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 in:Tetrahedron letters 2020-03, Vol.61 (11), p.151601, Article 151601
Main Authors: Hirose, Sayumi, Kamatari, Yuji O., Yanase, Emiko
Format: Article
Language:English
Subjects:
Epigallocatechin
Formation mechanism
Intermediate
Oolong tea
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