CN110003071B - Industrial method for quickly and efficiently extracting lutein and quercetagetin - Google Patents
Industrial method for quickly and efficiently extracting lutein and quercetagetin Download PDFInfo
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- CN110003071B CN110003071B CN201910397773.0A CN201910397773A CN110003071B CN 110003071 B CN110003071 B CN 110003071B CN 201910397773 A CN201910397773 A CN 201910397773A CN 110003071 B CN110003071 B CN 110003071B
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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- 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
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- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Abstract
The invention relates to the field of natural product extraction, and particularly relates to an industrial method for quickly and efficiently extracting lutein and quercetagetin, which is mainly improved in that mixed liquid of normal hexane and an acetone solution is used as an extracting agent to extract marigold flower particles, and the volume fraction of acetone in the acetone solution is 80-100%. The mixed extractant of the invention has very high selectivity to lutein and quercetagetin, can effectively extract the two effective components, and can obtain lutein and high-purity quercetagetin products by simple separation, the process is simple, the production cost is low, and the invention is beneficial to industrialized production.
Description
Technical Field
The invention belongs to the field of extraction of natural active ingredients, and particularly relates to a method for extracting lutein and quercetagetin from marigold flowers.
Background
Marigold contains abundant functional components, wherein the flavonoids contain various flavone components such as quercetol, 6-hydroxy kaempferol, marigold and the like, and also contain amino acids and the like. In addition, marigold also contains abundant xanthophyll. At present, the extraction method of lutein and flavone mainly adopts a step-by-step extraction method, namely, lutein is extracted by using normal hexane, and then marigold flower meal is treated by using a solvent to obtain a flavone product. In addition, two patents are extracted by using a mixed solvent, for example, in the chinese patent 201410104645.X, a double aqueous phase solvent is used for extraction; mainly extracting to obtain a mixture of lutein and flavone. Chinese patent 201811188771.2 adopts mixed solvent of petroleum ether and acetone for extraction, and the separation mode selected in the patent is that water is added for separation, the operation is complicated, and high-purity quercetagetin cannot be separated, and only marigold flavone mixture can be obtained. In the prior art, chromatographic separation is mainly used for preparing high-purity quercetagetin. For example, Chinese patent CN201410708334.4 discloses that high-purity quercetagetin is obtained by one-dimensional liquid chromatography and two-dimensional liquid chromatography. Chinese patent 201610108596.6 discloses that quercetin with content higher than 85% is obtained by repeated centrifugation, filtration and washing, and there is no report on obtaining high content quercetin by simple separation and purification.
Disclosure of Invention
The invention relates to an industrial method which has simple steps and can quickly and efficiently extract lutein and quercetagetin, and the main improvement is that mixed solution of normal hexane and acetone solution is used as an extracting agent to extract marigold flower particles, and the volume fraction of acetone in the acetone solution is 80-100%.
The mixed solution of the normal hexane and the acetone with the concentration of 80-100% is adopted to extract marigold flower particles, main components obtained by extraction are lutein components and quercetagetin components, other impurity components are rarely extracted under the acetone concentration in the range, and high-purity quercetagetin and lutein can be obtained through subsequent simple separation and purification.
Preferably, the volume ratio of the n-hexane to the acetone solution is less than 1: 3. the dosage ratio of the n-hexane and the acetone has important influence on the extraction of the quercetagetin, and the quercetagetin in the marigold flower particles can be completely extracted more favorably under the condition of the ratio.
Further preferably, the volume ratio of the n-hexane to the acetone solution is 1: 3-5. Under the optimal proportion, not only can the quercetagetin in the marigold flower granules be extracted nearly completely, but also the solvent consumption and the production cost can be effectively saved.
Preferably, the mass-to-volume ratio of the marigold flower particles to the extractant is less than 1:4, at the ratio, the lutein and the quercetagetin in the marigold flower particles are more favorably and completely extracted.
Further preferably, the mass-to-volume ratio is 1:4 to 7. Under the optimal proportion, the lutein and the quercetagetin in the marigold flower particles can be completely extracted as far as possible, and the solvent consumption and the production cost can be effectively saved.
Preferably, the extraction temperature is 20-55 ℃, and the extraction time is 2-8 h.
Preferably, the specific operation of the extraction can be leaching, countercurrent extraction and other extraction methods commonly used in the field.
Preferably, the extraction solution in which the mixture is dissolved is evaporated before extraction until the extractant is completely volatilized to obtain the mixture.
Preferably, the method further comprises the operation of separating the lutein and quercetagetin obtained by extraction, wherein the operation is to extract the mixture obtained by extraction by n-hexane.
