title: New insights into an ancient antibrowning agent: formation of sulfophenolics in sodium hydrogen sulfite-treated potato extracts.
abstract: The effect of sodium hydrogen sulfite (S), used as antibrowning agent, on the phenolic profile of potato extracts was investigated. This extract was compared to one obtained in the presence of ascorbic acid (A). In the presence of A, two major compounds were obtained, 5-O-caffeoylquinic acid (5-CQA) and 4-O-caffeoyl quinic acid. With S, their 2'-sulfo-adducts were found instead, the structures of which were confirmed by nuclear magnetic resonance spectroscopy and mass spectrometry. Also, for minor caffeoyl derivatives and quercetin glycosides, the corresponding sulfo-adducts were observed. Feruloyl and sinapoyl derivatives were not chemically affected by the presence of S. Polyphenol oxidase (PPO) was thought to be responsible for the formation of the sulfo-adducts. This was confirmed by preparing 2'-sulfo-5-O-caffeoyl quinic acid in a model system using 5-CQA, sodium hydrogen sulfite, and PPO. This sulfo-adduct exhibited a small bathochromic shift (λmax 329 nm) as compared to 5-CQA (λmax 325 nm) and a strong hypochromic shift with an extinction coefficient of 9357±395 M(-1) cm(-1) as compared to 18494±196 M(-1) cm(-1), respectively. The results suggest that whenever S is used as an antibrowning agent, the O-quinone formed with PPO reacts with S to produce sulfo-O-diphenol, which does not participate in browning reactions.
authors.affiliation: Laboratory of Food Chemistry, Wageningen University, P.O. Box 8129, 6700EV Wageningen, The Netherlands.
authors.forename: Carlos-Eduardo
authors.initials: CE
authors.lastname: Narváez-Cuenca
authors.forename: Tomas F M
authors.initials: TF
authors.lastname: Kuijpers
authors.forename: Jean-Paul
authors.initials: JP
authors.lastname: Vincken
authors.forename: Pieter
authors.initials: P
authors.lastname: de Waard
authors.forename: Harry
authors.initials: H
authors.lastname: Gruppen
mesh_terms: D004156:Catechol Oxidase / Q000378:metabolism; D002726:Chlorogenic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D015416:Maillard Reaction / Q000187:drug effects*; D010636:Phenols / Q000378:metabolism*; D010936:Plant Extracts / Q000378:metabolism*; D011801:Quinic Acid / Q000031:analogs & derivatives / Q000378:metabolism; D011198:Solanum tuberosum / Q000187:drug effects / Q000378:metabolism*; D013447:Sulfites / Q000494:pharmacology*; D013457:Sulfur Compounds / Q000378:metabolism*
chemical_list: D004156:Catechol Oxidase; D002726:Chlorogenic Acid; D010636:Phenols; D010936:Plant Extracts; D011801:Quinic Acid; D013447:Sulfites; D013457:Sulfur Compounds; C569244:sodium hydrogen sulfite; C473200:5-caffeoylquinic acid; C042345:hydrogen sulfite