CN1431188A - Method for preparing sea squirt fatty acids and methyl ester, ethyl ester, triglyceride and its preparing method as well as application infunctional food and drugs - Google Patents
Method for preparing sea squirt fatty acids and methyl ester, ethyl ester, triglyceride and its preparing method as well as application infunctional food and drugs Download PDFInfo
- Publication number
- CN1431188A CN1431188A CN03111710A CN03111710A CN1431188A CN 1431188 A CN1431188 A CN 1431188A CN 03111710 A CN03111710 A CN 03111710A CN 03111710 A CN03111710 A CN 03111710A CN 1431188 A CN1431188 A CN 1431188A
- Authority
- CN
- China
- Prior art keywords
- ascidian
- esters
- lipid acid
- sweet
- ethyl ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 125000004494 ethyl ester group Chemical group 0.000 title claims abstract description 33
- 150000004702 methyl esters Chemical class 0.000 title claims abstract description 27
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 235000013305 food Nutrition 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 title abstract description 16
- 229930195729 fatty acid Natural products 0.000 title abstract description 16
- 239000000194 fatty acid Substances 0.000 title abstract description 16
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title abstract description 12
- 150000004665 fatty acids Chemical class 0.000 title abstract description 8
- 229940079593 drug Drugs 0.000 title abstract 2
- 241000251555 Tunicata Species 0.000 title description 2
- 241000251557 Ascidiacea Species 0.000 claims abstract description 109
- 238000011161 development Methods 0.000 claims abstract description 11
- 238000001035 drying Methods 0.000 claims abstract description 6
- 150000002632 lipids Chemical class 0.000 claims description 73
- 239000002253 acid Substances 0.000 claims description 70
- 150000002148 esters Chemical class 0.000 claims description 50
- 235000009508 confectionery Nutrition 0.000 claims description 49
- DVSZKTAMJJTWFG-UHFFFAOYSA-N docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCCC=CC=CC=CC=CC=CC=CC(O)=O DVSZKTAMJJTWFG-UHFFFAOYSA-N 0.000 claims description 25
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims description 25
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 24
- 238000002360 preparation method Methods 0.000 claims description 14
- 238000007670 refining Methods 0.000 claims description 14
- 230000032050 esterification Effects 0.000 claims description 11
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 239000000284 extract Substances 0.000 claims description 11
- 235000019387 fatty acid methyl ester Nutrition 0.000 claims description 10
- 230000002526 effect on cardiovascular system Effects 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 8
- 238000000605 extraction Methods 0.000 claims description 8
- 238000007127 saponification reaction Methods 0.000 claims description 8
- 239000010779 crude oil Substances 0.000 claims description 7
- 238000004332 deodorization Methods 0.000 claims description 7
- 235000013376 functional food Nutrition 0.000 claims description 7
- 238000002203 pretreatment Methods 0.000 claims description 5
- HXWJFEZDFPRLBG-UHFFFAOYSA-N Timnodonic acid Natural products CCCC=CC=CCC=CCC=CCC=CCCCC(O)=O HXWJFEZDFPRLBG-UHFFFAOYSA-N 0.000 claims description 4
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 claims description 4
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 4
- 238000012545 processing Methods 0.000 claims description 3
- 238000000638 solvent extraction Methods 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 239000000287 crude extract Substances 0.000 claims description 2
- 230000006872 improvement Effects 0.000 claims description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims 1
- 210000004369 blood Anatomy 0.000 abstract description 6
- 239000008280 blood Substances 0.000 abstract description 6
- 206010028980 Neoplasm Diseases 0.000 abstract description 5
- 201000001320 Atherosclerosis Diseases 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000010298 pulverizing process Methods 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 210000002569 neuron Anatomy 0.000 abstract 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 25
- 230000000694 effects Effects 0.000 description 17
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000018109 developmental process Effects 0.000 description 9
- 241000282414 Homo sapiens Species 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 108010023302 HDL Cholesterol Proteins 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000021342 arachidonic acid Nutrition 0.000 description 6
- 229940114079 arachidonic acid Drugs 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 235000021323 fish oil Nutrition 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000251569 Ciona Species 0.000 description 5
- 210000001772 blood platelet Anatomy 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 210000002381 plasma Anatomy 0.000 description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000002519 immonomodulatory effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000001737 promoting effect Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000005728 strengthening Methods 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
- 108010028554 LDL Cholesterol Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241000251576 Styela clava Species 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 230000003143 atherosclerotic effect Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000001077 hypotensive effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000007901 soft capsule Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
- BFSPAPKTIGPYOV-BQYQJAHWSA-N (e)-1-[4-(4-hydroxyphenyl)piperazin-1-yl]-3-thiophen-2-ylprop-2-en-1-one Chemical compound C1=CC(O)=CC=C1N1CCN(C(=O)\C=C\C=2SC=CC=2)CC1 BFSPAPKTIGPYOV-BQYQJAHWSA-N 0.000 description 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000251556 Chordata Species 0.000 description 2
