WO2020259565A1 - 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 - Google Patents
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 Download PDFInfo
- Publication number
- WO2020259565A1 WO2020259565A1 PCT/CN2020/098038 CN2020098038W WO2020259565A1 WO 2020259565 A1 WO2020259565 A1 WO 2020259565A1 CN 2020098038 W CN2020098038 W CN 2020098038W WO 2020259565 A1 WO2020259565 A1 WO 2020259565A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- marigold
- extraction
- quercetin
- extract
- acetone
- Prior art date
Links
Images
Classifications
-
- 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 present invention relates to the technical field of extraction of plant functional components, in particular to a method for extracting lutein and quercetin marigold from marigold flowers.
- Marigold is one of the main cultivated herb potted flowers in my country, and it is widely used in indoor and outdoor environment layout. With the development of the nutrition and health industry, the international demand for marigolds is increasing. Marigold not only has ornamental value, but also has good medicinal value. The main components of its pharmacological effect are flavonoids, carotenoids, terpenes, glycosides, essential oils and other ingredients.
- the extraction method of lutein and flavonoids is mainly a step-by-step extraction, that is, lutein is first extracted with n-hexane, and then marigold flower meal is treated with a solvent to obtain flavonoid products.
- 201410104645.X uses a 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 quercetin marigold has excellent biological effects such as anti-oxidation.
- 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 relevant report on obtaining high content of quercetin marigold through simple separation and purification.
- the present invention relates to an industrialized method for extracting lutein and quercetin marigold quickly and efficiently, including the following steps:
- the present invention found that the use of acetone solution to extract marigold flowers can selectively and fully extract lutein and quercetin marigold. After adding the above proportion of water, the quercetin marigold and lutein can be improved in the acetone solution and normal The distribution in the alkane, and then liquid-liquid extraction and separation with n-hexane to obtain two products. Strictly control the concentration of acetone and the amount of water added during separation during the whole process, which can fully extract and refine lutein and quercetin marigold to obtain a n-hexane phase containing lutein and quercetin marigold. The acetone phase.
- the mass-volume ratio of the marigold flower particles to the acetone solution is 1:4-20.
- lutein and quercetin marigold can be fully extracted, and the extraction rate is high.
- the mass-volume ratio of the marigold flower particles to the acetone solution is 1:5-10.
- lutein and quercetin marigold can be sufficiently extracted, and the cost can be reduced.
- the extraction is carried out at a temperature of 30-60°C. At the above temperature, the two products can be fully and completely extracted. If the temperature is too low, the extraction is insufficient, and the yield of quercetin marigold will not increase, but the yield of lutein will decrease.
- the extraction time is 2-6h.
- the volume ratio of the extract to the n-hexane is 1:0.3-3.
- quercetin marigold and lutein can be separated well.
- the extraction is carried out at a temperature of 30-50°C.
- the extraction time is 2-6h.
- the volume ratio of the extraction liquid to the water is 1:0.8 to 1.8.
- the mixture formed by the extract and water has very good solubility for quercetin marigold, n-hexane has very good solubility for lutein, and the polarities of the two solutions are different Larger, can realize more ideal separation and purification of lutein and quercetin marigold.
- the volume fraction of the acetone solution is 94-99%.
- concentration of acetone can achieve sufficient extraction of lutein and quercetin marigold, both of which have higher purity and higher extraction rate.
- the acetone concentration is low, the yield of lutein will decrease.
- the yield of quercetin marigold will decrease.
- the method of the present invention includes the following steps:
- Another object of the present invention is to protect the lutein products and quercetin marigold products extracted by the method of the present invention.
- 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.
- the extraction described in the present invention can be performed by methods commonly used in the art, such as leaching or countercurrent extraction.
- the present invention proposes a simple method for extracting lutein and quercetin marigold, which only includes the operations of extraction, concentration, and extraction. Compared with other solutions in the prior art, the extraction method of the present invention has shorter steps, Low cost, suitable for industrialized mass production.
