JPS62178596A - Concentration and purification of glycolipid - Google Patents
Concentration and purification of glycolipidInfo
- Publication number
- JPS62178596A JPS62178596A JP1939786A JP1939786A JPS62178596A JP S62178596 A JPS62178596 A JP S62178596A JP 1939786 A JP1939786 A JP 1939786A JP 1939786 A JP1939786 A JP 1939786A JP S62178596 A JPS62178596 A JP S62178596A
- Authority
- JP
- Japan
- Prior art keywords
- acetone
- carbon dioxide
- glycolipid
- glycolipids
- raw material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229930186217 Glycolipid Natural products 0.000 title claims abstract description 32
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical compound O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000000746 purification Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 78
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 26
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 26
- 239000002994 raw material Substances 0.000 claims abstract description 24
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 19
- 239000003921 oil Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000003925 fat Substances 0.000 claims description 3
- 238000007670 refining Methods 0.000 claims description 3
- 235000014593 oils and fats Nutrition 0.000 claims description 2
- 239000000306 component Substances 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 150000003904 phospholipids Chemical class 0.000 abstract description 5
- 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 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 229940083466 soybean lecithin Drugs 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000011282 treatment Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 241000194107 Bacillus megaterium Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000002339 glycosphingolipids Chemical class 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- -1 plant tissue Natural products 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分舒）
本発明は、糖脂質含有原料から糖脂質を＊ｍ・精製する
方法に関する。糖脂質は循環語基の各種改善作用、免疫
の発現や生理活性物質の細胞膜への結合、神経系の伝達
に関与する等の生物活性を有することが見出され、最近
とみに注目を集めている物質である。DETAILED DESCRIPTION OF THE INVENTION (Industrial Application) The present invention relates to a method for purifying glycolipids from glycolipid-containing raw materials. Glycolipids have recently been attracting attention as they have been found to have biological activities such as improving various circulation groups, expressing immunity, binding physiologically active substances to cell membranes, and being involved in nervous system transmission. It is a substance.
（従来の技術）
糖脂質とは単一な物質ではなく、糖と脂質が結合した化
合物の総称である。その中の一群に植物糖脂質（フィト
グリコリピド）があり、これは大豆、とうもろこし、小
麦等の穀物種子中に特に多（存在することが知られてい
る。また、他にも、動物臓器中に存在するスフィンゴ糖
脂質、植物や微生物類の膜構成成分等として知られてい
るグリセロ糖脂質等、生体中には多種の糖脂質が存在し
ている。これらの多くの類縁化合物の中から特定の糖脂
質を単離する方法については生化学的な興味から研究が
なされている［生化学研究法Ｉ （昭和４２年９月２５
日 株式会社朝倉書店発行）第１２６〜１５６頁など。(Prior Art) Glycolipid is not a single substance, but a general term for compounds in which sugar and lipid are combined. One group of these is plant glycolipids (phytoglycolipids), which are known to be particularly abundant in grain seeds such as soybeans, corn, and wheat. Many types of glycolipids exist in living organisms, such as glycosphingolipids that exist in humans, and glyceroglycolipids that are known as membrane constituents of plants and microorganisms. Research has been conducted on methods for isolating glycolipids from biochemical interests [Biochemical Research Methods I (September 25, 1960)
(Published by Asakura Shoten Co., Ltd.) pp. 126-156, etc.
］ これらの主な手段は、溶剤への溶解度の差を利用し
た溶剤分別及びケイ酸等を用いるカラムクロマトグラフ
ィーを組合わせたものであるが、これらはいずれもコス
トが高く、換作が繁雑であるなどして、工業規模の濃縮
・精製に応用されるまでに至っていない。] These main methods are a combination of solvent fractionation that takes advantage of differences in solubility in solvents and column chromatography that uses silicic acid, etc., but both of these methods are expensive and require complicated repurposing. For some reasons, it has not yet been applied to industrial-scale concentration and purification.
