CN116925785A - Compound of gleditsia sinensis saponin and camellia saponin and preparation method thereof - Google Patents
Compound of gleditsia sinensis saponin and camellia saponin and preparation method thereof Download PDFInfo
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- 239000001397 quillaja saponaria molina bark Substances 0.000 title claims abstract description 275
- 229930182490 saponin Natural products 0.000 title claims abstract description 275
- 150000007949 saponins Chemical class 0.000 title claims abstract description 268
- 241000931143 Gleditsia sinensis Species 0.000 title claims abstract description 128
- 240000001548 Camellia japonica Species 0.000 title claims abstract description 52
- 235000018597 common camellia Nutrition 0.000 title claims abstract description 51
- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 174
- 239000011347 resin Substances 0.000 claims abstract description 58
- 229920005989 resin Polymers 0.000 claims abstract description 58
- 241001122767 Theaceae Species 0.000 claims abstract description 55
- 239000010495 camellia oil Substances 0.000 claims abstract description 37
- 239000003921 oil Substances 0.000 claims abstract description 36
- 241000526900 Camellia oleifera Species 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000001179 sorption measurement Methods 0.000 claims abstract description 22
- 239000000693 micelle Substances 0.000 claims abstract description 18
- 239000010779 crude oil Substances 0.000 claims abstract description 17
- 239000012535 impurity Substances 0.000 claims abstract description 14
- 238000000926 separation method Methods 0.000 claims abstract description 14
- 238000005215 recombination Methods 0.000 claims abstract description 12
- 230000006798 recombination Effects 0.000 claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 239000008367 deionised water Substances 0.000 claims description 22
- 229910021641 deionized water Inorganic materials 0.000 claims description 22
- 101001097774 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 40S ribosomal protein S21-A Proteins 0.000 claims description 16
- 101001097805 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) 40S ribosomal protein S21-B Proteins 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 238000011068 loading method Methods 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 238000007873 sieving Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 2
- WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims 1
- NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 14
- 230000007547 defect Effects 0.000 abstract description 3
- 229930192760 sasanquasaponin Natural products 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 81
- 235000019198 oils Nutrition 0.000 description 28
- 239000007864 aqueous solution Substances 0.000 description 13
- -1 saponin compound Chemical class 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 235000012054 meals Nutrition 0.000 description 5
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 241000533849 Gleditsia Species 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 102220079700 rs144667627 Human genes 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003809 water extraction Methods 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 235000019750 Crude protein Nutrition 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 244000147058 Derris elliptica Species 0.000 description 1
- 240000003133 Elaeis guineensis Species 0.000 description 1
- 235000001950 Elaeis guineensis Nutrition 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000003700 hair damage Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/56—Glucosides; Mucilage; Saponins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G3/00—Glycosides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/017—Mixtures of compounds
- C09K23/018—Mixtures of two or more different organic oxygen-containing compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to the field of natural saponin separation and recombination, in particular to a compound of gleditsia sinensis saponin and camellia saponin and a preparation method thereof. The method comprises the following steps: 1) Respectively extracting gleditsia sinensis peel and oil tea cake to obtain crude gleditsia sinensis saponin solution and crude oil tea saponin solution; 2) Macroporous adsorption resin AB-8 is used as a resin separation column to respectively wash and remove impurities from crude gleditsia sinensis saponin solution and crude tea-oil camellia saponin solution; 3) Sequentially eluting with 25-35% ethanol solution, 40-50% ethanol solution, 55-65% ethanol solution and 70-85% ethanol solution to obtain gleditsia sinensis saponin solution and tea-oil camellia saponin solution respectively to obtain gleditsia sinensis saponin component and tea-oil camellia saponin component; 4) And (3) carrying out component recombination on the gleditsia sinensis saponin component and the camellia oleifera saponin component to obtain a compound of the gleditsia sinensis saponin and the camellia oleifera saponin. The invention can improve the purity of the natural saponin and the surface activity of the saponin, and overcomes the defect of higher critical micelle concentration of the sasanqua saponin.
