CN106083940A - A kind of method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus - Google Patents
A kind of method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus Download PDFInfo
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- CN106083940A CN106083940A CN201610539313.3A CN201610539313A CN106083940A CN 106083940 A CN106083940 A CN 106083940A CN 201610539313 A CN201610539313 A CN 201610539313A CN 106083940 A CN106083940 A CN 106083940A
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- fructus aurantii
- aurantii immaturus
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- 239000010135 fructus aurantii immaturus Substances 0.000 title claims abstract description 64
- 238000000034 method Methods 0.000 title claims abstract description 37
- QUQPHWDTPGMPEX-UTWYECKDSA-N aurantiamarin Natural products COc1ccc(cc1O)[C@H]1CC(=O)c2c(O)cc(O[C@@H]3O[C@H](CO[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O)[C@H]4O)[C@@H](O)[C@H](O)[C@H]3O)cc2O1 QUQPHWDTPGMPEX-UTWYECKDSA-N 0.000 title claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000005189 flocculation Methods 0.000 claims abstract description 39
- 230000016615 flocculation Effects 0.000 claims abstract description 39
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- ARGKVCXINMKCAZ-UZRWAPQLSA-N neohesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O[C@H]3[C@@H]([C@H](O)[C@@H](O)[C@H](C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UZRWAPQLSA-N 0.000 claims abstract description 33
- 238000000605 extraction Methods 0.000 claims abstract description 28
- 102000004190 Enzymes Human genes 0.000 claims abstract description 25
- 108090000790 Enzymes Proteins 0.000 claims abstract description 25
- 239000007788 liquid Substances 0.000 claims abstract description 20
- 238000001728 nano-filtration Methods 0.000 claims abstract description 19
- 239000002131 composite material Substances 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 14
- 238000002425 crystallisation Methods 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000000047 product Substances 0.000 claims abstract description 14
- 241000196324 Embryophyta Species 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 13
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 13
- 238000005406 washing Methods 0.000 claims abstract description 13
- 244000183685 Citrus aurantium Species 0.000 claims abstract description 10
- 235000007716 Citrus aurantium Nutrition 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000001291 vacuum drying Methods 0.000 claims abstract description 9
- 238000004321 preservation Methods 0.000 claims abstract description 6
- 229940088598 enzyme Drugs 0.000 claims description 24
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 14
- 238000000746 purification Methods 0.000 claims description 13
- 229930182470 glycoside Natural products 0.000 claims description 11
- 150000002338 glycosides Chemical class 0.000 claims description 11
- 238000007654 immersion Methods 0.000 claims description 9
- 239000012141 concentrate Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 239000000292 calcium oxide Substances 0.000 claims description 7
- 235000012255 calcium oxide Nutrition 0.000 claims description 7
- 239000012528 membrane Substances 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- 108091005804 Peptidases Proteins 0.000 claims description 5
- 239000004365 Protease Substances 0.000 claims description 5
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical group [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims description 5
- 108010059892 Cellulase Proteins 0.000 claims description 4
- 229940106157 cellulase Drugs 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- -1 wherein Proteins 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
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- 239000000843 powder Substances 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 7
- 230000003311 flocculating effect Effects 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 6
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- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 description 3
- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 description 3
- APSNPMVGBGZYAJ-GLOOOPAXSA-N clematine Natural products COc1cc(ccc1O)[C@@H]2CC(=O)c3c(O)cc(O[C@@H]4O[C@H](CO[C@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)cc3O2 APSNPMVGBGZYAJ-GLOOOPAXSA-N 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 229940025878 hesperidin Drugs 0.000 description 3
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 description 3
- VUYDGVRIQRPHFX-UHFFFAOYSA-N hesperidin Natural products COc1cc(ccc1O)C2CC(=O)c3c(O)cc(OC4OC(COC5OC(O)C(O)C(O)C5O)C(O)C(O)C4O)cc3O2 VUYDGVRIQRPHFX-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000011031 large-scale manufacturing process Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 description 2
