JPS63279753A - Production of enzyme-modified lecithin - Google Patents
Production of enzyme-modified lecithinInfo
- Publication number
- JPS63279753A JPS63279753A JP62116359A JP11635987A JPS63279753A JP S63279753 A JPS63279753 A JP S63279753A JP 62116359 A JP62116359 A JP 62116359A JP 11635987 A JP11635987 A JP 11635987A JP S63279753 A JPS63279753 A JP S63279753A
- Authority
- JP
- Japan
- Prior art keywords
- lecithin
- enzyme
- lysolecithin
- modified lecithin
- derived
- 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
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical class 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 title claims abstract description 88
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000000787 lecithin Substances 0.000 claims abstract description 42
- 229940067606 lecithin Drugs 0.000 claims abstract description 42
- 235000010445 lecithin Nutrition 0.000 claims abstract description 42
- 239000000203 mixture Substances 0.000 claims abstract description 20
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 235000021588 free fatty acids Nutrition 0.000 claims abstract description 8
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229930014626 natural product Natural products 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 6
- CWRILEGKIAOYKP-SSDOTTSWSA-M [(2r)-3-acetyloxy-2-hydroxypropyl] 2-aminoethyl phosphate Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCCN CWRILEGKIAOYKP-SSDOTTSWSA-M 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 102100037611 Lysophospholipase Human genes 0.000 claims abstract 2
- 108010058864 Phospholipases A2 Proteins 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- RYCNUMLMNKHWPZ-SNVBAGLBSA-N 1-acetyl-sn-glycero-3-phosphocholine Chemical compound CC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C RYCNUMLMNKHWPZ-SNVBAGLBSA-N 0.000 claims description 4
- ZPDQFUYPBVXUKS-YADHBBJMSA-N 1-stearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC[C@H](N)C(O)=O ZPDQFUYPBVXUKS-YADHBBJMSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- UOXRPRZMAROFPH-IESLQMLBSA-N lysophosphatidylinositol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)OC1[C@H](O)[C@@H](O)C(O)[C@@H](O)[C@H]1O UOXRPRZMAROFPH-IESLQMLBSA-N 0.000 claims description 4
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 1
- -1 aliphatic alcohols Chemical class 0.000 abstract description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 7
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 5
- 238000004945 emulsification Methods 0.000 abstract description 2
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 abstract 1
- 102000015439 Phospholipases Human genes 0.000 abstract 1
- 108010064785 Phospholipases Proteins 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 description 20
- 229920002472 Starch Polymers 0.000 description 12
- 239000008107 starch Substances 0.000 description 11
- 235000019698 starch Nutrition 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 206010016807 Fluid retention Diseases 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 229930006000 Sucrose Natural products 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000001804 emulsifying effect Effects 0.000 description 6
- 229940112824 paste Drugs 0.000 description 6
- 239000005720 sucrose Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 230000015784 hyperosmotic salinity response Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 235000019484 Rapeseed oil Nutrition 0.000 description 3
- 230000009144 enzymatic modification Effects 0.000 description 3
- 238000002715 modification method Methods 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 108010019160 Pancreatin Proteins 0.000 description 2
- 108091005804 Peptidases Proteins 0.000 description 2
- 239000004365 Protease Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000019658 bitter taste Nutrition 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 230000020176 deacylation Effects 0.000 description 2
- 238000005947 deacylation reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229940055695 pancreatin Drugs 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 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 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- 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 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940026565 lecithin paste Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Landscapes
- Grain Derivatives (AREA)
- General Preparation And Processing Of Foods (AREA)
- Jellies, Jams, And Syrups (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は、天然物由来のレシチン（１，２−ジアシルグ
リセロリン脂質）をＰＬＡ、により部分加水分解してリ
ゾレシチン（１−モノアシルグリセロリン脂質）へと改
質し、反応中に生成する遊離脂肪酸及び原料由来の他の
脂溶成分を有機溶剤により分離除去して精製した総リン
脂質中に６０重量％以上のりゾレシチン成分を含む酵素
改質レシチンの製造法に関するものである。Detailed Description of the Invention The present invention involves partially hydrolyzing naturally derived lecithin (1,2-diacylglycerophospholipid) with PLA to modify it into lysolecithin (1-monoacylglycerophospholipid), and then reacting it. This invention relates to a method for producing enzyme-modified lecithin containing 60% by weight or more of solecithin components in total phospholipids, which are purified by separating and removing free fatty acids and other fat-soluble components derived from raw materials using an organic solvent. .
（産業上の利用分野）
天然物由来のレシチン、主として大豆及び卵黄レシチン
は、天然の乳化剤、界面活性剤として種々の食品、化粧
品、塗料等の工業的用途に使用されるだけでなく、生理
活性効果を有する事から医薬・健康食品分野にも利用さ
れているが、乳化特性及び機能性に関しては、温度、ｐ
Ｈ２塩濃度等の影響に左右され易いために使用用途が限
定きれている。(Industrial Application Fields) Lecithin derived from natural products, mainly soybean and egg yolk lecithin, is not only used as a natural emulsifier and surfactant in various industrial applications such as foods, cosmetics, and paints, but also has physiologically active properties. It is also used in the pharmaceutical and health food fields due to its effectiveness, but its emulsifying properties and functionality are dependent on temperature, p.
Because it is easily influenced by the H2 salt concentration, etc., its uses are limited.
