JP2002080887A - Method for manufacturing docosapentaenoic acid-having glyceride - Google Patents
Method for manufacturing docosapentaenoic acid-having glycerideInfo
- Publication number
- JP2002080887A JP2002080887A JP2000266569A JP2000266569A JP2002080887A JP 2002080887 A JP2002080887 A JP 2002080887A JP 2000266569 A JP2000266569 A JP 2000266569A JP 2000266569 A JP2000266569 A JP 2000266569A JP 2002080887 A JP2002080887 A JP 2002080887A
- Authority
- JP
- Japan
- Prior art keywords
- docosapentaenoic acid
- glyceride
- oil
- dpa
- acid
- 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.)
- Granted
Links
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 title claims abstract description 63
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- 235000021294 Docosapentaenoic acid Nutrition 0.000 claims abstract description 22
- 102000004882 Lipase Human genes 0.000 claims abstract description 18
- 108090001060 Lipase Proteins 0.000 claims abstract description 18
- 239000004367 Lipase Substances 0.000 claims abstract description 18
- 235000019421 lipase Nutrition 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 229940119224 salmon oil Drugs 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 15
- 235000019197 fats Nutrition 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 abstract description 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 42
- 235000019198 oils Nutrition 0.000 description 42
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 239000003925 fat Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 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 description 8
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 8
- 241000283216 Phocidae Species 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 235000021588 free fatty acids Nutrition 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 6
- 238000000199 molecular distillation Methods 0.000 description 6
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 5
- 238000006911 enzymatic reaction Methods 0.000 description 5
- 235000014593 oils and fats Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241001529469 Phoca groenlandica Species 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- -1 EPA and DHA Chemical class 0.000 description 3
- 241000589516 Pseudomonas Species 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241000588986 Alcaligenes Species 0.000 description 2
- 240000002900 Arthrospira platensis Species 0.000 description 2
- 235000016425 Arthrospira platensis Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001149724 Cololabis adocetus Species 0.000 description 2
- 241000195493 Cryptophyta Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 241000235395 Mucor Species 0.000 description 2
- 241000277329 Oncorhynchus keta Species 0.000 description 2
- 241000235527 Rhizopus Species 0.000 description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 2
- 235000019512 sardine Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940082787 spirulina Drugs 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 241000555825 Clupeidae Species 0.000 description 1
- 102100032768 Complement receptor type 2 Human genes 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 101000941929 Homo sapiens Complement receptor type 2 Proteins 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 241001562081 Ikeda Species 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000277338 Oncorhynchus kisutch Species 0.000 description 1
- 241000277277 Oncorhynchus nerka Species 0.000 description 1
- 241000199919 Phaeophyceae Species 0.000 description 1
- 101001062854 Rattus norvegicus Fatty acid-binding protein 5 Proteins 0.000 description 1
- 241000206572 Rhodophyta Species 0.000 description 1
- 241000269851 Sarda sarda Species 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 241001504592 Trachurus trachurus Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 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 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
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 150000001982 diacylglycerols Chemical class 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002759 monoacylglycerols Chemical class 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は水産油脂からドコサ
ペンタエン酸が濃縮されたドコサペンタエン酸含有グリ
セリドを製造するドコサペンタエン酸含有グリセリドの
製造方法に関する。TECHNICAL FIELD The present invention relates to a method for producing docosapentaenoic acid-containing glyceride from marine fats and oils to produce docosapentaenoic acid-containing glyceride.
