI: 10.1016/j.fitote.2020.104520
ISSN: 0367-326X
WoS: 000528030000030
Scopus: 2-s2.0-85080118434
URI
http://cherry.chem.bg.ac.rs/handle/123456789/3867https://cer.ihtm.bg.ac.rs/handle/123456789/3441
Институција/група
IHTMTY - JOUR AU - Novaković, Miroslav AU - Simić, Stefan AU - Koračak, Ljiljana AU - Zlatović, Mario AU - Ilić-Tomić, Tatjana AU - Asakawa, Yoshinori AU - Nikodinović-Runić, Jasmina AU - Opsenica, Igor PY - 2020 UR - http://cherry.chem.bg.ac.rs/handle/123456789/3867 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/3441 AB - Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A. PB - Elsevier T2 - Fitoterapia T1 - Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives VL - 142 SP - 104520 DO - 10.1016/j.fitote.2020.104520 ER -
@article{ author = "Novaković, Miroslav and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomić, Tatjana and Asakawa, Yoshinori and Nikodinović-Runić, Jasmina and Opsenica, Igor", year = "2020", abstract = "Chemical and biocatalytic synthesis of seven previously undescribed marchantin A ester derivatives has been presented. Chemical synthesis afforded three peresterified bisbibenzyl products (TE1-TE3), while enzymatic method, using lipase, produced regioselective monoester derivatives (ME1-ME4). The antiproliferative activities of all prepared derivatives of marchantin A were tested on MRC-5 healthy human lung fibroblast, A549 human lung cancer, and MDA-MB-231 human breast cancer cell lines. All tested esters were less cytotoxic in comparison to marchantin A, but they also exhibited lower cytotoxicity against healthy cells. Monoesters displayed higher cytotoxic activities than the corresponding peresterified products, presumably due to the presence of free catechol group. Monohexanoyl ester ME3 displayed the same IC50 like marchantin A against MDA-MB-231 cells, but the selectivity was higher. In this way, regioselective enzymatic monoesterification enhanced selectivity of marchantin A. ME3 was also the most active among all derivatives against lung cancer cells A549 with the slightly lower activity and selectivity in comparison to marchantin A.", publisher = "Elsevier", journal = "Fitoterapia", title = "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives", volume = "142", pages = "104520", doi = "10.1016/j.fitote.2020.104520" }
Novaković, M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomić, T., Asakawa, Y., Nikodinović-Runić, J.,& Opsenica, I.. (2020). Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia Elsevier., 142, 104520. https://doi.org/10.1016/j.fitote.2020.104520
Novaković M, Simić S, Koračak L, Zlatović M, Ilić-Tomić T, Asakawa Y, Nikodinović-Runić J, Opsenica I. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. in Fitoterapia. 2020;142:104520. doi:10.1016/j.fitote.2020.104520 .
Novaković, Miroslav, Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomić, Tatjana, Asakawa, Yoshinori, Nikodinović-Runić, Jasmina, Opsenica, Igor, "Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives" in Fitoterapia, 142 (2020):104520, https://doi.org/10.1016/j.fitote.2020.104520 . .