CN110317796B - Application of 4-sulfonated calix [ n ] arene/CTAB complex ligand system in improving activity of polyphenol oxidase - Google Patents
Application of 4-sulfonated calix [ n ] arene/CTAB complex ligand system in improving activity of polyphenol oxidase Download PDFInfo
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Abstract
The invention discloses an application of a 4-sulfonated calix [ n ] arene/CTAB complex ligand system in improving the activity of polyphenol oxidase in pineapples. The invention compounds 4-sulfonated calix [ n ] arene for inhibiting the enzymatic activity and a surfactant CTAB for improving the enzymatic activity to form a super amphiphilic molecule which interacts with polyphenol oxidase in pineapple extract. According to the invention, the regulation and control of the activity of polyphenol oxidase in the pineapple are realized for the first time through a 4-sulfonated calix [ n ] arene/CTAB compound system, the 4-sulfonated calix [ n ] arene/CTAB compound is adopted, the inhibition effect of the 4-sulfonated calix [ n ] arene on the activity of polyphenol oxidase in the pineapple is reduced, and the activity of the polyphenol oxidase in the pineapple can be obviously improved to 419% under the optimal condition.
Description
Technical Field
The invention belongs to the technical field of biological enzymes, and relates to an application of a 4-sulfonated calix [ n ] arene/hexadecyl trimethyl ammonium bromide complex ligand system in improving polyphenol oxidase activity, in particular to an application of the 4-sulfonated calix [ n ] arene/hexadecyl trimethyl ammonium bromide complex ligand system in improving polyphenol oxidase activity in pineapples.
Background
Many different kinds of proteases are present in many plants, and among them, polyphenol oxidase (PPO) is a metalloprotease which is extremely widely distributed in nature and is widely present in plants such as apple, pineapple, mushroom, etc. It is widely applied in many fields such as food, chemical industry, medicine and the like, but because some additives are often used in the application process, the enzymatic activity of polyphenol oxidase is reduced and even inactivated. How to maintain the activity of polyphenol oxidase in the presence of additives is a problem to be solved in the industrial application process.
Calixarene has similar properties to cyclodextrin and crown ether, is known as third-generation supramolecules, can interact with biomolecules, and has wide application in protein recognition and protein assembly. Chinese patent application 201810041508.4 discloses the use of calixarene derivatives in the regulation of bromelain and polyphenol oxidase activities. Wherein the 4-sulfonated calix [ n ] arene plays a role in inhibiting the activity of polyphenol oxidase in the pineapple juice.
Cetyl Trimethyl Ammonium Bromide (CTAB) belongs to a cationic surfactant, has good surface activity, stability, bactericidal property and biodegradability, is heat-resistant and light-resistant, and is widely used in the aspects of wetting, sterilization, antistatic, decontamination, solubilization and the like. Chinese patent application 201610175997.3 reports that CTAB can improve polyphenol oxidase activity in crude extract of fructus Mali Pumilae, and when CTAB concentration is 0.3mM and pH is 7, polyphenol oxidase activity can be improved by about 75%.
Disclosure of Invention
The invention aims to provide an application of a 4-sulfonated calix [ n ] arene (SC [ n ])/CTAB complex system in improving the activity of polyphenol oxidase in pineapples. The invention compounds SC [ n ] and CTAB to form super amphiphilic molecule, which reduces the inhibition of SC [ n ] to the activity of polyphenol oxidase in pineapple. In the presence of SC [ n ], CTAB is added to raise the activity of polyphenol oxidase in pineapple greatly.
In the invention, the structural formula of the 4-sulfonated calix [ n ] arene is shown as a formula I:
In the invention, in the SC [ n ]/CTAB compound system, the pH is adjusted to the optimum pH of polyphenol oxidase in pineapple, namely the pH = 6.0-8.0.
In the invention, in the SC [ n ]/CTAB compound system, the temperature is adjusted to the optimum temperature of polyphenol oxidase in pineapple, namely the temperature is 25-45 ℃.
In the SC [ n ]/CTAB compound system, the mass ratio of SC [ n ] to CTAB is (1).