- 235000019733 Fish meal Nutrition 0.000 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 2
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000004467 fishmeal Substances 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 108010025964 lipophorin Proteins 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000199 molecular distillation Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 102000057234 Acyl transferases Human genes 0.000 description 1
- 108700016155 Acyl transferases Proteins 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 241000251571 Ciona intestinalis Species 0.000 description 1
- 241000644035 Clava Species 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- 241000282560 Macaca mulatta Species 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- 208000035992 Postmortem Changes Diseases 0.000 description 1
- 208000000418 Premature Cardiac Complexes Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 101000912235 Rebecca salina Acyl-lipid (7-3)-desaturase Proteins 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 101000877236 Siganus canaliculatus Acyl-CoA Delta-4 desaturase Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000009874 alkali refining Methods 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000008131 children development Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- 230000006957 competitive inhibition Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
- 229960001123 epoprostenol Drugs 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002223 garnet Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 210000001308 heart ventricle Anatomy 0.000 description 1
- 210000003677 hemocyte Anatomy 0.000 description 1
- 229940000351 hemocyte Drugs 0.000 description 1
- 235000020256 human milk Nutrition 0.000 description 1
- 210000004251 human milk Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- 210000001595 mastoid Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009401 outcrossing Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 150000003904 phospholipids Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 206010036067 polydipsia Diseases 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- CASUWPDYGGAUQV-UHFFFAOYSA-M potassium;methanol;hydroxide Chemical compound [OH-].[K+].OC CASUWPDYGGAUQV-UHFFFAOYSA-M 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
- 230000029865 regulation of blood pressure Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
A process for preparing the fatty acid of ascidian and its methylester, ethylester and triglyceride from ascidian includes washing fresh ascidian, dripdrying, drying, pulverizing, extracting to obtain the coase triglyceride, degumming, deacidifying, decolouring, deodouring, dewaxing to obtain refined triglyceride, saponifying, acidifying to obtain fatty acid of ascidian, and esterifying to obtain its methylester or ethylester. The said products can reduce blood fat, preventing atherosclerosis and cancers, and promote development of nerve cells, so they can be used to prepare medicines or health-care food.
Description
(1) technical field:
The present invention relates to the series product of Ascidian fatty acid extract, be to make Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters specifically by Ascidian, the invention still further relates to the preparation method of Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters simultaneously and in reducing blood-fat, improve with the treatment cardiovascular and cerebrovascular diseases, prevent curing cancers, regulate and improve the application aspect upgrowth and development of children and anti-inflammatory and the immunomodulatory.
(2) background technology:
Ascidian (Ascidian) is Chordata (chordata); the general name of Urochordata (classAscidiancea) animal; be a kind of marine organisms of extensive distribution; because of its active ingredient has antitumor; antiviral; regulate physiology such as immunity; pharmacological function and being paid close attention to deeply; we find when following the trail of its activeconstituents; fatty acid content is higher in Styela clava (Styel clava) and the Ciona (Ciona intestinalis); be rich in polyunsaturated fatty acid (PUFA) in its fat; especially n-3 polyunsaturated fatty acid; as timnodonic acid (EPA); docosahexenoic acid (DHA); EPA wherein; DHA content is equivalent to fish oil; having the potential exploitation is worth; EPA; DHA is as the major function composition of fish oil; nearly decades have been obtained extensive studies and application; the anti-bolt lipid-reducing function of EPA; the promoting intelligence and strengthening brain function of DHA has obtained widespread usage; but the by product that traditional fish oil is mainly processed from fish meal; fish oil production is limited by fish production and fish meal processing; the over-drastic marine fishing causes the destruction of fishing resources and fish oil resource; make fishing oil industry be faced with the raw material crisis; prospect causes anxiety; although people try hard to open up the new way that a fish oil is produced from little algae is cultivated, and are not effective so far.In China, the Ascidian resource is quite abundant, the Bohai Sea, the Huanghai Sea, the East Sea, the South Sea all have Ascidian to distribute, put down in writing kind and had 66 kinds, Styela clava, Ciona, mastoid process skin Ascidian etc. are sociales, extract Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters and preparation method thereof and the application in functional food and medicine and do not see at present from Ascidian.
(3) goal of the invention:
Purpose of the present invention is intended to overcome the deficiency of above-mentioned prior art, and the Ascidian lipid acid that extracts from Ascidian and methyl esters thereof, ethyl ester, sweet three esters are provided.
Another object of the present invention provides the preparation method of Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters.
