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 timedependent
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.
Considerable evidence suggests that long-term pathological diabetes is a result of the accumulation of tissuemacromolecules that have been progressively modified by nonenzymatic glycation of protein. Methylglyoxal (MGO) is a highlyreactive endogenous dicarbonyl metabolite derived from multiple sources such as glucose and lipids and is thought to contributegreatly to protein glycation and the formation of advanced glycation end products (AGEs). In this study, we demonstrated forthe first time that both [6]-shogaol (6S) and [6]-gingerol (6G), the major active components in ginger, markedly trapped MGOin vitro and consequently formed mono-MGO adducts, 6S-MGO and 6G-MGO, which were purified from the respectivechemical reaction and characterized as novel compounds by NMR experiments and LC−MS/MS approaches. We revealed thatthe α-carbon of the carbonyl group in the side chain of 6S or 6G is the major active site for trapping MGO. We alsodemonstrated that 6S and 6G could effectively inhibit the formation of MGO-induced AGEs via trapping MGO in a timedependentmanner in the human serum albumin (HSA)−MGO system. Mono-MGO adducts, 6S-MGO and 6G-MGO, weredetermined 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 consumptionof ginger root extract may attenuate the progression of MGO-associated diabetic complications in patients.
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