【０００２】[0002]
【従来の技術】イワシ、サバ、サンマ、アジ等の魚類の
脂質（魚油）、あるいは紅藻、褐藻などの藻類の脂質、
甲殻類並びに貝類や海産動物類の脂質などの構成脂肪酸
中には、高度不飽和脂肪酸（以下、PUFAと略す）が多量
に含まれている。このうち、エイコサペンタエン酸（以
下、EPAと略す）やドコサヘキサエン酸（以下、DHAと略
す）などはω-3系列の不飽和脂肪酸であり、特にEPAは
プロスタグランジンやトロンボキサンとの関連性におい
て、近年その生理活性が注目され、動脈硬化や高脂血症
の医薬品として既に市販されている。また、医薬品分野
だけでなく、食品全般、飼料などの素材として多岐にわ
たって利用されている。2. Description of the Related Art Lipids of fish (fish oil) such as sardines, mackerel, saury and horse mackerel, or lipids of algae such as red algae and brown algae,
Constituent fatty acids such as lipids of crustaceans, shellfish and marine animals contain a large amount of polyunsaturated fatty acids (hereinafter abbreviated as PUFA). Of these, eicosapentaenoic acid (hereinafter abbreviated as EPA) and docosahexaenoic acid (hereinafter abbreviated as DHA) are unsaturated fatty acids of the ω-3 series. In recent years, its physiological activity has attracted attention, and it has already been marketed as a drug for arteriosclerosis and hyperlipidemia. In addition to being used in the pharmaceutical field, it is widely used as a raw material for foods and feeds.
【０００３】一方、ドコサペンタエン酸（以下、DPAと
略す）は、EPAやDHA同様ω-3系列の脂肪酸であるが、こ
れを含有する油脂は特殊な魚油等に限られており、その
濃度も1〜2％と低いものである。しかしながら、DPAはE
PAと比較してはるかに高い生理活性が確認されており
（例えば「Prostaglandins, Leucotriens and Essentia
l Fatty Acids(1996),54,319-325」参照)、DPAを濃縮し
たグリセリドについて、医薬品及び食品への応用が期待
されている。On the other hand, docosapentaenoic acid (hereinafter abbreviated as DPA) is an ω-3 series fatty acid like EPA and DHA, but the fats and oils containing it are limited to special fish oils and the like. Is also as low as 1-2%. However, DPA is
Much higher bioactivity has been confirmed as compared to PA (eg, "Prostaglandins, Leucotriens and Essentia").
l Fatty Acids (1996), 54, 319-325 "), and glycerides enriched in DPA are expected to be applied to pharmaceuticals and foods.
【０００４】なお、以下の説明では、グリセリドとは、
モノアシルグリセロール、ジアシルグリセロール、トリ
アシルグリセロールの混合物と定義する。[0004] In the following description, glyceride means
It is defined as a mixture of monoacylglycerol, diacylglycerol, and triacylglycerol.
【０００５】ここで、従来のグリセリドの形でEPA,DPA,
DHA等のPUFAを濃縮する方法としては、 （１）リパーゼによる加水分解法 （２）ウインタリング法（低温分別法または低温溶媒分
別法） （３）分子蒸留法 等が知られている。[0005] Here, EPA, DPA,
As methods for concentrating PUFA such as DHA, (1) hydrolysis method using lipase, (2) wintering method (low-temperature fractionation method or low-temperature solvent fractionation method), and (3) molecular distillation method are known.
【０００６】[0006]
【発明が解決しようとする課題】しかしながら、前述の
ようにDPAを含有する油脂は限られており、しかも脂肪
酸純度も1〜2％と低い。従って、例えばDPA純度5％以上
のグリセリドを得るためには、溶媒分別法と酵素反応、
あるいはエステル交換反応、合成法（遊離脂肪酸とグリ
セリンとの脱水縮合反応）等の他の工程を組み合わせな
ければならず、煩雑であり、また得られる油脂の収率も
低く、製造コストも非常に高くなるという問題点があっ
た。However, as described above, fats and oils containing DPA are limited, and fatty acid purity is as low as 1 to 2%. Therefore, for example, in order to obtain a glyceride having a DPA purity of 5% or more, a solvent fractionation method and an enzymatic reaction,
Alternatively, other steps such as a transesterification reaction and a synthesis method (dehydration condensation reaction between free fatty acid and glycerin) must be combined, which is complicated, and the yield of the obtained fats and oils is low, and the production cost is very high. There was a problem of becoming.
