CN112661768A - New plant raw material for preparing sesamin and method thereof - Google Patents
New plant raw material for preparing sesamin and method thereof Download PDFInfo
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- CN112661768A CN112661768A CN202110107728.4A CN202110107728A CN112661768A CN 112661768 A CN112661768 A CN 112661768A CN 202110107728 A CN202110107728 A CN 202110107728A CN 112661768 A CN112661768 A CN 112661768A
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Abstract
The invention provides a novel plant raw material rich in sesamin and a novel extraction method. The new plant source raw material of sesamin is prepared by directly distilling Cinnamomum camphora leaf branch or fruit or root or stem or their mixture or their water vapor to extract essential oil residue as raw material; the high-purity sesamin is obtained by crushing the plant body, refluxing and extracting by ethyl acetate, eluting by a silica gel column, purifying by macroporous adsorption resin and recrystallizing. The process has the advantages of simple operation, low cost, safety and stability, yield range of 0.143-0.236% and purity of more than 92.3%.
Description
Technical Field
The invention relates to a new plant raw material rich in sesamin and a new extraction method.
Background
Sesamin, English name sesamin, white needle crystal with molecular formula C20H18O7Molecular weight 370, bis-tetrahydrofuranA pyranolignan compound. The component is used as a pesticide synergist in the early stage, and subsequent large amount of literature researches show that the component has good anti-tumor, anti-inflammatory, antibacterial and other effects, becomes an additive of a plurality of foods and health-care products, and has very high market application value.
Literature studies have shown that sesamin production is mainly achieved by the plant sesame. However, sesame is a valuable oil crop in our country. According to statistics, the total yield of the sesame is only 80 ten thousand tons in 2001, although the sesame is increased every year, the sesame oil production is not enough; after the sesame or the sesame oil is used for extracting sesamin components, the value of the oil is obviously reduced; the byproduct after oil extraction is used for extraction, and the yield is less than 0.1 percent. The industrial production of sesamin requires searching for new raw materials.
Extracting sesamin with sesame oil by Liuyuan method, treating with ethanol to obtain crude product, and purifying with acetone-isopropanol as solvent to obtain 0.24% sesamin with purity of 94%; the plum teaching agent and the like use different solvents for 2 times of crystallization to obtain pure products, and the yield reaches 0.15%. However, these methods are limited to obtaining sesamin from sesame oil, and cannot be applied to other sesamin-rich plants. ZL201410619527.2 adopts a high-pressure device to extract sesame, and a double-water-phase system consisting of polyethylene glycol, sodium hydroxide and water is purified to obtain sesamin, while the high polymer-salt double-water-phase system has high cost, low industrialization degree, difficult later stage desalination and more supporting facilities; ZL201510079590.6 adopts high-speed counter-current chromatography for purification, and has the defects of poor stability and repeatability, expensive equipment and small treatment capacity, so that the industrial production cannot be realized. Therefore, the preparation process of sesamin needs to be optimized.
Cinnamomum camphora recorded in Chinese plant recordC. longepaniculatumCinnamomum camphora (L.) PreslC. camphoraTwo major groups are Lauraceae (Lauraceae) Lauraria (Lauraceae)Cinnamomum) A plant; wherein the linalool essential oil is called as linaloolC. camphora var. LinalooliferaCinnamomum camphora (L.) Presl)C. longepaniculatumMainly used for producing essential oil with high content of eucalyptol, which is mainly distributed in areas such as Fujian, Taiwan, Jiangxi, Guangdong, Yunnan, Guizhou, Sichuan and the like in China, and the artificial forest reaches ten thousand hectares and biomassIs large. Before, the method is only used for producing essential oil, a large number of twigs and leaves are extracted and then are used as waste for treatment, other valuable products are not produced, and the plant utilization rate is low. The development of new products with high additional value is beneficial to reducing the cost of the camphor essential oil, improving the competitiveness of the camphor essential oil extraction industry and promoting the sustainable operation of the industry.
Disclosure of Invention
The invention aims to provide a plant raw material rich in sesamin, the plant raw material is rich, a new raw material source is provided for the industrial production of the sesamin, and simultaneously, a low-cost, safe and stable sesamin extraction production method is provided in a matching way.