- the present invention selects acetone with a concentration of 90-100% as the extractant, which can extract lutein and quercetin marigold at the same time, and can obtain the two products by strictly controlling the acetone concentration. The rate reaches the highest, and other impurities are rarely extracted. If methanol, ethanol, and other concentrations of acetone solution (such as 70% or 80% concentration) are used, the substances proposed are except for quercetin marigold. It also contains marigold, marigold glycosides, quercetin, 6-hydroxykaempferol and other substances. These substances belong to the flavonoids and are similar in structure and properties to quercetin marigold. Further separation of quercetin marigold The purification process is very difficult. The invention further extracts and separates the acetone phase and the normal hexane phase, which can ensure the purity of the two products.
- the yield of lutein obtained is greater than 95% and the purity is greater than 20%; the yield of quercetin marigold is greater than 95% and the purity is greater than 95%.
- Figure 1 is a liquid chromatographic analysis diagram 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.
- the extraction conditions involved in the examples are a temperature of 50° C. and an extraction time of 5 h.
- This embodiment relates to an industrialized method for extracting lutein and quercetin marigold quickly and efficiently, including the following steps:
- This example relates to an industrialized method for extracting lutein and quercetin marigold quickly and efficiently. Compared with Example 1, the difference is that an acetone solution with a concentration of 94% is used for extraction. The specific steps are:
- This embodiment relates to an industrialized method for quickly and efficiently extracting lutein and quercetin marigold. Compared with Example 1, the difference is that pure acetone is used for extraction in the step 1), and the specific steps are:
- This example relates to an industrialized method for extracting lutein and quercetin marigold quickly and efficiently. Compared with Example 1, the difference is that the step 1) uses an acetone solution with a volume fraction of 90% for extraction. , The specific steps are:
- This example relates to an industrialized method for quickly and efficiently preparing lutein and quercetin marigold. Compared with Example 1, the difference is that the amount of water added is different, and the volume ratio of the extract to water is 1:2, including the following step:
- This example relates to an industrialized method for quickly and efficiently preparing lutein and quercetin marigold. Compared with Example 1, the difference is that the amount of water added is different, and the volume ratio of extract to water is 1:1.67, including the following step:
- This embodiment relates to an industrialized method for quickly and efficiently preparing lutein and quercetin marigold.
- the addition amount of water is different, and the volume ratio of the extract to water is 1:0.9, including the following steps:
- This example relates to an industrialized method for quickly and efficiently preparing lutein and quercetin marigold. Compared with Example 2, the addition amount of water is different, and the volume ratio of the extract to water is 1:2.5, including the following steps:
- Example 1 Compared with Example 1, the difference lies in that an acetone solution with a volume fraction of 85% is used in the extraction process of step 1).
- Example 1 Compared with Example 1, the difference is that the extraction in step 1) is performed at 70°C.
- Example 2 Compared with Example 1, the difference is that the amount of water added in the step 2) is 100L.
- Example 2 Compared with Example 1, the difference is that the addition amount of water in the step 2) is 800L.
- quercetin marigold and lutein were detected by high performance liquid phase and ultraviolet method respectively.
- the high performance liquid chromatography conditions of quercetin marigold were using C18 column with water and acetonitrile as the flow Phase, detected at 360nm.
- the invention provides an industrialized method for extracting lutein and quercetin marigold quickly and efficiently.
