CN112299997A - Method for separating and extracting chain ester compounds from Nigella sativa seeds - Google Patents
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Abstract
The invention relates to a slaveNigella sativaThe method for separating and extracting the chain ester compounds from the seeds comprises the following steps: 1) dryingNigella sativaPulverizing seeds, defatting with petroleum ether, extracting with 60-80% ethanol, and recovering solvent under reduced pressure to obtain extract; 2) dissolving the extract with methanol, mixing with silica gel column, and gradient eluting with dichloromethane-methanol to obtain 7 components Fr1-Fr 7; 3) the component Fr1 is subjected to silica gel column chromatography under normal pressure to obtain 6 components Fr 1-1-Fr 1-6; 4) separating the Fr1-4 component by gel column chromatography and silica gel column chromatography to obtain 9-decenoic acid-12-hydroxyethyl ester; separating the fraction Fr1-2 by gel column chromatography, silica gel column chromatography, and reverse phase chromatography to obtain 9-undecylenic acid-1- (3-pentaenoic acid)Oxysilyl) -ethyl ester. The invention has simple extraction process, easy product obtaining, recyclable solvent, large extraction amount and industrialized production.
Description
Technical Field
The invention belongs to the technical field of plant extraction and separation, and particularly relates to a method for effectively and quickly separating and extracting chain ester compounds (such as 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxy silyl) -ethyl ester and the like) from Nigella sativa seeds.
Background
The seeds of Nigella sativa are dried seeds of Nigella sativa of black grass of Ranunculaceae, are native to southwestern Asia and widely distributed in Mediterranean, Central Europe, and Western Asia; the seed oil is widely used as edible oil in Egypt areas such as middle east and North Africa countries, and is also used for health food to resist diseases, and is widely applied to food. The main components of Nigella sativa seeds comprise flavone, saponin, alkaloid, steroid, phenol and the like, and in addition, a large amount of grease is contained. The seeds of Nigella sativa have various pharmacological actions, including antibacterial, antioxidant, anticancer, antiinflammatory, blood sugar lowering, liver protecting, and diuretic effects.
At present, there is no method for extracting and separating chain ester compounds (such as 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester, etc.) from seeds of Nigella sativa.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for simply, effectively and quickly separating and extracting chain ester compounds (such as 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester and the like) from Nigella sativa seeds.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for separating and extracting chain ester compounds from Nigella sativa seeds comprises the following steps:
1) taking dried seeds of Nigella sativa as raw materials, crushing, degreasing with petroleum ether, volatilizing the petroleum ether from residues, extracting with 60-80% ethanol, and recovering solvent from the extracting solution under reduced pressure to obtain extract;
2) dissolving the extract with methanol, mixing with silica gel column, performing gradient elution with dichloromethane-methanol at volume ratio of 20:1, 15:1, 10:1, 5:1, 3:1, 1:1, detecting by silica gel thin layer chromatography, and mixing to obtain 7 components, wherein the obtained components have polarity from small to large and are labeled as Fr1-Fr 7;
3) mixing the 1 st component Fr1 with 100-200 mesh silica gel, then loading on a column (normal pressure silica gel column chromatography), performing gradient elution by petroleum ether-ethyl acetate with the volume ratio of 30:1, 20:1, 15:1, 10:1, 5:1 and 2:1, detecting and combining by silica gel thin layer chromatography to obtain 6 components, and sequentially marking the components as Fr 1-1-Fr 1-6 from small to large according to the polarity of the obtained components;
4) subjecting the component Fr1-4 to Sephadex LH-20 Sephadex column chromatography, eluting with dichloromethane-methanol at a volume ratio of 1:1, detecting and combining by silica gel thin layer chromatography to obtain 2 components, sequentially marking the obtained components as 1-4-1 and 1-4-2 according to the polarity from small to large, subjecting the component 1-4-1 to silica gel column chromatography, and subjecting the component 1-4-1 to gradient elution with petroleum ether-ethyl acetate at a volume ratio of 30:1, 20:1, 15:1, 10:1, 5:1 and 1:1 to obtain 9-decenoic acid-12-hydroxyethyl ester (English name: 9-octadienoic-acid-12-hydroxy-ethyl ester) crude product;
the component Fr1-2 is chromatographed by Sephadex LH-20 Sephadex column, eluting with dichloromethane-methanol at volume ratio of 1:1, detecting with silica gel thin layer chromatography, mixing to obtain 2 components, sequentially marking the obtained components as 1-2-1 and 1-2-2 according to the polarity of the components from small to large, separating the component 1-2-1 by silica gel column chromatography, gradient eluting with petroleum ether-ethyl acetate at volume ratio of 15:1, 10:1, 5:1, 1:1, separating by reverse phase chromatography, gradient eluting with methanol-water solution at volume ratio of 70:30, 80:20, 100:0 to obtain crude 9-undecylenic acid-1- (3-pentoxysilyl) -ethyl ester (English name: 9-acyclic acid-11- (3-pentyloxy) -ethyl ester).
