CN101709030B - Method for extracting and separating ginkgo leaf polyprenol acetic ester from ginkgo leaf by supercritical carbon oxide - Google Patents
Method for extracting and separating ginkgo leaf polyprenol acetic ester from ginkgo leaf by supercritical carbon oxide Download PDFInfo
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Abstract
The invention discloses a method for extracting and separating ginkgo leaf polyprenol acetic ester from a ginkgo leaf by supercritical carbon oxide. The first extraction comprises the following steps of: putting dried and pulverized ginkgo leaf powder into an extraction kettle, introducing the supercritical carbon oxide with the pressure of 25-35 MPa into the extraction kettle; controlling the temperature of the extraction kettle to 40-70 DEG C; circularly extracting the ginkgo leaf for 5-10 hours; and releasing an ointment containing the ginkgo leaf polyprenol acetic ester from a separation kettle in two-stage series connection. The second extraction comprises the following steps of: filling the ointment which is obtained in the first extraction into the extraction kettle; introducing the supercritical carbon oxide with the pressure of 5-15MPa into the extraction kettle; controlling the temperature of the extraction kettle to 20-30 DEG C; circularly extracting the ginkgo leaf for 3-8 hours; and releasing an oily matter of the ginkgo leaf polyprenol acetic ester from the extraction kettle. The method has low cost and high content without organic solvent extraction, and the extract with high purity can be used as an important material applied to healthcare food, cosmetics, drugs and the like.
Description
Technical field
The present invention relates to a kind of method that adopts supercritical co twice extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf.
Background technology
Ginkgo is called as " living fossil ", is one of distinctive ancient seeds of China.Contain abundant polypenthylene alcohol ester, flavonoid, terpene lactones isoreactivity composition in the Ginkgo Leaf, these materials have very strong pharmacological action to aplastic anemia, various hepatic diseases, mellitus, cental system disease etc.
Polyprenol acetic ester in the Ginkgo Leaf belongs to birch polyprenol acetic ester; Mainly form by 14-20 isopentene group unit; Have the long-chain compound that 2 trans-isopentene groups, a 11-17 cis isopentene group and α-acetoxyl group form, account for 80% of polyprenol constituents total content in the Ginkgo Leaf.The polyprenol acetic ester can become polyprenol through hydrolysis; Polyprenol can change dolichol into through self cellular metabolism in artificial chemosynthesis or the animal body again, and dolichol has the human body of improvement hemopoietic function and significantly effects such as treatment aplastic anemia, hepatic diseases, mellitus.Therefore, Ginkgo Leaf polyprenol acetic ester is the precursor substance of effective natural drug, has the important pharmaceutical use of potential.
Chinese patent (ZL01113696.0) report use multiple lipotropy organic solvent soaking and extracting, silicagel column separate preparation polyprenol acetic ester, again through hydrolysis or saponification reaction, the silicagel column separating impurity prepares polyprenol.Chinese patent (ZL200410074088.8) report uses multiple lipotropy organic solvent soaking and extracting preparation to contain the crude extract of polyprenol acetic ester, obtain the polyprenol crude extract through the basic hydrolysis saponification, removes impurity with supercritical extraction again and prepares polyprenol.These two kinds of technologies have all been used solvent extraction when preparation polyprenol acetic ester, have following shortcoming: the residual of (1) solvent might bring toxic side effect; (2) toxic ingredient in the Ginkgo Leaf such as the ginkgoic acid of severe toxicity, can cause quality product to descend with the effective active substance of human body is extracted; (3) leaching process uses low boiling point solvents such as sherwood oil and normal hexane in a large number, and big and difficult recovery of consumption is caused environmental pollution; (4) the product yield is low, and cost is high, is difficult to realize suitability for industrialized production.
Summary of the invention
The present invention proposes that a kind of cost is low, yield is high, need not the method for employing supercritical co twice extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf of organic solvent; The Ginkgo Leaf polyprenol acetic ester that obtains both can be used as raw material and directly had been used for products such as protective foods, makeup, also can be used to make the polyprenol medicine.
