title: Bioactive ginger constituents alleviate protein glycation by trapping methylglyoxal.
abstract: Considerable evidence suggests that long-term pathological diabetes is a result of the accumulation of tissue macromolecules that have been progressively modified by nonenzymatic glycation of protein. Methylglyoxal (MGO) is a highly reactive endogenous dicarbonyl metabolite derived from multiple sources such as glucose and lipids and is thought to contribute greatly to protein glycation and the formation of advanced glycation end products (AGEs). In this study, we demonstrated for the first time that both [6]-shogaol (6S) and [6]-gingerol (6G), the major active components in ginger, markedly trapped MGO in vitro and consequently formed mono-MGO adducts, 6S-MGO and 6G-MGO, which were purified from the respective chemical reaction and characterized as novel compounds by NMR experiments and LC-MS/MS approaches. We revealed that the α-carbon of the carbonyl group in the side chain of 6S or 6G is the major active site for trapping MGO. We also demonstrated that 6S and 6G could effectively inhibit the formation of MGO-induced AGEs via trapping MGO in a time-dependent manner in the human serum albumin (HSA)-MGO system. Mono-MGO adducts, 6S-MGO and 6G-MGO, were determined to be the major conjugates in 6S- and 6G-treated HSA-MGO assays, respectively, using LC-ESI-MS techniques. These findings showed the potential effects of 6S and 6G on the prevention of protein glycation, suggesting regular consumption of ginger root extract may attenuate the progression of MGO-associated diabetic complications in patients.
authors.affiliation: Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus , 500 Laureate Way, Kannapolis, North Carolina 28081, United States.
authors.forename: Yingdong
authors.initials: Y
authors.lastname: Zhu
authors.affiliation: Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus , 500 Laureate Way, Kannapolis, North Carolina 28081, United States.
authors.forename: Yantao
authors.initials: Y
authors.lastname: Zhao
authors.affiliation: Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus , 500 Laureate Way, Kannapolis, North Carolina 28081, United States.
authors.forename: Pei
authors.initials: P
authors.lastname: Wang
authors.affiliation: Department of Health Science, College of Arts & Sciences, Qatar University , Doha 2713, Qatar.
authors.forename: Mohamed
authors.initials: M
authors.lastname: Ahmedna
authors.affiliation: Center for Excellence in Post-Harvest Technologies, North Carolina Agricultural and Technical State University, North Carolina Research Campus , 500 Laureate Way, Kannapolis, North Carolina 28081, United States.
authors.forename: Shengmin
authors.initials: S
authors.lastname: Sang
mesh_terms: D002853:Chromatography, Liquid; D020939:Zingiber officinale / Q000378:metabolism*; D017127:Glycation End Products, Advanced; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D011506:Proteins / Q000378:metabolism*; D011765:Pyruvaldehyde / Q000378:metabolism*; D053719:Tandem Mass Spectrometry
chemical_list: D017127:Glycation End Products, Advanced; D011506:Proteins; D011765:Pyruvaldehyde