Further, in order to obtain better purity, in the step 4), the crude 9-decenoic acid-12-hydroxyethyl ester is dissolved by methanol, purified by Sephadex LH-20 Sephadex column chromatography, and eluted by methanol to obtain a pure product.
Further, in order to obtain better purity, in the step 4), the crude 9-undecylenic acid-1- (3-pentoxysilyl) -ethyl ester is dissolved by methanol, and is subjected to Sephadex LH-20 Sephadex column chromatography and isocratic elution by methanol-water (namely 60% methanol aqueous solution) in a volume ratio of 60:40 to obtain a pure product.
Specifically, in the step 1), degreasing with petroleum ether is performed for 2-4 times, each degreasing time is 2-4 days, and the adding ratio of the dried Nigella sativa seeds to the petroleum ether feed liquid is 5 kg: 6-10L.
Specifically, in the step 1), the extract is extracted by cold soaking with 70% ethanol for 3 times, and each time lasts for 3 days; the adding ratio of the residue to the feed liquid of 70% ethanol is 5 kg: 6-10L.
The invention relates to a 9-octadienoic-acid-12-hydroxy-ethyl ester, which has a molecular formula: c20H38O3Molecular weight: 326 having the formula:
the invention relates to a 9-acyclic acid-11- (3-pentyloxicanyl) -ethyl ester, the molecular formula is as follows: c20H36O3And, molecular weight: 324, having a structural formula as shown below, wherein the numbers identified in the structural formula are consistent with the carbon numbers marked in the subsequent map experiment results:
at present, there is no report on the extraction and separation of chain ester compounds (such as 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester, etc.) from seeds of Nigella sativa. The invention quickly and effectively extracts and separates the chain ester compounds (such as 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester and the like) contained in the seeds of the Nigella sativa by degreasing petroleum ether of the seeds of the Nigella sativa, separating 60-80% ethanol extract and separating the chain ester compounds by means of silica gel column chromatography, reverse phase column chromatography, gel column chromatography and the like. Compared with the prior art, the invention has the following beneficial effects:
1) up to now, no reports have been made on the production of chain ester compounds (e.g., 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester) from seeds of the plant Nigella sativa. The invention provides a method for extracting and separating the compounds from seeds of Nigella sativa, which is favorable for better developing and utilizing medicinal plants of the seeds of Nigella sativa and sustainable utilization of the plants.
2) The chain ester compounds (such as 9-decenoic acid-12-hydroxyethyl ester, 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester and the like) obtained by extraction and separation have wide biological activity, and the invention provides an extraction and separation method of the compounds, which is convenient for carrying out deep research on the compounds. The invention has simple extraction process, easy product obtaining, recyclable solvent, large extraction amount and industrialized production.
3) The separation material used in the invention has reversed phase, silica gel and gel column chromatography, is insoluble in water and any solvent, has no toxicity and odor, stable chemical property, better selectivity to organic matters, is not influenced by inorganic salts and strong ion low molecular compounds, is easy to elute and regenerate, and is beneficial to multiple utilization. The separation of preparative high-performance liquid phase used in the purification process is the most popular novel separation method at present, time and labor are saved, and the yield of samples can be greatly improved.
Drawings
FIG. 1 is a carbon spectrum of 1- (3-pentoxysilyl) -ethyl 9-undecenoate;
FIG. 2 is a hydrogen spectrum of 1- (3-pentoxysilyl) -ethyl 9-undecenoate;
FIG. 3 is a carbon spectrum of 9-decenoic acid-12-hydroxyethyl ester;
FIG. 4 is a hydrogen spectrum of 9-decenoic acid-12-hydroxyethyl ester.
