JP5155595B2 - Purification method for polyphenol-containing composition, and polyphenol-containing composition purified by the purification method - Google Patents
Purification method for polyphenol-containing composition, and polyphenol-containing composition purified by the purification method Download PDFInfo
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Description
本発明は、ポリフェノールを含有する組成物を、活性炭を用いて精製する方法であり、また該精製方法により精製されたポリフェノール含有組成物に関する。 The present invention is a method for purifying a composition containing polyphenol using activated carbon, and also relates to a polyphenol-containing composition purified by the purification method.
カテキンに代表されるポリフェノール類は、近年健康機能素材として最も注目を集めている素材であり、種々の生理機能効果が開発されてきている（例えばコレステロール***促進に関する特許文献１参照）。
また、カテキン類や他のポリフェノール類自体を利用して、各種の植物抽出物を用い、飲食品の呈味改善や、劣化防止を図る手法も提案されてきている（呈味改善効果については、例えば特許文献２、３参照、劣化防止効果については例えば特許文献４〜７）。
このようにポリフェノール類は有用である反面、沈殿や着色など、飲食品の品質に大きく影響を与えかねない問題点を有している。
Polyphenols represented by catechin are materials that have attracted the most attention as health functional materials in recent years, and various physiological function effects have been developed (see, for example, Patent Document 1 regarding promotion of cholesterol excretion).
In addition, catechins and other polyphenols themselves are used to improve the taste of foods and beverages using various plant extracts and to prevent deterioration (for the taste improvement effect, For example, see Patent Documents 2 and 3, and Patent Documents 4 to 7 for the deterioration prevention effect.
Thus, polyphenols are useful, but have problems that may greatly affect the quality of food and drink such as precipitation and coloring.
ポリフェノール類の精製技術としては、例えばカテキン類を含水の有機溶媒中で、特定の活性炭で処理することを特徴とする技術が提案されているが（特許文献８参照）、必ずしも実効性のあるものともいえなかった。 As a technique for purifying polyphenols, for example, a technique characterized by treating catechins with specific activated carbon in an organic solvent containing water has been proposed (see Patent Document 8), but it is always effective. I couldn't say it.
本発明が解決しようとする課題は、簡便で、しかも人体に害のないで安全性に優れた、ポリフェノール類（ポリフェノール含有組成物）の精製方法を提供することである。 The problem to be solved by the present invention is to provide a method for purifying polyphenols (polyphenol-containing composition) that is simple, harmless to the human body and excellent in safety.
本発明者らは上記課題を解決すべく鋭意研究を重ねた結果、意外にも低温処理した活性炭で精製を行えば、それのみでポリフェノール類の脱色を効果的に達成し、また、精製後のポリフェノール類は風味も優れていることを見出し本発明を完成した。 As a result of intensive studies to solve the above-mentioned problems, the present inventors have surprisingly achieved the decolorization of polyphenols only by purifying with low-temperature-treated activated carbon. The present inventors have found that polyphenols are excellent in flavor and completed the present invention.
すなわち本発明は、
（１）ポリフェノールを含有する組成物を、予め低温処理した活性炭に接触させて処理することを特徴とする、ポリフェノール含有組成物の精製方法であり；
（２）−３０〜５℃の温度条件下で０.５〜２４時間保持することにより低温処理した活性炭を使用することを特徴とする（１）記載の精製方法であり：
（３）ポリフェノールを含有する組成物が、植物抽出物又は果汁であることを特徴とする（１）又は（２）に記載の精製方法であり；
（４）ポリフェノールが、カテキンであることを特徴とする（１）又は（２）に記載の精製方法であり；
（５）（１）〜（４）のいずれかに記載の精製方法により精製して得られたことを特徴とするポリフェノール含有組成物、である。
That is, the present invention
(1) A method for purifying a polyphenol-containing composition, which comprises treating a composition containing polyphenol with activated carbon previously subjected to low temperature treatment;
(2) The purification method according to (1), wherein the activated carbon treated at a low temperature by being held at a temperature of 30 to 5 ° C. for 0.5 to 24 hours is used:
(3) The purification method according to (1) or (2), wherein the composition containing polyphenol is a plant extract or fruit juice;
(4) The purification method according to (1) or (2), wherein the polyphenol is catechin;
(5) A polyphenol-containing composition obtained by purification by the purification method according to any one of (1) to (4).
