CN114836482B - Preparation method of oxyresveratrol - Google Patents
Preparation method of oxyresveratrol Download PDFInfo
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- CN114836482B CN114836482B CN202210776188.3A CN202210776188A CN114836482B CN 114836482 B CN114836482 B CN 114836482B CN 202210776188 A CN202210776188 A CN 202210776188A CN 114836482 B CN114836482 B CN 114836482B
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- mulberroside
- oxyresveratrol
- enzymolysis
- glucanase
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- 238000002360 preparation method Methods 0.000 title claims abstract description 23
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- 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
- A61K8/347—Phenols
-
- 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
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
The invention provides a preparation method of oxyresveratrol. Specifically, the invention provides a preparation method of oxyresveratrol, which comprises the following steps: (S1) providing a raw material containing mulberroside A; and (S2) carrying out enzymolysis treatment on the raw material containing the mulberroside A by using beta-glucanase to convert the mulberroside A into oxidized resveratrol so as to obtain an enzymolysis product. The method can obviously improve the yield of the oxyresveratrol, the zymohydrolysis rate of the mulberroside A can reach about 90 percent, and the yield of the oxyresveratrol is greatly increased. The method has mild reaction conditions, simple post-treatment and no need of special reagents, and is very suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a preparation method of oxyresveratrol.
Background
The oxyresveratrol prepared by the prior art is mainly prepared by a traditional extraction and purification method, but because the oxyresveratrol is low in content in plants and narrow in source range, the conventional extraction method is difficult to effectively obtain the oxyresveratrol.
CN103194493A describes a method for preparing oxyresveratrol by fermenting with ramulus mori powder as a fermentation substrate and Aspergillus niger as a fermentation strain, and the method has the problems of long time period from strain activation to fermentation ending, complex operation and difficult separation and purification caused by easy generation of other impurities in microbial fermentation.
CN104803830A describes a process for preparing high-purity oxyresveratrol by repeatedly extracting, extracting and decoloring with organic reagents such as ethanol and ethyl acetate, and the organic reagents used in the process, such as ethyl acetate and petroleum ether, are harmful to the environment and operators, and the operation is complicated.
Therefore, there is an urgent need in the art to develop a method for preparing oxyresveratrol safely, inexpensively, simply and efficiently.
Disclosure of Invention
The invention aims to provide a method for preparing oxyresveratrol safely, with low cost, simply and efficiently.
In a first aspect of the invention, a preparation method of oxyresveratrol is provided, which comprises the following steps:
(S1) providing a raw material containing mulberroside A;
(S2) carrying out enzymolysis treatment on the raw material containing the mulberroside A by using beta-glucanase to convert the mulberroside A into oxidized resveratrol so as to obtain an enzymolysis product:
in another preferred embodiment, in step (S2), the enzymolysis rate of mulberroside A is greater than or equal to 60%, preferably greater than or equal to 70%, more preferably greater than or equal to 80%, and most preferably greater than or equal to 90%.
In another preferred embodiment, in step (S2), the enzymolysis rate of mulberroside a is 60-97%, preferably 70-96%,80-95%.
In another preferred example, in the step (S2), the enzymatic treatment is performed in an aqueous system.
In another preferred embodiment, the solvent of the aqueous phase system is water, or a water/ethanol mixed solvent with an ethanol content of less than or equal to 10% (preferably less than or equal to 5wt%, more preferably less than or equal to 1 wt%).
In another preferred example, in step (S2), the relative increase of the oxidized resveratrol in the enzymolysis product is more than or equal to 300%, preferably more than or equal to 400%, more preferably more than or equal to 500%, and most preferably more than or equal to 600% compared with the raw material containing mulberroside a before enzymolysis.
In another preferred embodiment, in step (S2), the relative increase of oxyresveratrol is 50-2500%, preferably 100-2000%, more preferably 500-2000%.
In another preferred example, in step (S2), the concentration of oxyresveratrol in the enzymolysis product is greater than or equal to 0.15mg/g, preferably greater than or equal to 0.30mg/g, and preferably greater than or equal to 0.50mg/g.
In another preferred example, in the step (S2), the concentration of the oxyresveratrol in the enzymolysis product is 0.10-0.80 mg/g, preferably 0.2-0.7mg/g, preferably 0.3-0.6mg/g.
In another preferred example, in step (S2), the concentration of mulberroside A in the enzymolysis product is less than or equal to 0.20mg/g, preferably less than or equal to 0.15mg/g, preferably less than or equal to 0.10mg/g.
In another preferred example, in step (S2), the concentration of mulberroside a in the enzymatic hydrolysis product is 0.05-0.20mg/g, preferably 0.06-0.15mg/g, preferably 0.08-0.10mg/g.
