Bisaurones - enzymatic production and biological evaluation
Samo za registrovane korisnike
2020
Autori
Novakovi, Miroslav M.Ilić-Tomić, Tatjana
Tešević, Vele
Simić, Katarina
Ivanović, Stefan
Simić, Stefan
Opsenica, Igor
Nikodinović-Runić, Jasmina
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Izvor:
New Journal of Chemistry, 2020, 44, 23, 9647-9655Izdavač:
- Royal Soc Chemistry, Cambridge
Finansiranje / projekti:
- Bioaktivni prirodni proizvodi samoniklih, gajenih i jestivih biljaka: određivanje struktura i aktivnosti (RS-MESTD-Basic Research (BR or ON)-172053)
- Sinteza aminohinolina i njihovih derivata kao antimalarika i inhibitora botulinum neurotoksina A (RS-MESTD-Basic Research (BR or ON)-172008)
- Izučavanje mikrobiološkog diverziteta i karakterizacija korisnih sredinskih mikroorganizama (RS-MESTD-Basic Research (BR or ON)-173048)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200168 (Univerzitet u Beogradu, Hemijski fakultet) (RS-MESTD-inst-2020-200168)
- Ministarstvo nauke, tehnološkog razvoja i inovacija Republike Srbije, institucionalno finansiranje - 200026 (Univerzitet u Beogradu, Institut za hemiju, tehnologiju i metalurgiju - IHTM) (RS-MESTD-inst-2020-200026)
Napomena:
- This is the peer-reviewed version of the article: https://imagine.imgge.bg.ac.rs/handle/123456789/1761
Povezane informacije:
- Druga verzija
https://imagine.imgge.bg.ac.rs/handle/123456789/1761
DOI: 10.1039/d0nj00758g
ISSN: 1144-0546
WoS: 000542706600007
Scopus: 2-s2.0-85086801724
Institucija/grupa
Institut za molekularnu genetiku i genetičko inženjerstvoTY - JOUR AU - Novakovi, Miroslav M. 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/123456789/1310 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 = "Novakovi, Miroslav M. 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 = "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" }
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. in New Journal of Chemistry Royal Soc Chemistry, Cambridge., 44(23), 9647-9655. https://doi.org/10.1039/d0nj00758g
Novakovi MM, 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 .
Novakovi, Miroslav M., 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 . .