JP2019140919A - Method for producing functional material containing plasmalogen - Google Patents
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Abstract
Description
本発明は、動物組織から多量のプラズマローゲンを含む機能性素材を製造する方法に関する。 The present invention relates to a method for producing a functional material containing a large amount of plasmalogen from animal tissue.
リン脂質は、生体膜の構成成分として重要であるが、中でもエーテルリン脂質であるプラズマローゲンは、哺乳動物の生体膜のリン脂質の約１８％を占めている。このプラズマローゲンは、特に、脳神経、心筋、骨格筋、白血球、精子に多いことが知られている。 Phospholipids are important as components of biological membranes. Among them, plasmalogens, which are ether phospholipids, account for about 18% of phospholipids in mammalian biological membranes. This plasmalogen is known to be particularly abundant in cranial nerves, myocardium, skeletal muscle, leukocytes, and sperm.
プラズマローゲンは、ドコサヘキサエン酸やアラキドン酸などの多価不飽和脂肪酸と多く結合しているため、これらの多価不飽和脂肪酸から産生するプロスタグランヂンやロイコトリエンなどの細胞間シグナルの２次メッセンジャーの貯留所となっているだけでなく、細胞融合、イオン移送など重要な働きをしている。
さらに、プラズマローゲンのビニルエーテル結合（アルケニル結合）が、特に酸化ストレスに敏感であるため細胞の抗酸化の機能も果たしている。
Since plasmalogens are bound to many polyunsaturated fatty acids such as docosahexaenoic acid and arachidonic acid, they store secondary messengers of intercellular signals such as prostaglandins and leukotrienes produced from these polyunsaturated fatty acids. In addition to being a place, it plays important roles such as cell fusion and ion transport.
In addition, the vinyl ether bond (alkenyl bond) of plasmalogen is particularly sensitive to oxidative stress, and thus also functions as a cell antioxidant.
また、プラズマローゲンは、アルツハイマー病、パーキンソン病、うつ病、統合失調症などの脳神経病、糖尿病などのメタボリックシンドロームや、種々の感染症や免疫異常の治療および改善の効果において効果があるといわれている。 Plasmalogens are said to be effective in the treatment and improvement of metabolic syndrome such as Alzheimer's disease, Parkinson's disease, depression, schizophrenia, and other metabolic syndrome, as well as various infectious diseases and immune disorders. Yes.
従来より、このようなプラズマローゲンを動物組織から抽出する試みがなされている（特許文献１及び２）。例えば、特許文献１においては、レイヤーのムネ肉に対してエタノールを抽出溶媒として抽出処理し、抽出液を回収する方法が提案されている。 Conventionally, attempts have been made to extract such plasmalogens from animal tissues (Patent Documents 1 and 2). For example, Patent Document 1 proposes a method of extracting extraction liquid using ethanol as an extraction solvent for layered meat.
また、特許文献２においては、動物組織に対して、エタノール抽出処理を行い、エタノール抽出物を得、エタノール抽出物をホスホリパーゼＡ１（ＰＬＡ１）で処理し、ジアシル型グリセロリン脂質を加水分解し、さらに水溶性ケトン系溶剤で処理し、不溶部を回収し、不溶部を、脂肪族炭化水素溶剤と水溶性ケトン溶剤との混合有機溶剤、及び水で溶媒分配し、混合有機溶剤部を回収する方法が提案されている。 In Patent Document 2, ethanol extraction is performed on animal tissues to obtain an ethanol extract, the ethanol extract is treated with phospholipase A1 (PLA1), hydrolyzing diacyl glycerophospholipid, and further water-soluble. A method of recovering the mixed organic solvent part by treating with an insoluble ketone solvent, collecting the insoluble part, partitioning the insoluble part with a mixed organic solvent of an aliphatic hydrocarbon solvent and a water-soluble ketone solvent, and water. Proposed.
上記のように、有用なプラズマローゲンを動物組織から得ようとする試みはされているものの、必ずしも効率よくプラズマローゲンを得ることができているとはいえない。 Although attempts have been made to obtain useful plasmalogens from animal tissues as described above, it cannot always be said that plasmalogens can be obtained efficiently.
