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Issue 46, 2019
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Systematic characterisation of the structure and radical scavenging potency of Pu'Er tea ( ) polyphenol theaflavin

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Abstract

The structure, energetics and radical scavenging potency of theaflavin (TF), a natural polyphenolic antioxidant found in oxidised tea, have been characterised by a series of density functional theory (DFT) determinations. Exploratory conformational searches yielded 153 distinct neutral structures. Results showed TF's structural preferences to be regulated by its unique fused double ring benzotropolone moiety, and its degree of planarity, with structural diversity, principally arising from variations of its nine –OH groups. The distinct 3D conformational ‘poses’ are shown to be stabilised by a complex network of intra-system interactions, damping overall structural floppiness. This rigidification, together with stability, is shown to be coupled with radical scavenging potency in the TF system. Radical scavenging via hydrogen atom abstraction (HAB) in H2O solution was determined to be spontaneous with very low reaction barriers (ΔGrel ∼ 4 kJ mol−1).

Graphical abstract: Systematic characterisation of the structure and radical scavenging potency of Pu'Er tea () polyphenol theaflavin

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Supplementary files

Article information


Submitted
13 Sep 2019
Accepted
10 Nov 2019
First published
15 Nov 2019

Org. Biomol. Chem., 2019,17, 9942-9950
Article type
Paper

Systematic characterisation of the structure and radical scavenging potency of Pu'Er tea (Image ID:c9ob02007a-u1.gif) polyphenol theaflavin

H. T. Vu, F. V. Song, K. V. Tian, H. Su and G. A. Chass, Org. Biomol. Chem., 2019, 17, 9942
DOI: 10.1039/C9OB02007A

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