CN115960076A - Alpha-lipoic acid-organic alkali ion salt and preparation method and application thereof - Google Patents
Alpha-lipoic acid-organic alkali ion salt and preparation method and application thereof Download PDFInfo
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- CN115960076A CN115960076A CN202211698524.3A CN202211698524A CN115960076A CN 115960076 A CN115960076 A CN 115960076A CN 202211698524 A CN202211698524 A CN 202211698524A CN 115960076 A CN115960076 A CN 115960076A
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Images
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The application provides an alpha-lipoic acid-organic base ion salt and a preparation method and application thereof, relating to the technical field of compound synthesis. The alpha-lipoic acid-organic base ionic salt is obtained by connecting alpha-lipoic acid and organic base through a chemical bond, so that the water solubility of the alpha-lipoic acid and the organic base is improved, the stability of the alpha-lipoic acid is improved, and the application of the alpha-lipoic acid-organic base ionic salt in an antioxidant product is improved. The preparation method of the alpha-lipoic acid-organic alkali ion salt is simple to operate, green and environment-friendly, uses water and ethanol solution as solvents, avoids the use of toxic organic solvents, and avoids the influence of high-temperature self-polymerization on the efficacy of the alpha-lipoic acid due to low-temperature reaction.
Description
Technical Field
The application relates to the technical field of compound synthesis, in particular to alpha-lipoic acid-organic base ion salt and a preparation method and application thereof.
Background
Alpha-lipoic acid is an endogenous antioxidant, can remove free radicals of an organism, can promote the organism to synthesize vitamin C by using glucose, can promote the organism to synthesize glutathione, can effectively remove melanin, and can assist coenzyme to carry out physiological metabolism favorable for the immunity of the organism. Alpha-lipoic acid also has anti-inflammatory effect, and can inhibit the activities of kinase, transforming factor, d-tumor necrosis factor and collagenase, and has anti-aging effect. Alpha-lipoic acid can preserve and regenerate other antioxidants, has good health-care effect on human bodies, and is widely applied to preventing and treating heart diseases, diabetes, liver diseases and senile dementia at present.
However, alpha-lipoic acid is very unstable, has a low melting point (47-50 ℃), can be polymerized at a low temperature, is insoluble in water and cannot be prepared into a liquid preparation, so the physicochemical property of the alpha-lipoic acid directly limits the application of the alpha-lipoic acid.
Disclosure of Invention
The application aims to provide an alpha-lipoic acid-organic alkali ion salt, a preparation method and an application thereof, and aims to solve the problems that alpha-lipoic acid is easy to polymerize, poor in thermal stability and insoluble in water.
To achieve the above objects, the present application provides an α -lipoic acid-organic base ion salt obtained by linking α -lipoic acid and an organic base through a chemical bond; the organic base has strong basicity, and a naked lone electron pair exists in an N atom in the organic base, so that the organic base is easy to accept protons.
Preferably, the compound is selected from any one of formula I to formula III:
the present application also provides a method for preparing an alpha-lipoic acid-organic base ion salt, comprising:
dissolving, mixing and reacting alpha-lipoic acid and organic base in an ethanol solution to obtain a reaction solution;
and (3) evaporating the reaction solution under vacuum to remove ethanol, and freeze-drying to remove water to obtain the alpha-lipoic acid-organic alkali ion salt.
Preferably, the organic base is selected from any one of arginine, matrine, synephrine.
Preferably, the molar ratio of the alpha-lipoic acid to the organic base is 1: (0.8-1.5).
Preferably, the molar ratio of the alpha-lipoic acid to the organic base is 1:1.
preferably, the ratio of the mass of the alpha-lipoic acid and the organic base to the volume of the ethanol solution is 1g: (1.5-10) ml;
preferably, the concentration of the ethanol solution is in the range of 30% -70%.
Preferably, ultrasonic waves are applied in the process of dissolving and mixing, and the frequency of the ultrasonic waves is 30-50KHz.
Preferably, the reaction temperature is 20-80 ℃ and the reaction time is 4-10h.
The application also provides application of the alpha-lipoic acid-organic alkali ion salt in preparation of cosmetics, health-care products and medicines.
