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

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2020
Chemo-and_biocatalytic_acc_2020.pdf (993.0Kb)
Аутори
Novaković, Miroslav
Simić, Stefan
Koračak, Ljiljana
Zlatović, Mario
Ilić-Tomić, Tatjana
Asakawa, Yoshinori
Nikodinović-Runić, Jasmina
Opsenica, Igor
Чланак у часопису (Рецензирана верзија)
,
Elsevier B.V.
Метаподаци
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Апстракт
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 cancer
Извор:
Fitoterapia, 2020, 142, 104520-
Издавач:
  • Elsevier
Пројекти:
  • Биоактивни природни производи самониклих, гајених и јестивих биљака: одређивање структура и активности (RS-172053)
  • Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (RS-172008)
  • Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-173048)
Напомена:
  • This is the peer-reviewed version of the article: Novakovic, M.; Simić, S.; Koračak, L.; Zlatović, M.; Ilic-Tomic, T.; Asakawa, Y.; Nikodinovic-Runic, J.; Opsenica, I. Chemo- and Biocatalytic Esterification of Marchantin A and Cytotoxic Activity of Ester Derivatives. Fitoterapia 2020, 142. https://doi.org/10.1016/j.fitote.2020.104520
  • Published version: http://cer.ihtm.bg.ac.rs/handle/123456789/3441

DOI: 10.1016/j.fitote.2020.104520

ISSN: 0367-326X

WoS: 000528030000030

Scopus: 2-s2.0-85080118434
[ Google Scholar ]
1
1
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/3449
Колекције
  • Radovi istraživača / Researchers' publications
Институција
IHTM
TY  - 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://cer.ihtm.bg.ac.rs/handle/123456789/3449
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",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/3449",
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. Chemo- and biocatalytic esterification of marchantin A and cytotoxic activity of ester derivatives. Fitoterapia. 2020;142:104520
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.
FitoterapiaElsevier., 142, 104520.
https://doi.org/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" 142 (2020):104520,
https://doi.org/10.1016/j.fitote.2020.104520 .

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