Detailed Description
In order to make the technical purpose, technical solutions and advantages of the present invention clearer, the technical solutions of the present invention are further described with reference to specific examples, which are intended to explain the present invention and are not to be construed as limiting the present invention, and those who do not specify a specific technique or condition in the examples follow the techniques or conditions described in the literature in the art or follow the product specification.
In the following examples, seeds of Nigella sativa as a raw material were collected from Egyptian; the concentrations of the ethanol and the methanol are volume concentrations.
Example 1
A method for separating and extracting chain ester compounds (9-decenoic acid-12-hydroxyethyl ester and 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester) from Nigella sativa seeds specifically comprises the following steps:
1) the method comprises the following steps of taking 5kg of dried seeds of Nigella sativa as raw materials, crushing, soaking and degreasing with 7L of petroleum ether at room temperature (degreasing is carried out for 3 times, and the degreasing time is 3 days each time), volatilizing the petroleum ether from residues, and cold-soaking and extracting with 70% ethanol at room temperature for 3 times (the adding ratio of the residues to 70% ethanol is 5 kg: 7L), 3 days each time, mixing the extracting solutions, and recovering the solvent under reduced pressure to obtain extract;
2) dissolving the extract with methanol, mixing with silica gel column, gradient eluting silica gel column with dichloromethane-methanol at volume ratio of 20:1, 15:1, 10:1, 5:1, 3:1, 1:1 sequentially, detecting and mixing silica gel thin layer chromatography to obtain 7 components, and sequentially labeling the components from small to large as Fr1-Fr 7;
3) mixing the 1 st component Fr1 with 100-200 mesh silica gel, then loading on a column (normal pressure silica gel column chromatography), performing gradient elution by petroleum ether-ethyl acetate with the volume ratio of 30:1, 20:1, 15:1, 10:1, 5:1 and 2:1, detecting and combining by silica gel thin layer chromatography to obtain 6 components, and sequentially marking the components as Fr 1-1-Fr 1-6 from small to large according to the polarity of the obtained components;
4) subjecting the component Fr1-4 to Sephadex LH-20 Sephadex column chromatography, eluting with dichloromethane-methanol at a volume ratio of 1:1, detecting and combining by silica gel thin-layer chromatography to obtain 2 components, sequentially labeling 1-4-1 and 1-4-2 according to the polarity of the obtained components from small to large, subjecting the component 1-4-1 to silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate at a volume ratio of 30:1, 20:1, 15:1, 10:1, 5:1 and 1:1 to obtain crude 9-decenoic acid-12-hydroxyethyl ester; dissolving the crude product with methanol, purifying with Sephadex LH-20 Sephadex column chromatography, eluting with methanol to obtain 9-decenoic acid-12-hydroxyethyl ester (English name: 9-octadienoic-acid-12-hydroxy-ethyl ester) pure product;
subjecting the component Fr1-2 to Sephadex LH-20 Sephadex column chromatography, eluting with dichloromethane-methanol at a volume ratio of 1:1, detecting and combining by silica gel thin layer chromatography to obtain 2 components, sequentially labeling 1-2-1 and 1-2-2 according to the polarity of the obtained components from small to large, subjecting the component 1-2-1 to silica gel column chromatography separation, subjecting the component to gradient elution with petroleum ether-ethyl acetate at a volume ratio of 15:1, 10:1, 5:1 and 1:1, subjecting the component to reversed phase chromatography separation, and subjecting the component to gradient elution with methanol-water solution at a volume ratio of 70:30, 80:20 and 100:0 to obtain crude 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester. Dissolving the crude product with methanol, performing Sephadex LH-20 Sephadex column chromatography, and isocratically eluting with methanol-water at volume ratio of 60:40 to obtain pure 9-undecylenic acid-1- (3-pentoxysilyl) -ethyl ester (English name: 9-Undecenoic acid-11- (3-pentyloxyranyl) -ethyl ester).