本発明は、酵素改質によりレシチンの乳化特性及び機能
性を改良し、レシチンの新規なる使用用途を供するもの
である。The present invention improves the emulsifying properties and functionality of lecithin through enzyme modification and provides new uses for lecithin.
（従来の技術）
従来レシチンの利用形態としては、原料由来のトリグリ
セリド等の中性脂質を含むペースト状レシチン、中性脂
質をアセトンにて脱脂精製した高純度レシチン及び特定
のリン脂質成分を単離した分画レシチン等（山野、鶴ら
：日食工誌、２９゜１３７２（１９８２）等）が公知で
あるが、更に優れた機能性をレシチンに付与するために
、レシチンを化学的あるいは酵素的に改質する技術が考
案され、水素添加による改質（特願 昭５９−１１６７
１０）、レシチンとデンプンの複合体を調製して乳化力
を高める方法（特願 昭５９−６９１８８）、蛇毒由来
のＰＬＡ、によりリゾレシチンを得る方法（Ａｎａｅｌ
ｌ、Ｇ、Ｂ、＆Ｈａｗｔｈｏｍｅ、Ｊ、Ｎ、、Ｐｈｏｓ
ｐｈｏｌｉｐｉｄａ（１９６４））、パンクレアチンに
より部分加水分解してリゾレシチンを生成する方法（特
願昭５３−７１５１７）等が報告されている。(Prior art) Conventional forms of lecithin usage include paste lecithin containing neutral lipids such as triglycerides derived from raw materials, high purity lecithin obtained by defatting and purifying neutral lipids with acetone, and isolation of specific phospholipid components. Fractionated lecithin etc. (Yamano, Tsuru et al.: Nichiboku Kogyo, 29°1372 (1982), etc.) are known, but in order to give lecithin even better functionality, lecithin can be chemically or enzymatically modified. A technology for reforming by hydrogen addition was devised, and
10), a method for preparing a complex of lecithin and starch to increase emulsifying power (patent application No. 59-69188), a method for obtaining lysolecithin using PLA derived from snake venom (Anael
L, G. B., & Hawthome, J. N., Phos.
pholipida (1964)), a method of partially hydrolyzing with pancreatin to produce lysolecithin (Japanese Patent Application No. 71517/1983), etc. have been reported.
（発明が解決しようとする問題点）
天然レシチン中の主なリン脂質成分は、ホスファチジル
コリン（以下ＰＣとする）、ホスファチジルエタノール
アミン（以下ＰＥとする）、ホスファチジルイノシトー
ル（以下ＰＩとする）及びホスファチジルセリン（以下
ＰＳとする）であるが、ＰＩは陰イオン性物質であるた
めにｐＨ変化による界面活性能への影響はほとんど無い
。しかし、ＰＣ，ＰＥ及びＰＳは両イオン性物質である
ために等電点が存在し、その等電点付近、つまりｐＨ１
，５〜３．５の酸性下においてはＰＣ，ＰＥ及びＰＳは
水との親和性が低下し、それに準じて界面活性能も低下
する。また、塩類濃度が高まると水相性が低下し、同様
にして界面活性能が低下する。(Problems to be Solved by the Invention) The main phospholipid components in natural lecithin are phosphatidylcholine (hereinafter referred to as PC), phosphatidylethanolamine (hereinafter referred to as PE), phosphatidylinositol (hereinafter referred to as PI), and phosphatidylserine. (hereinafter referred to as PS), however, since PI is an anionic substance, the surfactant ability is hardly affected by pH changes. However, since PC, PE, and PS are amphoteric substances, they have an isoelectric point.
Under acidic conditions of . Furthermore, when the salt concentration increases, the aqueous compatibility decreases, and the surfactant ability similarly decreases.
上記の様な欠点を補うためには、レシチン自体を改質し
て高親水性化する事が必要となる。その方法としては、
成分のリン脂質の疎水性基である脂肪酸の１個を部分加
水分解する方法、あるいはリン脂質に新たな親水性基を
導入する方法が考えられるが、化学合成手法による改質
は副生成物の混在防止の観点から好ましくなく、デンプ
ンや蛋白質等の水溶性高分子との複合体形成では根本的
な改質とは言えず、更に使用用途を制限する事となる。In order to compensate for the above drawbacks, it is necessary to modify lecithin itself to make it highly hydrophilic. The method is as follows:
Possible methods include partially hydrolyzing one fatty acid, which is a hydrophobic group in the component phospholipid, or introducing a new hydrophilic group into the phospholipid, but modification by chemical synthesis methods is This is undesirable from the viewpoint of preventing mixing, and the formation of complexes with water-soluble polymers such as starch and proteins cannot be said to be fundamental modification, and further limits the applications.
