Bisaurones - enzymatic production and biological evaluation
Само за регистроване кориснике
2020
Аутори
Novakovi, Miroslav M.Ilić-Tomić, Tatjana
Tešević, Vele
Simić, Katarina
Ivanović, Stefan
Simić, Stefan
Opsenica, Igor
Nikodinović-Runić, Jasmina
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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.
Извор:
New Journal of Chemistry, 2020, 44, 23, 9647-9655Издавач:
- Royal Soc Chemistry, Cambridge
Финансирање / пројекти:
- Биоактивни природни производи самониклих, гајених и јестивих биљака: одређивање структура и активности (RS-MESTD-Basic Research (BR or ON)-172053)
- Синтеза аминохинолина и њихових деривата као антималарика и инхибитора ботулинум неуротоксина А (RS-MESTD-Basic Research (BR or ON)-172008)
- Изучавање микробиолошког диверзитета и карактеризација корисних срединских микроорганизама (RS-MESTD-Basic Research (BR or ON)-173048)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200168 (Универзитет у Београду, Хемијски факултет) (RS-MESTD-inst-2020-200168)
- Министарство науке, технолошког развоја и иновација Републике Србије, институционално финансирање - 200026 (Универзитет у Београду, Институт за хемију, технологију и металургију - ИХТМ) (RS-MESTD-inst-2020-200026)
Напомена:
- This is the peer-reviewed version of the article: https://imagine.imgge.bg.ac.rs/handle/123456789/1761
Повезане информације:
- Друга верзија
https://imagine.imgge.bg.ac.rs/handle/123456789/1761
DOI: 10.1039/d0nj00758g
ISSN: 1144-0546
WoS: 000542706600007
Scopus: 2-s2.0-85086801724
Институција/група
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 . .