The obtained pure 9-decenoic acid-12-hydroxyethyl ester (9-octadienoic-acid-12-hydroxy-ethyl ester) is light yellow oily matter, the yield is 0.00010%, and the purity is more than or equal to 99%. The structure of the prepared compound is identified by applying various spectroscopy technologies, and the structure is as follows:
instrument materials: ultraviolet measurement is carried out on a UV-210A ultraviolet spectrum determinator;1H，13the C-NMR spectrum was determined by Bruker am-400MHz NMR spectrometer. TMS is an internal standard; the two-dimensional nuclear magnetic resonance spectrum is measured by a DRX-500MHz nuclear magnetic resonance instrument; mass spectra were determined on a VG.AUTO Spec-3000 type mass spectrometer. The maps are shown in FIGS. 3 and 4, and the specific experimental results are as follows:
ESI-MS m/z:347[M+Na]+the molecular formula is as follows: c20H36O3。1H-NMR(CD3OD,400MHz)δ:5.41(2H,m,H-9,10),4.07(2H,m,H-1′),3.51(1H,m,H-12),2.26(2H,t,H-2),2.16(2H,m,H-11),2.02(2H,m,H-8),1.56(2H,m,H-3),1.43(1H,m,H-13a),1.36(2H,m,H-7),1.35(2H,m,H-6),1.34(1H,m,H-13b),1.29(4H,m,H-4,5),1.27(4H,m,H-16,17),1.28(2H,m,H-14),1.20(3H,t,H-2′),0.87(3H,t,H-18)。13C NMR(101MHz,CD3OD)δ:175.6(C-1),132.6(C-9),126.9(C-10),72.6(C-12),61.4(C-1′),37.7(C-13),36.2(C-11),35.1(C-2),33.1(C-16),30.7(C-14),30.5(C-7),30.3(C-6),30.2(C-4),30.2(C-5),28.4(C-8),26.8(C-15),26.1(C-3),23.7(C-17),14.6(C-2′),14.5(C-18)；
And (4) checking: fluorescence was observed by TLC at UV 254 nm; the sulfuric acid developer develops color and shows purple red at 110 ℃ for 5 minutes.
The purified 9-undecylenic acid-1- (3-pentoxysilyl) -ethyl ester (9-acyclic acid-11- (3-pentyloxyranyl) -ethyl ester) prepared above is a light yellow oil, the yield is 0.00040%, and the purity is more than or equal to 99%. The structure of the prepared compound is identified by applying various spectroscopy technologies, and the structure is as follows:
instrument materials: ultraviolet measurement is carried out on a UV-210A ultraviolet spectrum determinator;1H，13the C-NMR spectrum was determined by Bruker am-400MHz NMR spectrometer. TMS is an internal standard; the two-dimensional nuclear magnetic resonance spectrum is measured by a DRX-500MHz nuclear magnetic resonance instrument; mass spectra were determined on a VG.AUTO Spec-3000 type mass spectrometer. The maps are shown in figures 1 and 2, and the specific experimental results are as follows:
ESI-MS m/z:347[M+Na]+the molecular formula is as follows: c20H36O3。1H-NMR(CD3OD,400MHz)δ:5.49(1H,m,H-9),5.40(1H,m,H-10),4.07(2H,q,J＝7Hz,H-1′),2.91(2H,m,H-12,13),2.28(1H,m,H-11a),2.26(2H,t,J＝7.4,H-2),2.21(1H,m,H-11b),2.03(2H,q,J＝7.0,H-8),1.57(2H,m,H-3),1.49(2H,m,H-15),1.47(1H,m,H-14),1.43(1H,m,H-14),1.33(4H,m,H-7,16),1.32(2H,m,H-17),1.29(6H,m,H-4,5,6),1.20(3H,t,J＝7,H-2′),0.89(3H,t,J＝7,H-18)。13C-NMR(100MHz,CD3OD)δ:175.6(C-1),35.1(C-2),26.0(C-3),30.1(C-4),30.1(C-5),30.2(C-6),30.6(C-7),28.3(C-8),133.5(C-9),125.1(C-10),27.2(C11),57.9(C-12),58.6(C-13),27.3(C-14),28.8(C-15),32.9(C-16),23.7(C-17),61.4(C-1′),14.5(C-2′)；
And (4) checking: fluorescence was observed by TLC at UV 254 nm; the sulfuric acid developer develops color and turns yellow at 110 ℃ for 5 minutes.