In another preferred embodiment, before the enzymolysis, the concentration of mulberroside A in the raw material containing mulberroside A is 0.30-2.00mg/g, preferably 0.40-1.80mg/g.
In another preferred example, the concentration of the oxyresveratrol in the raw material containing the mulberroside A before the enzymolysis treatment is less than or equal to 0.10mg/g, preferably less than or equal to 0.08mg/g, and preferably less than or equal to 0.06mg/g.
In another preferred embodiment, the raw material containing mulberroside A is water extract, ethanol extract or ethanol/water extract of mulberry twig or cortex mori radicis medicinal material.
In another preferred example, the raw material containing mulberroside a is a plant extract, preferably an extract of a plant of the family moraceae.
In another preferred embodiment, the extract comprises: root, stem, leaf, fruit extracts.
In another preferred embodiment, the plant extract comprises: ramulus Mori extract, cortex Mori extract, or a combination thereof.
In another preferred embodiment, the raw material containing mulberroside A is an extract of a medicinal material of mulberry twig or cortex mori radicis.
In another preferred embodiment, in step (S2), the ratio (E1/W1) of the amount of beta-glucanase E1 to the weight W1 of mulberroside A is 02 to 25, preferably 6 to 20, more preferably 6 to 15, such as about 10.
In another preferred embodiment, in step (S2), the enzymolysis time is 0.5-3 hours, preferably 1-2 hours.
In another preferred example, the method further comprises the steps of:
and (S3) separating the oxyresveratrol from the enzymolysis products subjected to enzymolysis treatment in the step (S2) to obtain a separated crude oxyresveratrol product.
In another preferred example, the method further comprises the steps of:
(S4) refining and/or drying the separated crude oxyresveratrol product.
In another preferred embodiment, the separation is carried out by using macroporous adsorption resin to separate the oxyresveratrol.
In another preferred example, the macroporous resin is of the following types: AB-8, D101, DM301, or combinations thereof.
In another preferred example, the conditions for purifying the macroporous adsorption resin comprise: sample loading, water washing, 30-85% mass percent ethanol and the like. In another preferred example, in the step (S2), the enzymatic hydrolysis is performed with β -glucanase to obtain an enzymatic hydrolysate (or enzymatic hydrolysate) containing oxidized resveratrol.
In another preferred example, in the step (S3), the oxyresveratrol is separated from the enzymatic hydrolysate.
In another preferred example, the method further comprises:
adding the prepared oxyresveratrol as antioxidant or whitening additive into final product.
In a second aspect of the present invention, there is provided an oxyresveratrol prepared by the method of claim 1.
In a third aspect of the invention, there is provided a use of a beta-glucanase for enzymatic hydrolysis of mulberroside a, thereby converting mulberroside a into oxyresveratrol, or
The beta-glucanase is used to prepare an enzyme preparation for enzymatic hydrolysis of mulberroside a, thereby converting mulberroside a into oxyresveratrol.
It is to be understood that within the scope of the present invention, the above-described features of the present invention and those specifically described below (e.g., in the examples) may be combined with each other to form new or preferred embodiments. Not to be reiterated herein, but to the extent of space.
Drawings
FIG. 1 shows the chemical structural formula of mulberroside A.
Figure 2 shows the chemical structural formula of oxyresveratrol.
Figure 3 shows a process flow diagram of the present invention.
FIG. 4 shows a schematic enzymatic hydrolysis diagram of the present invention.
FIG. 5 shows the effect of different enzymes on the zymohydrolysis rate of mulberroside A and the increased amount of oxyresveratrol.
FIG. 6 shows a HPLC check chart of the enzymatic component content of the beta-glucanase of the present invention.
FIG. 7 shows the effect of different enzymatic hydrolysis times on the enzymatic hydrolysis rate of mulberroside A and the increased amount of oxyresveratrol.
FIG. 8 shows the effect of different enzyme addition levels on the zymolysis rate of mulberroside A and the increase of oxyresveratrol.
FIG. 9 is a graph showing the effect of the extracts prepared according to the present invention on inhibiting tyrosinase.
FIG. 10 shows that the extract prepared by the present invention is effective in scavenging DPPH (1, 1-diphenyl-2-picrylhydrazyl) radicals.
Detailed Description
The inventor provides a preparation method and application for improving the content of oxyresveratrol through extensive and intensive research and a large number of screening and tests. The invention unexpectedly discovers an enzymatic biotransformation method which can obviously improve the preparation content of oxyresveratrol. The invention also unexpectedly discovers that the highest conversion rate of the oxyresveratrol can be obtained by using the method for enzymolysis of mulberroside A by beta-glucanase. The present invention has been completed on the basis of this finding.