- the method of the present invention includes the following steps: 1) Use an acetone solution with a volume fraction of 90 to 100% to extract marigold flower particles to obtain an extract; 2) The volume ratio of water to the extract is 1: 0.5 to 2.5 After mixing, adding n-hexane for extraction, and obtaining lutein products and quercetin marigold products after extraction. Using acetone solution to extract marigold flower particles, lutein and quercetin marigold can be selectively and fully extracted, and after adding water, liquid-liquid extraction and separation with n-hexane are used to obtain two products.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及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，包括如下步骤：1)用体积分数为90～100％的丙酮溶液对万寿菊花颗粒进行提取，得提取液；2)将水与所述提取液按体积比1：0.5～2.5混合，然后加入正己烷进行萃取，萃取后得到叶黄素产品和槲皮万寿菊素产品。采用丙酮溶液对万寿菊花颗粒进行提取，可对叶黄素和槲皮万寿菊素进行选择性地充分提取，加入水后再用正己烷进行液液萃取分离得到两种产品。整个过程中严格控制丙酮浓度以及分离时加入水的量，可对叶黄素和槲皮万寿菊素进行充分的提取以及更好的精制，得到含有叶黄素的正己烷相和含有槲皮万寿菊素的丙酮相。
Description
交叉引用
本申请要求2019年6月28日提交的专利名称为“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”的第2019105795864号中国专利申请的优先权，其全部公开内容通过引用整体并入本文。
本发明涉及植物功能性成分提取的技术领域，具体涉及一种从万寿菊花中提取叶黄素和槲皮万寿菊素的方法。
万寿菊是我国主要栽培的草本盆花之一，且广泛用于室内外环境布置。随着营养健康产业发展，国际上对万寿菊的需求量越来越多。万寿菊不但具有观赏价值外，而且还有很好的药用价值，其起药理作用的主要成分是黄酮类物质、类胡萝卜素类、萜类、糖苷类、精油等成分。
目前关于叶黄素和黄酮提取方法，主要是分步提取，即利用正己烷首先提取叶黄素，然后利用溶剂处理万寿菊花粕得到黄酮类产品。另外有两篇专利是利用混合溶剂提取，201410104645.X中采用双水相溶剂进行提取；主要是提取得到叶黄素和黄酮混合物。中国专利201811188771.2采用石油醚和丙酮的混合溶剂进行提取，该专利中选用的分离方式为加入水后进行分离，操作较为复杂，而且也无法分离得到高纯度的槲皮万寿菊素，仅可得到万寿菊黄酮混合物。
槲皮万寿菊素具有抗氧化等优良的生物功效，现有技术中关于高纯度槲皮万寿菊素的制备方法主要利用色谱分离。如中国专利CN201410708334.4公开通过一维液相色谱和二维液相色谱法提取得到高纯度的槲皮万寿菊素。中国专利201610108596.6是通过反复离心、过滤、洗涤等方法，制备得到含量大于85％的槲皮万寿菊素，还未见通过简单分离纯化得到高含量槲皮万寿菊素的相关报导。
发明内容
本发明涉及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，包括如下步骤：
1)用体积分数为90～100％的丙酮溶液对万寿菊花颗粒进行提取，得提取液；
2)将水与所述提取液按体积比1：0.5～2.5混合，然后加入正己烷进行萃取，萃取后得到叶黄素产品和槲皮万寿菊素产品。
本发明发现，采用丙酮溶液对万寿菊花进行提取，可对叶黄素和槲皮万寿菊素进行选择性地充分提取，加入上述比例的水后改善槲皮万寿菊素和叶黄素在丙酮溶液和正己烷中的分配情况，再用正己烷进行液液萃取分离得到两种产品。整个过程中严格控制丙酮浓度以及分离时加入水的量，可对叶黄素和槲皮万寿菊素进行充分的提取以及更好的精制，得到含有叶黄素的正己烷相和含有槲皮万寿菊素的丙酮相。
