Crystallographic evidence for β-cyclodextrin inclusion complexation facilitating the improvement of antioxidant activity of tea (+)-catechin and (-)-epicatechin

Carbohydrate Polymers
Thammarat Aree, Suchada Jongrungruangchok

Abstract

Single-crystal X-ray analysis to 0.6Å resolution using synchrotron radiation of the inclusion complexes of β-cyclodextrin (β-CD) with (+)-catechin (CA) and (-)-epicatechin (EC) has been carried out to gain atomistic insight into how the inclusion complexation helps to improve tea catechin antioxidant activity. The β-CD-CA complex crystallizes in the monoclinic P21 space group, whereas the β-CD-EC complex crystallizes in both the monoclinic P21 and triclinic P1 space groups. In comparing the inclusion structures, the β-CD-EC dimeric structure having higher numbers of OH⋯O hydrogen bonds combined with π⋯π interactions is associated with its greater interaction energy, as derived from DFT/B3LYP single-point energy calculations. Detailed structural analysis of the CA, EC conformation and inclusion geometry reveals that the interplay of the intermolecular OH⋯O hydrogen bond stabilized catechol moiety and the protection of OH groups in the β-CD cavity plays a key role in the improvement of antioxidant capacity upon inclusion complexation.

References

Oct 1, 1973·Scientific American·D E Koshland
Oct 1, 1995·Archives of Biochemistry and Biophysics·N SalahC Rice-Evans
Jan 1, 1996·Free Radical Biology & Medicine·C A Rice-EvansG Paganga
Jan 1, 1997·Free Radical Biology & Medicine·G CaoR L Prior
Mar 7, 2000·International Journal of Obesity and Related Metabolic Disorders : Journal of the International Association for the Study of Obesity·A G DullooJ Vandermander
Apr 17, 2001·Biochemical and Biophysical Research Communications·A Sekher PannalaC A Rice-Evans
Feb 1, 2003·Carbohydrate Research·Thammarat Aree, Narongsak Chaichit
Aug 3, 2006·Journal of Agricultural and Food Chemistry·Stella A OrdoudiEvangelos G Bakalbassis
Feb 27, 2007·Journal of Molecular Graphics & Modelling·Chunli YanCe Hao
Mar 14, 2007·Bioorganic & Medicinal Chemistry·Carolina JullianClaudio Olea-Azar
Mar 27, 2007·Carbohydrate Research·Alfred D French, Glenn P Johnson
Apr 13, 2010·Acta Crystallographica. Section D, Biological Crystallography·P EmsleyK Cowtan
May 21, 2010·Acta Crystallographica. Section B, Structural Science·Frank H Allen, Ian J Bruno
Jul 6, 2010·The Journal of Physical Chemistry. a·Jayshree K KhedkarShridhar P Gejji
Aug 2, 2011·Chemical & Pharmaceutical Bulletin·Hiroyuki TsutsumiTakashi Ishizu
Jan 1, 1997·Methods in Enzymology·Zbyszek Otwinowski, Wladek Minor

❮ Previous
Next ❯

Citations

Oct 20, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ying LiuWen Huang

❮ 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.