CN113046397A - Non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid - Google Patents
Non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid Download PDFInfo
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- CN113046397A CN113046397A CN202110340800.8A CN202110340800A CN113046397A CN 113046397 A CN113046397 A CN 113046397A CN 202110340800 A CN202110340800 A CN 202110340800A CN 113046397 A CN113046397 A CN 113046397A
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/345—Alcohols containing more than one hydroxy group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/67—Vitamins
- A61K8/676—Ascorbic acid, i.e. vitamin C
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/735—Mucopolysaccharides, e.g. hyaluronic acid; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/88—Polyamides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
- A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
Abstract
The invention discloses a non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid, which utilizes lipase to catalyze the reaction of hydroxyl at 6-position of L-ascorbic acid and carboxyl of gamma-polyglutamic acid so as to generate 6-O-PGA-L-ascorbic acid.
Description
Technical Field
The invention relates to a non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid, belonging to the technical field of chemical synthesis.
Background
In the research, the L-ascorbic acid derivative is generally synthesized by a sulfation method, and compared with a chemical synthesis method, the biological enzyme synthesis method is mild and environment-friendly.
The enzyme catalysis has the characteristics of high selectivity, reaction specificity, mildness and the like, and is widely applied to industrial production. Because lipase has the characteristics of stability and low price, the lipase can catalyze the reaction with industrial application value, and in most organic synthesis reactions, the lipase has good stability at high temperature, extreme pH and organic solvent, can be repeatedly used, is convenient to recover, and can sufficiently meet the requirement of industrial continuous production. Currently, commercially available lipases mainly include Immobilized CALB, Novozym 435, Rhizomucor Miehei Lipase (RML), Aspergillus niger lipase (ASL), Pseudomonas cepacia lipase (PSL), Pseudomonas Fluorescens Lipase (PFL), and the like.
Lipases can catalyze both ester hydrolysis and ester synthesis reactions, which mainly involve esterification, transesterification, acidolysis and alcoholysis. When the system contains a trace amount of water or is an anhydrous organic solvent, the system is called a non-aqueous phase system, when the lipase is in the non-aqueous phase system, the lipase catalyzes a synthesis reaction of ester, and when the lipase is on an interface of a hydrophobic solvent and water, the space structure of the lipase is changed under the action of interface energy, an active center is exposed, and the lipase has activity.
Disclosure of Invention
The invention overcomes the defects of the prior art and provides a non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid, which uses lipase to catalyze the reaction of hydroxyl at 6-position of L-ascorbic acid and carboxyl of gamma-polyglutamic acid so as to generate 6-O-PGA-L-ascorbic acid.
A non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid comprises the following steps:
(1) taking tert-butyl alcohol, pyridine, lipase and a molecular sieve, fully mixing and dissolving, adding 4-5g of L-ascorbic acid and 4-5g of polyglutamic acid, placing in a water bath kettle at 45-50 ℃, and carrying out oscillation reaction for 48 hours to obtain a reaction solution;
(2) standing the reaction solution obtained in the step (1), filtering, and keeping a filtrate A;
(3) performing rotary evaporation on the filtrate A reserved in the step (2) to obtain a crude product;
(4) adding purified water into the crude product obtained in the step (3) for dissolving, standing for layering, retaining a water phase, and filtering the water phase to retain a filtrate B;
(5) adding ethanol into the filtrate B to obtain precipitate, keeping the precipitate, and drying the precipitate to obtain the low molecular weight 6-O-PGA-L-ascorbic acid.
Further, the low molecular weight 6-O-PGA-L-ascorbic acid described in the above-mentioned non-aqueous enzymatic synthesis method has a relative molecular weight of 0.5 to 41 kDa.
Further, the structure of the low molecular weight 6-O-PGA-L-ascorbic acid produced by the above-mentioned non-aqueous enzymatic synthesis method is as follows:
a is a natural number not less than 0, c is a natural number not less than 0, and b is a natural number not less than 1.
Further, adding the tert-butyl alcohol and the pyridine in the step (1) according to a volume ratio of 1: 1; the mass volume ratio of the added lipase is 0.5-1% of the volume of the mixed solution of tert-butyl alcohol and pyridine; the mass volume ratio of the molecular sieve is 4-10% of the volume of the mixed solution of tert-butyl alcohol and pyridine; the mass volume ratio of the ascorbic acid is 1.5-3% L-of the volume of the mixed solution of tert-butyl alcohol and pyridine; the mass volume ratio of the added polyglutamic acid is 1.5-3% of the volume of the mixed solution of the tert-butyl alcohol and the pyridine.
