CN101333229A - Process for extracting phospholipid rich-containing eicosapentaenoic acid and docosahexenoic acid - Google Patents
Process for extracting phospholipid rich-containing eicosapentaenoic acid and docosahexenoic acid Download PDFInfo
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- CN101333229A CN101333229A CNA2008100162231A CN200810016223A CN101333229A CN 101333229 A CN101333229 A CN 101333229A CN A2008100162231 A CNA2008100162231 A CN A2008100162231A CN 200810016223 A CN200810016223 A CN 200810016223A CN 101333229 A CN101333229 A CN 101333229A
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Abstract
A method for extracting a phospholipid rich in eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) is characterized in that firstly marine animal materials are grinded into homogenate solution with colloid; the homogenate solution is frozen and dried and then crushed through a crushing mill; neutral fat and cholesterol in the material powder are removed through supercritical carbon dioxide; and then the phospholipid is extracted with ethanol aqueous solution. The product extracted through the method has high yield and purity; the extraction process has no pollution to the environment and the production staff; the extracted product can promote growth and development of infant brain, enhance memory, promote infant optic nerve and retina development and prevent and cure heart vascular diseases, and has anti-inflammatory, anti-cancer, immunity-enhancing and other physical activities, thereby having higher development and utilization value as health care products or raw materials of medicine.
Description
Technical field
The present invention relates to a kind of method that is rich in timnodonic acid and docosahexenoic acid phosphatide of from the marine animal raw material, extracting.
Background technology
Phosphatide is the important composition composition of cytolemma, as widespread uses in medicine, makeup, foodstuffs industry such as liposome, emulsifying agents.The character of the physiologically active of phosphatide and the composition of its lipid acid and polarity end is closely related, and some phosphatide with ad hoc structure have very high pharmaceutical use.Phosphatide is one of cytolemma main component, still be the form of stocking of numerous informational molecule precursors simultaneously on cytolemma, important effect is arranged in the regulation and control of physical function, has the multiple nutrients nourishing function: regulate body metabolism, enhancing physical efficiency, brain tonic, benefit brain, eliminate brain fag, improve human body memory; Can reduce blood of human body cholesterol, regulating blood fat, prevent atherosclerosis; Can protect the human liver, prevent and treat fatty liver; Can prevent and treat gallbladdergallstonecholetithiasis, senile osteoporosis, Keshan disease; Also have the fitness to human body, the function of being healthy and strong.
The production of phosphatide mainly is to extract from soybean and yolk both at home and abroad at present, limit by raw material natural acid compositing characteristic, can not obtain to be rich in the phosphatide of timnodonic acid (EPA) and docosahexenoic acid (DHA).About using supercritical carbon dioxide extraction to remove neutral fat and cholesterol in the marine animal raw material powder, utilize aqueous ethanolic solution to extract the document that is rich in EPA and DHA phosphatide again, Shang Weijian has report.
Summary of the invention
The purpose of this invention is to provide a kind of ovum with marine animal, sexual gland etc. is raw material, and efficient, environmental protection, safety, the extracting method capable of being industrialized of EPA and DHA phosphatide is rich in acquisition in large quantities, to remedy the above-mentioned deficiency of prior art.
The method of EPA and DHA phosphatide is rich in a kind of extraction, it is characterized in that earlier the marine animal raw material being made homogenate with colloidal mill, with the lyophilize of gained homogenate, after with pulverizer the gained solid substance being pulverized again, utilize supercritical co to slough neutral fat and cholesterol in this raw material powder, extract with aqueous ethanolic solution then.
The product yield height that the present invention extracts, purity is higher, the leaching process environmentally safe, to producers' toxicological harmless, have promote that infant's brain grows, physiologically actives such as hypermnesis, promotion infant optic nerve and retinal development, prevention and treatment cardiovascular disorder, anti-inflammatory, anticancer, strengthening immunity.Studies show that, the phosphatide ratio that is combined with EPA and DHA does not have better cytolemma penetrance in conjunction with the phosphatide of EPA and DHA, stronger anti-tumor activity and more effective immunoloregulation function, thereby have higher value of exploiting and utilizing as healthcare products or medical material.
Description of drawings
Fig. 1 is high performance liquid phase-light scattering detector (HPLC-ELSD) color atlas by the phosphatide of cod roe extraction.
