CN105918772B - Carboxymethyl lysine eliminating agent and application thereof - Google Patents
Carboxymethyl lysine eliminating agent and application thereof Download PDFInfo
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- CN105918772B CN105918772B CN201610375742.1A CN201610375742A CN105918772B CN 105918772 B CN105918772 B CN 105918772B CN 201610375742 A CN201610375742 A CN 201610375742A CN 105918772 B CN105918772 B CN 105918772B
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 15
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- 235000012734 epicatechin Nutrition 0.000 claims description 13
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
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- IQPNAANSBPBGFQ-UHFFFAOYSA-N luteolin Chemical compound C=1C(O)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C(O)=C1 IQPNAANSBPBGFQ-UHFFFAOYSA-N 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23C—DAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
- A23C7/00—Other dairy technology
- A23C7/04—Removing unwanted substances other than lactose or milk proteins from milk
- A23C7/043—Removing unwanted substances other than lactose or milk proteins from milk using chemicals in liquid or solid state, e.g. flocculating, adsorbing or extracting agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention discloses a carboxymethyl lysine eliminating agent and application thereof, wherein the eliminating agent is a quinone substance formed by oxidizing polyphenol containing catechol or pyrogallol structural units. The use of the elimination agent for reducing the content of carboxymethyl lysine in a food system. The quinone substance has stronger elimination capability on AGEs in a food system with neutral or alkaline pH, and can effectively reduce the CML level of the system when being added after the food system generates CML or when the food system does not generate CML.
Description
Technical Field
The invention relates to the field of food processing, in particular to a carboxymethyl lysine (CML) eliminating preparation which can be widely used as a food additive by capturing CML to reduce the content of CML generated in a food system.
Background
Advanced glycation end products (AGEs) are a class of highly oxidized compounds produced by food or organisms late in the maillard reaction. The prior research shows that AGEs can be related to the generation and development of diabetes, chronic heart failure, atherosclerosis and other diseases. The food-derived AGEs are absorbed into human body via digestive tract, and can improve AGEs level of human body. The long-term intake of excessive food-borne AGEs, especially free AGEs (glycated amino acids), can cause potential health hazards to the human body.
The existing means for reducing the content of AGEs mainly comprises the following steps of inhibiting the generation of AGEs: 1) antioxidants, capable of scavenging systemic radicals, inhibit free radical mediated conversion of Amadori products to AGEs, such as: vERutin, ferulic acid and VCQuercetin, carnosine, etc.; 2) the dicarbonyl compound capture agent can capture intermediate glyoxal formed by AGEs so as to inhibit the formation of AGEs, such as: aminoguanidine (AG), pyridoxamine (V)B6) Etc.; 3) the amino competitor has a molecular structure containing amino groups which can compete with amino groups on lysine to generate Maillard reaction so as to inhibit the generation of AGEs, such as: vB1And derivatives thereof (thiamine monophosphate, thiamine pyrophosphate), and the like.
Taking typical AGEs carboxymethyl lysine (CML) as an example, the possible paths of the existing inhibitor for reducing the CML content of the system are shown in fig. 1, and all the possible paths are inhibition on part of paths for forming CML, so that the inhibitor needs to be added before the CML is formed in the system to achieve the effect of reducing the CML level. In actual production, a food system often contains a certain level of AGEs before the inhibitor is added, and the existing inhibitor cannot completely inhibit the production of the AGEs of the system (the inhibition rate is about 10% -50%), however, for the AGEs existing in the food system, the existing means cannot eliminate the AGEs.
At present, no research is specially aimed at eliminating AGEs in food, and no report about applying AGEs eliminator to food processing is available.
Disclosure of Invention
In order to solve the problems, the invention aims to provide a CML remover, and particularly relates to the effect of quinone substances formed by oxidation of polyphenol with catechol or pyrogallol structure on removing CML in a simulated food system. The elimination agent can achieve the aim of eliminating CML by capturing CML in the system under certain conditions, and the capture principle is shown in figure 2.
The purpose of the invention is realized by the following technical scheme:
a carboxymethyl lysine eliminating agent is a quinone substance formed by oxidizing polyphenol containing catechol or pyrogallol structural units.
The polyphenol comprises 4-methylcatechol, epicatechin gallate, caffeic acid, quercetin, epigallocatechin gallate, epigallocatechin, luteolin, and rutin.