（発明が解決しようとする問題点）
本発明者らは、かかる 糖脂質を工業規模で廉価、かつ
容易に取得し得る方法を開発すべく、鋭意研究を行なっ
た結果、糖脂質含有原料を加圧状態の二酸化炭素及びア
セトンにそれぞれ接触すせて、これら原料から加圧状態
の二酸化炭素に可溶性の成分並びにアセトンに不溶性の
成分を除去することにより、極めて効率的に純度の高い
糖脂質が得られろことを見出し、本発明を完成した。(Problems to be Solved by the Invention) The present inventors have conducted intensive research to develop a method for obtaining such glycolipids at low cost and easily on an industrial scale, and as a result, have developed a method for processing glycolipid-containing raw materials. Glycolipids of high purity can be obtained extremely efficiently by contacting pressurized carbon dioxide and acetone to remove components soluble in pressurized carbon dioxide and components insoluble in acetone from these raw materials. He discovered that this could be done and completed the present invention.
（発明の構成）
本発明は、糖脂質含有原料を加圧状態の二酸化炭素及び
アセトンにそれぞれ接触させて、該原料から加圧状態の
二酸化炭素に可溶性の成分及びアセトンに不溶性の成分
を除去することを特徴とする糖脂質の濃縮・精製方法で
ある。(Structure of the Invention) The present invention brings a glycolipid-containing raw material into contact with pressurized carbon dioxide and acetone, respectively, and removes components soluble in pressurized carbon dioxide and components insoluble in acetone from the raw material. This is a method for concentrating and purifying glycolipids.
本発明で用いる原料は、糖脂質を含有する素材であれば
いずれも使用することができ、植物組機、動物組織、微
生物菌体及びこれらの加工品、並びにその加工工程で得
られる副産物等が挙げられろ。The raw materials used in the present invention can be any material containing glycolipids, including plant tissue, animal tissue, microbial cells, processed products thereof, and by-products obtained in the processing process. Can you name it?
これらのうち、例えば、大豆、菜種、綿実、とうもろこ
し、米及び小麦胚芽等の植物油脂原料及びこれらから抽
出して得た植物性油脂、豚、牛、羊等の脂身及びこれら
からレンダリングにより得た動物性油脂、更にはこれら
動植物性油脂の粗油を通常のアルカリ精製法によって精
製する際に副生する、所謂抽出油滓およびソーダ油滓等
の油滓類、粗油を限外ろ過膜などで処理する際の膜不透
過画分などが、工業規模で大量、かつ安定して入手可能
な原料として特に有用である。Among these, for example, vegetable oil raw materials such as soybeans, rapeseed, cottonseed, corn, rice and wheat germ, vegetable oils and fats extracted from these, fatty meat of pigs, cows, sheep, etc., and fats obtained from these by rendering. An ultrafiltration membrane is used to filter the crude oils, so-called soapstocks and soda soapstocks, etc., which are by-produced when refining the crude oils of these animal and vegetable oils using normal alkaline refining methods. The membrane-impermeable fractions obtained when treated with the above-mentioned methods are particularly useful as raw materials that can be stably obtained in large quantities on an industrial scale.
使用する原料により適宜の前処理が必要であり、大豆等
の植物油脂原料等を固形物のまま直接処理する場合には
予め薄片状に圧扁するか、６０メツシユあるいはそれ以
下の粒度にまで粉砕するのがよく、酵母等の微生物国体
では超音波破砕等により細胞膜を破砕しておくのがよい
。また、例えば油滓類のように水分を多量に含む素材で
は、予め ′乾燥して水分を除いておくことが望ま
しい。Appropriate pretreatment is required depending on the raw materials used. When directly processing vegetable oil raw materials such as soybeans in solid form, they must be pressed into thin flakes in advance or ground to a particle size of 60 mesh or smaller. In the case of microorganisms such as yeast, it is recommended to disrupt the cell membranes by ultrasonic disruption or the like. In addition, for materials containing a large amount of water, such as soapstock, it is desirable to dry the material in advance to remove the water.
本発明では、これらの原料を、加圧状態の二酸化炭素及
びアセトンに接触させるが、その方法を具体的に示すな
らば以下のとおりである。In the present invention, these raw materials are brought into contact with pressurized carbon dioxide and acetone, and the specific method is as follows.
