CN111153759A - Method for extracting total phenolic acid from waste liquid of ester extraction in Mailuoning injection production - Google Patents
Method for extracting total phenolic acid from waste liquid of ester extraction in Mailuoning injection production Download PDFInfo
- Publication number
- CN111153759A CN111153759A CN202010053959.7A CN202010053959A CN111153759A CN 111153759 A CN111153759 A CN 111153759A CN 202010053959 A CN202010053959 A CN 202010053959A CN 111153759 A CN111153759 A CN 111153759A
- Authority
- CN
- China
- Prior art keywords
- waste liquid
- reduced pressure
- phenolic acid
- filtrate
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000002699 waste material Substances 0.000 title claims abstract description 37
- 239000007788 liquid Substances 0.000 title claims abstract description 33
- 150000002148 esters Chemical class 0.000 title claims abstract description 30
- 238000002347 injection Methods 0.000 title claims abstract description 27
- 239000007924 injection Substances 0.000 title claims abstract description 27
- 238000000605 extraction Methods 0.000 title claims abstract description 25
- 239000009064 mailuoning Substances 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 150000007965 phenolic acids Chemical class 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000000706 filtrate Substances 0.000 claims abstract description 17
- 239000000284 extract Substances 0.000 claims abstract description 15
- 239000004952 Polyamide Substances 0.000 claims abstract description 13
- 229920002647 polyamide Polymers 0.000 claims abstract description 13
- 239000007787 solid Substances 0.000 claims abstract description 12
- 238000005406 washing Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 239000003480 eluent Substances 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 6
- 238000010828 elution Methods 0.000 claims abstract description 5
- 239000012535 impurity Substances 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 description 11
- 239000000463 material Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 230000008901 benefit Effects 0.000 description 4
- 238000011068 loading method Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229920006122 polyamide resin Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- FVQOMEDMFUMIMO-UHFFFAOYSA-N Hyperosid Natural products OC1C(O)C(O)C(CO)OC1OC1C(=O)C2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 FVQOMEDMFUMIMO-UHFFFAOYSA-N 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- 208000026106 cerebrovascular disease Diseases 0.000 description 2
- 235000001368 chlorogenic acid Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000287 crude extract Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 1
- 241000427159 Achyranthes Species 0.000 description 1
- MQVRGDZCYDEQML-UHFFFAOYSA-N Astragalin Natural products C1=CC(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 MQVRGDZCYDEQML-UHFFFAOYSA-N 0.000 description 1
- JMGZEFIQIZZSBH-UHFFFAOYSA-N Bioquercetin Natural products CC1OC(OCC(O)C2OC(OC3=C(Oc4cc(O)cc(O)c4C3=O)c5ccc(O)c(O)c5)C(O)C2O)C(O)C(O)C1O JMGZEFIQIZZSBH-UHFFFAOYSA-N 0.000 description 1
- 208000033386 Buerger disease Diseases 0.000 description 1
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 241001523681 Dendrobium Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 description 1
- OVSQVDMCBVZWGM-SJWGPRHPSA-N Hyperin Natural products O[C@H]1[C@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-SJWGPRHPSA-N 0.000 description 1
- 241000100289 Lonicera confusa Species 0.000 description 1
- 241001570521 Lonicera periclymenum Species 0.000 description 1
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 1
- 108010064851 Plant Proteins Proteins 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- 235000002226 Ranunculus ficaria Nutrition 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 241000293861 Scrophularia nodosa Species 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 206010043540 Thromboangiitis obliterans Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 1
- 229940074393 chlorogenic acid Drugs 0.000 description 1
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 1
- -1 chlorogenic acids Chemical class 0.000 description 1