Compared with the prior art, the beneficial effect of this application includes:
the alpha-lipoic acid-organic base ionic salt is obtained by connecting alpha-lipoic acid and organic base through a chemical bond, so that the water solubility of the alpha-lipoic acid and the organic base is improved, the stability of the alpha-lipoic acid is improved, and the application of the alpha-lipoic acid-organic base ionic salt in an antioxidant product is improved. The preparation method of the alpha-lipoic acid-organic alkali ion salt is simple to operate, green and environment-friendly, uses water and ethanol solution as solvents, avoids the use of toxic organic solvents, and avoids the influence of high-temperature self-polymerization on the efficacy of the alpha-lipoic acid due to low-temperature reaction.
Drawings
To more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are required to be used in the embodiments are briefly described below, and it should be understood that the following drawings only illustrate some embodiments of the present application and therefore should not be considered as limiting the scope of the present application.
Fig. 1 is a schematic flow diagram of a method for preparing an alpha-lipoic acid-organic base ion salt according to the present application;
fig. 2 is a graph showing the results of water solubility of α -lipoic acid-organic base ion salts of the present application;
FIG. 3A is a graph showing the DPPH radical scavenging results of alpha-lipoic acid-arginine obtained at different reaction temperatures;
fig. 3B is a DPPH radical scavenging result of α -lipoic acid-matrine obtained at different reaction temperatures;
FIG. 3C is a graph showing the DPPH radical scavenging results for alpha-lipoic acid-synephrine obtained at different reaction temperatures;
FIG. 4A is a graph showing the ABTS free radical scavenging rate results for alpha-lipoic acid-arginine obtained at different reaction temperatures;
FIG. 4B is a graph showing the ABTS free radical scavenging rate results of alpha-lipoic acid-matrine obtained at different reaction temperatures;
FIG. 4C shows ABTS free radical scavenging results for α -lipoic acid-synephrine obtained at different reaction temperatures;
FIG. 5A is a graph showing the results of Nrf2 tests on alpha-lipoic acid-arginine, alpha-lipoic acid-matrine, and alpha-lipoic acid-synephrine obtained by reaction at 20 ℃;
FIG. 5B is a diagram showing the results of T-AOC detection of alpha-lipoic acid-arginine, alpha-lipoic acid-matrine, alpha-lipoic acid-synephrine obtained by reaction at 20 ℃;
FIG. 5C is a HO-1 detection result chart of alpha-lipoic acid-arginine, alpha-lipoic acid-matrine and alpha-lipoic acid-synephrine obtained by reaction at 20 ℃;
FIG. 6A is a graph of the results of IR spectroscopy of alpha-lipoic acid-arginine obtained at different reaction temperatures;
FIG. 6B is a graph showing the results of IR spectroscopy of alpha-lipoic acid-matrine obtained at different reaction temperatures;
fig. 6C is a graph showing infrared spectrum test results of the alpha-lipoic acid-synephrine obtained at different reaction temperatures.
Detailed Description
The terms as used herein:
"consisting of 8230%" \8230, preparation "and" comprising "are synonymous. The terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," or any other variation thereof, as used herein, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus.
The conjunction "consisting of 8230% \8230comprises" excludes any unspecified elements, steps or components. If used in a claim, this phrase shall render the claim closed except for the materials described except for those materials normally associated therewith. When the phrase "consisting of 8230' \8230"; composition "appears in a clause of the subject matter of the claims and not immediately after the subject matter, it defines only the elements described in the clause; other elements are not excluded from the claims as a whole.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or range defined by a list of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4," "1 to 3," "1 to 2 and 4 to 5," "1 to 3 and 5," and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
In the examples, the parts and percentages are by mass unless otherwise indicated.
"part by mass" means a basic unit of measure indicating a mass ratio of a plurality of components, and 1 part may represent an arbitrary unit mass, for example, 1g or 2.689 g. If we say that the part by mass of the component A is a part by mass and the part by mass of the component B is B part by mass, the ratio of the part by mass of the component A to the part by mass of the component B is a: b. alternatively, the mass of the A component is aK and the mass of the B component is bK (K is an arbitrary number, and represents a multiple factor). It is unmistakable that, unlike the parts by mass, the sum of the parts by mass of all the components is not limited to 100 parts.