前述の改質方法に比べて、酵素改質法は温和な条件下で
行なわれるために、生成物の変質が抑制される利点があ
るが、使用するＰ Ｌ Ａ ｔが蛇毒由来の場合、酵素
が高価であると共に皮膚浸食性が強いために取り扱い難
いという欠点があり、パンクレアチン等の粗製酵素では
、共雑するリパーゼやプロテアーゼの影響により本来の
力価が発揮きれず、加水分解率が向上しない。それ故、
従来の酵素改質レシチンのりゾレシチン含有量は、総リ
ン脂質中１５〜３５重量％程度に過ぎず、共存する未改
質のレシチン成分と競合して、顕著な効果を呈しなかっ
た。更に、従来の酵素改質レジチンにおいては、脱アシ
ル化に伴う遊離脂肪酸の処理が行なわれておらず、リゾ
レシチンの界面活性能及び安定性を劣化させる要因とな
っている。Compared to the above-mentioned modification methods, the enzyme modification method has the advantage of suppressing the deterioration of the product because it is carried out under mild conditions. However, crude enzymes such as pancreatin cannot demonstrate their original potency due to the influence of contaminating lipases and proteases, resulting in improved hydrolysis rates. do not. Therefore,
The content of solecithin in conventional enzyme-modified lecithin was only about 15 to 35% by weight based on the total phospholipid, and it competed with the coexisting unmodified lecithin component and did not exhibit any significant effect. Furthermore, in conventional enzyme-modified resitin, free fatty acids are not treated with deacylation, which is a factor that deteriorates the surfactant ability and stability of lysolecithin.
（問題を解決するための手段）
天然レシチン本来の特性を生かした改質方法としては、
酵素反応により温和な条件下にてリゾレシチン（１−モ
ノアシルグリセロリン脂質）化させる事が最良である。(Means to solve the problem) As a modification method that takes advantage of the original characteristics of natural lecithin,
It is best to convert it into lysolecithin (1-monoacylglycerophospholipid) under mild conditions by enzymatic reaction.
この反応に使用する酵素としては、バンクレアチン由来
のＰ Ｌ Ａ ２が最適であり、リパーゼやプロテアー
ゼ等の混在は総括性単位当り０．１％以下であることが
好ましい。As the enzyme used in this reaction, PLA 2 derived from vancreatin is most suitable, and the amount of lipase, protease, etc. is preferably 0.1% or less per total unit.
本発明の酵素改質レシチンは、天然物由来の１−モノア
シルグリセロリン脂質即ち、リゾホスファチジルコリン
、リゾホスファチジルエタノールアミン、リゾホスファ
チジルイノシトール、リゾホスファチジルセリンを主成
分とし、総リン脂質中６０重量％以上含まれる事を特徴
とする。The enzyme-modified lecithin of the present invention contains 1-monoacylglycerophospholipids derived from natural products, namely lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylinositol, and lysophosphatidylserine, and contains 60% by weight or more of the total phospholipids. It is characterized by being
１−モノアシルグリセロリン脂質とジアシルグリセロリ
ン脂質の界面活性能は大きく異なっており、両者の存在
比により形成されるエマルジョンの性状が決定されるた
め、酵素改質による効果が顕著に呈されるには総リン脂
質９６０重量％以上のりゾレシチン成分が存在する事が
必要である。The surfactant abilities of 1-monoacylglycerophospholipids and diacylglycerophospholipids are greatly different, and the nature of the emulsion formed is determined by the abundance ratio of the two, so it is necessary for enzyme modification to have a significant effect. It is necessary that the solecithin component be present in an amount of 960% by weight or more of total phospholipids.
また、リゾホスファチジルコリン、リゾホスファチジル
エタノールアミン、リゾホスファチジルイノシトール、
リゾホスファチジルセリンの存在比は、原料となる天然
物の組成に依存するが、他のリン脂質、例えばスフィン
ゴミエリン、カルシオリピン、プラスマローゲン等の複
合リン脂質は界面活性向上の観点から、除去される事が
望ましい。In addition, lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylinositol,
The abundance ratio of lysophosphatidylserine depends on the composition of the natural product as a raw material, but other phospholipids, such as complex phospholipids such as sphingomyelin, calciolipin, and plasmalogen, may be removed from the viewpoint of improving surface activity. is desirable.
酵素反応時に遊離される脂肪酸は、レシチン及び酵素改
質レシチンの安定性に悪影響を及ぼし、応用に際して製
品の味、臭気及び色調を損なうため除去する事が望まし
い。従来、レシチンの脱脂精製には主としてアセトンが
使用されていたが、アセトン処理の場合、レシチンのア
セトン付加物が生成されて独特の苦味と臭気が生じると
共に原料由来の色素成分が残留し易い欠点があった。本
発明において脱脂精製に使用する有機溶剤は、メタノー
ル、エタノーノ呟 プロパノール、イソプロパノールの
低分子量脂肪族アルコール群から選定されるために苦味
及び異臭の生成が無く、精製されるリン脂質の純度は非
常に高くなる。上記有機溶剤の選定は応用分野に従い、
適宜性なって差し支えない。Fatty acids liberated during enzymatic reactions adversely affect the stability of lecithin and enzyme-modified lecithin, and impair the taste, odor, and color of the product during application, so it is desirable to remove them. Conventionally, acetone has been mainly used for defatting and refining lecithin, but acetone treatment produces an acetone adduct of lecithin, which produces a unique bitter taste and odor, and has the disadvantage that pigment components derived from raw materials tend to remain. there were. In the present invention, the organic solvent used for degreasing and refining is selected from the low molecular weight aliphatic alcohol group of methanol, ethanol, propanol, and isopropanol, so there is no generation of bitterness or off-odor, and the purity of the purified phospholipids is extremely high. It gets expensive. The above organic solvents are selected according to the field of application.
It doesn't matter if it's appropriate.
