CN101628922A - Oligosaccharide ferulic acid ester preparation method - Google Patents
Oligosaccharide ferulic acid ester preparation method Download PDFInfo
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- CN101628922A CN101628922A CN200910042169A CN200910042169A CN101628922A CN 101628922 A CN101628922 A CN 101628922A CN 200910042169 A CN200910042169 A CN 200910042169A CN 200910042169 A CN200910042169 A CN 200910042169A CN 101628922 A CN101628922 A CN 101628922A
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- ferulic acid
- acid ester
- oligosaccharide
- resin
- raw material
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- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 title claims abstract description 54
- 229940114124 ferulic acid Drugs 0.000 title claims abstract description 54
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 235000001785 ferulic acid Nutrition 0.000 title claims abstract description 54
- 229920001542 oligosaccharide Polymers 0.000 title claims abstract description 54
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 title claims abstract description 54
- -1 Oligosaccharide ferulic acid ester Chemical class 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000007788 liquid Substances 0.000 claims abstract description 41
- 239000002253 acid Substances 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 33
- 229920005989 resin Polymers 0.000 claims abstract description 33
- 239000002994 raw material Substances 0.000 claims abstract description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 238000000108 ultra-filtration Methods 0.000 claims abstract description 9
- 229920002521 macromolecule Polymers 0.000 claims abstract description 7
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000012466 permeate Substances 0.000 claims abstract 3
- 150000002482 oligosaccharides Chemical class 0.000 claims abstract 2
- 239000003957 anion exchange resin Substances 0.000 claims description 27
- 239000000243 solution Substances 0.000 claims description 24
- 235000007164 Oryza sativa Nutrition 0.000 claims description 14
- 240000008042 Zea mays Species 0.000 claims description 14
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 14
- 235000009566 rice Nutrition 0.000 claims description 14
- 235000015099 wheat brans Nutrition 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 12
- 108091005804 Peptidases Proteins 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
- 238000005507 spraying Methods 0.000 claims description 8
- 241000609240 Ambelania acida Species 0.000 claims description 7
- 239000010905 bagasse Substances 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000010298 pulverizing process Methods 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 5
- 108090000790 Enzymes Proteins 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 238000010306 acid treatment Methods 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 235000005822 corn Nutrition 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims 5
- 239000008107 starch Substances 0.000 claims 5
- 239000003480 eluent Substances 0.000 claims 4
- 235000019698 starch Nutrition 0.000 claims 4
- 239000004365 Protease Substances 0.000 claims 2
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 240000007594 Oryza sativa Species 0.000 claims 1
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 102000004139 alpha-Amylases Human genes 0.000 claims 1
- 108090000637 alpha-Amylases Proteins 0.000 claims 1
- 229940024171 alpha-amylase Drugs 0.000 claims 1
- 229940088598 enzyme Drugs 0.000 claims 1
- 239000006227 byproduct Substances 0.000 abstract description 5
- 230000008569 process Effects 0.000 abstract description 5
- 239000003963 antioxidant agent Substances 0.000 abstract description 4
- 230000003078 antioxidant effect Effects 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 239000002910 solid waste Substances 0.000 abstract description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 abstract 3
- 239000003513 alkali Substances 0.000 abstract 2
- 238000002156 mixing Methods 0.000 abstract 1
- 239000006228 supernatant Substances 0.000 abstract 1
- 241000209094 Oryza Species 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 11
- 235000009973 maize Nutrition 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 10
- 239000001913 cellulose Substances 0.000 description 10
- 238000002203 pretreatment Methods 0.000 description 9
- 102000035195 Peptidases Human genes 0.000 description 8