Another purpose of the present invention also be to provide Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters in reducing blood-fat, improve with the treatment cardiovascular and cerebrovascular diseases, prevent curing cancers, regulate and improve the application aspect upgrowth and development of children and anti-inflammatory and the immunomodulatory.
In order to achieve the above object, the present invention is achieved in that sweet three esters of Ascidian lipid acid, it be by Ascidian through pre-treatment, extraction, refining, make after the refining classification.
In order to achieve the above object, Ascidian lipid acid of the present invention, be by sweet three esters of above-mentioned Ascidian lipid acid through saponification, acidifying, make after the refining classification.
In order to achieve the above object, Ascidian fatty acid methyl ester of the present invention or ethyl ester, be by above-mentioned Ascidian lipid acid through esterification, make after the refining classification, also can directly carry out esterification by sweet three esters of Ascidian lipid acid, make after the refining classification.
Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three ester series product, its content is in timnodonic acid, docosahexenoic acid weight 〉=10%.
To achieve these goals, the preparation method of Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters comprises following processing step:
A, pre-treatment, with fresh Ascidian clean, drain, dry, pulverize; Drying temperature is lower than 80 degree; That drying comprises is air-dry, oven dry, vacuum-drying, lyophilize.
B, extract, pretreated Ascidian through extract the sweet three ester crude extracts of Ascidian lipid acid, it is crude oil, extraction can be adopted supercritical extraction or solvent extraction, and the solvent that solvent extraction is adopted is other organic solvents such as ethyl acetate, ethanol, acetone, chloroform, propyl carbinol, ether, sherwood oil, normal hexane, hexanaphthene, gasoline or wherein any two kinds, multiple mixed solvent; Crude oil routinely technology through come unstuck, after the depickling, decolouring, deodorization, dewaxing refining sweet three esters of purified Ascidian lipid acid;
C, saponification, acidifying, sweet three esters of the Ascidian lipid acid of above-mentioned steps get Ascidian lipid acid after saponification, acidifying;
D, esterification, the Ascidian lipid acid of above-mentioned steps gets Ascidian fatty acid methyl ester or ethyl ester through esterification, and sweet three esters of the Ascidian lipid acid that also available extraction step obtains directly carry out esterification and get Ascidian fatty acid methyl ester or ethyl ester.
Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters respectively through branch carry, urea bag, overcritical rectifying or classifications such as molecular distillation or vacuum distilling handle, the product of the different various purity of EPA, DHA content.
In order to achieve the above object, Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters can be used for preparing lipid-reducing function food, medicine and related medical health-care product.
In order to achieve the above object, Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters can be used for preparing functional food, medicine and the related medical health-care product that improves with the treatment cardiovascular and cerebrovascular diseases.
In order to achieve the above object, Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters can be used for preparing and regulate and the functional food, medicine and the related medical health-care product that improve upgrowth and development of children.
Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters be used to prepare functional food, medicine and related medical health-care product routinely technology make various formulations, comprise oral liquid, capsule, tablet, granule, electuary, dripping pill, micropill, beverage and injection type.
Ascidian lipid acid of the present invention and methyl esters thereof, ethyl ester, sweet three esters are through gas chromatographic analysis, its n-3 unsaturated fatty acids by weight content greater than 30%, wherein EPA, DHA by weight its content sum greater than 10%.
Compared with the prior art the present invention has marked improvement and positively effect: 1, Ascidian aboundresources; 2, n-3 content of polyunsaturated fatty acid height in the Ascidian lipid acid of the present invention; 3, the extracting method technology of Ascidian lipid acid of the present invention is simple, and facility investment is few, and production process is convenient to control; 4, the Ascidian lipid acid that extracts with method of the present invention can extensively be used in reducing blood-fat, improves and treat cardiovascular and cerebrovascular diseases, anti-curing cancers, regulates and improve upgrowth and development of children and anti-inflammatory and immunomodulatory aspect.
The main active ingredient of Ascidian lipid acid of the present invention is EPA and the DHA in the n-3 polyunsaturated fatty acid, and its main pharmacological is as follows:
People's long term studies is found, the n-3 polyunsaturated fatty acid has the important physical effect in human body, and these unsaturated fatty acidss common feature structurally is, first unsaturated double-bond always is positioned on the tertiary carbon atom of carbochain methyl end, so be referred to as the n-3 polyunsaturated fatty acid, this class unsaturated fatty acids human body Synthesis conversion is extremely low, mainly relies on the picked-up of extraneous food, and wherein tool meaning is timnodonic acid (EPA) and docosahexenoic acid (DHA).
