CN113151373B - Preparation method and application of sucrose monoester with antibacterial and antitumor activities - Google Patents
Preparation method and application of sucrose monoester with antibacterial and antitumor activities Download PDFInfo
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- 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
- C12P19/00—Preparation of compounds containing saccharide radicals
- C12P19/12—Disaccharides
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3562—Sugars; Derivatives thereof
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
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- 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 invention particularly relates to a preparation method and application of sucrose monoester with antibacterial and antitumor activities. The preparation method comprises the following steps: in a solvent system of anhydrous tertiary butanol and anhydrous pyridine, sucrose and fatty acid vinyl ester with a molar ratio of 1 (3-5) are reacted under the action of enzyme to obtain a sucrose monoester mixture, and the sucrose monoester is obtained by purification. The invention adopts the mixture of the anhydrous tertiary butanol and the anhydrous pyridine as the solvent, the enzyme has higher activity in the solvent, and can promote the conversion of reactants, thereby improving the yield, and the prepared sucrose monoester has better foamability and foamability stability, excellent emulsification and antibacterial effects and a certain activity of anti-tumor cells.
Description
Technical Field
The invention belongs to the field of foods, and particularly relates to a preparation method and application of sucrose monoester with antibacterial and antitumor activities.
Background
Sugar esters are nonionic biosurfactants composed of hydrophilic glycosyl groups and hydrophobic fatty acid chains, have excellent characteristics of biodegradability, biocompatibility, no toxicity, no smell, no irritation and the like, and have been widely used in industries such as foods, cosmetics, pharmaceuticals and the like. Sucrose fatty acid esters are currently most widely used among all sugar esters. Among these sucrose esters of different carbon chain lengths, the long chain fatty acid monoester has better water solubility, the most widely used and the most promising market prospect.
At present, the synthesis of sucrose esters in industrial production mainly adopts a chemical synthesis method, but has various disadvantages such as harsh reaction conditions, poor specificity, occurrence of side reactions and generation of various forms of derivatives, serious environmental pollution, high cost, low yield and the like. In recent years, with the development of nonaqueous phase enzymology, enzymatic synthesis has received more attention due to the characteristics of high specificity, strong specificity and the like. Enzymatic synthesis of sugar esters has proved to be superior to chemical methods, but the enzymatic synthesis has the problems of environmental pollution, reduced enzyme activity and the like, resulting in lower product yields.
The chinese patent CN1389450a discloses a method for producing sucrose fatty acid ester by one-step method and its use, the method is to put sucrose, vegetable oil and alkali metal catalyst into a reaction kettle together, stir to make solid-liquid reaction, then discharge and package. The obtained product can be used as an antifoaming agent in the process of boiling sugar, papermaking and wastewater purification engineering. The method avoids the use of polar solvents, has simple production process and low cost, but because vegetable oil is used as a source of fatty acid, the final product inevitably contains glyceride byproducts besides sucrose ester, so that the purity of the sucrose ester is reduced, the original emulsifying property of the sucrose ester is deteriorated, and the application range of the sucrose ester is greatly limited, especially in the food field (for example, the sucrose ester cannot be used as a foaming agent or a whipping agent in foods such as cakes). Furthermore, the patent is not directed to the use of sucrose esters for antibacterial and antitumor applications.
Chinese patent publication No. CN111094312a discloses a method for preparing sucrose ester. The patent adopts a solvent-free method, and hydrogenated palm oil and sucrose are subjected to transesterification under the action of a catalyst (preferably potassium carbonate) to obtain a sucrose ester crude product. When an emulsifier (preferably Mitsubishi S-570 sucrose ester of Japan) is still present in the reaction system, the sucrose ester yield can reach 40.49%. However, the use of hydrogenated palm oil (essentially triglycerides) necessarily results in the end product containing glyceride by-products, thus significantly limiting the purity and monoester content of sucrose esters and thus severely limiting the range of applications thereof. Furthermore, the patent is not directed to the use of sucrose esters for antibacterial and antitumor applications.