本発明の課題は、動物組織からプラズマローゲンを効率的に得ることができる方法を提供することにある。 An object of the present invention is to provide a method capable of efficiently obtaining plasmalogens from animal tissues.
本発明者らは、動物組織からプラズマローゲンを効率的に抽出すべく鋭意検討した結果、動物組織をプロテアーゼにより処理した後、エタノールで抽出することにより、多量のプラズマローゲンを抽出できることを見いだし、本発明を完成するに至った。 As a result of intensive studies to efficiently extract plasmalogens from animal tissues, the present inventors have found that a large amount of plasmalogens can be extracted by treating animal tissues with protease and then extracting with ethanol. The invention has been completed.
すなわち、本発明は、以下のとおりのものである。
［１］動物組織をプロテアーゼで処理する酵素処理工程と、前記プロテアーゼで処理した動物組織を、エタノールを含む抽出液で抽出する抽出工程とを有することを特徴とするプラズマローゲンを含む機能性素材の製造方法。
［２］動物組織が、ホタテ類の食用部位であることを特徴とする［１］記載のプラズマローゲンを含む機能性素材の製造方法。
［３］動物組織が、ホヤの食用部位であることを特徴とする［１］記載のプラズマローゲンを含む機能性素材の製造方法。
［４］動物組織が、鳥類の食用部位であることを特徴とする［１］記載のプラズマローゲンを含む機能性素材の製造方法。
［５］プロテアーゼが、糸状菌由来のプロテアーゼであることを特徴とする［１］〜［４］のいずれか記載のプラズマローゲンを含む機能性素材の製造方法。
［６］プロテアーゼが、麹菌由来のプロテアーゼであることを特徴とする［５］記載のプラズマローゲンを含む機能性素材の製造方法。
［７］プロテアーゼが、中性プロテアーゼであることを特徴とする［１］〜［６］のいずれか記載のプラズマローゲンを含む機能性素材の製造方法。
That is, the present invention is as follows.
[1] A functional material containing plasmalogen, comprising an enzyme treatment step for treating animal tissue with a protease, and an extraction step for extracting the animal tissue treated with the protease with an extract containing ethanol. Production method.
[2] The method for producing a functional material containing a plasmalogen according to [1], wherein the animal tissue is an edible portion of scallops.
[3] The method for producing a functional material containing plasmalogen according to [1], wherein the animal tissue is an edible portion of sea squirt.
[4] The method for producing a functional material containing plasmalogen according to [1], wherein the animal tissue is an edible part of birds.
[5] The method for producing a functional material containing a plasmalogen according to any one of [1] to [4], wherein the protease is a protease derived from a filamentous fungus.
[6] The method for producing a functional material containing a plasmalogen according to [5], wherein the protease is a koji mold-derived protease.
[7] The method for producing a functional material containing a plasmalogen according to any one of [1] to [6], wherein the protease is a neutral protease.
本発明によれば、動物組織からプラズマローゲンを効率的に抽出することができ、多量のプラズマローゲンを含む機能性素材を得ることができる。 According to the present invention, a plasmalogen can be efficiently extracted from animal tissues, and a functional material containing a large amount of plasmalogen can be obtained.
本発明のプラズマローゲンを含む機能性素材の製造方法は、動物組織をプロテアーゼで処理する酵素処理工程と、プロテアーゼで処理した動物組織を、エタノールを含む抽出液で抽出する抽出工程とを有することを特徴とする。本発明の製造方法においては、酵素処理工程及び抽出工程の前後に他の工程を有していてもよい。 The method for producing a functional material containing plasmalogen of the present invention comprises an enzyme treatment step for treating animal tissue with a protease, and an extraction step for extracting the animal tissue treated with the protease with an extract containing ethanol. Features. In the manufacturing method of this invention, you may have another process before and after an enzyme treatment process and an extraction process.
［酵素処理工程］
酵素処理工程は、動物組織をプロテアーゼで処理する工程である。
動物組織としては、プラズマローゲンを含む動物組織であれば特に制限されるものではなく、ホタテ類、ホヤ、ナマコ、アワビ、サケ、サンマ、カツオ等の水産動物や鳥類の食用部位（可食部位）を挙げることができ、これらの中でも、ホタテ類、ホヤ、鳥類の食用部位が好ましい。
[Enzyme treatment process]
The enzyme treatment step is a step of treating animal tissue with a protease.