Fig. 2 is the HPLC-ELSD color atlas by the phosphatide of sea grape extraction.
Fig. 3 is the HPLC-ELSD color atlas by the phosphatide of sea urchin gonad extraction.
Fig. 4 is the HPLC-ELSD color atlas by the phosphatide of scallop ovary extraction.
Fig. 5 is the HPLC-ELSD color atlas by the phosphatide of scallop spermary extraction.Among Fig. 1 to Fig. 5, PE is a phosphatidylethanolamine, and PI is a phosphatidylinositols, and PS is a phosphatidylserine, and PC is a phosphatldylcholine, and SM is a sphingophospholipid.
Fig. 6 is gas-chromatography-flame ionic detector (GC-FID) color atlas by the phosphatide of cod roe extraction.
Fig. 7 is the GC-FID color atlas by the phosphatide of sea grape extraction.
Fig. 8 is the GC-FID color atlas by the phosphatide of sea urchin gonad extraction.
Fig. 9 is the GC-FID color atlas by the phosphatide of scallop ovary extraction.
Figure 10 is the GC-FID color atlas by the phosphatide of scallop spermary extraction.
Embodiment
Take from and wash clean cod roe, remove impurity, add after the water of 4 times of weight, make homogenate, after the gained homogenate is pulverized through the 12h vacuum lyophilization, with pulverizer with colloidal mill, obtaining water content is 4.0% (weight percentage, cod roe powder down together) is got in the extraction kettle of its 100g input supercritical carbon dioxide extraction apparatus neutral fat and cholesterol in supercritical carbon dioxide extraction and secondary separation removal ovum powder, pressure in the extraction kettle is 30MPa, and temperature is 60 ℃; First step separating pressure is 8MPa, and separation temperature is 45 ℃; Second stage separating pressure is 6MPa, separation temperature is 35 ℃, the flow of carbonic acid gas is 50ml/g, the extraction time is 6h, from extraction kettle, take out and slough the cod roe powder of neutral fat and cholesterol, 90% aqueous ethanolic solution that adds 15 times of weight extracts, and extracts 30 ℃ of temperature, extracts 10 hours after-filtration and obtains extracting solution, this extracting solution underpressure distillation is obtained solid substance 10.3g, be and be rich in EPA and DHA phospholipid prod, wherein phospholipids content is 88.5%, and wherein PE accounts for 13.4%, PI accounts for 10.2%, PC accounts for 76.4%, and EPA accounted for 11.1% during lipid acid was formed, and DHA accounts for 24.0%.With after the above-mentioned phospholipid prod vacuum packaging in-20 ℃ of preservations.
Embodiment 2
Take from and wash clean squid ovum, remove impurity, add after the water of 6 times of weight, make homogenate with colloidal mill, after the gained homogenate is pulverized through the 24h vacuum lyophilization, with pulverizer, obtain water content and be 5.0% squid ovum powder, get in the extraction kettle of its 200g input supercritical carbon dioxide extraction apparatus, neutral fat and cholesterol in supercritical carbon dioxide extraction and secondary separation removal ovum powder, the pressure in the extraction kettle is 30MPa, temperature is 45 ℃; First step separating pressure is 13MPa, and separation temperature is 45 ℃; Second stage separating pressure is 8MPa, separation temperature is 40 ℃, the flow of carbonic acid gas is 100ml/g, the extraction time is 8h, takes out from extraction kettle and sloughs the squid ovum powder of neutral fat and cholesterol, and 95% aqueous ethanolic solution that adds 12 times of weight extracts, extract 35 ℃ of temperature, extract after 20 hours, filter and obtain extracting solution, this extracting solution underpressure distillation is obtained solid substance 30.6g, be and be rich in EPA and DHA phospholipid prod, phospholipids content is 85.6%, and wherein PE accounts for 18.7%, and PC accounts for 69.0%, SM accounts for 12.3%, EPA accounted for 10.1% during lipid acid was formed, and DHA accounts for 32.1%, with after the above-mentioned phospholipid prod vacuum packaging in-20 ℃ of preservations.
