脂类食品体系中羧甲基赖氨酸生成机理的研究
摘要
近年来在食品中发现有较多的晚期糖基化末端产物（advanced glycation endproducts，AGEs），尤其是脂类加工的食品中AGEs的含量较高。大量动物实验和临床实验表明，食源性AGEs对人体健康具有潜在危害性。为了研究脂类食品中AGEs的生成机理，本论文选取羧甲基赖氨酸（Nε-carboxymethyllysine，CML）作为AGEs的代表，将CML的产生和食品加工过程相关联。按照从微观机理到宏观表象的整体研究思路，以模拟体系作为出发点，逐步将研究体系扩展到真实食品体系。从反应历程、中间产物、自由基和碳源四个角度深入探讨了脂类食品体系中CML的生成机理，为有效控制食品加工过程中潜在化学危害物的产生提供理论依据。
主要研究内容及成果如下。
（一）非脂类模拟体系中CML的化学反应动力学
研究了非脂类模拟体系赖氨酸（lysine，Lys）+葡萄糖（glucose，Glu）中CML的生成规律，为随后研究脂类对CML生成路径的作用机理提供基础。首先，建立Lys+Glu模拟体系，采用高效液相色谱-质谱仪（high performance liquid chromatography-fluorescence，HPLC-MS）结合外标法研究了其在100℃、80℃、60℃和40℃加热不同时间过程中，模拟体系中目标产物CML、中间产物果糖基赖氨酸（fructoselysine，FL）与乙二醛（glyoxal，GO）和原料Lys与Glu含量的生成规律。其次，通过添加邻苯二胺（o-phenylenediamine，OPD）阻断GO生成CML的方法研究了FL路径和GO路径对生成CML的贡献率大小。最后，根据可逆-连串-并行的复合反应机理，理论推导出100℃条件下CML、FL、GO、Lys和Glu的化学反应动力学公式，结合Origin软件的非线性拟合功能对实验数据进行拟合，得到CML各级反应的表观速率常数和表观动力学方程。结果表明，CML在100℃条件下具有热稳定性，能够在食品中积累。FL和GO作为生成食源性CML的重要中间产物，在食品加工过程都存在一个极大值点。100℃条件下FL路径生成CML占主导地位，贡献率为84.7%，而GO路径生成CML占次要地位，贡献率为15.3%。分别建立了100℃条件下FL路径和GO路径生成CML的表观动力学方程。因此，有望通过在食品加工过程中调控加工参数和添加抑制剂等方式来控制食源性CML的产生。
（二）脂类模拟体系中CML的生成机理
从自由基和碳源两个角度探讨了脂类模拟体系中CML的生成机理。
在自由基方面，首先利用Fenton试剂考察了羟基自由基（hydroxyl radical, OH·）对Lys+Glu+Fenton模拟体系和Lys+GO+Fenton模拟体系生成CML路径的作用。在此基础之上，研究了亚油酸（linoleic acid，Lin）、油酸（oleic acid，Ole）、三油酸甘油酯（trioleate，Tri）和甘油（glycerol，Gly）对Lys+Glu+Lipid模拟体系中OH·、CML、FL、GO和Glu含量的影响，以及对Lys+GO+Lipid模拟体系中CML和乙醛酸（glyoxalic acid，GOA）的影响。结果表明，OH·对美拉德反应体系中生成CML的三条路径都具有促进作用。Lin、Ole和Tri能够促使美拉德反应体系产生更多的OH·，这些OH·促进了模拟体系中的FL和GO向CML的转化。Gly对OH·具有清除作用，从而降低了模拟体系中的CML含量。就引发自由基而言，对CML的促进作用按照从大到小排列为：Ole﹥Lin﹥Tri﹥Glu﹥Gly。
在碳源方面，对模拟体系中的Glu和Gly分别进行13C同位素标记，通过追踪被标记碳原子通过GO路径生成CML的过程，证实油脂生成CML的新反应路径。通过计算CML含量中，通过GO路径分别来自Lin、Ole、Tri和Gly的比例，比较脂氧化和糖氧化对生成CML的贡献率。结果表明，Lin、Ole、Tri和Gly在氧化过程中产生的GO参与了CML的生成。在100℃条件下，相对于Glu对生成GO的贡献率而言，Lin、Ole和Tri对生成GO的贡献率在4.0h处达到极大值，分别为3.53%、3.08%和1.81%，然而，Gly对生成GO的贡献率随着加热时间的延长而逐渐增多，在8.0h处达到最大值99.29%。相对于Glu通过GO路径和FL路径生成CML的贡献率而言，Lin、Ole、Tri通过GO路径对生成CML的贡献率随着加热时间的延长而逐渐增多，在8.0h处达到最大值，分别为7.45%、5.31%和4.10%，Gly通过GO路径对生成CML的贡献率在6.0h处达到极大值10.33%。Lin、Ole、Tri和Gly都能够通过自身氧化断裂生成GO，提供生成CML的碳源。就中间产物而言，对CML的贡献按照从大到小排列为：FL路径（针对Glu）﹥Gly氧化产生GO路径﹥GO路径（针对Glu）﹥Lin氧化产生GO路径﹥Ole氧化产生GO路径﹥Tri氧化产生GO路径。因此，脂类对CML生成的促进作用来源于两个方面：（1）促使美拉德反应模拟体系产生更多OH·，促进CML的产生；（2）不饱和脂肪酸和Gly氧化产生GO，成为生成CML的碳源。