The present invention adopts the method for supercritical co twice extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf, may further comprise the steps:
(1) extraction for the first time: drying and the ginkgo leaf powder pulverized are packed in the extraction kettle; Start the CO 2 high pressure pump, in extraction kettle, feeding pressure is the supercritical co of 25-35 MPa, and control extraction kettle temperature is 40-70 ℃; Cycling extraction 5-10 hour; The ginkgo leaf powder extract remainder is emitted in termination of pumping, step-down from extraction kettle, from the separating still of two-stage series connection, discharge the ointment that contains Ginkgo Leaf polyprenol acetic ester; The temperature of first step separating still is that 30-50 ℃, pressure are the 5-10 MPa, and second stage separating still temperature is that 20-40 ℃, pressure are the 3-8 MPa;
(2) extraction for the second time: the ointment that contains Ginkgo Leaf polyprenol acetic ester that extraction for the first time discharges is packed in the extraction kettle; In extraction kettle, feeding pressure is the supercritical co of 5-15 MPa; Control extraction kettle temperature is 20-30 ℃, after cycling extraction 3-8 hour, and termination of pumping, step-down; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter; From separating still, emit impurity, the temperature of first step separating still is that 20-30 ℃, pressure are the 2-3 MPa, and second stage separating still temperature is that 15-20 ℃, pressure are the 1-5 MPa.
Be preferably, the extraction kettle temperature is 65 ℃ when extracting for the first time, and extracting pressure is 25 MPas, and the cycling extraction time is 6 hours, and first step separating still temperature is that 40 ℃, pressure are 5 MPas, and second stage separating still temperature is that 30 ℃, pressure are 3 MPas; The extraction kettle temperature is 25 ℃ when extracting for the second time, and extracting pressure is 10 MPas, and the cycling extraction time is 7 hours, and the temperature of first step separating still is that 30 ℃, pressure are 3 MPas, and second stage separating still temperature is that 20 ℃, pressure are 2 MPas.
The present invention adopts the technique effect of twice extracting process acquisition to be:
(1) the present invention utilizes and can will hang down polar material and strong polar material direct separation under the lower temperature of supercritical co, and no organic reagent is residual, has saved precipitation and the technology that reclaims organic solvent, the carbonic acid gas recycle, and cost is lower; Have high selectivity, can accomplish distillation and extraction process simultaneously; Extraction for the first time finishes and adopts the low-temp low-pressure extraction second time to remove impurity, further separates the Ginkgo Leaf polyprenol acetate content and the purity height that obtain, for industries such as food, medicine, makeup provide " green pure natural raw material ";
(2) the present invention utilizes the carbonic acid gas good solubility to have removed in the Ginkgo Leaf raw material deleterious ginkgoic acid and leaf wax, lipid acid, volatilization wet goods impurity through twice extraction, has shortened the production cycle, has improved production efficiency;
(3) the present invention has adopted higher extracting pressure and extraction temperature when extracting for the first time, and utilizing higher fluid density to make yield is the crude extract ointment that contains the polyprenol acetic ester more than 5%, but the content of polyprenol acetic ester is lower; The relative molecular weight that utilizes the polyprenol acetic ester when extracting for the second time big (greater than 900) is difficult by the above-critical state carbon dioxide abstraction; After adopting lower extracting pressure and extraction temperature to remove low molecular weight impurities the polyprenol acetic ester is carried out purifying; Obtained yield and be 0.5% above purity greater than 80% Ginkgo Leaf polyprenol acetic ester oily matter; Dna purity is high, has actual application value;
(4) the Ginkgo Leaf polyprenol acetic ester and the human body dolichol ester structure of the present invention's preparation are similar; The polyterpene alcohol ester has various biological functions such as differentiation of the human hematopoietic stem of promotion and treatment aplastic anemia; The Ginkgo Leaf polypenthylene alcohol ester that uses method provided by the invention to prepare changes the raw material that the polyterpene alcohol ester provides the pure natural high biological activity into as chemosynthesis or human body self metabolism, has the important pharmaceutical use of potential.
Embodiment
Embodiments of the invention are provided below, but the present invention not merely is defined in these embodiment.