Experiments show that the method can effectively convert mulberroside A in raw materials such as mulberry twigs or white mulberry barks into the oxyresveratrol, and the increase of the oxyresveratrol is up to more than 2000%.
Mulberry bark glycoside A
Mulberroside A is dihydroxy stilbene compound (also called quinoa oxide), mainly exists in Moraceae and Morus plants, and has the following chemical structural formula (shown in figure 1):
in comparison with oxyresveratrol (see fig. 2), mulberroside a has two more glycosyl groups connected by glycosidic bonds.
Mulberroside A is inferior to resveratrol in oxidation resistance and tyrosinase activity inhibition, especially in tyrosinase activity inhibition. The literature reports that the IC50 value of the mulberroside A on the tyrosinase is 53.6 mu M, while the IC50 value of the oxyresveratrol is only 0.49 mu M, and the difference between the two values is more than 100 times.
Oxyresveratrol
Oxyresveratrol, chemically known as 2,4,3',5' -tetrahydroxystilbene, is a stilbene substance derived from stilbene, and is mainly present in plants of Morus and Artocarpus. The chemical structural formula is as follows:
pharmacological research shows that oxyresveratrol has strong inhibition effect on tyrosinase activity, thereby inhibiting melanin generation. In recent years, a great deal of research shows that oxyresveratrol is a dietary functional compound with the most promising effects of resisting browning, whitening and the like, and an oral medicament or related food thereof is safe and low in toxicity.
The oxyresveratrol has the characteristics of small toxic and side effect, large market demand, low content in plants, complex extraction process, narrow source and the like, so that the price is high, and the development and the utilization of cosmetics, natural medicines, health-care foods and functional beverages are severely restricted.
Preparation method
In the invention, a method for preparing a product with high content of oxyresveratrol is provided. Typically, the method of the invention comprises the steps of:
(S1) providing a raw material containing mulberroside A;
(S2) carrying out enzymolysis on the raw material containing mulberroside A by using beta-glucanase, thereby converting the mulberroside A into oxidized resveratrol;
(S3) separating the oxyresveratrol from the enzymolysis products subjected to enzymolysis treatment in the step (S2) to obtain a separated crude oxyresveratrol product;
(S4) refining and/or drying the separated crude oxyresveratrol product so as to obtain a product containing high-content oxyresveratrol.
In a preferred embodiment, the invention provides a preparation method for preparing a product containing high-content oxyresveratrol, which comprises the following steps:
(i) Extraction: pulverizing ramulus Mori or cortex Mori into coarse powder, adding alcohol/water mixed solvent (such as 60-80% ethanol water solution), extracting (for example, extracting under reflux at normal pressure for 1-3 times (each for 0.5-2 hr or about 1 hr)), mixing extractive solutions, filtering, and concentrating to obtain ethanol extract;
(ii) Enzymolysis: measuring the content of the mulberroside A in the ethanol extract by using HPLC, and then adding 50-2000% (the ratio (E1/W1) of the dosage E1 of the beta-glucanase to the weight W1 of the mulberroside A is 2-20, preferably 6-15, more preferably 8-12) of the beta-glucanase, the xylanase, the pectinase or the cellulase or the combination thereof according to the total mass of the mulberroside A in the ethanol extract for enzymolysis according to the detection result; the enzymolysis time is usually 0.5 h-3 h, and the enzymolysis filtrate is obtained after filtration;
(iii) Purifying with macroporous adsorption resin: loading the enzymolysis filtrate on macroporous adsorption resin, wherein the representative resin types comprise: AB-8, D101 or DM301 or the like, and then eluting with an eluent to obtain an analytic solution containing oxyresveratrol; representative eluents in this step include (but are not limited to): an ethanol aqueous solution with the mass percentage concentration of 30-85%; furthermore, in this step, washing with water may be optionally performed after the loading;
(iv) And (3) drying: and (3) concentrating and/or drying the resolving liquid to obtain a product containing the oxyresveratrol. Typically, the concentration is carried out under reduced pressure at 40-60 ℃, the vacuum degree is less than 20 Pa, and the drying is freeze-drying at a freezing temperature of-70-50 ℃.
In another preferred example, in the step (S2) or the enzymolysis step, β -glucanase is added for enzymolysis.
In another preferred embodiment, the beta-glucanase is used in an amount E1 to the mulberry glycoside A weight W1 ratio (E1/W1) of 0.5-20, preferably about 2-20 or 6-15, more preferably 6-12, such as about 10.
In another preferred embodiment, in the present invention, the enzymolysis time is not particularly limited, and is usually 0.5 to 3 hours, such as 1h to 2h or 1 to 3h, preferably about 2h.