（三）植物油模拟体系中CML的生成规律
基于前述的模拟体系中CML生成机理，进一步将研究体系从脂类模拟体系扩展到半真实脂类食品体系——植物油模拟体系，即研究大豆油（soybean oil，Soybean）、玉米油（corn oil，Corn）、橄榄油（olive oil，Olive）、棕榈油（palm oil，Palm）和菜籽油（rape oil，Rape）等五种常用植物油对Lys+Glu+Oil模拟体系中OH·、目标产物CML、中间产物FL与GO含量的影响。结果表明，油脂能够促使美拉德反应模拟体系产生更多的OH·，这些OH·促进了模拟体系中的FL和GO向CML的转化。五种植物油对模拟体系中CML的促进作用按照从高到低排序为Soybean﹥Corn﹥Olive﹥Palm﹥Rape。对五种油脂中主要脂肪酸比例的分析表明，油脂对模拟体系中CML的促进作用和油脂中不饱和脂肪酸含量存在正相关性，即含有较多不饱和脂肪酸的油脂能够在美拉德反应模拟体系中引发较多的OH·，从而促进GO和FL向CML转化。因此，在食品加工过程中，含有较多不饱和脂肪酸的油脂更容易促进CML的产生。
（四）真实食品体系中CML的生成规律
将研究体系从半真实脂类食品体系进一步扩展到真实食品体系。选用一种氨基酸饮料作为非脂类真实食品体系的代表，选用牛奶作为脂类真实食品体系的代表。考察了氨基酸饮料在60℃保温箱里储存48h过程中的CML生成规律。在脱脂奶（skim milk，SM）和低乳糖奶（low lactose milk，LLM）中添加天然奶油，比较了3%、6%和9%奶油添加量对牛奶中CML生成的影响。结果表明，随着加热时间的延长，氨基酸饮料中CML含量逐渐增加。而牛奶在100℃条件下加热30min，其CML的含量随着加热时间的延长而逐渐增加，LLM比SM能够产生更多的CML。因此，在食品储藏过程中，食源性CML会随着储藏时间的延长而逐渐积累。在食品加工过程中，脂类食品体系中CML的含量随着油脂含量的增加而逐渐增加。
In recent years, advanced glycation end products (AGEs) are found to exist in commonlyconsumed foods, especially in fat diet. Many animal experiments and clinical experimentsshowed that food-derived AGEs were potentially hazardous to human health. In order to studythe formation mechanism of AGEs in fat diet, Nε-carboxymethyllysine (CML) was chose as arepresentative of AGEs. Its formation was associated with food production process. CMLresearch system was extended from simplest model system to real lipid food system in thispaper. CML formation mechanism was investigated from the aspects of reaction mechanism,intermediates, free radicals and carbon source to offer theory for controlling potentialhazardous materials in food production process. The main results are shown as follow.
(1) Chemical reaction kinetics of CML in non-lipid model system.
The formation rule of CML in lysine (Lys)+glucose (Glu) model system wasinvestigated so as to offer basis for mechanism of lipid effect on CML formation.