（作用）
本発明の酵素改質レシチンは、リゾレシチン（１−モノ
アシルグリセロリン脂質）即ち、リゾホスファチジルコ
リン、リゾホスファチジルエタノールアミン、リゾホス
ファチジルイノシトール、リゾホスファチジルセリンの
一種又は二種以上の混合物を主成分とするために極性基
の電気化学的性質は従来のレシチンと変わらないが、脱
アシル化により親水性が向上しているために水和力が高
まり、高温、酸性及び高塩濃度下における乳化安定性は
従来レシチンに比較して著しく向上する。(Function) The enzyme-modified lecithin of the present invention contains lysolecithin (1-monoacylglycerophospholipid), that is, one or a mixture of two or more of lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylinositol, and lysophosphatidylserine as a main component. Therefore, the electrochemical properties of the polar group are the same as conventional lecithin, but the hydrophilicity is improved by deacylation, which increases the hydration power and improves emulsion stability under high temperature, acidity, and high salt concentration. is significantly improved compared to conventional lecithin.
また、従来のレシチンを使用した乳化系は、水中油滴型
（０／Ｗ型）では安定であるが、油中水滴型（Ｗ２Ｏ型
）では安定化しにくい事が知られている。それは、従来
のレシチン中のジアシルグリセロリン脂質の２個の脂肪
酸基が、Ｗ１０型系では相互間の斥力により反発し合い
、ミセル構造を疎にするためと考えられる。酵素改質レ
シチンの場合は、公知のモノグリセリドと同様に規則正
しいミセル構造を作り得るためにＯ／Ｗ型乳型性化性上
するだけでなく、Ｗ２Ｏ型での乳化性も向上する。更に
、酵素改質レシチンはデンプンのヨウ素呈色反応性を著
しく低下させる。これは、デンプンとの複合体形成能が
高い事を示しており、デンプンの機能性改良に使用した
場合には、保水性、ゲル強度等に関して顕著な効果を呈
する。Furthermore, it is known that conventional emulsification systems using lecithin are stable in the oil-in-water type (O/W type), but are difficult to stabilize in the water-in-oil type (W2O type). This is thought to be because the two fatty acid groups of the diacylglycerophospholipid in conventional lecithin repel each other due to mutual repulsion in the W10 type system, making the micelle structure sparse. In the case of enzyme-modified lecithin, since it can form a regular micelle structure like known monoglycerides, it not only improves the O/W type emulsifying property but also improves the W2O type emulsifying property. Additionally, enzyme-modified lecithin significantly reduces the iodine color reactivity of starch. This shows that it has a high ability to form a complex with starch, and when used to improve the functionality of starch, it exhibits remarkable effects on water retention, gel strength, etc.
以上の様なリゾレシチンの機能性を充分に発揮させるた
めには、遊離脂肪酸の除去する事が重要となる。In order to fully demonstrate the functionality of lysolecithin as described above, it is important to remove free fatty acids.
以下の実施例及び比較例にて本発明を具体的に説明する
が、これにより本発明が限定されるものではない。The present invention will be specifically explained using the following Examples and Comparative Examples, but the present invention is not limited thereto.
実施例、１
ペースト状レシチン（レシチンＡＹニリン詣質含量６５
％、豊年製油特製）２０ｋｇにｎ−ヘキサン１（［を加
えて攪拌溶解した後、ＰＬＡ、の１．０Ｘ１０’Ｕを塩
化カルシウム０．０５モルを含む０．１Ｍトリス（ヒド
ロキシメチル）アミノメタン−塩酸緩衝液（ｐＨ７，３
）５．０ｊ２に分散溶解して調製したＰ Ｌ Ａ ｘ溶
液を添加して、連続攪拌下４０°Ｃで４８時間反応した
。Example 1 Lecithin Paste (Lecithin AY Nilin Substance Content 65
%, Hounen Oil Special) to 20 kg of n-hexane (1), stirred and dissolved, then 1.0 x 10'U of PLA was added to 0.1 M tris(hydroxymethyl)aminomethane containing 0.05 mol of calcium chloride. Hydrochloric acid buffer (pH 7.3
) A PLA x solution prepared by dispersing and dissolving in 5.0j2 was added, and the mixture was reacted at 40°C for 48 hours with continuous stirring.
反応後、ｎ−ヘキサン及び水分を減圧留去して得られる
ペースト状の反応生成物をｎ−ヘキサン１（ｌ中に分散
溶解させて、セライト及び微細セルロース粉末の混合物
を通して吸引濾過した後、ｎ−ヘキサンを減圧留去し、
得られたペースト状生成物を８倍容量以上のエタノール
にて・脱脂処理を行なった後、減圧下乾燥して酵素改質
レシチン６．５０ｋｇを得た。After the reaction, the paste-like reaction product obtained by distilling off n-hexane and water under reduced pressure was dispersed and dissolved in 1 (l) of n-hexane, and after suction filtration through a mixture of celite and fine cellulose powder, - Hexane is distilled off under reduced pressure,
The resulting paste-like product was defatted with 8 times the volume or more of ethanol, and then dried under reduced pressure to obtain 6.50 kg of enzyme-modified lecithin.
本酵素改質レシチンのベンゼン不溶分は０．０１％、ア
セトン不溶分は９８．８０％であり、高速液体クロマト
グラフィー及び薄層クロマトグラフィーにて分析した結
果、リゾレシチン含有量は８５モル％（約７０重量％）
であった。The benzene-insoluble content of this enzyme-modified lecithin is 0.01%, and the acetone-insoluble content is 98.80%.As a result of analysis by high performance liquid chromatography and thin layer chromatography, the lysolecithin content was 85 mol% (approx. 70% by weight)
Met.
