CN109085269A - The method of PQQ and Lys and Arg reflex action research - Google Patents
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Abstract
The method of PQQ and Lys and Arg reflex action research, are the first part of PQQ Yu advanced glycation end products AGEs inhibiting effect research, belong to bioassay technique field.Lys and Arg is the DNA Main Free Amino Acids for participating in glucose response.To understand fully its mechanism of action, the present invention has studied PQQ and Lys and Arg reflex action, optimizes UPLC chromatographic separation condition, avoids the damage using the salting liquid of high concentration to chromatographic column, and enantiomer is also separated.Standard curve, accuracy and the detection limit of PQQ concentration has been determined, PQQ reacts the measurement of free PQQ concentration with Arg, Lys, the structure of UPLC-MS identification PQQ and Lys or Arg reaction product, measurement mass spectral results have found new compound PQQ-Lys, PQQ-Arg, and it also found that a molecule PQQ can react simultaneously with a molecule L ys and a molecule Arg, obtain noval chemical compound PQQ-Lys-Arg, PQQ provides experimental basis by the formation with Lys and Arg response inhabitation AGEs, to inquire into the mechanism that PQQ inhibits AGEs to be formed.
Description
Technical field
PQQ(pyrrolo- quinoline purine quinone) with Lys(lysine) and Arg(arginine) reflex action research method, be PQQ with
The first part of advanced glycation end products AGEs inhibiting effect research, belongs to bioassay technique field.
Background technique
Advanced glycation end products (advanced glycation end products, AGEs) are that albumen is chronic non-
Enzyme glycation product.AGEs is generally existing in normal human, as the level for increasing plasma A GEs at age can also rise therewith
Height, it is the important biomolecule marker of body aging, and AGEs level generally increases in diabetic and the elderly's body.According to report
Road, the formation of AGEs are likely to occur in the forming process of Alzheimer's disease (AD) early stage patch.AGEs and cell surface
RAGE (AGEs receptor) is combined, and can cause response to oxidative stress, and triggering cascade of response of inflammation, is even formed atherosclerosis
Thrombus.The accumulation of internal AGEs causes multiple complications, therefore AGEs is the target spot for being worth research.
The formation of AGEs includes a series of complex reaction, first by the carbonyl group and protein dna free amino acid of sugar
(mainly lysine Lys and arginine Arg) amino covalence, which combines, forms Schiff (Schiffbase) alkali, and this schiff bases are unstable
It is fixed, it resets obtain more stable Amadori product (early stage glycation product) rapidly, Amadori product is using a series of slow
Slow rearrangement and dehydrogenation reaction, obtains AGEs(and sees reaction equation 1).AGEs can cause endothelial cell apoptosis and increase active chalcogen
(ROS) generation, leads to the change of mitochondrial function, and these factors and diabetes, atherosclerosis, tumour, aging and
The pathogenesis of degenerative disease is highly relevant.
1 AGEs of reaction equation forms reaction path
Therefore reach that prevent these diseases be extremely promising potential arrange by inhibiting the accumulation of AGEs in vivo
It applies.We assume that if can the AGEs shown in reaction equation 1 formed reaction the first step, in reduced sugar and protein dna free ammonia
When base acid (Lys or Arg) amino covalence combination forms schiff bases, competed using certain inhibitor and Lys Arg amino anti-
It answers, can prevent from forming Schiffbase alkali with reducing sugar reaction, finally be able to suppress the formation of AGEs.
More and more researches show that the food rich in polyphenol is formed with very strong protective effect to AGEs.And pyrrolo- quinoline
Purine quinone (PQQ) and these polyphenols have similar biotic factor, and the neurodegenerative disease caused by oxidative stress is recognized
Knowing has stronger protective effect in obstacle.
PQQ is a kind of oxidoreducing enzyme prothetic group, is distributed mainly among prokaryotes and Activities of Some Plants and mammal.
PQQ has stronger oxidation resistance, can improve in the neurodegenerative diseases such as aging because of oxidative damage and oxidative stress
Caused Cognitive；The accumulation that can inhibit amyloid protein has prospect in terms for the treatment of the nervous system disease.Separately
Outside, there is the oral PQQ of document report that can improve diabetes B glucose tolerance in mice recently to be damaged, can reduce diabetic mice not
With organ oxidized damage.