本発明のポリフェノール含有組成物の精製方法によれば、安全性に優れ、ポリフェノール含量を損なうことなく、効果的に脱色が行えるとともに、不快な味が除去され、沈殿の少ない、風味に優れたポリフェノール含有組成物を提供することができる。 According to the method for purifying a polyphenol-containing composition of the present invention, the polyphenol is excellent in safety, can be effectively decolored without impairing the polyphenol content, has an unpleasant taste removed, has less precipitation, and has a good flavor. A containing composition can be provided.
以下、本発明をさらに詳細に説明する。
本発明における活性炭の「低温処理」とは、冷凍庫等の低温化装置で、活性炭を１０℃以下の温度域で所定時間保持することをいい、通常は−５０〜１０℃で２０分〜４８時間、好ましくは−３０〜５℃で０.５分〜２４時間、さらに好ましくは−２５〜０℃で１〜１２時間、最も好ましくは−２０〜−５℃で２〜８時間行う。
Hereinafter, the present invention will be described in more detail.
The “low-temperature treatment” of activated carbon in the present invention means that the activated carbon is kept at a temperature range of 10 ° C. or lower for a predetermined time in a low-temperature apparatus such as a freezer, usually at −50 to 10 ° C. for 20 minutes to 48 hours. The reaction is preferably performed at −30 to 5 ° C. for 0.5 minute to 24 hours, more preferably at −25 to 0 ° C. for 1 to 12 hours, and most preferably at −20 to −5 ° C. for 2 to 8 hours.
本発明において使用される「活性炭」については、特に限定されることなく、市場に流通している活性炭全般を広く使用することができるが、好ましくは水分含有量が５０質量％以下のものが使用される。水分含量が５０質量％を超える場合、低温処理中に含有される水分が結晶化を起こすことにより本発明の効果が阻害される場合もありうるからである。
発明で使用する活性炭の炭素質材料としては、椰子殻、パーム椰子、果実の種、鋸屑、ユーカリ、松などの植物系、石炭系、石油系のコークス及びそれらを原料としたピッチの炭化物、フェノール樹脂、塩化ビニル樹脂、塩化ビニリデン樹脂などをあげることができるが、好ましくは椰子殻、パーム椰子、果実の種、鋸屑、ユーカリ、松などの植物系材料由来のものが用いられる。
また、薬品と水蒸気を使って賦活され、顆粒状で、比表面積が１０００ｍ2／ｇ前後の活性炭が好適である。
本発明に使用される活性炭としては、例えば、フタムラ化学社製「Ｓ又はＳＧ」、クラレケミカル社製「クラレコール（商品名）」、味の素ファインテクノ社製「ＣＬ」などが例示されるが、植物系材料由来のものであることと、経済的観点から、好ましくはフタムラ化学社製「Ｓ又はＳＧ」が用いられる。
The “activated carbon” used in the present invention is not particularly limited and can be widely used on the market in general. Preferably, activated carbon having a water content of 50% by mass or less is used. Is done. This is because when the water content exceeds 50% by mass, the water contained during the low-temperature treatment may cause crystallization, thereby inhibiting the effects of the present invention.
Carbonaceous materials for activated carbon used in the invention include plant shells such as coconut husk, palm coconut, fruit seeds, sawdust, eucalyptus, pine, etc. Examples thereof include resins, vinyl chloride resins, vinylidene chloride resins, and those derived from plant-based materials such as coconut shell, palm coconut, fruit seed, sawdust, eucalyptus, pine, etc. are preferably used.
Further, activated carbon activated with chemicals and water vapor, granular, and a specific surface area of about 1000 m 2 / g is preferable.
Examples of the activated carbon used in the present invention include “S or SG” manufactured by Phutamura Chemical Co., “Kuraray Coal (trade name)” manufactured by Kuraray Chemical Co., “CL” manufactured by Ajinomoto Fine Techno Co., etc. From the viewpoint of being derived from a plant material and economically, “S or SG” manufactured by Phutamura Chemical Co., Ltd. is preferably used.
