CN115028613A - Method for extracting lutein ester and quercitrin from marigold flower - Google Patents
Method for extracting lutein ester and quercitrin from marigold flower Download PDFInfo
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- CN115028613A CN115028613A CN202210741682.6A CN202210741682A CN115028613A CN 115028613 A CN115028613 A CN 115028613A CN 202210741682 A CN202210741682 A CN 202210741682A CN 115028613 A CN115028613 A CN 115028613A
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- quercetagetin
- lutein ester
- marigold
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- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 title claims abstract description 87
- 235000005881 Calendula officinalis Nutrition 0.000 title claims abstract description 73
- 238000000034 method Methods 0.000 title claims abstract description 56
- LUJAXSNNYBCFEE-UHFFFAOYSA-N Quercetin 3,7-dimethyl ether Natural products C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(O)C(O)=C1 LUJAXSNNYBCFEE-UHFFFAOYSA-N 0.000 title claims abstract description 4
- PUTDIROJWHRSJW-UHFFFAOYSA-N Quercitrin Natural products CC1OC(Oc2cc(cc(O)c2O)C3=CC(=O)c4c(O)cc(O)cc4O3)C(O)C(O)C1O PUTDIROJWHRSJW-UHFFFAOYSA-N 0.000 title claims abstract description 4
- OXGUCUVFOIWWQJ-XIMSSLRFSA-N acanthophorin B Natural products O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-XIMSSLRFSA-N 0.000 title claims abstract description 4
- OEKUVLQNKPXSOY-UHFFFAOYSA-N quercetin 3-O-beta-D-glucopyranosyl(1->3)-alpha-L-rhamnopyranosyl(1->6)-beta-d-galactopyranoside Natural products OC1C(O)C(C(O)C)OC1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OEKUVLQNKPXSOY-UHFFFAOYSA-N 0.000 title claims abstract description 4
- QPHXPNUXTNHJOF-UHFFFAOYSA-N quercetin-7-O-beta-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=CC=3)OC2=C1 QPHXPNUXTNHJOF-UHFFFAOYSA-N 0.000 title claims abstract description 4
- OXGUCUVFOIWWQJ-HQBVPOQASA-N quercitrin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OXGUCUVFOIWWQJ-HQBVPOQASA-N 0.000 title claims abstract description 4
- 240000000785 Tagetes erecta Species 0.000 title 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N quercetagetin Chemical compound 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 claims abstract description 128
- 241000736851 Tagetes Species 0.000 claims abstract description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 66
- 238000000605 extraction Methods 0.000 claims abstract description 44
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000000243 solution Substances 0.000 claims abstract description 28
- 239000012046 mixed solvent Substances 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000001273 butane Substances 0.000 claims abstract description 15
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims abstract description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011259 mixed solution Substances 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims abstract description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 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 claims description 32
- 235000005875 quercetin Nutrition 0.000 claims description 17
- 229960001285 quercetin Drugs 0.000 claims description 17
- 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 claims description 14
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 14
- 238000000926 separation method Methods 0.000 claims description 8
- 229940107604 lutein esters Drugs 0.000 claims 9
- 150000002658 luteins Chemical class 0.000 claims 9
- 239000004480 active ingredient Substances 0.000 abstract description 4
- 239000013543 active substance Substances 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 abstract description 2
- 239000000284 extract Substances 0.000 description 27
- 239000002245 particle Substances 0.000 description 22
- 235000012680 lutein Nutrition 0.000 description 20
- 229960005375 lutein Drugs 0.000 description 20
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 20
- 239000001656 lutein Substances 0.000 description 20
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 20
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 20
- 238000001816 cooling Methods 0.000 description 18
- 238000002156 mixing Methods 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 9
- 238000007599 discharging Methods 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 7
- 229930003944 flavone Natural products 0.000 description 7
- 150000002212 flavone derivatives Chemical class 0.000 description 7
- 235000011949 flavones Nutrition 0.000 description 7
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 7
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- 229930186743 Quercetol Natural products 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 241000208838 Asteraceae Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 1
- -1 flavonol compounds Chemical class 0.000 description 1
- 235000011957 flavonols Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A method for extracting lutein ester and quercetagetin from marigold flowers belongs to the technical field of extraction of plant active ingredients. The method is characterized by comprising the following steps: 1) subcritical extracting marigold flower by using a mixed solvent of dimethyl ether and butane, wherein the mass ratio of the marigold flower to the mixed solution is 1: 3-12, and the mass ratio of the dimethyl ether to the butane in the mixed solvent is 1: 2-8, so as to obtain an extracting solution; 2) concentrating the extracting solution into a mixture containing lutein ester and quercetagetin, wherein the solid content in the mixture is 92-96%; 3) extracting and separating the mixture obtained in the step 2) by using a methanol solvent to obtain two products of quercitrin and lutein ester. The invention solves the problem that the harmful residue of the existing products, namely lutein ester and quercetagetin, is high, and solves the problem that the lutein ester active substances are easy to damage.