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RAFHNDRXYHOLSH-SFTVRKLSSA-N eriodictyol 7-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C(C(=O)C[C@H](O2)C=3C=C(O)C(O)=CC=3)C2=C1 RAFHNDRXYHOLSH-SFTVRKLSSA-N 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- GXMWXESSGGEWEM-UHFFFAOYSA-N isoquercitrin Natural products OCC(O)C1OC(OC2C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)C(O)C1O GXMWXESSGGEWEM-UHFFFAOYSA-N 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- JPUKWEQWGBDDQB-QSOFNFLRSA-N kaempferol 3-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O JPUKWEQWGBDDQB-QSOFNFLRSA-N 0.000 description 1
- ZDQHCVFHPTWFMA-UHFFFAOYSA-N kaempferol 3-O-beta-D-glucoside Natural products OCC1OC(OC2=C(Oc3cc(O)cc(O)c3C2)c4ccc(O)c(O)c4)C(O)C(O)C1O ZDQHCVFHPTWFMA-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000009629 microbiological culture Methods 0.000 description 1
- 239000010812 mixed waste Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 235000021118 plant-derived protein Nutrition 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- OVSQVDMCBVZWGM-DTGCRPNFSA-N quercetin 3-O-beta-D-galactopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-DTGCRPNFSA-N 0.000 description 1
- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- BBFYUPYFXSSMNV-UHFFFAOYSA-N quercetin-7-o-galactoside Natural products OC1C(O)C(O)C(CO)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 BBFYUPYFXSSMNV-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 235000005493 rutin Nutrition 0.000 description 1
- IKGXIBQEEMLURG-BKUODXTLSA-N rutin Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@@H]1OC[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-BKUODXTLSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229940126680 traditional chinese medicines Drugs 0.000 description 1
- JGXFMIJHKASCIZ-LDBVRRDLSA-N tricin 7-O-beta-D-glucoside Chemical compound COC1=C(O)C(OC)=CC(C=2OC3=CC(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=CC(O)=C3C(=O)C=2)=C1 JGXFMIJHKASCIZ-LDBVRRDLSA-N 0.000 description 1
- DJMNLMGCMIBKIY-UHFFFAOYSA-N tricin 7-O-beta-D-glucoside Natural products COc1cc(cc(OC)c1O)C2=CC(=O)c3c(O)c(O)c(OC4OC(CO)C(O)C(O)C4O)cc3O2 DJMNLMGCMIBKIY-UHFFFAOYSA-N 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention discloses a method for extracting total phenolic acid from waste liquid generated in ester extraction in Mailuoning injection production, which is characterized by comprising the following process steps of: (1) concentrating the waste liquid of ester extraction in the production of Mailuoning injection to obtain a liquid extract without ester smell, adding 8-12 times of water for dissolving, filtering, and removing insoluble substances to obtain a filtrate; (2) concentrating the filtrate under reduced pressure to 1/3-1/5 of the volume of the original filtrate; (3) adsorbing the concentrated filtrate by polyamide, washing off water-soluble impurities by using water, performing gradient elution by using 10%, 30%, 50%, 70% and 95% ethanol in sequence, and collecting 50% and 70% eluates; (4) and concentrating the eluent with the concentration of 50 percent and 70 percent under reduced pressure until dry solid without organic solvent smell is obtained, wherein the dry solid is the total phenolic acid extract.
Description
Technical Field
The invention relates to the field of natural medicinal chemistry, in particular to a method for extracting total phenolic acid from waste liquid generated in ester extraction in Mailuoning injection production.
Background
The Mailuoning injection is an exclusive product in Jinling pharmaceutical industry of our province, is developed on the basis of the famous medical prescription 'Simiaoyong' an decoction, and is a traditional Chinese medicine compound injection prepared by extracting and refining traditional Chinese medicines of dendrobium, figwort, achyranthes root, honeysuckle and lonicera confusa. It is mainly used for treating cardiovascular and cerebrovascular diseases such as ischemic apoplexy acute stage, thromboangiitis obliterans, cerebral infarction, etc. In 1992, the traditional Chinese medicine is listed as one of the first national traditional Chinese medicine indispensable for emergency treatment and the national traditional Chinese medicine protection variety; in 2000, 6 months, the Chinese patent medicine is listed as Chinese patent medicine A class medicine in the catalog of national basic medical insurance medicines; in 2009, 307 new medical improvement basic drug catalog basic edition were selected in 7 months, which is one of only 3 varieties of Chinese medicinal injection, and the Mailuoning injection is also the single variety of Jiangsu province drugs with the largest sales volume.