The use of the elimination agent for reducing the content of carboxymethyl lysine in a food system.
The eliminating agent is added into a food system, and the pH value of the system is controlled to be more than or equal to 7. Preferably, the pH of the system is 8.
The reaction temperature of the system is 25-100 ℃.
The addition amount of the eliminating agent is 2-3% of the lysine content of the system.
The elimination agent may be added after the food system has not produced or has produced CML.
Wherein the food system comprises dairy products, grains and products thereof, seasonings, meat and products thereof, and canned products.
In a simulated food system (glucose-lysine system), the additive of a quinone substance and CML formed by polyphenol containing catechol or pyrogallol structural units is identified by liquid chromatography-tandem mass spectrometry (LC-MS/MS). According to the stability of the quinones formed, a classification can be made: two categories of stable quinones and easily polymerizable quinones.
The specific steps of the identification of the addition product of the stable quinones substances and the CML are as follows:
(1) preparing a solution with CML of 10mM and quinone substances of 1mM by using 0.2M phosphate buffer solution (pH 7.0);
(2) stirring the above mixed solution at room temperature for 1min, treating with 0.22 μm microfiltration membrane, and performing structural identification on the adduct by LC-ESI-MS/MS.
The model of the LC is HP 1100, and the detection conditions are as follows:
a chromatographic column: ZIC-HILIC chromatographic column of 2.1 × 150mm, 3.5 μm
Column temperature: 25 deg.C
Mobile phase: a: ammonium acetate in water (6.5 mM)/acetonitrile (10:90, pH 5.5); b: ammonium acetate in water (6.5 mM)/acetonitrile (40:60, pH 5.5); gradient elution
Flow rate: 0.1mL/min
Sample introduction amount: 10 mu L of the solution;
the ESI-MS/MS model is HP 1100, and the detection conditions are as follows:
an ion source: ESI+
Drying gas temperature: 200 deg.C
Atomization air pressure: 50psi
Secondary fragmentation voltage: 1.00V
Scanning range: m/z 50-750
The specific steps for examining the CML capturing capability of the stable quinones are as follows:
(1) preparing a quinone solution with 0.2M phosphate buffer (pH 4.5) to a concentration of 0.08 mM;
(2) preparing a solution with CML of 1-10mM by using 0.2M phosphate buffer solution;
(3) the solutions of (1) and (2) above were mixed in equal volumes in a stock-flow mixing chamber and the pH was 5.0, 7.0 or 8.0;
(4) the kinetics of the reaction of 4MBQ with CML were determined by monitoring the change in absorbance of the reaction system in the UV-visible region (200 and 750nm) at 25 ℃ using Stopped-flow.
The method comprises the following specific steps of identifying the addition product of easily polymerized quinones and CML:
(1) A0.2M phosphate buffer (pH 8.0) was used to formulate a solution with 0.1M lysine (Lys) and 0.1M glucose (Glu) to simulate a food system;
(2) 2-3% of quinone formed by oxidation of polyphenol containing catechol or pyrogallol structure is added into the simulated food system in the step (1);
(3) heating the sample in water bath at 80 ℃ or 100 ℃ for 1 h;
(4) taking 1mL of heated sample, and adding distilled water to a constant volume of 5 mL;
(5) 1mL of the dilution was treated with a 0.22 μm microfiltration membrane and the adduct was structurally characterized using UPLC-ESI-MS/MS.
The UPLC adopts an Agilent SB1290 model, and the detection conditions are as follows:
a chromatographic column: agilent SB-C18Chromatographic column 2.1X 50mm, 1.8 μm
Column temperature: 25 deg.C
Mobile phase: A) formic acid: water-1: 1000(v: v), B) acetonitrile
Gradient elution procedure: 0min (85% A) -4min (15% A) -8min (15% A) -10min (85% A);
flow rate: 0.2mL/min
Sample introduction amount: 5 mu L of the solution;
the mass spectrum adopts a model as maxis Impact, and the detection conditions are as follows:
an ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Drying gas temperature: 180 deg.C
The pressure of the sprayer is as follows: 0.3bar
Mass to charge ratio scan range: m/z50-1000
In the invention, catechol is oxidized to form the catechol, and then the catechol can directly react with CML so as to achieve the aim of eliminating the CML in the system. The invention adopts LC-ESI-MS/MS to identify the addition product of quinones and CML. The result proves that quinone substances formed by oxidation of polyphenol containing catechol or pyrogallol structure have the capturing effect on CML in simulated food systems.