Chinese patent publication No. CN103396460B discloses a method for preparing sucrose ester. The method uses alkaline earth metal oxide (namely calcium oxide) which is common in industry as a solid catalyst to catalyze fatty acid methyl ester and sucrose to generate sucrose ester through transesterification. The solid catalyst used in the method cannot remain in the product and can be reused, the purity of the sucrose ester can reach more than 98%, but the monoester content in the product is not clear, and whether the sucrose ester has better emulsifying property cannot be known. Furthermore, the patent is not directed to the use of sucrose esters for antibacterial and antitumor applications.
Chinese patent publication No. CN103087118B discloses a method for purifying sucrose esters. The method comprises the steps of dissolving a sucrose ester crude product in an organic solvent (ethyl acetate, butanone or n-butanone) which is immiscible with water to obtain a sucrose ester crude product solution, and then dropwise adding a salt aqueous solution of an alkali earth metal/alkaline earth metal oxide (such as calcium chloride, magnesium chloride, barium chloride/calcium oxide, magnesium oxide, barium oxide and the like) under stirring, so that fatty acid soaps in the sucrose ester crude product solution generate fatty acid alkali earth metal salts which are insoluble in the organic solvent and are removed; adding salt water (sodium chloride, potassium chloride, sodium sulfate or potassium sulfate aqueous solution), stirring, extracting, standing, separating lower water layer, stirring supernatant, cooling to 0-40deg.C to crystallize sucrose ester, collecting crystal, and drying to obtain sucrose ester product. The method uses a cooling crystallization process to remove unreacted fatty acid methyl ester and other raw materials, further improves the total ester content to 98 percent, but according to the implementation example provided by the method, the monoester content in the product is only 19.6 to 71.4 percent, and the monoester content still needs to be improved. Furthermore, the patent is not directed to the use of sucrose esters for antibacterial and antitumor applications.
The Chinese patent publication No. CN104004033B discloses a purification and separation method of sucrose ester, which comprises the steps of dispersing and dissolving a sucrose fatty acid ester crude product in an organic solvent A (ethyl acetate, butanone or n-butanol and a combination thereof), filtering and recovering sucrose to obtain a sucrose ester crude product solution, adding alkaline earth metal salt (magnesium sulfate, calcium chloride, barium chloride or a combination thereof) into the solution under stirring at 25-80 ℃ to carry out double decomposition reaction, and then carrying out solid-liquid separation at 5-80 ℃ to obtain filtrate A and solid B; washing the filtrate A with water, distilling to recover solvent, and drying to obtain sucrose ester product A; adding an organic solvent B into the solid B, extracting at 50-80 ℃, washing the obtained extract, distilling to recover the solvent, and drying to obtain a sucrose ester product B. The outstanding advantage of this process is the high product content and recovery, and the separation of sucrose monodiester is also accomplished to obtain products of different sucrose monoester content, according to the examples provided in this patent, the monoester content of the sucrose fatty acid esters is only up to 75.2%. This means that the monoester content of the product cannot be increased significantly by simply modifying the purification process without combining a better preparation process. Furthermore, the patent is not directed to the use of sucrose esters for antibacterial and antitumor applications.
Chinese patent application publication No. CN110891962a discloses a sucrose fatty acid ester, a preparation method, a quantitative analysis method and use thereof. In the method, sucrose, fatty acid methyl ester, a catalyst (preferably potassium carbonate) and a surfactant (preferably potassium stearate or Mitsubishi S-570 sucrose ester in Japanese) are added into a solvent (preferably N, N-dimethylformamide, namely DMF) for transesterification to obtain a crude product; the crude product is purified and separated by extraction and recrystallization to obtain sucrose fatty acid ester product, and the monoester content can reach 84-91% at maximum. Although this patent application claims that the sucrose esters it provides are useful for stabilizing emulsions, foaming, bacteriostasis or aging, there is no relevant data or examples in the patent application document to support the use of the products thereof in this regard. And it is known from the disclosure of this patent application that it claims fatty acid methyl ester raw materials for preparing sucrose esters, in fact, only two long chain fatty acid methyl esters of methyl stearate and methyl palmitate (C18 and C16) are included, and nothing is mentioned about an ultra-long chain fatty acid (methyl ester) that can enhance emulsifying, antibacterial properties and introduce potential anticancer activity. Furthermore, the patent is not directed to the use of sucrose esters for anti-tumor applications.