PQQ structure is special, has a variety of special chemical property, is easy to and many kinds of substance knots such as amino acid, neurotransmitter
It closes.Under study for action it was found that the conjugation quinone key in PQQ can be combined by the amino of amino acid and be converted into beneficial derivative
Object, to play the role of removing free radical.However, its mechanism of action is not fully understood.We once used HPLC method to grind
Reacting for the neurotransmitters such as PQQ and glycine, glutamic acid is studied carefully, using ion-pairing agent and certain density buffer salt solution conduct
Mobile phase separates PQQ with reaction product.Document report only finds that PQQ and a molecule amino acid generate oxazole class (oxazole)
Compound.Lys and Arg is the DNA Main Free Amino Acids for participating in glucose response, and can PQQ react with Lys and Arg, PQQ
Whether have the function of inhibiting AGEs, whether oxidation resistance is related with the formation of AGEs is inhibited；In order to further understand fully it
Mechanism of action, the present invention have studied PQQ and Lys and Arg reflex action, and mass spectral results find new compound PQQ-Lys,
PQQ-Arg and PQQ-Lys- Arg(reaction equation 2), experimental basis is provided to inquire into the mechanism that PQQ inhibits AGEs to be formed.
2 PQQ of reaction equation and arginine and lysine reaction equation.
Summary of the invention
The object of the present invention is to provide a kind of PQQ(pyrrolo- quinoline purine quinones) with Lys(lysine) and Arg(arginine) react
The method of behavioral study, Lys and Arg are the DNA Main Free Amino Acids for participating in glucose response.In order to further understand fully its work
With mechanism, the present invention has studied PQQ and Lys and Arg reflex action, and mass spectral results find new compound PQQ-Lys, PQQ-
Arg and QQ-Lys- Arg(reaction equation 2), experimental basis is provided to inquire into the mechanism that PQQ inhibits AGEs to be formed.
The present invention uses ACQUiTY UPLC BEH C18 column (2.1 × 100mm, 1.7 μm), and flowing is added to
Formic acid is separated PQQ with Lys with the reaction product of Arg with methanol system gradient elution.New using UPLC-MS discovery
Compound PQQ-Lys and PQQ-Arg, and also found that the PQQ of a molecule can be anti-simultaneously with the Arg of a molecule L ys and a molecule
It answers, obtains new compound PQQ-Lys- Arg, enantiomer is also separated.It avoids using the salting liquid of high concentration to chromatography
The damage of column.
Technical solution of the present invention: the method for PQQ and Lys and Arg reflex action research, step are as follows:
1. UPLC chromatographic separation condition
UPLC analysis condition, chromatographic column: ACQUiTY UPLC@BEH C18 column (2.1 × 100mm, 1.7 μm), flowing
Phase A:H2O+0.1% formic acid, B: methanol；2/98 B/A elutes 5min, 20min gradient elution to 60/40 B/A.PDA detects (light
Electric second level array pipe detector).It, can be preferable with reaction product by PQQ after 0.1% formic acid and gradient elution are added in mobile phase
Separation.
2. standard curve, accuracy and detection limit measurement
Accurately weigh a certain amount of PQQ, be configured to concentration be 0.2,0.4,0.6,0.8,1.0 mM standard solution, respectively into
Sample, gained integral area map to sample concentration, carry out linear regression, and obtaining regression equation is y=6E+06x-7834.9, R2 =
0.9998；0.2 ~ 1.0mM of the range of linearity；As shown in Figure 1.