Embodiment 1
Adopting the method for supercritical co extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf, at first, is that 10 kilograms of ginkgo leaf powders of 60 purposes are packed in the extraction kettle with grinding particle size; Start the CO 2 high pressure pump, boost to 30 MPas, supercritical co is sent in the extraction kettle; The extraction kettle temperature is 65 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, the temperature of first step separating still is that 40 ℃, pressure are 5 MPas, and the temperature of second stage separating still is 30 ℃, pressure 3 MPas; CO 2 fluid is again through freezing, collapsing back in the gas holder; Carbon dioxide flow be the 0.3-1.2 cubic meter/hour, cycling extraction is after 6 hours, termination of pumping, step-down; From extraction kettle, emit the Ginkgo Leaf extract remainder, from separating still, emit about 950 grams of the ointment that contains Ginkgo Leaf polyprenol acetic ester;
Then, the ointment that contains Ginkgo Leaf polyprenol acetic ester that coming together is first packed in the extraction kettle, starts the CO 2 high pressure pump; Boost to 10 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 25 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, 20 ℃ of the temperature of first step separating still, pressure are 2 MPas, and the temperature of second stage separating still is 20 ℃, pressure 1 MPa; Carbonic acid gas is again through freezing, collapsing back in the gas holder; Behind the cycling extraction 7 hours, the impurity such as wax, lipid acid and sterol in the ointment are emitted in termination of pumping, step-down from separating still; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter 88 grams, wherein the polyprenol acetate content is 84.01%.
Embodiment 2
At first, be that 20 kilograms of ginkgo leaf powders of 80 purposes are packed in the extraction kettle with grinding particle size, start the CO 2 high pressure pump; Boost to 25 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 60 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, the temperature of first step separating still is that 30 ℃, pressure are 5 MPas, and the temperature of second stage separating still is 30 ℃, pressure 4 MPas; CO 2 fluid is again through freezing, collapsing back in the gas holder; Carbon dioxide flow be the 0.3-1.2 cubic meter/hour, cycling extraction is after 10 hours, termination of pumping, step-down; From extraction kettle, emit the Ginkgo Leaf extract remainder, from separating still, emit about 1700 grams of the ointment that contains Ginkgo Leaf polyprenol acetic ester;
Then, the ointment that contains Ginkgo Leaf polyprenol acetic ester that coming together is first packed in the extraction kettle, starts the CO 2 high pressure pump; Boost to 10 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 25 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, 25 ℃ of the temperature of first step separating still, pressure are 3 MPas, and the temperature of second stage separating still is 20 ℃, pressure 3 MPas; Carbonic acid gas is again through freezing, collapsing back in the gas holder; Behind the cycling extraction 5 hours, the impurity such as wax, lipid acid and sterol in the ointment are emitted in termination of pumping, step-down from separating still; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter 174 grams, wherein the polyprenol acetate content is 81.39%.
Embodiment 3
At first, be that 15 kilograms of ginkgo leaf powders of 100 purposes are packed in the extraction kettle with grinding particle size, start the CO 2 high pressure pump; Boost to 30 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 55 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, the temperature of first step separating still is that 35 ℃, pressure are 5 MPas, and the temperature of second stage separating still is 30 ℃, pressure 4 MPas; CO 2 fluid is again through freezing, collapsing back in the gas holder; Carbon dioxide flow be the 0.3-1.2 cubic meter/hour, cycling extraction is after 8 hours, termination of pumping, step-down; From extraction kettle, emit the Ginkgo Leaf extract remainder, from separating still, emit about 1360 grams of the ointment that contains Ginkgo Leaf polyprenol acetic ester;
Then, the ointment that contains Ginkgo Leaf polyprenol acetic ester that coming together is first packed in the extraction kettle, starts the CO 2 high pressure pump; Boost to 10 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 30 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, 20 ℃ of the temperature of first step separating still, pressure are 3 MPas, and the temperature of second stage separating still is 20 ℃, pressure 1 MPa; Carbonic acid gas is again through freezing, collapsing back in the gas holder; Behind the cycling extraction 7 hours, the impurity such as wax, lipid acid and sterol in the ointment are emitted in termination of pumping, step-down from separating still; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter 129 grams, wherein the polyprenol acetate content is 83.09%.