In the concrete embodiment of the invention, in the SC [ n ]/CTAB compound system, the mass ratio of SC [4] to CTAB is 1 to 5.
In the embodiment of the invention, in the SC [ n ]/CTAB compound system, the mass ratio of SC [6] to CTAB is 1.
In the embodiment of the invention, in the SC [ n ]/CTAB compound system, the mass ratio of SC [8] to CTAB is 1.
Compared with the prior art, the invention has the following advantages:
SC n has inhibitory action on the activity of polyphenol oxidase in pineapple juice, but cannot improve the activity of polyphenol oxidase, wherein the inhibitory rate of SC 4, SC 6 or SC 8 on the activity of polyphenol oxidase is close to 100% (Chinese patent application 201810041508.4). CTAB can improve the activity of polyphenol oxidase in the crude extract of fructus Mali Pumilae by about 75% at most (Chinese patent application 201610175997.3). The invention compounds 4-sulfonated calix [ n ] arene for inhibiting the enzyme activity and a surfactant CTAB for improving the enzyme activity to form a super amphiphilic molecule which interacts with polyphenol oxidase. The invention realizes the regulation and control of the activity of polyphenol oxidase in pineapple by SC [ n ]/CTAB complex system for the first time, and the SC [ n ]/CTAB complex reduces the inhibition of SC [ n ] to the activity of polyphenol oxidase in pineapple, and can obviously improve the activity of polyphenol oxidase in pineapple to 419% under the optimum condition.
Drawings
FIG. 1 is a diagram showing the effect of the SC 4/CTAB complex system on the activity of polyphenol oxidase in crude pineapple extractive solution (reaction temperature t =30 ℃, pH = 7).
FIG. 2 is a diagram showing the effect of the SC 6/CTAB complex system on the activity of polyphenol oxidase in the crude pineapple extract (reaction temperature t =30 ℃, pH = 7).
FIG. 3 is a graph showing the effect of the SC 8/CTAB complex system on the activity of polyphenol oxidase in the crude pineapple extract (reaction temperature t =30 ℃, pH = 7).
FIG. 4 is a graph showing the effect of the SC [8]/CTAB complex system on the activity of polyphenol oxidase in crude apple extract (reaction temperature t =30 ℃ C., pH = 7).
Fig. 5 is a graph showing the effect of SC [8] and CTAB concentrations on polyphenol oxidase activity in crude pineapple extract (reaction temperature t =30 ℃, pH = 7).
Detailed Description
The present invention will be described in more detail with reference to examples.
In the following examples, the pH of the phosphate buffered solution used in the pineapple and apple systems was 7.0, the reaction temperature was 30 ℃, the substrate was catechol, and the concentration of SC [ n ] was in the range of [ SC [4] ] =0-0.1mg/mL, [ SC [6] ] =0-0.1mg/mL, [ SC [8] ] =0-0.2mg/mL, respectively.
(1) Preparation of crude enzyme solution
Coarse pineapple extract: peeling pineapple, cutting into pieces, weighing 24.3158g, adding 24mL phosphate buffer solution (40mM, pH 6.0) containing disodium ethylene diamine tetraacetic acid (EDTA & 2 Na), juicing with a juicer for 3-5 minutes, filtering with gauze, centrifuging the filtrate in a high-speed refrigerated centrifuge with the rotation speed of 10000rpm and the temperature of 4 ℃ for 25 minutes, and storing the separated supernatant at-20 ℃.
Coarse apple extract: cleaning fructus Mali Pumilae in clear water, draining, and freezing at-20 deg.C for 12 hr. Cutting frozen apples into 58.82g, adding 100mL of phosphoric acid buffer solution (0.2M pH =6.5, containing 0.25% (v/v) TritonX-100 and 2% (w/w) polyvinylpyrrolidone), mixing and pulping for 1min, then filtering with gauze, centrifuging the filtrate in a high-speed refrigerated centrifuge with the rotation speed of 10000rpm and the temperature of 4 ℃ for 10min, and placing the separated supernatant at-20 ℃ for storage.
(2) Preparation of substrate solution
Catechol:
a300 mM catechol solution was prepared in pH 7.0 100mM phosphate buffer solution.