优选的，所述万寿菊花颗粒与所述丙酮溶液的质量体积比为1：4～20。在上述范围内，可对叶黄素和槲皮万寿菊素进行充分地提取，提取率较高。
进一步优选的，所述万寿菊花颗粒与所述丙酮溶液的质量体积比为1：5～10。在上述范围内，既可对叶黄素和槲皮万寿菊素进行充分地提取，且能够降低成本。
优选的，所述提取在温度30～60℃的条件下进行。在上述温度下，两种产品能够得到充分完全的提取，温度过低，提取不充分，温度过高槲皮万寿菊素得率也不会增加，叶黄素得率反而会降低。
优选的，提取时间为2～6h。
优选的，所述提取液与所述正己烷的体积比为1：0.3～3。在上述范围内，槲皮万寿菊素和叶黄素能够得到很好的分离。
优选的，所述萃取在温度30～50℃的条件下进行。
优选的，和/或，萃取时间为2～6h。
优选的，所述提取液与所述水的体积比为1：0.8～1.8。在上述体积比 的情况下，提取液与水形成的混合液对槲皮万寿菊素有非常好的溶解性，正己烷对叶黄素有非常好的溶解性，且两种溶液的极性相差较大，可实现对叶黄素和槲皮万寿菊素的更为理想地分离和精制。
优选的，所述丙酮溶液的体积分数为94～99％。采用上述浓度的丙酮，可实现对叶黄素和槲皮万寿菊素的充分提取，二者均具有较高的纯度和较高的提取率。丙酮浓度较低时，叶黄素的得率会有所下降，采用纯丙酮时，槲皮万寿菊素的得率会有所下降。
作为优选的方案，本发明的方法包括步骤如下：
1)用体积分数为94～99％的丙酮溶液在温度30～60℃对万寿菊花颗粒进行提取，得提取液；
2)将水与所述提取液按体积比1：0.8～1.8混合，然后加入正己烷进行萃取，萃取后得到正己烷相中的叶黄素产品和丙酮相中的槲皮万寿菊素产品。
本发明的另一目的是保护本发明所述方法提取得到的叶黄素产品和槲皮万寿菊素产品。
本发明所述的丙酮溶液为丙酮的水溶液，所述的质量体积比中质量和体积均为标准单位，在比的过程中克对应毫升，千克对应升。
本发明所述的提取可采用本领域常用的方法进行，如浸提或逆流萃取等。
本发明具有如下有益效果：
1)本发明提出了一种简单地提取叶黄素和槲皮万寿菊素的方法，仅包括提取、浓缩、萃取的操作，与现有技术中的其他方案相比，本发明的提取方法步骤短、成本低，适用于工业化大规模生产。
2)针对于万寿菊花颗粒，本发明选择浓度为90～100％的丙酮作为提取剂，可以对叶黄素和槲皮万寿菊素同时进行提取，并且通过严格控制丙酮浓度能够将这两种产品的得率达到最高，而其他杂质极少地被提取出来，而如果用甲醇，乙醇，以及其它浓度的丙酮溶液(如70％或80％的 浓度)，提出来的物质里除了槲皮万寿菊素之外还含有万寿菊素、万寿菊苷、槲皮素、6羟基山奈酚等物质，这些物质均属于黄酮类物质，与槲皮万寿菊素结构和性质相似，进一步对槲皮万寿菊素进行分离纯化的过程中难度非常大。本发明进一步通过丙酮相和正己烷相萃取分离，能够保证两种产品的纯度。
3)采用本发明的方法，通过对方案进行优选，所得叶黄素收率大于95％，纯度大于20％；槲皮万寿菊素的收率大于95％，纯度为95％以上。
图1为实施例1所得槲皮万寿菊素产品的液相色谱分析图。
以下实施例用于说明本发明，但不用来限制本发明的范围。
实施例中涉及的万寿菊花颗粒是由万寿菊花经过发酵、压榨、烘干、粉碎、制粒得到的万寿菊花颗粒。
实施例中涉及的萃取的条件为温度50℃，萃取时间5h。
实施例1
本实施例涉及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，包括如下步骤：
1)取万寿菊花颗粒50kg，加入浓度为99％的丙酮溶液300L，在50℃条件下浸提5h。
2)向上述300L的提取液中加入300L的水和100L的正己烷，充分振荡，静置分层，丙酮和水的混合相浓缩过滤得槲皮万寿菊素，(对其进行液相色谱分析，其液相色谱图如图1，由图1可知，槲皮万寿菊素的出峰时间在3.5～4.5min之间，几乎没有其他杂质峰，说明槲皮万寿菊素的纯度非常高)，正己烷相浓缩得叶黄素浸膏。
实施例2
本实施例涉及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，与实施例1相比，其区别在于，采用浓度为94％的丙酮溶液进行提取， 其具体步骤为：
1)取万寿菊花颗粒50kg，加入浓度为94％的丙酮溶液300L，在50℃条件下浸提5h。
2)向上述300L的提取液中加入300L的水和100L的正己烷，充分振荡，静置分层，丙酮和水的混合相浓缩过滤得槲皮万寿菊素。
实施例3
本实施例涉及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，与实施例1相比，其区别仅在于，所述步骤1)中采用纯丙酮进行提取，其具体步骤为：
1)取万寿菊花颗粒50kg，加入丙酮300L，在50℃条件下浸提5h；
2)向上述300L的提取液中加入300L的水和100L的正己烷，充分振荡，静置分层，丙酮和水的混合相浓缩过滤得槲皮万寿菊素。
