Novel flavonolignan hybrid antioxidants: From enzymatic preparation to molecular rationalization
Jazyk angličtina Země Francie Médium print-electronic
Typ dokumentu časopisecké články
PubMed
28068598
DOI
10.1016/j.ejmech.2016.12.051
PII: S0223-5234(16)31057-1
Knihovny.cz E-zdroje
- Klíčová slova
- Cytoprotection, Enzymatic coupling, Lipid peroxidation, Multipotent antioxidant, Silybin, Vitamin C,
- MeSH
- antioxidancia chemie metabolismus farmakologie MeSH
- buněčná membrána metabolismus MeSH
- buňky Hep G2 MeSH
- cytoprotekce účinky léků MeSH
- enzymy imobilizované MeSH
- flavonolignany chemie metabolismus farmakologie MeSH
- fungální proteiny MeSH
- játra cytologie účinky léků metabolismus MeSH
- lidé MeSH
- lipasa metabolismus MeSH
- molekulární konformace MeSH
- peroxidace lipidů účinky léků MeSH
- silibinin MeSH
- silymarin chemie MeSH
- simulace molekulární dynamiky MeSH
- transport elektronů MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- antioxidancia MeSH
- enzymy imobilizované MeSH
- flavonolignany MeSH
- fungální proteiny MeSH
- lipasa MeSH
- Novozyme 435 MeSH Prohlížeč
- silibinin MeSH
- silymarin MeSH
A series of antioxidants was designed and synthesized based on conjugation of the hepatoprotective flavonolignan silybin with l-ascorbic acid, trolox alcohol or tyrosol via a C12 aliphatic linker. These hybrid molecules were prepared from 12-vinyl dodecanedioate-23-O-silybin using the enzymatic regioselective acylation procedure with Novozym 435 (lipase B) or with lipase PS. Voltammetric analyses showed that the silybin-ascorbic acid conjugate exhibited excellent electron donating ability, in comparison to the other conjugates. Free radical scavenging, antioxidant activities and cytoprotective action were evaluated. The silybin-ascorbic acid hybrid exhibited the best activities (IC50 = 30.2 μM) in terms of lipid peroxidation inhibition. The promising protective action of the conjugate against lipid peroxidation can be attributed to modulated electron transfer abilities of both the silybin and ascorbate moieties, but also to the hydrophobic C12 linker facilitating membrane insertion. This was supported experimentally and theoretically by density functional theory (DFT) and molecular dynamics (MD) calculations. The results presented here can be used in the further development of novel multipotent antioxidants and cytoprotective agents, in particular for substances acting at an aqueous/lipid interface.
Citace poskytuje Crossref.org
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