(3) Preparation of surfactant mother liquor
A2 mg/mLCTAB solution was prepared in water.
(4) Preparation of calixarene mother liquor
A4 mg/mLSCn solution is prepared in water.
(5) Enzyme activity assay (ultraviolet spectrophotometer)
Polyphenol oxidase
And (3) testing the enzymatic activity of polyphenol oxidase in the crude pineapple extract by using catechol as a substrate. In the test system, the catechol concentration was 150mM and the test wavelength was 420nm. The absorbance value (A) at 420nm is plotted against time (t) and by calculating the slope of the linear portion of the plot, the molar absorption coefficient (1100M) of the product o-phenylenediquinone is combined -1 cm -1 ) Obtaining the initial reaction rate v (mu M s) of catalytic oxidation of catechol by polyphenol oxidase -1 ). The enzyme activity without any additives was defined as 100%.
Example 1
The influence of SC 4/CTAB compound system on the activity of polyphenol oxidase in the pineapple crude extract is as follows:
the experiments were divided into two groups: group 1A defined amount of SC [4]]Mixing mother liquor and crude extract of pineapple, and mixing group 2 with a certain amount of CTAB mother liquor and SC 4]Mixing the mother solution and the crude pineapple extractive solution, and balancing at 30 deg.C for 1 hr. Adding the obtained mixed solution into catechol solution for catalytic reaction, and detecting the change of the absorbance value with time at 420nm of the reaction solution after the reaction is finished. In the reaction system, SC [4] in group 1]The concentrations of (A) are 0,0.02mg/mL,0.06mg/mL,0.08mg/mL,0.1mg/mL, respectively, and the catechol concentration is 150mM. Group 2, CTAB concentration 0.1mg/mL, SC [4]]The concentrations of (A) are 0,0.02mg/mL,0.06mg/mL,0.08mg/mL,0.1mg/mL, respectively, and the catechol concentration is 150mM. The absorbance value (A) at 420nm is plotted against time (t) and by calculating the slope of the linear portion of the plot, the molar absorption coefficient (1100M) of the product o-phenylenediquinone is combined -1 cm -1 ) Obtaining the initial reaction rate v (mu M.s) of catalytic oxidation of catechol by the polyphenol oxidase -1 ). The enzyme activity without any additives is defined as 100%.
Example 2
The influence of SC 6/CTAB compound system on the activity of polyphenol oxidase in the pineapple crude extract is as follows:
the experiments were divided into two groups: group 1 amount of SC 6]Mixing mother liquor with crude extract of fructus Ananadis Comosi, and mixing with group 2 certain amount of CTAB mother liquor and SC [6]]Mixing the mother liquor and the crude extract of pineapple, and balancing at 30 deg.C for 1 hr. Adding the obtained mixed solution into catechol solution for catalytic reaction, and detecting the change of the absorbance value with time at 420nm of the reaction solution after the reaction is finished. In the reaction overall system, group 1, SC [6]]The concentrations of (A) are 0,0.02mg/mL,0.06mg/mL,0.08mg/mL,0.1mg/mL, respectively, and the catechol concentration is 150mM. Group 2, CTAB concentration 0.1mg/mL, SC [6]]The concentrations of (A) are 0,0.02mg/mL,0.06mg/mL,0.08mg/mL,0.1mg/mL, respectively, and the catechol concentration is 150mM. The absorbance value (A) at 420nm is plotted against time (t) by calculating the slope of the linear part of the plotRate, molar absorptivity of the bound product o-phenylenediquinone (1100M) -1 cm -1 ) Obtaining the initial reaction rate v (mu M s) of catalytic oxidation of catechol by polyphenol oxidase -1 ). The enzyme activity without any additives was defined as 100%.