"and/or" is used to indicate that one or both of the illustrated conditions may occur, e.g., a and/or B includes (a and B) and (a or B).
The application provides an alpha-lipoic acid-organic base ion salt, which is obtained by connecting alpha-lipoic acid and an organic base through a chemical bond; the organic base has strong basicity and is easy to have acid-base neutralization reaction with carboxyl, and a naked lone electron pair exists in an N atom in the organic base, so that the organic base is easy to accept a proton. Wherein, the carboxyl structure of the alpha-lipoic acid is a hydrogen bond donor, the amino group in the organic base is used as a hydrogen bond acceptor, and the salt is formed through acid-base reaction. The organic base may be any one of arginine, matrine, and synephrine, for example.
Preferably, the alpha-lipoic acid-organic base ion salt is selected from any one of formula I to formula III:
the formula I is prepared from alpha-lipoic acid and arginine, guanidine groups of an arginine side chain easily capture a proton due to the existence of a naked lone electron pair in N atoms connected by double bonds, and meanwhile, three nitrogen atoms and carbon atoms actually form a planar structure, all nitrogen atoms are hybridized by sp2, have 6 pi electrons in total, form a large pi bond together, and the structure does not have a naked lone electron pair any more and is very stable, so that another proton cannot be continuously attracted. Thus, 1 part arginine can bind to 1 part alpha-lipoic acid, but not to two parts alpha-lipoic acid.
The compound of formula II is prepared from alpha-lipoic acid and matrine, wherein the matrine has stronger alkalinity, 2 nitrogen atoms are in the molecule, N16 is in an amide state and almost has no alkalinity, N1 belongs to tertiary amine, and three valence is all connected on a ring, the basicity is stronger because the steric image of the compound is convenient for accepting protons, and the influence of the steric effect is weakened, the lone electron pair of amide nitrogen (N16) atoms and carbonyl form a p-pi conjugated effect and are difficult to accept protons, so that 1 part of matrine can be combined with 1 part of alpha-lipoic acid.
Wherein, the formula III is prepared by alpha-lipoic acid and synephrine, amino in the molecular structure of the synephrine is hybridized by sp3, and one lone electron pair is remained and can react with 1 part of the alpha-lipoic acid.
The present application also provides a method for preparing an alpha-lipoic acid-organic base ion salt, referring to fig. 1, comprising:
s100: dissolving alpha-lipoic acid and organic base in an ethanol solution, mixing and reacting to obtain a reaction solution.
Wherein the organic base is selected from arginine, matrine, and synephrine. The mol ratio of alpha-lipoic acid to organic base is 1: (0.8 to 1.5), for example, 1. Preferably, the molar ratio of alpha-lipoic acid to organic base is 1:1.
wherein the volume ratio of the mass of the alpha-lipoic acid and the organic base to the volume of the ethanol solution is 1g: (1.5-10) ml, for example, 1g: (1.5-8) ml, or 1g: (1.5-5) ml, or 1g: (1.5-3) ml, more specifically, for example, 1g:1.5ml, or 1g:2ml, or 1g:3ml, or 1g:4ml, or 1g:5ml.
Preferably, the concentration of the ethanol solution is in the range of 30% to 70%, and may for example be 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65% or 70%.
Preferably, ultrasonic waves are applied during the process of dissolving and mixing alpha-lipoic acid and organic base in an ethanol solution, and the frequency of the ultrasonic waves is 30-50KHz, such as 30KHz, 33KHz, 35KHz, 38KHz, 40KHz, 42KHz, 45KHz, 47KHz or 50KHz.
Wherein, alpha-lipoic acid and organic base are dissolved and mixed in ethanol solution, and then the mixture is subjected to heat preservation reaction at the temperature of 20-80 ℃, for example, 20-70 ℃, or 20-60 ℃, or 20-50 ℃, or 20-40 ℃; the reaction time is 4 to 10 hours, and may be, for example, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 9 hours, or 10 hours, or any value between 4 and 10 hours.
S200: and (3) evaporating the reaction solution under vacuum to remove ethanol, and then freeze-drying to remove water to obtain the alpha-lipoic acid-organic alkali ion salt.