Chinese patent application publication No. CN103805653a discloses a method for synthesizing sucrose-6-ester by ultrasonic-assisted enzyme catalysis, which is suitable for industrial production. This method utilizes physical fields (ultrasound) to assist biocatalysis. The invention dissolves sucrose in a mixed solvent of dimethyl sulfoxide (DMSO)/tert-butyl (amyl) alcohol, and utilizes ultrasonic auxiliary lipase (Lipozyme TL IM, lipozyme TL100L or Lipozyme RM IM) to catalyze the sucrose and fatty acid vinyl ester to generate sucrose-6-ester. From the practical operation point of view, the method adopts ultrasonic to assist industrial production, needs to be additionally provided with large-scale ultrasonic equipment, and has higher purchase, operation and maintenance costs; the ultrasonic wave applied in the pretreatment of enzyme particles and the reaction process is required to strictly limit the sound intensity, the frequency and the treatment time, otherwise, the effect is not obvious due to insufficient ultrasonic treatment or the enzyme particles are broken and deactivated due to excessive pretreatment, which increase the control difficulty of the ultrasonic wave in actual production; the acoustic wave field generated by the large-scale ultrasonic equipment often has uneven conditions, so that the reaction efficiency is reduced, and the yield is reduced; finally, the generation of the ultrasonic field requires energy consumption, which would be considerable if mass production were carried out with a reaction time of up to 0.5-10 hours in this invention. In summary, the application of the ultrasonic reactor to large-scale industrial production instead of the traditional stirring mode is not mature enough at present.
In view of the foregoing, there is a need in the art to develop a new method for preparing and purifying sucrose fatty acid esters, which can obtain products with higher yield and purity of sucrose monoesters at lower production cost, and which has excellent antibacterial properties and potential health care (anti-tumor activity) in addition to excellent surface activity, foaming properties and emulsifying properties, so as to meet the high-end application requirements of the fields of high-grade foods, cosmetics, medicines, agriculture and the like.
Disclosure of Invention
In order to solve the defects and shortcomings in the prior art, the primary purpose of the invention is to provide a preparation method of sucrose monoester. The preparation method has high yield, and the prepared sucrose monoester has good foamability, excellent emulsifying effect, certain antibacterial effect and anticancer activity.
The second object of the present invention is to provide a sucrose monoester prepared by the above preparation method.
It is a further object of the present invention to provide the use of the sucrose monoesters described above.
The invention aims at realizing the following technical scheme:
the invention provides a preparation method of sucrose monoester, which comprises the following steps:
reacting sucrose and fatty acid vinyl ester under the action of enzyme to obtain a sucrose monoester mixture, and purifying to obtain sucrose monoester;
the fatty acid in the fatty acid vinyl ester is a fatty acid with 12-22 carbon atoms;
the mol ratio of the sucrose to the fatty acid vinyl ester is 1 (3-5);
the enzyme is an enzyme capable of catalyzing sucrose and organic acid vinyl ester to carry out transesterification reaction, and is preferably novelin lipase TLIM;
the solvent for the reaction is a mixed solvent of anhydrous lower alcohol and anhydrous pyridine, preferably a combination of anhydrous tertiary butanol and anhydrous pyridine.
In the invention, sucrose and fatty acid vinyl ester are subjected to irreversible transesterification in an organic solvent, and the specific process is shown in figure 1.
Preferably, the molar ratio of sucrose to fatty acid vinyl ester material is 1 (3-5), such as 1:3.1, 1:3.2, 1:3.3, 1:3.4, 1:3.5, 1:3.6, 1:3.7, 1:3.8, 1:3.9, 1:4.0, 1:4.1, 1:4.2, 1:4.3, 1:4.4, 1:4.5, 1:4.6, 1:4.7, 1:4.8, 1:4.9, etc., preferably 1:4.