加圧状態の二酸化炭素による処理は、必要に応じて前記
のような前処理を施した原料をそのまま或いは金属性の
ビーズ、金網等の担体に担持させるなどし、耐圧容器内
で系の温度を一１０〜８０℃、圧力を３０〜９００ ｋ
ｇ ／ ｃｆに保ちつツ、緩やかに攪拌しながら、そ
の一部を流出させつつ二酸化炭素を連続的に注入して行
うのがよい。加圧状態の二酸化炭素が系の温度と圧力に
応じて液状または超臨界状態を呈し、これらが油脂類の
抽出に利用され得ることは、例えば、雑誌「油化学」第
３１巻第７号４１１〜４１３頁（１９８２）等に記載さ
れて公知である。本発明においても加圧状態の二酸化炭
素を液状もしくは超臨界状態で使用するのが特に有利で
ある。For treatment with pressurized carbon dioxide, if necessary, the raw material that has been pretreated as described above may be supported as it is or supported on a carrier such as metal beads or wire mesh, and the temperature of the system is raised in a pressure-resistant container. -10~80℃, pressure 30~900k
It is preferable to carry out this by continuously injecting carbon dioxide while maintaining the temperature at 2 g/cf, stirring gently, and letting a portion of the carbon dioxide flow out. The fact that pressurized carbon dioxide exhibits a liquid or supercritical state depending on the temperature and pressure of the system, and that these can be used for the extraction of oils and fats is reported, for example, in the magazine "Yuukagaku" Vol. 31, No. 7, 411. -413 pages (1982), etc., and is publicly known. Also in the present invention, it is particularly advantageous to use pressurized carbon dioxide in liquid or supercritical state.
この処理により原料中のトリグリセライド及びその部分
分解物、遊離脂肪酸、ステロール、トコフェロール等が
除去される。This treatment removes triglycerides and their partial decomposition products, free fatty acids, sterols, tocopherols, etc. in the raw materials.
アセトンによる処理では、容器内で被処理物の５〜２０
倍相当量のアセトンを用い、好ましくは一１０〜５℃に
保ちつつ、撹拌しながら行い、事後、濾過等の適当な手
段により不溶性成分を除き、アセトンを置去する。In the treatment with acetone, 5 to 20
The reaction is carried out using an equivalent amount of acetone, preferably maintained at -10 to 5° C., with stirring. Afterwards, insoluble components are removed by appropriate means such as filtration, and the acetone is removed.
本発明法では原料に上記の如き加圧状態の二酸化炭素に
よる処理とアセトンによる処理とを施すのであるが、こ
の二つの処理は順序の如何にかかわらず略同様の結果が
得られるので、処理の順序に特に限定はない。In the method of the present invention, the raw material is treated with pressurized carbon dioxide and acetone as described above, but these two treatments yield almost the same results regardless of the order. There is no particular restriction on the order.
糖脂質含有原料に以上の二種の溶剤処理を施して得られ
た製品は、複数の溶媒系で展開した薄層クロマトグラム
上で、いずれもほぼ単一のスポットを示し、中性脂質や
燐脂質の存在が殆ど見られないなど、極めて純度の高い
糖脂質であることが認められた。収率は使用する原料に
依存するが、含油大豆レシチン（大豆抽出油滓を薄膜乾
爆機で水分２％にまで乾燥したもの）を用いた場合では
、原料の１〜４％であった。Products obtained by subjecting glycolipid-containing raw materials to the above two types of solvent treatment show almost a single spot on thin layer chromatograms developed with multiple solvent systems, and neutral lipids and phosphorus It was confirmed that the glycolipids were of extremely high purity, with almost no presence of lipids observed. The yield depends on the raw material used, but when oil-containing soybean lecithin (soybean extracted soapstock dried to a moisture content of 2% in a thin film dryer) was used, it was 1 to 4% of the raw material.