Description
Technical Field
The invention relates to the field of natural saponin separation and recombination, in particular to a compound of gleditsia sinensis saponin and camellia saponin and a preparation method thereof.
Background
The gleditsia sinensis (Gleditisia sinensis lam.) is of the genus gleditsia of the family Leguminosae, is arbor, is up to 30 m, is in the shape of a fruit belt, is 5-35 cm long, is bent or straight, and is blackish brown or purple red; the seeds are majority, oblong, flat, about 1 cm long, bright brown. The gleditsia sinensis is a multifunctional ecological economic tree species which is distributed all over the country and has a full bearing period of more than one hundred years. The gleditsia sinensis tree has developed root system, light preference, cold resistance, drought resistance, barren resistance, pollution resistance, disease and insect resistance and wide adaptability, is suitable for urban and rural landscape forests and road greening, can be used as a protective forest and a water and soil conservation forest tree species, and is listed in the national reserve forest tree species and yellow river basin ecological management ten tree species. The gleditsia sinensis polysaccharide has extremely high economic value, the gleditsia sinensis saponin is a high-quality natural surfactant, and the gleditsia sinensis saponin has the characteristics of environmental protection, no toxicity, biodegradability and the like, and has both economic value and ecological value. At present, the planting area of the gleditsia sinensis in the whole country exceeds 200 ten thousand acres.
The oil tea (Camellia oleifera Abel) is a generic name of a plant with high grease content in camellia plants and cultivation economic value, and is called as 4 woody oil tree species in the world together with oil palm, olive and coconut. The Chinese has quite abundant oil tea resources, and mainly comprises more than 10 varieties of common oil tea, zhenhan camellia, zhejiang safflower oil tea, zhexian oil tea, small fruit oil tea, vietnam oil tea, japanese red camellia and the like. The camellia seed is provided with a shell, contains 50% -72% of kernel, 30% -40% of whole seed oil, 40% -60% of kernel oil, 8% -9% of crude protein, and the camellia oil is non-drying oil with unsaturated fatty acid content as high as 85% -97%, and is crown of various edible oils. Every 1 ton of tea oil is produced, and about 4 tons of tea cake and about 7 tons of tea shells are produced at the same time. The oil tea cake contains abundant saponin, and if the oil tea seeds can be fully developed and utilized, the economic benefit of the oil tea is 2-3 times of that of the pure tea oil. The oil tea is distributed in Yangtze river basin and south area in China, and the cultivation area is over 7000 ten thousand mu.
The natural saponin is used as a surfactant and has the characteristics of environmental protection, no toxicity, biodegradability and the like. With the update and progress of people's living concept and the improvement of living standard, the daily detergent safety is more and more emphasized. However, for a long time, synthetic surfactants using fossil resources as raw materials have been the first choice for daily chemical detergents and cosmetics, and not only directly cause skin allergy and hair damage, but also accumulated chemical substances pollute the environment and harm the organisms in water, and the health of people is influenced along with food chains. The saponin is a natural surfactant, and does not bring negative problems of fluorescent agent, environmental hormone, river oxidation and the like. The use of renewable plant resources to produce degradable washing products is a necessary trend for human survival and development. At present, the problems of high purification cost, incomplete impurity removal, low surface activity of single natural saponin and the like still exist in the production process of the natural saponin.
Disclosure of Invention
In order to solve the technical problems, the invention provides a compound of gleditsia sinensis saponin and camellia oleifera saponin and a preparation method thereof.
In a first aspect, the preparation method of the complex of gleditsia sinensis saponin and camellia oleifera saponin provided by the invention comprises the following steps:
1) Respectively extracting gleditsia sinensis peel and oil tea cake to obtain crude gleditsia sinensis saponin solution and crude oil tea saponin solution;
2) Macroporous adsorption resin AB-8 is used as a resin separation column, and the crude gleditsia sinensis saponin solution and the crude tea-oil camellia saponin solution are respectively eluted to remove impurities;
3) Eluting the gleditsia sinensis saponin solution and the camellia saponin solution obtained in the step 2) with 25-35% ethanol solution, 40-50% ethanol solution, 55-65% ethanol solution and 70-85% ethanol solution respectively in sequence to obtain a gleditsia sinensis saponin component and a camellia saponin component respectively;
4) And (3) carrying out component recombination on the gleditsia sinensis saponin component and the camellia oleifera saponin component to obtain a compound of the gleditsia sinensis saponin and the camellia oleifera saponin.
