JP2005154422A - Powder composition of phospholipid containing highly unsaturated fatty acid - Google Patents
Powder composition of phospholipid containing highly unsaturated fatty acid Download PDFInfo
- Publication number
- JP2005154422A JP2005154422A JP2004313441A JP2004313441A JP2005154422A JP 2005154422 A JP2005154422 A JP 2005154422A JP 2004313441 A JP2004313441 A JP 2004313441A JP 2004313441 A JP2004313441 A JP 2004313441A JP 2005154422 A JP2005154422 A JP 2005154422A
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- JP
- Japan
- Prior art keywords
- fatty acid
- phospholipid
- highly unsaturated
- unsaturated fatty
- powder composition
- 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
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- 150000003904 phospholipids Chemical group 0.000 title claims abstract description 94
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 239000000843 powder Substances 0.000 title claims abstract description 53
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 44
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 27
- 229930195729 fatty acid Natural products 0.000 claims abstract description 27
- 239000000194 fatty acid Substances 0.000 claims abstract description 27
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000000470 constituent Substances 0.000 claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 18
- 241000251468 Actinopterygii Species 0.000 claims description 9
- 235000015170 shellfish Nutrition 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 23
- 238000004108 freeze drying Methods 0.000 abstract description 14
- 239000000839 emulsion Substances 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 2
- 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 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 229940090949 docosahexaenoic acid Drugs 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 9
- 238000010298 pulverizing process Methods 0.000 description 9
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 8
- 235000019688 fish Nutrition 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 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 6
- 235000014102 seafood Nutrition 0.000 description 6
- 241000238366 Cephalopoda Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 244000068988 Glycine max Species 0.000 description 5
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- 150000002632 lipids Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 235000020637 scallop Nutrition 0.000 description 5
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 4
- 241000237503 Pectinidae Species 0.000 description 4
- 244000269722 Thea sinensis Species 0.000 description 4
- 229930003427 Vitamin E Natural products 0.000 description 4
- 230000009471 action Effects 0.000 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 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 4
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 4
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 4
- 235000013402 health food Nutrition 0.000 description 4
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- 239000011709 vitamin E Substances 0.000 description 4
- 229940046009 vitamin E Drugs 0.000 description 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229940114079 arachidonic acid Drugs 0.000 description 3
- 235000021342 arachidonic acid Nutrition 0.000 description 3
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 3
- 235000005487 catechin Nutrition 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 150000002327 glycerophospholipids Chemical class 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- -1 phospholipid fatty acids Chemical class 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 210000001835 viscera Anatomy 0.000 description 3
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
- 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
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-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
- 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 description 2
- 241000972773 Aulopiformes Species 0.000 description 2
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 2
- 241000269821 Scombridae Species 0.000 description 2
- 235000006468 Thea sinensis Nutrition 0.000 description 2
- 229930003268 Vitamin C Natural products 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000013793 astaxanthin Nutrition 0.000 description 2
- 239000001168 astaxanthin Substances 0.000 description 2
- 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 description 2
- 229940022405 astaxanthin Drugs 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 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 2
- 229950001002 cianidanol Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000006185 dispersion Substances 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
- 238000001035 drying Methods 0.000 description 2
- 235000013345 egg yolk Nutrition 0.000 description 2
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- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000020640 mackerel Nutrition 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- 230000000704 physical effect Effects 0.000 description 2
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- 238000001291 vacuum drying Methods 0.000 description 2
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- 239000011718 vitamin C Substances 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 241000555825 Clupeidae Species 0.000 description 1
- 208000019505 Deglutition disease Diseases 0.000 description 1
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- 239000004278 EU approved seasoning Substances 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
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- 102000004190 Enzymes Human genes 0.000 description 1
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- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
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- 241000276438 Gadus morhua Species 0.000 description 1
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- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000237509 Patinopecten sp. Species 0.000 description 1
- 241000269908 Platichthys flesus Species 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
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- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
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- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
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- 239000011732 tocopherol Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
Landscapes
- Fats And Perfumes (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
本発明は、高度不飽和脂肪酸含有リン脂質粉体組成物に関する。 The present invention relates to a highly unsaturated fatty acid-containing phospholipid powder composition.
アラキドン酸、エイコサペンタエン酸（ＥＰＡ）、ドコサヘキサエン酸（ＤＨＡ）などの高度不飽和脂肪酸、特に、最初の二重結合がメチル期末端（ω末端）から数えて３番目の炭素にあるω−３系高度不飽和脂肪酸はその多彩な生理活性により近年、非常に注目を集めている物質である。なかでもＤＨＡは、記憶学習向上作用、網膜反射能向上作用、血圧低下作用、コレステロール低下作用などがあるとされている。従来、ＤＨＡは主に魚油から抽出されたトリグリセリド型のものが供給されており、健康食品としての市場が確立されている。ＤＨＡを構成脂肪酸として持つグリセロリン脂質（リン脂質型ＤＨＡと呼ぶ）は、経口投与した場合、トリグリセリド型ＤＨＡよりも高い生理活性を有するといわれており、リン脂質型ＤＨＡの供給が望まれている。リン脂質型ＤＨＡは魚介類などに天然の形で存在するｓｎ−２位にＤＨＡが結合したものが生理活性に大きく寄与することが知られている。 Polyunsaturated fatty acids such as arachidonic acid, eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA), especially the ω-3 system in which the first double bond is at the 3rd carbon from the methyl end (ω end) Polyunsaturated fatty acids are substances that have attracted much attention in recent years due to their various physiological activities. Among them, DHA is said to have a memory learning improving action, a retinal reflex improving action, a blood pressure lowering action, a cholesterol lowering action and the like. Conventionally, DHA is mainly supplied with a triglyceride type extracted from fish oil, and the market as a health food has been established. Glycerophospholipid (referred to as phospholipid type DHA) having DHA as a constituent fatty acid is said to have higher physiological activity than triglyceride type DHA when administered orally, and supply of phospholipid type DHA is desired. As for phospholipid type DHA, it is known that DHA bound to sn-2 position existing in a natural form in fish and shellfish and the like greatly contributes to physiological activity.
