1. Oligomerization mechanism of epigallocatechin-3-O-gallate during autoxidation.
- Author
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Matsuo, Yosuke, Katayama, Kohei, Yamashita, Takako, Saito, Yoshinori, and Tanaka, Takashi
- Subjects
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OXIDATION , *EPIGALLOCATECHIN gallate , *OLIGOMERIZATION , *CYCLODEXTRINS , *PHLOROGLUCINOL , *QUINONE - Abstract
The autoxidation of tea catechins by dissolved oxygen proceeds in pH-neutral aqueous solutions, and the major products are oligomers. However, the reaction mechanisms have not been clarified. In this study, the autoxidation of (−)-epigallocatechin-3- O -gallate (1) was examined. The autoxidation with β-cyclodextrin, which includes the A-ring of 1 , significantly suppressed oligomer production and increased the formation of products generated by the oxidative cleavage of the B-ring, indicating the participation of the A-ring in the oligomerization. Further, the autoxidation of 1 in the presence of phloroglucinol, a mimic of the catechin A-ring, yielded products via the nucleophilic addition of phloroglucinol to the B-ring quinone of 1. These results indicated that the oxidative A–B ring couplings accounted for the major oligomerization mechanism. • Autoxidation of epigallocatechin gallate (1) yields oligomers as major products. • The oligomerization was suppressed by presence of β-cyclodextrin. • Autoxidation of 1 with phloroglucinol, a mimic of catechin A-ring, yielded coupling products. • The products were produced by addition of phloroglucinol to B-ring quinone of 1. • The key mechanism of oligomerization is coupling between B-ring quinones and A-rings. [ABSTRACT FROM AUTHOR]
- Published
- 2024
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