Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
Samo za registrovane korisnike
2020
Autori
Novaković, Miroslav M.Simić, Stefan
Koračak, Ljiljana
Zlatović, Mario
Ilić-Tomič, Tatjana
Asakawa, Yoshinori
Nikodinović-Runić, Jasmina
Opsenica, Igor
Članak u časopisu (Objavljena verzija)
,
Elsevier B.V.
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
Marchantin A / Lipase / Esterification / Cytotoxicity / Cytotoxicity / Lung / cell lines / breast cancerIzvor:
Fitoterapia, 2020, 142, 104520-Izdavač:
- Elsevier
Finansiranje / projekti:
- Bioaktivni prirodni proizvodi samoniklih, gajenih i jestivih biljaka: određivanje struktura i aktivnosti (RS-MESTD-Basic Research (BR or ON)-172053)
- Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-MESTD-Basic Research (BR or ON)-172008)
- Izučavanje mikrobiološkog diverziteta i karakterizacija korisnih sredinskih mikroorganizama (RS-MESTD-Basic Research (BR or ON)-173048)
Napomena:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3889
- Peer reviewed manuscript: http://cherry.chem.bg.ac.rs/handle/123456789/3890
DOI: 10.1016/j.fitote.2020.104520
ISSN: 0367-326X
WoS: 000528030000030
Scopus: 2-s2.0-85080118434
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Novaković, Miroslav M. AU - Simić, Stefan AU - Koračak, Ljiljana AU - Zlatović, Mario AU - Ilić-Tomič, Tatjana AU - Asakawa, Yoshinori AU - Nikodinović-Runić, Jasmina AU - Opsenica, Igor PY - 2020 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3867 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 M. and Simić, Stefan and Koračak, Ljiljana and Zlatović, Mario and Ilić-Tomič, 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. M., Simić, S., Koračak, L., Zlatović, M., Ilić-Tomič, 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 MM, Simić S, Koračak L, Zlatović M, Ilić-Tomič 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 M., Simić, Stefan, Koračak, Ljiljana, Zlatović, Mario, Ilić-Tomič, 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 . .