Compared with the prior art, the invention has the following beneficial effects:
(1) the polyphenol containing catechol or pyrogallol structure is a natural substance without toxic and side effects, wherein epicatechin, epicatechin gallate, epigallocatechin gallate and epigallocatechin are the main components of additive tea polyphenol allowed to be used in national standard GB2760-2014 of the people's republic of China; caffeic acid, one of the major components of grape seed extract, is recognized by the FDA as a generally recognized as a safe additive (GRAS); rutin and quercetin as the major components of citrus extract, 4-methylcatechol as the major component of castoreum extract, are also recognized by the FDA as generally recognized as safe additives (GRAS); the quinone substances formed by the oxidation of the substances have good elimination effect on AGEs generated in the system, and the defect that AGEs inhibitors have no effect on AGEs existing in the system is overcome.
(2) The quinone substance has stronger elimination capability to AGEs in a food system with neutral or alkaline pH.
(3) The quinone substances can be added after the CML is generated in a food system (see example 1) or added when the CML is not generated (see examples 2-4) to effectively reduce the CML level of the system.
Drawings
FIG. 1 is a diagram of possible pathways for inhibitors to inhibit CML formation.
FIG. 2 is a scheme showing the reaction of quinones with CML.
FIG. 3 shows a) a primary mass spectrum, b) a secondary mass spectrum and possible structures and fragmentation patterns of the adduct of 4-methylphthaloquinone (4MBQ) and CML.
FIG. 4 shows a) a primary mass spectrum and b) a secondary mass spectrum of an addition product of EC quinones and CML (heated at 80 ℃ for 1 h).
FIG. 5 shows a possible molecular structure and cleavage pattern of the adduct shown in FIG. 4.
FIG. 6 shows a) a primary mass spectrum, b) a secondary mass spectrum, and possible structures and cleavage patterns of an addition of EC quinones and CML (heated at 100 ℃ for 1 h).
FIG. 7 shows a) a primary mass spectrum and b) a secondary mass spectrum of an EGCG quinone and CML adduct (heated at 80 ℃ for 1 h).
FIG. 8 shows a possible molecular structure and cleavage pattern of the adduct shown in FIG. 7.
Detailed Description
The following detailed description is given with reference to specific embodiments.
Example 1
The identification of the CML capturing ability and the addition product structure of the 4-methylphthaloquinone (4MBQ) specifically comprises the following steps:
(1) 4MBQ solution was prepared to a concentration of 0.08mM using 0.2M phosphate buffer (pH 4.5);
(2) preparing a solution with a CML of 1-10mM with 0.2M phosphate buffer solution, mixing with the solution (1) in equal volume, and then adjusting the pH to 5.0, 7.0 or 8.0;
(3) determining the reaction kinetics of the 4MBQ and the CML by monitoring the absorbance change of the reaction system in an ultraviolet-visible light region (200-;
(4) a solution with a CML of 10mM and a 4MBQ of 1mM was prepared using 0.2M phosphate buffer (pH 7.0);
(5) stirring the mixed liquid in the step (4) for 1min at room temperature, and treating by a 0.22 mu m microfiltration membrane to prepare a liquid to be detected;
and finally, detecting the prepared sample to be detected by using LC-ESI-MS/MS under the following detection conditions.
The model of the LC is HP 1100, and the detection conditions are as follows:
a chromatographic column: ZIC-HILIC chromatographic column of 2.1 × 150mm, 3.5 μm
Column temperature: 25 deg.C
Mobile phase: a: ammonium acetate in water (6.5 mM)/acetonitrile (10:90, pH 5.5); b: ammonium acetate in water (6.5 mM)/acetonitrile (40:60, pH 5.5); gradient elution
Flow rate: 0.1mL/min
Sample introduction amount: 10 mu L of the solution;
the ESI-MS/MS model is HP 1100, and the detection conditions are as follows:
an ion source: ESI+
Drying gas temperature: 200 deg.C
Atomization air pressure: 50psi
Secondary fragmentation voltage: 1.00V
Scanning range: m/z is 50-750.