- 229930019673 naringin Natural products 0.000 description 2
- 229940052490 naringin Drugs 0.000 description 2
- 229940105623 neo-synephrine Drugs 0.000 description 2
- 235000010987 pectin Nutrition 0.000 description 2
- 229920001277 pectin Polymers 0.000 description 2
- 239000001814 pectin Substances 0.000 description 2
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- YRCWQPVGYLYSOX-UHFFFAOYSA-N synephrine Chemical compound CNCC(O)C1=CC=C(O)C=C1 YRCWQPVGYLYSOX-UHFFFAOYSA-N 0.000 description 2
- OBDQFFPGPQKMDW-UHFFFAOYSA-N CNCCC1=CC=C(C=C1)O.CNCCC1=CC=C(C=C1)O Chemical compound CNCCC1=CC=C(C=C1)O.CNCCC1=CC=C(C=C1)O OBDQFFPGPQKMDW-UHFFFAOYSA-N 0.000 description 1
- 102100034279 Calcium-binding mitochondrial carrier protein Aralar2 Human genes 0.000 description 1
- 235000010946 Castanopsis cuspidata Nutrition 0.000 description 1
- 244000088646 Castanopsis cuspidata Species 0.000 description 1
- 235000000228 Citrus myrtifolia Nutrition 0.000 description 1
- 241001672694 Citrus reticulata Species 0.000 description 1
- 235000016646 Citrus taiwanica Nutrition 0.000 description 1
- 241001522083 Citrus trifoliata Species 0.000 description 1
- 239000001329 FEMA 3811 Substances 0.000 description 1
- XYXONTIQGZKCNH-UYKXVWJOSA-N Lonicerin Natural products CO[C@@H]1O[C@@H](O)[C@H]([C@H]2C[C@H](O)[C@H](C)[C@@H]12)C(=O)OC XYXONTIQGZKCNH-UYKXVWJOSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 235000000404 Poncirus trifoliata Nutrition 0.000 description 1
- 241001093501 Rutaceae Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- SHPPXMGVUDNKLV-UHFFFAOYSA-N Veronicastroside Natural products OC1C(O)C(O)C(C)OC1OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 SHPPXMGVUDNKLV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- RPMNUQRUHXIGHK-PYXJVEIZSA-N apigenin 7-O-neohesperidoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 RPMNUQRUHXIGHK-PYXJVEIZSA-N 0.000 description 1
- 229930034861 apigenin-7-O-neohesperidoside Natural products 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 108010084210 citrin Proteins 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 230000004345 fruit ripening Effects 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- SHPPXMGVUDNKLV-KMFFXDMSSA-N luteolin 7-O-neohesperidoside Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 SHPPXMGVUDNKLV-KMFFXDMSSA-N 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical group C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 description 1
- 229940089953 neohesperidin dihydrochalcone Drugs 0.000 description 1
- 235000010434 neohesperidine DC Nutrition 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229960003684 oxedrine Drugs 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- RPMNUQRUHXIGHK-SBDOOABHSA-N rhoifolin Natural products O([C@@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1Oc1cc(O)c2C(=O)C=C(c3ccc(O)cc3)Oc2c1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1 RPMNUQRUHXIGHK-SBDOOABHSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- 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
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
A kind of method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus, comprises the following steps: (1) is soaked in water after being pulverized by immature bitter orange raw material, adds composite plant hydrolytic enzyme preparation and carries out enzymolysis, obtains enzymolysis Fructus Aurantii Immaturus；(2) by the heating extraction of enzymolysis Fructus Aurantii Immaturus, cooling, centrifugal, filter, obtain the enzyme-added lixiviating solution of Fructus Aurantii Immaturus；(3) by enzyme-added for Fructus Aurantii Immaturus lixiviating solution water bath heat preservation, add flocculant, flocculation treatment, be centrifuged, filter, obtain Fructus Aurantii Immaturus flocculation liquid；(4) Fructus Aurantii Immaturus is flocculated liquid nanofiltration, concentration, vacuum drying, obtain neohesperidin crude product；(5) neohesperidin crude product ethanol solution fully dissolved and tightly filters, then repeating crystallisation by cooling and washing, vacuum drying, obtain high purity novel aurantiamarin product.98.6% is may be up to, ultimate yield ＞ 90% according to the inventive method products obtained therefrom purity；The inventive method technique is simple, strong operability, energy consumption, low cost, is suitable for industrialized production, and Residual ethanol is low, Environmental Safety.
Description
Technical field
The present invention relates to a kind of method extracting high purity novel aurantiamarin, be specifically related to one be applicable to industrial from
The method extracting high purity novel aurantiamarin in Fructus Aurantii Immaturus.
