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The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2.
Molecules. 2017 Jul 21; 22(7)M

Abstract

The synthesis of different classes of prenylated aglycones (α,β-dihydroxanthohumol (2) and (Z)-6,4'-dihydroxy-4-methoxy-7-prenylaurone (3)) was performed in one step reactions from xanthohumol (1)-major prenylated chalcone naturally occurring in hops. Obtained flavonoids (2-3) and xanthohumol (1) were used as substrates for regioselective fungal glycosylation catalyzed by two Absidia species and Beauveria bassiana. As a result six glycosides (4-9) were formed, of which four glycosides (6-9) have not been published so far. The influence of flavonoid skeleton and the presence of glucopyranose and 4-O-methylglucopyranose moiety in flavonoid molecule on binding to main protein in plasma, human serum albumin (HSA), and inhibition of cyclooxygenases COX-1 and COX-2 were investigated. Results showed that chalcone (1) had the highest binding affinity to HSA (8.624 × 10⁴ M-1) of all tested compounds. It has also exhibited the highest inhibition of cyclooxygenases activity, and it was a two-fold stronger inhibitor than α,β-dihydrochalcone (2) and aurone (3). The presence of sugar moiety in flavonoid molecule caused the loss of HSA binding activity as well as the decrease in inhibition of cyclooxygenases activity.

Authors+Show Affiliations

Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. tomasz.tronina@upwr.edu.pl.Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. paulina.strugala@upwr.edu.pl.Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. jaroslaw.poplonski@upwr.edu.pl.Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. aleksandra.wloch@upwr.edu.pl.Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. sandra.sordon@upwr.edu.pl.Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. agnieszka.bartmanska@upwr.edu.pl.Department of Chemistry, Wrocław University of Environmental and Life Sciences, Norwida 25, 50-375 Wrocław, Poland. ewa.huszcza@upwr.edu.pl.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28754033

Citation

Tronina, Tomasz, et al. "The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids On Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2." Molecules (Basel, Switzerland), vol. 22, no. 7, 2017.
Tronina T, Strugała P, Popłoński J, et al. The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2. Molecules. 2017;22(7).
Tronina, T., Strugała, P., Popłoński, J., Włoch, A., Sordon, S., Bartmańska, A., & Huszcza, E. (2017). The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2. Molecules (Basel, Switzerland), 22(7). https://doi.org/10.3390/molecules22071230
Tronina T, et al. The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids On Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2. Molecules. 2017 Jul 21;22(7) PubMed PMID: 28754033.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - The Influence of Glycosylation of Natural and Synthetic Prenylated Flavonoids on Binding to Human Serum Albumin and Inhibition of Cyclooxygenases COX-1 and COX-2. AU - Tronina,Tomasz, AU - Strugała,Paulina, AU - Popłoński,Jarosław, AU - Włoch,Aleksandra, AU - Sordon,Sandra, AU - Bartmańska,Agnieszka, AU - Huszcza,Ewa, Y1 - 2017/07/21/ PY - 2017/07/05/received PY - 2017/07/18/revised PY - 2017/07/19/accepted PY - 2017/7/30/entrez PY - 2017/7/30/pubmed PY - 2018/4/21/medline KW - COX-1 KW - COX-2 KW - cyclooxygenases KW - glycosides KW - human serum albumin KW - microbial glycosylation KW - prenylated flavonoids KW - xanthohumol JF - Molecules (Basel, Switzerland) JO - Molecules VL - 22 IS - 7 N2 - The synthesis of different classes of prenylated aglycones (α,β-dihydroxanthohumol (2) and (Z)-6,4'-dihydroxy-4-methoxy-7-prenylaurone (3)) was performed in one step reactions from xanthohumol (1)-major prenylated chalcone naturally occurring in hops. Obtained flavonoids (2-3) and xanthohumol (1) were used as substrates for regioselective fungal glycosylation catalyzed by two Absidia species and Beauveria bassiana. As a result six glycosides (4-9) were formed, of which four glycosides (6-9) have not been published so far. The influence of flavonoid skeleton and the presence of glucopyranose and 4-O-methylglucopyranose moiety in flavonoid molecule on binding to main protein in plasma, human serum albumin (HSA), and inhibition of cyclooxygenases COX-1 and COX-2 were investigated. Results showed that chalcone (1) had the highest binding affinity to HSA (8.624 × 10⁴ M-1) of all tested compounds. It has also exhibited the highest inhibition of cyclooxygenases activity, and it was a two-fold stronger inhibitor than α,β-dihydrochalcone (2) and aurone (3). The presence of sugar moiety in flavonoid molecule caused the loss of HSA binding activity as well as the decrease in inhibition of cyclooxygenases activity. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/28754033/The_Influence_of_Glycosylation_of_Natural_and_Synthetic_Prenylated_Flavonoids_on_Binding_to_Human_Serum_Albumin_and_Inhibition_of_Cyclooxygenases_COX_1_and_COX_2_ L2 - http://www.mdpi.com/resolver?pii=molecules22071230 DB - PRIME DP - Unbound Medicine ER -