- 230000003544 deproteinization Effects 0.000 description 7
- 150000002605 large molecules Chemical class 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 4
- 210000002421 cell wall Anatomy 0.000 description 3
- 229920001282 polysaccharide Polymers 0.000 description 3
- 239000005017 polysaccharide Substances 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 208000003643 Callosities Diseases 0.000 description 1
- 102000004157 Hydrolases Human genes 0.000 description 1
- 108090000604 Hydrolases Proteins 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000003260 anti-sepsis Effects 0.000 description 1
- 230000002785 anti-thrombosis Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007965 phenolic acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000192 social effect Effects 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
Abstract
本发明公开了一种低聚糖阿魏酸酯的制备方法。制备步骤包括：将纤维质原料预处理后与质量浓度为1.5％的酸液混合，加热，搅拌，过滤，将滤液采用超滤设备去除未酸解的可溶性大分子，得到透过液；将透过液经树脂吸附，用水洗树脂去除低聚糖，再用乙醇水溶液洗脱；将乙醇洗脱液浓缩，干燥，得到低聚糖阿魏酸酯。本发明低聚糖阿魏酸酯具有比阿魏酸更强的抗氧化能力，其纯度高，含量高达90％；树脂在处理后还可经碱处理再生，碱处理液中含有游离阿魏酸，可生产阿魏酸副产品；真空浓缩过程中回收的乙醇可重复利用，从而降低成本；本发明利用农业和食品加工固体废弃物为原料，生产出新型高效功能性抗氧化剂低聚糖阿魏酸酯，经济意义和社会意义重大。The invention discloses a preparation method of oligosaccharide ferulic acid ester. The preparation steps include: pretreating the fibrous raw material and mixing it with an acid solution with a mass concentration of 1.5%, heating, stirring, and filtering the filtrate, using an ultrafiltration device to remove unacidolyzed soluble macromolecules to obtain a permeate; The supernatant is adsorbed by the resin, the resin is washed with water to remove the oligosaccharide, and then eluted with an aqueous ethanol solution; the ethanol eluate is concentrated and dried to obtain the oligosaccharide ferulic acid ester. The oligosaccharide ferulic acid ester of the present invention has a stronger antioxidant capacity than ferulic acid, and its purity is high, and its content is as high as 90%; the resin can also be regenerated by alkali treatment after treatment, and the alkali treatment liquid contains free ferulic acid , can produce ferulic acid by-products; the ethanol recovered in the vacuum concentration process can be reused, thereby reducing costs; the invention uses agricultural and food processing solid waste as raw materials to produce a new type of high-efficiency functional antioxidant oligosaccharide ferulic acid Esters are of great economic and social significance.
Description
Technical field
The invention belongs to field of deep processing of farm products, particularly a kind of preparation method of oligosaccharide ferulic acid ester.
Background technology
Forulic acid is at medicine, food, and there is increasingly extensive purposes in fields such as makeup.It is a kind of good antioxidant, has antithrombotic, functions such as prevention of arterial is atherosis, heart trouble, raising motility of sperm, antisepsis and anti-inflammation.Oligosaccharide ferulic acid ester is the sugared hydroxy esterification on the different positions and the compounds that forms in forulic acid carboxyl and the oligose, its good water solubility.The antioxidation in vitro result of study shows that the resistance of oxidation of oligosaccharide ferulic acid ester is significantly higher than forulic acid and vitamins C.Therefore, oligosaccharide ferulic acid ester can become the new and effective functional antioxidant of a class.
Oligosaccharide ferulic acid ester can obtain by diluted acid or polysaccharide hydrolase degrading plant cell wall material, and this is because forulic acid is mainly crosslinked with cell wall polysaccharides and xylogen by ester bond in plant, thus the part of formation cell walls.
China is grain, sugarcane big producing country, and wheat and rice yield are all approaching or surpass 200,000,000 tons, 1.2 hundred million tons of corns, and 8,500 ten thousand tons of sugarcanes can produce a large amount of cellulosic by products, as wheat bran, bagasse etc. in the results and the course of processing.Phenolic content is 0.5%～4% in these by products, and major part is trans-ferulaic acid (concrete content is decided according to raw material) in the phenolic acid, and especially in the maize peel, trans-ferulaic acid content can account for 3% of maize peel approximately.The preparation that if can utilize these cellulosic by products to carry out oligosaccharide ferulic acid ester can increase these Industrial economic benefit to a certain extent.