Preferably, the mass-to-volume ratio of the mixture to the n-hexane is less than 1: 3.
further preferably, the mass-to-volume ratio of the mixture to the n-hexane is 1:3 to 5.
Preferably, the extraction temperature is 20-55 ℃, and the extraction time is 2-8 h.
Preferably, the extraction can be carried out using procedures conventional in the art.
Preferably, the method of the present invention comprises the steps of:
1) extracting marigold flower particles by using a mixed solution of the normal hexane and the acetone solution as an extracting agent, and volatilizing the extracting agent completely to obtain a mixture, wherein the volume fraction of acetone in the acetone solution is 80-100%; the volume ratio of the n-hexane to the acetone solution is less than 1: 3; the mass-volume ratio of the marigold flower particles to the extractant is less than 1: 4;
2) and (3) extracting the mixture by using normal hexane, then carrying out solid-liquid separation, drying a solid phase to obtain a quercetagetin product, and concentrating a liquid phase to obtain a lutein product.
By adopting the preferable scheme for extraction, the yield of the quercetagetin is over 90 percent, the purity of the quercetagetin is over 95 percent, and the lutein can also be ensured to have higher yield.
More preferably, in the above scheme, the volume ratio of the n-hexane to the acetone solution is 1: 3-5; the mass volume ratio of the marigold flower particles to the extractant is 1:4 to 7.
Through the further optimized operation, the production cost can be better reduced on the premise that the purity of the quercetagetin is more than 95% and the yield is more than 90%, and the method is more favorable for industrial large-scale application.
The acetone solution is an aqueous solution of acetone, the mass and the volume in the mass-volume ratio are standard units, and in the ratio process, g corresponds to ml, and kg corresponds to L.
Another purpose of the invention is to protect the lutein product and the quercetagetin product prepared by the method.
The invention has the following beneficial effects:
1) the method can extract high-purity quercetagetin by simple extraction steps, and the obtained product can be directly suitable for industrial production. After a further optimization scheme, the purity of the quercetagetin is more than 95%, and the yield of the quercetagetin is more than 90%, compared with the prior art which adopts complicated methods such as chromatography, the method is a method for extracting the quercetagetin with high efficiency, has low extraction cost and short time consumption, and is suitable for industrialized large-scale production.
2) The method can extract high-quality lutein with purity of more than 18% and yield of more than 99% while extracting quercetagetin, and the separation method of the quercetin and the lutein is very simple, and the method is simple to operate and can be simply extracted by only n-hexane.
3) The method does not add water in the extraction process, does not need a rectification solvent, has low process cost, does not generate waste water, and is green and environment-friendly.
Drawings
FIG. 1 is a liquid chromatogram of the quercetagetin product obtained in example 1.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The marigold flower particles related in the embodiment are marigold flower particles obtained by fermenting, squeezing, drying, crushing and granulating marigold flowers.
Example 1
The embodiment relates to an extraction method, which comprises the following steps:
(1) feeding 100kg of marigold flower particles, mixing the marigold flower particles with n-hexane and 80% acetone solution in a volume ratio of 1:3, leaching the marigold flower particles at the temperature of 20 ℃ according to a total material-liquid ratio of 1:4, wherein the leaching time is 1 hour each time, repeatedly extracting for 3 times, mixing leaching solutions, and concentrating the leaching solution until no distillate exists to obtain 24.47kg of solid mixture;
(2) adding n-hexane into the mixture obtained in the step (1) according to the mass volume ratio of 1:3 for extraction, extracting at room temperature for 3 hours, and then performing solid-liquid two-phase separation to respectively obtain a liquid phase containing lutein and a solid phase containing quercetagetin;
(3) and (3) concentrating the lutein liquid phase in the step (2) to obtain 18.59kg of lutein products, and analyzing by liquid chromatography, wherein the purity of the lutein products is 18.02 percent, and the content yield of the lutein products is 99.25 percent.
(4) Drying the solid phase of quercetagetin in (2) to obtain 5.88kg of quercetagetin product, and analyzing by liquid chromatography (liquid chromatogram is shown in figure 1, peak between 4.0 min-4.5 min in figure is quercetagetin, peak time is 4.131), purity is 95.15%, and content yield is 90.24%.