The invention selects macroporous adsorption resin AB-8 to remove impurities, can well realize component separation of gleditsia sinensis saponin and tea-oil saponin, and simultaneously innovatively provides optimized recombination among different components of gleditsia sinensis saponin and tea-oil saponin on the basis of analysis and characterization of each component structure and performance system of natural saponin, improves the purity of the saponin, improves the surface activity performance of the saponin, and overcomes the defect of higher critical micelle concentration of the tea-oil saponin.
Preferably, in the step 1), deionized water is used as an extracting agent to extract the gleditsia sinensis pericarp to obtain crude gleditsia sinensis saponin solution; and/or extracting the oil tea cake by using methanol as an extracting agent, and filtering and drying to obtain crude oil tea saponin.
Further preferably, in the step 1), the gleditsia sinensis pericarp is crushed and sieved by a 35-40 mesh sieve, deionized water is used as an extracting agent, the solid-liquid ratio is 1:8-10, stirring and extracting are carried out for 6-7 h, and filtering is carried out to obtain crude gleditsia sinensis saponin solution;
and/or crushing the oil tea cake, sieving with a 20-30 mesh sieve, taking methanol as an extracting agent, stirring and extracting for 6-7 h with a solid-liquid ratio of 1:4-6, filtering and drying to obtain crude oil tea saponin.
In the invention, crude gleditsia sinensis saponin is extracted by adopting a water extraction method, and oil tea saponin is extracted by adopting methanol, so that the method has the characteristics of high product yield, low extraction cost and the like.
Preferably, in step 2), the washing is sequentially performed by deionized water and 10-15% ethanol solution.
Further preferably, in the step 2), the crude gleditsia sinensis saponin solution is filled into macroporous adsorption resin AB-8, and is sequentially eluted by deionized water with the volume of 2-3 times of resin and 5-15% ethanol solution with the volume of 2-3 times of resin;
and/or loading the crude oil tea saponin solution into macroporous adsorption resin AB-8, and eluting with deionized water with the volume of 2-3 times of the resin volume and 5-15% ethanol solution with the volume of 2-3 times of the resin volume in sequence.
In the invention, research shows that the adoption of the specific macroporous adsorption resin AB-8 is favorable for purifying the saponin. The impurities in the gleditsia sinensis saponin and the camellia saponin can be removed to the greatest extent by adopting the deionized water and the low-concentration ethanol aqueous solution with the dosages respectively through the macroporous adsorption resin.
According to the invention, the method preferably further comprises the step of preparing the crude oil tea saponin into 15-20% crude oil tea saponin aqueous solution.
Preferably, in the step 3), for crude gleditsia sinensis saponin, 30-35% ethanol solution, 45-50% ethanol solution, 55-60% ethanol solution and 70-75% ethanol solution are sequentially used for eluting to obtain gleditsia sinensis saponin component ZS30, gleditsia sinensis saponin component ZS45, gleditsia sinensis saponin component ZS60 and gleditsia sinensis saponin component ZS75;
and/or eluting crude oil tea saponin with 25-30% ethanol solution, 40-45% ethanol solution, 60-65% ethanol solution and 75-85% ethanol solution in sequence to obtain oil tea saponin component YS25, oil tea saponin component YS45, oil tea saponin component YS65 and oil tea saponin component YS85.
According to the invention, purified gleditsia sinensis saponin and tea-oil saponin with different structures and properties can be respectively obtained by adopting ethanol water solutions with different concentrations through macroporous adsorption resin. The macroporous adsorption resin eluted by the ethanol water solutions with different concentrations can directly separate the next batch of saponin without regeneration. The synergistic effect of the structure and the property exists between different gleditsia sinensis saponin components and oil tea saponin components, so that the surface activity of the compound of the gleditsia sinensis saponin and the oil tea saponin is greatly improved.
