WO2020228786A1 - Procédé industrialisé d'extraction rapide et efficace de xanthophylle et de quercétagétine - Google Patents

Procédé industrialisé d'extraction rapide et efficace de xanthophylle et de quercétagétine Download PDF

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WO2020228786A1
WO2020228786A1 PCT/CN2020/090320 CN2020090320W WO2020228786A1 WO 2020228786 A1 WO2020228786 A1 WO 2020228786A1 CN 2020090320 W CN2020090320 W CN 2020090320W WO 2020228786 A1 WO2020228786 A1 WO 2020228786A1
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marigold
hexane
quercetin
extraction
volume ratio
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PCT/CN2020/090320
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English (en)
Chinese (zh)
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卢庆国
连运河
吴迪
王欢欢
吴娟娟
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晨光生物科技集团股份有限公司
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    • 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
    • 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
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention belongs to the field of extraction of natural effective ingredients, and specifically relates to a method for extracting lutein and quercetin marigold from marigold flowers.
  • Marigold is rich in functional ingredients, among which flavonoids contain a variety of flavonoids, such as quercetin marigold, 6-hydroxykaempferol, and marigold, as well as some amino acids.
  • marigold is also rich in lutein and so on.
  • the extraction method of lutein and flavonoids mainly adopts a stepwise extraction method, that is, first extract lutein with n-hexane, and then use solvent to treat marigold flower meal to obtain flavonoid products.
  • Chinese patent 201410104645.X uses two-phase aqueous solvent for extraction; mainly extracting a mixture of lutein and flavonoids.
  • Chinese patent 201811188771.2 uses a mixed solvent of petroleum ether and acetone for extraction.
  • the separation method selected in this patent is to separate after adding water. The operation is more complicated, and it is also impossible to separate high-purity quercetin marigold. Only longevity can be obtained. Chrysanthemum flavonoid mixture.
  • the method for preparing high-purity quercetin marigold in the prior art mainly uses chromatographic separation.
  • Chinese patent CN201410708334.4 discloses that high-purity quercetin marigold can be extracted by one-dimensional liquid chromatography and two-dimensional liquid chromatography.
  • Chinese patent 201610108596.6 is to prepare quercetin marigold with a content of more than 85% through repeated centrifugation, filtration, washing and other methods. There is no report about obtaining high content of quercetin marigold through simple separation and purification.
  • the invention relates to an industrialized method for extracting lutein and quercetin marigold with simple steps and quickly and efficiently.
  • the main improvement is that a mixture of n-hexane and acetone solution is used as an extractant to extract marigold flower particles.
  • the volume fraction of acetone in the acetone solution is 80-100%.
  • the marigold flower particles are extracted with the above-mentioned mixed solution of n-hexane and 80-100% acetone.
  • the main components obtained by extraction are lutein and quercetin marigold.
  • Other impurity components are very high at the acetone concentration in this range.
  • Rarely proposed, high purity quercetin marigold and lutein can be obtained through simple subsequent separation and purification.
  • the volume ratio of the n-hexane to the acetone solution is less than 1:3.
  • the dosage ratio of n-hexane and acetone has an important influence on the extraction of quercetin marigold, and this ratio is more conducive to the complete extraction of quercetin marigold in marigold flower particles.
  • the volume ratio of the n-hexane to the acetone solution is 1:3-5. Under this preferred ratio, it can not only ensure that the quercetin marigold in the marigold flower particles is nearly completely extracted, but also can effectively save solvent consumption and production costs.
  • the mass-volume ratio of the marigold flower particles to the extractant is less than 1:4, and this ratio is more conducive to the complete extraction of lutein and quercetin marigold in the marigold flower particles.
  • the mass-to-volume ratio is 1:4-7. Under this optimal ratio, it can not only ensure that the lutein and quercetin marigold in the marigold flower particles are extracted as completely as possible, but also can effectively save solvent consumption and production costs.
  • the extraction temperature is 20-55°C, and the extraction time is 2-8h.
  • the specific extraction operation may be extraction methods commonly used in the art such as leaching and countercurrent extraction.
  • the extraction liquid in which the mixture is dissolved is evaporated before extraction, until the extractant therein is completely volatilized to obtain a mixture.
  • it further includes the operation of separating the extracted lutein and quercetin marigold, and the specific operation is to extract the extracted mixture with n-hexane.
  • the mass-volume ratio of the mixture to the n-hexane is less than 1:3.
  • the mass-volume ratio of the mixture to the n-hexane is 1:3-5.
  • the extraction temperature is 20-55°C, and the extraction time is 2-8h.
  • the extraction can be performed by conventional operations in the art.
  • the method of the present invention includes the following steps:
  • the yield of quercetin marigold is more than 90%, and the purity is more than 95%, which can also ensure that the lutein also has a higher yield.
  • the volume ratio of the n-hexane to the acetone solution is 1:3 to 5; the mass to volume ratio of the marigold flower particles to the extractant is 1:4 to 7.
  • the production cost can be better reduced under the premise that the purity of quercetin marigold is more than 95% and the yield is more than 90%, which is more conducive to large-scale industrial application.
  • the acetone solution of the present invention is an aqueous solution of acetone, and the mass and volume in the mass-volume ratio are both standard units. In the process of the ratio, gram corresponds to milliliter and kilogram corresponds to liter.