The animal tissue is not particularly limited as long as it contains plasmalogen, and edible parts (edible parts) of marine animals and birds such as scallops, squirts, sea cucumbers, abalone, salmon, saury, skipjack, etc. Among these, edible parts of scallops, sea squirts, and birds are preferable.
本発明におけるホタテ類は、イタヤガイ科に属する食用の二枚貝をいい、例えば、Mizuhopecten属、Pecten属に属するものを挙げることができる。具体的には、日本で採取されるホタテガイ（学名：Mizuhopecten yessoensis）や、ヨーロッパで採取されるヨーロッパホタテ（学名：Pecten maximus（Linnaeus））等を挙げることができる。食用部位としては、貝柱、ひも等を挙げることができる。 The scallops in the present invention refer to edible bivalves belonging to the mussel family, and examples thereof include those belonging to the genus Mizuhopecten and Pecten. Specific examples include scallops collected in Japan (scientific name: Mizuhopecten yessoensis) and scallops collected in Europe (scientific name: Pecten maximus (Linnaeus)). Examples of edible parts include scallops and strings.
本発明におけるホヤは、マボヤ科に属する食用の脊索動物をいい、マボヤ属、アカボヤ属に属するものを挙げることができる。具体的には、マボヤ（学名：Halocynthia roretzi）や、アカボヤ（学名：Halocynthia aurantium）等を挙げることができる。食用部位としては、身の部分（筋膜体）を挙げることができる。 The sea squirt in the present invention refers to an edible chordate belonging to the family Maboyaceae, and examples thereof include those belonging to the genus Maboya and Akaboya. Specific examples include maboya (scientific name: Halocynthia roretzi) and red oyster (scientific name: Halocynthia aurantium). An edible part can include a body part (fascia).
本発明における鳥類は、食用の鳥類であれば特に制限されるものではなく、例えば、鶏、烏骨鶏、鴨等を挙げることができる。食用部位としては、プラズマローゲンを豊富に含むムネ肉が好ましい。 The bird in the present invention is not particularly limited as long as it is an edible bird, and examples thereof include chickens, rib chickens, and duck. As the edible portion, a fillet containing abundant plasmalogen is preferable.
これらの動物組織は、切断物であってもよいが、より効率的にプラズマローゲンを抽出できることから、粉砕物を用いることが好ましい。 These animal tissues may be cut products, but it is preferable to use pulverized products because plasmalogens can be extracted more efficiently.
酵素処理に用いるプロテアーゼとしては、Aspergillus属、 Rhizopus属等の糸状菌由来のプロテアーゼや、Bacillus属等の細菌由来のプロテアーゼや、パパイヤ、パイナップル等の植物から抽出されたプロテアーゼを挙げることができ、市販のプロテアーゼ剤を用いることができる。これらの中でも、糸状菌由来のプロテアーゼが好ましく、麹菌由来のプロテアーゼが特に好ましい。また、プラズマローゲンは酸性、塩基性では不安定であることから、中性プロテアーゼが好ましい。 Examples of proteases used for enzyme treatment include proteases derived from filamentous fungi such as Aspergillus and Rhizopus, proteases derived from bacteria such as Bacillus, and proteases extracted from plants such as papaya and pineapple. These protease agents can be used. Among these, a protease derived from filamentous fungi is preferable, and a protease derived from Aspergillus is particularly preferable. Moreover, since plasmalogens are unstable when acidic or basic, neutral protease is preferable.
プロテアーゼの使用量としては、例えば、動物組織１００ｇに対して、０．１〜１０．０ｇ程度であることが好ましく、０．２〜８．０ｇ程度であることがより好ましく、０．３〜５．０ｇ程度であることがさらに好ましい。 The amount of protease used is, for example, preferably about 0.1 to 10.0 g, more preferably about 0.2 to 8.0 g, and more preferably 0.3 to 5 with respect to 100 g of animal tissue. More preferably, it is about 0.0 g.