Claims (5)
1. FromNigella sativaThe method for separating and extracting the chain ester compounds from the seeds is characterized by comprising the following steps:
1) in the dry stateNigella sativaPulverizing seeds, defatting with petroleum ether, volatilizing petroleum ether from residue, extracting with 60-80% ethanol, and recovering solvent from the extractive solution under reduced pressure to obtain extract;
2) dissolving the extract with methanol, mixing with silica gel column, performing gradient elution with dichloromethane-methanol at volume ratio of 20:1, 15:1, 10:1, 5:1, 3:1, 1:1, detecting by silica gel thin layer chromatography, and mixing to obtain 7 components, wherein the obtained components have polarity from small to large and are labeled as Fr1-Fr 7;
3) mixing the 1 st component Fr1 with 100-200 meshes of silica gel, then loading the mixture into a column, performing gradient elution by using petroleum ether-ethyl acetate with the volume ratio of 30:1, 20:1, 15:1, 10:1, 5:1 and 2:1, detecting and combining by using silica gel thin layer chromatography to obtain 6 components, and sequentially marking the components as Fr 1-1-Fr 1-6 from small to large according to the polarity of the obtained components;
4) subjecting the component Fr1-4 to Sephadex LH-20 Sephadex column chromatography, eluting with dichloromethane-methanol at a volume ratio of 1:1, detecting and combining by silica gel thin-layer chromatography to obtain 2 components, sequentially labeling 1-4-1 and 1-4-2 according to the polarity of the obtained components from small to large, subjecting the component 1-4-1 to silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate at a volume ratio of 30:1, 20:1, 15:1, 10:1, 5:1 and 1:1 to obtain crude 9-decenoic acid-12-hydroxyethyl ester;
subjecting the component Fr1-2 to Sephadex LH-20 Sephadex column chromatography, eluting with dichloromethane-methanol at a volume ratio of 1:1, detecting and combining by silica gel thin layer chromatography to obtain 2 components, sequentially labeling 1-2-1 and 1-2-2 according to the polarity of the obtained components from small to large, subjecting the component 1-2-1 to silica gel column chromatography separation, subjecting the component to gradient elution with petroleum ether-ethyl acetate at a volume ratio of 15:1, 10:1, 5:1 and 1:1, subjecting the component to reversed phase chromatography separation, and subjecting the component to gradient elution with methanol-water solution at a volume ratio of 70:30, 80:20 and 100:0 to obtain crude 9-undecenoic acid-1- (3-pentoxysilyl) -ethyl ester.
2. The method of claim 1, whereinNigella sativaThe method for separating and extracting the chain ester compounds from the seeds is characterized in that in the step 4), the crude product of the 9-decenoic acid-12-hydroxyethyl ester is dissolved by methanol, and is eluted by methanol through Sephadex LH-20 gel column chromatography to obtain a pure product.
3. The method of claim 1, whereinNigella sativaThe method for separating and extracting the chain ester compounds from the seeds is characterized in that in the step 4), the crude product of the 9-undecylenic acid-1- (3-pentoxysilyl) -ethyl ester is dissolved by methanol, and is eluted with methanol-water isocratic according to the volume ratio of 60:40 by Sephadex LH-20 gel column chromatography to obtain a pure product.
4. The method of claim 1, whereinNigella sativaThe method for separating and extracting the chain ester compounds from the seeds is characterized in that in the step 1), petroleum ether is degreased for 2 to 4 times, the degreasing time is 2 to 4 days each time, and the mixture is driedNigella sativaThe adding ratio of the seeds to the petroleum ether is 5 kg: 6-10L.
5. The method of claim 1, whereinNigella sativaThe method for separating and extracting the chain ester compounds from the seeds is characterized in that in the step 1), the seeds are extracted by cold soaking with 70 percent ethanol for 3 times, and each time lasts for 3 days; the adding ratio of the residue to the feed liquid of 70% ethanol is 5 kg: 6-10L.
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| WO2005009332A2 (en) * | 2003-07-31 | 2005-02-03 | Palsamed (P.B.S.) Ltd. | Compositions-of-matter for lowering serum cholesterol and/or triglyceride level and methods of producing and using same |
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| WO2005009332A2 (en) * | 2003-07-31 | 2005-02-03 | Palsamed (P.B.S.) Ltd. | Compositions-of-matter for lowering serum cholesterol and/or triglyceride level and methods of producing and using same |
| CN101318892A (en) * | 2008-07-23 | 2008-12-10 | 张敏 | Method for preparing sebacic acid with ricinus oil compounds |
| CN103517709A (en) * | 2011-05-02 | 2014-01-15 | 梧桐生物技术私人有限公司 | A composition for treating autoimmune disorders and methods thereof |
| CN109912680A (en) * | 2019-04-24 | 2019-06-21 | 中国人民解放军第四军医大学 | A kind of oleanane-type triterpene saponin and its purification methods and uses |
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