EPA is an important component of keeping the human body normal physiological function, through the TXA of metabolism generation
3And PGI
3, the experiment proved that TXA
3Do not have and impel the platelet aggregation effect, and PGI
3Can suppress thrombocyte assembles on vessel wall.EPA can combine with cyclooxygenase competitively, can suppress to impel the TXA of platelet aggregation
2Synthetic.DHA directly acts on platelet membrane, can suppress arachidonic acid and be converted into PG and TXA
2, can under the effect of enzyme, be converted into EPA.But PUFA preparation anticoagulant is adjusted blood fat, prolongs the clotting time, increases biomembranous liquid state, changes erythrocytic plasticity-, reduces effects such as blood viscous, the control cardiovascular and cerebrovascular diseases is had the effectiveness of protectiveness.Experiment shows, contains the above PUFA preparation of EPA and DHA70% and be the medicine of anticoagulant and blood coagulation resisting function preferably.
DHA content in pallium, cornea, testis and the seminal fluid of human body is very high, and the DHA that early children development needs comes from human milk, and DHA almost all exists with phospholipid form in human body.Can utilize synthetic EPA of linolenic acid and DHA in health adult's body very slowly, but transformation efficiency is very low, baby, diabetic and the elderly then can not carry out this conversion.The shortage of DHA may influence child's intelligence, eyesight and physiological development.
One, adjust blood fat:
1, triglyceride level: the n-3 polyunsaturated fatty acid has stronger specific action to reducing plasma triglyceride (TG) level, and obvious dosage effect dependency arranged, healthy volunteer's day is obeyed 5-10gEPA, can significantly reduce plasma tg, EPA dosage is big more, and the effect that reduces the TG level is remarkable more.Phillipson etc. report 20 routine hyperlipidemia patients, and edible n-3 polyunsaturated fatty acid is after 4 weeks, and it is normal that plasma tg is recovered.Think at present; EPA in the n-3 polyunsaturated fatty acid is not only the inhibitor of fatty acid synthetase; and oxidation of fatty acids decomposed promoter action is arranged; reduce the lipid acid supply that is used for synthetic TG thus; EPA can also suppress the triglyceride acyl transferase activity in the liver cell, makes the synthetic minimizing of TG.
2, total cholesterol: the n-3 polyunsaturated fatty acid is very inconsistent to the effect of total cholesterol, but its effect to total cholesterol is affirmed the TG effect not as it and be obvious.
3, lipophorin: n-3 is many, and saturated fatty acid has dual function to lipophorin, it can reduce the level of low density lipoprotein cholesterol in the blood plasma (LDL-C), as increase n-3 polyunsaturated fatty acid in the food, the people LDL-C level of 30%-40% is reduced.The n-3 polyunsaturated fatty acid can also improve high density lipoprotein cholesterol (HDL-C) level, several compare the result who carries out crossing research with placebo and show, take little or middle dosage n-3 polyunsaturated fatty acid, the HDL-C level 5%-10% that can raise, but heavy dose of n-3 polyunsaturated fatty acid is sex-limited sometimes to the effect of HDL-C, be that short-term is taken the HDL-C level that can raise, long-term large dose oral administration is then to the obviously influence side by side of HDL-C level.
Two, to the effect of cardiovascular and cerebrovascular:
1, to atherosclerotic effect, experimentation on animals confirms, feeds pigs with high lipid food, abrades left anterior descending coronary artery with air bag sometimes, increases the weight of blood vessel injury, causes the experimental atherosclerosis model.As in feed, adding the n-3 polyunsaturated fatty acid for the experimental group animal, every day 30ml, coronary artery operations area minimizing as a result.Prove that it has significant regressive effect to the experimental atherosclerosis pathology.
2, to the effect of platelet aggregation: in being diagnosed as atherosclerotic hyperlipidaemia invalid diet, attach the n-3 polyunsaturated fatty acid after, hematoblastic prolonged survival period.Experiment in vitro proves the TXA on its energy blocking platelet film
2After acceptor, integral experiment are also found to take the n-3 polyunsaturated fatty acid, the TXA that excretes among atherosclerotic and the healthy human urine
2Metabolite significantly reduces.Studies show that the n-3 polyunsaturated fatty acid can with arachidonic acid (AA) competition cyclo-oxygenase, and suppress its activity, make AA generate thromboxane (TXA
2) reduce, it can also increase the generation of prostaglandin(PG) (PG), prostacyclin (PGI), this two classes material and TXA by another approach simultaneously
2Opposite effect is arranged, and the thrombocyte that can suppress to cause behind the blood vessel injury discharges the reaction of ADP, serotonin (5-HT) and catecholamine (CA), thereby suppresses platelet adhesion reaction, gathering, makes cruor time extending.