リン脂質型ＤＨＡは魚介類からの抽出法が目的物質を安価にかつ容易に製造するのに最も適した方法であるため、原料の選択、抽出法などに様々な検討が行なわれてきている。例えばＤＨＡを高濃度に含有するマグロをはじめとするカツオ、アジ、サバ、イワシ等青背の魚の頭部、腹部、内臓各部或いは全体から抽出する方法（特許文献１、特許文献２）や、ＤＨＡを培地に添加して培養した微生物菌体から抽出する方法（特許文献３）、イカの皮から抽出する方法（特許文献４、特許文献５、特許文献６）、イカミールから抽出する方法（特許文献７）などが報告されている。また、大豆レシチンや卵黄レシチンなどのリン脂質の脂肪酸を酵素を用いて高度不飽和脂肪酸に変換させて得る方法などもある。しかし、上記方法のいずれの場合も抽出物は粘稠なペースト状、もしくは粘性の非常に高いオイル状である。そのため容器や計量スプーンなどにへばり付き、非常にハンドリング性の悪いものであった。さらに、水への分散性も非常に悪く、水をベースとする化粧品、健康食品等への利用が困難であった。 Since phospholipid type DHA is the most suitable method for producing a target substance at low cost and easily by extraction from seafood, various studies have been conducted on selection of raw materials, extraction methods and the like. For example, a method of extracting from the head, abdomen, internal organs or the whole of blue-backed fish such as tuna, tuna, mackerel, sardine, etc. containing DHA in high concentration (Patent Document 1, Patent Document 2), DHA Extracted from microbial cells cultured in a culture medium (Patent Document 3), extracted from squid skin (Patent Document 4, Patent Document 5, Patent Document 6), extracted from squid meal (Patent Document 3) 7) etc. have been reported. There is also a method of obtaining phospholipid fatty acids such as soybean lecithin and egg yolk lecithin by converting them into highly unsaturated fatty acids using enzymes. However, in any of the above methods, the extract is in the form of a viscous paste or a very viscous oil. For this reason, the container and measuring spoon were attached to the screen, and the handling property was very poor. Furthermore, the dispersibility in water is very poor, making it difficult to use in water-based cosmetics, health foods, and the like.
一方、ハンドリング性の改善のために、デキストリンのような賦形剤を加えての粉末化は一般的に知られているが、賦形剤という不純物を加えているのに他ならないので加えずに済むなら、それに越したことはない。リン脂質を賦形剤などを用いずに粉末化する方法として、大豆や卵黄レシチンの水懸濁液を凍結乾燥して粉体化する技術が開示されている。（特許文献８、特許文献９）しかし、魚介類から抽出したリン脂質は大豆や卵黄に比べて高度不飽和脂肪酸の含量が高いため、同様に凍結乾燥しても仕上がりにムラがあり、粘稠で水分散性の悪いものしか得られなかった。大豆や卵黄レシチンは高度不飽和脂肪酸をほとんど含まないため、大豆等のレシチンの粉末と、高度不飽和脂肪酸を構成成分として持つリン脂質の粉体組成物とでは全く性質が違うものであるためであろう。また、レシチンに関しては水分散性を向上させる技術がいくつか報告されている（特許文献１０、特許文献１１）。しかし、例えば特許文献１１ではレシチンの他にキサンタンガムのような水溶性高分子を加えて初めて安定な水分散を可能としている。また、粉体化の例から分かるように、高度不飽和脂肪酸を多く含む魚介類由来のリン脂質と、卵黄や大豆由来のリン脂質とは本質的に違う性質を持つものであるため、レシチンの技術をそのまま使えるものではない。つまり、第３成分を加えることなく、水分散性の良好な高度不飽和脂肪酸を構成脂肪酸として持つリン脂質粉体組成物については未だ何ら報告されていない。そのため、ハンドリングが容易で水への分散がスムーズな高度不飽和脂肪酸を構成脂肪酸として持つリン脂質粉体組成物が強く望まれていた。
本発明は、賦形剤を使わずに、水への分散性が良くハンドリング性の良好な高度不飽和脂肪酸含有リン脂質粉体組成物を提供することを目的とする。 An object of the present invention is to provide a highly unsaturated fatty acid-containing phospholipid powder composition having good dispersibility in water and good handling properties without using an excipient.
本発明者らは、上記課題を解決するため鋭意検討した結果、特定の溶剤の系で凍結乾燥をおこなうことにより、驚くべきことに賦形剤を用いずにハンドリングが容易でかつ水への分散性が良い高度不飽和脂肪酸含有リン脂質粉体組成物が得られることを見出し、本発明をなすに至った。 As a result of intensive studies to solve the above problems, the present inventors have surprisingly been able to handle easily without using excipients and disperse in water by performing lyophilization in a specific solvent system. The present inventors have found that a highly unsaturated fatty acid-containing phospholipid powder composition having good properties can be obtained, and have made the present invention.
すなわち、本発明は下記のとおりである。
（１）嵩密度が０．５０ｇ／ｃｍ３以下であり、呼び寸法９．５２ｍｍの篩を通過しない成分が２０質量％以下であり、水分率が０．０１〜１０質量％である粉体であることを特徴とする高度不飽和脂肪酸を構成脂肪酸として持つリン脂質の粉体組成物。
（２）含有するリン脂質の全構成脂肪酸の総量の２０質量％以上が高度不飽和脂肪酸であることを特徴とする前記（１）記載の高度不飽和脂肪酸を構成脂肪酸として持つリン脂質の粉体組成物。
（３）リン脂質が魚介類の組織から抽出したものであることを特徴とする前記（１）または（２）に記載の高度不飽和脂肪酸を構成脂肪酸として持つリン脂質の粉体組成物。
（４）高度不飽和脂肪酸を構成脂肪酸として持つリン脂質を含む水／アルコール溶液もしくは懸濁液を凍結乾燥する工程を含むことを特徴とする前記（１）〜（３）のいずれか一項に記載の高度不飽和脂肪酸を構成脂肪酸として持つリン脂質の粉体組成物の製造方法。
（５）前記（１）〜（３）のいずれか一項に記載の高度不飽和脂肪酸を構成脂肪酸として持つリン脂質の粉体組成物を添加したことを特徴とする食品。
That is, the present invention is as follows.
(1) A powder having a bulk density of 0.50 g / cm 3 or less, a component not passing through a sieve having a nominal size of 9.52 mm, 20% by mass or less, and a moisture content of 0.01 to 10% by mass. A powder composition of a phospholipid having a highly unsaturated fatty acid as a constituent fatty acid.