实施例4
本实施例涉及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，与实施例1相比，其区别仅在于，所述步骤1)中采用体积分数为90％的丙酮溶液进行提取，其具体步骤为：
1)取万寿菊花颗粒50kg，加入90％丙酮300L，在50℃条件下浸提5h；
2)向上述300L的提取液中加入300L的水和100L的正己烷，充分振荡，静置分层，丙酮和水的混合相浓缩过滤得槲皮万寿菊素。
实施例5
本实施例涉及一种快速高效制备叶黄素和槲皮万寿菊素的工业化方法，与实施例1相比，区别在于，水的添加量不同，提取液与水的体积比为1：2，包括如下步骤：
1)取万寿菊花50kg，加入浓度为99％的丙酮溶液300L，在50℃条件下浸提5h。
2)向上述300L的提取液中加入600L的水和100L的正己烷，充分振荡，静置分层，丙酮相浓缩过滤得槲皮万寿菊素，正己烷相浓缩得叶黄素浸膏。
实施例6
本实施例涉及一种快速高效制备叶黄素和槲皮万寿菊素的工业化方法，与实施例1相比，区别在于，水的添加量不同，提取液与水的体积比为1：1.67，包括如下步骤：
1)取万寿菊花50kg，加入浓度为99％的丙酮溶液300L，在50℃条件下浸提5h。
2)向上述300L的提取液中加入500L的水和100L的正己烷，充分振荡，静置分层，丙酮相浓缩过滤得槲皮万寿菊素，正己烷相浓缩得叶黄素浸膏。
实施例7
本实施例涉及一种快速高效制备叶黄素和槲皮万寿菊素的工业化方法，与实施例4相比，水的添加量不同，提取液与水的体积比为1：0.9，包括如下步骤：
1)取万寿菊花50kg，加入浓度为90％的丙酮溶液300L，在50℃条件下浸提5h。
2)向上述300L的提取液中加入270L的水和100L的正己烷，充分振荡，静置分层，丙酮相浓缩过滤得槲皮万寿菊素，正己烷相浓缩得叶黄素浸膏。
实施例8
本实施例涉及一种快速高效制备叶黄素和槲皮万寿菊素的工业化方法，与实施例2相比，水的添加量不同，提取液与水的体积比为1：2.5，包括如下步骤：
1)取万寿菊花颗粒50kg，加入浓度为96％的丙酮溶液300L，在50℃条件下浸提5h。
2)向上述300L的提取液中加入750L的水和100L的正己烷，充分振荡，静置分层，丙酮和水的混合相浓缩过滤得槲皮万寿菊素。
对比例1
与实施例1相比，其区别在于，所述步骤1)提取的过程中采用体积分数为85％的丙酮溶液。
对比例2
与实施例1相比，其区别在于，所述步骤1)的提取在70℃的条件下进行。
对比例3
与实施例1相比，其区别在于，所述步骤2)中水的添加量为100L。
对比例4
与实施例1相比，其区别在于，所述步骤2)中水的添加量为800L。
实验例
分别采用高效液相和紫外法对得到的槲皮万寿菊素和叶黄素的含量分别进行检测，其中，槲皮万寿菊素的高效液相色谱条件为采用C18柱，以水和乙腈作为流动相，在360nm处进行检测。
表1
由以上实施例可以看出，采用本发明的方法，提取得到的叶黄素和槲皮万寿菊素的得率和纯度均很高，尤其是槲皮万寿菊素的含量是目前工业化生产的专利中所不能达到的。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所 做的这些修改或改进，均属于本发明要求保护的范围。
本发明提供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。本发明所述方法包括如下步骤：1)用体积分数为90～100％的丙酮溶液对万寿菊花颗粒进行提取，得提取液；2)将水与所述提取液按体积比1：0.5～2.5混合，然后加入正己烷进行萃取，萃取后得到叶黄素产品和槲皮万寿菊素产品。采用丙酮溶液对万寿菊花颗粒进行提取，可对叶黄素和槲皮万寿菊素进行选择性地充分提取，加入水后再用正己烷进行液液萃取分离得到两种产品。整个过程中严格控制丙酮浓度以及分离时加入水的量，可对叶黄素和槲皮万寿菊素进行充分的提取以及更好的精制，得到含有叶黄素的正己烷相和含有槲皮万寿菊素的丙酮相，具有较好的经济价值和应用前景。
Claims (9)
- 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，其特征在于，包括如下步骤：1)用体积分数为90～100％的丙酮溶液对万寿菊花颗粒进行提取，得提取液；2)将水与所述提取液按体积比1：0.5～2.5混合，然后加入正己烷进行萃取，萃取后得到叶黄素产品和槲皮万寿菊素产品。
- 根据权利要求1所述的工业化方法，其特征在于，所述万寿菊花颗粒与所述丙酮溶液的质量体积比为1：4～20，优选1：5～10。
- 根据权利要求1或2所述的工业化方法，其特征在于，所述提取在温度30～60℃的条件下进行，和/或，提取时间为2～6h。
