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Biomimetic Synthesis of Resveratrol Trimers Catalyzed by Horseradish Peroxidase.


ABSTRACT: Biotransformation of trans-resveratrol and synthetic (±)-?-viniferin in aqueous acetone using horseradish peroxidase and hydrogen peroxide as oxidants resulted in the isolation of two new resveratrol trimers (3 and 4), one new resveratrol derivative (5) with a dihydrobenzofuran skeleton, together with two known stilbene trimers (6 and 7), and six known stilbene dimers (8-13). Their structures and relative configurations were identified through spectral analysis and possible formation mechanisms were also discussed. Among these oligomers, trimers 6 and 7 were obtained for the first time through direct transformation from resveratrol. Results indicated that this reaction is suitable for the preparation of resveratrol oligomers with a complex structure.

SUBMITTER: Zhang JQ 

PROVIDER: S-EPMC6154677 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Biomimetic Synthesis of Resveratrol Trimers Catalyzed by Horseradish Peroxidase.

Zhang Jian-Qiao JQ   Li Gan-Peng GP   Kang Yu-Long YL   Teng Bin-Hao BH   Yao Chun-Suo CS  

Molecules (Basel, Switzerland) 20170517 5


Biotransformation of <i>trans</i>-resveratrol and synthetic (±)-ε-viniferin in aqueous acetone using horseradish peroxidase and hydrogen peroxide as oxidants resulted in the isolation of two new resveratrol trimers (<b>3</b> and <b>4</b>), one new resveratrol derivative (<b>5</b>) with a dihydrobenzofuran skeleton, together with two known stilbene trimers (<b>6</b> and <b>7</b>), and six known stilbene dimers (<b>8</b>-<b>13</b>). Their structures and relative configurations were identified thro  ...[more]

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