At present, oligosaccharide ferulic acid ester can adopt enzymolysis process and acid hydrolyzation to be prepared.Because the lignocellulose compact structure, the hydrolysis efficiency of enzymolysis process is lower, and the present invention adopts acid hydrolyzation, hydrolysis efficiency can be improved ten times.But can produce impurity such as oligose and a spot of free forulic acid in the preparation process, so purifying becomes the bottleneck of preparation oligosaccharide ferulic acid ester from cellulosic, key of the present invention is to solve its issues of purification.
Summary of the invention
In order to solve above-mentioned the deficiencies in the prior art part, the object of the present invention is to provide a kind of preparation method of oligosaccharide ferulic acid ester.This method is passed through cellulose raw materials such as bagasse, maize peel, wheat bran, rice bran or its mixtures, with mass concentration is that 1.5% acid solution is handled, the araboxylan long-chain is cut off at random, generation contains the oligose of forulic acid and does not contain the oligose of forulic acid, and the oligose that adopts the resin adsorption method separation and purification to contain forulic acid promptly gets oligosaccharide ferulic acid ester.
Purpose of the present invention is achieved through the following technical solutions: a kind of preparation method of oligosaccharide ferulic acid ester comprises following operation steps:
(1) diluted acid is handled: will be that 1～2% acid solution is mixed, and stir under heating condition that filtration obtains filtrate and filter residue through pretreated cellulose raw material and mass concentration; Adopt ultrafiltration to remove the soluble large molecule of not acidolysis filtrate, obtain seeing through liquid;
(2) acquisition of oligosaccharide ferulic acid ester: step (1) gained is seen through liquid after resin absorption, wash resin with water and remove oligose; Use the aqueous ethanolic solution wash-out again, obtain ethanol eluate; With the ethanol eluate vacuum concentration, obtain concentrated solution; With the concentrated solution spraying drying, obtain oligosaccharide ferulic acid ester;
The described cellulose raw material of step (1) is more than one in bagasse, maize peel, wheat bran and the rice bran.
The described pre-treatment of step (1) be to cellulose raw material pulverize, destarching and Deproteinization;
Described pulverizing is with the cellulose raw material dry 4h of enzyme that goes out under 105 ℃, is crushed to 80～120 orders.
Described destarching is to be that the mixed of 0.1kg/L is even with the cellulose raw material after pulverizing and water by mass volume ratio, obtains mixed solution; Mixed solution behind 90 ℃ of following gelatinization 30min, is added high temperature resistant α-Dian Fenmei, and the addition of high temperature resistant α-Dian Fenmei is 0.2～0.3% of a mixed solution quality, at 90 ℃ of following enzymolysis 2～3h;
Described Deproteinization is that the temperature with the cellulose raw material behind the destarching is reduced to 65 ℃, add proteolytic enzyme, the addition of proteolytic enzyme be behind the destarching the cellulose raw material quality 1%, reaction 30min after-filtration, washing filter residue 3～5 times obtains pretreated cellulose raw material.
The described acid solution of step (1) is a mineral acid, preferred hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid.The gained filter residue can merge acid treatment with next recycled fibre raw material.
The described mass volume ratio through pretreated cellulose raw material and acid solution of step (1) is 0.05～0.1kg/L.
The temperature of the described heating of step (1) is 60～100 ℃, and the time of stirring is 2～3 hours; The molecular weight cut-off of described ultrafiltration is 3000～10000.
The described resin of step (2) is 3: 1～4: 1 with the solid-liquid volume ratio that sees through liquid; The concentration of volume percent of described aqueous ethanolic solution is 50%～60%.