Firstly, CML and its key intermediates, fructoselysine (FL) and glyoxal (GO), weredetermined with high performance liquid chromatography-mass spectrum (HPLC-MS) inLys+Glu model system heated at100°C,80°C,60°C and40°C. Secondly, The contributionrates of FL and GO to CML were determined by inhibiting GO with o-phenylenediamine(OPD) method. Finally, according to reversible reaction, consecutive reaction and parallelreactions mechanism, CML, FL, GO, Lys and Glu formation kinetics equations weretheoretically deduced. Combining with non-linear fit function of Origin Software,experimental data were fitted to obtain apparent rate constants and apparent kinetics equations.It indicated that CML content could accumulate in food for its thermal stability. There wereboth FL and GO contents maximum points in their formation process. CML derived from FLplayed a major role with contribution rate of84.7%for CML formation, while CML derivedfrom GO played a minor role with contribution rate of15.3%for CML formation. CMLapparent kinetics equations through FL pathway and GO pathway were obtained respectively.Therefore, it is possible to control food-derived CML through adjusting processing variablesand adding inhibitors.
(2) Formation mechanism of CML in lipid model system.
The formation mechanism of CML was discussed in lipid model system from aspects offree radials and carbon resource.
In free radicals aspect, it was proved that hydroxyl radical (OH·) induced by Fentonreagent could promote CML formation in Lys+Glu+Fenton model system andLys+GO+Fenton model system. On the base of that, the effect of Lin, Ole, Tri and Gly onOH·, CML, FL, GO and Glu content in Lys+Glu+Lipid model system, and the effect of Lin,Ole, Tri and Gly on CML and glyoxalic acid (GOA) content in Lys+GO+Lipid model systemwere determined. It was shown that OH· induced by Fenton reagent could promote threepathways for CML formation in Maillard reaction. Lin, Ole and Tri could induce more OH· inMaillard reaction model system which promoted FL and GO conversion to CML. However,Gly could reduce CML content in model system for its scavenging OH· ability. Thepromoting CML formation abilities of lipids on modeling system were in the order of Ole﹥Lin﹥Tri﹥Glu﹥Gly.
In carbon resource aspect, Glu and Gly in model system were labeled with13C. Newpathway for CML formation from lipid was proved through tracing13C flow direction.Contribution rates of lipid oxidation and saccharide oxidation for CML formation werecompared through calculating CML content proportion formed from Lin, Ole, Tri and Gly. Itwas found that GO derived from Lin, Ole, Tri and Gly oxidation participated in CMLformation. In100°C heating condition, compared with Glu contribution rate to GO, thecontribution rates of Lin, Ole and Tri to GO reached their maximum value at4.0h with3.53%、3.08%and1.81%respectively. The contribution rate of Gly to GO increased withtime increasing and reached maximum value99.29%at8.0h. Compared with Glucontribution rate to CML, the contribution rates of Lin, Ole and Tri to CML formationincreased with time. They increased to reach their maximum value at8.0h with7.45%,5.31%and4.10%, respectively. The contribution rate of Gly to CML increased with time.They reached maximum value10.33%at6.0h. The promoting effect of Lin, Ole, Tri and Glyon CML formation through oxidation to GO were in the order of FL pathway﹥Gly﹥GOpathway﹥Lin﹥Ole﹥Tri. Therefore, the promoting effect of lipid on CML formationderived from two aspects: Inducing more OH· to promote CML formation; Offering carbonsource for CML formation through oxidation to GO.
(3) CML formation in vegetable oils model system.
Based on above mechanism of lipid effect on CML formation in model system, the lipidmodel system was extened from lipid model system to vegetable oils model system. Theeffect of five oils on OH·, CML, FL and GO content in Lys+Glu+Oil model system wasstudied. It was shown that vegetable oils including Soybean oil (Soybean), Corn oil (Corn), Olive oil (Olive), Palm oil (Palm) and Rape oil (Rape)) could induce more OH· in Maillardreaction model system, which promoted FL and GO conversion to CML. The promotioneffect of five oils on CML formation was in the order of Soybean﹥Corn﹥Olive﹥Palm﹥Rape. Fatty acid analysis for five oils showed that the more unsaturated fatty acid the oils had,the more OH· they induced in model system. Therefore, oils with more unsaturated fatty acidin food production process were easier to increase CML formation.
(4) CML formation in real food system.