Description
Technical Field
A method for extracting lutein ester and quercetagetin from marigold flowers belongs to the technical field of extraction of plant active ingredients.
Background
Quercetin (QG) belongs to flavonol compounds, is one of main components of marigold of Compositae, and has certain antioxidant effect. Quercetin is a natural antioxidant extracted from marigold, and has the advantages of safety, high efficiency and the like.
At present, the extraction method of lutein and flavone mainly adopts a step-by-step extraction method. Chinese patent 201811188771.2 discloses an industrial preparation method of lutein and marigold flavone, which adopts a mixed solvent of petroleum ether and acetone for extraction, and the separation mode adopted in the patent is that water is added for separation, the operation is complex, and high-purity quercetagetin cannot be obtained by separation, and only a marigold flavone mixture can be obtained.
Chinese patent CN110746331A discloses an industrial method for extracting lutein and quercetol from marigold flower particles, which comprises the following steps: 1) extracting marigold flower particles by using an acetone solution with the volume fraction of 90-99% to obtain an extracting solution; 2) concentrating the extracting solution until the solid content is 60-95%, and extracting the concentrated solution by using a low-polarity solvent to obtain a quercetagetin product and a lutein product. The method can simultaneously extract lutein and quercetagetin. But the method uses 90 to 99 percent acetone solution to extract lutein and quercetol, the extraction solvent acetone has high boiling point and high solvent toxicity, the loss of the active ingredient lutein ester in the product extraction and purification process is large, and the acetone residue in the product is high.
Chinese patent 201811188771.2 discloses an industrial preparation method of lutein and marigold flavone, which is mainly improved by mixing a lutein extraction solvent of petroleum ether and a flavone extraction solvent, extracting marigold flower particles, and adding a strong polar solvent into the flavone extraction solvent after extraction is finished, so as to further promote the separation of lutein and marigold flavone. The invention can improve the extraction efficiency, and the invention adopts the mixed solvent of petroleum ether and acetone, and also has the phenomenon that the solvent residue in the product is difficult to remove.
There is still no safe method for extracting lutein and quercetagetin.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: overcomes the defects of the prior art and provides a method for extracting lutein ester and quercetagetin from marigold flowers without harmful residues.
The technical scheme adopted by the invention for solving the technical problems is as follows: the method for extracting lutein ester and quercetagetin from marigold flowers is characterized by comprising the following steps:
1) subcritical extracting marigold flower by using a mixed solvent of dimethyl ether and butane, wherein the mass ratio of the marigold flower to the mixed solution is 1: 3-12, and the mass ratio of the dimethyl ether to the butane in the mixed solvent is 1: 2-8, so as to obtain an extracting solution;
2) concentrating the extracting solution into a mixture containing lutein ester and quercetagetin, wherein the solid content in the mixture is 92-96%;
3) extracting and separating the mixture obtained in the step 2) by using a methanol solvent to obtain two products of quercitrin and lutein ester.