After the alpha-lipoic acid and the organic base react in the ethanol solution, evaporating the reaction solution at a corresponding reaction temperature under a vacuum condition to remove ethanol, and then performing freeze drying to remove water to obtain the alpha-lipoic acid-organic base ionic salt.
The application also provides application of the alpha-lipoic acid-organic alkali ion salt in preparation of cosmetics, health products and medicines.
Alpha-lipoic acid is an endogenous antioxidant, can remove free radicals of organisms, can promote the organisms to synthesize vitamin C by using glucose, can promote the organisms to synthesize glutathione, and can effectively remove melanin, so the alpha-lipoic acid-organic base ionic salt can be used for preparing cosmetics to improve the whitening effect of the cosmetics.
The alpha-lipoic acid can also assist coenzyme to carry out physiological metabolism favorable for the immunity of organisms, and can be used for preparing health-care products. Alpha-lipoic acid also has anti-inflammatory effect, can inhibit the activity of kinase, transforming factor, d-tumor necrosis factor and collagenase, has anti-aging effect, can preserve and regenerate other antioxidants, has good health care effect on human body, and can be widely applied to preventing and treating heart disease, diabetes, liver disease, senile dementia and the like.
The alpha-lipoic acid-organic base ionic salt is obtained by connecting alpha-lipoic acid and organic base through hydrogen bonds, so that the water solubility of the alpha-lipoic acid and the organic base is improved, the stability of the alpha-lipoic acid is improved, and the application of the alpha-lipoic acid-organic base ionic salt in an antioxidant product is improved. The preparation method of the alpha-lipoic acid-organic alkali ion salt is simple to operate, green and environment-friendly, uses water and ethanol as solvents, avoids the use of toxic organic solvents, and avoids the influence of high-temperature self-polymerization on the efficacy of the alpha-lipoic acid due to low-temperature reaction.
Embodiments of the present application will be described in detail below with reference to specific examples, but those skilled in the art will appreciate that the following examples are only illustrative of the present application and should not be construed as limiting the scope of the present application. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
Example 1
Respectively weighing 10mmol of alpha-lipoic acid (2.06 g) and 10mmol of arginine (1.74 g) in four single-neck flasks, adding 4ml of deionized water and 2ml of ethanol, ultrasonically dissolving, adding a stirrer, and respectively reacting at 20 ℃, 40 ℃, 60 ℃ and 80 ℃ for 4h. After the reaction is finished, the alpha-lipoic acid-arginine ionic salt is obtained by rotationally evaporating the alpha-lipoic acid-arginine ionic salt under the vacuum condition at the corresponding reaction temperature to remove ethanol, and then freeze-drying the alpha-lipoic acid-arginine ionic salt to remove water.
Example 2
Respectively weighing 10mmol lipoic acid (2.06 g) and 10mmol matrine (2.48 g) in four single-neck flasks, adding 4ml and 2ml of deionized water, ultrasonically dissolving, and respectively reacting at 20 ℃, 40 ℃, 60 ℃ and 80 ℃ for 4h. After the reaction is finished, the alpha-lipoic acid-matrine ionic salt is obtained by rotationally evaporating the alpha-lipoic acid-matrine ionic salt under the vacuum condition at the corresponding reaction temperature to remove ethanol, and then freeze-drying to remove water.
Example 3
10mmol of lipoic acid (2.06 g) and 10mmol of synephrine (1.67 g) are respectively weighed into four single-neck flasks, 4ml of deionized water and 2ml of ethanol are added, ultrasonic dissolution is carried out, and the mixture is reacted for 4 hours at the temperature of 20 ℃, 40 ℃, 60 ℃ and 80 ℃. After the reaction is finished, the alpha-lipoic acid-synephrine ionic salt is obtained by removing ethanol by rotary evaporation at a corresponding temperature under a vacuum condition, and then freeze-drying to remove water.
Comparative example 1
Respectively weighing 10mmol of lipoic acid (2.06 g) and 10mmol of nicotinamide (1.22 g) in four single-neck flasks, adding 4ml of deionized water and 2ml of ethanol, ultrasonically dissolving, and respectively reacting at 20 ℃, 40 ℃, 60 ℃ and 80 ℃ for 4h. After the reaction is finished, the thioctic acid and the nicotinamide powder are subjected to rotary evaporation at a corresponding temperature under a vacuum condition to remove ethanol, and then are subjected to freeze drying and water removal to obtain a product, namely a thioctic acid and nicotinamide powder mixture, wherein the thioctic acid and the nicotinamide powder mixture do not react.