Further preferably, in the step 3), the 30-35% ethanol solution is 5-6 times of the resin volume, the 45-50% ethanol solution is 10-12 times of the resin volume, the 55-60% ethanol solution is 5-6 times of the resin volume, and the 70-75% ethanol solution is 2-3 times of the resin volume; and/or the volume of the 25-30% ethanol solution is 3-4 times of the volume of the resin, the volume of the 40-45% ethanol solution is 8-9 times of the volume of the resin, the volume of the 60-65% ethanol solution is 3-4 times of the volume of the resin, and the volume of the 75-85% ethanol solution is 1.5-2 times of the volume of the resin.
In the invention, the eluent and the dosage proportion thereof are optimized, so that the saponin components with better structural performance can be obtained, and the synergistic effect among the components can be generated, thereby being beneficial to further improving the surface activity and the product purity of the saponin compound.
Preferably, in the step 4), the ratio of the gleditsia sinensis saponin component to the camellia oleifera saponin component is adjusted, so that the critical micelle concentration and the surface tension of the complex of the gleditsia sinensis saponin and the camellia oleifera saponin are adjustable.
In a second aspect, the compound of gleditsia sinensis saponin and tea-oil camellia saponin provided by the invention is obtained by a preparation method of the compound of gleditsia sinensis saponin and tea-oil camellia saponin.
Preferably, the compound of the gleditsia sinensis saponin and the camellia oleifera saponin is a compound of one or more of a gleditsia sinensis saponin component ZS30, a gleditsia sinensis saponin component ZS45, a gleditsia sinensis saponin component ZS60, a gleditsia sinensis saponin component ZS75, a camellia oleifera saponin component YS25, a camellia oleifera saponin component YS45, a camellia oleifera saponin component YS65 and a camellia oleifera saponin component YS85.
In the invention, on the premise of purification and optimized separation, the surface activity of the saponin compound is improved by fully playing the synergistic effect. Especially, the components ZS60 and ZS75 of the gleditsia sinensis saponin can reduce the critical micelle concentration of the tea-oil camellia saponin and improve the surface activity of the compound saponin. The components YS25 and YS85 of the oil tea saponin can reduce the surface tension of the gleditsia sinensis saponin and improve the surface activity of the compound saponin. The complex with the synergistic specific saponin components has more excellent surface activity, and has more excellent critical micelle concentration and surface tension.
Further preferably, the compound of the gleditsia sinensis saponin and the tea-oil camellia saponin is a compound of tea-oil camellia saponin component YS25, tea-oil camellia saponin component YS45, tea-oil camellia saponin component YS65, tea-oil camellia saponin component YS85, gleditsia sinensis saponin component ZS60 and gleditsia sinensis saponin component ZS75 with the mass ratio of 5-6:28-30:15-18:4-5:8-12:1-2; or the mass ratio of the compound of the gleditsia sinensis saponin to the tea-oil camellia saponin is 1-3:30-32: 18-22:1-3:2-3:1-3 of gleditsia sinensis saponin component ZS30, gleditsia sinensis saponin component ZS45, gleditsia sinensis saponin component ZS60, gleditsia sinensis saponin component ZS75, tea-oil camellia saponin component YS25 and tea-oil camellia saponin component YS85.
Further preferably, the surface tension of the complex of the gleditsia sinensis saponin and the camellia saponin is 34.6-41 mN/m, and the critical micelle concentration is 0.1-1.5 g/L.