The process for producing the Mailuoning injection mainly comprises two stages, namely an extraction stage, namely crude extract is obtained by mixing the five medicinal materials, extracting with boiling water, precipitating with ethanol and extracting with ethyl acetate, and a preparation stage, namely the crude extract is prepared by water precipitation, filtration, liquid preparation, fine filtration filling and sterilization, wherein the main components of the finished product are medium-polarity small molecular compounds such as chlorogenic acids, flavonoids, coumarins, iridoids and the like, and the wastes are mainly generated in the first stage and comprise ① mixed waste residues of the five medicinal materials after water extraction, ② alcohol precipitation section waste residues (alcohol precipitation waste residues) mainly containing plant polysaccharides, plant proteins and the like, ③ ethyl acetate extraction mother liquor waste residues (ester extraction waste residues) mainly containing large-polarity triterpenes, saponins, water-soluble pigments and the like.
To deal with these wastes, Jinling drugs have taken various measures for harmlessness and recycling. The medicinal material waste residue is transferred to a fertilizer and feed company and processed into various biological organic fertilizers, feed additives, microbial culture media and the like, but the added value is low, so that no economic benefit is brought to enterprises by transferring the medicinal material waste residue. The alcohol precipitation waste liquid and the ester extraction waste liquid have complex components and high organic solvent content, and are subjected to harmless treatment mainly through microbial degradation after the solvent is recovered. Considering that the ester extraction waste liquid contains a plurality of active ingredients of raw medicinal materials, the development of a simple, convenient, accurate and environment-friendly preparation method for extracting the total phenolic acid from the ester extraction waste liquid in the production of the Mailuoning injection has important significance.
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a method for extracting total phenolic acid from the waste liquid of ester extraction in the production of Mailuoning injection, which can be industrially produced, has simple preparation method and small organic solvent consumption.
In order to achieve the above object, the present invention adopts the following technical solutions:
a method for extracting total phenolic acid from waste liquid generated in ester extraction in Mailuoning injection production is characterized by comprising the following process steps: (1) concentrating the waste liquid of ester extraction in the production of Mailuoning injection to obtain a liquid extract without ester smell, adding 8-12 times of water for dissolving, filtering, and removing insoluble substances to obtain a filtrate; (2) concentrating the filtrate under reduced pressure to 1/3-1/5 of the volume of the original filtrate; (3) adsorbing the concentrated filtrate by polyamide, washing off water-soluble impurities by using water, performing gradient elution by using 10%, 30%, 50%, 70% and 95% ethanol in sequence, and collecting 50% and 70% eluates; (4) and concentrating the eluent with the concentration of 50 percent and 70 percent under reduced pressure until dry solid without organic solvent smell is obtained, wherein the dry solid is the total phenolic acid extract.
Preferably, in the step (2), the filtrate is subjected to reduced pressure concentration in a water bath, wherein the temperature of the water bath is 55-65 ℃, and the reduced pressure is 7-10 kPa.
Still preferably, in the step (4), the 50% and 70% of the eluate is concentrated under reduced pressure in a water bath, wherein the temperature of the water bath is 55-65 ℃, and the reduced pressure is 7-10 kPa.
More preferably, the aforementioned polyamide is PA6 or PA66 or PA 1212.
The invention has the advantages that the preparation method is simple, the organic solvent consumption is small, the method can be used for the industrial production of the phenolic acid components, a large amount of waste generated in the production process of the Mailuoning injection is effectively recycled, the waste is recycled, the resource waste is effectively reduced, and the production cost is reduced.
Detailed Description
The following specific examples are intended to illustrate the invention.
The invention obtains total phenolic acid from the Mailuoning injection production ester extraction waste liquid through polyamide column chromatography, the total yield is more than 7 percent, polyamide columns with various types and polarities are researched by preparation technology, the material which is most suitable for extracting the total phenolic acid from the Mailuoning injection production ester extraction waste liquid and the parameters of optimal sample loading amount, sample loading concentration, elution solvent, elution volume, flow rate and the like are preferably selected, the optimal extraction technology of the total phenolic acid from the Mailuoning injection production ester extraction waste liquid is preferably selected, and the obtained total phenolic acid contains main active ingredients including main active ingredients of eriodictyol-7-O- β -D-glucoside, tricin-7-O- β -D-glucoside, isoquercitrin, kaempferol-3-O- β -D-glucoside, quercetin, hyperin, rutin and chlorogenic acid.