Comparing the properties of the ionic salt prepared in the embodiment 1-3, alpha-lipoic acid, arginine, matrine and synephrine, wherein A: alpha-lipoic acid; b: alpha-lipoic acid-arginine; c: alpha-lipoic acid-matrine; d: alpha-lipoic acid-synephrine; e: arginine; f: matrine; g: synephrine.
Test example 1 Water solubility and stability
1. Water solubility
When 10mg of each of a to G was dissolved in 1ml of water, α -lipoic acid was insoluble in water, but α -lipoic acid-organic base ion salt was well soluble in water, as shown in table 1 and fig. 2.
TABLE 1 Water solubility of the respective alpha-lipoic acid-organic base ion salts
2. Stability of
A-D is prepared into 2 percent solution to be respectively subjected to appearance and odor tests at room temperature and 48 ℃ for 24H, and the results are shown in Table 2, and alpha-lipoic acid is oxidized to generate H 2 S gas generates sulfur-containing odor, and the alpha-lipoic acid after being salted is more stable and is not easy to be oxidized.
TABLE 2 stability of the respective alpha-lipoic acid-organic base ion salts
| Sample (I) | A | B | C | D |
| Smell(s) | With sulfur-containing odor | No sulfur-containing odor | No sulfur-containing odor | No sulfur-containing odor |
| Appearance of the product | Light yellow solution | Light yellow solution | Yellow solution | Brown solution |
Test example 2 Oxidation resistance
1. DPPH free radical scavenging force experiment
0.002g of DPPH is weighed and dissolved in 50mL of ethanol to prepare 0.1mM DPPH solution, the absorbance of the solution is about 0.7 at 507nm under an enzyme labeling instrument, and the solution is stored in a dark place. Respectively weighing 50mg of A, dissolving the A in 5ml of absolute ethyl alcohol, dissolving 92.25mg of B obtained at different reaction temperatures, 110.4mg of C obtained at different reaction temperatures and 90.58mg of D obtained at different reaction temperatures in pure water to respectively prepare solutions with the alpha-lipoic acid net content of 10mg/ml, and diluting the solutions to 5mg/ml and 1mg/ml gradient sample solutions. The prepared solution is added into a 96-well plate according to a certain proportion, incubated for 30 minutes at room temperature in the dark, and the absorbance is measured. The 96-pore plate comprises three groups, each group is provided with 3 multiple pores, and the adding amount of each pore is distributed as follows:
sample (sample group): sample solution 100uL of DPPH alcoholic solution 100uL (3 wells per concentration);
blank (blank): sample solution 100uL + absolute ethanol 100uL (3 wells per concentration);
control (control group): 100uL of DPPH alcoholic solution and 100uL of water;
and (4) calculating a result: DPPH clearance = (1- (Sample-Blank)/Control) = 100%.
As shown in fig. 3A to 3C, fig. 3A shows DPPH radical scavenging rate results of α -lipoic acid-arginine obtained at different reaction temperatures, where the DPPH radical scavenging rate of α -lipoic acid-arginine at 10mg/ml is 25% to 37%, which is much higher than DPPH radical scavenging rate (only 15%) at the same concentration of α -lipoic acid, and the reaction temperature has little influence on DPPH radical scavenging rate of α -lipoic acid-arginine; fig. 3B shows DPPH radical clearance results of α -lipoic acid-matrine obtained at different reaction temperatures, where the DPPH radical clearance reaches 25% to 55% at 10mg/ml of α -lipoic acid-matrine, and the reaction temperature has a great influence on the DPPH radical clearance of α -lipoic acid-matrine, and the effect is the best at 20 ℃ and reaches 55%, which is much higher than the DPPH radical clearance (only 15%) at the same concentration of α -lipoic acid; fig. 3C shows DPPH free radical scavenging rate results of α -lipoic acid-synephrine obtained at different reaction temperatures, where the DPPH free radical scavenging rate of α -lipoic acid-synephrine at 10mg/ml is 45% -53%, which is much higher than DPPH free radical scavenging rate (only 15%) at the same concentration of α -lipoic acid, and the influence of the reaction temperature on DPPH free radical scavenging rate of α -lipoic acid-synephrine is not great.