Under above-mentioned chromatographic condition continuous sample introduction 6 times on the same day, according in a few days relative standard obtained by calculated by peak area
Deviation is 2.2% (n=6), every other day continuous three days sample introductions, and standard deviation is 4.3% (n=3) in the daytime.Minimum detectable activity is 2.0ng(S/
N >=3)；
The measurement of 3.PQQ free PQQ concentration after being reacted with Arg, Lys
It is 1/1 hybrid reaction that PQQ is pressed with Arg, Lys to v/v respectively, separately mixes PQQ for 1/1/1 by v/v/v with Arg and Lys
Reaction, is protected from light, and is placed in 37 DEG C of water-baths and is incubated for, in 0,0.5,1,2,4,6,8,10 μ L, UPLC point of abstraction reaction liquid of each time point for 24 hours
Analysis, gained peak area substitute into linear equation, calculate the concentration of free PQQ.Gained PQQ concentration vs. time mapping, obtain PQQ with
The curve graph (Fig. 2) in reaction time.PQQ and Lys reaction speed are faster than PQQ and Arg as seen from the figure, and rear PQQ is reacted with Lys for 24 hours
Completely.PQQ and Arg reaction speed are lower than PQQ and Lys, react after 8h and tend towards stability substantially, PQQ fails to react completely.Work as Arg
In the case where existing simultaneously with Lys, PQQ reacts rapidly completely.
4. the structure of UPLC-MS identification PQQ and Lys or Arg reaction product
UPLC chromatographic condition is same as above, mass detector SQ Detector 2 and PDA detector, optimizes mass spectrometry parameters: desolventizing gas
Temperature: 400 DEG C；Desolventizing gas flow: 600 L/h；Ion source temperature: 110 DEG C；Taper hole throughput: 50L/h；Capillary voltage:
3000 V；Orifice potential: 30V；Mass spectrum uses electron spray positive ion mode ESI+.
In the ESI-MS spectrogram (Fig. 3) of PQQ and Arg reaction solution, it is that molecular weight is that obtained ion, which is m/z 441.32,
The M+1 molecular ion peak of 440 PQQ-Arg.Exist simultaneously the peak 331, PQQ M+1.Chromatogram in addition to 440 PQQ-Arg product
(retention time 1.55min, 2.23min, respectively enantiomer, there are also the PQQ chromatographic peak (retention times of molecular weight 330 outside peak
3.29min).
In the ESI-MS spectrogram (Fig. 4) of PQQ and Lys reaction solution, obtained ion is m/z 413.27 (M+1), 414.20
It (M+2), is the molecular ion peak for the PQQ-Lys that molecular weight is 412.Chromatogram shows product, and there are enantiomer (retention times
1.75min and 2.72min).
When PQQ and Arg and Lys are existed simultaneously, the PQQ of a molecule is tied with the Lys of the Arg of a molecule and a molecule respectively
It closes, in the ESI-MS spectrogram (Fig. 5) of reaction solution, obtained ion is m/z 525.32 (M+1), and 526.69 (M+2), are molecules
The molecular ion peak for the PQQ-Arg-Lys that amount is 524.Chromatogram show there are enantiomer (retention time be 2.22min and
2.76min).
Beneficial effects of the present invention: the present invention provides a kind of PQQ(pyrrolo- quinoline purine quinone) and Lys(lysine) and Arg(essence
Propylhomoserin) reflex action research method, Lys and Arg are the DNA Main Free Amino Acids for participating in glucose response.In order into one
Step understands fully its mechanism of action, and the present invention has studied PQQ and Lys and Arg reflex action, and mass spectral results find new compound
PQQ-Lys, PQQ-Arg and QQ-Lys- Arg(reaction equation 2), reality is provided to inquire into the mechanism that PQQ inhibits AGEs to be formed
Test foundation.
The present invention uses ACQUiTY UPLC BEH C18 column (2.1 × 100mm, 1.7 μm), and flowing is added to
Formic acid is separated PQQ with Lys with the reaction product of Arg with methanol system gradient elution.New using UPLC-MS discovery
Compound PQQ-Lys and PQQ-Arg, and also found that the PQQ of a molecule simultaneously can be same with the Arg of a molecule L ys and a molecule
Shi Fanying, obtains new compound PQQ-Lys- Arg, and enantiomer is also separated.Avoid the salting liquid pair using high concentration
The damage of chromatographic column.
Detailed description of the invention
Fig. 1 integral area is to PQQ concentration standard curve.
Curve graph of Fig. 2 PQQ concentration to the reaction time.
Fig. 3 PQQ and Arg reaction product chromatography, mass spectrogram.
Fig. 4 PQQ and Lys reaction product chromatography, mass spectrogram.
Fig. 5 PQQ and Arg Lys reaction product chromatography, mass spectrogram.