Embodiment 4
At first, be that 12 kilograms of ginkgo leaf powders of 60 purposes are packed in the extraction kettle with grinding particle size, start the CO 2 high pressure pump; Boost to 35 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 45 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, the temperature of first step separating still is that 35 ℃, pressure are 10 MPas, and the temperature of second stage separating still is 30 ℃, pressure 8 MPas; CO 2 fluid is again through freezing, collapsing back in the gas holder; Carbon dioxide flow be the 0.3-1.2 cubic meter/hour, cycling extraction is after 8 hours, termination of pumping, step-down; From extraction kettle, emit the Ginkgo Leaf extract remainder, from separating still, emit about 1020 grams of the ointment that contains Ginkgo Leaf polyprenol acetic ester;
Then, the ointment that contains Ginkgo Leaf polyprenol acetic ester that coming together is first packed in the extraction kettle, starts the CO 2 high pressure pump; Boost to 5 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 30 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, 25 ℃ of the temperature of first step separating still, pressure are 3 MPas, and the temperature of second stage separating still is 20 ℃, pressure 1 MPa; Carbonic acid gas is again through freezing, collapsing back in the gas holder; Behind the cycling extraction 8 hours, the impurity such as wax, lipid acid and sterol in the ointment are emitted in termination of pumping, step-down from separating still; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter 91 grams, wherein the polyprenol acetate content is 83.09%.
Embodiment 5
At first, be that 18 kilograms of ginkgo leaf powders of 80 purposes are packed in the extraction kettle with grinding particle size, start the CO 2 high pressure pump; Boost to 35 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 40 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, the temperature of first step separating still is that 50 ℃, pressure are 10 MPas, and the temperature of second stage separating still is 40 ℃, pressure 8 MPas; CO 2 fluid is again through freezing, collapsing back in the gas holder; Carbon dioxide flow be the 0.3-1.2 cubic meter/hour, cycling extraction is after 5 hours, termination of pumping, step-down; From extraction kettle, emit the Ginkgo Leaf extract remainder, from separating still, emit about 1420 grams of the ointment that contains Ginkgo Leaf polyprenol acetic ester;
Then, the ointment that contains Ginkgo Leaf polyprenol acetic ester that coming together is first packed in the extraction kettle, starts the CO 2 high pressure pump; Boost to 15 MPas, supercritical co is sent in the extraction kettle, the extraction kettle temperature is 28 ℃; Get in one-level, two placed in-line separating stills of secondary through the CO 2 fluid behind the extraction kettle, 25 ℃ of the temperature of first step separating still, pressure are 2 MPas, and the temperature of second stage separating still is 15 ℃, pressure 2 MPas; Carbonic acid gas is again through freezing, collapsing back in the gas holder; Behind the cycling extraction 8 hours, the impurity such as wax, lipid acid and sterol in the ointment are emitted in termination of pumping, step-down from separating still; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter 109 grams, wherein the polyprenol acetate content is 82.11%.Check and analysis: the content that adopts above-mentioned 5 the embodiment gained polyprenol acetic ester of rp-hplc determination
U.S. Waters performance liquid chromatography (HPLC) system: Waters 1525 HPPs, Waters 2487UV detector.Polyprenol acetic ester reference substance is provided by Department Of Medicine, Peking University pharmaceutical college natural drug chamber.
Chromatographic condition: chromatographic column PLATISIL ODS C18 (250mm * 4.6mm, 5 μ m), moving phase: Virahol-methyl alcohol (55: 45, V/V), flow velocity 1.0mL/min, 25 ℃ of column temperatures detect wavelength 210nm.
Analytical procedure: precision takes by weighing polyprenol acetic ester reference substance and uses normal hexane to be mixed with the solution of concentration as 0.5mg/L, 5mg/L, 10mg/L, 20mg/L, 40mg/L, 80mg/L; Automatic sampling is analyzed; (A is a peak area to obtain regression equation A=20379c+84882; C is a concentration), r=0.9995.Precision takes by weighing each 1 in the polyprenol acetic ester sample of 5 extraction preparations, is mixed with the solution that concentration is 40mg/L respectively, and automatic sampling is also measured the result each 3 times, calculates by regression equation, obtains the result and sees table 1:
Table 1 polyprenol acetate content is measured the result
Learn through above-mentioned analyzing and testing: the polyprenol acetate content for preparing according to method of the present invention is more than 80%, and extract purity is high, explains that technology of the present invention has applications well and is worth.
