Synthesis of Tyrosol and Hydroxytyrosol Glycofuranosides and Their Biochemical and Biological Activities in Cell-Free and Cellular Assays
Tyrosol (T) and hydroxytyrosol (HOT) and their glycosides are promising candidates for applications in functional food products or in complementary therapy. A series of phenylethanoid glycofuranosides (PEGFs) were synthesized to compare some of their biochemical and biological activities with T and HOT. The optimization of glycosylation promoted by environmentally benign basic zinc carbonate was performed to prepare HOT α-L-arabino-, β-D-apio-, and β-D-ribofuranosides. T and HOT β-D-fructofuranosides, prepared by enzymatic transfructosylation of T and HOT, were also included in the comparative study. The antioxidant capacity and DNA-protective potential of T, HOT, and PEGFs on plasmid DNA were determined using cell-free assays. The DNA-damaging potential of the studied compounds for human hepatoma HepG2 cells and their DNA-protective potential on HepG2 cells against hydrogen peroxide were evaluated using the comet assay. Experiments revealed a spectrum of different activities of the studied compounds. HOT and HOT β-D-fructofuranoside appear to be the best-performing scavengers and protectants of plasmid DNA and HepG2 cells. T and T β-D-fructofuranoside display almost zero or low scavenging/antioxidant activity and protective effects on plasmid DNA or HepG2 cells. The results imply that especially HOT β-D-fructofuranoside and β-D-apiofuranoside could be considered as prospective molecules for the subsequent design of supplements with potential in food and health protection.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:26 |
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| Enthalten in: |
Molecules (Basel, Switzerland) - 26(2021), 24 vom: 15. Dez. |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Kis, Peter [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 09.02.2022 Date Revised 09.02.2022 published: Electronic Citation Status MEDLINE |
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| doi: |
10.3390/molecules26247607 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM334826098 |
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| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Tyrosol (T) and hydroxytyrosol (HOT) and their glycosides are promising candidates for applications in functional food products or in complementary therapy. A series of phenylethanoid glycofuranosides (PEGFs) were synthesized to compare some of their biochemical and biological activities with T and HOT. The optimization of glycosylation promoted by environmentally benign basic zinc carbonate was performed to prepare HOT α-L-arabino-, β-D-apio-, and β-D-ribofuranosides. T and HOT β-D-fructofuranosides, prepared by enzymatic transfructosylation of T and HOT, were also included in the comparative study. The antioxidant capacity and DNA-protective potential of T, HOT, and PEGFs on plasmid DNA were determined using cell-free assays. The DNA-damaging potential of the studied compounds for human hepatoma HepG2 cells and their DNA-protective potential on HepG2 cells against hydrogen peroxide were evaluated using the comet assay. Experiments revealed a spectrum of different activities of the studied compounds. HOT and HOT β-D-fructofuranoside appear to be the best-performing scavengers and protectants of plasmid DNA and HepG2 cells. T and T β-D-fructofuranoside display almost zero or low scavenging/antioxidant activity and protective effects on plasmid DNA or HepG2 cells. The results imply that especially HOT β-D-fructofuranoside and β-D-apiofuranoside could be considered as prospective molecules for the subsequent design of supplements with potential in food and health protection | ||
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| 650 | 4 | |a cytotoxicity | |
| 650 | 4 | |a hydroxytyrosol | |
| 650 | 4 | |a phenylethanoid glycofuranosides | |
| 650 | 4 | |a tyrosol | |
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| 700 | 1 | |a Horváthová, Eva |e verfasserin |4 aut | |
| 700 | 1 | |a Gálová, Eliška |e verfasserin |4 aut | |
| 700 | 1 | |a Ševčovičová, Andrea |e verfasserin |4 aut | |
| 700 | 1 | |a Antalová, Veronika |e verfasserin |4 aut | |
| 700 | 1 | |a Karnišová Potocká, Elena |e verfasserin |4 aut | |
| 700 | 1 | |a Mastihuba, Vladimír |e verfasserin |4 aut | |
| 700 | 1 | |a Mastihubová, Mária |e verfasserin |4 aut | |
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