The described resin of step (2) is a weak base anion-exchange resin; Described washed resin is to end when being washed to water lotion and reaching 8 times of resin volumes; Described ethanol eluate is 5 times of resin volumes; The volume of described concentrated solution is 1/20～1/40 of an ethanol eluate volume.
The preferred D301 macroporous weakly basic anion exchange resin of described resin.
The described simmer down to vacuum concentration of step (2), thickening temperature is 40 °～60C; Described drying is a spraying drying, and drying temperature is 80 ℃～100 ℃.
Scientific basis of the present invention is as follows: the trans-ferulaic acid in the cellulosic mainly combines with polysaccharide and xylogen with ester bond, adopt acid treatment can disconnect more weak glycosidic link, keep most of forulic acid ester bond simultaneously, thereby formed the oligosaccharide ferulic acid ester that sugar chain length differs.In the acid treatment process, the sugar chain section that does not contain forulic acid by acidolysis after, form oligose; In addition, a spot of forulic acid ester bond forms the forulic acid of free state also by acidolysis.Oligosaccharide ferulic acid ester and free forulic acid can be retained on the resin by the absorption of D301 macroporous weakly basic anion exchange resin, and the oligose that does not contain forulic acid is removed through washing, again by the D301 resin to the free stronger basis of forulic acid adsorptive power, the ethanolic soln oligosaccharide ferulic acid ester that adsorptive power is more weak of employing 60% elutes, thereby obtains highly purified oligosaccharide ferulic acid ester solution.Solution is removed most of ethanol through vacuum concentration, and last spraying drying can obtain highly purified oligosaccharide ferulic acid ester solid phase prod.
The relative prior art of the present invention has following advantage and beneficial effect: the oligosaccharide ferulic acid ester that (1) obtains has the resistance of oxidation stronger than forulic acid; (2) the oligosaccharide ferulic acid ester purity height of Huo Deing, its content reaches more than 90%; (3) the D301 macroporous weakly basic anion exchange resin can be regenerated through alkaline purification, contains free forulic acid in the alkaline purification liquid, can produce the forulic acid byproduct; (4) ethanol that reclaims in the vacuum Concentrating Process can reuse, thereby reduces cost; (5) the present invention utilizes agricultural and food-processing solid waste to be raw material, produces new and effective functional antioxidant---the oligosaccharide ferulic acid ester of industries such as can be applicable to food, medicine, makeup, and economic implications and social effect are great.
Embodiment
The present invention is described in further detail below in conjunction with embodiment, but embodiments of the present invention are not limited thereto.
Embodiment 1: utilize maize peel to prepare oligosaccharide ferulic acid ester
(1) pre-treatment of raw material:
Get 1 kg corn skin, the dry 4h of the enzyme that goes out under 105 ℃ is crushed to 80 orders with pulverizer; Maize peel after pulverizing is added 10 premium on currency, mix, behind 90 ℃ of following gelatinization 30min, add high temperature resistant α-Dian Fenmei, the addition of high temperature resistant α-Dian Fenmei is 0.2% of a mixed solution quality, at 90 ℃ of following enzymolysis 3h; The temperature of the maize peel behind the destarching is reduced to 65 ℃, adds proteolytic enzyme, the addition of proteolytic enzyme is 1% of a maize peel quality, reaction 30min; Maize peel behind the Deproteinization is filtered, and washing filter residue 3 times obtains pretreated maize peel.