［抽出工程］
抽出工程においては、プロテアーゼで処理した動物組織を、エタノールを含む抽出液で抽出する。
[Extraction process]
In the extraction step, animal tissue treated with protease is extracted with an extract containing ethanol.
抽出工程で用いるエタノールを含む抽出液としては、含水エタノールであってもよく、エタノールと他の有機溶媒との混合物であってもよい。エタノール濃度としては、５０質量％以上であることが好ましく、８０質量％以上であることがより好ましく、９５質量％以上であることが好ましく、実質的に１００質量％であることが好ましい。 The extract containing ethanol used in the extraction step may be water-containing ethanol or a mixture of ethanol and another organic solvent. The ethanol concentration is preferably 50% by mass or more, more preferably 80% by mass or more, preferably 95% by mass or more, and substantially preferably 100% by mass.
エタノールの使用量としては、例えば、動物組織１００ｇに対して、１００〜３０００ｍＬ程度であることが好ましく、２００〜２０００ｍＬ程度であることがより好ましく、２５０〜１０００ｍＬ程度であることがさらに好ましい。なお、エタノールを用いた抽出は複数回行ってもよい。 The amount of ethanol used is, for example, preferably about 100 to 3000 mL, more preferably about 200 to 2000 mL, and further preferably about 250 to 1000 mL with respect to 100 g of animal tissue. In addition, you may perform the extraction using ethanol in multiple times.
抽出処理を行った後、固形分を除去して抽出液を回収し、必要に応じて乾燥固化することにより、本発明のプラズマローゲンを含有した機能性素材を得ることができる。なお、この抽出物に対して、プラズマローゲンの濃度を高める濃縮処理を施してもよい。 After performing the extraction treatment, the functional material containing the plasmalogen of the present invention can be obtained by removing the solid content, collecting the extract, and if necessary, drying and solidifying. In addition, you may give the concentration process which raises the density | concentration of a plasmalogen to this extract.
本発明の製造方法により得られる機能性素材中に含まれるプラズマローゲンの量としては、０．００１〜１００ｍｇ／ｇ（wet重量換算）であることが好ましく、０．１〜１０ｍｇ／ｇであることがより好ましい。 The amount of plasmalogen contained in the functional material obtained by the production method of the present invention is preferably 0.001 to 100 mg / g (in terms of wet weight), and preferably 0.1 to 10 mg / g. Is more preferable.
本発明のプラズマローゲンを含有した機能性素材は、食品、化粧品、医薬品等に含有させて用いることができる。食品としては、一般食品の他、特定保健用食品、栄養補助食品、機能性食品、サプリメント等を挙げることができる。本発明の機能性素材を含有する食品は、アトピー性皮膚炎の改善、認知症の予防又は改善、高血糖化の抑制、血中コレステロールの降下、脂質の代謝促進、抗疲労、血中アルブミン量の維持、肝機能の回復、運動時の筋肉の低下の抑制等に有効である。化粧品としては、乳液、クリーム、ローション、オイル、パック、洗顔料、クレンジング、ボディ洗浄料等を挙げることができる。本発明の機能性素材を含有する化粧品は、皺の改善や美白を目的とした皮膚老化防止に有効である。 The functional material containing the plasmalogen of the present invention can be used in foods, cosmetics, pharmaceuticals and the like. Examples of foods include foods for specified health use, dietary supplements, functional foods, supplements and the like in addition to general foods. The food containing the functional material of the present invention is improved atopic dermatitis, prevention or improvement of dementia, suppression of hyperglycemia, blood cholesterol lowering, lipid metabolism promotion, anti-fatigue, blood albumin content It is effective for maintaining the liver, restoring liver function, and suppressing muscle loss during exercise. Examples of cosmetics include emulsions, creams, lotions, oils, packs, facial cleansers, cleansings, body cleansing agents, and the like. The cosmetic containing the functional material of the present invention is effective for preventing skin aging for the purpose of improving wrinkles and whitening.
