δ-Viniferin, a Resveratrol Dehydrodimer: One of the Major Stilbenes Synthesized by Stressed Grapevine Leaves

• Published in: Journal of agricultural and food chemistry Vol. 51; no. 18; pp. 5488 - 5492
• Main Authors: Pezet, Roger, Perret, Camille, Jean-Denis, Julien Bernard, Tabacchi, Raffaele, Gindro, Katia, Viret, Olivier
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 27.08.2003
• Subjects: Benzofurans - analysis; biosynthesis; chemical structure; Chromatography, High Pressure Liquid; Dimerization; downy mildew; grapes; leaves; Magnetic Resonance Spectroscopy; Oomycetes; Oxidation-Reduction; phytoalexins; Plant Diseases; Plant Leaves - chemistry; Plant Leaves - metabolism; plant pathogenic fungi; plant stress; Plasmopara viticola; Resorcinols - analysis; resveratrol; Stilbenes; ultraviolet radiation; Ultraviolet Rays; Vitis - chemistry; Vitis - metabolism; Vitis vinifera
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf030227o

δ-Viniferin is a resveratrol dehydrodimer, an isomer of ε-viniferin. This compound has been reported as a molecule produced in vitro by the oxidative dimerization of resveratrol by plant peroxidases or fungal laccases. It was also recently identified in wines and in grape cell cultures. We have now identified this dimer by NMR, high-performance liquid chromatography−diode array detection (HPLC-DAD), and HPLC-mass spectrometry (MS) in grapevine leaves infected by Plasmopara viticola (downy mildew) or UV-C irradiated. Its concentration was higher than that of ε-viniferin and constitutes one of the most important phytoalexins derived from resveratrol. Keywords: Stilbenes; Vitis vinifera; resveratrol; viniferins; HPLC; LC-MS; NMR; UV spectra