This part extended vegetable oils model system to real lipid food system. An amino acidbeverage was chose as non-lipid food system, and milk was chose as lipid food system. Theamino acid beverage was storaged at60°C for48h to determine CML formation. It indicatedthat CML content in beverage increased with time. Natural cream of3%,6%and9%wasadded to skim milk (SM) and low lactose milk (LLM) to compared CML formation. Itindicated that under the condition of100°C heating for30min, CML increased with time.LLM generated more CML than SM. Therefore, CML could accumulate in food storageprocess and CML content in lipid system increased with oil content increasing in foodproduction process.
主要研究内容及成果如下。
（一）非脂类模拟体系中CML的化学反应动力学
研究了非脂类模拟体系赖氨酸（lysine，Lys）+葡萄糖（glucose，Glu）中CML的生成规律，为随后研究脂类对CML生成路径的作用机理提供基础。首先，建立Lys+Glu模拟体系，采用高效液相色谱-质谱仪（high performance liquid chromatography-fluorescence，HPLC-MS）结合外标法研究了其在100℃、80℃、60℃和40℃加热不同时间过程中，模拟体系中目标产物CML、中间产物果糖基赖氨酸（fructoselysine，FL）与乙二醛（glyoxal，GO）和原料Lys与Glu含量的生成规律。其次，通过添加邻苯二胺（o-phenylenediamine，OPD）阻断GO生成CML的方法研究了FL路径和GO路径对生成CML的贡献率大小。最后，根据可逆-连串-并行的复合反应机理，理论推导出100℃条件下CML、FL、GO、Lys和Glu的化学反应动力学公式，结合Origin软件的非线性拟合功能对实验数据进行拟合，得到CML各级反应的表观速率常数和表观动力学方程。结果表明，CML在100℃条件下具有热稳定性，能够在食品中积累。FL和GO作为生成食源性CML的重要中间产物，在食品加工过程都存在一个极大值点。100℃条件下FL路径生成CML占主导地位，贡献率为84.7%，而GO路径生成CML占次要地位，贡献率为15.3%。分别建立了100℃条件下FL路径和GO路径生成CML的表观动力学方程。因此，有望通过在食品加工过程中调控加工参数和添加抑制剂等方式来控制食源性CML的产生。
（二）脂类模拟体系中CML的生成机理
从自由基和碳源两个角度探讨了脂类模拟体系中CML的生成机理。
在自由基方面，首先利用Fenton试剂考察了羟基自由基（hydroxyl radical, OH·）对Lys+Glu+Fenton模拟体系和Lys+GO+Fenton模拟体系生成CML路径的作用。在此基础之上，研究了亚油酸（linoleic acid，Lin）、油酸（oleic acid，Ole）、三油酸甘油酯（trioleate，Tri）和甘油（glycerol，Gly）对Lys+Glu+Lipid模拟体系中OH·、CML、FL、GO和Glu含量的影响，以及对Lys+GO+Lipid模拟体系中CML和乙醛酸（glyoxalic acid，GOA）的影响。结果表明，OH·对美拉德反应体系中生成CML的三条路径都具有促进作用。Lin、Ole和Tri能够促使美拉德反应体系产生更多的OH·，这些OH·促进了模拟体系中的FL和GO向CML的转化。Gly对OH·具有清除作用，从而降低了模拟体系中的CML含量。就引发自由基而言，对CML的促进作用按照从大到小排列为：Ole﹥Lin﹥Tri﹥Glu﹥Gly。
在碳源方面，对模拟体系中的Glu和Gly分别进行13C同位素标记，通过追踪被标记碳原子通过GO路径生成CML的过程，证实油脂生成CML的新反应路径。通过计算CML含量中，通过GO路径分别来自Lin、Ole、Tri和Gly的比例，比较脂氧化和糖氧化对生成CML的贡献率。结果表明，Lin、Ole、Tri和Gly在氧化过程中产生的GO参与了CML的生成。在100℃条件下，相对于Glu对生成GO的贡献率而言，Lin、Ole和Tri对生成GO的贡献率在4.0h处达到极大值，分别为3.53%、3.08%和1.81%，然而，Gly对生成GO的贡献率随着加热时间的延长而逐渐增多，在8.0h处达到最大值99.29%。相对于Glu通过GO路径和FL路径生成CML的贡献率而言，Lin、Ole、Tri通过GO路径对生成CML的贡献率随着加热时间的延长而逐渐增多，在8.0h处达到最大值，分别为7.45%、5.31%和4.10%，Gly通过GO路径对生成CML的贡献率在6.0h处达到极大值10.33%。Lin、Ole、Tri和Gly都能够通过自身氧化断裂生成GO，提供生成CML的碳源。就中间产物而言，对CML的贡献按照从大到小排列为：FL路径（针对Glu）﹥Gly氧化产生GO路径﹥GO路径（针对Glu）﹥Lin氧化产生GO路径﹥Ole氧化产生GO路径﹥Tri氧化产生GO路径。因此，脂类对CML生成的促进作用来源于两个方面：（1）促使美拉德反应模拟体系产生更多OH·，促进CML的产生；（2）不饱和脂肪酸和Gly氧化产生GO，成为生成CML的碳源。
（三）植物油模拟体系中CML的生成规律