【０００７】そこで、本発明は、煩雑な工程を経ること
なくDPAをグリセリドの形で収率良く、且つ低コストで
製造することのできるドコサペンタエン酸含有グリセリ
ドの製造方法を提供することを目的とする。Accordingly, an object of the present invention is to provide a method for producing docosapentaenoic acid-containing glyceride, which can produce DPA in the form of glyceride in good yield and at low cost without complicated steps. And
【０００８】[0008]
【課題を解決するための手段】上記目的を達成するため
に、本発明は、ドコサペンタエン酸含有グリセリドの製
造方法において、ドコサペンタエン酸を3％以上含有す
る水産油脂を原料とすることを特徴とする。In order to achieve the above object, the present invention provides a method for producing glyceride containing docosapentaenoic acid, which comprises using a marine oil or fat containing docosapentaenoic acid at 3% or more as a raw material. Features.
【０００９】一般的な水産動物の脂質中に含まれるDPA
含量は、例えばイワシ油約2.3％、サンマ油約1.2％、ス
ルメイカ肝油1.1％、ニシン油0.6％で、（改訂3版油脂
化学便覧、日本油化学協会編、p111、1990）3％を越え
るものは少ない。しかしながら、サケから抽出された油
脂中のDPA含量は3％を越え、アザラシから抽出された油
脂中のDPA含量は4％を越えるものであり、DPAに富むこ
とが知られている。DPA contained in lipids of common marine animals
The content is, for example, about 2.3% of sardine oil, about 1.2% of saury oil, 1.1% of squid liver oil, and 0.6% of herring oil. Is less. However, the DPA content in fats and oils extracted from salmon exceeds 3%, and the DPA content in fats and oils extracted from seals exceeds 4%, and is known to be rich in DPA.
【００１０】そこで、本発明は、DPAを含有する水産油
脂、特にサケ油又はアザラシ油を原料とし、リパーゼに
よりDPA以外を選択的に加水分解することでDPAをさらに
高純度に効率良く濃縮する。Therefore, the present invention uses DPA-containing marine oils and fats, particularly salmon oil or seal oil as a raw material, and selectively hydrolyzes other than DPA with a lipase to thereby efficiently concentrate DPA to a higher purity.
【００１１】ここで言う水産油脂とは水産動植物から得
られる油脂のことであり、魚類、哺乳類、藻類（微細藻
を含む）、その他水圏に生息する動植物由来の油脂を指
す。The marine oils and fats referred to herein are oils and fats obtained from marine animals and plants, and refer to fish and mammals, algae (including microalgae), and other oils and fats derived from animals and plants living in the aquatic sphere.
【００１２】サケ油は、ベニザケ、シロザケ、ギンザケ
等、DPAを含有する油脂であれば、全て使用が可能であ
るが、DPAを多く含むシロザケが特に好ましい。As salmon oil, any fats and oils containing DPA, such as sockeye salmon, chum salmon and coho salmon, can be used, but chum salmon rich in DPA are particularly preferred.
【００１３】アザラシ油は、ゴマフアザラシ、タテゴト
アザラシ等、DPAを含有する油脂であれば、全て使用が
可能である。As the seal oil, any oils and fats containing DPA such as sesame seals and harp seals can be used.
【００１４】リパーゼによる加水分解法を用いる際使用
するリパーゼとしては、アルカリゲネス（Alcaligenes)
属、キャンディダ(Candida)属、リゾプス(Rhizopus)
属、ムコール(Mucor)属、シュードモナス(Pseudomonas)
属、ジオトリカム(Geotricum)属、およびブタ膵臓に由
来したものが挙げられる。The lipase used when using the lipase hydrolysis method is Alcaligenes ( Alcaligenes ).
Genus Candida (Candida) genus, Rhizopus (Rhizopus)
Sp., Mucor (Mucor) genus Pseudomonas (Pseudomonas)
Genus, Jiotorikamu (Geotricum) genus, and those derived from the porcine pancreas.