(2) A phospholipid powder having a highly unsaturated fatty acid as a constituent fatty acid according to (1), wherein 20% by mass or more of the total amount of all the constituent fatty acids of the phospholipid contained is a highly unsaturated fatty acid. Composition.
(3) The phospholipid powder composition having a highly unsaturated fatty acid as a constituent fatty acid according to (1) or (2), wherein the phospholipid is extracted from a fish and shellfish tissue.
(4) The method according to any one of (1) to (3) above, comprising a step of freeze-drying a water / alcohol solution or suspension containing a phospholipid having a highly unsaturated fatty acid as a constituent fatty acid. A process for producing a powder composition of a phospholipid having the described highly unsaturated fatty acid as a constituent fatty acid.
(5) A food comprising a phospholipid powder composition having the polyunsaturated fatty acid according to any one of (1) to (3) as a constituent fatty acid.
以下、本発明について、特にその好ましい態様を具体的に説明する。
本発明でいう高度不飽和脂肪酸を構成脂肪酸として持つリン脂質（高度不飽和脂肪酸含有リン脂質という。）とは、グリセロリン脂質の持つ２つの脂肪酸残基の１つもしくは２つが高度不飽和脂肪酸残基であるリン脂質を含むリン脂質のことをいい、高度不飽和脂肪酸を構成成分として持たないリン脂質が含まれていても構わない。グリセロリン脂質としては、例えばフォスファジルコリン、フォスファジルセリン、フォスファジルイノシトール、フォスファジルエタノールアミン、フォスファジルグリセロール、フォスファジン酸などが挙げられる。これらの単独でも混合物でも構わない。もちろん、スフィンゴリン脂質やプラスマローゲン型リン脂質、各リン脂質のリゾ体など、天然物がもともと保持している他の種類のリン脂質や糖脂質が含まれていても構わない。高度不飽和脂肪酸としては、例えばドコサヘキサエン酸（ＤＨＡ）やエイコサペンタエン酸（ＥＰＡ）、アラキドン酸（ＡＡ）などがある。高度不飽和脂肪酸含有リン脂質は、その構成成分である脂肪酸組成中に、構成脂肪酸の総量に対し高度不飽和脂肪酸が２０質量％以上であることが好ましい。より好ましくは４０％質量以上である。魚介類などから抽出した高度不飽和脂肪酸を多量に含むリン脂質に、高度不飽和脂肪酸をほとんど含まない大豆レシチンや卵黄レシチン等のリン脂質を加えたものも、本発明の高度不飽和脂肪酸含有リン脂質に含まれるが、合計の全脂肪酸組成中の高度不飽和脂肪酸が２０質量％未満では高度不飽和脂肪酸の生理活性効果が得られにくいので、２０質量％以上であることが好ましい。
The preferred embodiments of the present invention will be specifically described below.
The phospholipid having highly unsaturated fatty acid as a constituent fatty acid in the present invention (referred to as highly unsaturated fatty acid-containing phospholipid) means that one or two of the two fatty acid residues of glycerophospholipid are highly unsaturated fatty acid residues. The phospholipid containing the phospholipid which is and may contain the phospholipid which does not have a highly unsaturated fatty acid as a structural component. Examples of the glycerophospholipid include phosphadylcholine, phosphadylserine, phosphadylinositol, phosphadylethanolamine, phosphadylglycerol, and phosphadic acid. These may be used alone or as a mixture. Of course, other types of phospholipids and glycolipids originally held by natural products such as sphingophospholipids, plasmalogen-type phospholipids, and lyso forms of each phospholipid may be contained. Examples of highly unsaturated fatty acids include docosahexaenoic acid (DHA), eicosapentaenoic acid (EPA), and arachidonic acid (AA). The polyunsaturated fatty acid-containing phospholipid preferably has a polyunsaturated fatty acid content of 20% by mass or more based on the total amount of the constituent fatty acids in the fatty acid composition as a constituent component. More preferably, it is 40% mass or more. A phospholipid containing a large amount of a highly unsaturated fatty acid extracted from seafood or the like and a phospholipid such as soy lecithin or egg yolk lecithin that hardly contains a highly unsaturated fatty acid is also added. Although it is contained in lipid, if the polyunsaturated fatty acid in the total fatty acid composition is less than 20% by mass, it is difficult to obtain the bioactive effect of polyunsaturated fatty acid.
本発明のいう高度不飽和脂肪酸含有リン脂質は主に魚介類の組織から抽出することにより得られる。魚介類の組織とは高度不飽和脂肪酸含有リン脂質を含むものなら魚介類の内臓や皮などの一部でも良いし、それらの集合体である個体そのものでも構わない。また卵などでも構わない。これらを単独もしくは複数組み合わせて使うことが出来る。特に、魚介類の組織の中でも比較的、高度不飽和脂肪酸含有リン脂質の含量の多いものが好ましい。例えば、イカ皮やイカ、ホタテ、マグロ、イワシ、カツオ、サバ、タラ、サケ、タイ、ヒラメ、サメ、マスなどの内臓やタラコ、イクラなどの魚卵が挙げられる。特にホタテの内臓は、通称ウロと呼ばれており大量に廃棄されている。ウロとはホタテの軟体部の貝柱以外の部分全体（中腸線、生殖腺、ヒモ）を広義のウロ、中腸腺のみを狭義のウロといい、単純にウロといった場合、どちらを指すかは明確ではない。本発明では狭義のウロでも、広義のウロでも、その混合物でも構わない。ウロは安価に入手可能なため原料として好ましい。魚介類の組織からのリン脂質組成物の抽出は例えば特開平０６−３２１９７０号公報に記載の方法等、公知の方法に従って行なえば良い。 The polyunsaturated fatty acid-containing phospholipids referred to in the present invention are obtained mainly by extraction from fish and shellfish tissues. The seafood tissue may be a part of the internal organs or skin of the seafood as long as it contains a highly unsaturated fatty acid-containing phospholipid, or it may be an individual itself as an aggregate thereof. Eggs are also acceptable. These can be used alone or in combination. In particular, a relatively high content of highly unsaturated fatty acid-containing phospholipid is preferable among fish and shellfish tissues. Examples include squid skin, squid, scallops, tuna, sardines, bonito, mackerel, cod, salmon, Thai, flounder, shark, trout, etc. and fish eggs such as octopus and salmon. In particular, the internal organs of scallops are commonly called uro and are discarded in large quantities. The term uro is called uro in the broad sense when the whole part of the scallop soft body other than the scallops (midgut, gonad, string) is called uro in the narrow sense. Absent. In the present invention, uro in a narrow sense, uro in a broad sense, or a mixture thereof may be used. Uro is preferred as a raw material because it is available at low cost. The extraction of the phospholipid composition from the seafood tissue may be performed according to a known method such as the method described in JP-A-06-321970.