基于前述的模拟体系中CML生成机理，进一步将研究体系从脂类模拟体系扩展到半真实脂类食品体系——植物油模拟体系，即研究大豆油（soybean oil，Soybean）、玉米油（corn oil，Corn）、橄榄油（olive oil，Olive）、棕榈油（palm oil，Palm）和菜籽油（rape oil，Rape）等五种常用植物油对Lys+Glu+Oil模拟体系中OH·、目标产物CML、中间产物FL与GO含量的影响。结果表明，油脂能够促使美拉德反应模拟体系产生更多的OH·，这些OH·促进了模拟体系中的FL和GO向CML的转化。五种植物油对模拟体系中CML的促进作用按照从高到低排序为Soybean﹥Corn﹥Olive﹥Palm﹥Rape。对五种油脂中主要脂肪酸比例的分析表明，油脂对模拟体系中CML的促进作用和油脂中不饱和脂肪酸含量存在正相关性，即含有较多不饱和脂肪酸的油脂能够在美拉德反应模拟体系中引发较多的OH·，从而促进GO和FL向CML转化。因此，在食品加工过程中，含有较多不饱和脂肪酸的油脂更容易促进CML的产生。
（四）真实食品体系中CML的生成规律
将研究体系从半真实脂类食品体系进一步扩展到真实食品体系。选用一种氨基酸饮料作为非脂类真实食品体系的代表，选用牛奶作为脂类真实食品体系的代表。考察了氨基酸饮料在60℃保温箱里储存48h过程中的CML生成规律。在脱脂奶（skim milk，SM）和低乳糖奶（low lactose milk，LLM）中添加天然奶油，比较了3%、6%和9%奶油添加量对牛奶中CML生成的影响。结果表明，随着加热时间的延长，氨基酸饮料中CML含量逐渐增加。而牛奶在100℃条件下加热30min，其CML的含量随着加热时间的延长而逐渐增加，LLM比SM能够产生更多的CML。因此，在食品储藏过程中，食源性CML会随着储藏时间的延长而逐渐积累。在食品加工过程中，脂类食品体系中CML的含量随着油脂含量的增加而逐渐增加。
In recent years, advanced glycation end products (AGEs) are found to exist in commonlyconsumed foods, especially in fat diet. Many animal experiments and clinical experimentsshowed that food-derived AGEs were potentially hazardous to human health. In order to studythe formation mechanism of AGEs in fat diet, Nε-carboxymethyllysine (CML) was chose as arepresentative of AGEs. Its formation was associated with food production process. CMLresearch system was extended from simplest model system to real lipid food system in thispaper. CML formation mechanism was investigated from the aspects of reaction mechanism,intermediates, free radicals and carbon source to offer theory for controlling potentialhazardous materials in food production process. The main results are shown as follow.
(1) Chemical reaction kinetics of CML in non-lipid model system.
The formation rule of CML in lysine (Lys)+glucose (Glu) model system wasinvestigated so as to offer basis for mechanism of lipid effect on CML formation.
Firstly, CML and its key intermediates, fructoselysine (FL) and glyoxal (GO), weredetermined with high performance liquid chromatography-mass spectrum (HPLC-MS) inLys+Glu model system heated at100°C,80°C,60°C and40°C. Secondly, The contributionrates of FL and GO to CML were determined by inhibiting GO with o-phenylenediamine(OPD) method. Finally, according to reversible reaction, consecutive reaction and parallelreactions mechanism, CML, FL, GO, Lys and Glu formation kinetics equations weretheoretically deduced. Combining with non-linear fit function of Origin Software,experimental data were fitted to obtain apparent rate constants and apparent kinetics equations.It indicated that CML content could accumulate in food for its thermal stability. There wereboth FL and GO contents maximum points in their formation process. CML derived from FLplayed a major role with contribution rate of84.7%for CML formation, while CML derivedfrom GO played a minor role with contribution rate of15.3%for CML formation. CMLapparent kinetics equations through FL pathway and GO pathway were obtained respectively.Therefore, it is possible to control food-derived CML through adjusting processing variablesand adding inhibitors.