The combination of alpha-lipoic acid and organic base can improve DPPH free radical scavenging effect, alpha-lipoic acid-synephrine has the best effect, the reaction temperature has obvious influence on alpha-lipoic acid-matrine ion salt, and the DPPH free radical scavenging activity is poorer when the temperature is higher.
2. ABTS free radical scavenging ability test
Preparing 7.4mmol/L ABTS stock solution and 2.6mmol/L K by using pure water 2 S 2 O 8 A stock solution; then 5ml of ABTS stock solution was taken and 88. Mu.l of K 2 S 2 O 8 Mixing the stock solution, standing for 12-16 hr, and making into ABTS working solution. 0.4mL of ABTS working solution is taken and diluted by pure water, and the light absorption value at 405nm at normal temperature is required to be about 0.7. 0.2mL ABTS working solution is mixed with 10ul of sample solution with different concentrations, 0.2mL pure water is mixed with 10ul of sample solution to form a control group, 0.2mL ABTS working solution is mixed with 10ul of pure water to form a blank group, the blank group is kept stand for 6min in a dark place at normal temperature, the absorbance is measured at the wavelength of 405nm, the parallel times are 3 times, and the details are as follows:
sample: 10. Mu.l sample solution + 200. Mu.l ABTS working solution;
blank: 10. Mu.l of the sample solution + 200. Mu.l of pure water;
control:10 mul distilled water +200 mul ABTS working solution;
and (4) calculating a result: ABTS clearance = (1- (Sample-Blank)/Control) = 100%.
As shown in fig. 4A to 4C, fig. 4A shows the ABTS radical clearance rate results of α -lipoic acid-arginine obtained at different reaction temperatures, the ABTS radical clearance rate of α -lipoic acid-arginine at 10mg/ml reaches 27% to 37%, which is higher than the ABTS radical clearance rate (only 7%) at the same concentration of α -lipoic acid, and the reaction temperature has little influence on the ABTS radical clearance rate of α -lipoic acid-arginine; fig. 4B shows the ABTS free radical scavenging rate results of α -lipoic acid-matrine obtained at different reaction temperatures, where the ABTS free radical scavenging rate of α -lipoic acid-matrine reaches 30% to 72% at 10mg/ml, and the reaction temperature has a great influence on the ABTS free radical scavenging rate of α -lipoic acid-matrine, and the effect is the best at 20 ℃, which is much higher than the ABTS free radical scavenging rate (only 7%) at the same concentration of α -lipoic acid; fig. 4C shows the ABTS radical scavenging rate results of α -lipoic acid-synephrine obtained at different reaction temperatures, which reaches 100% at 10mg/ml and has little effect on it by reaction temperature, much higher than the ABTS radical scavenging rate (only 7%) at the same concentration of α -lipoic acid.
The antioxidant capacity test result shows that the combination of alpha-lipoic acid and organic base can improve the antioxidant activity, the antioxidant activity of alpha-lipoic acid-synephrine ionic salt is the best, the reaction temperature has obvious influence on the antioxidant activity of alpha-lipoic acid-matrine ionic salt, and the higher the temperature is, the poorer the antioxidant activity is.
Test example 3 cellular antioxidant test
The alpha-lipoic acid-organic base salt and the alpha-lipoic acid prepared at the reaction temperature of 20 ℃ in the examples 1 to 3 are subjected to a cell antioxidation experiment, a cell-level oxidative stress damage is performed through hydrogen peroxide to establish an oxidative stress damage model to evaluate the antioxidation performance of the alpha-lipoic acid-organic base salt, and the detection of human nuclear factor E2-related factor 2 (Nrf 2) ELISA, the detection of total antioxidant capacity (T-AOC) kit and the detection of human heme oxygenase 1 (HO-1) ELISA are respectively performed.
