Structures of Two Novel Trimeric Stilbenes Obtained by Horseradish Peroxidase Catalyzed Biotransformation of trans-Resveratrol and (−)-ε-Viniferin

• Published in: Journal of agricultural and food chemistry Vol. 58; no. 11; pp. 6754 - 6761
• Main Authors: Wilkens, Andrea, Paulsen, Jana, Wray, Victor, Winterhalter, Peter
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 09.06.2010; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Benzofurans - chemistry; Bioconversions. Hemisynthesis; Biological and medical sciences; Biotechnology; Catalysis; Chemical Aspects of Biotechnology/Molecular Biology; Chemistry; Chemistry, Applied; Food industries; Food Science & Technology; Fundamental and applied biological sciences. Psychology; Horseradish Peroxidase - chemistry; Life Sciences & Biomedicine; Methods. Procedures. Technologies; Molecular Structure; Physical Sciences; Resorcinols - chemistry; Science & Technology; Stilbenes - chemistry; stilbenes; high-speed countercurrent chromatography; Biotransformation; horseradish peroxidase; PLANT; PREPARATIVE ISOLATION; POLYGONUM-CUSPIDATUM; VITIS-VINIFERA KYOHOU; OLIGOMERS; ZUCC; COUNTER-CURRENT CHROMATOGRAPHY; PURIFICATION; PARTHENOCISSUS-LAETEVIRENS; SEPARATION; Countercurrent chromatography; Enzyme; Peroxidases; High speed; Resveratrol; Peroxidase; Oxidoreductases; Structure; Stilbene
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf100606p

Two stilbenes, trans-resveratrol and (−)-ε-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-δ-viniferin, a resveratrol−trans-dehydrodimer. Large-scale biotransformation of a mixture of trans-resveratrol and (−)-ε-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.