Example 2
The embodiment relates to an extraction method, which comprises the following steps:
(1) feeding 100kg of marigold flower particles, mixing the marigold flower particles with n-hexane and 100% of acetone according to a volume ratio of 1:3, leaching the marigold flower particles according to a material ratio of 1:6 at 55 ℃, wherein the leaching time is 1 hour each time, repeatedly extracting for 3 times, mixing leaching solutions, and then concentrating until no distillate exists to obtain 23.81kg of solid matter;
(2) adding n-hexane into the mixture obtained in the step (1) according to the mass volume ratio of 1:5 for extraction, extracting at 30 ℃ for 3h, and then carrying out solid-liquid two-phase separation to respectively obtain a liquid-phase lutein phase and a solid-phase quercetagetin phase.
(3) And (3) concentrating the lutein liquid phase in the step (2) to obtain 17.81kg of lutein products. The purity of the product is 18.9% and the content yield is 99.76% by liquid chromatography analysis.
(4) And (3) drying the solid phase of the quercetagetin in the step (2) to obtain 5.99kg of quercetagetin product, wherein the purity of the quercetagetin product is 96.17 percent and the content yield of the quercetagetin product is 92.94 percent through liquid chromatography analysis.
Example 3
The embodiment relates to an extraction method, which comprises the following steps:
(1) feeding 100kg of marigold flower particles, mixing the marigold flower particles with n-hexane and 100% acetone solution in a volume ratio of 1:5, leaching the marigold flower particles according to a material ratio of 1:6 at the temperature of 55 ℃, wherein the leaching time is 1 hour each time, repeatedly extracting for 3 times, mixing leaching solutions, and then concentrating the leaching solutions until no distillate exists to obtain 24.06kg of a solid mixture;
(2) adding n-hexane into the mixture obtained in the step (1) according to the mass volume ratio of 1:5 for extraction, extracting at 50 ℃ for 3 hours, and then carrying out solid-liquid two-phase separation to respectively obtain a liquid-phase lutein phase and a solid-phase quercetagetin phase.
(3) And (3) concentrating the lutein liquid phase in the step (2) to obtain 18.04kg of lutein products. The purity is 18.6% and the content yield is 99.41% by liquid chromatography analysis
(4) And (3) drying the solid phase of the quercetagetin in the step (2) to obtain 6.02kg of quercetagetin product, wherein the purity of the quercetagetin product is 96.48 percent and the content yield of the quercetagetin product is 93.73 percent through liquid chromatography analysis.
Comparative example 1
Compared with the embodiment 3, the difference is that in the step 1), the volume ratio of the normal hexane to the acetone solution is 1: 2.
and (3) concentrating the lutein liquid phase in the step (2) to obtain 17.54kg of lutein products. The purity of the product was 18.61% and the yield was 96.71% by liquid chromatography.
And (3) drying the solid phase of the quercetagetin in the step (2) to obtain 5.07kg of quercetagetin product, wherein the purity of the quercetagetin product is 95.76% and the content yield of the quercetagetin product is 78.24% through liquid chromatography analysis.
Comparative example 2
Compared with example 3, the difference is that in the step 1), the volume fraction of acetone in the acetone solution is 70%.
And (3) concentrating the lutein liquid phase in the step (2) to obtain 16.56kg of lutein products. The purity of the product was 18.79% and the yield was 92.21% by liquid chromatography.
And (3) drying the solid phase of the quercetagetin in the step (2) to obtain 7.14kg of quercetagetin product, wherein the purity of the quercetagetin product is 79.16% and the content yield of the quercetagetin product is 91.22% through liquid chromatography analysis.
Comparative example 3
Compared with example 3, the difference is that in the step 2), ethyl acetate solvent is used for extraction, and the mass-volume ratio of the mixture to the extract is 1: 4.
and (3) concentrating the lutein liquid phase in the step (2) to obtain 16.45kg of lutein products. The purity of the product was 13.76% and the yield was 67.08% by liquid chromatography.
And (3) drying the solid phase of the quercetagetin in the step (2) to obtain 7.35kg of quercetagetin product, wherein the purity of the quercetagetin product is 75.68% and the content yield of the quercetagetin product is 89.77% through liquid chromatography analysis.
Comparative example 4
Compared with example 3, the difference is that in the step 1), the ratio of marigold flower particles to extraction solvent is 1: 2.
and (3) concentrating the lutein liquid phase in the step (2) to obtain 14.69kg of lutein products. The purity of the product is 18.62% and the content yield is 81.03% by liquid chromatography analysis.