Example 3
The influence of SC 8/CTAB compound system on the activity of polyphenol oxidase in the pineapple crude extract is as follows:
the experiments were divided into two groups: group 1 amount of SC [8]]Mixing mother liquor and crude extract of pineapple, and mixing group 2 with a certain amount of CTAB mother liquor and SC [8]]Mixing the mother solution and crude extract of pineapple, and balancing at 30 deg.C for 1 hr. Adding the obtained mixed solution into catechol solution for catalytic reaction, and detecting the change of the absorbance value with time at 420nm of the reaction solution after the reaction is finished. In the reaction overall system, SC [8] in group 1]The concentrations of (A) are 0,0.02mg/mL,0.1mg/mL,0.2mg/mL, respectively, and the catechol concentration is 150mM. Group 2CTAB concentration of 0.1mg/mL, SC [8]The concentrations are 0,0.02mg/mL,0.1mg/mL and 0.2mg/mL respectively, and the catechol concentration is 150mM. The absorbance value (A) at 420nm was plotted against time (t), and by calculating the slope of the linear portion of the plot, the molar absorption coefficient (1100M) of the product o-diphenoquinone was combined -1 cm -1 ) Obtaining the initial reaction rate v (mu M s) of catalytic oxidation of catechol by polyphenol oxidase -1 ). The enzyme activity without any additives is defined as 100%.
Example 4
The influence of SC 8/CTAB compound system on the activity of polyphenol oxidase in the apple crude extract is as follows:
the experiments were divided into two groups: group 1 amount of SC [8]]Mixing the mother liquid with the crude extractive solution of fructus Mali Pumilae, and mixing with group 2 a certain amount of CTAB mother liquid, SC [8]]Mixing the mother liquor and the crude extractive solution of fructus Mali Pumilae, and balancing at 30 deg.C for 1 hr. Adding the obtained mixed solution into catechol solution for catalytic reaction, and detecting the change of the absorbance value with time at 420nm of the reaction solution after the reaction is finished. In the total reaction system, the enzyme was diluted 25-fold. In group 1, SC [8]The concentrations of (A) are 0,0.02mg/mL,0.1mg/mL,0.2mg/mL, respectively, and the catechol concentration is 150mM. Group 2, CTAB concentration 0.1mg/mL, SC [8]]The concentrations of (A) are respectively 0,0.02mg/mL and 0.1mg/mL,0.2mg/mL, catechol concentration of 150mM. The absorbance value (A) at 420nm is plotted against time (t) and by calculating the slope of the linear portion of the plot, the molar absorption coefficient (1100M) of the product o-phenylenediquinone is combined -1 cm -1 ) Obtaining the initial reaction rate v (mu M s) of catalytic oxidation of catechol by polyphenol oxidase -1 ). The enzyme activity without any additives was defined as 100%.
Example 5
The influence of SC 8 and CTAB concentration ratio on the activity of polyphenol oxidase in crude pineapple extract:
the experiments were divided into four groups, in each of which a certain amount of SC [8] was added]Mixing the mother liquor, CTAB mother liquor and crude extract of pineapple. In group 1, SC [8]The concentration is 0.1mg/mL, the CTAB concentration is 0.05mg/mL, and the catechol concentration is 150mM. In group 2, SC [8]]The concentration is 0.1mg/mL, the CTAB concentration is 0.1mg/mL, and the catechol concentration is 150mM. In group 3, SC [8]]The concentration is 0.1mg/mL, the CTAB concentration is 0.15mg/mL, and the catechol concentration is 150mM. In group 4, SC [8]]The concentration is 0.1mg/mL, the CTAB concentration is 0.20mg/mL, and the catechol concentration is 150mM. The absorbance value (A) at 420nm is plotted against time (t) and by calculating the slope of the linear portion of the plot, the molar absorption coefficient (1100M) of the product o-phenylenediquinone is combined -1 cm -1 ) Obtaining the initial reaction rate v (mu M s) of catalytic oxidation of catechol by polyphenol oxidase -1 ). The enzyme activity without any additives is defined as 100%.