Background technology
Fructus Aurantii Immaturus, belongs to rutaceae, extensive at distribution in China, is China's tradition address to Citrus aurantium Linn., at Chinese tradition
The world of medicine, Fructus Aurantii Immaturus, as traditional traditional herbal medicine, is mainly used to appetite strengthening and conditioning gas (energy).In Italy, Fructus Aurantii Immaturus
Also it has been one of Traditional Folk prescription since 16th century, is used to treatment and as calentura such as malaria and uses as antibacterial.In the recent period
Research confirms, Fructus Aurantii Immaturus can replace Herba Ephedrae to treat obesity, not have bad cardiovascular aspect side effect simultaneously.
Modern study finds, ripe Fructus Aurantii Immaturus (hesperidin) Han Hesperidin, outermost layer of skin glycosides (naringin), Neosynephrine
(synephrine), N-methyltyramine (N-methyltyramine).Containing naringin during fruit immaturity, Radix seu Folium Tosicodendri Delavayi glucoside
(rhoifolin), xylostein (lonicerin), neohesperidin (neohesperidin), the neohesperidin when fruit maturation
Disappear.Neohesperidin has cures the effect that in the fragility of blood capillary and blood plasma, protein permeability is too high, is once referred to as maintaining
The vitamin of capillary permeability or Citrin；It is neohesperidin dihydrochalcone after its hydrogenation, belongs to novel sweetener,
Sugariness is about 1000 times of sucrose.
CN105399787A discloses a kind of extraction Hesperidin, neohesperidin and method of Neosynephrine from peel of Citrus reticulata Blanco, fruit,
It is by Fructus Aurantii Immaturus fruitlet drying, pulverizing, seepage pressure effects, takes percolate and cross highly acid styrene type cation seperation column, washing, enter macropore
Adsorption resin column, washing, 20% low-carbon alcohols washing, 70% low-carbon alcohols washing, take washing liquid and concentrate, help analysis, crystallization, recrystallization, obtain
Neohesperidin product.But, its process route is complicated, operation is many, and production difficulty is big, wayward, production cost is high, is not suitable for
Large-scale production.
CN104587014A discloses a kind of method of flavonoids effective constituent extracted in Chinese medicine Fructus Aurantii, is to take Fructus Aurantii medicine
Material powder and florisil silica, with mass ratio 1:1～4 mixing, add in mortar and grind；Take solid-phase extraction column, solid-phase extraction column
Bottom add sieve plate, the solid mixture after grinding adds in solid-phase extraction column, and filler tamps rear top and adds sieve plate,
The solid-phase extraction column filled in is placed on solid-phase extracting instrument, takes eluant, inject in solid-phase extraction column, open solid-phase extracting instrument
Air pump, carries out eluting to solid-phase extraction column, collects eluent, after eluting terminates, by eluent vortex, is centrifuged, takes upper strata clear
Liquid is flavonoids effective constituent extracting solution.But, obtained is the mixture of a kind of low content, and it extracts discontinuous,
Use type of feed, complex procedures and be unfavorable for large-scale production.
CN103833803A discloses a kind of method of sweeting agent in ultrasonic extraction and resin purification Pasania cuspidata leaf, is to use
Ultrasonic wave added soak with ethanol is extracted, and wherein, ultrasound wave optimum extraction condition is: concentration of alcohol is 70%, and solid-to-liquid ratio is 1:25, super
The sound wave time is 35min；AB-8 resin optimal purifying process condition is: adsorption flow rate is 0.5mL/min, and eluting concentration of alcohol is
90%, elution volume is 1.875BV, and eluant flow velocity is 1mL/min.But, extract at this and under purification condition, neohesperidin
Purity to be only in 71.8226%, and this technology the amount of alcohol used big, cause large-scale production disposably to put into greatly, produce into
This height.
Summary of the invention
The technical problem to be solved is, overcomes the drawbacks described above that prior art exists, it is provided that a kind of product is received
Rate is high, purity is high, and technique is simple, and energy consumption is low, environment friendly and pollution-free, and the extraction high-purity from Fructus Aurantii Immaturus being suitable for industrialized production is the most orange
The method of skin glycosides.