- 根据权利要求1～3任一项所述的工业化方法，其特征在于，所述萃取的条件为在温度30～50℃的条件下进行，和/或，萃取时间为2～6h。
- 根据权利要求1～4任一项所述的工业化方法，其特征在于，所述提取液与所述正己烷的体积比为1：0.3～3。
- 根据权利要求1～5任一项所述的工业化方法，其特征在于，所述丙酮溶液的体积分数为94～99％。
- 根据权利要求1～6任一项所述的工业化方法，其特征在于，所述提取液与所述水的体积比为1：0.8～1.8。
- 根据权利要求1～7任一项所述的工业化方法，其特征在于，包括如下步骤：1)用体积分数为94～99％的丙酮溶液在温度30～60℃对万寿菊花颗粒进行提取，得提取液；2)将水与所述提取液按体积比1：0.8～1.8混合，然后加入正己烷进行萃取，萃取后得到正己烷相中的叶黄素产品和丙酮相中的丙酮相中的槲皮万寿菊素产品。
- 权利要求1～8任一项所述工业化方法提取得到的叶黄素产品和槲皮万寿菊素产品。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910579586.4A CN110372554B (zh) | 2019-06-28 | 2019-06-28 | 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 |
| CN201910579586.4 | 2019-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2020259565A1 true WO2020259565A1 (zh) | 2020-12-30 |
Family
ID=68251240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CN2020/098038 WO2020259565A1 (zh) | 2019-06-28 | 2020-06-24 | 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 |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN110372554B (zh) |
| WO (1) | WO2020259565A1 (zh) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| CN113615767B (zh) * | 2020-05-06 | 2023-05-05 | 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饲料及其用途 |
| 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 |
| CN114052246B (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和没食子酸的抗氧化组合物 |
| CN112999252B (zh) * | 2021-03-03 | 2022-05-20 | 晨光生物科技集团股份有限公司 | 一种连续提取高含量万寿菊黄酮的工业化方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101756168A (zh) * | 2008-12-25 | 2010-06-30 | 中国科学院兰州化学物理研究所 | 金盏花黄色素的提取方法 |
| CN102190646A (zh) * | 2011-03-29 | 2011-09-21 | 中国农业大学 | 一种高纯度槲皮万寿菊素制备方法 |
| CN102516335A (zh) * | 2011-12-08 | 2012-06-27 | 中国农业大学 | 一种从万寿菊残渣中提取黄酮类化合物的方法 |
| CN105541775A (zh) * | 2016-02-26 | 2016-05-04 | 中国农业大学 | 一种槲皮万寿菊素工业化制备方法 |
| CN105693676A (zh) * | 2014-11-28 | 2016-06-22 | 天津耀宇生物技术有限公司 | 从万寿菊中分离纯化槲皮万寿菊素的方法 |
| CN109232346A (zh) * | 2018-10-12 | 2019-01-18 | 晨光生物科技集团股份有限公司 | 一种叶黄素和万寿菊黄酮的工业化制备方法 |
| CN109498614A (zh) * | 2018-11-29 | 2019-03-22 | 扬州大学 | 猫眼草黄素及青蒿素工业废弃物丙酮层的新用途 |
-
2019
- 2019-06-28 CN CN201910579586.4A patent/CN110372554B/zh active Active