If no special indication is provided, the test method is a conventional test method; the reagent materials used are commercially available.
Example 1:
concentrating the waste liquid of Mailuoning injection ester extraction to obtain liquid extract without ester smell 10L, dissolving in 80L water, filtering, removing water insoluble substances, concentrating the filtrate under reduced pressure (instrument: B ÜCHI rotary evaporator R-210, wherein water bath is 55 deg.C, Vacuum Pump V-700 decompression Pump, reducing pressure to 70mbar (7 kPa)), concentrating under reduced pressure to about 1/3 volume 30L, adsorbing with 45L polyamide (PA 6), loading sample volume to polyamide volume ratio is 2: 3, flow rate is 8 mL/min, adsorbing effective components in the liquid onto polyamide resin, discarding effluent, washing resin column with 1 column volume of distilled water, washing water soluble impurities with water, discarding, washing resin column with 2 column volume of 20% ethanol, discarding effluent, sequentially eluting with 10%, 30%, 50%, 70%, 95% ethanol, collecting 50%, 70% eluent, and concentrating under reduced pressure to obtain solid extract without ester smell (instrument: B ÜCHI rotary evaporator R-210, wherein water bath is 55 Mpa), concentrating under reduced pressure to obtain solid extract without organic solvent odor, and reducing pressure to 700 kPa).
Example 2:
concentrating the waste liquid of Mailuoning injection ester extraction to obtain liquid extract without ester smell 10L, dissolving in 100L water, filtering, removing water insoluble substances, concentrating the filtrate under reduced pressure (instrument: B ÜCHI rotary evaporator R-210, wherein water bath is 60 deg.C, Vacuum Pump V-700 decompression Pump, decompression is 85mbar (8.5 kPa)), concentrating under reduced pressure to obtain 28L of 1/4 volume, adsorbing with 56L polyamide (PA 66), loading the sample volume and polyamide volume ratio is 1: 2, flow rate is 10 mL/min, adsorbing the effective components in the liquid onto polyamide resin, washing with water to remove water-soluble impurities, discarding the effluent, washing the resin column with distilled water of 1 column volume, discarding the effluent, washing the resin column with 20% ethanol of 2 column volumes, discarding the effluent, sequentially eluting with 30%, 50%, 70%, 95% ethanol, collecting 50%, 70% eluent, and finally concentrating under reduced pressure to obtain solid extract with reduced pressure of 50%, 70% concentration (instrument: B ÜCHI R-210, wherein the Vacuum Pump is 60 mbar), and the organic solvent is dried solid extract with reduced pressure to obtain dried solid extract (700 mbar).
Example 3:
concentrating the waste liquid of Mailuoning injection ester extraction to obtain liquid extract without ester smell 10L, dissolving in 120L water, filtering, removing water insoluble substances, concentrating the filtrate under reduced pressure (instrument: B ÜCHI rotary evaporator R-210, wherein water bath is 65 deg.C, Vacuum Pump V-700 reduced pressure Pump, reduced pressure to 100 mbar (10 kPa)), concentrating under reduced pressure to about 1/5 volume 26L, adsorbing the concentrated solution by 52L polyamide column (PA 1212), the volume ratio of the sample volume to the polyamide is 1: 2, the flow rate is 10 mL/min, adsorbing the effective components in the liquid onto the polyamide resin, discarding the effluent, washing the resin column with 1 column volume of distilled water, discarding the effluent, washing the resin column with 2 column volumes of 20% ethanol, discarding the effluent, performing gradient elution with 30%, 50%, 70%, 90% ethanol, collecting 50%, 70% ethanol eluate, and finally concentrating 50%, 70% eluate (instrument: B ÜCHI rotary evaporator R-210, wherein the Vacuum Pump V-700 m water bath is reduced pressure Pump, reduced pressure to obtain the solid extract without dry odor of organic solvent (dry odor, namely, reduced pressure).
The invention has the advantages that the preparation method is simple, the organic solvent consumption is small, the method can be used for the industrial production of the phenolic acid components, a large amount of waste generated in the production process of the Mailuoning injection is effectively recycled, the waste is recycled, the resource waste is effectively reduced, and the production cost is reduced.