試験例、１
実施例、１と同様にして、ペースト状レシチン（レシチ
ンＡＹニリン脂質含量６５％、豊年製油■製）２０ｋｇ
にｎ−ヘキサン１０１を加えて攪拌溶解した後、ＰＬＡ
ｚの１．０Ｘ１０’Ｕを塩化カルシウム０．０５モルを
含む０．１Ｍ）リス（ヒドロキシメチル）アミツメクン
−塩酸緩衝液（ｐＨ７，３）５．（ｌに分散溶解して調
製したＰＬＡ、溶液を添加して、連続攪拌下４０°Ｃで
１５時間反応した後、脱脂精製を行なってリゾレシチン
含有量３５重量％の酵素改質レシチン（ベンゼン不溶分
０．０１％、アセトン不溶分９９．０５％）を作り、実
施例、１の酵素改質レシチンとの乳化特性を比較した。Test Example 1 In the same manner as in Example 1, 20 kg of paste lecithin (lecithin AY diphospholipid content 65%, manufactured by Hounen Oil ■) was prepared.
After adding n-hexane 101 to and dissolving with stirring, PLA
1.0X10'U of z in 0.1M) lis(hydroxymethyl)amitumecun-hydrochloric acid buffer (pH 7,3) containing 0.05 mol of calcium chloride5. (Add the PLA prepared by dispersing and dissolving it in 1 liter of PLA, and react at 40°C for 15 hours with continuous stirring. After degreasing and purifying, enzyme-modified lecithin with a lysolecithin content of 35% by weight (benzene-insoluble content) was added. 0.01%, acetone insoluble content: 99.05%) and compared the emulsifying properties with the enzyme-modified lecithin of Example 1.
両者を水に分散溶解して０．５重量％水溶液を調製し、
この水溶液５０重量部に対して菜種白絞油５０重量部を
加えてホモミキサーにて乳化し、目盛り付試験管に移し
て８０°Ｃにおいて８時間静置した後、全溶液層に対す
る乳化層の割合を測定して乳化安定性を調べた結果、実
施例、１の酵素改質レシチンの乳化安定性は８０％であ
ったが、リゾレシチン含有量３５重量％の酵素改質レシ
チンでは２７％となった。対照として、上記と同様の方
法により測定した脱脂レシチン（セントラルソーヤ社製
）の乳化安定性は１０％であった。Disperse and dissolve both in water to prepare a 0.5% by weight aqueous solution,
50 parts by weight of rapeseed oil was added to 50 parts by weight of this aqueous solution, emulsified in a homomixer, transferred to a graduated test tube, and left to stand at 80°C for 8 hours. As a result of measuring the ratio and examining the emulsion stability, the emulsion stability of the enzyme-modified lecithin of Example 1 was 80%, but that of the enzyme-modified lecithin with a lysolecithin content of 35% by weight was 27%. Ta. As a control, the emulsion stability of defatted lecithin (manufactured by Central Sawyer) measured by the same method as above was 10%.
試験例、２
実施例、１の酵素改質レシチンにて調製した乳化組成物
の耐熱性試験を行なった。Test Example 2 A heat resistance test was conducted on the emulsion composition prepared using the enzyme-modified lecithin of Example 1.
酵素改質レシチンを水に分散溶解して０．５重量％水溶
液を調製する。このレシチン水溶液の５０重量部に対し
て菜種白絞油５０重量部を加えてホモミキサーにて乳化
し、目盛り付試験管に移して５．２５．４０及び８０°
Ｃにおいて８時間静置した後、全溶液層に対する乳化層
の割合を測定して乳化安定性を調べた。また、脱脂レシ
チン（セントラルソーヤ社製）及び粗製酵素改質レシチ
ン（未脱脂量、リゾレシチン含有量約７０重量％／総リ
ン脂質、市販品）を対照として、上記と同様にして乳化
組成物の耐熱性試験を行なった。 得られた結果は図、
１に示した通りで、酵素改質レシチンによる乳化組成物
は顕著な耐熱性を呈するが、遊離脂肪酸を含む粗製酵素
改質レシチンではリン脂質含量を同等にしても、本来の
乳化安定性は発揮きれなかった。Enzyme-modified lecithin is dispersed and dissolved in water to prepare a 0.5% by weight aqueous solution. Add 50 parts by weight of white pressed rapeseed oil to 50 parts by weight of this aqueous lecithin solution, emulsify it in a homomixer, transfer it to a graduated test tube, and add 50 parts by weight to 50 parts by weight.
After being allowed to stand for 8 hours at C, the ratio of the emulsion layer to the total solution layer was measured to examine emulsion stability. In addition, using defatted lecithin (manufactured by Central Sawyer) and crude enzyme-modified lecithin (undefatted amount, lysolecithin content approximately 70% by weight/total phospholipid, commercially available product) as a control, the heat resistance of the emulsified composition was prepared in the same manner as above. A sex test was conducted. The obtained results are shown in the figure.
As shown in 1, emulsion compositions made of enzyme-modified lecithin exhibit remarkable heat resistance, but crude enzyme-modified lecithin containing free fatty acids does not exhibit its original emulsion stability even if the phospholipid content is the same. I couldn't finish it.