Preferably, the temperature of the reaction is 30-60 ℃, e.g. 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56 ℃, 57, 58, 59, etc., preferably 40 ℃.
Preferably, the reaction time is 4-15 hours, such as 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 hours, etc., preferably 8 hours.
Preferably, the volume ratio of the anhydrous tertiary butanol to the anhydrous pyridine is (2-4): 3, e.g., 2.2:3, 2.4:3, 2.6:3, 2.8:3, 3:3, 3.2:3, 3.4:3, 3.6:3, 3.8:3, etc., preferably 1:1.
Preferably, the purification method is column chromatography, the mobile phase used is a mixed solvent combination containing dichloromethane and methanol, and the volume ratio of the two is (20-25): 3, such as 21:3, 22:3, 23:3, 24:3, etc., preferably 22:3.
The invention preferably adopts column chromatography to purify the reaction product, and has the advantages of simple operation, economy, large sample bearing capacity, good separation and purification effects and the like, thereby further improving the reaction yield.
More preferably, the column chromatography uses a silica gel column chromatography.
Preferably, the preparation method specifically comprises the following steps:
(1) Adding anhydrous tertiary butanol and pyridine with the volume ratio of (2-3) 3 and 3-5 equivalents of fatty acid vinyl ester into 1 equivalent of sucrose, adding novelin lipase TLIM, and reacting for 4-15h at the temperature of 30-60 ℃;
(2) And (3) performing column chromatography on the reaction product obtained in the step (1), and removing the solvent to obtain the sucrose monoester.
Preferably, the method for removing the solvent comprises vacuum constant temperature rotary evaporation.
More preferably, the constant temperature is 40 ℃.
The sucrose monoester final product is applied as a surfactant in the food field, including being used as a food foaming agent and a food emulsifying agent, and meanwhile, the sucrose monoester also has excellent antibacterial performance and potential anti-tumor activity, so that the sucrose monoester final product can be used as a food preservative and can be used for preparing anticancer active medicines.
Compared with the prior art, the invention has the following advantages and beneficial effects:
the invention provides a preparation method of sucrose monoester, which adopts a mixture of anhydrous tertiary butanol and pyridine as a solvent, and novelin lipase TLIM has higher activity in the solvent, and can promote the conversion of reactants, so that the yield is improved by more than 60 percent, even more than 80 percent. Therefore, the sucrose monoester prepared by the method has the advantages of high surface activity, good foamability, excellent emulsifying effect, good antibacterial effect and anticancer activity.
Drawings
FIG. 1 is a process flow diagram of the present invention.
FIG. 2 is a graph comparing foaming properties of sucrose monoesters obtained in example 1 with those of commercial sugar esters P-1570 and S-1170, wherein numerals 2-9 in the abscissa represent sucrose monoesters 2-9, respectively.
FIG. 3 is a graph showing the particle size distribution of emulsion droplets of sucrose monoesters obtained in example 1 for preparing different edible oils (soybean oil, rapeseed oil, olive oil), wherein 2, 4, 6, 8 represent sucrose monoesters 2, 4, 6, 8, respectively.
FIG. 4 shows the emulsion of sucrose monoester obtained in example 1 at different cations (Na + And Ca 2+ ) The particle size distribution of emulsion droplets at different concentrations (50-100 mM) of (2), 4, 6, 8 respectively represent sucrose monoester 2, sucrose monoester 4, sucrose monoester 6, sucrose monoester 8.
FIG. 5 shows the emulsion of sucrose monoester obtained in example 1 at different cations (Na + And Ca 2+ ) Jiao Tu of emulsion droplets at different concentrations (50-100 mM), wherein 2, 4, 6, 8 represent sucrose monoester 2, sucrose monoester 4, sucrose monoester 6, sucrose monoester 8, respectively.
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the sucrose monoester (sucrose monoester 2) obtained in example 1.
FIG. 7 is a nuclear magnetic resonance carbon spectrum of the sucrose monoester (sucrose monoester 2) obtained in example 1.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but embodiments of the present invention are not limited thereto. The raw materials related to the invention can be directly purchased from the market. For process parameters not specifically noted, reference may be made to conventional techniques.