【００１５】本発明において使用するリパーゼは、DPA
に対する反応性が低い酵素が必要条件である。また、ア
ザラシ油はグリセロールの1,3位にDPAを多く結合してい
るので、アザラシ油を使用するときは1,3特異型リパー
ゼよりランダム型リパーゼの方がより効果的で好まし
く、特にキャンディダ属及びシュードモナス属に由来す
るリパーゼが好ましい。The lipase used in the present invention is DPA
An enzyme with low reactivity to is a necessary condition. In addition, since seal oil has a large amount of DPA bound to positions 1 and 3 of glycerol, when using seal oil, random lipase is more effective and preferable than 1,3-specific lipase, particularly candy Lipases from the genus and Pseudomonas are preferred.
【００１６】なお、1ユニット（U）とは、オリーブ油を
基質として、1分間に1μmolの脂肪酸を遊離する酵素量
とする。[0016] One unit (U) is defined as the amount of enzyme that releases 1 µmol of fatty acid per minute using olive oil as a substrate.
【００１７】本発明で用いるリパーゼの反応条件は、以
下の通りである。The reaction conditions of the lipase used in the present invention are as follows.
【００１８】すなわち、リパーゼの使用量は、油脂1ｇ
あたり、10〜2000ユニット(U)の範囲であり、好ましく
は50〜600ユニット(U)である。That is, the amount of lipase used is 1 g of fats and oils.
Per unit is in the range of 10 to 2000 units (U), preferably 50 to 600 units (U).
【００１９】水の添加量は油脂に対して5〜500重量％の
範囲であり、好ましくは10〜200重量％である。The amount of water to be added is in the range of 5 to 500% by weight, preferably 10 to 200% by weight, based on the fat or oil.
【００２０】pHは6.0〜10.0の範囲が好ましく、このpH
を調節するために緩衝液を用いるとさらに効果的で、pH
として7.0〜8.5が特に好ましい範囲である。The pH is preferably in the range of 6.0 to 10.0.
It is more effective to use a buffer to adjust the pH
7.0 to 8.5 is a particularly preferred range.
【００２１】反応は、大気下で行っても良いが、PUFAを
多量に含む場合は、不活性ガス下、例えば窒素ガス、炭
酸ガスの雰囲気下にしておくと脂肪酸の劣化を防ぐこと
ができる。また、酸化防止剤として、例えばトコフェロ
ール、カテキン類、BHA（ブチルヒドロキシアニソー
ル）、BHT（ジブチルヒドロキシトルエン）等を併用し
ても良い。The reaction may be carried out in the atmosphere. However, when a large amount of PUFA is contained, deterioration of the fatty acid can be prevented by setting the reaction in an inert gas atmosphere, for example, an atmosphere of nitrogen gas or carbon dioxide gas. Further, as an antioxidant, for example, tocopherol, catechins, BHA (butylhydroxyanisole), BHT (dibutylhydroxytoluene) and the like may be used in combination.
【００２２】反応温度は20〜60℃の範囲が好ましく、特
に25〜50℃の範囲が好ましい。The reaction temperature is preferably in the range of 20 to 60 ° C, particularly preferably in the range of 25 to 50 ° C.
【００２３】反応は撹拌した方が望ましいが、乳化状態
にして静置反応もできる。また、反応はバッチ式でも良
いが、連続式として固定化酵素カラムも使用できる。The reaction is desirably agitated, but the reaction may be carried out in an emulsified state. The reaction may be a batch system, but an immobilized enzyme column may be used as a continuous system.
【００２４】加水分解の程度は、反応中の加水分解油を
サンプリングし、酸価を測定することにより知ることが
できる。得られるDPAグリセリドの濃縮度及び収率は、
加水分解油の分解の程度、すなわち加水分解油の酸価に
よって推定できる。本発明の目的からは、加水分解油の
酸価が50〜150になった時点で反応を終了するのが望ま
しい。通常、1〜24時間の範囲内で行われる。The degree of hydrolysis can be determined by sampling the hydrolyzed oil during the reaction and measuring the acid value. The enrichment and yield of the resulting DPA glyceride are
It can be estimated from the degree of decomposition of the hydrolyzed oil, that is, the acid value of the hydrolyzed oil. For the purpose of the present invention, it is desirable to terminate the reaction when the acid value of the hydrolyzed oil reaches 50 to 150. Usually, it is performed within a range of 1 to 24 hours.