試験例、３
実施例、１の酵素改質レシチンにて調製した乳化組成物
の耐酸性試験を行なった。 。Test Example 3 An emulsion composition prepared using the enzyme-modified lecithin of Example 1 was tested for acid resistance. .
酵素改質レシチンをｐＨ３，５，７のゲニン酸緩衝液に
分散溶解して０．５重量％の溶液を調製し、それぞれの
５０重量部に対して菜種白絞油５０重量部を添加してポ
モミキ°サーにて乳化し、目盛り付試験管に移して８０
°Ｃにて４時間静置した後、試験例、２と同様の手法に
て乳化安定性を測定した。また、脱脂レシチン（セント
ラルソーヤ社製）及び粗製酵素改質レシチン（未脱脂量
、リゾレシチン含有量約７０重量％／総リン脂質、市販
品）を対照として上記と同様にして乳化組成物の耐酸性
試験を行なった。Enzyme-modified lecithin was dispersed and dissolved in genic acid buffer solutions of pH 3, 5, and 7 to prepare a 0.5% by weight solution, and 50 parts by weight of rapeseed white squeezed oil was added to 50 parts by weight of each solution. Emulsify with a pomomi mixer and transfer to a graduated test tube for 80 min.
After standing at °C for 4 hours, emulsion stability was measured in the same manner as in Test Example 2. In addition, the acid resistance of the emulsified composition was determined in the same manner as above using defatted lecithin (manufactured by Central Sawyer) and crude enzyme-modified lecithin (undefatted amount, lysolecithin content approximately 70% by weight/total phospholipid, commercially available product). I conducted a test.
各乳化組成物の耐酸性は図、２に示した通りであり、酵
素改質レシチンは顕著な耐酸性を呈したが、粗製酵素改
質レシチンでは理論的力価が発揮されない事が判明した
。The acid resistance of each emulsified composition is as shown in Figure 2, and it was found that the enzyme-modified lecithin exhibited remarkable acid resistance, but the crude enzyme-modified lecithin did not exhibit its theoretical potency.
試験例、４
実施例、１の酵素改質レシチンにて調製した乳化組成物
の耐塩性試験を行なった。Test Example 4 A salt tolerance test of the emulsified composition prepared using the enzyme-modified lecithin of Example 1 was conducted.
酵素改質レシチンを１％塩化ナトリウム水溶液と０．５
％塩化カルシウム水溶液のそれぞれに分散溶解して０．
５重量％溶液を調製する。それぞれの水溶液５０重量部
に対して菜種白絞油５０重量部を加えてホモミキサーに
て乳化し、目盛り付試験管に移して５．２５．４０及び
ｇｏ”ｃにおいて４時間静置した後、試験例、２と同様
の操作にて乳化組成物の耐塩性を調べた。また、脱脂レ
シチン（セントラルソーヤ社製）及び粗製酵素改質レシ
チン（未脱脂量、リゾレシチン含有量約７０重量％／総
リン脂質、市販品）を対照として、上記と同様にして乳
化組成物の耐酸性試験を行なった。Enzyme-modified lecithin with 1% sodium chloride aqueous solution and 0.5
% calcium chloride aqueous solution.
Prepare a 5% by weight solution. Add 50 parts by weight of white rapeseed oil to 50 parts by weight of each aqueous solution, emulsify with a homomixer, transfer to a graduated test tube and leave to stand for 4 hours at 5.25.40 and go''c, The salt tolerance of the emulsified composition was examined in the same manner as in Test Example 2. In addition, defatted lecithin (manufactured by Central Sawyer) and crude enzyme-modified lecithin (undefatted amount, lysolecithin content approximately 70% by weight/total Using phospholipid (commercially available product) as a control, the acid resistance test of the emulsified composition was conducted in the same manner as above.
得られた結果は図３に示した通りで、脱脂レシチンはカ
ルシウムイオン存在下では著しく乳化安定性が低下する
が、酵素改質レシチンを含む乳化組成物は同様の条件下
でも顕著な耐塩性を呈し、この条件下では遊離脂肪酸の
影響は余り認められなかった。The obtained results are shown in Figure 3. Although defatted lecithin exhibits markedly lower emulsion stability in the presence of calcium ions, emulsion compositions containing enzyme-modified lecithin exhibit remarkable salt tolerance even under similar conditions. Under these conditions, no significant influence of free fatty acids was observed.
試験例、５
実施例、１の酵素改質レシチンのデンプンに対する保水
性試験を行なった。Test Example 5 A water retention test of the enzyme-modified lecithin of Example 1 with respect to starch was conducted.
酵素改質レシチンをそれぞれが０．２５．０゜５．１．
０重量％となる様に５％／Ｊ％麦粉デンプン懸濁液中に
分散溶解した後、８０°Ｃ湯浴中にて糊化してデンプン
糊溶液を調製する。このデンプン糊溶液を目盛り付試験
管に移して２５°Ｃにおいて静置し、デンプン糊溶液層
からの離水層長を測定して保水性を調べた。また、脱脂
レシチン（セントラルソーヤ社製）及び粗製酵素改質レ
シチン（未脱脂品、リゾレシチン含有量約７０重量％／
総リン脂質、市販品）、ショ糖脂肪酸エステル（ＨＬＢ
：１６．三菱化成工業■製）を対照として、上記と同様
にして小麦粉デンプンでの保水性試験を行なった。Each enzyme-modified lecithin was 0.25.0°5.1.