The materials and characterization methods used in the following examples are as follows:
(1) Materials:
sucrose @>90.0 percent of vinyl laurate%>99.0 percent of vinyl myristate%>99.0 percent of vinyl palmitate%>96.0%) and vinyl stearate%>95.0%) was purchased from tokyo chemical industry limited (tokyo, japan). Tertiary butanol (anhydrous), pyridine (anhydrous) were purchased from Shanghai energy chemical company, inc. Lipase TLIM is produced by Norand Norde Corp
Denmark), and P-1170 and S-1570 are available from mitsubishi chemical food corporation, tokyo, japan.
(2) The characterization method comprises the following steps:
recording sucrose monoester on nuclear magnetic resonance spectrometer at 25 DEG C 1 H and 13 and C. For the following 1 H NMR spectrum, taking proton signal of solvent residue as internal standard.
Examples 1 to 8
Examples 1-8 provide methods for preparing sucrose monoesters, specifically as follows:
(1) 0.51g of sucrose (1 equivalent of sucrose mass) was dissolved in 15mL of an organic solvent system of both dry t-butanol and dry pyridine, and 4 equivalents of vinyl ester of fatty acid and 0.45g of Norwegian lipase enzyme TLIM were added and reacted at 40℃for 8 hours.
(2) Purifying the product obtained in the step (1), and eluting with dichloromethane/methanol solution with a volume ratio of 22:3 by adopting a silica gel chromatographic column method, wherein R is as follows f =0.6 to give sucrose monoester, purity of purified product was all>95% (according to 1 H NMR spectroscopic analysis judgment).
Example 9
The difference from example 1 is that the purification method of step (2) is: according to the solubility of sugar and ester in water and organic phase, extracting and recrystallizing, purifying by silica gel chromatographic column method, and the purity of the purified product is more than 95%.
Comparative example 1
Anhydrous t-butanol was replaced with equal volumes of t-amyl alcohol.
Comparative example 2
Anhydrous pyridine was replaced with an equal volume of anhydrous tetrahydrofuran.
The specific types, reaction yields and reaction product numbers of the fatty acid vinyl esters added in examples 1 to 9 and comparative examples 1 to 2 are shown in Table 1, and the characterization data of the sucrose monoesters obtained in examples 1 to 8 are shown in Table 2.
TABLE 1
| Fatty acid vinyl ester | Yield is good | Product name (number) | |
| Example 1 | Vinyl laurate | 67.7％ | Sucrose laurate (sucrose monoester 2) |
| Example 2 | Vinyl myristate | 70.1％ | Sucrose myristate (sucrose monoester 3) |
| Example 3 | Vinyl palmitate | 79.5％ | Sucrose palmitate (sucrose monoester 4) |
| Example 4 | Vinyl stearate | 78.6％ | Sucrose stearate (sucrose monoester 5) |
| Example 5 | Vinyl oleate | 80.4％ | Sucrose oleate (sucrose monoester 6) |
| Example 6 | Vinyl eicosanoate | 76.3％ | Sucrose eicosanoate (sucrose monoester 7) |
| Example 7 | Vinyl behenate | 71.6％ | Sucrose behenate (sucrose monoester 8) |
| Example 8 | Erucic acid vinyl ester | 66.9％ | Sucrose erucic acid ester (sucrose monoester 9) |
| Example 9 | Vinyl laurate | 50.5％ | Sucrose laurate (D1) |
| Comparative example 1 | Vinyl laurate | 6.0％ | Sucrose laurate (D4) |
| Comparative example 2 | Vinyl laurate | 9.2％ | Sucrose laurate(D5) |
TABLE 2
As can be seen from tables 1 and 2, the present invention successfully synthesizes sucrose monoesters, and the reaction has a higher yield, higher than 60%, even higher than 80%.
The comparative example 1 and the comparative example 2 each replaced one of the solvents, and the reaction yield was significantly reduced, thereby proving that the yield of the reaction could be effectively improved only by using both of the anhydrous t-butanol and the anhydrous pyridine as the solvents.