The invention has the advantages that: the preparation method of the gleditsia sinensis saponin and the tea-oil camellia saponin provided by the invention overcomes the defect of high critical micelle concentration of the tea-oil camellia saponin, and the saponin compound has higher surface activity. 1) The crude gleditsia sinensis saponin is extracted by adopting a water extraction method, and the oil tea saponin is extracted by adopting methanol, so that the method has the characteristics of high product yield, low extraction cost and the like. 2) And removing impurities in the gleditsia sinensis saponin and the camellia saponin to the greatest extent by using deionized water and a low-concentration ethanol aqueous solution through macroporous adsorption resin respectively. 3) Purified gleditsia sinensis saponin and tea-oil saponin with different structures and properties can be respectively obtained by adopting ethanol water solutions (25% -85%) with different concentrations through macroporous adsorption resin. 4) The components ZS60 and ZS75 of the gleditsia sinensis saponin can reduce the critical micelle concentration of the tea-oil camellia saponin and improve the surface activity of the compound saponin. 5) The components YS25 and YS85 of the oil tea saponin can reduce the surface tension of the gleditsia sinensis saponin and improve the surface activity of the compound saponin. 6) The macroporous adsorption resin eluted by the ethanol water solutions with different concentrations can directly separate the next batch of saponin without regeneration. 7) The structural and property effects of different gleditsia sinensis saponin components and oil tea saponin components are the same, so that the surface activity of the compound of gleditsia sinensis saponin and oil tea saponin is greatly improved.
Drawings
In order to more clearly illustrate the embodiments of the present invention and the technical solutions of the prior art, the following description will briefly explain the embodiments or the drawings needed in the description of the prior art, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a process flow chart provided in embodiment 1 of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions in the embodiments of the present invention are clearly and completely described below. It will be apparent that the described embodiments are some, but not all, embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Unless otherwise indicated, the starting materials and reagents used in the following examples were either commercially available or may be prepared by known methods. The examples are not intended to identify the particular technology or conditions, and are either conventional or are carried out according to the technology or conditions described in the literature in this field or are carried out according to the product specifications. The reagents and instruments used, etc. are not identified to the manufacturer and are conventional products available for purchase by regular vendors.
The invention will be further illustrated with reference to examples.
Example 1
The embodiment provides a compound of gleditsia sinensis saponin and camellia oleifera saponin, and the preparation process flow is shown in figure 1. The preparation method comprises the following steps: crushing the dried camellia seed meal, sieving with a 30-mesh sieve, taking methanol as an extracting agent, extracting with stirring for 4 hours according to the solid-to-liquid ratio of 1:8, filtering, and drying to obtain crude camellia saponin. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method, loading crude oil tea saponin water solution into a resin separation column, sequentially eluting with 3 times of deionized water and 10% ethanol solution (the resin volume, the same applies below), and removing impurities in the saponin. Sequentially eluting with 25% ethanol solution (3 times volume), 45% ethanol solution (8 times volume), 65% ethanol solution (3 times volume) and 85% ethanol solution (3 times volume) to obtain fructus Gleditsiae Abnormalis saponin components YS25, YS45, YS65 and YS85, concentrating and drying respectively.
Crushing the dried gleditsia sinensis peels, sieving the crushed gleditsia sinensis peels with a 40-mesh screen, taking deionized water as an extracting agent, stirring and extracting for 6 hours according to the solid-to-liquid ratio of 1:8, and filtering to obtain crude gleditsia sinensis saponin aqueous solution. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method column, loading crude gleditsia sinensis saponin aqueous solution into a resin separation column, sequentially eluting with 2 times of deionized water and 10% ethanol solution, and removing impurities in the saponin. Sequentially eluting with 30% ethanol solution (5 times volume), 45% ethanol solution (10 times volume), 60% ethanol solution (5 times volume) and 75% ethanol solution (2 times volume) to obtain fructus Gleditsiae Abnormalis saponin components ZS30, ZS45, ZS60 and ZS75, concentrating and drying respectively. The saponin recombination is carried out according to the mass ratio ZS30:ZS45:ZS60:ZS75:YS 25:YS85=2:31:20:1.5:2.5:2. The critical micelle concentration of the recombinant saponin is measured to be 0.1g/L, and the surface tension is measured to be 34.6mN/m.