【００２５】もし、酸価が目標の値に達しない場合は、
反応時間や反応温度で調節できる。If the acid value does not reach the target value,
It can be adjusted by the reaction time and reaction temperature.
【００２６】上記加水分解油中には、目的物であるDPA
グリセリドのほかに遊離脂肪酸を含んでいるため、DPA
グリセリドを得る為には、遊離脂肪酸を除去する必要が
ある。脂肪酸を除去する方法としては、通常行われてい
るアルカリ脱酸法、分子蒸留法のほかに、溶剤抽出法、
イオン交換樹脂法、低温結晶法、及び減圧水蒸気蒸留
法、又はこれらを組み合わせた方法を適用する事ができ
る。これらリパーゼ処理後の各工程については特に限定
されるものではない。In the above hydrolyzed oil, the target substance, DPA, is contained.
Because it contains free fatty acids in addition to glyceride, DPA
To obtain glycerides, it is necessary to remove free fatty acids. As a method of removing fatty acids, in addition to the usual alkali deoxidation method, molecular distillation method, solvent extraction method,
An ion exchange resin method, a low-temperature crystallization method, a reduced pressure steam distillation method, or a combination thereof can be applied. The respective steps after the lipase treatment are not particularly limited.
【００２７】[0027]
【発明の実施の形態】以下、本発明を実施例について説
明するが、本発明はこれらの実施例に限定されるもので
はない。DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to these examples.
【００２８】[0028]
【実施例１】キャンディダ(Candida)属由来のリパーゼ
粉末0.05ｇ（360,000U/g)を水100ｇに溶解し、さらにタ
テゴトアザラシ油（EPA：7.0％、DPA：4.5％、DHA：9.0
％、酸価：1.0）100ｇを混合したものを、40℃、pH7.0
の条件下で24時間撹拌しながら酵素反応を行い、加水分
解油を得た。次いで、この加水分解油を遠心分離し、油
層を回収した後、水洗によりグリセリンを除去、続けて
流下薄膜式分子蒸留装置を用いて、真空度0.6Ps、蒸発
面温度180℃、流速60g/hの条件下で処理することによ
り、遊離脂肪酸の除去を行った。得られたグリセリド
(製品1)は45.9ｇであり、このグリセリドはDPA純度が7.
5％、DPA回収率が71.4％、酸価が0.6であった。EXAMPLE 1 0.05 g (360,000 U / g) of a lipase powder derived from the genus Candida was dissolved in 100 g of water, and further, harp seal oil (EPA: 7.0%, DPA: 4.5%, DHA: 9.0)
%, Acid value: 1.0) 100g was mixed at 40 ° C, pH 7.0
The enzyme reaction was carried out with stirring for 24 hours under the conditions described above to obtain a hydrolyzed oil. Next, the hydrolyzed oil was centrifuged, and after collecting the oil layer, glycerin was removed by washing with water.Continuously using a falling thin film molecular distillation apparatus, the degree of vacuum was 0.6 Ps, the evaporation surface temperature was 180 ° C., and the flow rate was 60 g / h. The free fatty acids were removed by the treatment under the following conditions. The resulting glyceride
(Product 1) weighs 45.9 g, and this glyceride has a DPA purity of 7.
5%, DPA recovery was 71.4%, and acid value was 0.6.