本発明でいう高度不飽和脂肪酸含有リン脂質の粉体組成物とは上記の高度不飽和脂肪酸含有リン脂質にリン脂質以外のもの、例えば抗酸化剤やトリグリセライド等が入った組成物でも構わない。もちろん高度不飽和脂肪酸含有リン脂質以外のものが何も含まれない場合も、本発明のいう高度不飽和脂肪酸含有リン脂質の粉体組成物には含まれる。本発明では賦形剤を用いず、高濃度の高度不飽和脂肪酸含有リン脂質が得られるところに最大の効果があるので、組成物中のリン脂質含量が７０質量％以上が好ましく、より好ましくは８５質量％以上である。リン脂質以外に含まれるものとしては、例えば、トコフェロール類およびトコトリエノール類（ビタミンＥ）、アスコルビン酸（ビタミンＣ）やアスタキサンチンのようなカロチノイド系色素、茶カテキンなどの抗酸化作用のある物質が単独もしくは複数含まれているとより一層の抗酸化性が期待できるため好ましい。 The powder composition of the highly unsaturated fatty acid-containing phospholipid referred to in the present invention may be a composition containing the above-mentioned highly unsaturated fatty acid-containing phospholipid other than phospholipid, such as an antioxidant or triglyceride. Of course, even when nothing other than the highly unsaturated fatty acid-containing phospholipid is contained, it is included in the powder composition of the highly unsaturated fatty acid-containing phospholipid as referred to in the present invention. In the present invention, since the maximum effect is obtained where a high concentration of highly unsaturated fatty acid-containing phospholipid is obtained without using an excipient, the phospholipid content in the composition is preferably 70% by mass or more, more preferably It is 85 mass% or more. Examples of substances other than phospholipids include tocopherols and tocotrienols (vitamin E), carotenoid pigments such as ascorbic acid (vitamin C) and astaxanthin, and substances having an antioxidative activity such as tea catechins alone or It is preferable to contain a plurality of antioxidants since more antioxidant properties can be expected.
賦形剤を含まない高度不飽和脂肪酸含有リン脂質組成物を単純に乾燥するだけでは粘稠なペースト状のものになってしまうため、本発明のハンドリング性の良好な高度不飽和脂肪酸含有リン脂質粉体組成物は、従来の技術では得ることは極めて困難である。本発明のリン脂質粉体組成物を得るには水／アルコール溶液、または懸濁液での凍結乾燥法を用いる。 Since a highly unsaturated fatty acid-containing phospholipid composition containing no excipients becomes a viscous paste simply by drying, the highly unsaturated fatty acid-containing phospholipid of the present invention has good handleability. The powder composition is extremely difficult to obtain by conventional techniques. In order to obtain the phospholipid powder composition of the present invention, a freeze-drying method using a water / alcohol solution or suspension is used.
用いるアルコールとしては、メタノール、エタノール、イソプロピルアルコールなどが挙げられるが、安全性の観点からエタノールが好ましい。具体的には水とエタノールの混合溶媒による凍結乾燥を行なうことにより粉末状もしくは粉体状に粉砕可能な固形物を得ることが可能である。この場合のリン脂質組成物の濃度は凍結乾燥前の組成物全体の重量に対して５〜６０質量％であることが好ましい。より好ましくは１５〜３０質量％である。エタノールは凍結乾燥前の組成物全体の重量に対して０．１〜３０質量％であり、好ましくは５〜１５質量％である。水はリン脂質とエタノールの濃度が前記範囲になる量に調整することが好ましい。また、水を加える際にリン脂質組成物が析出し沈殿してしまう場合があるので良く攪拌を行ない均一に分散させる操作をおこなうことが好ましい。また、リン脂質組成物をあらかじめヘキサン等に溶解しておき、そこに水とエタノールを加えてゆっくりと溶媒を留去することによっても均一のエマルションを得ることが可能である。 Examples of the alcohol to be used include methanol, ethanol, isopropyl alcohol and the like, and ethanol is preferable from the viewpoint of safety. Specifically, it is possible to obtain a solid that can be pulverized into a powder or a powder by freeze-drying with a mixed solvent of water and ethanol. In this case, the concentration of the phospholipid composition is preferably 5 to 60% by mass with respect to the total weight of the composition before lyophilization. More preferably, it is 15-30 mass%. Ethanol is 0.1-30 mass% with respect to the weight of the whole composition before lyophilization, Preferably it is 5-15 mass%. It is preferable to adjust water so that the concentration of phospholipid and ethanol is within the above range. Moreover, when adding water, since a phospholipid composition may precipitate and precipitate, it is preferable to perform an operation of stirring well and dispersing uniformly. It is also possible to obtain a uniform emulsion by previously dissolving the phospholipid composition in hexane or the like, adding water and ethanol thereto and slowly distilling off the solvent.
凍結乾燥は真空ポンプの減圧度に応じて適宜、温度条件を定めればよいが、乾燥初期の段階は出来るだけ低温を維持することが好ましい。例えば、−３０℃で一晩凍結した後、凍結乾燥機の棚温を３０℃で２時間、３０℃から６０℃へ２時間かけて昇温し、そのまま６０℃で１４時間。その後、５時間かけて３０℃まで降温し、その後、３０℃で１２時間という温度条件で乾燥を行なえばよい。凍結乾燥後の水分率は０．１〜１０質量％であれば良いが、好ましくは０．１〜３質量％、より好ましくは０．１〜１質量％である。 For freeze-drying, the temperature condition may be determined as appropriate according to the degree of pressure reduction of the vacuum pump. For example, after freezing at −30 ° C. overnight, the shelf temperature of the freeze dryer is increased at 30 ° C. for 2 hours, from 30 ° C. to 60 ° C. over 2 hours, and then directly at 60 ° C. for 14 hours. Thereafter, the temperature is lowered to 30 ° C. over 5 hours, and then dried at 30 ° C. for 12 hours. The moisture content after lyophilization may be 0.1 to 10% by mass, preferably 0.1 to 3% by mass, and more preferably 0.1 to 1% by mass.