Among them, nrf2 is a key factor in cellular oxidative stress and plays an important role in the redox regulation of cells. The Nrf2 signal path can resist oxidative stress reaction caused by internal and external oxidation and stimulation of chemical substances and the like, plays a very important role in defending various external injuries of the organism, is the most important endogenous antioxidant signal path in the organism, and has stronger antioxidant effect when the Nrf2 content is higher.
T-AOC is the total antioxidant level formed by various antioxidant substances, antioxidant enzymes and the like, and in order to protect cells and organisms from oxidative stress damage caused by active oxygen free radicals, the total antioxidant capacity can be used for evaluating the antioxidant capacity of lipoic acid.
HO-1 is an important antioxidant enzyme playing a key role in the protection of cells of endogenous and exogenous origin against harmful stimuli. The Nrf2/HO-1 pathway is widely involved in the oxidative stress injury resistance of tissues and organs and is one of the most important endogenous protection systems in organisms.
Nrf2 test and T-AOC detection experiment:
(1) Cell inoculation: adjusting human immortalized keratinocyte suspension density to 4 × 10 5 After each mL, the cells were inoculated in a 6-well plate, 2 mL/well, placed at 37 ℃ in 5% CO 2 Culturing in an incubator for 24h.
(2)H 2 O 2 Inducing oxidative damage: discard old medium and add H 2 O 2 Working solution (180. Mu.M), 2 mL/well, cell negative well, equal amount of PBS, placed at 37 ℃ in 5% CO 2 Culturing in a cell culture box for 4h, and then discarding.
(3) Diluting and adding samples to be tested: diluting the sample to working concentration with complete culture medium as diluent, adding into cells, 2 mL/well, adding equal amount of complete culture medium into negative control group and positive group, standing at 37 deg.C and 5% CO 2 Culturing in an incubator for 24h.
(4) Extracting a substance to be detected: cells were digested with pancreatin, and if the digestion was incomplete, the cells were scraped from the 6-well plate using a cell scraper, collected and centrifuged. Discarding the supernatant, adding 1ml PBS for washing, discarding the supernatant, and adding 100ul cell extract; dispersing cells by ultrasonic treatment for 5min, standing on ice for 30min, and then ultrasonic treatment for 10min. After that, the mixture is centrifuged at 10000rpm for 10min, the precipitate is discarded, and the supernatant is reserved for later use.
(5) 55ul of the supernatant was diluted 5-fold and then subjected to Nrf2 experiments using a Saimerfin kit.
(6) 72ul of the supernatant was taken undiluted and then tested using the T-AOC kit.
HO-1 detection experiment:
(1) Cell inoculation: adjusting human immortalized keratinocyte suspension density to 2 × 10 4 After each mL, the cells were inoculated in a 96-well plate, 100 ul/well, incubated at 37 ℃ with 5% CO 2 Culturing in an incubator for 24h.
(2)H 2 O 2 Inducing oxidative damage: discard old medium and add H 2 O 2 Working solution (180. Mu.M), 100 ul/well, cell negative well, and equal amount of PBS were added, placed at 37 ℃ and 5% CO 2 Culturing in a cell culture box for 4h, and discarding.
(3) Diluting and adding samples to be tested: diluting the sample to working concentration with complete culture medium as diluent, adding into cells, 100 ul/well, adding equal amount of complete culture medium into negative control group and positive group, standing at 37 deg.C and 5% CO 2 Culturing in an incubator for 24h.
(4) The supernatant was diluted 8-fold and then tested with a biologies HO-1 detection kit.
The results of Nrf2 test, T-AOC test and HO-1 test are shown in FIGS. 5A to 5C, respectively, and the results of cell experiments show that the alpha-lipoic acid-organic base salt has improved lipoic acid antioxidant activity and different antioxidant effects for different antioxidant pathways.
Test example 4 Infrared comparison
Fourier transform infrared spectroscopy tests on samples prepared by freeze-drying the alpha-lipoic acid-organic base ionic salt prepared in the above examples 1 to 3 at different reaction temperatures are shown in fig. 6A to 6C, where fig. 6A shows the results of alpha-lipoic acid-arginine, fig. 6B shows the results of alpha-lipoic acid-matrine, and fig. 6C shows the results of alpha-lipoic acid-synephrine.