【００２９】[0029]
【実施例２】シュードモナス(psuedomonas)属由来のリ
パーゼ粉末0.05ｇ（90,000/g)を水100ｇに溶解し、さら
にタテゴトアザラシ油（EPA：7.2％、DPA：4.7％、DH
A：8.9％、酸価：1.0）100ｇを混合したものを、38℃、
pH7.0の条件下で24時間撹拌しながら酵素反応を行い、
加水分解油を得た。次いで、この加水分解油を遠心分離
し、油層を回収した後、水洗によりグリセリンを除去、
続けて流下薄膜式分子蒸留装置を用いて、真空度0.6P
s、蒸発面温度180℃、流速60g/hの条件下で処理するこ
とにより、遊離脂肪酸の除去を行った。得られたグリセ
リド(製品1)は49.8ｇであり、このグリセリドはDPA純度
が7.9％、DPA回収率が80.4％、酸価が0.6であった。Example 2 0.05 g (90,000 / g) of a lipase powder derived from the genus psuedomonas was dissolved in 100 g of water, and further, harp seal oil (EPA: 7.2%, DPA: 4.7%, DH
A: 8.9%, acid value: 1.0) 100 g was mixed at 38 ° C,
Perform the enzyme reaction with stirring for 24 hours under the condition of pH 7.0,
A hydrolyzed oil was obtained. Next, after centrifuging the hydrolyzed oil and collecting the oil layer, glycerin was removed by washing with water,
Then, using a falling film molecular distillation apparatus, the vacuum degree was 0.6P
The free fatty acids were removed by treating under the conditions of s, evaporation surface temperature of 180 ° C, and flow rate of 60 g / h. The obtained glyceride (product 1) weighed 49.8 g, and the glyceride had a DPA purity of 7.9%, a DPA recovery of 80.4%, and an acid value of 0.6.
【００３０】[0030]
【実施例３】キャンディダ(Candida)属由来のリパーゼ
粉末0.05ｇ（360,000U/g)を水100ｇに溶解し、さらにサ
ケ油（EPA：7.8％、DPA：3.2％、DHA：13.0％、酸価：
1.0）100ｇを混合したものを、40℃、pH7.0の条件下で2
4時間撹拌しながら酵素反応を行い、加水分解油を得
た。次いで、この加水分解油を遠心分離し、油層を回収
した後、水洗によりグリセリンを除去、続けて流下薄膜
式分子蒸留装置を用いて、真空度0.6Ps、蒸発面温度180
℃、流速60g/hの条件下で処理することにより、遊離脂
肪酸の除去を行った。得られたグリセリド(製品2)は42.
0ｇであり、このグリセリドはDPA純度が5.8％、DPA回収
率が75.1％、酸価が0.3であった。EXAMPLE 3 0.05 g (360,000 U / g) of a lipase powder derived from the genus Candida was dissolved in 100 g of water, and salmon oil (EPA: 7.8%, DPA: 3.2%, DHA: 13.0%, acid) Price:
1.0) 100 g was mixed at 40 ° C and pH 7.0 under 2
An enzymatic reaction was carried out with stirring for 4 hours to obtain a hydrolyzed oil. Next, the hydrolyzed oil was centrifuged, and after collecting the oil layer, glycerin was removed by washing with water.Then, using a falling thin film molecular distillation apparatus, the degree of vacuum was 0.6 Ps, and the evaporation surface temperature was 180.
Free fatty acids were removed by treating at 60 ° C. and a flow rate of 60 g / h. The resulting glyceride (Product 2) is 42.
The glyceride had a DPA purity of 5.8%, a DPA recovery of 75.1%, and an acid value of 0.3.
【００３１】[0031]
【比較例１】キャンディダ(Candida)属由来のリパーゼ
粉末0.05ｇ（360,000U/g)を水100ｇに溶解し、タテゴト
アザラシ油の代わりにカツオ油（EPA：4.8％、DPA：1.5
％、DHA：27.0％、酸価：0.5）100ｇを混合したもの
を、40℃、pH7.0の条件下で24時間撹拌しながら酵素反
応を行い、加水分解油を得た。次いで、この加水分解油
を遠心分離し、油層を回収した後、水洗によりグリセリ
ンを除去、続けて流下薄膜式分子蒸留装置を用いて、真
空度0.6Ps、蒸発面温度180℃、流速60g/hの条件下で処
理することにより、遊離脂肪酸の除去を行った。得られ
たグリセリド(製品1)は40.9ｇであり、このグリセリド
はDPA純度が1.2％、DPA回収率が32.7％、酸価が0.6であ
った。Comparative Example 1 0.05 g (360,000 U / g) of a lipase powder derived from the genus Candida was dissolved in 100 g of water, and bonito oil (EPA: 4.8%, DPA: 1.5) was used instead of harp seal oil.