Composition containing oxyresveratrol and application thereof
The oxyresveratrol has strong tyrosinase inhibition and antioxidant activity, so that the oxyresveratrol can be widely applied to cosmetics, natural medicines, health-care products and the like.
The invention also provides application of the oxyresveratrol prepared by the method. Representative applications include (but are not limited to): cosmetic compositions or products, pharmaceutical compositions or medicaments, dietary supplements, etc.
Taking a cosmetic composition as an example, the cosmetic composition comprises the oxyresveratrol disclosed by the invention; and a cosmetically acceptable carrier. Typically, the oxyresveratrol of the present invention can be prepared into cosmetic compositions by conventional methods, representative cosmetics include (but are not limited to): solid, semi-solid, or liquid dosage forms, such as solutions, gels, creams, lotions, sprays, ointments, creams, pastes, cakes, powders, patches, and the like.
The oxyresveratrol can also be used for preparing pharmaceutical compositions. The pharmaceutical composition comprises the oxyresveratrol disclosed by the invention; and a pharmaceutically acceptable carrier. The dosage form of the pharmaceutical composition of the present invention is not particularly limited, and representative dosage forms include (but are not limited to): such as ointment, cream, gel, paste, patch, etc. The drug can be prepared by a generally known preparation technique, and a suitable pharmaceutical additive can be added to the drug.
Examples of the pharmaceutical additives include excipients, binders, disintegrating agents, lubricants, flow aids, suspending agents, emulsifiers, stabilizers, warming (wetting) agents, preservatives, solvents, solubilizers, preservatives, flavoring agents, sweeteners, dyes, flavors, propellants and the like, and these pharmaceutical additives may be selected and added in an appropriate amount within a range not affecting the effect of the present invention.
Other components commonly used in cosmetics or medicines, for example, film-forming agents, oil-soluble gelling agents, organically modified clay minerals, resins, moisturizing agents, preservatives, antibacterial agents, perfumes, salts, antioxidants, pH adjusting agents, chelating agents, cooling agents, anti-inflammatory agents, skin beautifying components (whitening agents, cell active agents, skin roughness improving agents, blood circulation promoters, skin astringents, anti-lipid leakage agents, etc.), vitamins, amino acids, nucleic acids, hormones, inclusion compounds, and the like may be added to the cosmetics or medicines of the present invention within a range that does not interfere with the effects of the present invention.
Suitable oil-soluble gelling agents include (but are not limited to): metal soaps such as aluminum stearate, magnesium stearate, and zinc myristate; amino acid derivatives such as N-lauroyl-L-glutamic acid, α, γ -di-N-butylamine, and the like; cyclodextrin fatty acid esters such as cyclodextrin palmitate, cyclodextrin stearate, and cyclodextrin 2-ethylhexanoate palmitate; sucrose fatty acid esters such as sucrose palmitate and sucrose stearate; benzylidene derivatives of sorbitol such as monobenzylidene sorbitol and dibenzylidene sorbitol; one or two or more kinds of gelling agents such as an organically modified clay mineral such as dimethylbenzyl dodecylammonium montmorillonite clay or dimethyl octacosyl ammonium montmorillonite clay may be used as required.
Suitable humectants include, but are not limited to: glycerin, sorbitol, propylene glycol, dipropylene glycol, 1, 3-butylene glycol, glucose, xylitol, maltitol, polyethylene glycol, hyaluronic acid, chondroitin sulfate, pyrrolidone carboxylate, polyoxyethylene methyl glucoside, polyoxypropylene methyl glucoside, and the like.
Suitable antimicrobial preservatives include (but are not limited to): alkyl parabens, benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, phenoxyethanol, and the like, and antibacterial agents such as: benzoic acid, salicylic acid, carbolic acid, sorbic acid, alkyl parabens, parachloro-metacresol, hexachlorophene, benzalkonium chloride, chlorhexidine chloride, trichloro-carbanilide, triclosan, a photosensitizer, phenoxyethanol, and the like.
Suitable antioxidants include (but are not limited to): tocopherol, butyl hydroxy anisole, dibutyl hydroxy toluene, phytic acid and the like, and pH regulators comprise: lactic acid, citric acid, glycolic acid, succinic acid, tartaric acid, dl-malic acid, potassium carbonate, sodium bicarbonate, ammonium bicarbonate, and the like, as chelating agents, alanine, sodium ethylenediaminetetraacetate, sodium polyphosphate, sodium metaphosphate, phosphoric acid, and the like, as cooling agents: l-menthol, camphor, etc., and the anti-inflammatory agents include: allantoin, glycyrrhetinic acid, glycyrrhizic acid, tranexamic acid, and Azulene (Azulene).