凍結乾燥で得られた乾燥物は、粉末状に粉砕可能な固形物となる。粉末状に粉砕可能な固形物とは、スクリーンミル、パワーミルや乳鉢など一般的な粉砕方法で比較的容易に、流動性のある粉体に加工することが可能な形状・力学物性を有するの物のことを言う。これに対し、従来の魚介類由来のリン脂質組成物はガム状であり、乳鉢などにへばりつきやすいため一般的な粉砕方法による分体化はきわめて困難である。 The dried product obtained by lyophilization becomes a solid that can be pulverized into a powder. Solids that can be pulverized into powders are those that have shapes and mechanical properties that can be processed into fluid powders relatively easily by general pulverization methods such as screen mills, power mills, and mortars. Say that. On the other hand, the conventional fish and shellfish-derived phospholipid composition is gum-like and easily sticks to a mortar or the like, so that it is very difficult to separate by a general grinding method.
本発明の凍結乾燥で得られた乾燥物は、例えば、パワーミル、ジェットミル、振動ミル、スクリーンミル、乳鉢など、一般的な粉砕方法を用いて粉砕すれば良い。粉砕後の粉末は呼び寸法９．５２ｍｍの篩を通過しない成分が２０質量％以下の範囲にあると、水への分散性およびハンドリング性が良好であるため好ましい。より好ましくは５質量％以下である。呼び寸法１．４０ｍｍの篩を通過する成分が８０質量％以上あると、流動性が向上するため、さらに好ましい。篩の呼び寸法はＪＩＳ Ｚ ８８０１（ＩＳＯ ３３１０）に準拠したものを指す。粉砕は室温でも可能であるが、脂質成分は暖めると粘着性が出る性質を有するので出来るだけ低温の雰囲気下で行なうのが好ましい。作業性やコストの観点から０℃前後が好ましい。また、凍結乾燥品は吸湿しやすいので、湿度の低い雰囲気下で出来るだけ素早く粉砕し、粉砕後はアルミ袋などに密封遮光保存することが望ましい。上記手法によって得られるリン脂質粉体組成物の嵩密度は０．５０ｇ／ｃｍ３以下が良い。好ましくは０．３５ｇ／ｃｍ３以下であり、より好ましくは０．２０ｇ／ｃｍ３以下である。嵩密度０．５０ｇ／ｃｍ３以下とすることにより水への分散性が良くなる。 What is necessary is just to grind | pulverize the dried material obtained by freeze-drying of this invention using common grinding | pulverization methods, such as a power mill, a jet mill, a vibration mill, a screen mill, and a mortar, for example. The pulverized powder preferably has a component that does not pass through a sieve having a nominal size of 9.52 mm in a range of 20% by mass or less because dispersibility in water and handling properties are good. More preferably, it is 5 mass% or less. It is more preferable that the amount of the component that passes through a sieve having a nominal size of 1.40 mm is 80% by mass or more because fluidity is improved. The nominal size of the sieve refers to that according to JIS Z 8801 (ISO 3310). Although pulverization can be performed at room temperature, it is preferable to perform the pulverization in an atmosphere as low as possible since the lipid component has a property of becoming sticky when heated. From the viewpoint of workability and cost, around 0 ° C. is preferable. In addition, since freeze-dried products are easy to absorb moisture, it is desirable to grind them as quickly as possible in a low humidity atmosphere, and after crushing, store them in an aluminum bag or the like in a light-shielded manner. The bulk density of the phospholipid powder composition obtained by the above method is preferably 0.50 g / cm 3 or less. Preferably it is 0.35 g / cm 3 or less, more preferably 0.20 g / cm 3 or less. By setting the bulk density to 0.50 g / cm 3 or less, the dispersibility in water is improved.
上記方法にて得られる本発明のリン脂質粉末組成物の利点のひとつは、その良好な水分散性にある。通常、リン脂質組成物は脂溶性のため、水には不溶である。また従来の多価不飽和脂肪酸含有リン脂質組成物は粘稠なペースト状、もしくはオイル状であるため非常に分散が困難である。このため従来はリン脂質組成物を水中に均一に分散させるには乳化剤などを用いたり、ホモジナイザーなどで激しく攪拌をする必要があった。一方、当発明により粉末化した高度不飽和脂肪酸含有リン脂質粉体組成物は水に加えて軽く攪拌するだけで、乳化剤を用いずに分散させることが可能である。この水への分散性の良さから水系の用途への展開がより容易となる。また、粉体状でハンドリング性が良好なため、様々な用途への使用が可能となる。ここでいうハンドリング性とは、流動性および混合均一性のことを言う。例えば、粉体の安息角が６０度以下であることや、Ｖ型ブレンダーを用いて粉体混合を行なった場合に混合均一性が良好なことなどが挙げられる。従来技術で得られるリン脂質組成物は粘性が高く安息角は測定さえ困難であり、混合均一性も非常に悪かった。 One of the advantages of the phospholipid powder composition of the present invention obtained by the above method is its good water dispersibility. Usually, phospholipid compositions are insoluble in water because they are fat-soluble. Further, the conventional polyunsaturated fatty acid-containing phospholipid composition is very difficult to disperse because it is in the form of a viscous paste or oil. For this reason, conventionally, in order to uniformly disperse the phospholipid composition in water, it has been necessary to use an emulsifier or the like, or to vigorously stir with a homogenizer or the like. On the other hand, the highly unsaturated fatty acid-containing phospholipid powder composition pulverized according to the present invention can be dispersed without using an emulsifier only by stirring lightly in addition to water. This good dispersibility in water makes it easier to deploy to water-based applications. Moreover, since it is powdery and has good handleability, it can be used for various purposes. The handling property here means fluidity and mixing uniformity. For example, the angle of repose of the powder is 60 degrees or less, and the mixing uniformity is good when the powder is mixed using a V-type blender. The phospholipid composition obtained by the prior art has a high viscosity and the angle of repose is difficult to measure, and the mixing uniformity is very poor.