(2) diluted acid is handled:
Will be through pretreated maize peel by 1 kilogram of solid-to-liquid ratio: the combined of 15 liters (being mass volume ratio 0.067kg/L) and mass concentration 1.5%, constantly stir, handled 3 hours for 100 ℃, filter; Is that 5000 ultrafiltration apparatus is further removed not the soluble large molecule of acidolysis fully with gained filtrate with molecular weight cut-off, obtains seeing through liquid;
(3) acquisition of highly purified oligosaccharide ferulic acid ester:
Step (2) gained is seen through liquid to be handled with the D301 macroporous weakly basic anion exchange resin, the pre-treatment according to the following steps earlier of D301 macroporous weakly basic anion exchange resin: the mass percent concentration that adds 3～5 times of resin volumes is that 5%NaOH stirred 24 hours in resin, be washed till neutrality with distilled water then, the 5%HCl that adds 3～5 times of volumes again stirred 4 hours, be washed till pH=1～3 with distilled water, standby;
It is as follows with D301 macroporous weakly basic anion exchange resin treatment step to see through liquid: the D301 macroporous weakly basic anion exchange resin is installed in the chromatography column, add and see through liquid, the D301 macroporous weakly basic anion exchange resin is 3: 1 with the solid-liquid volume ratio that sees through liquid, the liquid of crossing behind the chromatography column that sees through abandons, chromatography column cleans with the distilled water of 8 times of resin volumes simultaneously, use the aqueous ethanolic solution wash-out of the percent by volume 60% of 5 times of resin volumes then, obtain ethanol eluate;
Above-mentioned ethanol eluate vacuum concentration under 40 ℃ of conditions is carried out spraying drying to 1/20 of original volume under 80 ℃ of conditions, obtain highly purified oligosaccharide ferulic acid ester solid phase prod.
Embodiment 2: utilize wheat bran to prepare oligosaccharide ferulic acid ester
(1) pre-treatment of raw material:
Get 1 kilogram of wheat bran, the dry 4h of the enzyme that under 105 ℃, goes out, pulverizer is crushed to 120 orders; Wheat bran after pulverizing is added 10 premium on currency mix, behind 90 ℃ of following gelatinization 30min, add high temperature resistant α-Dian Fenmei, the addition of high temperature resistant α-Dian Fenmei is 0.3% of a mixed solution quality, at 90 ℃ of following enzymolysis 2h, obtains the wheat bran of destarching; The wheat bran temperature of above-mentioned destarching is reduced to 65 ℃, adds proteolytic enzyme, the addition of proteolytic enzyme is 1% of a wheat bran quality, reacts 30min, obtains the wheat bran of Deproteinization; The wheat bran of above-mentioned Deproteinization is filtered, and washing filter residue 4 times obtains pretreated wheat bran.
(2) diluted acid is handled:
Through pretreated wheat bran by 1 kilogram of solid-to-liquid ratio: 20 liters (being mass volume ratio 0.05kg/L) mix with the aqueous sulfuric acid of mass concentration 1%, constantly stir, and handle 2 hours for 60 ℃, filter, and obtain filtrate and filter residue;
Gained filtrate is that 10000 ultrafiltration apparatus is further removed not the soluble large molecule of acidolysis fully with molecular weight cut-off, obtains seeing through liquid.
(3) acquisition of highly purified oligosaccharide ferulic acid ester:
Step (2) gained is seen through liquid to be handled with the D301 macroporous weakly basic anion exchange resin; The pre-treatment according to the following steps earlier of D301 macroporous weakly basic anion exchange resin: the 5%NaOH that adds 3～5 times of volumes stirred 24 hours in resin, be washed till neutrality with distilled water then, the 5%HCl that adds 3～5 times of volumes again stirred 4 hours, was washed till pH=1～3 with distilled water, and is standby.
It is as follows with D301 macroporous weakly basic anion exchange resin treatment step to see through liquid: the D301 macroporous weakly basic anion exchange resin is installed in the chromatography column, add and see through liquid, the D301 macroporous weakly basic anion exchange resin is 4: 1 with the solid-liquid volume ratio that sees through liquid, the liquid of crossing behind the chromatography column that sees through abandons, chromatography column cleans with the distilled water of 8 times of resin volumes simultaneously, use the percent by volume 50% aqueous ethanolic solution wash-out of 5 times of resin volumes then, obtain ethanol eluate;
With ethanol eluate vacuum concentration under 60 ℃ of conditions to original volume 1/40 after, under 100 ℃ of conditions, carry out spraying drying and obtain highly purified oligosaccharide ferulic acid ester solid phase prod.