After dispersing and dissolving in a 5%/J% wheat starch suspension so that the concentration is 0% by weight, the mixture is gelatinized in a water bath at 80°C to prepare a starch paste solution. This starch paste solution was transferred to a graduated test tube and allowed to stand at 25°C, and the water retention property was examined by measuring the length of the water separation layer from the starch paste solution layer. In addition, defatted lecithin (manufactured by Central Sawyer) and crude enzyme-modified lecithin (undefatted product, lysolecithin content approximately 70% by weight/
Total phospholipids, commercially available products), sucrose fatty acid esters (HLB
:16. A water retention test using wheat flour starch was conducted in the same manner as above, using a sample (manufactured by Mitsubishi Chemical Industries, Ltd.) as a control.
得られた結果は図、４に示した通りで、酵素改質レシチ
ンによる保水性は顕著であり、遊離脂肪酸を含む粗製酵
素改質レシチンではリン脂質含量を同等にしても、本来
の保水性は発揮されなかった。また、ＨＬＢのほぼ等し
いシヨ糖脂肪酸ニス−チルの保水性は、酵素改質レシチ
ンに比べて非常に低いものであった。The obtained results are shown in Figure 4, and the water retention properties of enzyme-modified lecithin are remarkable, while the original water retention properties of crude enzyme-modified lecithin containing free fatty acids are lower even if the phospholipid content is the same. It wasn't demonstrated. Furthermore, the water retention of sucrose fatty acid Nis-Til, which has approximately the same HLB, was much lower than that of enzyme-modified lecithin.
（発明の効果）
本発明は、天然界面活性剤であるレシチンの機能性を改
良する事により利用範囲を飛躍的に拡大すると共に、化
学工業、食生活あるいは医療分野に効果的で、且つ安全
な界面活性剤を供与するも図、１は、酵素改質レシチン
、粗製酵素改質レシチン、脱脂レシチン及びショ糖脂肪
酸エステルにて調製した乳化組成物の耐熱性を乳化安定
性を指標として表わしたものである。(Effects of the Invention) The present invention dramatically expands the scope of use of lecithin, which is a natural surfactant, by improving its functionality. Figure 1 shows the heat resistance of emulsion compositions prepared with enzyme-modified lecithin, crude enzyme-modified lecithin, defatted lecithin, and sucrose fatty acid ester, using emulsion stability as an index. It is.
図、２は、酵素改質レシチン、粗製酵素改質レシチン、
脱脂レシチン及びシヨ糖脂肪酸エステルにて調製した乳
化組成物の耐酸性を乳化安定性を指標として表わしたも
のである。Figure 2 shows enzyme-modified lecithin, crude enzyme-modified lecithin,
The acid resistance of an emulsion composition prepared with defatted lecithin and sucrose fatty acid ester is expressed using emulsion stability as an index.
図、３は、酵素改質レシチン、粗製酵素改質レシチン、
脱脂レシチン及びショ糖脂肪酸エステルにて調製した乳
化組成物の耐塩性を乳化安定性を指標として表わしたも
のである。Figure 3 shows enzyme-modified lecithin, crude enzyme-modified lecithin,
The salt tolerance of an emulsion composition prepared with defatted lecithin and sucrose fatty acid ester is expressed using emulsion stability as an index.
図、４は、酵素改質レシチン、粗製酵素改質レシチン、
脱脂レシチン及びショ糖脂肪酸エステルを添加したデン
プン糊の保水性を表わしたものである。Figure 4 shows enzyme-modified lecithin, crude enzyme-modified lecithin,
This figure shows the water retention properties of starch paste containing defatted lecithin and sucrose fatty acid ester.
Claims (3)
セロリン脂質）をホスフォリパーゼＡ＿２（以下ＰＬＡ
＿２と略す）により部分加水分解してリゾレシチン（１
−モノアシルグリセロリン脂質）へと改質し、反応中に
生成する遊離脂肪酸及び原料由来の他の脂溶成分を有機
溶剤により分離除去して精製したリゾレシチン成分を総
リン脂質中に６０重量％以上含む事を特徴とする酵素改
質レシチンの製造法。(1) Lecithin (1,2-diacylglycerophospholipid) derived from natural products is used as phospholipase A_2 (hereinafter PLA).
Lysolecithin (abbreviated as _2) is partially hydrolyzed with
- Monoacylglycerophospholipids) and purified by separating and removing free fatty acids generated during the reaction and other fat-soluble components derived from the raw materials using an organic solvent, at least 60% by weight of the total phospholipids A method for producing enzyme-modified lecithin characterized by comprising:
ール、プロパノール、イソプロパノールの低分子量脂肪
族アルコール群から選定される事を特徴とする特許請求
の範囲第（１）項記載の酵素改質レシチンの製造法。(2) The enzyme-modified lecithin according to claim (1), wherein the organic solvent used for purification is selected from the low molecular weight aliphatic alcohol group of methanol, ethanol, propanol, and isopropanol. Manufacturing method.