Further, the lipase in the step (1) is one of Immobilized CALB, Novozym 435, Rhizomucor Miehei Lipase (RML), Aspergillus niger lipase (ASL), Pseudomonas cepacia lipase (PSL) and Pseudomonas Fluorescens Lipase (PFL).
Further, the polyglutamic acid in the step (1) is gamma-polyglutamic acid, and the molecular weight is 0.5-20 kDa.
Further, the volume of ethanol added in the step (5) is 2 times of the volume of the filtrate B.
The application of the low molecular weight 6-O-PGA-L-ascorbic acid prepared by the non-aqueous phase enzymatic synthesis method in preparing moisturizing and whitening products.
A moisturizing and whitening composition prepared from low-molecular-weight 6-O-PGA-L-ascorbic acid prepared by the non-aqueous phase enzymatic synthesis method comprises the following components in parts by weight:
0.1-5 parts of sodium hyaluronate, 0.1-5 parts of 6-O-PGA-L-ascorbic acid, 0.1-10 parts of jojoba oil, 0.1-10 parts of glycerol, 0.1-3 parts of centella asiatica extract, 0.1-3 parts of liquorice extract, 0.1-2 parts of salicylic acid, 1-5 parts of emulsifier, 0.1-3 parts of surfactant, 1-5 parts of solubilizer, 1-4 parts of rheology regulator, 0.1-1 part of essence, 0.5-3 parts of preservative and the balance of water, wherein the centella asiatica extract and the liquorice extract are purchased from new biotechnology limited company.
Has the advantages that:
(1) compared with a chemical synthesis method, the biological enzyme method disclosed by the invention is mild and environment-friendly.
(2) The 6-O-PGA-L-ascorbic acid prepared by the biological enzyme method has lower relative molecular weight than that prepared by a chemical synthesis method, and the distribution range of the relative molecular weight is concentrated.
(3) The low molecular weight 6-O-PGA-L-ascorbic acid provided by the invention can be applied to various fields, including but not limited to the fields of medicines, cosmetics, foods and the like.
Detailed Description
In order to make the technical solutions in the present application better understood, the present invention is further described below with reference to examples, which are only a part of examples of the present application, but not all examples, and the present invention is not limited by the following examples.
EXAMPLE 16 non-aqueous enzymatic preparation of O-PGA-L-ascorbic acid
1. Preparation method
Adding 100mL of tert-butyl alcohol, 100mL of pyridine, 1g of lipase and 10g of molecular sieve into a 500mL conical flask with a plug, shaking to dissolve the lipase, then adding 5g of L-ascorbic acid and 5g of polyglutamic acid, placing the mixture into a constant-temperature shaking water bath kettle at 50 ℃, shaking to react for 48 hours at the rotating speed of 150ppm, standing, filtering, performing rotary evaporation on the filtrate to obtain a crude product, dissolving the crude product with purified water, standing for layering to obtain a water phase, filtering, adding 2 times of ethanol to obtain a precipitate, and drying to obtain the 6-O-PGA-L-ascorbic acid.
2. Determination of 6-O-PGA-L-ascorbic acid content
The content of the obtained 6-O-PGA-L-ascorbic acid is detected, and the ultraviolet absorption value of the gamma-polyglutamic acid standard solution is used as a detection object, and the specific detection method is as follows.
High performance liquid chromatograph: shimadzu, LC-20 AT. Chromatographic conditions are as follows: a chromatographic column, TSK-GEL G4000 WPXL; a detector, an ultraviolet detector; detection wavelength, 210 nm; mobile phase, 0.3mol/L sodium sulfate solution, flow rate of 0.5mL/min, column temperature of 30 ℃, injection volume of 20 μ L.
Treating a standard substance: selecting gamma-polyglutamic acid standard substances (content is more than or equal to 99.0%) with different relative molecular weights, dissolving with mobile phase, respectively preparing into 1.0mg/mL gamma-polyglutamic acid standard solutions, filtering with microporous membrane with pore diameter of 0.22 μm, and ultrasonic degassing for 15 min.