3, hypotensive effect: hypertension is a kind of multi-factor disease, studies show that, the no hypotensive effect of low dose of many unsaturated lipids of n-3 attitude acid (3g/d), and heavy dose of (9g/d) can make the blood pressure moderate of primary hypertension patient descend, hypotensive effect has dose-dependently.Accepting the patient of renal transplantation, giving the elevation of blood pressure that low dose of n-3 polyunsaturated fatty acid can prevent ciclosporin to cause, and reducing with renal vascular resistance.The step-down mechanism of n-3 polyunsaturated fatty acid is relevant with competitive inhibition cyclooxygenase activity and then minimizing AA generation PGs, blood pressure regulation and vascular resistance thus.
4, to the influence of red cell deformability and viscosity of blood: the renal insufficiency person, progression of atherosclerosis is very rapid, accepting continuous peritoneal dialysis and 14 examples in 9 examples accepts to use the n-3 unsaturated fatty acids among the patient of renal transplantation, when discovery gives the treatment of low dose of n-3 polyunsaturated fatty acid, red cell deformability strengthens, thereby viscosity of blood also descends to some extent, and its mechanism is relevant with the fatty acid content in the hemocyte phosphatide with the configuration that the n-3 polyunsaturated fatty acid changes plasma proteins.
5, to the influence of heart: the n-3 polyunsaturated fatty acid can resist heart ventricle arrhythmia, because of it has β retardance or angiotensin-converting enzyme (ACE) restraining effect, thereby reduce heart stalk patient's mortality ratio, reduce the incidence of heart patient's plyability premature beat 70%, the n-3 polyunsaturated fatty acid of every month picked-up 5.5g can obtain the dangerous effect that reduces half of cardiac arrest.
Three, to the influence of upgrowth and development of children
To studies confirm that of rhesus monkey, the absorption at Gestation period restriction n-3 polyunsaturated fatty acid can influence the filial generation eyesight, and abnormal retinal map of current (ERG) and polydipsia appear in the damage learning capacity.To discovering of mouse, with the damage of the Δ 4 desaturase systems of age growth, be the reason that causes retina DHA density loss, the normal sight sensor of rat and primate needs DHA.53 routine scatterbrained childhood hyperkinetic syndromes (ADHD) discover that the infant group is compared with the contrast level, and blood plasma unsaturated fatty acids (AA, EPA, DHA) level is obviously lower.
In sum, the n-3 polyunsaturated fatty acid not only has good Dietotherapy health to be worth, and has pharmacological activity widely as the indispensable fatty acid of human body.Contain a large amount of n-3 polyunsaturated fatty acids in the Ascidian lipid acid, thereby can be widely used in reducing blood-fat, improve and treat cardiovascular and cerebrovascular diseases, anti-curing cancers, regulate and improve upgrowth and development of children and anti-inflammatory and immunomodulatory aspect.
(4) embodiment:
In order to understand better and to implement, describe the present invention's a kind of Ascidian lipid acid its preparation method and application thereof in detail below in conjunction with embodiment.
Embodiment 1, with fresh Ciona clean, air-dry, pulverize 540g dry powder, with the ethyl acetate is entrainment agent, and interpolation speed is 700ml/h, and carbon dioxide flow is in liquid state 20-24L/h, at 20MPa, extract 90min under 50 ℃ of conditions, then carbonic acid gas global cycle amount 46L gets yellow limpid clear solution 1000ml, get 30ml oily matter with rotatory evaporator reclaim under reduced pressure ethyl acetate, i.e. the sweet three ester crude extract-crude oils of Ascidian lipid acid;
Come unstuck: crude oil is heated to 40 ℃, under the 60r/min agitation condition, drips 85% phosphoric acid, addition is a weight of oil 0.02%, reduces stirring velocity behind the 10min to 15r/min, adds 60 ℃ of hot water of weight of oil 10%, be warming up to 70 ℃, constant temperature stirs 30min, the centrifugation oil foot thing that must come unstuck;
Depickling: degummed oil changes the alkali refining pot over to, is heated to 40 ℃ and sprays into 10% sodium hydroxide solution 5ml, continue to be heated to 60 ℃ (1 ℃/min), stir 10min, 15r/min, constant temperature leaves standstill, and emits soap stock, wash 2-3 time, must depickling oil;
Decolouring: depickling oil changes bleacher over to, after the vacuum hydro-extraction, is heated to 80-90 ℃, adds 3% activated carbon and carclazyte, and its ratio is 1: 3, stirs 20-30min, is cooled to 60-70 ℃, and press filtration gets bleached oil;
Deodorization: bleached oil sucks the vacuum deodorization jar, is heated to 100 ℃ with water vapor, sprays into water vapor, at 0.09MPa, deodorization 90min under 190 ℃ of conditions is cooled to 130 ℃, is cooled to 70 ℃, vacuum breaker, room temperature leaves standstill, and filters to such an extent that processed oil is promptly made with extra care sweet three esters of Ascidian lipid acid.
