Flavonolignan 2,3-dehydroderivatives: Preparation, antiradical and cytoprotective activity
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
26582372
DOI
10.1016/j.freeradbiomed.2015.11.014
PII: S0891-5849(15)01112-0
Knihovny.cz E-resources
- Keywords
- Antioxidants, Aryloxy radicals, Electron transfer, Flavonolignans, Hydrogen transfer, Oxidation,
- MeSH
- Antioxidants pharmacology MeSH
- Hep G2 Cells MeSH
- Cytoprotection * MeSH
- Electron Spin Resonance Spectroscopy MeSH
- Flavonolignans chemistry pharmacology MeSH
- Rats MeSH
- Humans MeSH
- Silybin MeSH
- Silymarin pharmacology MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Rats MeSH
- Humans MeSH
- Male MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Antioxidants MeSH
- Flavonolignans MeSH
- Silybin MeSH
- silidianin MeSH Browser
- silychristin MeSH Browser
- Silymarin MeSH
The protective constituents of silymarin, an extract from Silybum marianum fruits, have been extensively studied in terms of their antioxidant and hepatoprotective activities. Here, we explore the electron-donor properties of the major silymarin flavonolignans. Silybin (SB), silychristin (SCH), silydianin (SD) and their respective 2,3-dehydroderivatives (DHSB, DHSCH and DHSD) were oxidized electrochemically and their antiradical/antioxidant properties were investigated. Namely, Folin-Ciocalteau reduction, DPPH and ABTS(+) radical scavenging, inhibition of microsomal lipid peroxidation and cytoprotective effects against tert-butyl hydroperoxide-induced damage to a human hepatocellular carcinoma HepG2 cell line were evaluated. Due to the presence of the highly reactive C3-OH group and the C-2,3 double bond (ring C) allowing electron delocalization across the whole structure in the 2,3-dehydroderivatives, these compounds are much more easily oxidized than the corresponding flavonolignans SB, SCH and SD. This finding was unequivocally confirmed not only by experimental approaches, but also by density functional theory (DFT) calculations. The hierarchy in terms of ability to undergo electrochemical oxidation (DHSCH~DHSD>DHSB>>SCH/SD>SB) was consistent with their antiradical activities, mainly DPPH scavenging, as well as in vitro cytoprotection of HepG2 cells. The results are discussed in the context of the antioxidant vs. prooxidant activities of flavonolignans and molecular interactions in complex biological systems.
References provided by Crossref.org
Selectively Halogenated Flavonolignans-Preparation and Antibacterial Activity
Sulfated Phenolic Substances: Preparation and Optimized HPLC Analysis
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners
Oxidative Stress Evaluation in Ischemia Reperfusion Models: Characteristics, Limits and Perspectives
Dual SMO/BRAF Inhibition by Flavonolignans from Silybum marianum †
Biotransformation of Silymarin Flavonolignans by Human Fecal Microbiota
Preparation of Retinoyl-Flavonolignan Hybrids and Their Antioxidant Properties
Modulation of Skin Inflammatory Response by Active Components of Silymarin
Dermal Delivery of Selected Polyphenols from Silybum marianum. Theoretical and Experimental Study
Sulfated Metabolites of Flavonolignans and 2,3-Dehydroflavonolignans: Preparation and Properties
In-Vitro Activity of Silybin and Related Flavonolignans against Leishmania infantum and L. donovani
Chemoenzymatic Preparation and Biophysical Properties of Sulfated Quercetin Metabolites