The technical solution adopted for the present invention to solve the technical problems is as follows: a kind of extraction new Pericarpium Citri junoris of high-purity from Fructus Aurantii Immaturus
The method of glycosides, it is characterised in that comprise the following steps:
(1) enzyme-added immersion: after immature bitter orange raw material is pulverized, be soaked in water, be subsequently adding composite plant hydrolytic enzyme preparation and carry out enzyme
Solve, obtain enzymolysis Fructus Aurantii Immaturus；
(2) heating extraction: by the heating extraction of step (1) gained enzymolysis Fructus Aurantii Immaturus, cool down, centrifugal, filter, obtain the enzyme-added extraction of Fructus Aurantii Immaturus
Liquid；
(3) flocculation purification: the enzyme-added lixiviating solution of step (2) gained Fructus Aurantii Immaturus carries out water bath heat preservation, adds flocculant, stirring, carries out
After flocculation treatment, centrifugal, filter, obtain Fructus Aurantii Immaturus flocculation liquid；
(4) nanofiltration, concentrate, be dried: by step (3) gained Fructus Aurantii Immaturus flocculation liquid carry out nanofiltration, concentrate, vacuum drying, obtain new Pericarpium Citri junoris
Glycosides crude product；
(5) alcohol phase crystallizing and drying: by step (4) gained neohesperidin crude product, fully dissolve with ethanol solution and tightly filter, so
After repeat crystallisation by cooling and washing, vacuum drying, obtain high purity novel aurantiamarin product.
In step (1), the total glycosides mass content of described Fructus Aurantii Immaturus is 20～30%, and neohesperidin mass content is 9～15%.
Further, in step (1), the particle diameter after described immature bitter orange raw material is pulverized is 10～30 mesh；Described immature bitter orange raw material and water
Feed liquid mass ratio be 1:2.5～3.5.Finding in inventor's experimentation, when water consumption for immersion is less than 2.5 times, raw material soaks
Almost without feed liquid after profit, after enzyme adds, hydrolysis result is poor, when water consumption for immersion is more than 3.5 times, when enzyme dosage is identical, and enzyme concentration
Declining, hydrolysis result is poor.
Further, in step (1), described composite plant hydrolytic enzyme preparation is cellulase, pectase and protease
Compound enzyme, wherein, cellulase: pectase: the mass ratio of protease is 2～3:1～2:0.5～1.0.
Further, in step (1), the quality (g) that described composite plant hydrolytic enzyme preparation adds is water volume (mL)
0.01～0.03w/v%(preferably 0.015～0.020w/v%).The addition of described composite plant hydrolytic enzyme preparation, beneficially Fructus Aurantii Immaturus
Raw material cell wall broken, the degraded of pectin albumen etc., thus the dissolution of beneficially neohesperidin, if but addition is less than 0.01
W/v%, can cause hydrolysis result to decline, and addition promotes without positive effect higher than 0.03 w/v%, continues to increase enzyme dosage
Only enzyme preparation can be lost.
Further, in step (1), the temperature of described enzymolysis is 40～50 DEG C, and the time of enzymolysis is 120～180min.Institute
Stating under hydrolysis temperature, composite plant hydrolytic enzyme preparation enzymolysis activity is optimal；After enzymolysis time is less than 120min, hydrolysis result is not
Fully；When enzymolysis time is more than after 180min, enzymolysis efficiency tends to be steady state, and yield increases hardly, continues to extend and extracts
Time is meaningless.
Further, in step (2), described extraction is Continuous Countercurrent Extraction, the temperature of extraction be 80～95 DEG C (preferably 88～
90 DEG C), the time of extraction is 60～120min.
Further, in step (2), extraction adds quality is immature bitter orange raw material quality 6～8 times of water.If water consumption for immersion
Less than 6 times, then neohesperidin yield can drastically decline, and water consumption higher than neohesperidin yields after 8 times almost without increase, then
Continue to increase water consumption meaningless.
In step (2), in order to reduce energy consumption further, described cooling only need to cool the temperature to step (3) flocculation purification institute
Need temperature.
In step (2), described being centrifuged as tripodia sedimentation and centrifugation, centrifugation rate is 1000～1500r/min.
Further, in step (3), described flocculant is iron chloride and quick lime, after first using iron chloride flocculation treatment, then uses
Quick lime flocculation treatment, the temperature of twice flocculation treatment is 40～60 DEG C, and the time of flocculation treatment is 60～80min.Institute
Stating Flocculating Effect of Flocculant good, cheap, addition is few, meets industrial needs.