The invention mainly provides a novel mixed solvent capable of simultaneously extracting lutein ester and quercetagetin from marigold flowers, and the mixed solvent can be used for avoiding harmful residues under the conditions of high-efficiency and high-yield extraction and simultaneously avoiding active substances from being damaged in the extraction process. The mixed solvent can be easily and thoroughly separated from the extract after subcritical extraction. The extract is extracted and separated by a methanol solvent, and two products of quercetagetin and lutein ester with higher purity are obtained at the same time.
Preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the following steps of 1) mixing marigold flowers with a mixed solution in a mass ratio of 1:5 to 8. The preferred ratio of marigold flower to mixed solution can reduce the amount of solvent as much as possible while ensuring the yield of both products.
More preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the following steps that in the step 1), the mass ratio of the marigold flowers to the mixed solution is 1: 5.3 to 6.1. The best ratio of the marigold flowers to the mixed solution can reach the maximum yield of the invention under the condition of the mixed solvent.
Preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the following steps of 1) mixing dimethyl ether and butane in the mixed solvent in the step 1) in a mass ratio of 1:4 to 6. The dimethyl ether and the butane are mixed in a subcritical state to obtain a mixed solvent, the preferable proportion can better adapt to the extraction requirement of the invention, and the lutein ester and the quercetagetin can be extracted at the same time with high yield.
More preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the step 1) that the mass ratio of dimethyl ether to butane in the mixed solvent is 1:4.7 to 5.2. The most preferred mixed solvent formulation achieves the maximum extraction yield of the present invention.
The preferable method for extracting lutein ester and quercetagetin from marigold flowers comprises the step 1), wherein the subcritical extraction temperature is 25-50 ℃, the extraction times are 3-6 times, and the extraction time of each time is 15-60 min. The optimized subcritical extraction process can completely extract lutein ester and quercetagetin in marigold flowers, and ensures the high yield of the method.
Preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the step 3) that the volume fraction of methanol in the methanol solvent is 75-85%. The preferred methanol solvent can better extract and separate the extract, and ensures the high purity of the extracted product.
Preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the following steps of 3), wherein the mass ratio of the mixture to a methanol solvent in step 3) is 1:5 to 10. The preferred mass ratio of mixture to methanol solvent allows for a more complete separation of the two products.
Preferably, the method for extracting lutein ester and quercetol from marigold flowers is used, and the extraction and separation in the step 3) are carried out at the temperature of 65-90 ℃. The two products are easier to separate under the extraction solvent of the invention at the preferable extraction temperature, and the thorough separation is ensured.
Preferably, the method for extracting lutein ester and quercetagetin from marigold flowers comprises the step 2) that the solid content in the mixture is 94-95%. The preferable solid content can ensure the smooth extraction and the purity of the lower-layer lutein ester product after extraction.
Compared with the prior art, the method for extracting lutein ester and quercetagetin from marigold flowers has the following beneficial effects: the invention simultaneously extracts two functional active ingredients, namely lutein ester and quercetagetin, from marigold flowers by a subcritical method. The invention mainly provides a novel mixed solvent capable of simultaneously extracting lutein ester and quercetagetin from marigold flowers, and the mixed solvent can be used for avoiding harmful residues under the conditions of high-efficiency and high-yield extraction and simultaneously avoiding active substances from being damaged in the extraction process. The mixed solvent can be easily and thoroughly separated from the extract after subcritical extraction. The extract is extracted and separated by a methanol solvent, and two products of quercetagetin and lutein ester with higher purity are obtained at the same time. The invention mainly aims at solving the problems existing in the existing extraction method, solves the problem that the existing products of lutein ester and quercetagetin have high harmful residue, and solves the problem that the lutein ester active substances are easy to damage.
Detailed Description
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise, and furthermore, the terms "comprise" and "have" and any variations thereof, are intended to cover a non-exclusive inclusion, such that a process, method, system, article, or apparatus that comprises a list of steps or elements is not necessarily limited to those steps or elements explicitly listed, but may include other steps or elements not expressly listed or inherent to such process, method, article, or apparatus.
It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict.
The invention is further illustrated by the following specific examples, of which example 1 is the best mode of practice.