Sweet three esters of above-mentioned Ascidian lipid acid learn that after tested wherein EPA, DHA content are 〉=20%.
Adopt sweet three esters of above-mentioned Ascidian lipid acid routinely technology make soft capsule, can be used for promoting intelligence and strengthening brain, promote upgrowth and development of children.
Embodiment 2, with fresh Styela clava 150Kg, cleaning drains, at 0.09MPa, pulverize after the vacuum-drying under 60 ℃ of conditions, get dry powder 10Kg, extract 3h with 5 times of volume aether backflow, get sweet three esters of Ascidian lipid acid, yield 5% adopts and must make with extra care sweet three esters of Ascidian lipid acid with the process for refining of embodiment 1;
Saponification: in sweet three esters of above-mentioned 300g Ascidian lipid acid, add 1000ml, 9% potassium hydroxide ethanol (95% ethanol) liquid, reflux 2h under the nitrogen protection, reclaim alcohol excess, add 1000ml water, to PH=1, separate upper strata Ascidian lipid acid with 20% sulfuric acid acidation, wash 2 times, centrifugal dewater Ascidian lipid acid; For garnet thick;
Divide and carry: above-mentioned 300g Ascidian lipid acid adds 1000ml acetone (9: 1), stirs, and does the cooling agent cooling with acetone dry ice, 1.5 ℃/min, reduce to-47 ℃, constant temperature 25min, stir (15r/min), draw mother liquor, reclaim solvent, must concentrate the Ascidian polyunsaturated fatty acid, the secondary branch is carried, be cooled to-51 ℃ with 1.5 ℃/min, constant temperature 40min must concentrate Ascidian lipid acid.
Above-mentioned Ascidian lipid acid learns that after tested wherein EPA, DHA content are 〉=50%.
Adopt above-mentioned Ascidian lipid acid routinely technology make soft capsule, can be used for promoting intelligence and strengthening brain.
Embodiment 3, with Ciona cleaning, draining, air-dry pretreated pulverizing, get Ciona dry powder 500g, extract 3h with 5 times of volume aether backflow, get the poly-crude oil of sweet three esters of Ascidian fatty ester, yield 6.16% adopts the process for refining with embodiment 1 to get sweet three esters of purified Ascidian lipid acid;
Saponification: add 100ml, 9% potassium hydroxide methanol solution in sweet three esters of above-mentioned 30g Ascidian lipid acid, 60 ℃ of water-baths, 2h removes excessive methanol under reduced pressure;
Acidifying: in raffinate, add 100ml water,, tell upper strata Ascidian lipid acid with 75g, 25% sulfuric acid acidation;
Esterification: add 75ml methyl alcohol in the above-mentioned Ascidian lipid acid, 60 ℃, 2h take out the upper strata methyl esters, are washed to neutrality, and anhydrous sodium sulfate drying gets the Ascidian fatty acid methyl ester.
Above-mentioned Ascidian fatty acid methyl ester is learnt wherein DHA content 〉=20% after tested.
Adopt above-mentioned Ascidian fatty acid methyl ester routinely technology make microcapsule, add in the milk powder with 1%, but promoting intelligence and strengthening brain promotes upgrowth and development of children.
Embodiment 4, with embodiment 3, get sweet three esters of purified Ascidian lipid acid; With 500ml, 1% alcohol sodium alcohol solution, stir sweet three esters of adding 100ml above-mentioned purified Ascidian lipid acid, room temperature 20-25 ℃ of reaction 5h, upper strata ester layer is washed to PH=7 with 50 ℃ of hot water, and the centrifugal Ascidian fatty-acid ethyl ester that gets charges into nitrogen protection;
Divide and carry: Ascidian fatty-acid ethyl ester direct crystallization branch is carried: one-level: 5 ℃, 12h; Secondary: 0 ℃, 12h; Three grades :-5 ℃, 12h;
Concentrate: be concentrated into 1/2nd volumes under 6.5-13.3KPa, 180-190 ℃, nitrogen protective condition, the nitrogen protection drops to room temperature, then must concentrate the Ascidian fatty-acid ethyl ester;
The urea bag: add 1600ml in the 300g urea, 95% ethanol mixes with the above-mentioned Ascidian fatty-acid ethyl ester of 200ml, heated and stirred is reduced to room temperature to limpid transparent, filter crystallization, with a small amount of filtrate wash crystallization, press filtration gets filtrate, filtrate is reclaimed solvent, with 50 ℃ of washings, must concentrate the Ascidian fatty-acid ethyl ester;
Deodorization: the decompression 30min that bleeds under 7-13KPa, 180-190 ℃, nitrogen protective condition, reduce to room temperature and get the deodorization ethyl ester; Adopt molecular distillation can get the Ascidian fatty-acid ethyl ester of different purity.