Apparent kinetic constants (k) for the CML capture effect of 4MBQ were obtained using the above-described Stopped-flowobs) And second order kinetic constant (k)2) As shown in Table 1, it was found that the CML trapping ability of 4MBQ was strong in the system at pH7 or more. When CML was 5mM and 4MBQ was 1mM, pH 8.0, 4MBQ captured 36% of the CML in the system in 5 minutes at 25 deg.C, pH7.4MBQ at 0, 25 ℃ can capture 14% of CML in the system within 5 minutes.
TABLE 1 apparent kinetic constants (k) for the reaction of 4MBQ with CML at 25 deg.C, pH 5, 7, 8obs) Second order kinetic constant (k)2)
The LC-ESI-MS/MS is used to detect the liquid to be detected under the above detection conditions to obtain a primary mass spectrum (fig. 3a) and a secondary mass spectrum (fig. 3b) of the captured product, so as to derive a structural diagram and a possible fragmentation pattern of the reaction product, as shown in fig. 3 b.
Example 2
The structure identification of the CML addition product captured by Epicatechin (EC) quinones specifically comprises the following steps:
(1) preparing 0.1M lysine (Lys) and 0.1M glucose (Glu) solutions with 0.2M phosphate buffer (pH 8.0) to simulate a food system;
(2) taking 1mL (1) of the simulated food system, and adding 2mM EC quinone;
(3) heating the sample in a water bath at 80 ℃ for 1 h;
(4) taking 1mL of heated sample, and adding distilled water to a constant volume of 5 mL;
(5) 1mL of the dilution was treated with a 0.22 μm microfiltration membrane and the adduct was structurally characterized using UPLC-ESI-MS/MS.
The UPLC adopts an Agilent SB1290 model, and the detection conditions are as follows:
a chromatographic column: agilent SB-C18Chromatographic column 2.1X 50mm, 1.8 μm
Column temperature: 25 deg.C
Mobile phase: A) formic acid: water-1: 1000(v: v), B) acetonitrile
Gradient elution procedure: 0min (85% A) -4min (15% A) -8min (15% A) -10min (85% A);
flow rate: 0.2mL/min
Sample introduction amount: 5 mu L of the solution;
the mass spectrum adopts a model as maxis Impact, and the detection conditions are as follows:
an ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Drying gas temperature: 180 deg.C
The pressure of the sprayer is as follows: 0.3bar
Mass to charge ratio scan range: m/z50-1000
The sample is detected by using the UPLC-ESI-MS/MS under the detection conditions to obtain a primary mass spectrum (FIG. 4a) and a secondary mass spectrum (FIG. 4b) of the EC quinone and CML adduct, and the structure diagram and possible fragmentation mode of the reaction product can be deduced, as shown in FIG. 5. Indicating that the EC quinones reacted with CML to form new species, thereby eliminating CML.
Example 3
The structure identification of the CML addition product captured by Epicatechin (EC) quinones specifically comprises the following steps:
(1) preparing 0.1M lysine (Lys) and 0.1M glucose (Glu) solutions with 0.2M phosphate buffer (pH 8.0) to simulate a food system;
(2) taking 1mL (1) of the simulated food system, and adding 2mM EC quinone;
(3) heating the sample in a water bath at 100 ℃ for 1 h;
(4) taking 1mL of heated sample, and adding distilled water to a constant volume of 5 mL;
(5) 1mL of the dilution was treated with a 0.22 μm microfiltration membrane and the adduct was structurally characterized using UPLC-ESI-MS/MS.
The UPLC adopts an Agilent SB1290 model, and the detection conditions are as follows:
a chromatographic column: agilent SB-C18Chromatographic column 2.1X 50mm, 1.8 μm
Column temperature: 25 deg.C
Mobile phase: A) formic acid: water-1: 1000(v: v), B) acetonitrile
Gradient elution procedure: 0min (85% A) -4min (15% A) -8min (15% A) -10min (85% A);
flow rate: 0.2mL/min
Sample introduction amount: 5 mu L of the solution;
the mass spectrum adopts a model as maxis Impact, and the detection conditions are as follows:
an ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Drying gas temperature: 180 deg.C
The pressure of the sprayer is as follows: 0.3bar
Mass to charge ratio scan range: m/z50-1000
The sample is detected by using the UPLC-ESI-MS/MS under the detection conditions to obtain a primary mass spectrum (FIG. 6a) and a secondary mass spectrum (FIG. 6b) of the EC quinone and CML adduct, so that a structure diagram and a possible fragmentation mode of the reaction product can be deduced, as shown in FIG. 6 b.