Further, in step (3), the consumption of described every kind of flocculant is 1.5～3.0g/L.Flocculant adds the most, former
Material loss is the biggest, and when addition is more than 3.0g/L, loss rate occurs that flex point, loss rate steeply rise, and flocculating effect exists
Without being obviously improved after 3.0g/L, when addition is less than 1.5g/L, flocculating effect can not reach purpose of flocculating, at described addition
Under, flocculation solution shows slightly alkalescence, and loss rate is few.Inventor studies discovery, when water temperature 40～60 DEG C, flocculation time be 60～
During 80min, flocculating effect the most in the same horizontal line, but along with flocculation time extend, flocculation loss rate have larger difference, for
Ensureing product yield and keep the balance of flocculating effect, loss rate of flocculating under described temperature and time is minimum.
In step (3), described being centrifuged is centrifuged for first carrying out sleeping spiral shell, and centrifugation rate is 2500～3500r/min, then carries out dish
Formula is centrifuged, and centrifugation rate is 5000～7000r/min.
Further, in step (4), the molecular cut off of NF membrane used by described nanofiltration is 5000～8000Da, operation pressure
Power is 1.0～1.5MPa, and temperature of charge is 10～25 DEG C, and nanofiltration is to the μ s/cm of filter liquor electrical conductivity≤500；Described concentration
For being concentrated in vacuo, vacuum pressure is-0.09～-0.07MPa, and temperature is 50～80 DEG C, and being concentrated into concentrated solution quality is raw material matter
Till the 40～50% of amount.Described NF membrane preferred Tao Shi DOW NF90-400 type NF membrane, the effect of nanofiltration be isolated and purified,
Decolour, except inorganic salt, concentration etc..
Further, in step (5), the volume fraction of described ethanol solution is 70～90%；The consumption of described ethanol solution is
Every 100mL ethanol dissolves neohesperidin crude product 40～60g；The temperature of described dissolving is 50～70 DEG C.
Further, in step (5), the temperature of described crystallisation by cooling is 2～5 DEG C, number of repetition >=2 time；With 2～5 DEG C
Frozen water washs, and each washings consumption is 1～2 times of crystal volume.
Having the beneficial effect that of the inventive method:
(1) the high purity novel aurantiamarin product shows white extracted according to the inventive method or beige white powder shape, through high-efficient liquid
Phase chromatography detects, and the purity of gained neohesperidin may be up to 98.6%, and impurity content is few, the ultimate yield ＞ of neohesperidin
90%；
(2) method that the inventive method uses enzyme-added immersion, heating extraction, flocculation purification to combine is greatly improved new Pericarpium Citri junoris
The maximum leaching content of glycosides, makes the impurity in Fructus Aurantii Immaturus flocculate simultaneously, facilitates subsequent purification；
(3) the inventive method uses NF membrane to slough substantial amounts of as miscellaneous in pectin, albumen, pigment, small organic molecule, inorganic salt etc.
Matter, does not only reach the purpose of purification, and is concentrated while purification, the most to a certain degree reduces the follow-up energy being concentrated in vacuo
Consumption, reduces production cost, hence it is evident that the method being better than the macroreticular resin absorbing method purification neohesperidin of existing routine；
(4) only using pure water in the inventive method extraction before crystallization, purge process, technique is simple, and low cost is operable
Property strong, be suitable for industrialized production, edible ethanol residual quantity in the final product controls at 100 below ppm, relative to existing
The harmful organic solvent that technology is used is more environment-friendly and safer.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is described in further detail.
The Fructus Aurantii Immaturus dry fruit (being 21.37% containing total glycosides, neohesperidin 10.27%) that the embodiment of the present invention is used is commercially available, produces
Jiangxi, ground；The model of the composite hydrolysis enzyme preparation used is: Novi letter composite plant hydrolytic enzyme Viscozyme L, wherein, fine
Dimension element enzyme: pectase: the mass ratio of protease is 2.5:1.5:0.8, is purchased from lucky precious (Qingdao) bio tech ltd；Made
NF membrane be Tao Shi DOW NF90-400 type NF membrane, be purchased from film water treatment equipment company limited of Guangzhou China；Crystallization is made
The food grade materials that ethanol is volume fraction 95%；Other chemical reagent used, if no special instructions, all by often
Rule are either commercially available.