Sample treatment: a sample of 6-O-PGA-L-ascorbic acid obtained in example 1 was weighed, dissolved in a mobile phase to prepare a 1.0mg/mL sample solution of 6-O-PGA-L-ascorbic acid, filtered through a 0.22 μm pore size microfiltration membrane, and degassed by ultrasonic waves for 15 min.
Content determination: injecting the 6-O-PGA-L-ascorbic acid sample solution to be detected into a chromatographic column, recording peak areas, obtaining that the content of the 6-O-PGA-L-ascorbic acid is 88.41%, and the retention time is concentrated in 10.723 to 11.478.
TABLE 1 Standard retention time and its relative molecular weight
Example 2 preparation of moisturizing and whitening composition 1
1. The raw material composition is shown in the following table:
table 1 ingredient table of moisturizing and whitening composition
Note: centella asiatica extract and glycyrrhiza extract were purchased from new biotechnology limited.
2. Preparation method
Sequentially adding the raw materials of the phase A component into a beaker, heating to 80 ℃, uniformly stirring without insoluble substances, keeping the temperature for 20min, cooling to below 45 ℃, adding the raw materials of the phase B component, and stirring until uniform without insoluble substances; premixing the phase C raw materials, stirring uniformly, slowly adding into a beaker, stirring uniformly, cooling to normal temperature, and filtering with filter cloth to obtain the moisturizing and whitening composition 1.
Example 3 preparation of moisturizing and whitening composition 2
Preparation method of moisturizing and whitening composition 2 as described in example 2, the amount of 6-O-PGA-L-ascorbic acid added was increased to 3%.
Example 4 moisturizing test of moisturizing and whitening products of the present invention
The whitening and moisturizing composition 1 and the whitening and moisturizing composition 2 obtained in example 2 and example 3 were subjected to a moisturizing test by the following specific method: the method comprises the steps of placing an ammonium sulfate-preventing supersaturated solution in a closed drying container, measuring the relative humidity in the container, simulating human skin by using a medical transparent 3M adhesive tape, weighing, adhering to a transparent glass plate, arranging 3 parallel groups for each sample, taking glycerin as a control group, sucking 100 mu L of the sample, smearing the sample on the medical transparent 3M adhesive tape of each group, placing the sample in a constant-humidity container, weighing at intervals of specific time, calculating a water retention value, and evaluating the water retention effect.
TABLE 3 moisture retention test results
As can be seen from the above table, the water retention values of the samples of examples 2 and 3 are greater than those of the glycerin control group, which indicates that the moisturizing and whitening composition of the present invention has good moisturizing performance.
Example 5 measurement of melanin synthesis inhibition ratio of moisturizing and whitening composition of the present invention
The inhibition rate of melanin synthesis was determined for the serum and cream obtained in examples 3 and 4 based on an in vitro recombinant 3D melanin skin model, and the procedure was performed in a clean bench, as follows:
randomly placing the in-vitro recombinant 3D melanin skin model in a 6-hole cell culture plate, setting a control group and a sample group, marking the 6-hole plate, adding 3.7mL of M-TA culture solution into each hole, placing the M-TA culture solution into a sterile suspension, transferring the in-vitro recombinant 3D melanin skin model cultured on a gas-liquid surface for 3 days (TA3) into the sterile suspension, and placing the sterile suspension into a CO2 incubator for culture (37 ℃, 5% CO2 and 95% relative humidity). The control and sample groups were then subjected to continuous 7 days of UVB irradiation at a dose of 50mJ/cm 2/time. Surface administration was carried out on day 6 of the gas-liquid surface (TA6) and day 8 of the gas-liquid surface (TA8), and the dose was 10. mu.L. The positive control group selected kojic acid with administration concentration of 0.05%. After the administration is finished, the skin model is cleaned three times by adopting ultrapure water, and the residues of the tested substances are removed. The external recombinant 3D melanin skin model was transferred to a 1.5mL EP tube, 150. mu.L of sodium deoxycholate solution (5g/L) was added, and a homogenate was prepared ultrasonically at low temperature.