%, DHA: 27.0%, acid value: 0.5), and then subjected to an enzymatic reaction with stirring at 40 ° C. and pH 7.0 for 24 hours to obtain a hydrolyzed oil. Next, the hydrolyzed oil was centrifuged, and after collecting the oil layer, glycerin was removed by washing with water.Continuously using a falling thin film molecular distillation apparatus, the degree of vacuum was 0.6 Ps, the evaporation surface temperature was 180 ° C., and the flow rate was 60 g / h. The free fatty acids were removed by the treatment under the following conditions. The obtained glyceride (product 1) weighed 40.9 g, and the glyceride had a DPA purity of 1.2%, a DPA recovery of 32.7%, and an acid value of 0.6.
【００３２】[0032]
【比較例２】1Lの3％含水アセトン中にアザラシ油100g
を溶解し、-40℃まで冷却した。16時間後、直ちに吸引
濾過により析出した固形脂を除去し、次いで濾液中のア
セトンをエバポレーターにより完全に留去した。得られ
たグリセリド(製品2)は66.3gであり、このグリセリドは
DPA純度が5.5％、DPA回収率が36％、酸価が0.9であっ
た。[Comparative Example 2] Seal oil 100 g in 1 L of 3% aqueous acetone
Was dissolved and cooled to -40 ° C. After 16 hours, the precipitated solid fat was immediately removed by suction filtration, and then acetone in the filtrate was completely distilled off by an evaporator. The obtained glyceride (Product 2) weighs 66.3 g, and this glyceride
DPA purity was 5.5%, DPA recovery was 36%, and acid value was 0.9.
【００３３】[0033]
【発明の効果】以上説明したように、本発明では、ドコ
サペンタエン酸含有油脂からリパーゼを用いた加水分解
法によりドコサペンタエン酸の濃縮されたドコサペンタ
エン酸含有グリセリドを製造するドコサペンタエン酸含
有グリセリドの製造方法において、ドコサペンタエン酸
を3.0％以上含有する水産油脂を原料とするので、煩雑
な工程を経ることなくDPAをグリセリドの形で収率良
く、且つ低コストで製造することができる。As described above, according to the present invention, a docosapentaenoic acid-containing glyceride in which docosapentaenoic acid is concentrated is produced from a docosapentaenoic acid-containing oil or fat by a hydrolysis method using lipase. In the method for producing an acid-containing glyceride, since a marine oil containing 3.0% or more of docosapentaenoic acid is used as a raw material, DPA can be produced in the form of glyceride at a high yield and at low cost without complicated steps. Can be.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 黄堂 泰昌 大阪府大阪市淀川区西中島１丁目13番６号 株式会社スピルリナ研究所内 (72)発明者 西垣 広志 大阪府大阪市淀川区西中島１丁目13番６号 株式会社スピルリナ研究所内 (72)発明者 太田 康朗 京都府京都市南区吉祥院石原上川原町37番 地 交洋ファインケミカル株式会社内 (72)発明者 小田 圭一 広島県福山市箕沖町95番地７ 池田食研株 式会社内 (72)発明者 松枝 昭治 広島県福山市箕沖町95番地７ 池田食研株 式会社内 Ｆターム(参考） 4B064 AD85 CA21 CB03 CD21 CE01 CE03 CE08 DA01 DA10 DA11 4H059 BA33 BB05 BB07 BC06 BC48 CA38 DA04 EA21 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Yasumasa Kodo 1-13-6 Nishinakajima, Yodogawa-ku, Osaka-shi, Osaka Inside Spirulina Research Laboratories Co., Ltd. (72) Hiroshi Nishigaki 1 Nishinakajima, Yodogawa-ku, Osaka-shi, Osaka No. 13-6, in Spirulina Research Laboratories Co., Ltd. (72) Inventor Yasuo Ota 37, Ishihara Kamikawaramachi, Kichijoin, Minami-ku, Kyoto, Kyoto Prefecture Within Koyo Fine Chemical Co., Ltd. No. 7 Ikeda Shokuhin Co., Ltd. (72) Inventor Shoji Matsueda 95-7 Minokicho, Fukuyama-shi, Hiroshima F-term (reference) 4B064 AD85 CA21 CB03 CD21 CE01 CE03 CE08 DA01 DA10 DA11 4H059 BA33 BB05 BB07 BC06 BC48 CA38 DA04 EA21