For polyphenol oxidase existing in the pineapple/apple crude extract, calixarene with different charges and different cavity sizes is added, and the influence degree on the enzyme activity is as follows:
(1) Polyphenol oxidase in the pineapple crude extract: when SC n is not compounded with CTAB, when the concentration of SC n is 0-0.1mg/mL, the enzyme activity is basically kept unchanged or reduced to 72% -64% (figure 1-3); for SC 8, when the concentration of SC 8 is 0.2mg/mL, the enzyme activity decreases to 22% (FIG. 3); when SC n is compounded with 0.1mg/mL CTAB, the enzyme activity is increased to 122% -152% when the concentration of SC 4 is 0.02-0.06 mg/mL, but the enzyme activity is decreased to 70% -84% when the concentration of SC 4 is increased to 0.08-0.1 mg/mL (figure 1). When the concentration of SC 6 is 0.02mg/mL, the enzyme activity is increased to 124%, and when the concentration is increased to 0.08-0.1 mg/mL, the enzyme activity is decreased to 86% (FIG. 2). When the concentration of SC 8 is 0.02mg/mL, the enzyme activity is increased to 142%, and when the concentration is 0.1mg/mL, the enzyme activity is significantly increased to 419% (FIG. 3).
(2) Polyphenol oxidase in the apple crude extract: the polyphenol oxidase can raise the enzyme activity to 188% when it is combined with CTAB alone, and the raised enzyme activity is lowered to 104% when 0.02mg/mL SC 8 is added. When the concentration of SC 8 is 0.1 mg/mL-0.2 mg/mL, the enzyme activity is reduced to 8% (FIG. 4). Therefore, the calixarene/CTAB compound system cannot improve the activity of polyphenol oxidase in the apples.
(3) It can be found from the effect of CTAB with different concentrations on polyphenol oxidase activity in crude pineapple extract, and when the concentration ratio of CTAB to SC [8] is 1, the polyphenol oxidase activity is improved most effectively (FIG. 5).
Claims (5)
- The application of a 4-sulfonated calix [ n ] arene/CTAB complex ligand system in improving the activity of polyphenol oxidase in pineapples is characterized in that the structural formula of the 4-sulfonated calix [ n ] arene is shown as a formula I:，SC[n]n =8, said SC [ n ]]In a CTAB compound system, SC 8]Mass ratio to CTAB is 1.
- 2. The use according to claim 1, wherein the SC [ n ]/CTAB complex system is adjusted to the optimum pH of polyphenol oxidase in pineapple.
- 3. The use according to claim 1 or 2, wherein the SC [ n ]/CTAB compound system has a pH of 6.0 to 8.0.
- 4. The use according to claim 1, wherein the temperature of the SC [ n ]/CTAB complex system is adjusted to the optimum temperature of polyphenol oxidase in pineapple.
- 5. The use according to claim 1 or 4, wherein the temperature in the SC [ n ]/CTAB complex system is 25 ℃ to 45 ℃.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105734025A (en) * | 2016-03-25 | 2016-07-06 | 扬州大学 | Method for improving activity of polyphenol oxidase in apples by virtue of hexadecyl trimethyl ammonium bromide and dodecyl trimethyl ammonium bromide |
| WO2017092513A1 (en) * | 2015-11-30 | 2017-06-08 | 南京农业大学 | Angular dioxygenase gene dpea1a2 and use thereof |
| CN107099515A (en) * | 2017-06-21 | 2017-08-29 | 扬州大学 | A kind of apple polyphenol oxidase accelerative activator and its application |
| CN108559770A (en) * | 2018-01-16 | 2018-09-21 | 扬州大学 | Application of the Calixarene Derivatives in regulation and control bromelain and polyphenol oxidase activity |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017092513A1 (en) * | 2015-11-30 | 2017-06-08 | 南京农业大学 | Angular dioxygenase gene dpea1a2 and use thereof |
| CN105734025A (en) * | 2016-03-25 | 2016-07-06 | 扬州大学 | Method for improving activity of polyphenol oxidase in apples by virtue of hexadecyl trimethyl ammonium bromide and dodecyl trimethyl ammonium bromide |
| CN107099515A (en) * | 2017-06-21 | 2017-08-29 | 扬州大学 | A kind of apple polyphenol oxidase accelerative activator and its application |
| CN108559770A (en) * | 2018-01-16 | 2018-09-21 | 扬州大学 | Application of the Calixarene Derivatives in regulation and control bromelain and polyphenol oxidase activity |
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