The marigold flowers in the embodiments are from Shandong Tianyin Biotechnology Co., Ltd, and can be directly purchased in the market, and marigold granules are obtained through conventional processes such as drying, granulating and the like.
Example 1
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting 116kg of mixed liquid with butane at 1:5 temperature of 40 deg.C for 30min for 4 times.
2) Concentrating each extractive solution under reduced pressure, mixing the 4 concentrated extracts, the concentration of the extract is 95%, and the concentrate quality is 6.03 kg.
3) Adding 80 vol% methanol 42kg into the above concentrated solution, heating at 70 deg.C and stirring for 60min, slowly cooling to 50 deg.C, standing for 6 hr to obtain lutein ester as lower oil layer and quercetagetin as upper layer.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 2
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, and adding the compressed materials with the mass ratio of dimethyl ether: extracting 106kg of mixed liquid with butane at 45 deg.C for 40min for 4 times.
2) Concentrating each extractive solution under reduced pressure, mixing the 4 concentrated extracts, the concentration of the extract is 95%, and the concentrate quality is 6.01 kg.
3) Adding methanol 48.08kg with volume ratio of 82% into the above concentrated solution, heating and stirring at 80 deg.C for 55min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetagetin.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 3
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting 122kg of butane-1: 4.7 mixed liquid at 35 deg.C for 25min for 4 times.
2) Concentrating each extractive solution under reduced pressure, mixing the 4 concentrated extracts, the concentration of the extract is 94%, and the concentrate quality is 6.01 kg.
3) Adding 78% methanol 36.06kg, heating at 75 deg.C under stirring for 58min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetagetin.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 4
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting with butane (1: 4) mixed liquid (100 kg) at 30 deg.C for 5 times, each for 20 min.
2) Concentrating each extractive solution under reduced pressure, mixing 5 concentrated extracts, the concentration of the extract is 93%, and the concentrate quality is 5.95 kg.
3) Adding 80 vol% methanol 35.7kg into the above concentrated solution, heating and stirring at 85 deg.C for 52min, slowly cooling to 50 deg.C, standing for 6 hr to obtain lutein ester as lower oil layer and quercetagetin as upper layer.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 5
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting with mixed liquid of butane 1:6 (160 kg) at 40 deg.C for 50min for 4 times.
2) Concentrating each extractive solution under reduced pressure, mixing the 4 concentrated extracts, the concentration of the extract is 95.5%, and the concentrate quality is 6.03 kg.
3) Adding 80 vol% methanol 54.27kg into the above concentrated solution, heating and stirring at 68 deg.C for 60min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetin marigold.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 6
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting with mixed liquid of butane 1:2 (60 kg) at 50 deg.C for 6 times (15 min each time).
2) Concentrating each extractive solution under reduced pressure, mixing 6 concentrated extracts, the concentration of the extract is 96%, and the concentrate quality is 5.89 kg.
3) Adding 85 vol% methanol 58.9kg into the above concentrated solution, heating and stirring at 65 deg.C for 65min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetagetin.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 7
1) Taking 20kg of marigold flower particles with the lutein content of 28g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting with mixed solution of butane 1:8 (240 kg) at 25 deg.C for 60min for 3 times.
2) Concentrating each extractive solution under reduced pressure, mixing the 3 concentrated extracts, the concentration of the extract is 92%, and the concentrate mass is 6.04 kg.
3) Adding 75% methanol 30.2kg, heating at 90 deg.C under stirring for 50min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetagetin.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 8
1) Taking 25kg of marigold flower particles with the lutein content of 26g/kg, transferring the marigold flower particles into a subcritical extraction kettle, adding the compressed materials with the mass ratio of dimethyl ether: extracting butane (1: 4) with mixed liquid 100kg at 40 deg.C for 30min for 4 times;
2) concentrating each extractive solution under reduced pressure, mixing the 4 concentrated extracts, wherein the concentration of the extract is 94%, and the mass of the concentrate is 7.4 kg.
3) Adding 84% methanol 70kg, heating at 70 deg.C, stirring for 60min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetagetin.