  • Another object of the present invention is to protect the lutein products and quercetin marigold products prepared by the method of the present invention.
  • the method of the present invention can extract high-purity quercetin marigold through simple extraction steps, and the obtained product can be directly applied to industrial production. After further optimization, the purity of quercetin marigold is more than 95%, and the yield of quercetin marigold is more than 90%. Compared with the complicated methods such as chromatography in the prior art, it is a very The method for efficiently extracting quercetin marigold has low extraction cost and short time consumption, and is suitable for industrialized large-scale production.
  • the method of the present invention can also extract high-quality lutein while extracting quercetin marigold, its purity is greater than 18%, the yield is greater than 99%, and the separation method of the two is very simple, only through n-hexane Simple extraction is enough, and the operation is simple.
  • the method of the present invention does not add water during the extraction process, does not require distillation solvents, has low process cost, no waste water generation, and is environmentally friendly.
  • Figure 1 is a liquid chromatogram of the quercetin marigold product obtained in Example 1.
  • the marigold flower particles involved in the embodiments are marigold flower particles obtained by fermentation, pressing, drying, crushing, and granulation of marigold flowers.
  • This embodiment relates to the extraction method of the present invention, including the following steps:
  • This embodiment relates to the extraction method of the present invention, including the following steps:
  • This embodiment relates to the extraction method of the present invention, including the following steps:
  • Example 3 Compared with Example 3, the difference is that in the step 1), the volume ratio of n-hexane and acetone solution is 1:2.
  • the lutein in step (2) is concentrated in the liquid phase to obtain 17.54 kg of the lutein product. Analysis by liquid chromatography showed that its purity was 18.61%, and its content yield was 96.71%.
  • the quercetin marigold in (2) was dried in a solid phase to obtain 5.07 kg of the quercetin marigold product, which was analyzed by liquid chromatography, the purity was 95.76%, and the content yield was 78.24%.
  • Example 3 Compared with Example 3, the difference is that in the step 1), the volume fraction of acetone in the acetone solution is 70%.
  • step (2) The lutein in step (2) is concentrated in the liquid phase to obtain 16.56 kg of lutein product. Analysis by liquid chromatography showed that its purity was 18.79% and the content yield was 92.21%.
  • the quercetin marigold in (2) was dried in a solid phase to obtain 7.14 kg of the quercetin marigold product, which was analyzed by liquid chromatography and its purity was 79.16%, and the content yield was 91.22%.
  • Example 3 Compared with Example 3, the difference is that in the step 2), extraction is performed with ethyl acetate solvent, and the mass-volume ratio of the mixture to the extract is 1:4.
  • step (2) The lutein in step (2) is concentrated in the liquid phase to obtain 16.45 kg of lutein product. Analysis by liquid chromatography showed that its purity was 13.76%, and its content yield was 67.08%.
  • the quercetin marigold in (2) was dried in a solid phase to obtain 7.35 kg of the quercetin marigold product, which was analyzed by liquid chromatography, and its purity was 75.68% and the content yield was 89.77%.
  • the difference is that in the step 1), the ratio of marigold flower particles to extraction solvent is 1:2.
  • step (2) The lutein in step (2) is concentrated in the liquid phase to obtain 14.69 kg of lutein product. Analysis by liquid chromatography showed that its purity was 18.62%, and its content yield was 81.03%.
  • the quercetin marigold in (2) is solid-phase dried to obtain 4.51 kg of the quercetin marigold product, which is analyzed by liquid chromatography, and its purity is 95.23%, and the content yield is 69.27%.
  • the invention provides an industrialized method for extracting lutein and quercetin marigold quickly and efficiently.
  • the method of the present invention uses a mixture of n-hexane and acetone solution as an extractant to extract marigold flower particles, and the volume fraction of acetone in the acetone solution is 80-100%.
  • the mixed extractant of the present invention has very high selectivity to lutein and quercetin marigold, and can effectively extract the above two effective components, and after simple separation, lutein and high-purity quercetin marigold can be obtained
  • the product has simple process, low production cost, is conducive to industrialized production, and has good economic value and application prospects.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention se rapporte au domaine de l'extraction de produits naturels, et concerne en particulier un procédé industrialisé d'extraction rapide et efficace de xanthophylle et de quercétagétine. L'amélioration principale du procédé réside dans le fait qu'une solution mixte de n-hexane et une solution d'acétone sont utilisées en tant qu'agent d'extraction pour extraire des particules de fleur de tagète, la fraction volumique d'acétone dans la solution d'acétone étant de 80 % à 100 %. L'agent d'extraction mixte selon la présente invention a une sélectivité très élevée vis-à-vis de la xanthophylle et de la quercétagétine, et peut être utilisé pour extraire de manière efficace les deux composants actifs, puis, des produits de xanthophylle et de quercétagétine de haute pureté peuvent être obtenus par simple séparation; le procédé industrialisé a un processus simple, un faible coût de production et mène à une production industrialisée.
PCT/CN2020/090320 2019-05-14 2020-05-14 Procédé industrialisé d'extraction rapide et efficace de xanthophylle et de quercétagétine WO2020228786A1 (fr)

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CN110003071B (zh) * 2019-05-14 2021-03-23 晨光生物科技集团股份有限公司 一种快速高效地提取叶黄素和槲皮万寿菊素的工业化方法
CN110776449B (zh) * 2019-10-22 2021-04-09 晨光生物科技集团股份有限公司 一种提取叶黄素和槲皮万寿菊素的工业化方法
CN110746331B (zh) * 2019-10-22 2021-04-09 晨光生物科技集团股份有限公司 一种从万寿菊中提取叶黄素和槲皮万寿菊素的工业化方法
CN113367337B (zh) * 2020-03-10 2023-02-24 晨光生物科技集团股份有限公司 一种包含槲皮万寿菊素的组合物
CN114052247B (zh) * 2020-08-06 2023-06-16 晨光生物科技集团股份有限公司 一种含槲皮万寿菊素、6-羟基山奈酚和没食子酸的抗氧化组合物

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