（実施例）
実施例 １
アセトン可溶物（主として中性油）が３６゜３％である
含油大豆レシチン４００ｇを４１容の耐圧容器中で１５
℃、１５０ｋｇ／ｃｒＩの条件で液状の二酸化炭素によ
り８時間、通液量６５００ＯＮｌで処理した。処理後、
圧力を解放して容器内の残留物２４５ｇを得た。(Example) Example 1 400 g of oil-impregnated soybean lecithin containing 36.3% of acetone soluble matter (mainly neutral oil) was mixed in a 41-volume pressure vessel at 15%
It was treated with liquid carbon dioxide at 150 kg/crI for 8 hours at a flow rate of 6500 ONl. After treatment,
The pressure was released to obtain 245 g of residue in the container.
この一部５０ｇをとり０℃の冷アセトン１４を加えて３
０分間攪拌した後、遠心分離により不溶物を分離した。Take 50g of this and add 14 ml of cold acetone at 0°C.
After stirring for 0 minutes, insoluble matter was separated by centrifugation.
不溶物は更に冷アセトン１ｊで同様に処理した。アセト
ン溶液を合し、エバポレーク−でアセトンを溜去して、
淡黄色の固形物２゜２ｇを得た。氷晶のヘキサン溶液を
シリカゲル薄層にスポットし、クロロホルム−メタノー
ル−水（４０： ２０： ２）の溶媒で展開した後
硫酸で発色させろと、Ｒｆ値が約０．８の単一スポット
が得られた。Insoluble matter was further treated in the same manner with cold acetone 1j. Combine the acetone solutions, distill off the acetone with an evaporative lake,
2.2 g of pale yellow solid was obtained. A hexane solution of ice crystals was spotted on a thin layer of silica gel, developed with a solvent of chloroform-methanol-water (40:20:2), and then colored with sulfuric acid.A single spot with an Rf value of about 0.8 was obtained. It was done.
本物質は糖の検出試薬であるアンスロン試薬に陽性で、
燐検出試薬のディトマー試薬に陰性であるなどから、燐
脂質を含まない純度の高い糖脂質であることが分った。This substance is positive for Anthrone reagent, which is a sugar detection reagent.
It was found to be a highly pure glycolipid that does not contain phospholipids, as it was negative for Dittmer reagent, a phosphorus detection reagent.
実施例 ２
含油大豆レシチン２００ｇを微粉末セルロース（商品名
アビセル）２００ｇと均一に混合し、これを４１容の耐
圧容器中で４０℃、３００ｋｇ／ｄの条件下で超臨界状
態の二酸化炭素により４時間、通液量４４００ＯＮｌで
処理した。処理後、圧力を解放して容器内の残留物３２
０ｇを得た。Example 2 200 g of oil-containing soybean lecithin was uniformly mixed with 200 g of finely powdered cellulose (trade name Avicel), and this was heated with supercritical carbon dioxide at 40°C and 300 kg/d in a 41-volume pressure vessel. The treatment was carried out for a time of 4,400 ONl. After processing, release the pressure and remove the residue 32 in the container.
Obtained 0g.
この一部１００ｇに対し０℃のアセトン２４を加え２０
分間攪拌した後、遠心分離により不溶物を分離した。不
溶物は更にＯ℃アセトン１１で同様に処理した。アセト
ン溶液を合し、エバポレーターによりアセトンを溜去し
て、固形物１．６ｇをえた。 氷晶を実施例１同様にシ
リカゲル薄層クロマトグラフィーで確認したところ、中
性脂質及び燐脂質の存在は認められず、純度の高い糖脂
質であることが確認された。To 100g of this portion, add 24g of acetone at 0°C and add 20g of acetone.
After stirring for a minute, insoluble matter was separated by centrifugation. Insoluble matter was further treated in the same manner with 11 ml of acetone at 0°C. The acetone solutions were combined and the acetone was distilled off using an evaporator to obtain 1.6 g of a solid. When the ice crystals were confirmed by silica gel thin layer chromatography in the same manner as in Example 1, the presence of neutral lipids and phospholipids was not observed, and it was confirmed that the ice crystals were highly pure glycolipids.