Example 2
Crushing the dried camellia seed meal, sieving with a 30-mesh sieve, taking methanol as an extracting agent, stirring and extracting for 4 hours according to the solid-to-liquid ratio of 1:8, and filtering to obtain crude camellia saponin aqueous solution. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method, loading crude oil tea saponin water solution into a resin separation column, sequentially eluting with 3 times of deionized water and 10% ethanol solution, and removing impurities in saponin. Sequentially eluting with 25% ethanol solution (3 times volume), 45% ethanol solution (8 times volume), 65% ethanol solution (3 times volume) and 85% ethanol solution (3 times volume) to obtain fructus Gleditsiae Abnormalis saponin components YS25, YS45, YS65 and YS85, concentrating and drying respectively. Crushing the dried gleditsia sinensis peels, sieving the crushed gleditsia sinensis peels with a 40-mesh screen, taking deionized water as an extracting agent, stirring and extracting for 6 hours according to the solid-to-liquid ratio of 1:8, and filtering to obtain crude gleditsia sinensis saponin aqueous solution. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method, loading crude gleditsia sinensis saponin aqueous solution into a resin separation column, sequentially eluting with 2 times of deionized water and 10% ethanol solution (the resin volume, the same applies below), and removing impurities in the saponin. Sequentially eluting with 30% ethanol solution (5 times volume), 45% ethanol solution (10 times volume), 60% ethanol solution (5 times volume) and 75% ethanol solution (2 times volume) to obtain fructus Gleditsiae Abnormalis saponin components ZS30, ZS45, ZS60 and ZS75, concentrating and drying respectively. The saponin recombination is carried out according to the mass ratio YS25:YS45:YS65:YS85:ZS 60:ZS75=5.5:29:16:4.3:10:1. The critical micelle concentration of the recombinant saponin is measured to be 0.12g/L, and the surface tension is measured to be 38.5mN/m.
Example 3
Crushing the dried camellia seed meal, sieving with a 30-mesh sieve, taking methanol as an extracting agent, stirring and extracting for 4 hours according to the solid-to-liquid ratio of 1:8, and filtering to obtain crude camellia saponin aqueous solution. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method, loading crude oil tea saponin water solution into a resin separation column, sequentially eluting with 3 times of deionized water and 10% ethanol solution, and removing impurities in saponin. Sequentially eluting with 25% ethanol solution (3 times volume), 45% ethanol solution (8 times volume), 65% ethanol solution (3 times volume) and 85% ethanol solution (3 times volume) to obtain fructus Gleditsiae Abnormalis saponin components YS25, YS45, YS65 and YS85, concentrating and drying respectively. And carrying out saponin recombination according to a mass ratio YS 25:YS45:YS65:YS85=2:15:20:1.5. And performing saponin recombination according to the mass ratio S30, hydrolysis S45, S60, S75=5.5:29:16:4.3. The critical micelle concentration of the recombinant saponin is 1.5g/L and the surface tension is 40.5mN/m.
Example 4
Crushing the dried gleditsia sinensis peels, sieving the crushed gleditsia sinensis peels with a 40-mesh screen, taking deionized water as an extracting agent, stirring and extracting for 6 hours according to the solid-to-liquid ratio of 1:8, and filtering to obtain crude gleditsia sinensis saponin aqueous solution. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method column, loading crude gleditsia sinensis saponin aqueous solution into a resin separation column, sequentially eluting with 2 times of deionized water and 10% ethanol solution, and removing impurities in the saponin. Sequentially eluting with 30% ethanol solution (5 times volume), 45% ethanol solution (10 times volume), 60% ethanol solution (5 times volume) and 75% ethanol solution (2 times volume) to obtain fructus Gleditsiae Abnormalis saponin components ZS30, ZS45, ZS60 and ZS75, concentrating and drying respectively. The saponin recombination is carried out according to the mass ratio ZS30:ZS45:ZS60:ZS75=2:15:20:1.5. The critical micelle concentration and the surface tension of the oil tea saponin components ZS30:ZS45:ZS60:ZS75 are respectively measured, and the results are shown in the following table. And carrying out saponin recombination according to the mass ratio S30, hydrolysis S45 and S60, wherein S75=2:31:20:1.5. The critical micelle concentration of the recombinant saponin is measured to be 0.15g/L, and the surface tension is measured to be 37.2mN/m.