Representative skin beautifying ingredients include (but are not limited to): whitening agent such as placenta extract, arbutin, glutathione, and herba Saxifragae extract; cell activator such as Lac Regis Apis, photosensitizer, cholesterol derivative, calf blood extractive solution, etc.; an agent for improving rough skin; blood circulation promoters such as valerian nonanoate, benzyl nicotinate, beta-butoxyethyl nicotinate, capsaicin, zingerone, cantharides tincture, ichthammol, caffeine, tannic acid, alpha-borneol, tocopherol nicotinate, inositol hexanicotinate, cyclamate, cinnarizine, tolazoline, acetylcholine, verapamil, cepharanthin, and gamma-oryzanol; skin astringents such as zinc oxide and tannic acid; the vitamins are: vitamin A oil, rosin oil, acetic acid rosin oil, palmitic acid rosin oil, and the like; vitamin B2 compounds such as riboflavin, riboflavin butyrate, and flavin adenine nucleotide; vitamin B6 compounds such as pyridoxine hydrochloride, pyridoxine dicaprylate, and pyridoxine tripalmitate; vitamin C compounds such as L-ascorbic acid and L-ascorbyl dipalmitate; vitamin D compounds such as ergocalciferol and cholecalciferol; vitamin E compounds such as alpha-tocopherol, beta-tocopherol, gamma-tocopherol, dl-alpha-tocopherol acetate, dl-alpha-tocopherol nicotinate, dl-alpha-tocopherol succinate, and the like; vitamin H; a vitamin P; nicotinic acids such as nicotinic acid, benzyl nicotinate and nicotinamide; pantothenic acids such as calcium pantothenate, D-panthenol, panthenyl ethyl ether, and acetyl panthenyl ethyl ether; biotin, and the like.
Suitable amino acids include (but are not limited to): glycine, valine, leucine, isoleucine, serine, threonine, phenylalanine, arginine, lysine, aspartic acid, glutamic acid, cystine, cysteine, methionine, tryptophan, etc., nucleic acids include deoxyribonucleic acid, etc., and hormones include estradiol, vinylestradiol, etc.
In the present invention, preferable examples of the cosmetic include: skin care cosmetics, hair care cosmetics, color cosmetics, and ultraviolet protection cosmetics. For example, there are hair care products such as shampoo, hair conditioner, hair essence, hair mask, etc.; basic cosmetics such as lotion, cream, lotion, sunscreen cream, facial mask material, facial cleanser, essence, etc.; makeup cosmetics such as foundation, powdery, blush, and the like.
In the present invention, the form of the cosmetic product is not particularly limited, and may be a liquid, emulsion, cream, solid, paste, gel, powder, multi-layer, mousse (mousse), spray, or the like.
The main advantages of the invention include:
(1) The invention carries out biological transformation by an enzyme method for the first time, and carries out high-efficiency transformation on mulberroside A which has higher content and wider distribution in plants to make the mulberroside A become oxyresveratrol which has lower content and extremely strong tyrosinase activity inhibition; the zymohydrolysis rate of the mulberroside A reaches more than 50 percent, and can reach 93.56 percent at most.
(2) The extraction and elution solvents of the invention are ethanol, and the solvents are safe, nontoxic, low in cost and recyclable.
(3) In the invention, the extract containing the mulberroside A is used for enzymolysis, the raw materials can be extracted by heating and refluxing, the preparation method is simple and convenient, the equipment requirement is low, the cost is low, and the method is suitable for industrial production.
(4) The invention uses macroporous resin for purification, the cost of the resin is lower, and the resin is simple and convenient to regenerate.
(5) Compared with the extract of mulberry twigs or white mulberry barks before enzymolysis, the high-purity oxyresveratrol product has stronger tyrosinase inhibition effect, and can be used as an antioxidant additive (antioxidant) to be added into various products such as cosmetics and the like.
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out under conventional conditions or conditions recommended by the manufacturers. Unless otherwise indicated, percentages and parts are percentages and parts by weight.
Material
Beta-glucanase: the enzyme activity is 700 EGU/g.
Cellulase: the enzyme activity is 700 EGU/g.
Xylanase: microbial source, and enzyme activity of 500 FXUs/g.
And (3) pectinase: the microbial source and the enzyme activity are 8600 PGNU/g.
The above enzymes are all commercially available products.