Above-mentioned Ascidian fatty acid methyl ester is learnt wherein EPA and DHA content 〉=70% after tested.
Adopt above-mentioned Ascidian fatty-acid ethyl ester routinely technology make soft capsule, be used for reducing blood-fat, can prevent and treat cardiovascular and cerebrovascular diseases.
Claims (10)
1, sweet three esters of Ascidian lipid acid, it be by Ascidian through pre-treatment, extraction, refining, make after the refining classification.
2, Ascidian lipid acid, be by sweet three esters of the described Ascidian lipid acid of claim 1 through saponification, acidifying, make after the refining classification.
3, Ascidian fatty acid methyl ester or ethyl ester, be by by the described Ascidian lipid acid of claim 2 through esterification, make after the refining classification, also can directly carry out esterification by sweet three esters of the Ascidian lipid acid of claim 1, make after the refining classification.
4, press claim 1 or 2 or 3 described Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters, it is characterized in that content is in timnodonic acid, docosahexenoic acid weight 〉=10% in Ascidian lipid acid and methyl esters thereof, ethyl ester, sweet three esters.
5, the preparation method of described Ascidian lipid acid of claim 1-3 and methyl esters thereof, ethyl ester, sweet three esters, this method comprises following processing step:
A, pre-treatment, with fresh Ascidian clean, drain, dry, pulverize;
B extracts, pretreated Ascidian through extract the sweet three ester crude extracts of Ascidian lipid acid, i.e. crude oil, crude oil through come unstuck, after the depickling, decolouring, deodorization, dewaxing refining sweet three esters of purified Ascidian lipid acid;
C, saponification, acidifying, sweet three esters of the Ascidian lipid acid of above-mentioned steps get Ascidian lipid acid after saponification, acidifying;
D, esterification, the Ascidian lipid acid of above-mentioned steps gets Ascidian fatty acid methyl ester or ethyl ester through esterification, and sweet three esters of the Ascidian lipid acid that also available extraction step obtains directly carry out esterification and get Ascidian fatty acid methyl ester or ethyl ester.
6, by the preparation method of the described Ascidian lipid acid of claim 5 and methyl esters thereof, ethyl ester, sweet three esters, it is characterized in that described pre-treatment step drying temperature is lower than 80 degree, that drying comprises is air-dry, oven dry, vacuum-drying, lyophilize.
7,, it is characterized in that extraction in the described extraction step is any one in supercritical extraction, the solvent extraction by the preparation method of the described Ascidian lipid acid of claim 5 and methyl esters thereof, ethyl ester, sweet three esters.
8, described Ascidian lipid acid of claim 1-3 and methyl esters thereof, ethyl ester, the application of sweet three esters aspect preparation lipid-reducing function food, medicine and related medical health-care product.
9, described Ascidian lipid acid of claim 1-3 and methyl esters thereof, ethyl ester, the application of sweet three esters aspect functional food, medicine and the related medical health-care product of preparation improvement and treatment cardiovascular and cerebrovascular diseases.
10, described Ascidian lipid acid of claim 1-3 and methyl esters thereof, ethyl ester, sweet three esters are regulated and are improved application aspect functional food, medicine and the related medical health-care product of upgrowth and development of children in preparation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03111710A CN1431188A (en) | 2003-01-09 | 2003-01-09 | Method for preparing sea squirt fatty acids and methyl ester, ethyl ester, triglyceride and its preparing method as well as application infunctional food and drugs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN03111710A CN1431188A (en) | 2003-01-09 | 2003-01-09 | Method for preparing sea squirt fatty acids and methyl ester, ethyl ester, triglyceride and its preparing method as well as application infunctional food and drugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1431188A true CN1431188A (en) | 2003-07-23 |
Family
ID=4790148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN03111710A Pending CN1431188A (en) | 2003-01-09 | 2003-01-09 | Method for preparing sea squirt fatty acids and methyl ester, ethyl ester, triglyceride and its preparing method as well as application infunctional food and drugs |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1431188A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011106866A1 (en) * | 2010-03-01 | 2011-09-09 | National Research Council Of Canada | Tunicate extracts and uses thereof for treating metabolic disorders |