Comparing the infrared spectra, 1700cm in alpha-lipoic acid-arginine and alpha-lipoic acid-synephrine compounds -1 The peak of carboxyl group disappears, the carboxyl group is ionized to form R-COO-group,ionic bonds are formed, so that the influence of temperature is small; and in the alpha-lipoic acid-matrine, the carboxyl peak is from 1700cm -1 Moving to 1720cm in high frequency direction -1 The reason is that only hydrogen bond combination is generated between the two compounds, and the two compounds are influenced by a hydrogen bond conjugation effect, so that the compound is greatly influenced by temperature, and the infrared spectrum test result is consistent with the experimental result.
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solutions of the present application, and not to limit the same; although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present application.
Moreover, those skilled in the art will appreciate that while some embodiments herein include some features included in other embodiments, rather than other features, combinations of features of different embodiments are meant to be within the scope of the application and form different embodiments. For example, in the claims above, any of the claimed embodiments may be used in any combination. The information disclosed in this background section is only for enhancement of understanding of the general background of the application and should not be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
Claims (10)
1. The alpha-lipoic acid-organic base ion salt is characterized in that the alpha-lipoic acid-organic base ion salt is obtained by connecting alpha-lipoic acid and an organic base through a chemical bond; the organic base has strong basicity, and a naked lone electron pair exists in an N atom in the organic base, so that the organic base is easy to accept protons.
2. The α -lipoic acid-organic base ion salt according to claim 1, characterised in that it is selected from any one of formulae I to III:
3. a method for preparing alpha-lipoic acid-organic base ion salt is characterized by comprising the following steps:
dissolving, mixing and reacting alpha-lipoic acid and organic base in an ethanol solution to obtain a reaction solution;
and (3) evaporating the reaction solution under vacuum to remove ethanol, and freeze-drying to remove water to obtain the alpha-lipoic acid-organic alkali ion salt.
4. The process according to claim 3, wherein the organic base is selected from arginine, matrine and synephrine.
5. The method according to claim 3, wherein the molar ratio of the alpha-lipoic acid to the organic base is 1: (0.8-1.5).
6. The method according to claim 5, wherein the molar ratio between the alpha-lipoic acid and the organic base is 1:1.
7. the method according to claim 3, wherein the ratio of the mass of the alpha-lipoic acid and the organic base to the volume of the ethanol solution is 1g: (1.5-10) ml;
preferably, the concentration of the ethanol solution is in the range of 30% -70%.
8. The preparation method according to claim 3, wherein ultrasonic waves are applied during the dissolving and mixing process, and the frequency of the ultrasonic waves is 30-50kHz.
9. The process according to claim 3, wherein the reaction is carried out at a temperature of 20 ℃ to 80 ℃ for 4 to 10 hours.
10. Use of the alpha-lipoic acid-organic base ion salt of claim 1 or 2 for the preparation of cosmetics, nutraceuticals, pharmaceuticals.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006265202A (en) * | 2005-03-25 | 2006-10-05 | Hamari Chemicals Ltd | Alpha-lipoic acid amino acid salt |
| CN1887882A (en) * | 2006-08-08 | 2007-01-03 | 武汉远大制药集团有限公司 | Dextro lipoic amidate and its prepn |
| CN105001195A (en) * | 2015-07-06 | 2015-10-28 | 南京海融医药科技有限公司 | New crystal form of R(+)-thioctic acid-L-lysinate and preparation method thereof |
| CN106138037A (en) * | 2016-08-24 | 2016-11-23 | 江苏农林职业技术学院 | The compositions of a kind of antibiont cell oxidative damage and application thereof |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006265202A (en) * | 2005-03-25 | 2006-10-05 | Hamari Chemicals Ltd | Alpha-lipoic acid amino acid salt |
| CN1887882A (en) * | 2006-08-08 | 2007-01-03 | 武汉远大制药集团有限公司 | Dextro lipoic amidate and its prepn |
| CN105001195A (en) * | 2015-07-06 | 2015-10-28 | 南京海融医药科技有限公司 | New crystal form of R(+)-thioctic acid-L-lysinate and preparation method thereof |
| CN106138037A (en) * | 2016-08-24 | 2016-11-23 | 江苏农林职业技术学院 | The compositions of a kind of antibiont cell oxidative damage and application thereof |
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