Example 1
Preparation of Oxyresveratrol (sample No. 1)
The invention utilizes a biotransformation preparation method to improve the content of oxyresveratrol, and comprises the following steps:
(1) Extraction: taking cortex mori radicis medicinal materials, grinding the cortex mori radicis medicinal materials into coarse powder, and mixing the coarse powder and the coarse powder according to a primary material-liquid ratio of 1:10 (g: mL), the ratio of the second feed to the liquid is 1:10 (g: mL) are respectively added with 60% (v/v) ethanol, reflux extraction is carried out twice for 1h each time, reduced pressure suction filtration and concentration are carried out, thus obtaining ethanol extract;
(2) Enzymolysis: measuring the content of mulberroside A in the ethanol extract by HPLC, adding enzyme according to 400% (w/w) of the total mass of the mulberroside A, carrying out enzymolysis in an aqueous solution for 2h, and carrying out vacuum filtration to obtain an enzymolysis filtrate; determining contents of mulberroside A and oxyresveratrol before and after enzymolysis in the ethanol extract by using HPLC;
(3) Purifying with macroporous adsorption resin: loading the enzymolysis filtrate on DM301 macroporous adsorption resin for purification, and collecting an analytic solution;
(4) And (3) drying: the analysis solution was concentrated under reduced pressure and freeze-dried to obtain sample No.1.
Examples 2 to 4
Preparation of Oxyresveratrol (samples No.2, 3 and 4)
Example 1 was repeated, with the only difference that: samples No.2, 3 and 4 were prepared by replacing the beta-glucanase with cellulase (example 2), xylanase (example 3) and pectinase (example 4), respectively (the amounts of enzymes were the same as in example 1).
The experimental results of examples 1 to 4 are shown in table 1 and fig. 5 to 6:
TABLE 1 Effect of different enzymes on the conversion of mulberroside A
As shown in Table 1 and FIG. 5, most enzymes did not efficiently convert mulberroside A into oxyresveratrol, and some even resulted in a decrease in the content of oxyresveratrol (e.g., xylanase of example 3). This suggests that, although the content of mulberroside a is reduced to some extent by 20-30% (enzymatic hydrolysis rate) when various enzymes (cellulase, xylanase and pectinase) are used for treatment, the content of the desired oxyresveratrol in the enzymatic hydrolysis product is not increased basically by an extent of-6% to 3%.
Unexpectedly, the beta-glucanase has extremely excellent capability of converting the mulberroside A, and the zymohydrolysis rate of the mulberroside A is as high as about 80 percent, which is about 20.6 times of the conversion capability of cellulase, and which is about 31.0 times of the conversion capability of pectinase.
Furthermore, unexpectedly, when the beta-glucanase is adopted, the content of the oxidized resveratrol in the enzymolysis products is obviously increased, and the increase amplitude is about 64 percent.
Examples 5 to 7
Preparation of Oxyresveratrol (samples No.5, 6 and 7)
Example 1 was repeated, differing only in that: replacing the enzyme adding amount by 1000% of the total mass of the mulberroside A in the ethanol extract, and replacing the enzymolysis time by 1h (embodiment 5), 2h (embodiment 6) and 3h (embodiment 7) respectively; in order to increase the increase amount of oxyresveratrol, the raw materials with higher content of mulberroside A are selected for carrying out examples 5-7. Thus, sample Nos. 5, 6 and 7 were obtained, respectively.
The experimental results of examples 5 to 7 are shown in table 2 and fig. 7:
TABLE 2 Effect of enzymolysis time on mulberroside A conversion
As can be seen from table 2 and fig. 7, the optimum conversion effect of mulberroside A is achieved when the enzymolysis time is 3 hours, the enzymolysis rate can reach 95.74%, and the increase of oxyresveratrol is up to 1896.55%.
However, the enzymolysis time of 3h is not much different from that of 2h, and 2h can be selected as an appropriate enzymolysis time in consideration of cost.
Examples 8 to 14
Preparation of Oxyresveratrol (sample Nos. 8 to 14)
Example 1 was repeated, with the only difference that: sample nos. 8, 9, 10, 11, 12, 13 or 14 were prepared by replacing the enzyme addition amount with one of 50% (example 8), 100% (example 9), 150% (example 10), 200% (example 11), 600% (example 12), 1000% (example 13) or 2000% (example 14), respectively, of the total mass of mulberroside a in the ethanol extract.
The experimental results of examples 8 to 14 are shown in table 3 and fig. 8:
TABLE 3 Effect of enzyme addition on mulberroside A conversion
As can be seen from Table 3 and FIG. 8, when the ratio (E1/W1) of the amount of beta-glucanase E1 to the amount of mulberroside A W1 was 0.5-2, the amount of produced oxyresveratrol was not significantly increased (the increase was varied from 16-23%).