食品、化粧品等の形態は特に制限されるものではなく、例えば、錠状、カプセル状、粉末状、顆粒状、液状、粒状、棒状、板状、ブロック状、固形状、丸状、ペースト状、クリーム状、カプレット状、ゲル状、チュアブル状、スティック状等を挙げることができる。 The form of food, cosmetics, etc. is not particularly limited. For example, tablets, capsules, powders, granules, liquids, granules, rods, plates, blocks, solids, rounds, pastes, Cream, caplet, gel, chewable, stick, etc. can be mentioned.
次の手順により、各素材（ホタテ類の食用部位・鳥類の食用部位・ホヤの食用部位）からプラズマローゲンを含む組成物を抽出し、分析を行った。具体的に、ホタテ類の食用部位としては、ホタテガイ（学名：Mizuhopecten yessoensis）のひもを用いた。鳥類の食用部位としては、鶏の胸肉を用いた。ホヤの食用部位としては、マボヤ（学名：Halocynthia roretzi）の身（筋膜体）を用いた。 By the following procedure, a composition containing plasmalogen was extracted from each material (edible part of scallops, edible part of birds, edible part of sea squirts) and analyzed. Specifically, a scallop string (scientific name: Mizuhopecten yessoensis) was used as the edible part of scallops. Chicken breast was used as an edible part for birds. Maoya (scientific name: Halocynthia roretzi) body (fascia) was used as the edible portion of squirts.
１．素材（ホタテ・鶏胸肉・ホヤ）５０ｇを解凍し、ハサミで細かく切った。
２．次の試験溶液を準備した。
ａ）０．１Ｍクエン酸溶液（ｐＨ４．５）５０ｍＬのみ
ｂ）０．１Ｍクエン酸溶液（ｐＨ４．５）５０ｍＬ＋コクラーゼ（登録商標）・Ｐ顆粒（三菱ケミカルフーズ株式会社製）０．２５ｇ
ｃ）１０ｍＭ Ｔｒｉｓ−ＨＣｌ Ｂｕｆｆｅｒ（ｐＨ７．４）５０ｍＬ＋プロテアーゼＰ「アマノ」３ＳＤ（天野エンザイム株式会社製）０．２５ｇ
ｄ）１０ｍＭ Ｔｒｉｓ−ＨＣｌ Ｂｕｆｆｅｒ（ｐＨ７．４）５０ｍＬ＋プロチンＳＤ−ＮＹ１０（天野エンザイム株式会社製）１．２５ｇ
1. 50 g of material (scallops, chicken breasts, sea squirts) was thawed and cut into small pieces with scissors.
2. The following test solutions were prepared.
a) 50 mL of 0.1 M citric acid solution (pH 4.5) only b) 50 mL of 0.1 M citric acid solution (pH 4.5) + Coclase (registered trademark) · P granule (manufactured by Mitsubishi Chemical Foods) 0.25 g
c) 10 mM Tris-HCl Buffer (pH 7.4) 50 mL + Protease P “Amano” 3SD (Amano Enzyme Co., Ltd.) 0.25 g
d) 10 mM Tris-HCl Buffer (pH 7.4) 50 mL + Protin SD-NY10 (Amano Enzyme Co., Ltd.) 1.25 g
３．素材と上記ａ）〜ｄ）の各試験溶液とを混合し、ブレンダー（WARING社製HGBSS）で粉砕した（１０秒×３回）。
４．５０℃で６０分間反応させた（約１５分おきにガラス棒で攪拌した）。
５．エタノール２５０ｍＬを加え、ブレンダーに入れ粉砕した（１０秒×２回）。
６．３０分放置した（約５分ごとにガラス棒で１０回転攪拌した）。
７．吸引ろ過し、ろ液を回収した。
3. The raw material and the test solutions a) to d) were mixed and pulverized with a blender (HGBSS manufactured by WARING) (10 seconds × 3 times).
The reaction was carried out at 4.50 ° C. for 60 minutes (stirring with a glass rod about every 15 minutes).
5. Ethanol (250 mL) was added, and the mixture was pulverized in a blender (10 seconds × 2 times).
6. Allowed to stand for 30 minutes (about 10 minutes stirring with a glass rod every 5 minutes).
7). The filtrate was collected by suction filtration.