本発明により、水への分散性も良く、流動性および混合均一性が良好な高度不飽和脂肪酸含有リン脂質粉体組成物が得られるため、様々な用途への使用が考えられる。例えば散剤、顆粒剤、錠剤、糖衣剤、カプセル剤、ピル、液剤、アンプル剤、注射剤などの薬剤の形態やサプリメント剤として用いることが出来る。また、ハンドリング性が向上しているため一般食品や健康食品に添加しての利用がしやすくなる。例えば、緑茶飲料、紅茶飲料、半発酵茶飲料（ウーロン茶など）、コーヒー飲料、乳飲料、豆乳、清涼飲料水、スポーツドリンク、果汁飲料、乳酸菌飲料、野菜ジュース、ドリンク剤、アルコール飲料などのような飲料や、ゼリー状食品、スープ、ドレッシング、ふりかけ、パン、ラーメン、うどん、そば、プリン、ゼリー、スナック菓子、ケーキ、饅頭、羊羹、ういろう、おにぎり、ガム、キャンディー、チョコレート、クッキー、キャラメル、アイスクリーム、ソフトクリーム、マヨネーズ、マーガリン、調味料、またヨーグルトのような乳製品などにも用いることが出来る。本発明の成分は人体にとって極めて有用な成分であるため嚥下障害をもつ人のための流動食への添加や、宇宙食への添加など、脂質成分の栄養補助として加えることも出来る。さらに、多価不飽和脂肪酸含有リン脂質は、美白作用なども持つと言われており、香粧品への配合も可能である。例えば美白剤、保湿剤、日焼け止め、ファンデーション、口紅、リップクリーム、メイク落とし、シャンプー、リンス、ヘアーカラー、白髪染め、石鹸などへの配合が考えられる。 According to the present invention, a highly unsaturated fatty acid-containing phospholipid powder composition having good dispersibility in water and good fluidity and mixing uniformity can be obtained. Therefore, it can be used in various applications. For example, it can be used as a powder form, a granule, a tablet, a sugar coating, a capsule, a pill, a liquid, an ampoule, an injection, and the like, and as a supplement. Moreover, since handling property is improved, it becomes easy to use by adding to general foods and health foods. For example, green tea drinks, black tea drinks, semi-fermented tea drinks (such as oolong tea), coffee drinks, milk drinks, soy milk, soft drinks, sports drinks, fruit juice drinks, lactic acid bacteria drinks, vegetable juices, drinks, alcoholic drinks, etc. Beverages, jelly-like foods, soups, dressings, sprinkles, bread, ramen, udon, soba, pudding, jelly, snacks, cakes, buns, sheepskins, owls, rice balls, gum, candy, chocolate, cookies, caramel, ice cream, It can also be used in soft cream, mayonnaise, margarine, seasonings, and dairy products such as yogurt. Since the components of the present invention are extremely useful for the human body, they can also be added as a nutritional supplement for lipid components such as addition to liquid foods for people with dysphagia and addition to space foods. Furthermore, polyunsaturated fatty acid-containing phospholipids are said to have a whitening effect and can be incorporated into cosmetics. For example, it can be formulated into a whitening agent, moisturizing agent, sunscreen, foundation, lipstick, lip balm, makeup remover, shampoo, rinse, hair color, gray hair dye, soap, and the like.
製剤化、食品化、香粧品への配合の手法においては、それぞれの形態の製造上許容しうる希釈剤などの他の成分が一つ、もしくは複数含まれる混合物として含有されても構わない。他の成分としては、例えば、デンプンやセルロースのような賦形剤、希釈剤、担体、ビタミンＥ、ビタミンＣ、カテキン、アスタキサンチンなどの抗酸化剤、増量剤、結合剤、潤滑剤、崩壊剤、界面活性剤、分散剤、緩衝剤、矯味剤、矯臭剤、香料、保存剤などが考えられるが、これらに限定されるものではない。 In the methods of formulating, formulating foods, and blending into cosmetics, other components such as diluents acceptable in the production of each form may be contained as one or a mixture containing a plurality thereof. Other ingredients include, for example, excipients such as starch and cellulose, diluents, carriers, antioxidants such as vitamin E, vitamin C, catechin, and astaxanthin, extenders, binders, lubricants, disintegrants, Surfactants, dispersants, buffers, flavoring agents, flavoring agents, fragrances, preservatives and the like can be considered, but are not limited thereto.
以下に本発明の実施例を説明するが、本発明は以下の例によってなんら限定されるものではない。なお実施例、比較例に記載した物性評価に関する手法は以下の通りである。物性の評価は室温２５℃、相対湿度５５％の恒温室で行なった。 Examples of the present invention will be described below, but the present invention is not limited to the following examples. The methods related to the physical property evaluation described in the examples and comparative examples are as follows. The physical properties were evaluated in a constant temperature room at 25 ° C. and a relative humidity of 55%.
［リン脂質の含量、高度不飽和脂肪酸含量］
リン脂質の含量は、基準油脂分析試験法４．３．１に準じて、高度不飽和脂肪酸含量は基準油脂分析試験法のメチルエステル化法に準じて分析した。
[Phospholipid content, polyunsaturated fatty acid content]
The phospholipid content was analyzed according to the standard fat analysis method 4.3.1, and the highly unsaturated fatty acid content was analyzed according to the methyl esterification method of the standard fat analysis method.
［水への分散性］
水への分散性は１００ｍｌの水を入れたサンプル瓶に試料のリン脂質組成物０．１ｇを加えて蓋をして、手で激しく上下に２０回振った後の様子を目視で観察した。分散性が非常に良い場合は均一に分散するが、悪い場合は固まりのままで残ったり、壁に付着したりしていた。
[Dispersibility in water]
The dispersibility in water was visually observed after adding 0.1 g of the phospholipid composition of the sample to a sample bottle containing 100 ml of water, capping it, and shaking it up and down 20 times by hand. When the dispersibility was very good, it was uniformly dispersed, but when it was bad, it remained agglomerated or adhered to the wall.
［嵩密度の測定］
スコットボリュメーター（ＶＷＲ ＳＣＩＥＮＴＩＦＩＣ製）を用いて２回測定してその平均値から嵩密度を求めた。
[Measurement of bulk density]
The bulk density was calculated | required from the average value by measuring twice using the Scott volume meter (made by VWR SCIENTIFIC).
［水分の測定］
基準油脂分析法４．１．１．２に準じて行った。
[Measurement of moisture]
The analysis was performed in accordance with the standard fat analysis method 4.1.1.2.
［安息角の測定］
杉原式動的安息角測定装置を用いて測定した。フィーダーはＭＩＣＲＯ ＶＩＢＲＡＴＩＮＧ ＦＥＤＥＲ（筒井理科化学製）のを用いた。フィード速度は２４ｇ／分で行なった。
[Measurement of repose angle]
It measured using the Sugihara type dynamic repose angle measuring device. The feeder used was MICRO VIBRATING FEDER (manufactured by Tsutsui Science and Chemical). The feed rate was 24 g / min.