The technical method provided by the invention comprises the following steps:
the team of the inventor is dedicated to the development of camphor resources, sesamin and derivatives thereof are separated from camphor leaves, and the content of the sesamin and the derivatives thereof is determined by adopting a high performance liquid chromatography, the content range of the sesamin and the derivatives thereof is between 0.18 and 0.31 percent and is equivalent to the content of sesames, but the cost of the sesames is obviously lower than that of sesames no matter fresh camphor branch and leaf raw materials are applied or waste branch and leaf raw materials after essential oil is extracted by direct distillation, and the sesames and the derivatives thereof have development value. The group of the inventor further develops the high-quality sesamin raw material, optimizes the extraction process and invents a novel extraction preparation method.
A new plant source material for preparing sesamin is prepared from dried plant of Cinnamomum camphora (L.) Presl including Cinnamomum camphora (L.) Presl recorded in Chinese plantC. longepaniculatumCinnamomum camphora (L.) PreslC. camphoraDrying and crushing the raw materials, performing ethyl acetate reflux extraction, performing silica gel column elution, purifying by macroporous adsorption resin, and recrystallizing to obtain the high-purity sesamin.
The above new plant source raw material for preparing sesamin is prepared from dried branches and leaves or fruits or roots or stems of Cinnamomum camphora or their mixture, wherein the leaves are the preferred raw material, and the tree species is Cinnamomum camphoraC. camphora var. linalooliferaIs preferably tree material.
In the novel plant source raw material for preparing the sesamin, the cinnamomum camphora variety is prepared from the approved cinnamomum camphora variety: the 'Nanan No. 1' (the good variety number: Min S-SC-CC-029-.
The novel plant source raw material for preparing sesamin takes waste plant bodies obtained by directly distilling cinnamomum camphora to extract essential oil as a raw material.
A method for extracting sesamin from dry branches and leaves or fruits of cinnamomum camphora or a mixture of branches and leaves and fruits comprises the steps of drying and crushing raw materials, sieving the raw materials with a 20-mesh sieve for later use, crushing, performing reflux extraction by ethyl acetate, concentrating extract liquor to obtain extractum, performing chromatographic elution by a silica gel column, concentrating eluent to obtain extractum, performing chromatographic purification by a macroporous adsorption resin column, concentrating eluent and recrystallizing to obtain a sesamin monomer compound with the purity of more than 95%.
The specific steps are as follows:
drying the raw materials, namely taking the cinnamomum camphora branches, leaves or fruits or a mixture of the branches, leaves and fruits, drying at 70-75 ℃, crushing and sieving with a 20-mesh sieve for later use;
ethyl acetate reflux extraction and concentration: selecting ethyl acetate as extraction solvent, collecting Cinnamomum camphora branch and leaf powder 10 k g, adding ethyl acetate 40-60L, reflux extracting for 2 hr, and filtering to obtain extractive solution; adding 40-60L ethyl acetate solution into the filter residue, reflux extracting for 1 hr, and filtering to obtain extractive solution; mixing the two ethyl acetate extracts, and concentrating under reduced pressure to obtain extract;
silica gel column chromatography elution: further purifying the ethyl acetate extract by silica gel column chromatography, and selecting a petroleum ether-ethyl acetate system; eluting with petroleum ether-ethyl acetate at a ratio of 10:1 for 3-4 column volumes to remove impurities; then eluting 3-5 column volumes by using petroleum ether-ethyl acetate at a ratio of 5:1, collecting the eluent, recovering the solvent under reduced pressure, and concentrating to obtain the high-concentration sesamin extract.
And (3) macroporous adsorption resin column chromatography purification: mixing the high-concentration sesamin extract with adsorption resin with equal mass; the elution solvent system is ethanol-water; eluting with 50-55% of eluting solvent, 3-5 column volumes, and removing impurities; then eluting 4-6 column volumes with 70-80% of eluting solvent, collecting the eluate to obtain 70-80% ethanol eluate of macroporous adsorbent resin. The macroporous adsorbent resin is preferably PRP-512A and PRP-512B, and is further selected from HP-100 and AB-8.
Concentrating, crystallizing and filtering the eluent: recovering solvent from the concentrated solution under reduced pressure to 100-.
By adopting the new material and the extraction method thereof provided by the invention, a large amount of sesamin can be obtained by taking each organ of the cinnamomum camphora plant body as a material or a mixture thereof as a material or taking the plant body obtained after the direct steam distillation extraction of essential oil as a raw material, the sesamin is prepared by the method, the yield range is 0.143-0.236%, and the purity is more than 92.3%.