However, unexpectedly, when the E1/W1 ratio is 6 (i.e., 600%), the amount of oxyresveratrol produced is significantly increased; when the ratio (E1/W1) of the dosage E1 of the beta-glucanase to the weight W1 of the mulberroside A is 6-10, the generation amount of the oxyresveratrol is slowly increased. When the ratio is 10, the maximum production is reached; when the ratio (E1/W1) of the dosage E1 of the beta-glucanase to the weight W1 of the mulberroside A is 11-20, although the enzymolysis rate of the mulberroside A is gradually increased and reaches up to 94.22 percent when the ratio is 20, the generation amount of the oxyresveratrol is slowly reduced.
Based on the production of oxyresveratrol and material cost, a suitable beta-glucanase may be selected having a ratio of E1 to W1 (E1/W1) of the amount of mulberroside A in the ethanol extract of 8-12 (e.g., 10), i.e., an enzyme addition amount of 800-1200% (e.g., about 1000%) of the total mass of mulberroside A in the ethanol extract.
Example 15
Inhibition of tyrosinase efficacy
The tyrosinase inhibition efficacy test was performed on the cortex mori radicis extract (sample No. 13) prepared in example 13, and the specific implementation manner is as follows:
15.1 test reagent and preparation method
15.1.1 PBS buffer (0.1M, pH 6.8)
Reagent A: weighing 7.16 g of Na 2 HPO 4 •12H 2 O is diluted to 100mL by distilled water;
and (3) reagent B: 3.12 g NaH are weighed out 2 PO 4 •2H 2 O is diluted to 100mL by distilled water; or weighing KH 2 PO 4 2.72 g, metering to 100 mL;
and uniformly mixing 49 mL of the reagent A and 51 mL of the reagent B, and diluting twice (adding 100mL of distilled water) to obtain the reagent.
15.1.2 L-tyrosine solution
Accurately weighing 4.5 mg of L-tyrosine, and diluting to 50 mL with PBS buffer solution (1.1).
15.1.3 Tyrosinase solution
Accurately weighing 5mg of tyrosinase, and adding 10 mL of PBS buffer solution (1.1) by using a pipette gun to obtain the tyrosinase-containing liquid.
15.1.4 1% beta-arbutin alcohol solution (Positive control)
Weighing 0.1 g of beta-arbutin, and diluting to 10 mL with 10% ethanol solution to obtain the final product.
15.2 Test method
15.2.1 Test sample preparation
The detection was carried out by preparing a solution of the appropriate concentration with PBS buffer (1.1).
15.2.2 Detection process
Control group: adding 750 μ L L-tyrosine solution into 250 μ L PBS buffer solution, and keeping the temperature at 37 deg.C for 30min; adding 50 μ L tyrosinase solution, reacting at 37 deg.C for 30min, and measuring absorbance value at 450 nm.
Experimental groups: respectively taking 25 μ L, 50 μ L, 125 μ L and 250 μ L of the solution to be detected, supplementing to 250 μ L with PBS buffer solution, adding 750 μ L of L-tyrosine solution, and keeping the temperature at 37 deg.C for 30min; adding 50 μ L tyrosinase solution, reacting at 37 deg.C for 30min, and measuring absorbance at 450 nm.
Blank group: respectively taking 25 μ L, 50 μ L, 125 μ L and 250 μ L of the solution to be detected, supplementing to 250 μ L with PBS buffer solution, adding 750 μ L of L-tyrosine solution, and keeping the temperature at 37 deg.C for 30min; 50. Mu.L of PBS buffer was added, and the reaction was carried out at 37 ℃ for 30min, and the absorbance at 450 nm was measured.
Positive control group: respectively taking 25 μ L, 50 μ L, 125 μ L and 250 μ L of arbutin alcohol solution, supplementing to 250 μ L with PBS buffer solution, adding 750 μ L of L-tyrosine solution, and keeping at 37 deg.C for 30min; adding 50 μ L tyrosinase solution, reacting at 37 deg.C for 30min, and measuring absorbance at 450 nm.
15.2.3 Test results
As shown in fig. 9, under the test conditions, the IC50=4.893mg/mL of the positive control β -arbutin and the IC50=1.365 μ g/mL of the cortex mori radicis extract (sample No. 13) are 3585 times of the positive control, and have stronger tyrosinase inhibitory effect.
Wherein A0 is the absorbance value of a control group; a1 is the absorbance value of an experimental group; a2 is blank absorbance value; the positive control group A2 was 0.
Example 16
DPPH radical scavenging Activity
The DPPH free radical scavenging test was performed on the cortex mori extract (sample No. 13) prepared in example 13, in the following manner:
16.1 Test reagent and preparation method
16.1.1 DPPH methanol solution
7.88g of DPPH was weighed out, and the volume was adjusted to 100mL with methanol, and the mixture was stored in a dark place.
