JP5860482B2 - オキアミ油の製造方法およびこの方法で製造されたオキアミ油 - Google Patents
オキアミ油の製造方法およびこの方法で製造されたオキアミ油 Download PDFInfo
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- 229940106134 krill oil Drugs 0.000 title claims description 39
- 238000004519 manufacturing process Methods 0.000 title claims description 23
- 238000000034 method Methods 0.000 title description 12
- 241000239366 Euphausiacea Species 0.000 claims description 63
- 102000035195 Peptidases Human genes 0.000 claims description 27
- 108091005804 Peptidases Proteins 0.000 claims description 27
- 238000006911 enzymatic reaction Methods 0.000 claims description 20
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 claims description 19
- 235000013793 astaxanthin Nutrition 0.000 claims description 19
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 claims description 19
- 229940022405 astaxanthin Drugs 0.000 claims description 19
- 239000001168 astaxanthin Substances 0.000 claims description 19
- 150000003904 phospholipids Chemical class 0.000 claims description 19
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound 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 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000706 filtrate Substances 0.000 claims description 12
- 239000010802 sludge Substances 0.000 claims description 12
- 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 11
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 11
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 11
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 11
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 10
- 230000007935 neutral effect Effects 0.000 claims description 9
- 230000035484 reaction time Effects 0.000 claims description 9
- 102000005741 Metalloproteases Human genes 0.000 claims description 8
- 108010006035 Metalloproteases Proteins 0.000 claims description 8
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 8
- 101710184263 Alkaline serine protease Proteins 0.000 claims description 7
- 241000193744 Bacillus amyloliquefaciens Species 0.000 claims description 6
- 241000194108 Bacillus licheniformis Species 0.000 claims description 6
- 244000063299 Bacillus subtilis Species 0.000 claims description 6
- 235000014469 Bacillus subtilis Nutrition 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229940067631 phospholipid Drugs 0.000 claims description 6
- 238000010298 pulverizing process Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000012153 distilled water Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 238000011084 recovery Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 235000013305 food Nutrition 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 2
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000012041 food component Nutrition 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 241000239370 Euphausia superba Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283279 Mysticeti Species 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 108010055297 Sterol Esterase Proteins 0.000 description 1
- 102000000019 Sterol Esterase Human genes 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 235000021049 nutrient content Nutrition 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000007065 protein hydrolysis Effects 0.000 description 1
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/02—Pretreatment
- C11B1/025—Pretreatment by enzymes or microorganisms, living or dead
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
- C12Y304/21—Serine endopeptidases (3.4.21)
- C12Y304/21014—Microbial serine proteases (3.4.21.14)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y304/00—Hydrolases acting on peptide bonds, i.e. peptidases (3.4)
- C12Y304/24—Metalloendopeptidases (3.4.24)
- C12Y304/24004—Microbial metalloproteinases (3.4.24.4)