８．ろ液を１ｍＬスピッツ管に取り、リン脂質の分析に用いた。
９．残りのろ液をエバポレーターで乾固させ、総脂質重量を測定した。
8). The filtrate was taken in a 1 mL Spitz tube and used for phospholipid analysis.
9. The remaining filtrate was dried with an evaporator and the total lipid weight was measured.
各分析結果を以下に示す。
（１）総脂質重量
１）上記ａ）〜ｄ）の試験溶液を用いた抽出物の総脂質重量を表１及び図１に示す。
The results of each analysis are shown below.
(1) Total lipid weight 1) The total lipid weight of the extract using the test solutions a) to d) is shown in Table 1 and FIG.
（２）リン脂質の分析
１）上記ａ）〜ｄ）の試験溶液を用いた抽出物のリン脂質の分析条件（図２参照）における各成分の割合（ＨＰＬＣの面積値から算出）を表２に示す。
(2) Analysis of phospholipid 1) The ratio (calculated from the area value of HPLC) of each component in the phospholipid analysis conditions (see FIG. 2) of the extract using the test solutions of a) to d) above is shown in Table 2. Shown in
pl-PE：エタノラミンプラズマローゲン
PE：ホスファチジルエタノラミン
pl-PC：コリンプラズマローゲン
PC：ホスファチジルコリン
CAEP：セラミドアミノエチルホスホン酸
SM：スフィンゴミエリン
PS：ホスファチジルセリン
PI：ホスファチジルイノシトール
LPC：リゾホスファチジルコリン
pl-PE: Ethanolamine plasmalogen
PE: Phosphatidylethanolamine
pl-PC: Choline plasmalogen
PC: Phosphatidylcholine
CAEP: Ceramide aminoethylphosphonic acid
SM: Sphingomyelin
PS: Phosphatidylserine
PI: Phosphatidylinositol
LPC: Lysophosphatidylcholine
２）リン脂質の分析条件におけるプラズマローゲン（pl-PE＋pl-PC）の割合を表３及び図３に示す。 2) The ratio of plasmalogen (pl-PE + pl-PC) under the phospholipid analysis conditions is shown in Table 3 and FIG.
（３）プロテアーゼ処理によるプラズマローゲン（pl-PE＋pl-PC）の増加率
上記（１）で求めた総脂質量に、上記（２）２）で求めたプラズマローゲン（pl-PE＋pl-PC）の割合をかけた数値を算出し、「ａ）プロテアーゼなし」を基準（１．０）として、プラズマローゲン（pl-PE＋pl-PC）の量を比較した。その結果を表４及び図４に示す。
なお、総脂質全体に占めるリン脂質の割合は、プロテアーゼ処理を施してもほぼ変化はなかった。
(3) Increase rate of plasmalogen (pl-PE + pl-PC) by protease treatment Ratio of plasmalogen (pl-PE + pl-PC) determined in (2) 2) above to the total lipid content determined in (1) above The amount of plasmalogen (pl-PE + pl-PC) was compared using “a) no protease” as the standard (1.0). The results are shown in Table 4 and FIG.
The proportion of phospholipids in the total lipid was almost unchanged even after protease treatment.
表４に示すように、プロテアーゼ処理を施すことにより、プラズマローゲンの抽出量が飛躍的に増加することがわかる。
As shown in Table 4, it can be seen that the amount of plasmalogen extracted increases dramatically by the protease treatment.
本発明の製法により製造されるプラズマローゲンを含む機能性素材は、食品や化粧品に用いることができることから、産業上有用である。 Since the functional material containing plasmalogen produced by the production method of the present invention can be used for foods and cosmetics, it is industrially useful.
Claims (7)
前記プロテアーゼで処理した動物組織を、エタノールを含む抽出液で抽出する抽出工程と、
を有することを特徴とするプラズマローゲンを含む機能性素材の製造方法。 An enzyme treatment step of treating animal tissue with a protease;
An extraction step of extracting the animal tissue treated with the protease with an extract containing ethanol;
A method for producing a functional material containing a plasmalogen, comprising:
The method for producing a functional material containing a plasmalogen according to any one of claims 1 to 6, wherein the protease is a neutral protease.
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