Specific embodiment
Embodiment 1
1. UPLC chromatographic separation condition
UPLC analysis condition, chromatographic column: ACQUiTY UPLC@BEH C18 column (2.1 × 100mm, 1.7 μm), flowing
Phase A:H2O+0.1% formic acid, B: methanol；2/98 B/A elutes 5min, 20min gradient elution to 60/40 B/A.PDA detection.Stream
After 0.1% formic acid and gradient elution is added in dynamic phase, PQQ can preferably be separated with reaction product.
2. standard curve, accuracy and detection limit measurement
Accurately weigh a certain amount of PQQ, be configured to concentration be 0.2,0.4,0.6,0.8,1.0 mM standard solution, respectively into
Sample, gained integral area map to sample concentration, carry out linear regression, and obtaining regression equation is y=6E+06x-7834.9, R2 =
0.9998；0.2 ~ 1.0mM of the range of linearity；As shown in Figure 1.
Under above-mentioned chromatographic condition continuous sample introduction 6 times on the same day, according in a few days relative standard obtained by calculated by peak area
Deviation is 2.2% (n=6), every other day continuous three days sample introductions, and standard deviation is 4.3% (n=3) in the daytime.Minimum detectable activity is 2.0ng(S/
N >=3)；
The measurement of PQQ concentration 3. PQQ dissociates after reacting with Arg, Lys
It is 1/1 hybrid reaction that PQQ is pressed with Arg, Lys to v/v respectively, and PQQ is mixed instead by v/v/v for 1/1/1 with Arg and Lys
It answers, is protected from light, be placed in 37 DEG C of water-baths and be incubated for, in 0,0.5,1,2,4,6,8,10 μ L, UPLC point of abstraction reaction liquid of each time point for 24 hours
Analysis, gained peak area substitute into linear equation, calculate the concentration of free PQQ.Gained PQQ concentration vs. time mapping, obtain PQQ with
The curve graph (Fig. 2) in reaction time.PQQ and Lys reaction speed are faster than Arg as seen from the figure, for 24 hours rear PQQ and Lys fully reacting.
PQQ and Arg reaction speed are lower than Lys, react after 8h and tend towards stability substantially, PQQ fails to react completely.When Arg and Lys is deposited simultaneously
In case, PQQ reacts rapidly completely.
4. the structure of UPLC-MS identification PQQ and Lys or Arg reaction product
UPLC chromatographic condition is same as above, mass detector SQ Detector 2 and PDA detector, optimizes mass spectrometry parameters: desolventizing gas
Temperature: 400 DEG C；Desolventizing gas flow: 600 L/h；Ion source temperature: 110 DEG C；Taper hole throughput: 50L/h；Capillary voltage:
3000 V；Orifice potential: 30V；Mass spectrum uses electron spray positive ion mode ESI+.
In the ESI-MS spectrogram (Fig. 3) of PQQ and Arg reaction solution, it is that molecular weight is that obtained ion, which is m/z 441.32,
The M+1 molecular ion peak of 440 PQQ-Arg.Exist simultaneously the peak 331, PQQ M+1.Chromatogram in addition to 440 PQQ-Arg product
(retention time 1.55min, 2.23min, respectively enantiomer, there are also the PQQ chromatographic peak (retention times of molecular weight 330 outside peak
3.29min).
In the ESI-MS spectrogram (Fig. 4) of PQQ and Lys reaction solution, obtained ion is m/z 413.27 (M+1), 414.20
It (M+2), is the molecular ion peak for the PQQ-Lys that molecular weight is 412.Chromatogram shows product, and there are enantiomer (retention times
Tr1.75min, 2.72min).
When PQQ and Arg and Lys are existed simultaneously, the PQQ of a molecule is tied with the Lys of the Arg of a molecule and a molecule respectively
It closes, in the ESI-MS spectrogram (Fig. 5) of reaction solution, obtained ion is m/z 525.32 (M+1), and 526.69 (M+2), are molecules
The molecular ion peak for the PQQ-Arg-Lys that amount is 524.Chromatogram show there are enantiomer (retention time be 2.22min and
2.76min).