And (3) melanin content determination: the homogenate was frozen at 10000 Xg for 5min and the pellet was used for melanin content determination. To the EP tube, 150. mu.L of NaOH solution (1mol/L) was added, heated in a water bath at 100 ℃ for 10min, and shaken to dissolve the melanin sufficiently in the EP tube. 100 μ L of the solution was placed in a 96-well plate, and absorbance was measured at 405nm with a microplate reader to calculate the melanin synthesis inhibition rate, and the specific results are shown in table 4.
TABLE 4 measurement results of melanin synthesis inhibition
Compared with the blank group, the kojic acid group, the example 2 sample group and the example 3 sample group have very significant differences (P <0.001), which shows that the kojic acid, the example 2 sample and the example 3 sample all have melanin synthesis inhibition effects, and the example 2 sample and the example 3 sample have better melanin synthesis inhibition effects than the kojic acid.
Claims (8)
1. A non-aqueous phase enzymatic synthesis method of low molecular weight 6-O-PGA-L-ascorbic acid is characterized by comprising the following steps:
(1) mixing tert-butyl alcohol, pyridine, lipase and molecular sieve thoroughly, dissolving, adding L-ascorbic acid and polyglutamic acid, placing in a water bath kettle at 45-50 deg.C, and shaking for 48 hr to obtain reaction solution;
(2) standing the reaction solution obtained in the step (1), filtering, and keeping a filtrate A;
(3) performing rotary evaporation on the filtrate A reserved in the step (2) to obtain a crude product;
(4) adding purified water into the crude product obtained in the step (3) for dissolving, standing for layering, retaining a water phase, and filtering the water phase to retain a filtrate B;
(5) adding ethanol into the filtrate B to obtain precipitate, keeping the precipitate, and drying the precipitate to obtain the low molecular weight 6-O-PGA-L-ascorbic acid.
2. The non-aqueous enzymatic synthesis method according to claim 1, wherein the low molecular weight 6-O-PGA-L-ascorbic acid has a relative molecular weight of 0.5 to 41 kDa.
3. The non-aqueous enzymatic synthesis method according to claim 1, wherein the tert-butanol and pyridine in step (1) are added in a volume ratio of 1: 1; the mass volume ratio of the added lipase is 0.5-1% of the volume of the mixed solution of tert-butyl alcohol and pyridine; the mass volume ratio of the molecular sieve is 4-10% of the volume of the mixed solution of tert-butyl alcohol and pyridine; the mass volume ratio of the ascorbic acid is 1.5-3% L-of the volume of the mixed solution of tert-butyl alcohol and pyridine; the mass volume ratio of the added polyglutamic acid is 1.5-3% of the volume of the mixed solution of the tert-butyl alcohol and the pyridine.
4. The non-aqueous enzymatic synthesis method of claim 1, wherein the lipase in step (1) is one of Immobilized CALB, Novozym 435, rhizomucor miehei lipase, aspergillus niger lipase, pseudomonas cepacia lipase and pseudomonas fluorescens lipase.
5. The non-aqueous enzymatic synthesis method of claim 1, wherein the polyglutamic acid in step (1) is gamma-polyglutamic acid, and the molecular weight is 0.5-20 kDa.
6. The non-aqueous enzymatic synthesis process of claim 1, wherein the volume of ethanol added in step (5) is 2 volumes of filtrate B.
7. Use of the low molecular weight 6-O-PGA-L-ascorbic acid prepared by the preparation method according to any one of claims 1 to 6 for preparing a moisturizing and whitening product.
8. A moisturizing and whitening composition formulated with the low molecular weight 6-O-PGA-L-ascorbic acid prepared by the preparation method of any one of claims 1 to 6, comprising the following components in parts by weight:
0.1-5 parts of sodium hyaluronate, 0.1-5 parts of 6-O-PGA-L-ascorbic acid, 0.1-10 parts of jojoba oil, 0.1-10 parts of glycerol, 0.1-3 parts of centella asiatica extract, 0.1-3 parts of liquorice extract, 0.1-2 parts of salicylic acid, 1-5 parts of emulsifier, 0.1-3 parts of surfactant, 1-5 parts of solubilizer, 1-4 parts of rheological regulator, 0.1-1 part of essence, 0.5-3 parts of preservative and the balance of water.
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| US20160015619A1 (en) * | 2013-02-12 | 2016-01-21 | Abio Co., Ltd. | Transparent sol, gel composition containing high concentrations of vitamin c and vitamin c derivative |
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