Preparation And Modification Of Neohesperidin Derivatives And Their Application In Bitterness Modification

With the increasing concern about health,the demand of functional foods is growing rapidly.However,functional foods usually have poor taste,especially bitter taste.For the pursuit of health and good taste for consumers,concealing or eliminating bitter taste has become a challenge that should be met urgently in functional food industry.At present,it is a trend to vigorously develop natural,healthy bitter modifier in the food industry,instead of using traditional high sucrose masking methods.Neodiosmin and NHDC,as natural flavonoid with excellent functional active,can greatly mask the bitter taste of functional foods.In this paper,neodiosmin and NHDC were prepared and modified as bitterness modifier,and their modification applied on masking bitter taste.These findings would provide the theoretical and technical supports for the development of natural and healthy bitterness modifier in functional food applications.The main conclusions are in this paper as follows:This study is the preparation process of phloracetophenone-4'-?-neohesperidoside(PN),the obtained products are characterized with FT-IR,~1H NMR and MS methods,the preparation process of PN is optimized by factor trend analysis.The optimum process conditions for PN preparation are described as follows:the temperature is 100?,pH value is 6.57,stirring speed is 591 rpm,reaction time is 2.04 h,NaOH concentration is 15.85%,and liquid-solid ratio is 11.09.The response surface test of PN is carried out by using Design Expert software.The optimal parameters of PN synthesis as follow:reaction time is 2.03 h,stirring speed is 594 rpm,NaOH concentration is 15.86%,and liquid-solid ratio is 11.11.Single factor horizontal trend analysis and response surface optimization analysis show that the optimum process conditions of the two methods are basically the same.Under the optimum conditions,the yield of phloroacetophenone-4'-?--neohesperidin reached 78.10%by means of verification test and amplification test.This paper studies the synthesis of neohesperidin in PN under different catalytic systems.The catalytic system of L-proline+piperidine is selected as the catalyst for the synthesis of neohesperidin,and the results of obtained products test and characterization prove that the prepared product is neohesperidin.The preparation process of neohesperidin is optimized for each preparation factors of neohesperidin by factor trend analysis.The optimum conditions for preparation of neohesperidin are described as follows:Under normal pressure,with 95%ethanol as solvent,solvent dosage 10.00 mL,catalyst amount is 0.60 g,isovanillin is 0.40 g,100?boiling water bath heating,the reaction time is 10.63 h,stirring speed is 600 rpm,and neohesperidin yield is 87.62%under the optimum conditions.This study is the preparation of neodiosmin by dehydrogenation process of neohesperidin,the results of obtained products test and characterization prove that the prepared product is neodiosmin.This study investigates the preparation factors of neodiosmin by factor trend analysis,the optimum conditions for preparation of neodiosmin are described as follows:0.01 mol neohesperidin materials,42.17 mL pyridine liquid,0.01 mol iodine,the optimum pressure is 0.58 MPa in the iodine substitution reaction,the reaction temperature is100?boiling water bath heating,the reaction time is 8.11 h,stirring speed is 575 rpm,67.74 mL of 10.00%NaOH concentration,the crystallization optimal pH is 5.00.At the time,the study investigates the preparation NHDC process,the results of obtained products test and characterization prove that the prepared product is NHDC.The preparation process of NHDC is optimized for each preparation factors of NHDC by factor trend analysis,the optimum conditions for preparation of NHDC are described as follows:0.01 mol neohesperidin materials,7.34%NaOH concentration,liquid-solid ratio is 8.20,catalyst amount is 3.50%,the optimum pressure is 0.50 MPa in hydrogenation reaction,the reaction temperature is 41?boiling water bath heating,the reaction time is 9.12 h,stirring speed is 587 rpm,the crystallization optimal pH is 6.87.The modification of neodiosmin by encapsulation is study in this paper,neodiosmin,casein and konjac encapsulation system was used to mask limonin bitter.Compared to encapsulation without neodiosmin,single neodiosmin and physical mixtue of neodiosmin/casein/konjac,the neodiosmin encapsulation has a significant effect on bitterness reducation.Debitter of limonin under optimized neodiosmin encapsulation is dried by oven drying,vacuum drying,spray drying and freeze drying.Limonin with no bitterness was used as the reference,the characteristic indexes and sensory quality of the powder products were compared in terms of moisture absorption,dissolution rate,moisture content and bulk density of the products in different drying methods,the results show that the products prepared by freeze drying are of the best quality.The NHDC,casein and konjac encapsulation system were established,and the NHDC encapsulation is used to mask the corn peptide bitter.Compared to encapsulation without NHDC,single NHDC and physical mixtue of NHDC/casein/konjac,the NHDC encapsulation has a significant effect on bitterness reducation.Debitter of corn peptide under optimized NHDC encapsulation is dried by oven drying,vacuum drying,spray drying and freeze drying.Corn peptide with no bitterness was used as the reference,the characteristic indexes and sensory quality of the powder products were compared in terms of moisture absorption,dissolution rate,moisture content and bulk density of the products in different drying methods,the results show that the products prepared by spray drying are of the best quality.This paper research modification of neodiosmin by inclusion complex,and synthesize neodiosmin/?-cyclodextrin/L-lysine inclusion complex in the aqueous solution.Neodiosmin,?-cyclodextrin,L-lysine,physical mixture,and neodiosmin inclusion complex are analyzed by XRD,DSC,FT-IR,~1H NMR,and SEM,and result indicate inclusion complex form,Phase solubility illustrates that neodiosmin solubility improved significantly.A series of tests are conducted on the bitterness reducation of neodiosmin inclusion complexes,and result show that the bitterness reducation effect of neodiosmin inclusion complex on limonin is significantly improved,and better than other bitter inhibitors.This study synthesize NHDC/glucosyl-?-cyclodextrin inclusion complex via ultrasonic-assisted technique in the ethanol aqueous solution.The NHDC,G-?-CD,physical mixture and NHDC inclusion complex is analyzed by XRD,DSC,FT-IR,~1H NMR,and SEM.The NHDC inclusion process is optimized,and under the optimal synthetic condition,the NHDC payload and inclusion rate are obtained,and these results show that NHDC solubility is greatly improved.A series of tests are conducted on the bitterness reducation of NHDC inclusion complexes,and result show that the bitterness reducation effect of NHDC inclusion complex on corn peptide is significantly improved,as well as better than other bitter inhibitors.