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 (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.
Highlights
Stilbenes are a class of plant polyphenols that can be divided into two categories, namely, monomeric and oligomeric stilbenes
(2) under under the the procedure procedure shown in Figure 2 was used study, semisynthetic semisynthetic ((±)-ε-viniferin as the starting material for biotransformation
Biotransformation of 1 and 2 in aqueous acetone catalyzed by horseradish peroxidase and hydrogen peroxide generated a major product peak 8 and a complicated mixture (Figure S30 in and hydrogen peroxide generated a major product peak 8 and a complicated mixture (Figure S30 in Supplementary Materials), which resulted in the isolation and identification of four resveratrol trimers
Summary
Stilbenes are a class of plant polyphenols that can be divided into two categories, namely, monomeric and oligomeric stilbenes. Resveratrol oligomers possess novel structures and exhibit various biological activities, such as anticarcinogenesis, anti-inflammation, and tyrosinase activity inhibition. These oligomers can be used to treat cancer, AIDS, bacterial infections, and other diseases. In combination with diverse separation methods, transformation can induce the accumulation of large amounts of minor compounds Using this approach, a number of known natural stilbene oligomers and new stilbene oligomers have been obtained, and their structures have been identified successfully [11]. Trimers and 7 were obtained for the firstfrom time through direct transformation were obtained for the first time through direct transformation resveratrol Their were potential potential formation mechanisms formation discussed.
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