Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives
Authorized Users Only
2020
Authors
Novaković, Miroslav
Simić, Stefan

Koračak, Ljiljana
Zlatović, Mario

Ilić-Tomić, Tatjana

Asakawa, Yoshinori

Nikodinović-Runić, Jasmina

Opsenica, Igor

Article (Published version)

Elsevier B.V.
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Show full item recordAbstract
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.
Keywords:
Marchantin A / Lipase / Esterification / Cytotoxicity / Cytotoxicity / Lung / cell lines / breast cancerSource:
Fitoterapia, 2020, 142, 104520-Publisher:
- Elsevier
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
- The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-172008)
- Microbial diversity study and characterization of beneficial environmental microorganisms (RS-173048)
Note:
- 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
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Institution/Community
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 . .