ン、リゾホスファチジルエタノールアミン、リゾホスフ
ァチジルイノシトール及びリゾホスファチジルセリンの
一種又は二種以上の混合物である事を特徴とする特許請
求の範囲第（１）項記載の酵素改質レシチンの製造法。(3) The enzyme according to claim (1), wherein the lysolecithin component is one or a mixture of two or more of lysophosphatidylcholine, lysophosphatidylethanolamine, lysophosphatidylinositol, and lysophosphatidylserine. Method for producing modified lecithin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62116359A JPH066032B2 (en) | 1987-05-12 | 1987-05-12 | Method for producing enzyme-modified lecithin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62116359A JPH066032B2 (en) | 1987-05-12 | 1987-05-12 | Method for producing enzyme-modified lecithin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63279753A true JPS63279753A (en) | 1988-11-16 |
| JPH066032B2 JPH066032B2 (en) | 1994-01-26 |
Family
ID=14685008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62116359A Expired - Fee Related JPH066032B2 (en) | 1987-05-12 | 1987-05-12 | Method for producing enzyme-modified lecithin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH066032B2 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02242643A (en) * | 1989-03-15 | 1990-09-27 | Q P Corp | Anti-aging agent for starch and starchy raw material and starch-containing food containing thereof |
| WO1990011823A1 (en) * | 1989-04-13 | 1990-10-18 | Kabushiki Kaisha Yakult Honsha | Surfactant and process for producing the same |
| JPH04234947A (en) * | 1991-01-09 | 1992-08-24 | Nagoya Seiraku Kk | Cream-like composition |
| JPH08301885A (en) * | 1996-04-01 | 1996-11-19 | Kyowa Hakko Kogyo Co Ltd | Composition comprising lysophospholipid and polyhydric alcohol |
| WO1997028270A1 (en) * | 1996-02-02 | 1997-08-07 | Biomolecular Products, Inc. | Methods for making lysophosphatidylcholine |
| US5891466A (en) * | 1990-08-13 | 1999-04-06 | Yesair; David W. | Mixed Liped-Bicarbonate colloidal particles for delivering drugs or calories |
| WO2002074887A1 (en) * | 2001-03-14 | 2002-09-26 | Ip Holdings, L.L.C. | Methods for recovering fatty acids |
| JP2003093086A (en) * | 2001-09-21 | 2003-04-02 | Taiyo Kagaku Co Ltd | Method for producing lysophospholipid with diminished allergen |
| WO2007004823A1 (en) * | 2005-06-30 | 2007-01-11 | Doosan Corporation | Stable water soluble composition containing lysophosphatidylethanolamine and lecithin |
| JP2014519403A (en) * | 2011-05-10 | 2014-08-14 | アーチャー−ダニエルズ−ミッドランド カンパニー | Dispersant with biological material-derived compound |
| CN114540439A (en) * | 2022-01-28 | 2022-05-27 | 海南乐孕生物科技有限公司 | Extraction process of high-hydrophilicity high-activity enzymolysis soybean phospholipid |
-
1987
- 1987-05-12 JP JP62116359A patent/JPH066032B2/en not_active Expired - Fee Related
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02242643A (en) * | 1989-03-15 | 1990-09-27 | Q P Corp | Anti-aging agent for starch and starchy raw material and starch-containing food containing thereof |
| WO1990011823A1 (en) * | 1989-04-13 | 1990-10-18 | Kabushiki Kaisha Yakult Honsha | Surfactant and process for producing the same |
| US5152928A (en) * | 1989-04-13 | 1992-10-06 | Kabushiki Kaisha Yakult Honsha | Surfactant and method for producing the same |
| US5891466A (en) * | 1990-08-13 | 1999-04-06 | Yesair; David W. | Mixed Liped-Bicarbonate colloidal particles for delivering drugs or calories |
| JPH04234947A (en) * | 1991-01-09 | 1992-08-24 | Nagoya Seiraku Kk | Cream-like composition |
| JP2601950B2 (en) * | 1991-01-09 | 1997-04-23 | 名古屋製酪株式会社 | Creamy composition |
| WO1997028270A1 (en) * | 1996-02-02 | 1997-08-07 | Biomolecular Products, Inc. | Methods for making lysophosphatidylcholine |
| JPH08301885A (en) * | 1996-04-01 | 1996-11-19 | Kyowa Hakko Kogyo Co Ltd | Composition comprising lysophospholipid and polyhydric alcohol |
| WO2002074887A1 (en) * | 2001-03-14 | 2002-09-26 | Ip Holdings, L.L.C. | Methods for recovering fatty acids |
| JP2003093086A (en) * | 2001-09-21 | 2003-04-02 | Taiyo Kagaku Co Ltd | Method for producing lysophospholipid with diminished allergen |
| WO2007004823A1 (en) * | 2005-06-30 | 2007-01-11 | Doosan Corporation | Stable water soluble composition containing lysophosphatidylethanolamine and lecithin |
| KR101028489B1 (en) * | 2005-06-30 | 2011-04-14 | 주식회사 두산 | Stable water soluble composition containing lysophosphatidylethanolamine and lecithin |
| US8217199B2 (en) | 2005-06-30 | 2012-07-10 | Doosan Corporation | Stable water soluble composition containing lysophosphatidylethanolamine and lecithin |
| JP2014519403A (en) * | 2011-05-10 | 2014-08-14 | アーチャー−ダニエルズ−ミッドランド カンパニー | Dispersant with biological material-derived compound |
| CN114540439A (en) * | 2022-01-28 | 2022-05-27 | 海南乐孕生物科技有限公司 | Extraction process of high-hydrophilicity high-activity enzymolysis soybean phospholipid |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH066032B2 (en) | 1994-01-26 |
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