Embodiment 3: utilize bagasse to prepare oligosaccharide ferulic acid ester
(1) pre-treatment of raw material:
Get bagasse after pulverizer is crushed to 100 orders, dry 4h under 105 ℃.
(2) diluted acid is handled and is obtained thick oligosaccharide ferulic acid ester:
Through pretreated bagasse by 1 kilogram of solid-to-liquid ratio: 10 liters (being mass volume ratio 0.1kg/L) mix with the aqueous nitric acid of mass concentration 2%, constantly stir, and handle 2.5 hours for 80 ℃, filter, and obtain filter residue and filtrate;
Is that 3000 ultrafiltration apparatus is further removed not the soluble large molecule of acidolysis fully with gained filtrate with molecular weight cut-off, obtains seeing through liquid;
(3) acquisition of highly purified oligosaccharide ferulic acid ester:
Step (2) gained is seen through liquid to be handled with the D301 macroporous weakly basic anion exchange resin.The pre-treatment according to the following steps earlier of D301 macroporous weakly basic anion exchange resin: the 5%NaOH that adds 3～5 times of volumes stirred 24 hours in the D301 macroporous weakly basic anion exchange resin, be washed till neutrality with distilled water then, the 5%HCl that adds 3～5 times of volumes again stirred 4 hours, be washed till pH=1～3 with distilled water, standby.
It is as follows with D301 macroporous weakly basic anion exchange resin treatment step to see through liquid: the D301 macroporous weakly basic anion exchange resin is installed in the chromatography column, add and see through liquid, the D301 macroporous weakly basic anion exchange resin is 3: 1 with the solid-liquid volume ratio that sees through liquid, the liquid of crossing behind the chromatography column that sees through abandons, chromatography column cleans with the distilled water of 8 times of resin volumes simultaneously, use the percent by volume 55% aqueous ethanolic solution wash-out of 5 times of resin volumes then, obtain the aqueous ethanolic solution wash-out;
With above-mentioned aqueous ethanolic solution wash-out liquid vacuum concentration under 50 ℃ of conditions to original volume 1/30 after, under 90 ℃ of conditions, carry out spraying drying and obtain highly purified oligosaccharide ferulic acid ester solid phase prod.
Embodiment 4: utilize rice bran to prepare oligosaccharide ferulic acid ester
(1) pre-treatment of raw material:
Get 1 kilogram of rice bran, the dry 4h of the enzyme that under 105 ℃, goes out, pulverizer is crushed to 120 orders; Rice bran after pulverizing is added 10 premium on currency mix, behind 90 ℃ of following gelatinization 30min, add high temperature resistant α-Dian Fenmei, the addition of high temperature resistant α-Dian Fenmei is 0.3% of a mixed solution quality, at 90 ℃ of following enzymolysis 3h, obtains the rice bran of destarching; The rice bran temperature of above-mentioned destarching is reduced to 65 ℃, adds proteolytic enzyme, the addition of proteolytic enzyme is 1% of a rice bran quality, reacts 30min, obtains the rice bran of Deproteinization; The rice bran of above-mentioned Deproteinization is filtered, and washing filter residue 5 times obtains pretreated rice bran.
(2) diluted acid is handled:
Through pretreated rice bran by 1 kilogram of solid-to-liquid ratio: 15 liters (being mass volume ratio 0.067kg/L) mix with the phosphate aqueous solution of mass concentration 1.5%, constantly stir, and handle 2 hours for 60 ℃, filter, and obtain filtrate and filter residue;
Gained filtrate is that 10000 ultrafiltration apparatus is further removed not the soluble large molecule of acidolysis fully with molecular weight cut-off, obtains seeing through liquid.
