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Molecules 2017, 22(5), 819; doi:10.3390/molecules22050819

Biomimetic Synthesis of Resveratrol Trimers Catalyzed by Horseradish Peroxidase

1
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China
2
Key Laboratory of Chemistry in Ethnic Medicinal Resources, State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming 650500, China
*
Author to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 31 March 2017 / Revised: 11 May 2017 / Accepted: 11 May 2017 / Published: 17 May 2017
(This article belongs to the Section Natural Products)
View Full-Text   |   Download PDF [1813 KB, uploaded 17 May 2017]   |  

Abstract

Biotransformation of trans-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 (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 (813). 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. View Full-Text
Keywords: horseradish peroxidase; ε-viniferin; resveratrol trimer; biotransformation; radical reaction horseradish peroxidase; ε-viniferin; resveratrol trimer; biotransformation; radical reaction
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Zhang, J.-Q.; Li, G.-P.; Kang, Y.-L.; Teng, B.-H.; Yao, C.-S. Biomimetic Synthesis of Resveratrol Trimers Catalyzed by Horseradish Peroxidase. Molecules 2017, 22, 819.

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