Detailed Description
The invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the specific material ratios, process conditions and results thereof described in the examples are illustrative only and should not be taken as limiting the invention as detailed in the claims.
Example 1
Taking the cinnamomum camphora leaves 'Nanan No. 1', naturally drying, crushing, and sieving with a 20-mesh sieve; weighing 10 kg of powder, adding 80L of ethyl acetate, reflux-extracting for 2 hours, and filtering to obtain an extracting solution; adding 80L ethyl acetate into the filter residue, reflux extracting for 1 hr, and filtering to obtain extractive solution; mixing the two extractive solutions, recovering solvent under reduced pressure, and concentrating to dry to obtain 358 g of ethyl acetate extract; mixing the extract with 365 g of 60-100-mesh silica gel, loading 2.5 kg of 200-mesh silica gel into a column by a dry method, and eluting by 2.4L of petroleum ether-ethyl acetate 10:1 to remove impurities; eluting with 3L of petroleum ether-ethyl acetate 5:1, collecting eluate, and recovering solvent under reduced pressure to obtain high-concentration sesamin extract 20.5 g; dissolving the extract with ethyl acetate, mixing with 20.5 g PRP-512A macroporous adsorbent resin, eluting with PRP-512A macroporous adsorbent resin column chromatography, eluting with 55% ethanol solution for 1L to remove impurities, eluting with 1.5L 75% ethanol solution, collecting eluate, recovering solvent to 500 mL under reduced pressure, naturally cooling, standing, precipitating white needle crystal, and vacuum filtering to obtain 23.60 g sesamin with yield of 0.236% and purity of 93.8%.
Example 2
Taking the cinnamomum camphora fruits of MD1 or MD2, naturally drying, crushing and sieving by a 20-mesh sieve for later use; the other steps are the same as example 1, and 18.84 g of sesamin is obtained, the yield is 0.188%, and the purity is 92.3%o
Example 3
The mixture of the branches and leaves of the cinnamomum camphora ' nan ' an No. 1 ' and the fruits is naturally dried, crushed and sieved by a 20-mesh sieve for later use, and other step parameters are the same as the parameters in the example 1, so that 16.29 g of sesamin is obtained, the yield is 0.163%, and the purity is 93.5%.
Example 4
Naturally drying the current-year branches and leaves of the ' nan ' an No. 1 ' cinnamomum camphora, crushing, and sieving with a 20-mesh sieve for later use; the other process parameters were the same as in example 1, and 14.3 g of sesamin was obtained with a yield of 0.143% and a purity of 95.4%.
Example 5
Drying and pulverizing the roots of "MD 1" or "MD 2" Cinnamomum camphora, sieving with 20 mesh sieve, and performing the same procedures as in example 1 to obtain sesamin 15.1g, yield 0.151%, and purity 94.5%.
Example 6
The stems or stems of the cinnamomum camphora ' nan ' an No. 1 ' are naturally dried, crushed and sieved by a 20-mesh sieve for later use, and the parameters of other steps are the same as those of the example 1, so that 14.8g of sesamin is obtained, the yield is 0.148%, and the purity is 92.9%.
Example 7
The aerial parts of the harvested cinnamomum camphora are naturally dried, crushed and sieved by a 20-mesh sieve for later use, and the parameters of other steps are the same as those of the example 1, so that 17.3g of sesamin is obtained, the yield is 0.173%, and the purity is 94.3%.
Example 8
The cinnamomum camphora plant body of Nanan No. 1 is harvested from the root of Nelumbo Nucifera Gaertn, naturally dried, crushed and sieved by a sieve of 20 meshes for later use, and the parameters of other steps are the same as the parameters in the example 1, so that 16.5g of sesamin is obtained, the yield is 0.165 percent and the purity is 92.5 percent.
Example 8
The waste plant body obtained by extracting the essential oil from the cinnamomum camphora ' nan ' No. 1 ' by direct steam distillation is taken as a raw material, the raw material is naturally dried and crushed, and the raw material is sieved by a 20-mesh sieve for later use, and the other steps are the same as the step 1, so that 14.6g of sesamin is obtained, the yield is 0.146%, and the purity is 93.1%.
