Effect Of Chlorogenic Acid And Its Analogues On HMF Formation During Maillard Reaction

Hydroxymethylfurfural(HMF) is an endogenous contaminants occuring in food heatprocessing and storage, its safety aroused more concern in recent years. In this research, a aspartic acid / fructose Maillard model system(to model prune drying) was established to investigate the effect of phenolic acid on the formation and elimination of HMF under different reaction conditions. Moreover, chlorogenic acid along with six kinds of its analogues were used to explore which functional group in the molecule of chlorogenic acid play key role in HMF generation; also, the reactive dicarbonyl intermediates were detected to identify which reaction steps influenced by chlorogenic acid during Maillard reaction. The main results are as follows.1.Chlorogenic acid and its analogues influenced the formation and elimination of HMF(1) In aspartic acid and fructose model reacted system at p H=3.0 and 80 ℃ or 90 ℃,chlorogenic acid at three addition level promoted the HMF generation. The promoting ratio was 26.5% or 21.8% at 50 μmol/m L respectively. While reacted at 160℃, the promoting ratio was 11.2% at 0.5 μmol/m L.(2) p H is an important factor affecting HMF content. The yield of HMF is very low at p H=5.7,but significantly increased at p H=3.0, which may be due to the chlorogenic acid promoting fructose dehydration in acidic conditions.(3) Chlorogenic acid can promote the generation of HMF, but quinonoid chlorogenic acid exhibited 20.7% inhibitory rate. The mechanism may be quinoid chlorogenic acid is easy to combain with amino acids to generate schiff base or Michael adducts, thus inhibiting the binding of fructose and amino acids, resulting in the reduce of the content of HMF.(4)Aspartic acid and fructose reacted 48 h at 90 ℃ at p H=3.0. Chlorogenic acid and its analogues can promote HMF generation at 0.5 μmol/m L, the promoting effects was: quinic acid~chlorogenic acid>P- coumaric acid~ caffeic acid> Catechol~trans-3-Hydroxycinnamic acid~ protocatechuic~control group.(5) HMF and aspartic acid can react to make the original HMF to be consumed, but chlorogenic acid and its quinoid derivatives can inhibit the HMF abatement with a inhibition rate of 38.3% and 34.7%. But no evidence showed HMF combained with fructose.2. Effects of chlorogenic acid on the dicarbonyl compounds in Maillard system(1) The growing trend of 3-deoxyglucosone is synchronous to the HMF under acidic conditions(p H=3.0) at 90℃.It proved that chlorogenic acid can promote the generation of3-deoxyglucosone to increase the content of HMF.(2) Under acidic conditions(pH=3.0), comparing to HMF the content of furfural and methylglyoxal was very few, and glyoxal wasn’t found. Chlorogenic acid showed no significant effect on their formation. It show that chlorogenic acid can not influence the content of HMF through tne path of glyoxal and the path of glyceraldehyde and methylglyoxal.