Claims (1)
- The method of 1.PQQ and Lys and Arg reflex action research, it is characterised in that step are as follows:(1) UPLC chromatographic separation conditionUPLC analysis condition, chromatographic column: ACQUiTY UPLC@BEH C18 column (2.1 × 100mm, 1.7 μm), flowing Phase A:H2O+0.1% formic acid, B: methanol；2/98 B/A elutes 5min, 20min gradient elution to 60/40 B/A；PDA detection；Stream After 0.1% formic acid and gradient elution is added in dynamic phase, PQQ can preferably be separated with reaction product；(2) standard curve, accuracy and detection limit measurementAccurately weigh a certain amount of PQQ, be configured to concentration be 0.2,0.4,0.6,0.8,1.0 mM standard solution, respectively into Sample, gained integral area map to sample concentration, carry out linear regression, and obtaining regression equation is y=6E+06x-7834.9, R2 = 0.9998；0.2 ~ 1.0mM of the range of linearity；Under above-mentioned chromatographic condition continuous sample introduction 6 times on the same day, according in a few days relative standard deviation obtained by calculated by peak area For 2.2%, n=6；Continuous three days sample introductions every other day, standard deviation is 4.3%, n=3 in the daytime；Minimum detectable activity is 2.0ng, S/N >=3；(3) measurement for PQQ concentration of dissociating after PQQ is reacted with Arg, LysIt is 1/1 hybrid reaction that PQQ is pressed with Arg, Lys to v/v respectively, separately mixes PQQ for 1/1/1 by v/v/v with Arg and Lys Reaction, is protected from light, and is placed in 37 DEG C of water-baths and is incubated for, in 0,0.5,1,2,4,6,8,10 μ L, UPLC point of abstraction reaction liquid of each time point for 24 hours Analysis, gained peak area substitute into linear equation, calculate the concentration of free PQQ；The mapping of gained PQQ concentration vs. time, obtains PQQ- Reaction time curve graph is faster than PQQ and Arg by the visible PQQ of PQQ- reaction time curve graph and Lys reaction speed, for 24 hours rear PQQ With Lys fully reacting；PQQ and Arg reaction speed are lower than PQQ and Lys, react after 8h and tend towards stability substantially, and PQQ fails completely anti- It answers；In the case that Arg and Lys are existed simultaneously, PQQ reacts rapidly completely；(4) UPLC-MS identifies the structure of PQQ and Lys or Arg reaction productUPLC chromatographic condition is same as above, mass detector SQ Detector 2 and PDA detector, optimizes mass spectrometry parameters: desolventizing gas Temperature: 400 DEG C；Desolventizing gas flow: 600 L/h；Ion source temperature: 110 DEG C；Taper hole throughput: 50L/h；Capillary voltage: 3000 V；Orifice potential: 30V；Mass spectrum uses electron spray positive ion mode ESI+；In the ESI-MS spectrogram of PQQ and Arg reaction solution, obtained ion is m/z 441.32, is the PQQ- that molecular weight is 440 The M+1 molecular ion peak of Arg；Exist simultaneously the peak 331, PQQ M+1；There is the PQQ-Arg product peak of molecular weight 440 in chromatogram, Retention time 1.55min, 2.23min, there are also the PQQ chromatographic peak of enantiomer molecular weight 330, retention time 3.29min；In the ESI-MS spectrogram of PQQ and Lys reaction solution, obtained ion is m/z 413.27 (M+1), and 414.20 (M+2), are point The molecular ion peak for the PQQ-Lys that son amount is 412；Chromatogram show product there are enantiomers: retention time be 1.75min and 2.72min；When PQQ and Arg and Lys are existed simultaneously, the PQQ of a molecule respectively in conjunction with the Lys of the Arg of a molecule and a molecule, In the ESI-MS spectrogram of reaction solution, obtained ion is m/z 525.32 (M+1), and it is 524 that 526.69 (M+2), which are molecular weight, The molecular ion peak of PQQ-Arg-Lys, chromatogram show that, there are enantiomer, retention time is 2.22min and 2.76min.
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| CN112461975A (en) * | 2020-09-11 | 2021-03-09 | 福建省产品质量检验研究院 | Method for detecting coenzyme content in feed additive |
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