16.1.2 Vc methanol solution (Positive control)
10mg of ascorbic acid was weighed out and made up to 100mL with methanol.
16.2 Test method
16.2.1 Test sample preparation
The detection can be carried out by preparing the solution into a solution with a proper concentration by using a 50% methanol solution.
16.2.2 Detection process
Control group: taking 0.025mL, 0.05mL, 0.1mL, 0.2mL, 0.4mL and 0.5mL samples and a deep-well plate respectively, supplementing the samples to 0.5mL by distilled water, adding 2.0mL of DPPH methanol solution, mixing the samples uniformly, placing the mixture in a dark place for 30min, taking 0.2mL and a 96-well plate, and measuring the absorbance at the position of 520nm by using a microplate reader.
Blank group: taking 0.025mL, 0.05mL, 0.1mL, 0.2mL, 0.4mL and 0.5mL samples and a deep-well plate respectively, supplementing to 0.5mL with distilled water, adding 2.0mL methanol solution, mixing uniformly, placing in the dark for 30min, taking 0.2mL and a 96-well plate, and measuring the absorbance at 520nm by using an enzyme-labeled instrument.
Positive control group: adding 0.025mL, 0.05mL, 0.1mL, 0.2mL, 0.4mL and 0.5mL of Vc methanol solution into a deep-well plate respectively, adding distilled water to 0.5mL, adding 2.0mL of DPPH methanol solution, mixing uniformly, standing in the dark for 30min, taking 0.2mL and a 96-well plate, and measuring the absorbance at 520nm by using a microplate reader.
Control group: adding 0.5mL of distilled water and 2.0mL of DPPH methanol solution, mixing, standing in the dark for 30min, taking 0.2mL of the mixture and a 96-well plate, and measuring the absorbance at 520nm by using an enzyme-labeling instrument.
16.2.3 Test results
As shown in fig. 10, under the test conditions, the maximum DPPH clearance of the cortex mori radicis extract (sample No. 13) was 95% or more, with an IC50=138.86 μ g/mL; in a whole view, although the DPPH clearance of the extract with the oxyresveratrol content of 2.8 percent is lower than that of ascorbic acid with the same concentration, the concentration and the DPPH clearance have a better linear relation and have a certain antioxidation effect.
Wherein A0 is the absorbance value of the control group; a1 is an absorbance value of an experimental group; a2 is blank absorbance value; the positive control group A2 was 0.
All documents referred to herein are incorporated by reference into this application as if each were individually incorporated by reference. Furthermore, it should be understood that various changes or modifications of the present invention can be made by those skilled in the art after reading the above teachings of the present invention, and these equivalents also fall within the scope of the appended claims of the present application.
Claims (10)
1. A preparation method of oxyresveratrol is characterized by comprising the following steps:
(S1) providing a raw material containing mulberroside A;
(S2) carrying out enzymolysis treatment on the raw material containing mulberroside A by using beta-glucanase to convert the mulberroside A into oxidized resveratrol so as to obtain an enzymolysis product:
wherein, in the step (S2), the ratio of the dosage E1 of the beta-glucanase by weight to the weight W1 of the mulberroside A is 6-20.
2. The method according to claim 1, wherein the enzymatic hydrolysis rate of mulberroside A in step (S2) is at least 90%.
3. The method of claim 1, wherein in step (S2), the relative increase of the oxidized resveratrol in the enzymatic hydrolysis product is greater than or equal to 1000% compared to the mulberroside A-containing feedstock prior to enzymatic hydrolysis.
4. The method of claim 1, wherein the mulberroside a-containing material is an aqueous, ethanol, or ethanol/aqueous extract of mulberry twig or cortex mori radicis.
5. The method according to claim 1, wherein in step (S2), the ratio of the amount of β -glucanase E1 to the amount of mulberroside a W1 (E1/W1) is 6 to 15.
6. The method according to claim 1, wherein the concentration of mulberroside A in the raw material containing mulberroside A before the enzymatic hydrolysis treatment is 0.30-2.00mg/g.
7. The method according to claim 1, wherein in step (S2), the concentration of mulberroside a in the enzymatic hydrolysate is 0.10mg/g or less; and/or, in the enzymolysis product, the concentration of the oxyresveratrol is more than or equal to 0.30mg/g.
8. The method of claim 1, wherein the method further comprises the steps of:
and (S3) separating the oxyresveratrol from the enzymolysis product subjected to enzymolysis treatment in the step (S2) to obtain a separated oxyresveratrol crude product.
9. The method of claim 8, wherein said separating comprises separating the oxidized resveratrol using a macroporous adsorbent resin.
10. The method of any one of claims 1-9, further comprising:
adding the prepared oxyresveratrol as antioxidant or whitening additive into final product.
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