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J Agric Food Chem. 2017 Dec 6;65(48):10473-10481. doi: 10.1021/acs.jafc.7b04208. Epub 2017 Nov 27.

Functional Characterization of Epitheaflagallin 3-O-Gallate Generated in Laccase-Treated Green Tea Extracts in the Presence of Gallic Acid.

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Toyama Prefectural Institute for Pharmaceutical Research , 17-1 Nakataikouyama, Imizu, Toyama 939-0363, Japan.
Research Center, Taiyo Kagaku Co. Ltd. , 1-3 Takaramachi, Yokkaichi, Mie 512-1111, Japan.
Kracie Pharma, Ltd. , 3-1 Kanebo-Machi, Takaoka, Toyama 933-0856, Japan.


Epitheaflagallin (ETFG) and epitheaflagallin 3-O-gallate (ETFGg) are minor polyphenols in black tea extract that are enzymatically synthesized from epigallocatechin (EGC) and epigallocatechin gallate (EGCg), respectively, in green tea extract via laccase oxidation in the presence of gallic acid. The constituents of laccase-treated green tea extract in the presence of gallic acid are thus quite different from those of nonlaccase-treated green tea extract: EGC and EGCg are present in lower concentrations, and ETFG and ETFGg are present in higher concentrations. Additionally, laccase-treated green tea extract contains further polymerized catechin derivatives, comparable with naturally fermented teas such as oolong tea and black tea. We found that ETFGg and laccase-treated green tea extracts exhibit versatile physiological functions in vivo and in vitro, including antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinus glycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3 and their synthesis by human gingival fibroblasts. We confirmed that these inhibitory effects of ETFGg in vitro match well with the results obtained by docking simulations of the compounds with their target enzymes or noncatalytic protein. Thus, ETFGg and laccase-treated green tea extracts containing ETFGg are promising functional food materials with potential antiobesity and antiperiodontal disease activities.


antiobesity; antiperiodontal disease; docking simulation; epitheaflagallin (ETFG); epitheaflagallin 3-O-gallate (ETFGg); glycosyltransferase inhibition; laccase-treated green tea extract; matrix metalloprotease inhibition; pancreatic lipase inhibition; theaflavin 3-O-gallate (TFA 3-O-gallate)

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