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

Carbohydrate Polymers
Thammarat Aree, Suchada Jongrungruangchok

Abstract

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 ...Continue Reading

References

Mar 27, 2007·Carbohydrate Research·Alfred D French, Glenn P Johnson
Sep 4, 2007·Journal of Agricultural and Food Chemistry·Ioannis MourtzinosVaios T Karathanos
Jun 28, 2008·Journal of Agricultural and Food Chemistry·Fátima Paiva-Martins, Marisa Pinto
Sep 12, 2008·Journal of Agricultural and Food Chemistry·David G Cornwell, Jiyan Ma
May 21, 2010·Acta Crystallographica. Section B, Structural Science·Frank H Allen, Ian J Bruno
Sep 1, 2001·Environmental Toxicology and Pharmacology·C G HeijnenA Bast
Dec 14, 2011·The Journal of Physical Chemistry. B·Udo Schnupf, Frank A Momany
Apr 11, 2012·International Journal of Molecular Sciences·Rahele GhanbariNazamid Saari
Nov 6, 2013·Critical Reviews in Food Science and Nutrition·José Manuel López-NicolásFrancisco García-Carmona
Dec 5, 2013·Carbohydrate Polymers·Eva PinhoMariana Henriques
Dec 7, 2013·Journal of Agricultural and Food Chemistry·Marcos García-PadialArantza Zornoza
Feb 1, 2014·Journal of Agricultural and Food Chemistry·Ting HuXi-Lin Xu
Jul 6, 2016·Journal of Agricultural and Food Chemistry·Vito Michele ParadisoFrancesco Caponio

❮ Previous
Next ❯

Citations

Jul 17, 2020·Journal of Biomolecular Structure & Dynamics·Naresh KumarNidhi Goel
Apr 4, 2021·Pharmaceutics·Magdalena Paczkowska-WalendowskaJudyta Cielecka-Piontek
Oct 15, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Bingyan YangYu Zhang
Jan 4, 2022·Journal of Biomolecular Structure & Dynamics·Riyadh Ahmed Atto Al-ShuaeebM M Khalil

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.