Journal
CARBOHYDRATE POLYMERS
Volume 194, Issue -, Pages 24-33Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carbpol.2018.04.016
Keywords
beta-Cyclodextrin; Tea non-epicatechins; X-ray analysis; DFT calculation; DPPH assay; Antioxidant activity
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Funding
- Ratchadapisek Sompoch Endowment Fund, Chulalongkorn University [CU-58-021-FW]
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Polyphenolic catechins prevalent in tea are powerful antioxidants for therapeutics of various free radical-related diseases. The non-epicatechins are thermally obtained from the naturally abundant epicatechins. In our study series on the structure-antioxidant property relationship of the CD inclusion complexes with tea catechins, this closing chapter presents the beta-CD encapsulation of three non-epicatechins, i.e., (-)-gallocatechin (GC) 1, (-)-catechin gallate (GC) 2, and (-)-gallocatechin gallate (GCG) 3 investigated by means of single-crystal X-ray diffraction, DFT calculation and DPPH radical scavenging activity assay. Detailed structural comparisons of the beta-CD inclusion complexes with both non-epi and epi type catechins reveal that a common host-guest hydrogen bonding scheme and the shielding of catechin OH groups inside the host circular wall play a prime role in flourishing antioxidant capacities in the order of 3 > 2 > 1. This is consistent with the relative thermodynamic stabilities derived from DFT energy minimization.
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