The foregoing illustrates and describes the principles, general features, and advantages of the present invention. It should be understood by those skilled in the art that the above embodiments do not limit the present invention in any way, and all technical solutions obtained by using equivalent alternatives or equivalent variations fall within the scope of the present invention.
Claims (4)
1. A method for extracting total phenolic acid from waste liquid generated in ester extraction in Mailuoning injection production is characterized by comprising the following process steps: (1) concentrating the waste liquid of ester extraction in the production of Mailuoning injection to obtain a liquid extract without ester smell, adding 8-12 times of water for dissolving, filtering, and removing insoluble substances to obtain a filtrate; (2) concentrating the filtrate under reduced pressure to 1/3-1/5 of the volume of the original filtrate; (3) adsorbing the concentrated filtrate by polyamide, washing off water-soluble impurities by using water, performing gradient elution by using 10%, 30%, 50%, 70% and 95% ethanol in sequence, and collecting 50% and 70% eluates; (4) and concentrating the eluent with the concentration of 50 percent and 70 percent under reduced pressure until dry solid without organic solvent smell is obtained, wherein the dry solid is the total phenolic acid extract.
2. The method for extracting total phenolic acid from the waste liquid from the ester extraction in the production of Mailuoning injection as claimed in claim 1, wherein in the step (2), the filtrate is concentrated under reduced pressure in a water bath, wherein the temperature of the water bath is 55-65 ℃, and the reduced pressure is 7-10 kPa.
3. The method for extracting total phenolic acid from the waste liquid from the ester extraction in the production of Mailuoning injection as claimed in claim 1, wherein in the step (4), 50% and 70% of the eluent is concentrated under reduced pressure in a water bath, wherein the temperature of the water bath is 55-65 ℃, and the pressure is reduced to 7kPa-10 kPa.
4. The method for extracting total phenolic acid from the waste liquid from the ester extraction of Mailuoning injection as claimed in claim 1, wherein the polyamide is PA6 or PA66 or PA 1212.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010053959.7A CN111153759A (en) | 2020-01-17 | 2020-01-17 | Method for extracting total phenolic acid from waste liquid of ester extraction in Mailuoning injection production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010053959.7A CN111153759A (en) | 2020-01-17 | 2020-01-17 | Method for extracting total phenolic acid from waste liquid of ester extraction in Mailuoning injection production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111153759A true CN111153759A (en) | 2020-05-15 |
Family
ID=70563792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010053959.7A Pending CN111153759A (en) | 2020-01-17 | 2020-01-17 | Method for extracting total phenolic acid from waste liquid of ester extraction in Mailuoning injection production |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111153759A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1439410A (en) * | 2003-02-13 | 2003-09-03 | 黑龙江省润通生物药业有限责任公司 | Extraction method for antibiosis antiviral active placement from honeysuckle |
| CN1491688A (en) * | 2003-07-25 | 2004-04-28 | 金陵药业股份有限公司 | Immune regulator prepared from waste material in preparing Mailuoning injection process and its use in producing medicine |
| CN1687008A (en) * | 2005-03-22 | 2005-10-26 | 中国药科大学 | Method for extracting compound of phenolic acid from leaves of woodbind |
| CN102911055A (en) * | 2012-11-13 | 2013-02-06 | 西南大学 | Method for extracting chlorogenic acid |
| WO2016082126A1 (en) * | 2014-11-26 | 2016-06-02 | 四川九章生物科技有限公司 | Device for enriching and purifying compounds and use method therefor |