Comparative example 1
Crushing the dried camellia seed meal, sieving with a 30-mesh sieve, taking methanol as an extracting agent, stirring and extracting for 4 hours according to the solid-to-liquid ratio of 1:8, and filtering to obtain crude camellia saponin aqueous solution. Weighing a certain amount of macroporous adsorption resin AB-8, loading into a wet method, loading crude oil tea saponin water solution into a resin separation column, sequentially eluting with 3 times of deionized water and 10% ethanol solution, and removing impurities in saponin. Sequentially eluting with 25% ethanol solution (3 times volume), 45% ethanol solution (8 times volume), 65% ethanol solution (3 times volume) and 85% ethanol solution (3 times volume) to obtain fructus Gleditsiae Abnormalis saponin components YS25, YS45, YS65 and YS85, concentrating and drying respectively. The critical micelle concentration and surface tension of the tea saponin components YS25, YS45, YS65 and YS85 were measured respectively, and the results are shown in the following table.
TABLE 1 surface tension and critical micelle concentration of different gleditsia/tea-oil saponin components and complexes
Comparative example 2
Crushing the dried camellia seed meal, sieving with a 30-mesh sieve, taking methanol as an extracting agent, extracting for 4 hours with stirring at a solid-to-liquid ratio of 1:8, filtering to obtain crude camellia saponin aqueous solution, and determining to obtain the crude camellia saponin critical micelle concentration of 1.5g/L and the surface tension of 43.5mN/m.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. A preparation method of a compound of gleditsia sinensis saponin and camellia oleifera saponin is characterized by comprising the following steps:
1) Respectively extracting gleditsia sinensis peel and oil tea cake to obtain crude gleditsia sinensis saponin solution and crude oil tea saponin solution;
2) Macroporous adsorption resin AB-8 is used as a resin separation column, and the crude gleditsia sinensis saponin solution and the crude tea-oil camellia saponin solution are respectively eluted to remove impurities;
3) Eluting the gleditsia sinensis saponin solution and the camellia saponin solution obtained in the step 2) with 25-35% ethanol solution, 40-50% ethanol solution, 55-65% ethanol solution and 70-85% ethanol solution respectively in sequence to obtain a gleditsia sinensis saponin component and a camellia saponin component respectively;
4) And (3) carrying out component recombination on the gleditsia sinensis saponin component and the camellia oleifera saponin component to obtain a compound of the gleditsia sinensis saponin and the camellia oleifera saponin.
2. The method for preparing recombinant gleditsia sinensis saponin according to claim 1, wherein in step 1), deionized water is used as an extractant to extract gleditsia sinensis pericarp to obtain crude gleditsia sinensis saponin solution; and/or extracting the oil tea cake by using methanol as an extracting agent, and filtering and drying to obtain crude oil tea saponin.
3. The preparation method of the recombinant gleditsia sinensis saponin according to claim 2, wherein in the step 1), gleditsia sinensis pericarp is crushed and screened by a 35-40 mesh sieve, deionized water is used as an extracting agent, the solid-liquid ratio is 1:8-10, stirring and extracting are carried out for 6-7 hours, and filtering is carried out to obtain crude gleditsia sinensis saponin solution;
and/or crushing the oil tea cake, sieving with a 20-30 mesh sieve, taking methanol as an extracting agent, stirring and extracting for 6-7 h with a solid-liquid ratio of 1:4-6, filtering and drying to obtain crude oil tea saponin.
4. A process for the preparation of recombinant sapogenin according to any one of claims 1 to 3, wherein in step 2) the washing is carried out sequentially with deionized water and a 10 to 15% ethanol solution.