Take from and wash clean sea urchin gonad, remove impurity, add after the water of 5 times of weight, make homogenate with colloidal mill, after the gained homogenate is pulverized through the 16h vacuum lyophilization, with pulverizer, obtain water content and be 4.5% sea urchin gonad powder, get in the extraction kettle of its 250g input supercritical carbon dioxide extraction apparatus, neutral fat and cholesterol in supercritical carbon dioxide extraction and secondary separation removal sea urchin gonad powder, the pressure in the extraction kettle is 25MPa, temperature is 55 ℃; First step separating pressure is 13.5MPa, and separation temperature is 50 ℃; Second stage separating pressure is 9MPa, separation temperature is 45 ℃, the flow of carbonic acid gas is 150ml/g, the extraction time is 10h, takes out from extraction kettle and sloughs the sea urchin gonad powder of neutral fat and cholesterol, and 85% aqueous ethanolic solution that adds 16 times of weight extracts, extract 35 ℃ of temperature, extract after 20 hours, filter and obtain extracting solution, this extracting solution underpressure distillation is obtained solid substance 19.1g, be and be rich in EPA and DHA phospholipid prod, phospholipids content is 87.7%, and wherein PE accounts for 16.3%, and PI accounts for 29.7%, PS accounts for 3.1%, PC accounts for 50.9%, and EPA accounted for 15.6% during lipid acid was formed, and DHA accounts for 2.2%.With after the above-mentioned phospholipid prod vacuum packaging in-20 ℃ of preservations.
Embodiment 4
Take from and wash clean scallop ovary, remove impurity, add after the water of 4.5 times of weight, make homogenate with colloidal mill, after the gained homogenate is pulverized through the 32h vacuum lyophilization, with pulverizer, obtain water content and be 5.0% scallop ovary powder, get in the extraction kettle of its 200g input supercritical carbon dioxide extraction apparatus, neutral fat and cholesterol in supercritical carbon dioxide extraction and secondary separation removal scallop ovary powder, the pressure in the extraction kettle is 20MPa, temperature is 60 ℃; First step separating pressure is 12MPa, and separation temperature is 45 ℃; Second stage separating pressure is 7.5MPa, separation temperature is 45 ℃, the flow of carbonic acid gas is 200ml/g, the extraction time is 15h, takes out from extraction kettle and sloughs the scallop ovary powder of neutral fat and cholesterol, and 75% aqueous ethanolic solution that adds 20 times of weight extracts, extract 35 ℃ of temperature, extract after 15 hours, filter and obtain extracting solution, this extracting solution underpressure distillation is obtained solid substance 11.2g, be and be rich in EPA and DHA phospholipid prod, phospholipids content is 85.7%, and wherein PE accounts for 44.2%, and PI accounts for 10.4%, PS accounts for 2.0%, PC accounts for 43.4%, and EPA accounted for 14.7% during lipid acid was formed, and DHA accounts for 8.6%.With after the above-mentioned phospholipid prod vacuum packaging in-20 ℃ of preservations.
Take from and wash clean scallop spermary, remove impurity, add after the water of 3.5 times of weight, make homogenate with colloidal mill, the gained homogenate obtains water content after 40h vacuum lyophilization, pulverizer are pulverized be 5.0% scallop spermary powder, gets in the extraction kettle that its 200g drops into supercritical carbon dioxide extraction apparatus neutral fat and cholesterol in supercritical carbon dioxide extraction and secondary separation removal scallop spermary powder, pressure in the extraction kettle is 25MPa, and temperature is 55 ℃; First step separating pressure is 12MPa, and separation temperature is 40 ℃; Second stage separating pressure is 7MPa, separation temperature is 40 ℃, the flow of carbonic acid gas is 180ml/g, the extraction time is 18h, takes out from extraction kettle and sloughs the scallop spermary powder of neutral fat and cholesterol, and 75% aqueous ethanolic solution that adds 18 times of weight extracts, extract 45 ℃ of temperature, extract after 12 hours, filter and obtain extracting solution, this extracting solution underpressure distillation is obtained solid substance 26.7g, be and be rich in EPA and DHA phospholipid prod, phospholipids content is 86.3%, and wherein PE accounts for 41.2%, and PI accounts for 17.5%, PS accounts for 1.8%, PC accounts for 39.4%, and EPA accounted for 15.3% during lipid acid was formed, and DHA accounts for 27.3%.With after the above-mentioned phospholipid prod vacuum packaging in-20 ℃ of preservations.