-
2020
- 2020-06-24 WO PCT/CN2020/098038 patent/WO2020259565A1/zh active Application Filing
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101756168A (zh) * | 2008-12-25 | 2010-06-30 | 中国科学院兰州化学物理研究所 | 金盏花黄色素的提取方法 |
| CN102190646A (zh) * | 2011-03-29 | 2011-09-21 | 中国农业大学 | 一种高纯度槲皮万寿菊素制备方法 |
| CN102516335A (zh) * | 2011-12-08 | 2012-06-27 | 中国农业大学 | 一种从万寿菊残渣中提取黄酮类化合物的方法 |
| CN105693676A (zh) * | 2014-11-28 | 2016-06-22 | 天津耀宇生物技术有限公司 | 从万寿菊中分离纯化槲皮万寿菊素的方法 |
| CN105541775A (zh) * | 2016-02-26 | 2016-05-04 | 中国农业大学 | 一种槲皮万寿菊素工业化制备方法 |
| CN109232346A (zh) * | 2018-10-12 | 2019-01-18 | 晨光生物科技集团股份有限公司 | 一种叶黄素和万寿菊黄酮的工业化制备方法 |
| CN109498614A (zh) * | 2018-11-29 | 2019-03-22 | 扬州大学 | 猫眼草黄素及青蒿素工业废弃物丙酮层的新用途 |
Non-Patent Citations (9)
| Title |
|---|
| DING, ZHOU ET AL.: "Isolation and Structure Identification of Patuletin and Quercetagetin", ACADEMIC JOURNAL OF GUANGZHOU MEDICAL COLLEGE, vol. 18, no. 1,, 31 December 1990 (1990-12-31), DOI: 20200807141727X * |
| LI FENGWEI ET AL.: "Optimization of Extraction Technology of Lutein from Marigold Flower", HUBEI AGRICULTURAL SCIENCES, vol. 51, no. 18, 30 September 2012 (2012-09-30), DOI: 20200807142007Y * |
| LI, FENGWEI ET AL.: "Optimization of Extraction Technology of Lutein from Marigold Flower", HUBEI AGRICULTURAL SCIENCES, vol. 51, no. 18, 30 September 2012 (2012-09-30), DOI: 20200807141956X * |
| LU, MING ET AL.: "Study on Optimization of Lutin Extraction Processing Parameter in Tagets erecta L.", HORTICULTURE & SEED, no. 1,, 31 December 2011 (2011-12-31), DOI: 20200807141416X * |
| LU, MING ET AL.: "Study on Optimization of Lutin Extraction Processing Parameter in Tagets erecta L.", HORTICULTURE & SEED, no. 1,, 31 December 2011 (2011-12-31), DOI: 20200807141420X * |
| NIU, GUILING ET AL.: "Extraction and Stability of Xanthophyll from Marigold", JOURNAL OF CHENGDE PETROLEUM COLLEGE, vol. 7, no. 4,, 31 December 2005 (2005-12-31), DOI: 20200807141541X * |
| NIU, GUILING ET AL.: "Extraction and Stability of Xanthophyll from Marigold", JOURNAL OF CHENGDE PETROLEUM COLLEGE, vol. 7, no. 4,, 31 December 2005 (2005-12-31), DOI: 20200807141544X * |