［粉末の大きさ］
各サイズのＪＩＳ規格の篩を用いて、分級を行なった。分級は篩振とう器（ＪＩＳ Ｋ ００６９準拠）を用いて５分間振とうした。
[Powder size]
Classification was performed using a JIS standard sieve of each size. Classification was carried out for 5 minutes using a sieve shaker (conforming to JIS K 0069).
［薬物の混合粉体のサンプリング方法］
混合粉体を、その他の添加剤と混合する工程において、粉体試料採取器（筒井理科化学製。サンプル容量０．８ｍｌ）を使用し、混合機としてＶ型ブレンダ−（ＭＩＸ ＷＥＬＬ ＢＵＫＥＮＤＥＲ Ｖ−５、ＴＯＫＵＪＵ製）を用いた。混合後５分後に混合機を停止して、所定の３箇所から３点ずつ、計９点サンプリングを行なった。
[Damping method of drug mixed powder]
In the step of mixing the mixed powder with other additives, a powder sampler (manufactured by Tsutsui Science Chemical Co., Ltd., sample volume 0.8 ml) is used, and a V-type blender (MIX WELL BUKENDER V-5) is used as a mixer. , Manufactured by TOKUJU). Five minutes after mixing, the mixer was stopped, and sampling was performed for a total of 9 points, 3 points each from 3 predetermined points.
［含量均一性の評価方法］
混合粉体を評価する場合、上記、混合粉体サンプル法により採取した９個の試料各々のリン脂質の濃度を測定し、それらの測定値の標準偏差および平均値より、（標準偏差／平均値）×１００で定義される変動係数（％）から混合均一性を評価した。変動係数が低いほど含量均一性が高い。
[Method for evaluating content uniformity]
When evaluating the mixed powder, the phospholipid concentration of each of the nine samples collected by the mixed powder sample method is measured, and from the standard deviation and average value of the measured values, (standard deviation / average value) ) Mixing uniformity was evaluated from the coefficient of variation (%) defined by × 100. The lower the coefficient of variation, the higher the content uniformity.
［実施例１、比較例１］
ボイルしたホタテの広義ウロ２５００ｋｇから脂溶性成分を抽出した後、溶媒を留去して抽出粗油４１ｋｇを得た。その粗抽出油をヘキサン８０Ｌに溶かし、５０質量％アセトン水溶液１６０Ｌで有機相を洗浄した。有機相のヘキサンを留去し、その残留物を冷アセトン４００Ｌで１回、３０Ｌで２回の計３回洗浄して中性脂質を取り除き、洗浄された残留物より、残留アセトンを留去して高度不飽和脂肪酸含有リン脂質を２５．９ｋｇ得た。得られたリン脂質２０ｋｇにビタミンＥ６０ｇ、エタノール１０ｋｇ、水７０ｋｇを加えて攪拌した後、凍結乾燥して固形物を得た。固形物中のリン脂質含有量は９０質量％、高度不飽和脂肪酸含有量はリン脂質の構成脂肪酸に対して２９質量％であった。得られた固形物を小型粉砕機で粉砕して目的とする、流動性のある粉末状の高度不飽和脂肪酸含有リン脂質粉体組成物を得た。嵩密度は０．１５５ｇ／ｃｍ３、水分は０．２質量％であった。この粉末組成物は呼び寸法１．４０ｍｍの篩を９４．６質量％、４２５μｍの篩を２９．０質量％通過した。また、この粉体の安息角は５０．５度であった。
[Example 1, Comparative Example 1]
After extracting a fat-soluble component from 2500 kg of broad urine of boiled scallops, the solvent was distilled off to obtain 41 kg of extracted crude oil. The crude extracted oil was dissolved in 80 L of hexane, and the organic phase was washed with 160 L of 50 mass% acetone aqueous solution. The organic phase of hexane was distilled off, and the residue was washed three times, once with 400 L of cold acetone and twice with 30 L to remove neutral lipid, and the residual acetone was distilled off from the washed residue. As a result, 25.9 kg of highly unsaturated fatty acid-containing phospholipid was obtained. 60 g of vitamin E, 10 kg of ethanol and 70 kg of water were added to 20 kg of the obtained phospholipid and stirred, and then freeze-dried to obtain a solid. The phospholipid content in the solid was 90% by mass, and the highly unsaturated fatty acid content was 29% by mass relative to the constituent fatty acids of the phospholipid. The obtained solid was pulverized with a small pulverizer to obtain a desired powdery polyunsaturated fatty acid-containing phospholipid powder composition having fluidity. The bulk density was 0.155 g / cm 3 and the water content was 0.2% by mass. This powder composition passed 94.6% by mass of a sieve having a nominal size of 1.40 mm and 29.0% by mass of a sieve having a 425 μm size. The repose angle of this powder was 50.5 degrees.
比較例１では実施例１の凍結乾燥の代わりに真空乾燥を行なった。一旦乾燥を止めて水分を測定したところ、水分が１２質量％残っており、粉体とは程遠いオイル状であったため、更に真空乾燥を継続した。その結果、得られたものは粘稠なペースト状であり嵩密度は１．０３ｇ／ｃｍ３であった。粘稠であり呼び寸法９．５２ｍｍの篩を通過しない成分が５２．３質量％であった。安息角はフィーダーで送ることが出来ず測定不能であった。 In Comparative Example 1, vacuum drying was performed instead of freeze-drying in Example 1. Once the drying was stopped and the water content was measured, 12% by mass of water remained, and it was in the form of an oil far from the powder, so vacuum drying was further continued. As a result, the obtained product was a viscous paste and the bulk density was 1.03 g / cm 3 . The component that was viscous and did not pass through a sieve having a nominal size of 9.52 mm was 52.3% by mass. The angle of repose could not be measured because it could not be sent by the feeder.
実施例１は水への分散性が極めて良く容易に分散液となった。一方、比較例１は大部分のリン脂質が壁に付着してしまい分散しなかった。
また、それぞれのリン脂質３０ｇに市販の脱脂粉乳２０００ｇを測り取り、それぞれＶ型混合機で混合した。リン脂質の濃度の変動係数は実施例１で５．８、比較例１では７６．５であった。
In Example 1, the dispersibility in water was very good and a dispersion was easily obtained. On the other hand, in Comparative Example 1, most of the phospholipid adhered to the wall and was not dispersed.