As is clear from the comparison between example 1 and example 9, the silica gel column chromatography (example 1) can further improve the yield of the reaction compared with other purification methods (example 9).
Test example 1 surface Properties of sucrose monoester
(1) The purpose is as follows: the surface properties of sucrose monoesters (2-9), including critical micelle concentration, surface tension, oil-water interfacial tension and contact angle, were measured using a video contact angle meter (dataphysics, OCA, germany). And the water solubility of the different sucrose monoesters was studied.
(2) The process comprises the following steps: the Critical Micelle Concentration (CMC) and the surface tension (gamma) of the different sugar ester solutions were determined at 20℃using an UpHSV1220 automatic interfacial tensiometer by means of the pendant drop method CMC ) Interfacial tension (gamma) O/W ) The contact angle (θ) was measured using the sitting-drop method. For measurement of water solubility, 1mL of a saturated aqueous solution of sugar ester was taken, and the mass thereof was weighed after drying.
(3) The critical micelle concentration is represented by CMC and the surface tension by gamma CMC The interfacial tension was represented by γo/W, the contact angle by θ, and the data after a plurality of measurements were shown in table 3.
TABLE 3 Table 3
(4) Data analysis:
as can be seen from the above table data, as the hydrophobic alkyl carbon chain grows, the critical micelle concentration decreases, and the surface tension at the critical micelle concentration also shows a decreasing trend. The change trend of the oil-water interfacial tension and the contact angle is similar to the change trend of the critical micelle concentration and the surface tension, which shows that the synthesized sucrose monoester has good effect of reducing the surface tension, the oil-water interfacial tension and the gas-liquid-solid three-phase interfacial tension, and the reduction effect is more obvious along with the increase of the alkyl carbon chain. As can be seen from its water solubility, the water solubility of the sucrose monoester decreases significantly with the extension of the alkyl fatty acid chain, indicating that the water solubility of the synthetic sucrose monoester has a significant difference.
Test example 2 foaming Properties of sucrose monoester
(1) The method comprises the following steps:
20mL of sucrose monoesters 2-9 and aqueous solutions of S-1170 and P-1570 (sugar ester content 0.3% and 0.6% w/w) were placed in 100mL measuring flasks, respectively, and the volume of the solutions was measured (V 0 ). Each sample was placed in a stirrer operating at 16000 rpm for 1 minute, and the resulting foam volume (V 1 ) And the total volume of each sample (V 2 ). In the foam volume (V) 1 ) Reduced half post-recording time(foam half-shrink period), which is used to indicate their foam stability. The foamability of these was calculated using the following equation: foaming ability (%) = (V) 2 －V 0 )/V 0 X 100%; foaming stability (min) =t (1/2V 1 )
(2) Data: FIG. 2 of the accompanying drawings
(3) Data analysis:
the foaming capacity of sucrose monoesters and of the control group (commercially available sugar esters S-1170 and P-1570) was measured at concentrations of 0.3% and 0.6% w/w. The results of these studies (fig. 2) reveal a moderately positive correlation between foaming capacity and sample concentration.
At concentrations of 0.3-0.6% w/w, sucrose monoesters 2-4 showed superior foaming properties than the control group, and sucrose monoesters 5-6 also showed better foaming stability than the control group. When the length of the alkyl side chain is increased to 18 carbons, the foamability decreases, and particularly when the length of the alkyl side chain is increased to 20 carbons and above, both the foamability and the foamability stability thereof decrease significantly.
Test example 3 emulsification Properties of sucrose monoester
(1) Preparation of emulsion: 60g of aqueous solutions of various sucrose monoesters (sucrose monoesters 2-9, commercial sugar esters P-1570 and S-1170) with a volume fraction of 0.5% were each prepared and poured into 10g of oil (olive oil, soybean oil, rapeseed oil) respectively. Then, the mixture was subjected to high-pressure shearing at 25000 rpm for 2 minutes, and then homogenized by a high-pressure homogenizer at a pressure of 90mPa for 5 cycles.