Example 4
The structure identification of the CML addition product captured by epigallocatechin gallate (EGCG) quinones specifically comprises the following steps:
(1) A0.2M phosphate buffer (pH 8.0) was used to formulate a solution with 0.1M lysine (Lys) and 0.1M glucose (Glu) to simulate a food system;
(2) taking 1mL (1) of the simulated food system, and adding 3mM EGCG quinone;
(3) heating the sample in a water bath at 80 ℃ for 1 h;
(4) taking 1mL of heated sample, and adding distilled water to a constant volume of 5 mL;
(5) 1mL of the dilution was treated with a 0.22 μm microfiltration membrane and the adduct was structurally characterized using UPLC-ESI-MS/MS.
The UPLC adopts an Agilent SB1290 model, and the detection conditions are as follows:
a chromatographic column: agilent SB-C18Chromatographic column 2.1X 50mm, 1.8 μm
Column temperature: 25 deg.C
Mobile phase: A) formic acid: water-1: 1000(v: v), B) acetonitrile
Gradient elution procedure: 0min (85% A) -4min (15% A) -8min (15% A) -10min (85% A);
flow rate: 0.2mL/min
Sample introduction amount: 5 mu L of the solution;
the mass spectrum adopts a model as maxis Impact, and the detection conditions are as follows:
an ion source: ESI+/ESI-；
Capillary voltage: 3.5kV
Charging voltage: 2kV
Drying gas temperature: 180 deg.C
The pressure of the sprayer is as follows: 0.3bar
Mass to charge ratio scan range: m/z is 50-1000.
The sample is detected by using the UPLC-ESI-MS/MS under the detection conditions to obtain a primary mass spectrum (FIG. 7a) and a secondary mass spectrum (FIG. 7b) of the EGCG quinone and CML adduct, so that a structural diagram and a possible fragmentation mode of the reaction product can be deduced, as shown in FIG. 8.
Claims (7)
1. The application of a carboxymethyl lysine eliminator in reducing the content of carboxymethyl lysine in a food system is characterized in that the eliminator is 4-methylphthaloquinone, epicatechin quinone or epigallocatechin gallate quinone.
2. Use according to claim 1, wherein the elimination agent is added to a food system, the pH of the system being controlled to be at least 7.
3. Use according to claim 2, characterized in that the system has a pH of 8.
4. Use according to claim 2, wherein the reaction temperature of the system is from 25 to 100%oC。
5. The use according to claim 2 or 3 or 4, characterized in that the elimination agent is added in an amount of 2-3% of the lysine content of the system.
6. Use according to claim 2 or 3 or 4, wherein the elimination agent is added after the food system has not produced or has produced CML.
7. Use according to claim 2 or 3 or 4, wherein the food system comprises dairy products, foodstuffs and products thereof, condiments, meats and products thereof, canned products.
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| CN110208355B (en) * | 2019-05-16 | 2022-07-05 | 东莞理工学院 | Method for measuring interaction efficiency of quinone substances and carboxymethyl lysine in solution |
| CN110702770B (en) * | 2019-08-26 | 2022-05-03 | 东莞理工学院 | Method for identifying reaction product of 4-methylphthaloquinone and amino compound in solution |
| CN111000154B (en) * | 2019-12-30 | 2022-06-17 | 南京黄教授食品科技有限公司 | Method for reducing advanced glycosylation end products of roasted chicken during frying |
| CN113156036B (en) * | 2021-05-25 | 2022-08-05 | 浙江大学 | Method for analyzing proanthocyanidin structure by combining hydrophilic effect and reversed phase liquid chromatography |
| CN113925168A (en) * | 2021-10-28 | 2022-01-14 | 湖北工业大学 | Application of EGCG quinone as inhibitor for resisting AGEs (angiotensin-converting enzyme) release in gastrointestinal tract |
| CN114903070A (en) * | 2022-05-23 | 2022-08-16 | 湖北工业大学 | Low AGEs waffles with high sensory quality and preparation method thereof |
| CN114916571A (en) * | 2022-05-23 | 2022-08-19 | 湖北工业大学 | Application of EC quinone in improving toughness biscuit quality |
| CN114916572A (en) * | 2022-05-23 | 2022-08-19 | 湖北工业大学 | Low-AGEs EGCG quinone-cookie and preparation method thereof |
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