Bisaurones - enzymatic production and biological evaluation
Authors
Ilić-Tomić, TatjanaTešević, Vele
Simić, Katarina
Ivanović, Stefan
Simić, Stefan
Opsenica, Igor
Nikodinović-Runić, Jasmina
Article (Accepted Version)
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TheTrametes versicolorlaccase 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. Compounds1,3and4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound2, isolated as a mixture containingca.25% of compound1,was proposed by the comparison of(1)H NMR data to compound1and by using LC-ESIMS analysis. The starting chalc...one butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers1,3and4,were evaluated for their cytotoxic and antioxidative propertiesin vitrousing a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. TheC. coggygriabark 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 Soc Chemistry, Cambridge
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-MESTD-Basic Research (BR or ON)-172053)
- The synthesis of aminoquinoline-based antimalarials and botulinum neurotoxin A inhibitors (RS-MESTD-Basic Research (BR or ON)-172008)
- Microbial diversity study and characterization of beneficial environmental microorganisms (RS-MESTD-Basic Research (BR or ON)-173048)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200168 (University of Belgrade, Faculty of Chemistry) (RS-MESTD-inst-2020-200168)
- Ministry of Science, Technological Development and Innovation of the Republic of Serbia, institutional funding - 200026 (University of Belgrade, Institute of Chemistry, Technology and Metallurgy - IChTM) (RS-MESTD-inst-2020-200026)
Note:
- Related to published version: https://imagine.imgge.bg.ac.rs/handle/123456789/1310
- This is the peer reviewed version of the paper: Novakovi, M. M., Ilić-Tomić, T., Tešević, V., Simić, K., Ivanović, S., Simić, S., Opsenica, I., & Nikodinović-Runić, J. (2020). Bisaurones—Enzymatic production and biological evaluation. New Journal of Chemistry, 44(23), 9647–9655. https://doi.org/10.1039/d0nj00758g
Related info:
DOI: 10.1039/d0nj00758g
ISSN: 1144-0546
WoS: 000542706600007
Scopus: 2-s2.0-85086801724
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Institution/Community
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR 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://imagine.imgge.bg.ac.rs/handle/123456789/1761 AB - TheTrametes versicolorlaccase 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. Compounds1,3and4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound2, isolated as a mixture containingca.25% of compound1,was proposed by the comparison of(1)H NMR data to compound1and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers1,3and4,were evaluated for their cytotoxic and antioxidative propertiesin vitrousing a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. TheC. coggygriabark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities. PB - Royal Soc Chemistry, Cambridge T2 - New Journal of Chemistry T1 - Bisaurones - enzymatic production and biological evaluation EP - 9655 IS - 23 SP - 9647 VL - 44 DO - 10.1039/d0nj00758g ER -
@article{ author = "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 = "TheTrametes versicolorlaccase 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. Compounds1,3and4, were isolated using semipreparative HPLC and characterized by the detailed analysis of the NMR, MS, IR, and UV-vis data. The structure of compound2, isolated as a mixture containingca.25% of compound1,was proposed by the comparison of(1)H NMR data to compound1and by using LC-ESIMS analysis. The starting chalcone butein and the products of the biocatalytic transformation, aurone sulfuretin and sulfuretin dimers1,3and4,were evaluated for their cytotoxic and antioxidative propertiesin vitrousing a healthy human fibroblast (MRC5) cell line. The biotransformation products showed lower cytotoxicity but higher antioxidative properties. TheC. coggygriabark methanol extract rich in butein and sulfuretin was also biotransformed by laccase. The transformed extract exhibited significantly improved antioxidative activities.", publisher = "Royal Soc Chemistry, Cambridge", journal = "New Journal of Chemistry", title = "Bisaurones - enzymatic production and biological evaluation", pages = "9655-9647", number = "23", volume = "44", doi = "10.1039/d0nj00758g" }
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 Soc Chemistry, Cambridge., 44(23), 9647-9655. https://doi.org/10.1039/d0nj00758g
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 .
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 . .