(2) Emulsion stability evaluation method: the particle size and particle size distribution of the emulsion were measured by a laser particle sizer (SALD-2300, shimadzu, japan) and the microstructure of the emulsion was observed by a Zeiss fluorescence confocal microscope (LSM 880, carl Zeiss, germany).
(3) Relevant experiments on emulsion stability: the oil type has an effect on stability, storage at different temperatures has an effect on stability, and inorganic salts have an effect on stability.
Data and analysis:
a) Influence of oil content: the average particle size of the different emulsions is shown in Table 4, in nm.
TABLE 4 Table 4
From the data in fig. 3 and table 4, it can be seen that the types of oils are different and that the particle sizes of emulsions prepared from the same sucrose monoester are different. The emulsion particle size is significantly smaller when the oil is soybean oil than when the oil is olive oil, and the difference gradually decreases with increasing sucrose fatty acid chain. As sucrose fatty acid chains increase, the particle size of the emulsion increases. For sucrose monoester 2-6, there was very strong emulsifying capacity and exceeded the commercial surfactants P-1570 and S-1170. From particle size distribution 3, it can be seen that the particle size distribution is a relatively concentrated single peak for all oil types, which represents that emulsions prepared from all types can be stored for a longer period of time.
B) Effect of long term storage at different temperatures:
emulsions with an oil type of olive oil were used in this test.
The average particle size values of the different emulsions at different storage times are shown in Table 5, and the particle size units are nm.
TABLE 5
From the data in Table 5, it can be seen that all emulsions made with sugar esters have a certain temperature resistance. The emulsion made from sucrose monoesters 5-7 had the best stability over time: no delamination occurred macroscopically. And the emulsion stability of sucrose monoesters 5-7 is higher than that of the control group. It can also be seen from Table 5 that the effect of temperature on the stability of the emulsion is evident, and the emulsion stored at low temperature has less particle size change and good stability in the same time, and thus has longer storage time. The data of the same temperature and the same day are observed, and the emulsion stability tends to increase and decrease with the increase of the alkyl carbon chain.
C) Influence of inorganic salts:
an emulsion of olive oil type was used in this test.
The average particle size values of the different emulsions under different inorganic salts are shown in Table 6 in nm.
TABLE 6
In the experiments we used sodium chloride and calcium chloride with cation concentrations of 50-150mM to study the effect of different salts and different cation intensities on emulsion stability.
According to the analysis in the table above, all the synthesized sucrose monoesters and the control P-1570 and S-1170 showed no delamination at cation concentrations of 50-100mM for 24 hours, indicating a better salt tolerance. As can be seen from the change in the particle size distribution of fig. 4: as the carbon chain grows, the influence of the change of salt concentration and salt type on the stability of the emulsion is reduced from sucrose monoester 2 to sucrose monoester 6. Sucrose monoester 5 and sucrose monoester 6 of the same carbon chain length, sucrose monoester 8 and sucrose monoester 9 vary little. This can be more fully illustrated by the confocal images of fig. 5.
The effect of sodium chloride on emulsion stability is greater than that of calcium chloride. The emulsion prepared from the commercial emulsifying agents S-1170 and P-1570 has ion stability which is obviously lower than that of the synthesized sucrose monoester. With the extension of alkyl chain, the ion stability is reduced, and the emulsion prepared from 2-6 in the sucrose monoester has stronger capability of resisting calcium chloride salt, wherein the emulsion prepared from 2-4 in the sucrose monoester has more outstanding resistance to sodium chloride salt.
Test example 4 antibacterial Properties of sucrose monoester
(1) The method comprises the following steps: the minimum inhibitory concentration of sucrose monoester on 7 bacteria was determined by microdilution. 1.28mg of each ester sample was dissolved in 1mL of DMSO solution at 37℃and added to Mi Le Haton medium of the cultured strain for 24 hours. Subsequently adjusting the turbidity of the bacterial suspension to5×10 5 CFU/mL. The optical density at 595nm per well was measured using a 96-well plate and a multispan MK3 microplate reader (Thermo Labsystems, helsinki, finland).