| SONG, HAO ET AL.: "Lutein Extraction from Tagete", CHEMICAL ENGINEERING DESIGN, vol. 13, no. 4,, 31 December 2003 (2003-12-31), DOI: 20200807141828X * |
| SONG, HAO ET AL.: "Lutein Extraction from Tagete", CHEMICAL ENGINEERING DESIGN, vol. 13, no. 4,, 31 December 2003 (2003-12-31), DOI: 20200807141842Y * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110372554A (zh) | 2019-10-25 |
| CN110372554B (zh) | 2021-04-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2020259565A1 (zh) | 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 | |
| WO2021077926A1 (zh) | 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 | |
| CN109232346B (zh) | 一种叶黄素和万寿菊黄酮的工业化制备方法 | |
| CN110776449B (zh) | 一种提取叶黄素和槲皮万寿菊素的工业化方法 | |
| CN110003071B (zh) | 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 | |
| CN110105257B (zh) | 一种同步提取叶黄素和槲皮万寿菊素的工业化方法 | |
| CN109394811B (zh) | 一种工业化提取万寿菊黄酮的方法及其万寿菊黄酮 | |
| JP5036210B2 (ja) | ケンフェロール−３−ｏ−ラムノシドを主成分とするポリフェノール含有物の製造方法 | |
| CN110746275A (zh) | 一种利用连续色谱***分离***二酚的方法 | |
| CN113773184B (zh) | 一种姜黄素类化合物的提取方法 | |
| CN108586306B (zh) | 一种采用离子液体强化萃取分离叶黄素和玉米黄质的方法 | |
| CN108047016B (zh) | 一种从姜黄中提取双脱甲氧基姜黄素的方法 | |
| CN108059628A (zh) | 一种蓝莓花青素的快速制备方法 | |
| CN109400658B (zh) | 从油橄榄叶中同步分离纯化橄榄苦苷和羟基酪醇的方法 | |
| CN101322693B (zh) | 一种红花黄色素注射剂及其制备工艺 | |
| CN107382943B (zh) | 一种亚临界水萃取高粱麸皮中二氢槲皮素的方法 | |
| CN112999252B (zh) | 一种连续提取高含量万寿菊黄酮的工业化方法 | |
| CN113801003B (zh) | 一种***二酚的工业化提取方法 | |
| CN103131533A (zh) | 一种超临界co2萃取、精馏、过滤提取薏苡仁油的方法 | |
| CN114380666B (zh) | 一种***二酚的工业化提取方法 | |
| CN115260005B (zh) | 一种纯化提取***二酚的方法与应用 | |
| CN106631666A (zh) | 一种黑番茄中番茄红素的提取精制方法 | |
| WO2022138915A1 (ja) | 精製ロズマリン酸含有組成物の製造方法 | |
| CN107098838A (zh) | 一种大蒜阿霍烯对照品的制备方法 | |
| CN108395420B (zh) | 一种羟基红花黄色素a的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 20831546 Country of ref document: EP Kind code of ref document: A1 |
|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 20831546 Country of ref document: EP Kind code of ref document: A1 |