Embodiment 1
(1) enzyme-added immersion: after 500g Fructus Aurantii Immaturus dry powder is broken to 10～30 mesh, is soaked in 1250mL water, is subsequently adding
0.125g composite plant hydrolytic enzyme preparation, at 40 DEG C, enzymolysis 120min, obtain enzymolysis Fructus Aurantii Immaturus；
(2) heating extraction: add 3kg water in step (1) gained enzymolysis Fructus Aurantii Immaturus, at 80 DEG C, continuous flow upstream extraction 60min,
It is cooled to 45 DEG C, under 1200r/min speed, carries out tripodia sedimentation and centrifugation, filter, obtain the enzyme-added lixiviating solution of 3020mL Fructus Aurantii Immaturus；
(3) flocculation purification: the enzyme-added lixiviating solution of 3020mL step (2) gained Fructus Aurantii Immaturus carries out water bath heat preservation, adds 6.0g iron chloride,
Stirring, at 45 DEG C, after flocculation treatment 60min, adds 6.0g quick lime, stirring, at 45 DEG C, after flocculation treatment 60min,
Under 3000r/min speed, carry out sleeping spiral shell be centrifuged, then under 6000r/min speed, carry out disk centrifugal, filter, obtain 2950mL trifoliate orange
Real flocculation liquid；
(4) nanofiltration, concentrate, be dried: by 2950mL step (3) gained Fructus Aurantii Immaturus flocculation liquid molecular cut off 5000Da nanofiltration
Film, is 1.2MPa at operation pressure, at temperature of charge 12 DEG C, nanofiltration to filter liquor electrical conductivity is 500 μ s/cm, then will
Trapped fluid is at vacuum pressure-0.085MPa, under temperature 50 C, is concentrated in vacuo to 200g, is finally vacuum dried, obtains 133.0g the most orange
Skin glycosides crude product；
(5) alcohol phase crystallizing and drying: by step (4) gained 133.0g neohesperidin crude product, with the ethanol of 250mL volume fraction 75%,
At 55 DEG C, after fully dissolving, tightly filter, be subsequently placed in crystallisation by cooling at 2 DEG C, obtain 250mL crystal, then with 250mL,
The frozen water of 2 DEG C washs, and repeats crystallisation by cooling, washing 2 times, vacuum drying, obtains 47.6g neohesperidin product.
Gained neohesperidin product shows white powder, detects through high performance liquid chromatography, and the purity of neohesperidin is
98.3%, ultimate yield is 91.12%.
Embodiment 2
(1) enzyme-added immersion: after 500g Fructus Aurantii Immaturus dry powder is broken to 10～30 mesh, is soaked in 1500mL water, is subsequently adding 0.30g
Composite plant hydrolytic enzyme preparation, at 45 DEG C, enzymolysis 150min, obtain enzymolysis Fructus Aurantii Immaturus；
(2) heating extraction: step (1) gained enzymolysis Fructus Aurantii Immaturus is added 3.5kg water, at 90 DEG C, continuous flow upstream extraction 90min,
It is cooled to 50 DEG C, under 1200r/min speed, carries out tripodia sedimentation and centrifugation, filter, obtain the enzyme-added lixiviating solution of 3480mL Fructus Aurantii Immaturus；
(3) flocculation purification: the enzyme-added lixiviating solution of 3480mL step (2) gained Fructus Aurantii Immaturus carries out water bath heat preservation, adds 8.0g wadding chlorination
Ferrum, stirring, at 50 DEG C, after flocculation treatment 70min, add 8.0g quick lime, stirring, at 50 DEG C, flocculation treatment 70min
After, under 3000r/min speed, carry out sleeping spiral shell be centrifuged, then under 6000r/min speed, carry out disk centrifugal, filter,
3450mL Fructus Aurantii Immaturus flocculation liquid；
(4) nanofiltration, concentrate, be dried: by 3450mL step (3) gained Fructus Aurantii Immaturus flocculation liquid molecular cut off 8000Da nanofiltration
Film, is 1.4MPa at operation pressure, at temperature of charge 16 DEG C, nanofiltration to filter liquor electrical conductivity is 500 μ s/cm；Then will
Trapped fluid is at vacuum pressure-0.08MPa, under temperature 60 C, is concentrated in vacuo to 210g, is finally vacuum dried, obtains 134.8g the most orange
Skin glycosides crude product；
(5) alcohol phase crystallizing and drying: by step (4) gained 134.8g neohesperidin crude product, with the ethanol of 280mL volume fraction 75%,
At 60 DEG C, after fully dissolving, tightly filter, be subsequently placed in crystallisation by cooling at 5 DEG C, obtain 280mL crystal, then with 300mL,
The frozen water of 5 DEG C washs, and repeats crystallisation by cooling, washing 2 times, vacuum drying, obtains 48.1g neohesperidin product.