(2) Data: the minimum inhibitory concentrations of sucrose monoester and control sodium benzoate, vancomycin, for 7 bacteria were determined by densitometry as detailed in table 7, in μg/mL.
TABLE 7
(3) Data analysis:
although the bacteriostasis effect of the sucrose monoester prepared by the invention is different for different bacteria, the sucrose monoester prepared by the invention has better bacteriostasis effect for the bacteria, and compared with the commercial ester S-1170, the sucrose monoesters 6 and 8 have better bacteriostasis effect.
Test example 5 antitumor Properties of sucrose monoester
(1) The method comprises the following steps: cells were plated at 37℃on 96-well plates of 100mol/L complete medium (DMEM+5% foetal calf serum, 50 units/mL penicillin, 50mol/mL streptomycin) at a density of 3000 cells/well and at 5% CO 2 After 12 hours of incubation, the medium was removed, fresh, complete medium containing the test sample was added to the well and after 24 hours of incubation, 5mg/mL MTT stock solution was added to each well. Then incubated for 4 hours in the same environment. Finally, absorbance was measured at 570nm using an Epoch2 microplate reader (Biotek Instruments, winioski, VT). Results are expressed as the maximal inhibitory concentration of half the lethality, i.e. the dose at which the sample resulted in a 50% loss of cell viability.
(2) Data: the half lethal doses of sucrose monoester and control doxorubicin on 5 cells are detailed in table 8, in μm.
TABLE 8
(3) Data analysis:
the sucrose monoester provided by the invention has good effect on the activity inhibition of 6 cells, wherein the cytotoxicity of the sucrose monoester 2 is smaller, the general trend of cytotoxicity of the sucrose monoester 4-9 is greater along with the increase of the carbon chain length, and the cytotoxicity of the sucrose monoester 4-9 is greater than that of the commercial sugar ester S-1170.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (5)
1. The preparation method of the sucrose monoester with antibacterial and antitumor activities is characterized by comprising the following steps:
reacting sucrose and fatty acid vinyl ester under the action of enzyme to obtain a sucrose monoester mixture, and purifying to obtain sucrose monoester;
the fatty acid vinyl ester is one of vinyl arachidate, vinyl behenate and vinyl erucic acid;
the mol ratio of the sucrose to the fatty acid vinyl ester is 1:4;
the enzyme is an enzyme capable of catalyzing sucrose and organic acid vinyl ester to carry out transesterification reaction;
the solvent of the reaction is the combination of anhydrous tertiary butanol and anhydrous pyridine;
the enzyme is novelin lipase TLIM, and the volume ratio of the anhydrous tertiary butanol to the anhydrous pyridine is 1:1;
the purification method is column chromatography, and the mobile phase is a mixed solvent combination containing dichloromethane and methanol; the volume ratio of the dichloromethane to the methanol is 22:3;
the temperature of the reaction was 40℃and the time of the reaction was 8h.
2. The method for producing sucrose monoester having antibacterial and antitumor activity as claimed in claim 1, wherein the column chromatography is silica gel column chromatography.
3. The method for preparing sucrose monoester with antibacterial and antitumor activity as claimed in claim 1, wherein the preparation method specifically comprises the following steps:
(1) Adding anhydrous tertiary butanol and pyridine in a volume ratio of 1:1 and 4 equivalents of fatty acid vinyl ester into 1 equivalent of sucrose, adding novelin lipase TLIM, and reacting at 40 ℃ for 8 h;
(2) And (3) performing column chromatography on the reaction product obtained in the step (1), and removing the solvent to obtain the sucrose monoester.
4. The method for preparing sucrose monoester having antibacterial and antitumor activity as claimed in claim 3, wherein the solvent removal method comprises vacuum constant temperature rotary evaporation.
5. The application of the sucrose monoester with antibacterial and antitumor activities prepared by the preparation method of any one of claims 1-4, which is characterized in that the sucrose monoester is used as a surfactant in the food field, and is applied to preparation of listeria and staphylococcus aureus inhibiting products or HEK-293, NCI-H226, MCF-7, RPMI8226 and Sup T1 cell line resisting medicaments.
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