Structure–antioxidant activity relationship of β-cyclodextrin inclusion complexes with olive tyrosol, hydroxytyrosol and oleuropein: Deep insights from X-ray analysis, DFT calculation and DPPH assay
| Autor: | Thammarat Aree, Suchada Jongrungruangchok |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Antioxidant
Polymers and Plastics DPPH medicine.medical_treatment Iridoid Glucosides 02 engineering and technology Crystallography X-Ray 01 natural sciences Structure-Activity Relationship chemistry.chemical_compound Oleuropein Materials Chemistry medicine Organic chemistry Iridoids chemistry.chemical_classification Molecular Structure Cyclodextrin 010405 organic chemistry Hydrogen bond beta-Cyclodextrins Organic Chemistry Hydrogen Bonding Free Radical Scavengers Phenylethyl Alcohol 021001 nanoscience & nanotechnology 0104 chemical sciences Tyrosol Models Chemical chemistry Polyphenol Quantum Theory Thermodynamics Hydroxytyrosol 0210 nano-technology |
| Zdroj: | Carbohydrate Polymers. 199:661-669 |
| ISSN: | 0144-8617 |
| Popis: | Olives and olive oil, a key food type of the Mediterranean diets, are packed with various important polyphenols including oleuropein (OLE), hydroxytyrosol (HTY) and tyrosol (TYR). OLE and HTY are highly powerful antioxidants and play a prime role in the therapeutics of free radical-related diseases. Their molecular stabilities and antioxidant properties can be improved by cyclodextrin (CD) encapsulation. Here, we present a systematic investigation on the inclusion complexes of β-CD–TYR (1), β-CD–HTY (2) and β-CD–OLE (3) by combined single-crystal structure determination, DFT complete-geometry optimization and DPPH antioxidant assay. X-ray analysis and DFT calculation reveal the preference of inclusion geometry with deep protrusion of the aromatic ring moieties of TYR, HTY and OLE from the β-CD O6–H-side, and the common host-guest stabilization scheme via intermolecular O–H⋯O hydrogen bonding interactions. No polyphenol OH group is shielded in the β-CD cavity, in contrast to the structures of β-CD–tea catechins complexes. The established host-guest O–H⋯O hydrogen bonds help to elevate antioxidant capacities of the olive polyphenols upon β-CD encapsulation. The order of antioxidant activity 2 > 3 ≫ 1 based on the DPPH measurement is in fair agreement with their relative thermodynamic stabilities derived from DFT calculation. |
| Databáze: | OpenAIRE |
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