Gained neohesperidin product is beige white powder shape, detects through high performance liquid chromatography, and the purity of neohesperidin is
98.2%, ultimate yield is 91.98%.
Embodiment 3
(1) enzyme-added immersion: after 500g Fructus Aurantii Immaturus dry powder is broken to 10～30 mesh, is soaked in 1700mL water, is subsequently adding 0.50g
Composite plant hydrolytic enzyme preparation, at 50 DEG C, enzymolysis 180min, obtain enzymolysis Fructus Aurantii Immaturus；
(2) heating extraction: step (1) gained enzymolysis Fructus Aurantii Immaturus is added 4.0kg water, at 95 DEG C, continuous flow upstream extraction 120min,
It is cooled to 55 DEG C, under 1200r/min speed, carries out tripodia sedimentation and centrifugation, filter, obtain the enzyme-added lixiviating solution of 4180mL Fructus Aurantii Immaturus；
(3) flocculation purification: the enzyme-added lixiviating solution of 4180mL step (2) gained Fructus Aurantii Immaturus carries out water bath heat preservation, adds 12.0g chlorination
Ferrum, stirring, at 55 DEG C, after flocculation treatment 80min, add 8.0g quick lime, stirring, at 55 DEG C, flocculation treatment 80min
After, under 3000r/min speed, carry out sleeping spiral shell be centrifuged, then under 6000r/min speed, carry out disk centrifugal, filter,
4135mL Fructus Aurantii Immaturus flocculation liquid；
(4) nanofiltration, concentrate, be dried: by 4135mL step (3) gained Fructus Aurantii Immaturus flocculation liquid molecular cut off 8000Da nanofiltration
Film, is 1.5MPa at operation pressure, at temperature of charge 20 DEG C, nanofiltration to filter liquor electrical conductivity is 500 μ s/cm；Then will
Trapped fluid is at vacuum pressure-0.07MPa, under temperature 70 C, is concentrated in vacuo to 206g, is finally vacuum dried, obtains 135.4g the most orange
Skin glycosides crude product；
(5) alcohol phase crystallizing and drying: by step (4) gained 135.4g neohesperidin crude product, with the ethanol of 300mL volume fraction 75%,
At 65 DEG C, after fully dissolving, tightly filter, be subsequently placed in crystallisation by cooling at 2 DEG C, obtain 300mL crystal, then with 350mL,
The frozen water of 2 DEG C washs, and repeats crystallisation by cooling, washing 2 times, vacuum drying, obtains 48.0g neohesperidin product.
Gained neohesperidin product shows white powder, detects through high performance liquid chromatography, and the purity of neohesperidin is
98.6%, ultimate yield is 92.17%.
Claims (10)
1. the method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus, it is characterised in that comprise the following steps:
(1) enzyme-added immersion: after immature bitter orange raw material is pulverized, be soaked in water, be subsequently adding composite plant hydrolytic enzyme preparation and carry out enzyme
Solve, obtain enzymolysis Fructus Aurantii Immaturus；
(2) heating extraction: by the heating extraction of step (1) gained enzymolysis Fructus Aurantii Immaturus, cool down, centrifugal, filter, obtain the enzyme-added extraction of Fructus Aurantii Immaturus
Liquid；
(3) flocculation purification: the enzyme-added lixiviating solution of step (2) gained Fructus Aurantii Immaturus carries out water bath heat preservation, adds flocculant, stirring, carries out
After flocculation treatment, centrifugal, filter, obtain Fructus Aurantii Immaturus flocculation liquid；
(4) nanofiltration, concentrate, be dried: by step (3) gained Fructus Aurantii Immaturus flocculation liquid carry out nanofiltration, concentrate, vacuum drying, obtain new Pericarpium Citri junoris
Glycosides crude product；
(5) alcohol phase crystallizing and drying: by step (4) gained neohesperidin crude product, fully dissolve with ethanol solution and tightly filter, so
After repeat crystallisation by cooling and washing, vacuum drying, obtain high purity novel aurantiamarin product.