5. The method for preparing a complex of gleditsia sinensis saponin and camellia oleifera saponin according to claim 4, wherein in the step 2), crude gleditsia sinensis saponin solution is loaded into macroporous adsorption resin AB-8, and is sequentially eluted with deionized water with 2-3 times of resin volume and 5-15% ethanol solution with 2-3 times of resin volume;
and/or loading the crude oil tea saponin solution into macroporous adsorption resin AB-8, and eluting with deionized water with the volume of 2-3 times of the resin volume and 5-15% ethanol solution with the volume of 2-3 times of the resin volume in sequence.
6. The method for preparing a complex of gleditsia sinensis saponin and camellia oleifera saponin according to any one of claims 1 to 5, wherein in step 3), crude gleditsia sinensis saponin is eluted with 30-35% ethanol solution, 45-50% ethanol solution, 55-60% ethanol solution and 70-75% ethanol solution in sequence to obtain gleditsia sinensis saponin component ZS30, gleditsia sinensis saponin component ZS45, gleditsia sinensis saponin component ZS60 and gleditsia sinensis saponin component ZS75;
and/or eluting crude oil tea saponin with 25-30% ethanol solution, 40-45% ethanol solution, 60-65% ethanol solution and 75-85% ethanol solution in sequence to obtain oil tea saponin component YS25, oil tea saponin component YS45, oil tea saponin component YS65 and oil tea saponin component YS85.
7. The method for preparing a complex of gleditsia sinensis saponin and camellia oleifera saponin according to claim 6, wherein in the step 3), the 30-35% ethanol solution is 5-6 times of resin volume, the 45-50% ethanol solution is 10-12 times of resin volume, the 55-60% ethanol solution is 5-6 times of resin volume, and the 70-75% ethanol solution is 2-3 times of resin volume; and/or the number of the groups of groups,
the volume of the 25-30% ethanol solution is 3-4 times of the volume of the resin, the volume of the 40-45% ethanol solution is 8-9 times of the volume of the resin, the volume of the 60-65% ethanol solution is 3-4 times of the volume of the resin, and the volume of the 75-85% ethanol solution is 1.5-2 times of the volume of the resin.
8. The method for preparing a complex of gleditsia sinensis saponin and camellia saponin according to any one of claims 1 to 7, wherein in step 4), the ratio of the gleditsia sinensis saponin component to the camellia saponin component is adjusted, so that the critical micelle concentration and the surface tension of the complex of gleditsia sinensis saponin and camellia saponin are adjustable.
9. A complex of gleditsia sinensis saponin and camellia oleifera saponin, characterized in that it is obtained by the method of preparing a complex of gleditsia sinensis saponin and camellia oleifera saponin according to any one of claims 1-8;
preferably, the compound of the gleditsia sinensis saponin and the camellia oleifera saponin is a compound of one or more of a gleditsia sinensis saponin component ZS30, a gleditsia sinensis saponin component ZS45, a gleditsia sinensis saponin component ZS60, a gleditsia sinensis saponin component ZS75, a camellia oleifera saponin component YS25, a camellia oleifera saponin component YS45, a camellia oleifera saponin component YS65 and a camellia oleifera saponin component YS85.
10. The compound of gleditsia sinensis saponin and tea-oil saponin according to claim 9, wherein the compound of gleditsia sinensis saponin and tea-oil saponin is a compound of tea-oil saponin component YS25, tea-oil saponin component YS45, tea-oil saponin component YS65, tea-oil saponin component YS85, gleditsia sinensis saponin component ZS60 and gleditsia sinensis saponin component ZS75 in a mass ratio of 5-6:28-30:15-18:4-5:8-12:1-2; or the mass ratio of the compound of the gleditsia sinensis saponin to the tea-oil camellia saponin is 1-3:30-32: 18-22:1-3:2-3:1-3 of a complex of gleditsia sinensis saponin component ZS30, gleditsia sinensis saponin component ZS45, gleditsia sinensis saponin component ZS60, gleditsia sinensis saponin component ZS75, tea-oil camellia saponin component YS25 and tea-oil camellia saponin component YS 85;
and/or the surface tension of the complex of the gleditsia sinensis saponin and the camellia saponin is 34.6-41 mN/m, and the critical micelle concentration is 0.1-1.5 g/L.
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