title: A grapevine cytochrome P450 generates the precursor of wine lactone, a key odorant in wine.
abstract: Monoterpenes are important constituents of the aromas of food and beverages, including wine. Among monoterpenes in wines, wine lactone has the most potent odor. It was proposed to form via acid-catalyzed cyclization of (E)-8-carboxylinalool during wine maturation. It only reaches very low concentrations in wine but its extremely low odor detection threshold makes it an important aroma compound. Using LC-MS/MS, we show here that the (E)-8-carboxylinalool content in wines correlates with their wine lactone content and estimate the kinetic constant for the very slow formation of wine lactone from (E)-8-carboxylinalool. We show that (E)-8-carboxylinalool is accumulated as a glycoside in grape (Vitis vinifera) berries and that one of the cytochrome P450 enzymes most highly expressed in maturing berries, CYP76F14, efficiently oxidizes linalool to (E)-8-carboxylinalool. Our analysis of (E)-8-carboxylinalool in Riesling × Gewurztraminer grapevine progeny established that the CYP76F14 gene co-locates with a quantitative trait locus for (E)-8-carboxylinalool content in grape berries. Our data support the role of CYP76F14 as the major (E)-8-carboxylinalool synthase in grape berries and the role of (E)-8-carboxylinalool as a precursor to wine lactone in wine, providing new insights into wine and grape aroma metabolism, and new methods for food and aroma research and production.
authors: Institute of Plant Molecular Biology, Centre National de la Recherche Scientifique, University of Strasbourg, 12 Rue du Général Zimmer, Strasbourg Cedex, 67084, France.
authors: Tina
authors: T
authors: Ilc
authors: Unité Mixte de Recherche 1131, Institut National de la Recherche Agronomique, University of Strasbourg, 28 Rue de Herrlisheim - BP 20507, Colmar Cedex, 68021, France.
authors: David
authors: D
authors: Halter
authors: Laboratoire de Chimie Organique Synthétique, Centre National de la Recherche Scientifique, University of Strasbourg, 1 Rue Blaise Pascal, Strasbourg Cedex, 67008, France.
authors: Laurence
authors: L
authors: Miesch
authors: Laboratoire de Chimie Organique Synthétique, Centre National de la Recherche Scientifique, University of Strasbourg, 1 Rue Blaise Pascal, Strasbourg Cedex, 67008, France.
authors: Florian
authors: F
authors: Lauvoisard
authors: Institute of Plant Molecular Biology, Centre National de la Recherche Scientifique, University of Strasbourg, 12 Rue du Général Zimmer, Strasbourg Cedex, 67084, France.
authors: Lucie
authors: L
authors: Kriegshauser
authors: Unité Mixte de Recherche 1131, Institut National de la Recherche Agronomique, University of Strasbourg, 28 Rue de Herrlisheim - BP 20507, Colmar Cedex, 68021, France.
authors: Andrea
authors: A
authors: Ilg
authors: Unité Mixte de Recherche 1131, Institut National de la Recherche Agronomique, University of Strasbourg, 28 Rue de Herrlisheim - BP 20507, Colmar Cedex, 68021, France.
authors: Raymonde
authors: R
authors: Baltenweck
authors: Unité Mixte de Recherche 1131, Institut National de la Recherche Agronomique, University of Strasbourg, 28 Rue de Herrlisheim - BP 20507, Colmar Cedex, 68021, France.
authors: Philippe
authors: P
authors: Hugueney
authors: Institute of Plant Molecular Biology, Centre National de la Recherche Scientifique, University of Strasbourg, 12 Rue du Général Zimmer, Strasbourg Cedex, 67084, France.
authors: Danièle
authors: D
authors: Werck-Reichhart
authors: Unité Mixte de Recherche 1131, Institut National de la Recherche Agronomique, University of Strasbourg, 28 Rue de Herrlisheim - BP 20507, Colmar Cedex, 68021, France.
authors: Eric
authors: E
authors: Duchêne
authors: Institute of Plant Molecular Biology, Centre National de la Recherche Scientifique, University of Strasbourg, 12 Rue du Général Zimmer, Strasbourg Cedex, 67084, France.
authors: Nicolas
authors: 0000-0002-2141-1808
authors: N
authors: Navrot
mesh_terms: D000080462:Acyclic Monoterpenes; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D005638:Fruit / Q000201:enzymology / Q000235:genetics; D018506:Gene Expression Regulation, Plant; D017343:Genes, Plant; D007783:Lactones / Q000737:chemistry / Q000378:metabolism*; D039821:Monoterpenes / Q000737:chemistry / Q000378:metabolism; D009812:Odorants / Q000032:analysis*; D018515:Plant Leaves / Q000378:metabolism; D010940:Plant Proteins / Q000378:metabolism; D040641:Quantitative Trait Loci / Q000235:genetics; D014026:Nicotiana / Q000378:metabolism; D027843:Vitis / Q000201:enzymology* / Q000235:genetics; D014920:Wine / Q000032:analysis*
chemical_list: D000080462:Acyclic Monoterpenes; D007783:Lactones; D039821:Monoterpenes; D010940:Plant Proteins; D003577:Cytochrome P-450 Enzyme System; C018584:linalool
keywords: cytochrome P450; grapevine; quantitative trait locus (QTL); wine aroma; wine lactone