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Bisaurones-enzymatic production and biological evaluation

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2020
ACC_d0nj00758g.pdf (1.234Mb)
Authors
Novaković, Miroslav
Ilić-Tomić, Tatjana
Tešević, Vele
Simić, Katarina
Ivanović, Stefan
Simić, Stefan
Opsenica, Igor
Nikodinović-Runić, Jasmina
Article (Accepted Version)
,
Royal Society of Chemistry
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Abstract
The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The st...arting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.

Source:
New Journal of Chemistry, 2020, 44, 23, 9647-9655
Publisher:
  • Royal Society of Chemistry
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:
  • This is the peer-reviewed version of the article: M. Novakovic, T. Ilic-Tomic, V. Teševi, K. Simic, S. Ivanovic, S. Simic, I. Opsenica and J. Nikodinovic-Runic, New J. Chem., 2020, DOI: https://doi.org/10.1039/D0NJ00758G
  • The published version: https://cer.ihtm.bg.ac.rs/handle/123456789/3639

DOI: 10.1039/d0nj00758g

ISSN: 1144-0546

WoS: 000542706600007

Scopus: 2-s2.0-85086801724
[ Google Scholar ]
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/3717
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
TY  - JOUR
AU  - Novaković, Miroslav
AU  - Ilić-Tomić, Tatjana
AU  - Tešević, Vele
AU  - Simić, Katarina
AU  - Ivanović, Stefan
AU  - Simić, Stefan
AU  - Opsenica, Igor
AU  - Nikodinović-Runić, Jasmina
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3717
AB  - The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.
PB  - Royal Society of Chemistry
T2  - New Journal of Chemistry
T1  - Bisaurones-enzymatic production and biological evaluation
VL  - 44
IS  - 23
SP  - 9647
EP  - 9655
DO  - 10.1039/d0nj00758g
ER  - 
@article{
author = "Novaković, Miroslav and Ilić-Tomić, Tatjana and Tešević, Vele and Simić, Katarina and Ivanović, Stefan and Simić, Stefan and Opsenica, Igor and Nikodinović-Runić, Jasmina",
year = "2020",
abstract = "The Trametes versicolor laccase catalyzed oxidation of chalcone butein afforded four dimers of aurone sulfuretin (i.e. two regioisomeric pairs of diasteromers, 1-4) as the major products. The formation of the dimers was explained by a two step process involving the initial cyclization of butein into aurone sulfuretin, followed by the combination of two molecules of sulfuretin. The coupling process occurred between the 2,10-double bond of one molecule of sulfuretin and the (3′,4′) catechol group of the other to yield a dimeric structure. This was confirmed by the experiment involving the laccase catalyzed oxidation of sulfuretin yielding the same dimeric bisaurones. Compounds 1, 3 and 4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound 2, isolated as a mixture containing ca. 25% of compound 1, was proposed by the comparison of 1H NMR data to compound 1 and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers 1, 3 and 4, were evaluated for their cytotoxic and antioxidative properties in vitro using a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. The C. coggygria bark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.",
publisher = "Royal Society of Chemistry",
journal = "New Journal of Chemistry",
title = "Bisaurones-enzymatic production and biological evaluation",
volume = "44",
number = "23",
pages = "9647-9655",
doi = "10.1039/d0nj00758g"
}
Novaković, M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I.,& Nikodinović-Runić, J.. (2020). Bisaurones-enzymatic production and biological evaluation. in New Journal of Chemistry
Royal Society of Chemistry., 44(23), 9647-9655.
https://doi.org/10.1039/d0nj00758g
Novaković M, Ilić-Tomić T, Tešević V, Simić K, Ivanović S, Simić S, Opsenica I, Nikodinović-Runić J. Bisaurones-enzymatic production and biological evaluation. in New Journal of Chemistry. 2020;44(23):9647-9655.
doi:10.1039/d0nj00758g .
Novaković, Miroslav, Ilić-Tomić, Tatjana, Tešević, Vele, Simić, Katarina, Ivanović, Stefan, Simić, Stefan, Opsenica, Igor, Nikodinović-Runić, Jasmina, "Bisaurones-enzymatic production and biological evaluation" in New Journal of Chemistry, 44, no. 23 (2020):9647-9655,
https://doi.org/10.1039/d0nj00758g . .

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