First identification of 4-S-glutathionyl-4-methylpentan-2-one, a potential precursor of 4-mercapto-4-methylpentan-2-one, in Sauvignon Blanc juice

Journal of Agricultural and Food Chemistry
Bruno FedrizziDavid W Jeffery

Abstract

The identification of 4-S-glutathionyl-4-methylpentan-2-one (glut-4-MMP) by high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) experiments in a Sauvignon Blanc juice extract is described. Synthesis of an authentic reference compound enabled confirmation of the presence of glut-4-MMP in a Sauvignon Blanc juice for the first time. The juice extract was obtained by batch-wise percolation of 6 L of juice through a sintered glass funnel packed with C18 sorbent, followed by further purification using low-pressure chromatography on C18. Analysis of the juice extract revealed a chromatographic peak with the same retention time and mass spectrum as the synthetic reference compound, and spiking experiments verified the findings. The presence of glut-4-MMP in grape juice may be related to the biosynthesis of the relevant S-cysteinyl conjugate and, subsequently, to the formation of aroma-active 4-mercapto-4-methylpentan-2-one (4-MMP). This compound has a very low reported sensory threshold (3 ng/L) in wine and is partially responsible for the aromas that are important to the quality and style of some wine varieties.

References

Mar 1, 1997·Journal of Bacteriology·S Vuilleumier
Nov 4, 2004·FEMS Microbiology Letters·Kate S HowellMiguel A de Barros Lopes
Jan 31, 2007·Applied Microbiology and Biotechnology·J H Swiegers, I S Pretorius

❮ Previous
Next ❯

Citations

Jun 12, 2012·Applied Microbiology and Biotechnology·Michael J Harsch, Richard C Gardner
Sep 4, 2012·Applied Microbiology and Biotechnology·Antonio G CordenteIsak S Pretorius
Jul 26, 2011·Chemical Reviews·Aurélie RolandFlorine Cavelier
Apr 1, 2011·Journal of Agricultural and Food Chemistry·Dimitra L Capone, David W Jeffery
Dec 18, 2012·Journal of Agricultural and Food Chemistry·Engela C KritzingerWessel J du Toit
Jan 19, 2010·Phytochemistry·David P DixonRobert Edwards
Apr 16, 2016·Food Chemistry·Tomás Román VillegasGiorgio Nicolini
Aug 9, 2016·BMC Plant Biology·Pierre HelwiCornelis van Leeuwen
Oct 25, 2016·Journal of Bioscience and Bioengineering·Sachiko Iizuka-FurukawaYoshinori Wakai
Jan 27, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ignacio BeldaM Victoria Moreno-Arribas
Feb 22, 2017·Journal of Agricultural and Food Chemistry·Mango ParkerMarkus J Herderich
Mar 2, 2018·Applied Microbiology and Biotechnology·Santiago Benito
Mar 9, 2018·Applied Microbiology and Biotechnology·Laura ChasseriaudMarina Bely
Jul 29, 2018·Applied Microbiology and Biotechnology·Javier RuizSantiago Benito
Dec 11, 2019·Biomolecules·Vicente Ferreira, Ricardo Lopez
Feb 23, 2020·Journal of the Science of Food and Agriculture·Giorgio NicoliniRoberto Larcher
Oct 17, 2017·Scientific Reports·Andreja VanzoKlemen Lisjak
Aug 5, 2019·Applied Microbiology and Biotechnology·Javier RuizSantiago Benito
Jun 27, 2020·Analytical and Bioanalytical Chemistry·Susanne DekkerRoberto Larcher
Sep 1, 2020·Food Chemistry·Hugo BonnaffouxFlorine Cavelier
Mar 5, 2010·Journal of Agricultural and Food Chemistry·Aurélie RolandRémi Schneider
Sep 10, 2010·Journal of Agricultural and Food Chemistry·Aurélie RolandFlorine Cavelier

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.