Claims (5)
ゼを用いた加水分解法によりドコサペンタエン酸の濃縮
されたドコサペンタエン酸含有グリセリドを製造するド
コサペンタエン酸含有グリセリドの製造方法において、
ドコサペンタエン酸を3.0％以上含有する水産油脂を原
料とすることを特徴とするドコサペンタエン酸含有グリ
セリドの製造方法。1. A method for producing docosapentaenoic acid-containing glyceride, wherein docosapentaenoic acid-containing glyceride is produced from docosapentaenoic acid-containing oil or fat by a hydrolysis method using lipase.
A method for producing a docosapentaenoic acid-containing glyceride, wherein a marine oil containing 3.0% or more of docosapentaenoic acid is used as a raw material.
コサペンタエン酸を5％以上含有することを特徴とする
請求項１記載のドコサペンタエン酸含有グリセリドの製
造方法。2. The method for producing docosapentaenoic acid-containing glyceride according to claim 1, wherein the docosapentaenoic acid-containing glyceride contains docosapentaenoic acid in an amount of 5% or more.
価が70〜170に達するまで行われることを特徴とする請
求項１記載のドコサペンタエン酸含有グリセリドの製造
方法。3. The method for producing a docosapentaenoic acid-containing glyceride according to claim 1, wherein the hydrolysis is carried out until the acid value of the hydrolyzed oil during the reaction reaches 70 to 170.
特徴とする請求項１記載のドコサペンタエン酸含有グリ
セリドの製造方法。4. The method for producing docosapentaenoic acid-containing glyceride according to claim 1, wherein the marine oil is a seal oil.
とする請求項１記載のドコサペンタエン酸含有グリセリ
ドの製造方法。5. The method for producing docosapentaenoic acid-containing glyceride according to claim 1, wherein the marine oil or fat is salmon oil.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004285182A (en) * | 2003-03-20 | 2004-10-14 | Yuji Shimada | Glyceride and its manufacturing process |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000501131A (en) * | 1995-11-24 | 2000-02-02 | ロダース・クロックラーン・ビー・ブイ | Compositions based on fish oil |
| JP2000060587A (en) * | 1998-08-27 | 2000-02-29 | Nagase Seikagaku Kogyo Kk | Production and use of new oil and fat composition |
| JP2002540221A (en) * | 1999-01-29 | 2002-11-26 | アトランティス マリン インコーポレイテッド | Process of converting refined triglycerides from marine sources into mildly stable oils |
-
2000
- 2000-09-04 JP JP2000266569A patent/JP5000035B2/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000501131A (en) * | 1995-11-24 | 2000-02-02 | ロダース・クロックラーン・ビー・ブイ | Compositions based on fish oil |
| JP2000060587A (en) * | 1998-08-27 | 2000-02-29 | Nagase Seikagaku Kogyo Kk | Production and use of new oil and fat composition |
| JP2002540221A (en) * | 1999-01-29 | 2002-11-26 | アトランティス マリン インコーポレイテッド | Process of converting refined triglycerides from marine sources into mildly stable oils |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004285182A (en) * | 2003-03-20 | 2004-10-14 | Yuji Shimada | Glyceride and its manufacturing process |
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