| CN102597249A (en) * | 2009-09-04 | 2012-07-18 | 弗雷德里克·诺伦 | A system to produce feedstock for biogas production |
| CN102648923A (en) * | 2011-02-28 | 2012-08-29 | 中国水产科学研究院东海水产研究所 | Amaroucium constellatum lipophilic extract |
| CN103168089A (en) * | 2010-06-17 | 2013-06-19 | 卑尔根技术交易股份公司 | Method |
| CN103848734A (en) * | 2014-01-14 | 2014-06-11 | 中国科学院海洋研究所 | Method for extracting natural EPA (eicosapentaenoic acid) and DHA (eicosapentaenoic acid) |
| CN112472723A (en) * | 2020-12-14 | 2021-03-12 | 烟台大学 | A product containing sea squirt inner bag and its preparation method |
-
2003
- 2003-01-09 CN CN03111710A patent/CN1431188A/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102597249A (en) * | 2009-09-04 | 2012-07-18 | 弗雷德里克·诺伦 | A system to produce feedstock for biogas production |
| WO2011106866A1 (en) * | 2010-03-01 | 2011-09-09 | National Research Council Of Canada | Tunicate extracts and uses thereof for treating metabolic disorders |
| CN103168089A (en) * | 2010-06-17 | 2013-06-19 | 卑尔根技术交易股份公司 | Method |
| CN102648923A (en) * | 2011-02-28 | 2012-08-29 | 中国水产科学研究院东海水产研究所 | Amaroucium constellatum lipophilic extract |
| CN103848734A (en) * | 2014-01-14 | 2014-06-11 | 中国科学院海洋研究所 | Method for extracting natural EPA (eicosapentaenoic acid) and DHA (eicosapentaenoic acid) |
| CN103848734B (en) * | 2014-01-14 | 2016-03-16 | 中国科学院海洋研究所 | A kind of method extracting natural EPA and DHA |
| CN112472723A (en) * | 2020-12-14 | 2021-03-12 | 烟台大学 | A product containing sea squirt inner bag and its preparation method |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9200236B2 (en) | Omega 7 rich compositions and methods of isolating omega 7 fatty acids | |
| CN104988190B (en) | A kind of structural type triglycerides rich in medium chain fatty acid and preparation method thereof | |
| KR102271711B1 (en) | Eicosapentaenoic acid (epa) formulations | |
| JP4518674B2 (en) | Use of docosapentaenoic acid-containing substances | |
| CN103493908B (en) | Nut blend oil with lipid lowering and blood glucose reducing effects and preparation method thereof | |
| JPH06505384A (en) | Arachidonic acid, its production and use | |
| CN101715913B (en) | Capsule for regulating blood fat and production process thereof | |
| CN103060080A (en) | Preparation method of blood-fat-reducing camellia oil | |
| CN103156198A (en) | Fish oil soft capsules and preparation method thereof | |
| CN104288345A (en) | A traditional Chinese medicine composition assisting blood lipid reduction and a preparing method thereof | |
| CN110257446B (en) | Preparation method of high-purity EPA glyceride and DHA glyceride | |
| CN101057873A (en) | Method for preparing hepatitis B virus resisting maggot protein powder and its maggot oil and fatty acid | |
| CN1331422C (en) | Pupa oil and production process thereof | |
| CN1431188A (en) | Method for preparing sea squirt fatty acids and methyl ester, ethyl ester, triglyceride and its preparing method as well as application infunctional food and drugs | |
| CN1204238C (en) | Kenrel oil composite extracted from plant kernel and its extraction process and application | |
| TW200522939A (en) | Composition having action preventing or alleviating symptoms or diseases due to aging of blood vessels | |
| CN103805644B (en) | Oils and fats containing double; two long-chain polyunsaturated fatty acids and preparation thereof and application | |
| CN1078198C (en) | Process for extracting linolenic acid and producing soft capsules using linolenic acid | |
| JP2013535957A (en) | Method for obtaining desired pharmaceutical and nutritional fatty acids | |
| CN102106534A (en) | Composition for assisting in lowering blood fat and preparation method thereof | |
| CN109845840A (en) | The preparation method of saturated fatty acid and middle long chain fatty acids structured lipid | |
| CN109527579A (en) | A kind of application of surprise Asia seed oil product and preparation method thereof and the sub- seed oil product of the surprise | |
| CN1679593A (en) | Composite preparation containing alpha-linolenic acid free acid, soybean phospholipid and vitamin E | |
| CN105132153B (en) | A method of preparing squid liver oil | |
| CN1842329A (en) | Preventive or ameliorating agent for liver disease involving hepatopathy |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| ASS | Succession or assignment of patent right |
Owner name: YINTAI UNIVERSITY Free format text: FORMER OWNER: WANG ZHANGHAI Effective date: 20030731 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20030731 Address after: 264005 Qingquan village, Laishan District, Shandong, Yantai Province, Yantai University Applicant after: Yantai University Address before: 264005 Qingquan village, Laishan District, Shandong, Yantai Province, Yantai University Applicant before: Wang Changhai |
|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |