Bisaurones-enzymatic production and biological evaluation
Authors
Novaković, Miroslav
Ilić-Tomić, Tatjana

Tešević, Vele

Simić, Katarina

Ivanović, Stefan

Simić, Stefan

Opsenica, Igor

Nikodinović-Runić, Jasmina

Article (Accepted Version)
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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, 9647-9655Publisher:
- 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
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IHTMTY - 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 . .