Structural characterization of reaction products of caftaric acid and bisulfite present in a commercial wine using high resolution mass spectrometric and nuclear magnetic resonance techniques. (1st September 2017)

• Record Type: Journal Article
• Authors: Hayasaka, Yoji; Black, Cory A.; Hack, Jeremy; Smith, Paul
• Is Part Of: Food chemistry. Volume 230(2017)
• Page Start: 99
• Page End: 107
• Publication Date: 2017-09-01
• Subjects: Sulfur dioxide -- Bisulfite -- Caftaric acid -- Wine oxidation -- Mass spectrometry; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2017.03.005
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Caftaric acid and bisulfite reaction products present in wine were investigated. Five reaction products were found in wine using HPLC-MS and MS/MS. Three sulfonated and two sulfated caftaric acids were identified using NMR. The reaction products were found in wines regardless of vintages and varieties. Abstract: Reaction products of bisulfite and caftaric acid were found in wines containing sulfites as a preservative. Acidic compounds were separated from wine and analyzed by HPLC combined with DAD and QTOF mass spectrometer. HPLC chromatograms of the expected [M−H] − ion and UV absorption revealed the presence of five possible reaction products ( a – e ). These compounds were isolated then characterized by NMR and confirmed to be the reaction products as follows; 5-sulfo-( E )-caftaric acid ( a ), 2-sulfo-( Z )-caftaric acid ( b ), 2-sulfo-( E )-caftaric acid ( c ), ( E )-caftaric acid-4- O -sulfate ( d ) and ( E )-caftaric acid-3- O -sulfate ( e ). UV spectra and high resolution product ion spectra of the five compounds also supported their identity. The reaction products were confirmed to be commonly present in commercial wines across four vintages and two varieties. Their concentration was found to be as much as that of 2- S -glutathionyl caftaric acid, suggesting that bisulfite consistently competes as a nucleophile with glutathione for the o -quinone of caftaric acid.