(2) Formation mechanism of CML in lipid model system.
The formation mechanism of CML was discussed in lipid model system from aspects offree radials and carbon resource.
In free radicals aspect, it was proved that hydroxyl radical (OH·) induced by Fentonreagent could promote CML formation in Lys+Glu+Fenton model system andLys+GO+Fenton model system. On the base of that, the effect of Lin, Ole, Tri and Gly onOH·, CML, FL, GO and Glu content in Lys+Glu+Lipid model system, and the effect of Lin,Ole, Tri and Gly on CML and glyoxalic acid (GOA) content in Lys+GO+Lipid model systemwere determined. It was shown that OH· induced by Fenton reagent could promote threepathways for CML formation in Maillard reaction. Lin, Ole and Tri could induce more OH· inMaillard reaction model system which promoted FL and GO conversion to CML. However,Gly could reduce CML content in model system for its scavenging OH· ability. Thepromoting CML formation abilities of lipids on modeling system were in the order of Ole﹥Lin﹥Tri﹥Glu﹥Gly.
In carbon resource aspect, Glu and Gly in model system were labeled with13C. Newpathway for CML formation from lipid was proved through tracing13C flow direction.Contribution rates of lipid oxidation and saccharide oxidation for CML formation werecompared through calculating CML content proportion formed from Lin, Ole, Tri and Gly. Itwas found that GO derived from Lin, Ole, Tri and Gly oxidation participated in CMLformation. In100°C heating condition, compared with Glu contribution rate to GO, thecontribution rates of Lin, Ole and Tri to GO reached their maximum value at4.0h with3.53%、3.08%and1.81%respectively. The contribution rate of Gly to GO increased withtime increasing and reached maximum value99.29%at8.0h. Compared with Glucontribution rate to CML, the contribution rates of Lin, Ole and Tri to CML formationincreased with time. They increased to reach their maximum value at8.0h with7.45%,5.31%and4.10%, respectively. The contribution rate of Gly to CML increased with time.They reached maximum value10.33%at6.0h. The promoting effect of Lin, Ole, Tri and Glyon CML formation through oxidation to GO were in the order of FL pathway﹥Gly﹥GOpathway﹥Lin﹥Ole﹥Tri. Therefore, the promoting effect of lipid on CML formationderived from two aspects: Inducing more OH· to promote CML formation; Offering carbonsource for CML formation through oxidation to GO.
(3) CML formation in vegetable oils model system.
Based on above mechanism of lipid effect on CML formation in model system, the lipidmodel system was extened from lipid model system to vegetable oils model system. Theeffect of five oils on OH·, CML, FL and GO content in Lys+Glu+Oil model system wasstudied. It was shown that vegetable oils including Soybean oil (Soybean), Corn oil (Corn), Olive oil (Olive), Palm oil (Palm) and Rape oil (Rape)) could induce more OH· in Maillardreaction model system, which promoted FL and GO conversion to CML. The promotioneffect of five oils on CML formation was in the order of Soybean﹥Corn﹥Olive﹥Palm﹥Rape. Fatty acid analysis for five oils showed that the more unsaturated fatty acid the oils had,the more OH· they induced in model system. Therefore, oils with more unsaturated fatty acidin food production process were easier to increase CML formation.
(4) CML formation in real food system.
This part extended vegetable oils model system to real lipid food system. An amino acidbeverage was chose as non-lipid food system, and milk was chose as lipid food system. Theamino acid beverage was storaged at60°C for48h to determine CML formation. It indicatedthat CML content in beverage increased with time. Natural cream of3%,6%and9%wasadded to skim milk (SM) and low lactose milk (LLM) to compared CML formation. Itindicated that under the condition of100°C heating for30min, CML increased with time.LLM generated more CML than SM. Therefore, CML could accumulate in food storageprocess and CML content in lipid system increased with oil content increasing in foodproduction process.
引文
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