Discharging the lower-layer lutein ester, and continuously concentrating to obtain a lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
Example 9
1) Taking 10kg of marigold flower particles with the lutein content of 30g/kg, transferring the marigold flower particles into a subcritical extraction kettle, and adding the compressed materials with the mass ratio of dimethyl ether: extracting 100kg of butane-1: 3 mixed liquid at 45 deg.C for 30min for 4 times;
2) concentrating each extractive solution under reduced pressure, mixing the 4 concentrated extracts, the concentration of the extract is 94%, and the concentrate quality is 7.4 kg.
3) Adding 95 vol% methanol 75kg into the above concentrated solution, heating at 70 deg.C and stirring for 60min, slowly cooling to 50 deg.C, standing for 6 hr, wherein the lower oil layer is lutein ester, and the upper layer is quercetagetin.
Discharging the next lutein ester, and continuously concentrating to obtain lutein ester product; cooling the upper layer of quercetagetin layer to 30 deg.C, standing for 120min, filtering, and drying to obtain quercetagetin.
And (3) detecting the quercetin:
the mobile phase A is 2% phosphoric acid solution, the phase B is ethylene wax, and the analysis is carried out by adopting gradient elution (the conditions of the gradient elution are shown in the table 1); the elution flow rate is 1 mL/min; column temperature: 40 ℃; chromatographic column CORTECS C18 column (4.6mm × 50mm, 2.7 μm particle size); ultraviolet detector wavelength: 260 nm; sample introduction amount: 2 μ L.
TABLE 1
| Time min | Flow rate, mL/min | A，％ | B，％ |
| Initial | 1 | 88.0 | 12.0 |
| 5.0 | 1 | 88.0 | 12.0 |
| 5.5 | 1 | 10.0 | 90.0 |
| 7.5 | 1 | 10.0 | 90.0 |
| 8.0 | 1 | 88.0 | 12.0 |
| 9.0 | 1 | 88.0 | 12.0 |
The lutein ester detection method comprises the following steps:
detecting the content of lutein ester by ultraviolet spectrophotometry at 445 nm.
The results of the lutein ester and quercetin lutein assay are shown in Table 2.
TABLE 2
As can be seen from the above examples, the lutein ester and the champs Ellis skin marigold obtained by extraction have higher yield and purity by adopting the method of the invention.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are within the protection scope of the technical solution of the present invention.
Claims (10)
1. A method for extracting lutein ester and quercetagetin from marigold flowers is characterized by comprising the following steps:
1) subcritical extracting marigold flower by using a mixed solvent of dimethyl ether and butane, wherein the mass ratio of the marigold flower to the mixed solution is 1: 3-12, and the mass ratio of the dimethyl ether to the butane in the mixed solvent is 1: 2-8, so as to obtain an extracting solution;
2) concentrating the extracting solution into a mixture containing lutein ester and quercetagetin, wherein the solid content in the mixture is 92-96%;
3) extracting and separating the mixture obtained in the step 2) by using a methanol solvent to obtain two products of quercitrin and lutein ester.
2. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the mass ratio of the marigold flowers to the mixed solution in the step 1) is 1:5 to 8.
3. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the mass ratio of the marigold flowers to the mixed solution in the step 1) is 1: 5.3 to 6.1.
4. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the mass ratio of dimethyl ether to butane in the mixed solvent in the step 1) is 1:4 to 6.
5. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the mass ratio of dimethyl ether to butane in the mixed solvent in the step 1) is 1:4.7 to 5.2.
6. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the subcritical extraction in the step 1) is carried out at the temperature of 25-50 ℃, the extraction times are 3-6 times, and the extraction time of each time is 15-60 min.
7. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the volume fraction of the methanol in the methanol solvent in the step 3) is 75-85%.
8. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the mass ratio of the mixture to the methanol solvent in the step 3) is 1:5 to 10.
9. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the extraction separation in step 3) is carried out at a temperature of 65-90 ℃.
10. The method of claim 1, wherein the method comprises extracting lutein esters and quercetin from marigold flowers, wherein the method comprises the following steps:
the solid content in the mixture in the step 2) is 94-95%.
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