Claims (3)
1. the method for supercritical co extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf may further comprise the steps:
(1) extraction for the first time: drying and the ginkgo leaf powder pulverized are packed in the extraction kettle, and the Ginkgo Leaf grinding particle size is the 45-150 order, starts the CO 2 high pressure pump; In extraction kettle, feeding pressure is the supercritical co of 25-35 MPa; Control extraction kettle temperature is 40-70 ℃, cycling extraction 5-10 hour, and termination of pumping, step-down; From extraction kettle, emit the ginkgo leaf powder extract remainder; From the separating still of two-stage series connection, discharge the ointment that contains Ginkgo Leaf polyprenol acetic ester, the temperature of first step separating still is that 30-50 ℃, pressure are the 5-10 MPa, and second stage separating still temperature is that 20-40 ℃, pressure are the 3-8 MPa;
(2) extraction for the second time: the ointment that contains Ginkgo Leaf polyprenol acetic ester that extraction for the first time discharges is packed in the extraction kettle; In extraction kettle, feeding pressure is the supercritical co of 5-15 MPa; Control extraction kettle temperature is 20-30 ℃, after cycling extraction 3-8 hour, and termination of pumping, step-down; From extraction kettle, emit Ginkgo Leaf polyprenol acetic ester oily matter; From separating still, emit impurity, the temperature of first step separating still is that 20-30 ℃, pressure are the 2-3 MPa, and second stage separating still temperature is that 15-20 ℃, pressure are the 1-5 MPa.
2. the method for supercritical co according to claim 1 extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf; It is characterized in that: the extraction kettle temperature is 65 ℃ when extracting for the first time; Extracting pressure is 25 MPas; The cycling extraction time is 6 hours, and first step separating still temperature is that 40 ℃, pressure are 5 MPas, and second stage separating still temperature is that 30 ℃, pressure are 3 MPas.
3. the method for supercritical co according to claim 1 extracting and separating Ginkgo Leaf polyprenol acetic ester from Ginkgo Leaf; It is characterized in that: the extraction kettle temperature is 25 ℃ when extracting for the second time; Extracting pressure is 10 MPas; The cycling extraction time is 7 hours, and the temperature of first step separating still is that 30 ℃, pressure are 3 MPas, and second stage separating still temperature is that 20 ℃, pressure are 2 MPas.
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| CN102603483B (en) * | 2012-03-13 | 2015-07-22 | 江苏大学 | Method for extracting polyprenols from ginkgo leaves |
| CN102766673A (en) * | 2012-07-26 | 2012-11-07 | 中国林业科学研究院林产化学工业研究所 | Synthetic method of (R)-4-benzyloxy-2-methyl-1-butyl alcohol in dolichol biological chain |
| CN103083368B (en) * | 2013-02-05 | 2015-07-15 | 中国林业科学研究院林产化学工业研究所 | Preparation method of ginkgo leaf lipoid components having antibacterial activities |
| CN106810619B (en) * | 2015-12-02 | 2019-01-15 | 中国科学院大连化学物理研究所 | A kind of gingko episperm pectin and polypentenol extracting method |
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| CN1392167A (en) * | 2001-06-18 | 2003-01-22 | 中国林业科学研究院林产化学工业研究所 | Preparing process and use of ginkgo leaf polypentenol and ginkgo leaf extract |
| CN1628696A (en) * | 2004-09-03 | 2005-06-22 | 张平 | Pharmaceutical composition containing ginkgo leaf poly pentenol and its preparing method |
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| CN1392167A (en) * | 2001-06-18 | 2003-01-22 | 中国林业科学研究院林产化学工业研究所 | Preparing process and use of ginkgo leaf polypentenol and ginkgo leaf extract |
| CN1628696A (en) * | 2004-09-03 | 2005-06-22 | 张平 | Pharmaceutical composition containing ginkgo leaf poly pentenol and its preparing method |
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