| CN108272890A (en) * | 2018-03-14 | 2018-07-13 | 江苏省中国科学院植物研究所 | The preparation method of liposoluble ingredient is extracted after a kind of processing byproduct poplar bark degreasing from timber again |
-
2020
- 2020-01-17 CN CN202010053959.7A patent/CN111153759A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1439410A (en) * | 2003-02-13 | 2003-09-03 | 黑龙江省润通生物药业有限责任公司 | Extraction method for antibiosis antiviral active placement from honeysuckle |
| CN1491688A (en) * | 2003-07-25 | 2004-04-28 | 金陵药业股份有限公司 | Immune regulator prepared from waste material in preparing Mailuoning injection process and its use in producing medicine |
| CN1687008A (en) * | 2005-03-22 | 2005-10-26 | 中国药科大学 | Method for extracting compound of phenolic acid from leaves of woodbind |
| CN102911055A (en) * | 2012-11-13 | 2013-02-06 | 西南大学 | Method for extracting chlorogenic acid |
| WO2016082126A1 (en) * | 2014-11-26 | 2016-06-02 | 四川九章生物科技有限公司 | Device for enriching and purifying compounds and use method therefor |
| CN108272890A (en) * | 2018-03-14 | 2018-07-13 | 江苏省中国科学院植物研究所 | The preparation method of liposoluble ingredient is extracted after a kind of processing byproduct poplar bark degreasing from timber again |
Non-Patent Citations (9)
| Title |
|---|
| 刘双双等: "超滤膜技术用于脉络宁注射液废弃物中多糖分离及其活性筛选研究", 《中草药》 * |
| 刘飞等: "栝楼雄株茎叶酚酸类化学成分研究", 《中国现代中药》 * |
| 李博等: "基于资源化利用思路的陶瓷膜处理中药脉络宁生产废水的研究", 《膜科学与技术》 * |
| 王建国等: "《实用中草药生产技术》", 31 October 1993, 河南科学技术出版社 * |
| 翟海燕等: "《食品质量检验 第2版》", 30 September 2018, 中国质检出版社 * |
| 肖草茂等: "翻白草中酚酸类化学成分的研究", 《华西药学杂志》 * |
| 郝凤霞等: "金银花中绿原酸和黄酮的同时提取分离工艺研究", 《食品科学》 * |
| 陈绍民等: "聚酰胺树脂分离纯化丹参总酚酸的研究", 《中国实验方剂学杂志》 * |
| 高学敏等: "《家庭中医》", 28 February 1998, 中国科学技术出版社 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111960926B (en) | Preparation method of cannabidiol crystal | |
| CN109593034A (en) | A method of it is extracted in waste liquid from ginkgo leaf and prepares shikimic acid | |
| CN111285916B (en) | Preparation method of centella asiatica extract with high content of total asiaticosides | |
| CN111978158A (en) | Method for extracting purified hypocannabidiol from industrial cannabis sativa | |
| CN105061525A (en) | Preparation method of mono-ammonium glycyrrhizinate | |
| CN112010738B (en) | Industrial method for producing cannabinoid compound by utilizing chromatographic separation | |
| CN113754518A (en) | Method for efficiently purifying cannabidiol from industrial cannabis sativa leaves | |
| CN102267906B (en) | Extraction method for chlorogenic acid | |
| CN111714953A (en) | Method for removing phthalate plasticizer in extract | |
| CN101366829B (en) | Method for synchronously extracting flavone and alkaloid from folium nelumbinis | |
| CN1876641B (en) | Method for purifying salvianolic acid B | |
| CN102050851A (en) | Liquiritin and preparation method thereof | |
| CN111153759A (en) | Method for extracting total phenolic acid from waste liquid of ester extraction in Mailuoning injection production | |
| CN111548380A (en) | Preparation method of monotropein in morinda officinalis | |
| CN104987952B (en) | Method for extracting volatile oil and salidroside from rhodiola rosea whole plant | |
| CN114276391A (en) | Separation and purification method of verbascoside | |
| CN109970838B (en) | Preparation method of pedunculoside | |
| CN113278089A (en) | Separation, extraction and purification method of dogwood seed polysaccharide | |
| CN111763189A (en) | Method for separating and purifying cannabinol from industrial cannabis sativa | |
| CN111035719A (en) | Method for extracting total saponins from Mailuoning injection production waste liquid | |
| CN111848356A (en) | Preparation method of cannabidiol | |
| CN107739306B (en) | A method for preparing refined herba Rosmarini officinalis extract | |
| CN101385750B (en) | Preparation method of effective ingredient of isatis root | |
| CN110938066A (en) | Puerarin extraction method | |
| CN106916859B (en) | Method for rapidly extracting liquiritigenin from liquorice waste residue |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200515 |