With high performance liquid phase-light scattering detector (HPLC-ELSD) the above-mentioned composition for preparing phosphatide has been carried out qualitative and quantitative analysis, detected the lipid acid of phospholipid prod with gas-chromatography (GC) and formed, detector is flame ionic detector (FID).The gained result as mentioned above.
The supercritical carbon dioxide extraction method that the present invention adopts can be optionally neutral fat and cholesterol being extracted from the marine animal raw material powder, and phosphatide is stayed in the extract remainder because of being insoluble to supercritical co, this method is environmentally friendly, no solvent residue in the product meets the development trend of current green food and green chemical industry.
Marine animal raw material described in the present invention is cod roe, squid ovum, sea urchin gonad, scallop ovary or scallop spermary; Described homogenate is made up of the water of marine animal raw material and 3-6 times of weight; The vacuum lyophilization time of described homogenate is 12-48h; The used aqueous ethanolic solution concentration of described extraction is 65%-95%, and consumption is 2-20 a times of raw material powder weight; When using aqueous ethanolic solution to extract, extracting temperature is 30-60 ℃, and extraction time is 6-20 hour.
Claims (6)
1, the method for timnodonic acid (EPA) and docosahexenoic acid (DHA) phosphatide is rich in a kind of extraction, it is characterized in that earlier the marine animal raw material being made homogenate with colloidal mill, with the lyophilize of gained homogenate, after with pulverizer the gained solid substance being pulverized again, utilize supercritical co to slough neutral fat and cholesterol in this raw material powder, extract with aqueous ethanolic solution then.
2, the method for EPA and DHA phosphatide is rich in extraction according to claim 1, it is characterized in that described marine animal raw material is cod roe, squid ovum, sea urchin gonad, scallop ovary or scallop spermary.
3, the method for EPA and DHA phosphatide is rich in extraction according to claim 1, it is characterized in that described homogenate is made up of the water of marine animal raw material and 3-6 times of weight.
4, the method for EPA and DHA phosphatide is rich in extraction according to claim 1, and the vacuum lyophilization time that it is characterized in that described homogenate is 12-48h.
5, the method for EPA and DHA phosphatide is rich in extraction according to claim 1, it is characterized in that the used aqueous ethanolic solution concentration of described extraction is 65%-95%, and consumption is 2-20 a times of raw material powder weight.
6, the method for EPA and DHA phosphatide is rich in extraction according to claim 1, and when it is characterized in that using aqueous ethanolic solution to extract, extracting temperature is 30-60 ℃, and extraction time is 6-20 hour.
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101812087A (en) * | 2010-05-07 | 2010-08-25 | 青岛海恩赐生物工程有限公司 | Method for extracting high-purity phospholipid from sleeve-fish-processing waste |
| CN101701229B (en) * | 2009-11-17 | 2012-08-29 | 广州海莎生物科技有限公司 | Method for preparing texture phospholipid and lecithin |
| CN104388188A (en) * | 2014-11-10 | 2015-03-04 | 大连工业大学 | Method for extracting triglyceride-type Antarctic krill oil and Antarctic krill phospholipid |
| CN104473162A (en) * | 2014-11-27 | 2015-04-01 | 威海博宇食品有限公司 | Composition for promoting brain development |
| CN104543324A (en) * | 2015-01-27 | 2015-04-29 | 福建农林大学 | Comprehensive utilization method of large yellow croaker roes |
| CN104962590A (en) * | 2015-08-05 | 2015-10-07 | 嘉必优生物工程（武汉）有限公司 | Microbe-derived phospholipid polyunsaturated fatty acid oil and preparation method thereof |
| CN104962589A (en) * | 2015-08-05 | 2015-10-07 | 嘉必优生物工程（武汉）有限公司 | Microbial oil rich in phospholipid type polyunsaturated fatty acid and preparation method thereof |