実施例３
菜種粗油の脱ガム工程で得られた抽出油滓（水分３４．
３％、乾燥重量当たりのアセトン可溶物３７．９％）１
００ｇに０℃のアセトン２１を加え、２０分間攪拌した
。遠心分離により得た不溶物は更に冷アセトン１ｊを加
え、同様に処理した。遠心分離により得たアセトン溶液
を合し、エバポレーターでアセトンを溜去して２５ｇの
油状物を得た。この油状物２０ｇを７５ｍｊ容の耐圧容
器中４０℃、３００ｋｇ／ｃａｒの条件下で超臨界状態
の二酸化炭素で５時間処理しな。この間の二酸化炭素の
通液量は３９７ＯＮｌであった。Example 3 Extracted soapstock obtained in the degumming process of crude rapeseed oil (water content: 34.
3%, acetone solubles per dry weight 37.9%) 1
Acetone 21 at 0°C was added to 00g and stirred for 20 minutes. The insoluble matter obtained by centrifugation was treated in the same manner with the addition of 1j of cold acetone. The acetone solutions obtained by centrifugation were combined, and the acetone was distilled off using an evaporator to obtain 25 g of an oily substance. 20 g of this oil was treated with supercritical carbon dioxide for 5 hours at 40° C. and 300 kg/car in a 75 mj capacity pressure vessel. The amount of carbon dioxide passed during this period was 397 ONl.
処理後、容器の圧力を解放して微黄色の固形物０゜１２
ｇを得た。氷晶を実施例１と同様にシリカゲル薄層クロ
マトグラフィーで調べた結果、中性脂質及び燐脂質の存
在は認められず純度の高い糖脂質であることが確認され
た。After treatment, release the pressure in the container and remove the slightly yellow solid.
I got g. As a result of examining the ice crystals by silica gel thin layer chromatography in the same manner as in Example 1, the presence of neutral lipids and phospholipids was not observed, and it was confirmed that the ice crystals were highly pure glycolipids.
実施例 ４
脱皮大豆フレーク４００ｇを４１容の耐圧容器に入れ、
４０℃、３００ｇｋｇ／ｃＩＩｒの条件下で超臨界状態
の二酸化炭素で７時間処理した。この間の二酸化炭素の
通液量は５９４０ＯＮｔ’であった。Example 4 400g of dehulled soybean flakes was placed in a 41 volume pressure container,
It was treated with supercritical carbon dioxide at 40° C. and 300 gkg/cIIr for 7 hours. The amount of carbon dioxide passed during this period was 5940 ONt'.
処理後、容器の圧力を解放して残留物４０７ｇを得な。After processing, release the pressure in the vessel to obtain 407 g of residue.
この一部４００ｇに対し一３℃のアセトン２１を加え２
０分間攪拌した後、遠心分離により不溶物を分離した。To 400g of this part, add 21 parts of acetone at -3°C.
After stirring for 0 minutes, insoluble matter was separated by centrifugation.
不溶物は更に−３℃アセ■・ン１１で同様に処理した。The insoluble matter was further treated in the same manner with -3°C acetone 11.
アセトン溶液を合し、エバポレーターによりアセトンを
溜去して、固形物０．１９ｇを得た。氷晶を実施例１同
様にシリカゲル薄層クロマトグラフィーで確認したとこ
ろ、糖脂質の他少量の単糖及びオリゴ糖が見られたが、
中性脂質及び燐油脂質の存在は認められなかった。The acetone solutions were combined and the acetone was distilled off using an evaporator to obtain 0.19 g of a solid. When ice crystals were confirmed by silica gel thin layer chromatography in the same manner as in Example 1, small amounts of monosaccharides and oligosaccharides were found in addition to glycolipids.
The presence of neutral lipids and phospholipids was not observed.
実施例 ５
超音波破砕後、凍結乾燥して得たバチルス・メガテリウ
ム（Ｂａｃｉｌｌｕｓ ｍｅｇａｔｅｒｉｕｍ）の菌
体３．６ｇを７５ ｍ ｌ！容の耐圧容器中で４０℃、
３００ｋｇ／ｃｎｉの条件で超臨界状態の二酸化炭素に
より４時間、通液量２２０ＯＮｌで処理した。容器内の
残留物を０℃のアセトン５０ｍ１で、各３０分間攪拌抽
出し、遠心分離により不溶物を分離した。アセトン溶液
をきし、エバポレーターでアセトンを溜去して、白色の
固形物１１．４ｍｇを得た。Example 5 75 ml of 3.6 g of Bacillus megaterium cells obtained by ultrasonic crushing and freeze-drying! 40℃ in a pressure-resistant container with
It was treated with supercritical carbon dioxide at a flow rate of 300 kg/cni for 4 hours at a flow rate of 220 ONl. The residue in the container was extracted with 50 ml of acetone at 0° C. with stirring for 30 minutes each time, and insoluble matter was separated by centrifugation. The acetone solution was filtered and the acetone was distilled off using an evaporator to obtain 11.4 mg of a white solid.