And (3) drying the solid phase of the quercetagetin in the step (2) to obtain 4.51kg of quercetagetin product, wherein the purity of the quercetagetin product is 95.23% and the content yield of the quercetagetin product is 69.27% through liquid chromatography analysis.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (6)
1. An industrial method for quickly and efficiently extracting lutein and quercetagetin is characterized by comprising the following steps:
1) extracting flos Tagetis Erectae granule with mixed solution of n-hexane and acetone solution as extractant, and concentrating the obtained extractive solution until the extractant is completely volatilized to obtain mixture; the volume fraction of acetone in the acetone solution is 80-100%; the volume ratio of the n-hexane to the acetone solution is less than or equal to 1: 3; the mass-volume ratio of the marigold flower particles to the extractant is less than or equal to 1: 4;
2) and (3) extracting the mixture by using normal hexane, then carrying out solid-liquid separation, drying a solid phase to obtain a quercetagetin product, and concentrating a liquid phase to obtain a lutein product.
2. The industrial process according to claim 1, characterized in that the volume ratio of the n-hexane to the acetone solution is 1:3 to 5.
3. The industrial process according to claim 1, wherein the mass-to-volume ratio of the marigold flower particles to the extractant is 1:4 to 7.
4. The industrial process according to claim 1, wherein the mass-to-volume ratio of the mixture to the n-hexane in step 2) is less than or equal to 1: 3.
5. the industrial method according to claim 4, wherein the mass-to-volume ratio of the mixture to the n-hexane in the step 2) is 1: 3-5.
6. The industrial method according to any one of claims 1 to 5, wherein the extraction temperature is 20 to 55 ℃ and the extraction time is 2 to 8 hours; and/or, the extraction temperature in the step 2) is 20-55 ℃, and the extraction time is 2-8 h.
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| CN201910397773.0A CN110003071B (en) | 2019-05-14 | 2019-05-14 | Industrial method for quickly and efficiently extracting lutein and quercetagetin |
| PCT/CN2020/090320 WO2020228786A1 (en) | 2019-05-14 | 2020-05-14 | Industrialized method for rapidly and efficiently extracting xanthophyll and quercetagetin |
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| CN110003071B (en) * | 2019-05-14 | 2021-03-23 | 晨光生物科技集团股份有限公司 | Industrial method for quickly and efficiently extracting lutein and quercetagetin |
| CN110776449B (en) * | 2019-10-22 | 2021-04-09 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin |
| CN110746331B (en) * | 2019-10-22 | 2021-04-09 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin from marigold |
| CN113367337B (en) * | 2020-03-10 | 2023-02-24 | 晨光生物科技集团股份有限公司 | A composition containing quercetagetin |
| CN114052247B (en) * | 2020-08-06 | 2023-06-16 | 晨光生物科技集团股份有限公司 | An antioxidant composition containing quercetin, 6-hydroxy kaempferol and gallic acid |
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| CN105693676A (en) * | 2014-11-28 | 2016-06-22 | 天津耀宇生物技术有限公司 | A method of separating and purifying quercetagetin from tagetes erecta |
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| CN1286807C (en) * | 2005-05-27 | 2006-11-29 | 大庆金土地生物科技有限公司 | Lutein extracting process from marigold flower |
| CN102190646B (en) * | 2011-03-29 | 2013-03-13 | 中国农业大学 | Method for preparing high-purity quercetagetin |
| CN103936643B (en) * | 2014-03-20 | 2016-07-06 | 江苏大学 | A kind of method extracting separation Flos Tagetis Erectae Lutein and flavone |
| CN105541775A (en) * | 2016-02-26 | 2016-05-04 | 中国农业大学 | Industrial preparation method of quercetagetin |
| CN109134254B (en) * | 2018-09-28 | 2021-06-01 | 晨光生物科技集团股份有限公司 | Industrial method for preparing high-purity lutein ester |
| CN109232346B (en) * | 2018-10-12 | 2020-04-14 | 晨光生物科技集团股份有限公司 | Industrial preparation method of lutein and marigold flavone |
| CN110003071B (en) * | 2019-05-14 | 2021-03-23 | 晨光生物科技集团股份有限公司 | Industrial method for quickly and efficiently extracting lutein and quercetagetin |
| CN110105257B (en) * | 2019-05-15 | 2021-07-27 | 晨光生物科技集团股份有限公司 | Industrial method for synchronously extracting lutein and quercetagetin |
| CN110372554B (en) * | 2019-06-28 | 2021-04-23 | 晨光生物科技集团股份有限公司 | Industrial method for quickly and efficiently extracting lutein and quercetagetin |
| CN110776449B (en) * | 2019-10-22 | 2021-04-09 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin |
| CN110746331B (en) * | 2019-10-22 | 2021-04-09 | 晨光生物科技集团股份有限公司 | Industrial method for extracting lutein and quercetagetin from marigold |
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| CN105693676A (en) * | 2014-11-28 | 2016-06-22 | 天津耀宇生物技术有限公司 | A method of separating and purifying quercetagetin from tagetes erecta |
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