Structures of two novel trimeric stilbenes obtained by horseradish peroxidase catalyzed biotransformation of trans-resveratrol and (-)-epsilon-viniferin.
Two stilbenes, trans-resveratrol and (-)-epsilon-viniferin, as well as a mixture of both, were biotransformed using horseradish peroxidase and hydrogen peroxide. Under the applied conditions trans-resveratrol afforded one major product, which was identified as trans-delta-viniferin, a resveratrol-trans-dehydrodimer. Large-scale biotransformation of a mixture of trans-resveratrol and (-)-epsilon-viniferin yielded two novel resveratrol trimers, resviniferin A and resviniferin B, which were obtained in a pure form after fractionation by high-speed countercurrent chromatography and final purification by preparative HPLC. Their structures were established by means of mass spectrometry and 2D NMR spectroscopic analyses, including HSQC, HMBC, COSY, and ROESY.
Wilkens
Andrea
A
Institute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany.
Paulsen
Jana
J
Wray
Victor
V
Winterhalter
Peter
P
D001572:Benzofurans / Q000737:chemistry*; D002384:Catalysis; D006735:Horseradish Peroxidase / Q000737:chemistry*; D015394:Molecular Structure; D012118:Resorcinols / Q000737:chemistry*; D000077185:Resveratrol; D013267:Stilbenes / Q000737:chemistry*
D001572:Benzofurans; D012118:Resorcinols; D013267:Stilbenes; C477734:delta-viniferin; D006735:Horseradish Peroxidase; D000077185:Resveratrol