| CN105601666A (en) * | 2016-01-12 | 2016-05-25 | 武汉轻工大学 | Method for extracting phospholipid from heads of hypophthalmichthys molitrix and product of method |
| CN106632459A (en) * | 2016-12-13 | 2017-05-10 | 山东省科学院生物研究所 | Method for preparing high-purity marine polyunsaturated fatty acid phospholipid by virtue of codfish viscera |
| US10617702B2 (en) | 2009-10-29 | 2020-04-14 | Acasti Pharma Inc. | Concentrated therapeutic phospholipid compositions |
| CN113801157A (en) * | 2021-11-08 | 2021-12-17 | 广东丸美生物技术股份有限公司 | Marine-derived lecithin and preparation method thereof |
| BE1029135B1 (en) * | 2021-08-25 | 2022-09-14 | First Inst Oceanography Mnr | Process for the separation and purification of active ingredients in sea urchins and its application |
| CN115463140A (en) * | 2022-09-27 | 2022-12-13 | 山东省科学院生物研究所 | Application of marine-derived phospholipid in preparation of medicine for preventing liver injury caused by tripterygium glycosides |
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2008
- 2008-05-10 CN CNA2008100162231A patent/CN101333229A/en active Pending
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10617702B2 (en) | 2009-10-29 | 2020-04-14 | Acasti Pharma Inc. | Concentrated therapeutic phospholipid compositions |
| CN101701229B (en) * | 2009-11-17 | 2012-08-29 | 广州海莎生物科技有限公司 | Method for preparing texture phospholipid and lecithin |
| CN101812087A (en) * | 2010-05-07 | 2010-08-25 | 青岛海恩赐生物工程有限公司 | Method for extracting high-purity phospholipid from sleeve-fish-processing waste |
| CN104388188A (en) * | 2014-11-10 | 2015-03-04 | 大连工业大学 | Method for extracting triglyceride-type Antarctic krill oil and Antarctic krill phospholipid |
| CN104388188B (en) * | 2014-11-10 | 2017-04-12 | 大连工业大学 | Method for extracting triglyceride-type Antarctic krill oil and Antarctic krill phospholipid |
| CN104473162A (en) * | 2014-11-27 | 2015-04-01 | 威海博宇食品有限公司 | Composition for promoting brain development |
| CN104543324A (en) * | 2015-01-27 | 2015-04-29 | 福建农林大学 | Comprehensive utilization method of large yellow croaker roes |
| CN106434777A (en) * | 2015-08-05 | 2017-02-22 | 嘉必优生物技术（武汉）股份有限公司 | Polyunsaturated phospholipid fatty acid grease from microorganisms |
| CN104962589A (en) * | 2015-08-05 | 2015-10-07 | 嘉必优生物工程（武汉）有限公司 | Microbial oil rich in phospholipid type polyunsaturated fatty acid and preparation method thereof |
| CN104962590B (en) * | 2015-08-05 | 2018-08-17 | 嘉必优生物技术（武汉）股份有限公司 | A kind of microbe-derived phosphatide type polyunsaturated fatty acid grease and preparation method |
| CN104962589B (en) * | 2015-08-05 | 2019-02-26 | 嘉必优生物技术（武汉）股份有限公司 | A kind of microbial oil and preparation method rich in phosphatide type polyunsaturated fatty acid |
| CN104962590A (en) * | 2015-08-05 | 2015-10-07 | 嘉必优生物工程（武汉）有限公司 | Microbe-derived phospholipid polyunsaturated fatty acid oil and preparation method thereof |
| CN105601666A (en) * | 2016-01-12 | 2016-05-25 | 武汉轻工大学 | Method for extracting phospholipid from heads of hypophthalmichthys molitrix and product of method |
| CN106632459A (en) * | 2016-12-13 | 2017-05-10 | 山东省科学院生物研究所 | Method for preparing high-purity marine polyunsaturated fatty acid phospholipid by virtue of codfish viscera |
| CN106632459B (en) * | 2016-12-13 | 2018-06-01 | 山东省科学院生物研究所 | The method that high-purity marine products polyunsaturated fatty acid phosphatide is prepared using gadus internal organ |
| BE1029135B1 (en) * | 2021-08-25 | 2022-09-14 | First Inst Oceanography Mnr | Process for the separation and purification of active ingredients in sea urchins and its application |
| CN113801157A (en) * | 2021-11-08 | 2021-12-17 | 广东丸美生物技术股份有限公司 | Marine-derived lecithin and preparation method thereof |
| CN115463140A (en) * | 2022-09-27 | 2022-12-13 | 山东省科学院生物研究所 | Application of marine-derived phospholipid in preparation of medicine for preventing liver injury caused by tripterygium glycosides |
| CN115463140B (en) * | 2022-09-27 | 2023-11-24 | 山东省科学院生物研究所 | Application of marine source phospholipid in preparation of medicine for preventing liver injury caused by tripterygium glycosides |
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