氷晶はアンスロン試薬に陽性、ディトマー試薬に陰性で
あり、実施例１同様の薄層クロマトグラフィーで単一ス
ポットが得られた。The ice crystals were positive to Anthrone's reagent and negative to Dittmer's reagent, and a single spot was obtained by thin layer chromatography in the same manner as in Example 1.
（発明の効果）
本発明によれば、植物組織、動物組織、微生物菌体及び
これらの加工品、並びにその加工工程で得られる副産物
等の広範な原料を加圧状態の二酸化炭素及びアセトンと
いう溶解特性の異なる２種類の溶剤を巧みに組合せて処
理することによって、純度の高い糖脂質を廉価、かつ容
易に取得することができる。(Effects of the Invention) According to the present invention, a wide range of raw materials such as plant tissues, animal tissues, microbial cells, processed products thereof, and by-products obtained in the processing steps are dissolved in pressurized carbon dioxide and acetone. By skillfully combining two types of solvents with different properties, highly pure glycolipids can be obtained easily and at low cost.
本発明法により得られる糖脂質は純度が高く、風味や色
相等品質に悪影響を及ぼす不都合な成分が除去されてい
るため、今後使用量が拡大するとみられろ健康食品や医
薬分野での用途に好適なものである。The glycolipids obtained by the method of the present invention have a high purity, and undesirable components that adversely affect quality such as flavor and color have been removed, so the amount of use is expected to expand in the future. It is suitable.
以上that's all
Claims (3)
トンに接触せしめ、該原料から加圧状態の二酸化炭素に
可溶性の成分並びにアセトンに不溶性の成分を除去して
糖脂質を濃縮・精製することを特徴とする糖脂質の濃縮
・精製方法。(1) Glycolipid-containing raw materials are brought into contact with pressurized carbon dioxide and acetone, and components soluble in pressurized carbon dioxide and components insoluble in acetone are removed from the raw materials to concentrate and purify the glycolipids. A method for concentrating and purifying glycolipids, which is characterized by the following.
は油脂の精製過程で得られる油滓類を用いる特許請求の
範囲第（１）項記載の糖脂質の濃縮・精製方法。(2) The method for concentrating and purifying glycolipids according to claim (1), which uses an oil- or fat-containing substance, oil, or soapstock obtained in the process of refining oils and fats as the glycolipid-containing raw material.
の二酸化炭素である特許請求の範囲第（１）項または第
（２）項記載の糖脂質の濃縮・精製方法。(3) The method for concentrating and purifying glycolipids according to claim (1) or (2), wherein the pressurized carbon dioxide is liquid or supercritical carbon dioxide.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1939786A JPS62178596A (en) | 1986-01-31 | 1986-01-31 | Concentration and purification of glycolipid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1939786A JPS62178596A (en) | 1986-01-31 | 1986-01-31 | Concentration and purification of glycolipid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62178596A true JPS62178596A (en) | 1987-08-05 |
Family
ID=11998140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1939786A Pending JPS62178596A (en) | 1986-01-31 | 1986-01-31 | Concentration and purification of glycolipid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62178596A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001002421A3 (en) * | 1999-07-05 | 2001-07-12 | Sohkar Oy | A method for purifying phytosterol concentrates using a pressurized fluid (carbon dioxide) |
-
1986
- 1986-01-31 JP JP1939786A patent/JPS62178596A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001002421A3 (en) * | 1999-07-05 | 2001-07-12 | Sohkar Oy | A method for purifying phytosterol concentrates using a pressurized fluid (carbon dioxide) |
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