title: Lignin-derived oak phenolics: a theoretical examination of additional potential health benefits of red wine.
abstract: Lignin-derived phenolic compounds can be extracted from oak barrels during the aging of red wine, and it is hypothesized that these compounds may contribute to the health benefits of red wine by their antioxidant, radical-scavenging, or chemopreventive activities. Density functional calculations (B3LYP/6-311++G) support the radical-scavenging abilities of the oak phenolics. Sinapaldehyde, syringaldehyde, syringol, and syringylacetone all have bond dissociation energies that are lower than resveratrol and comparable to the flavonoid catechin. Molecular docking studies of the oak phenolics with known resveratrol protein targets also show that these compounds dock favorably to the protein targets. Thus, lignin-derived oak phenolics, although found in small concentrations, may contribute to the beneficial antioxidant, chemopreventive, and cardioprotective effects of red wine.
authors.affiliation: Department of Chemistry, University of Alabama in Huntsville, Huntsville, AL 35899, USA. wsetzer@chemistry.uah.edu
authors.forename: William N
authors.initials: WN
authors.lastname: Setzer
mesh_terms: D005511:Food Handling; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D008031:Lignin / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry* / Q000378:metabolism; D011485:Protein Binding / Q000502:physiology; D011506:Proteins / Q000378:metabolism; D029963:Quercus / Q000737:chemistry*; D014920:Wine
chemical_list: D016166:Free Radical Scavengers; D010636:Phenols; D011506:Proteins; D008031:Lignin