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Microbiology (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Edible Oils And Fats (AREA)
- Biotechnology (AREA)
- General Chemical & Material Sciences (AREA)
Description
オキアミの準備
冷凍されたオキアミを解凍し、水で洗浄して塩分および不純物を除去した試料と、凍結乾燥したオキアミの試料を準備し、その栄養成分の含量を分析し、その結果を下記表1に示した。
実施例1〜4
冷凍されたオキアミをミキサーで粉砕した試料に蒸留水とタンパク質分解酵素を添加し、30、50、70および100MPaの超高圧と、55℃の温度で加水分解し、液化させた。前記タンパク質分解酵素として、バチルスリケニフォルミスから分離されたアルカリ性セリンプロテアーゼ、およびバチルスサブチリスとバチルスアミロリケファシエンスから分離された中性メタロプロテアーゼが混合された液を使用した。前記アルカリ性セリンプロテアーゼおよび前記中性メタロプロテアーゼは低温水抽出法によって分離できる。
冷凍されたオキアミをミキサーで粉砕した試料に蒸留水とタンパク質分解酵素を添加し、常圧及び55℃の温度で12時間反応させて加水分解し、液化させた。前記タンパク質分解酵素として、バチルスリケニフォルミスから分離されたアルカリ性セリンプロテアーゼ、およびバチルスサブチリスとバチルスアミロリケファシエンスから分離された中性メタロプロテアーゼが混合された液を使用した。
冷凍されたオキアミをミキサーで粉砕した試料に蒸留水を添加し、100MPaの超高圧および55℃の温度で12時間反応させて加水分解し、液化させた。前記蒸留水は前記オキアミの100重量部に対して100重量部添加した。実施例5とは異なり、タンパク質分解酵素を添加せず、超高圧反応器を用いてオキアミ油を製造した。
冷凍されたオキアミをミキサーで粉砕した試料に蒸留水とタンパク質分解酵素を添加し、100MPaの超高圧および55℃の温度で12時間反応させて加水分解し、液化させた。超高圧反応器を使用した以外は実施例5と同様の方法で、オキアミ油を製造した。
凍結乾燥したオキアミをミキサーで粉砕した試料に蒸留水とタンパク質分解酵素を添加し、100MPaの超高圧および55℃の温度で12時間反応させて加水分解し、液化させた。凍結乾燥したオキアミを使用した以外は実施例7と同様の方法で、オキアミ油を製造した。
Claims (8)
- オキアミを準備するステップと、
前記オキアミにタンパク質分解酵素を添加して、酵素反応を行うステップと、
前記酵素反応の行われた前記オキアミから、エイコサペンタエン酸、ドコサヘキサエン酸、リン脂質およびアスタキサンチンを抽出するステップと、
前記抽出されたエイコサペンタエン酸、ドコサヘキサエン酸、リン脂質およびアスタキサンチンを混合するステップとを含んでなり、
前記タンパク質分解酵素は、バチルスリケニフォルミスから分離されたアルカリ性セリンプロテアーゼ、およびバチルスサブチリスとバチルスアミロリケファシエンスから分離された中性メタロプロテアーゼを含むことを特徴とする、オキアミ油の製造方法。 - 前記酵素反応が超高圧反応器で行われることを特徴とする、請求項1に記載のオキアミ油の製造方法。
- 前記超高圧反応器において、反応圧力が10〜300MPaであり、反応温度が50〜60℃であり、反応時間が3〜24時間であることを特徴とする、請求項2に記載のオキアミ油の製造方法。
- 前記超高圧反応器で、前記タンパク質分解酵素の添加された前記オキアミが液化することを特徴とする、請求項2に記載のオキアミ油の製造方法。
- 前記酵素反応の後、前記液化したオキアミのpHが3.0〜5.0に調節されることを特徴とする、請求項4に記載のオキアミ油の製造方法。
- 前記酵素反応の後、前記液化したオキアミが濾過されて濾液とスラッジに分離され、前記エイコサペンタエン酸、ドコサヘキサエン酸およびリン脂質が前記濾液を遠心分離することにより抽出され、
前記アスタキサンチンは前記スラッジをエタノールで洗浄することにより抽出されることを特徴とする、請求項4に記載のオキアミ油の製造方法。 - 前記オキアミを準備するステップが、前記オキアミを粉砕するステップを含むことを特徴とする、請求項1に記載のオキアミ油の製造方法。
- 前記酵素反応の前に、前記オキアミのpHが7.5〜9.0に調節されることを特徴とする、請求項1に記載のオキアミ油の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR1020110012550A KR101045258B1 (ko) | 2011-02-11 | 2011-02-11 | 크릴 오일 제조 방법 및 상기 방법에 의해 제조된 크릴 오일 |
KR10-2011-0012550 | 2011-02-11 | ||
PCT/KR2011/005386 WO2012108593A1 (ko) | 2011-02-11 | 2011-07-21 | 크릴 오일 제조 방법 및 상기 방법에 의해 제조된 크릴 오일 |
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JP5860482B2 true JP5860482B2 (ja) | 2016-02-16 |
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Country Status (9)
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US (1) | US8624046B2 (ja) |
EP (1) | EP2674034B1 (ja) |
JP (1) | JP5860482B2 (ja) |
KR (1) | KR101045258B1 (ja) |
CN (1) | CN103501623B (ja) |
CA (1) | CA2827085C (ja) |
NO (1) | NO2674034T3 (ja) |
PL (1) | PL2674034T3 (ja) |
WO (1) | WO2012108593A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
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NZ599618A (en) * | 2009-10-30 | 2014-08-29 | Tharos Ltd | Solvent-free process for obtaining phospholipids and neutral enriched krill oils |
CN103305335B (zh) * | 2013-06-27 | 2015-04-29 | 日照海大博远海洋生物科技有限公司 | 一种低温逆流提取南极磷虾虾油的方法 |
KR101499199B1 (ko) * | 2013-11-04 | 2015-03-09 | 부경대학교 산학협력단 | 저불소, 저산가, 저과산화물가 및 고아스타잔틴 크릴 오일의 제조 방법 및 이에 의하여 제조된 크릴 오일 |
US20180207204A1 (en) * | 2014-02-11 | 2018-07-26 | Enzymotec Ltd. | Krill oil preparations with optimal mineral and metal composition, low impurities and low and stable tma levels |
CN104388176B (zh) * | 2014-11-10 | 2017-01-25 | 大连工业大学 | 水酶法制备南极磷虾油及其微胶囊和低氟南极磷虾肽的方法 |
CN104357206A (zh) * | 2014-11-18 | 2015-02-18 | 董寰 | 一种水酶法制备富含磷脂的南极磷虾油的方法 |
CN104522728B (zh) * | 2014-11-27 | 2017-10-20 | 山东好当家海洋发展股份有限公司 | 一种利用海参漂烫液提取磷脂及海参油的方法 |
CN104450163A (zh) * | 2014-12-08 | 2015-03-25 | 上海市同济医院 | 外源酶解提取高含量dha+epa磷虾油的方法 |
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