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Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives

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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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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. 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 cancer
Source:
Fitoterapia, 2020, 142, 104520-
Publisher:
  • Elsevier
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
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URI
http://cherry.chem.bg.ac.rs/handle/123456789/3867
http://cer.ihtm.bg.ac.rs/handle/123456789/3441
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