title: Identification and quantification of adducts between oxidized rosmarinic acid and thiol compounds by UHPLC-LTQ-Orbitrap and MALDI-TOF/TOF tandem mass spectrometry.
abstract: LTQ Orbitrap MS/MS was used to identify the adducts between quinones derived from rosmarinic acid (RosA) and thiol compounds, including cysteine (Cys), glutathione (GSH), and peptides digested from myosin. Two adducts of quinone-RosA/Cys and quinone-RosA/2Cys, one quinone-RosA/GSH adduct, and three quinone-RosA/peptide adducts were identified by extracted ion and MS(2) fragment ion chromatograms. By using MALDI-TOF/TOF MS, the adduction reaction between RosA and myosin in myofibrillar protein isolates was determined, demonstrating that the accurate reaction site was at Cys949 of myosin. The effect of reaction conditions, including stirring time, temperature, and oxidative stress, on the formation of adducts was further investigated. The formation of quinone-RosA/Cys and quinone-RosA/GSH increased with stirring time. Both adducts increased with temperature, whereas the reactivity of the addition reaction of GSH was higher than that of Cys. With increasing oxidation stress, the formation of quinone-RosA/GSH adduct increased and that of quinone-RosA/Cys adduct decreased.
authors.affiliation: Synergetic Innovative Center of Food Safety and Nutrition, Key Laboratory of Meat Processing and Quality Control, Ministry of Education, and Key Laboratory of Animal Products Processing, Ministry of Agriculture, College of Food Science and Technology, Nanjing Agricultural University , Nanjing 210095, People's Republic of China.
authors.forename: Chang-bo
authors.initials: CB
authors.lastname: Tang
authors.forename: Wan-gang
authors.initials: WG
authors.lastname: Zhang
authors.forename: Chen
authors.initials: C
authors.lastname: Dai
authors.forename: Hui-xia
authors.initials: HX
authors.lastname: Li
authors.forename: Xing-lian
authors.initials: XL
authors.lastname: Xu
authors.forename: Guang-hong
authors.initials: GH
authors.lastname: Zhou
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D002934:Cinnamates / Q000032:analysis* / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D053630:Depsides / Q000032:analysis* / Q000737:chemistry*; D005978:Glutathione / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods*; D009218:Myosins / Q000737:chemistry; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D011809:Quinones / Q000032:analysis / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Q000379:methods; D013438:Sulfhydryl Compounds / Q000032:analysis* / Q000737:chemistry*; D053719:Tandem Mass Spectrometry / Q000379:methods; D000097123:Rosmarinic Acid
chemical_list: D002934:Cinnamates; D003545:Cysteine; D053630:Depsides; D005978:Glutathione; D009218:Myosins; D011809:Quinones; D013438:Sulfhydryl Compounds; D000097123:Rosmarinic Acid
keywords: LTQ Orbitrap; MALDI-TOF/TOF; adduct; myofibrillar protein isolate; reaction conditions; rosmarinic acid; thiol compounds