Mechanism of oolongtheanin formation via three intermediates

[Display omitted] •A novel intermediate was found in the formation of oolongtheanins from catechins.•A mechanism of oolongtheanin formation was then proposed.•This mechanism was confirmed by GC–MS and 1H NMR experiments. To clarify the mechanism of oolongtheanin formation, the oxidations of (−)-epig...

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Bibliographic Details
Published inTetrahedron letters Vol. 61; no. 11; p. 151601
Main Authors Hirose, Sayumi, Kamatari, Yuji O., Yanase, Emiko
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 12.03.2020
Subjects
Epigallocatechin
Formation mechanism
Intermediate
Oolong tea
Oolongtheanin
Epigallocatechin
Intermediate
Oolong tea
Formation mechanism
Oolongtheanin
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Summary:[Display omitted] •A novel intermediate was found in the formation of oolongtheanins from catechins.•A mechanism of oolongtheanin formation was then proposed.•This mechanism was confirmed by GC–MS and 1H NMR experiments. To clarify the mechanism of oolongtheanin formation, the oxidations of (−)-epigallocatechin and (−)-epigallocatechin gallate were investigated, and key intermediates were isolated. These intermediates were determined to be dehydrotheasinensins and pro-oolongtheanins, which we have reported previously, and one novel intermediate. Based on the chemical structures of these intermediates, a mechanism was proposed for oolongtheanin formation from catechins, and confirmed by NMR and GC–MS analysis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2020.151601