The method extracting high purity novel aurantiamarin the most according to claim 1 from Fructus Aurantii Immaturus, it is characterised in that: in step (1),
Particle diameter after described immature bitter orange raw material is pulverized is 10～30 mesh；Described immature bitter orange raw material is 1:2.5～3.5 with the feed liquid mass ratio of water.
The method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus the most according to claim 1 or claim 2, it is characterised in that: step (1)
In, described composite plant hydrolytic enzyme preparation is the compound enzyme of cellulase, pectase and protease, wherein, cellulase: really
Glue enzyme: the mass ratio of protease is 2～3:1～2:0.5～1.0.
4. according to the method extracting high purity novel aurantiamarin one of claims 1 to 3 Suo Shu from Fructus Aurantii Immaturus, it is characterised in that: step
Suddenly in (1), quality is water volume the 0.01～0.03w/v% of described composite plant hydrolytic enzyme preparation interpolation；The temperature of described enzymolysis
Degree is 40～50 DEG C, and the time of enzymolysis is 120～180min.
5. according to the method extracting high purity novel aurantiamarin one of Claims 1 to 4 Suo Shu from Fructus Aurantii Immaturus, it is characterised in that: step
Suddenly in (2), described extraction is Continuous Countercurrent Extraction, and the temperature of extraction is 80～95 DEG C, and the time of extraction is 60～120min；Leaching
Carry add water quality is immature bitter orange raw material quality 6～8 times.
6. according to the method extracting high purity novel aurantiamarin one of Claims 1 to 5 Suo Shu from Fructus Aurantii Immaturus, it is characterised in that: step
Suddenly in (3), described flocculant is iron chloride and quick lime, after first using iron chloride flocculation treatment, then uses quick lime flocculation treatment, two
The temperature of secondary flocculation treatment is 40～60 DEG C, and the time of flocculation treatment is 60～80min.
The method extracting high purity novel aurantiamarin the most according to claim 6 from Fructus Aurantii Immaturus, it is characterised in that: in step (3),
The consumption of described every kind of flocculant is 1.5～3.0g/L.
8. according to the method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus one of claim 1～7 Suo Shu, it is characterised in that: step
Suddenly in (4), the molecular cut off of NF membrane used by described nanofiltration is 5000～8000Da, and operation pressure is 1.0～1.5MPa, thing
Material temperature degree is 10～25 DEG C, and nanofiltration is to the μ s/cm of filter liquor electrical conductivity≤500；Described concentration for being concentrated in vacuo, vacuum pressure
For-0.09～-0.07MPa, temperature is 50～80 DEG C, till be concentrated into that concentrated solution quality is raw materials quality 40～50%.
9. according to the method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus one of claim 1～8 Suo Shu, it is characterised in that: step
Suddenly, in (5), the volume fraction of described ethanol solution is 70～90%；The consumption of described ethanol solution is to dissolve in every 100mL ethanol
Neohesperidin crude product 40～60g；The temperature of described dissolving is 50～70 DEG C.
10. according to the method extracting high purity novel aurantiamarin from Fructus Aurantii Immaturus one of claim 1～9 Suo Shu, it is characterised in that: step
Suddenly, in (5), the temperature of described crystallisation by cooling is 2～5 DEG C, number of repetition >=2 time；Wash with the frozen water of 2～5 DEG C, every time
Washings consumption is 1～2 times of crystal volume.
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| CN111675742B (en) * | 2020-07-20 | 2021-07-27 | 江西海富生物工程有限公司 | Preparation method of neohesperidin with heavy metal removed |
| CN111777653A (en) * | 2020-08-21 | 2020-10-16 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
| CN111777653B (en) * | 2020-08-21 | 2023-07-21 | 江西海富生物工程有限公司 | Preparation method of pure natural high-content neohesperidin |
| CN112079884A (en) * | 2020-09-03 | 2020-12-15 | 江西海富生物工程有限公司 | Preparation method of natural neohesperidin |
| CN113651791A (en) * | 2021-09-01 | 2021-11-16 | 湖南华诚生物资源股份有限公司 | Method for separating hesperetin from immature bitter orange |
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