Moreover, 2000 g of commercially available skim milk powder was measured to 30 g of each phospholipid, and each was mixed with the V-type mixer. The variation coefficient of the phospholipid concentration was 5.8 in Example 1 and 76.5 in Comparative Example 1.
［実施例２、比較例２］
イカの皮１０００ｋｇを真空乾燥して乾燥皮を３２０ｋｇ得た。この乾燥皮からエタノールとヘキサンの１対１体積比の混合溶媒６００Ｌで２回抽出し溶媒を留去した。その粗抽出油をヘキサン１００Ｌに溶かし、５０質量％アセトン水溶液２００Ｌで有機相を洗浄した。有機相を分離してヘキサンを留去した。その残留物を冷アセトン３００Ｌで１回、３０Ｌで１回の計２回洗浄して中性脂質を取り除き、洗浄された残留物から、残留アセトンを留去して高度不飽和脂肪酸含有リン脂質を１３．２ｋｇを得た。得られたリン脂質１５０ｇにビタミンＥ０．４ｇ、エタノール１００ｇ、水を７５０ｇ加えて均一なエマルションになるまで攪拌した後、凍結乾燥を行なった。それをパワーミルで粉砕してリン脂質の粉体組成物を得た。粉体組成物中のリン脂質含量は８５質量％、高度不飽和脂肪酸含量はリン脂質の構成脂肪酸に対して４１質量％であった。嵩密度は０．１４４ｇ／ｃｍ３、水分は２質量％であった。この粉体組成物は呼び寸法１．４０ｍｍの篩を９０．１質量％、４２５μｍの篩を３．３質量％通過した。この粉体の安息角は５１度であった。
[Example 2, Comparative Example 2]
1000 kg of squid skin was vacuum dried to obtain 320 kg of dried skin. This dry peel was extracted twice with 600 L of a mixed solvent of ethanol and hexane in a 1: 1 volume ratio, and the solvent was distilled off. The crude extracted oil was dissolved in 100 L of hexane, and the organic phase was washed with 200 L of 50% by mass acetone aqueous solution. The organic phase was separated and hexane was distilled off. The residue was washed twice with 300 L of cold acetone once and once with 30 L to remove neutral lipids, and the residual acetone was distilled off from the washed residue to remove highly unsaturated fatty acid-containing phospholipids. 13.2 kg was obtained. To 150 g of the obtained phospholipid, 0.4 g of vitamin E, 100 g of ethanol and 750 g of water were added and stirred until a uniform emulsion was obtained, followed by lyophilization. It was pulverized with a power mill to obtain a phospholipid powder composition. The phospholipid content in the powder composition was 85% by mass, and the highly unsaturated fatty acid content was 41% by mass relative to the constituent fatty acids of the phospholipid. The bulk density was 0.144 g / cm 3 and the water content was 2% by mass. This powder composition passed 90.1% by mass of a sieve having a nominal size of 1.40 mm and 3.3% by mass of a sieve having a 425 μm size. The angle of repose of this powder was 51 degrees.
一方、比較例２では得られたリン脂質２００ｇに水３５０ｇを加えて均一なエマルションになるまで攪拌した後、凍結乾燥を行なった。実施例と同様の手法で粉砕を試みたが、固形物の粘性が強いためか、粉砕にムラがあり均一な粉体は得られなかった。嵩密度は０．５５ｇ／ｃｍ３で、水分は１．３質量％であった。呼び寸法９．５２ｍｍの篩を通過しない成分が３２．９質量％であった。安息角は流動性が悪く再現性が得られなかった。 On the other hand, in Comparative Example 2, 350 g of water was added to 200 g of the obtained phospholipid and stirred until a uniform emulsion was obtained, followed by lyophilization. Although pulverization was attempted in the same manner as in the example, uniform powder could not be obtained due to unevenness in pulverization because of the strong viscosity of the solid matter. The bulk density was 0.55 g / cm 3 and the water content was 1.3% by mass. The component not passing through a sieve having a nominal size of 9.52 mm was 32.9% by mass. The angle of repose was poor in fluidity and could not be reproduced.
実施例２は水への分散性が良く容易に分散液となった。一方、比較例２は一部が固まりのまま水中に浮遊していた。
また、それぞれのリン脂質３０ｇに、アスコルビン酸ナトリウムを５０ｇ、カテキン３ｇ、市販の砂糖１０００ｇを測り取り、Ｖ型混合機で混合した。リン脂質の濃度の変動係数は実施例２で１１．６、比較例２では５４．９であった。
Example 2 was easily dispersible with good water dispersibility. On the other hand, the comparative example 2 was floating in water with a part solidified.
In addition, 50 g of sodium ascorbate, 3 g of catechin, and 1000 g of commercially available sugar were measured and mixed with 30 g of each phospholipid using a V-type mixer. The variation coefficient of the phospholipid concentration was 11.6 in Example 2 and 54.9 in Comparative Example 2.
本発明の粉体組成物は人体に有用で、ハンドリング性が良く、水への分散性も良好なので健康食品や機能性食品の分野で好適に利用できる。 Since the powder composition of the present invention is useful for the human body, has good handleability and good dispersibility in water, it can be suitably used in the fields of health foods and functional foods.
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| CN112513233A (en) * | 2018-05-16 | 2021-03-16 | 阿卡斯蒂制药股份有限公司 | Process for making phospholipid-enriched compositions |
| JP2021155565A (en) * | 2020-03-27 | 2021-10-07 | 株式会社 ビーアンドエス・コーポレーション | Method for producing functional material containing ether-type glycerophospholipids |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112513233A (en) * | 2018-05-16 | 2021-03-16 | 阿卡斯蒂制药股份有限公司 | Process for making phospholipid-enriched compositions |
| JP2021523279A (en) * | 2018-05-16 | 2021-09-02 | アカスティ ファーマ インコーポレイテッド | Method for Producing Highly Concentrated Phospholipid Composition |
| EP3794098A4 (en) * | 2018-05-16 | 2022-01-12 | Acasti Pharma, Inc. | Process for the manufacture of enriched phospholipid compositions |
| JP2021155565A (en) * | 2020-03-27 | 2021-10-07 | 株式会社 ビーアンドエス・コーポレーション | Method for producing functional material containing ether-type glycerophospholipids |
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