(3) acquisition of highly purified oligosaccharide ferulic acid ester:
Step (2) gained is seen through liquid to be handled with the D301 macroporous weakly basic anion exchange resin; The pre-treatment according to the following steps earlier of D301 macroporous weakly basic anion exchange resin: the 5%NaOH that adds 3～5 times of volumes stirred 24 hours in resin, be washed till neutrality with distilled water then, the 5%HCl that adds 3～5 times of volumes again stirred 4 hours, was washed till pH=1～3 with distilled water, and is standby.
It is as follows with D301 macroporous weakly basic anion exchange resin treatment step to see through liquid: the D301 macroporous weakly basic anion exchange resin is installed in the chromatography column, add and see through liquid, the D301 macroporous weakly basic anion exchange resin is 4: 1 with the solid-liquid volume ratio that sees through liquid, the liquid of crossing behind the chromatography column that sees through abandons, chromatography column cleans with the distilled water of 8 times of resin volumes simultaneously, use the percent by volume 50% aqueous ethanolic solution wash-out of 5 times of resin volumes then, obtain ethanol eluate;
With ethanol eluate vacuum concentration under 60 ℃ of conditions to original volume 1/25 after, under 80 ℃ of conditions, carry out spraying drying and obtain highly purified oligosaccharide ferulic acid ester solid phase prod.
The foregoing description is a preferred implementation of the present invention; but embodiments of the present invention are not restricted to the described embodiments; other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102181489A (en) * | 2011-03-14 | 2011-09-14 | 盐城工学院 | Method for preparing ferulic acid and oligosaccharide by producing enzymes from Salicornia bigelovii straws fermented by Aureobasidium pullulans |
| CN104448057A (en) * | 2014-12-17 | 2015-03-25 | 桂林理工大学 | Preparation method of nano-scale ferulic acid bagasse xylan ester |
| CN108277245A (en) * | 2017-12-28 | 2018-07-13 | 保龄宝生物股份有限公司 | A kind of preparation process of high-purity oligosaccharide ferulic acid ester |
| CN108753873A (en) * | 2018-06-15 | 2018-11-06 | 河南工业大学 | A method of the oligomeric sugar ester of wheat bran ferulic acid is prepared based on positioning digestion collaboration processing |
| CN111358798A (en) * | 2020-03-13 | 2020-07-03 | 暨南大学 | New application of oligosaccharide ferulate |
| CN113925160A (en) * | 2021-09-24 | 2022-01-14 | 盐城工学院 | A kind of microcapsule with antioxidant and preparation method thereof |
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| CN1840673A (en) * | 2006-01-19 | 2006-10-04 | 江南大学 | A method of enzymolyzing wheat bran to prepare feruloyl oligosaccharides |
| CN101191137B (en) * | 2007-12-26 | 2010-11-03 | 江南大学 | Method for synthesizing feruloylated oligosaccharides by biological catalysis |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102181489A (en) * | 2011-03-14 | 2011-09-14 | 盐城工学院 | Method for preparing ferulic acid and oligosaccharide by producing enzymes from Salicornia bigelovii straws fermented by Aureobasidium pullulans |
| CN104448057A (en) * | 2014-12-17 | 2015-03-25 | 桂林理工大学 | Preparation method of nano-scale ferulic acid bagasse xylan ester |
| CN108277245A (en) * | 2017-12-28 | 2018-07-13 | 保龄宝生物股份有限公司 | A kind of preparation process of high-purity oligosaccharide ferulic acid ester |
| CN108753873A (en) * | 2018-06-15 | 2018-11-06 | 河南工业大学 | A method of the oligomeric sugar ester of wheat bran ferulic acid is prepared based on positioning digestion collaboration processing |
| CN111358798A (en) * | 2020-03-13 | 2020-07-03 | 暨南大学 | New application of oligosaccharide ferulate |
| CN113925160A (en) * | 2021-09-24 | 2022-01-14 | 盐城工学院 | A kind of microcapsule with antioxidant and preparation method thereof |
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