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.
journal_name
Fitoterapiajournal_title
Fitoterapiaauthors
Novakovic M,Simić S,Koračak L,Zlatović M,Ilic-Tomic T,Asakawa Y,Nikodinovic-Runic J,Opsenica Idoi
10.1016/j.fitote.2020.104520subject
Has Abstractpub_date
2020-04-01 00:00:00pages
104520eissn
0367-326Xissn
1873-6971pii
S0367-326X(20)30102-7journal_volume
142pub_type
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