Example 9
With Cinnamomum camphoraC. longepaniculatumThe branches and leaves are taken as raw materials, are naturally dried and crushed, and are sieved by a 20-mesh sieve for standby, and the parameters of other steps are the same as those of the example 1, so that 20.6g of sesamin is obtained, the yield is 20.6%, and the purity is 93.1%.
Example 10
With Cinnamomum camphoraC. longepaniculatumThe root is taken as a raw material, naturally dried, crushed and sieved by a 20-mesh sieve for standby, and the other parameters of the steps are the same as those of the example 1, so that 21.6g of sesamin is obtained, the yield is 21.6 percent, and the purity is 93.1 percent.
Claims (4)
1. A plant-derived new raw material for preparing sesamin is characterized in that dry plant bodies of cinnamomum camphora are used as raw materials, and the cinnamomum camphora comprises cinnamomum camphora recorded in Chinese plantC. longepaniculatumCinnamomum camphora (L.) PreslC. camphoraDrying and crushing the raw materials, performing ethyl acetate reflux extraction, performing silica gel column elution, purifying by macroporous adsorption resin, and recrystallizing to obtain the high-purity sesamin.
2. The novel plant-derived raw material for preparing sesamin according to claim 1, which is characterized in that dried branches and leaves or fruits or roots or stems of cinnamomum camphora or a mixture thereof is used as a raw material, wherein leaves are a preferred raw material; the cinnamomum camphora is planted in the treeC. camphora var. linalooliferaFor the optimized tree seed material, the cinnamomum camphora variety takes the approved improved variety Nanan No. 1, MD1 and MD2 of Fujian province as the optimized improved variety material.
3. The novel plant-derived raw material for producing sesamin according to claim 1, wherein the raw material is waste plant obtained by direct steam distillation of cinnamomum camphora to extract essential oil.
4. A new method for preparing sesamin is characterized in that dried branches, leaves, fruits, roots, stems or a mixture thereof of cinnamomum camphora are taken as raw materials, crushed and sieved by a 20-mesh sieve, and ethyl acetate is refluxed and extracted, silica gel column elution, macroporous adsorption resin purification and recrystallization are carried out to obtain high-purity sesamin monomer components, and the main steps comprise:
drying and crushing raw materials: taking branches and leaves or fruits of cinnamomum camphora or a mixture of branches and leaves and fruits, drying at 70-75 ℃, crushing and sieving with a 20-mesh sieve for later use;
ethyl acetate reflux extraction and concentration: selecting ethyl acetate as extraction solvent, collecting linaloe plant powder 10 k g, adding ethyl acetate 40-60L, reflux extracting for 2 hr, and filtering to obtain extractive solution; adding 40-60L ethyl acetate solution into the filter residue, reflux extracting for 1 hr, and filtering to obtain extractive solution; mixing the two ethyl acetate extracts, and concentrating under reduced pressure to obtain extract;
silica gel column chromatography elution: further purifying the ethyl acetate extract by silica gel column chromatography, and selecting a petroleum ether-ethyl acetate system; eluting with petroleum ether-ethyl acetate at a ratio of 10:1 for 3-4 column volumes to remove impurities; eluting 3-5 column volumes by using petroleum ether-ethyl acetate at a ratio of 5:1, collecting eluent, recovering the solvent under reduced pressure, and concentrating to obtain high-concentration sesamin extract;
mixing the high-concentration sesamin extract with adsorption resin with equal mass; the elution solvent system is ethanol-water; eluting with 50-55% of eluting solvent, 3-5 column volumes, and removing impurities; then eluting 4-6 column volumes with 70% -80% of eluting solvent, collecting the eluate to obtain 70% -80% ethanol eluate of macroporous adsorbent resin;
recovering solvent from the concentrated solution under reduced pressure to 200-300 mL, standing at normal temperature, naturally cooling, separating out white needle crystal, and filtering to obtain sesamin.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115575551A (en) * | 2022-09-20 | 2023-01-06 | 贵州中医药大学 | Detection method of rhizoma bletillae, preparation method of rhizoma bletillae control extract and application of rhizoma bletillae control extract |
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2021
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115575551A (en) * | 2022-09-20 | 2023-01-06 | 贵州中医药大学 | Detection method of rhizoma bletillae, preparation method of rhizoma bletillae control extract and application of rhizoma bletillae control extract |
| CN115575551B (en) * | 2022-09-20 | 2023-09-26 | 贵州中医药大学 | Bletilla striata detection method |
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Application publication date: 20210416 |