本発明の精製方法の適用対象である「ポリフェノールを含有する組成物」とは、カテキン、アントシアニン、フラボノイド、タンニン、クロロゲン酸等のポリフェノール類を含有するものであれば特に限定されるものではない。
上記ポリフェノール類の希釈製剤のほか、各種天然抽出物、特に植物抽出物が適用の対象となり、具体的には茶類抽出物、生コーヒー豆抽出物、ヒマワリ種子抽出物、ブドウ種子抽出物、ブルーベリー葉抽出物、ペパー抽出物、ホウセンカ抽出物、ヤマモモ抽出物、ユーカリ葉抽出物、アズキ全草抽出物、エンジュ抽出物、ソバ全草抽出物、ローズマリー抽出物及び各種果汁が例示される。
好ましくは、茶類抽出物、生コーヒー豆抽出物、ヒマワリ種子抽出物、ブドウ種子抽出物、ブルーベリー葉抽出物、ペパー抽出物、ホウセンカ抽出物、ヤマモモ抽出物、ユーカリ葉抽出物、アズキ全草抽出物、エンジュ抽出物、ソバ全草抽出物、ローズマリー抽出物及び各種果汁であり、さらに好ましくは、茶類抽出物、生コーヒー豆抽出物、ヒマワリ種子抽出物、ヤマモモ抽出物及び各種果汁であり、最も好ましくは、茶類抽出物及び各種果汁である。
The “composition containing polyphenol” to which the purification method of the present invention is applied is not particularly limited as long as it contains polyphenols such as catechin, anthocyanin, flavonoid, tannin and chlorogenic acid.
In addition to the above-mentioned dilute preparations of polyphenols, various natural extracts, particularly plant extracts, are applicable. Specifically, tea extracts, fresh coffee bean extracts, sunflower seed extracts, grape seed extracts, blueberries Examples are leaf extract, pepper extract, spinach extract, bayberry extract, eucalyptus leaf extract, azuki bean extract, enju extract, buckwheat extract, rosemary extract and various fruit juices.
Preferably, tea extract, green coffee bean extract, sunflower seed extract, grape seed extract, blueberry leaf extract, pepper extract, spinach extract, bayberry extract, eucalyptus leaf extract, azuki bean whole plant extract , Enju extract, buckwheat whole plant extract, rosemary extract and various fruit juices, more preferably tea extract, fresh coffee bean extract, sunflower seed extract, bayberry extract and various fruit juices Most preferred are tea extracts and various fruit juices.
本発明に用いられる「ポリフェノールを含有する組成物」が固体、粉末あるいはペースト状である場合は、溶媒で希釈して活性炭処理に供せられる。この場合に用いられる溶媒は、含有するポリフェノールを溶解し、かつ水溶性溶媒であれば特に限定されることなく用いられる。
本発明に用いることのできる溶媒を例示すると、例えば水、メタノール、エタノール、プロパノール、プロピレングリコール、グリセリン、１,３−ブチレングリコール等若しくはこれらの溶媒の混合物が例示され、好ましくは、水、エタノール、水−エタノール混合溶媒が用いられる。
本発明の具体的精製方法としては、例えば精製対象品に対して低温処理した活性炭を０.１〜１０質量％添加し、５〜４０℃で、３０分〜３時間、攪拌することにより、対象品を活性炭に接触させて着色性物質や沈殿性物質等の不純物を吸着処理することにより達成される。本発明においては、低温処理活性炭は低温状態で保管して用いられる。一旦低温処理した活性炭であっても、常温で保管された場合は効果を失う可能性がある。
When the “composition containing polyphenol” used in the present invention is a solid, powder or paste, it is diluted with a solvent and subjected to activated carbon treatment. The solvent used in this case is not particularly limited as long as it dissolves the contained polyphenol and is a water-soluble solvent.
Examples of the solvent that can be used in the present invention include water, methanol, ethanol, propanol, propylene glycol, glycerin, 1,3-butylene glycol and the like, or a mixture of these solvents, preferably water, ethanol, A water-ethanol mixed solvent is used.
As a specific purification method of the present invention, for example, 0.1 to 10% by mass of low-temperature-treated activated carbon is added to a product to be purified, and stirred at 5 to 40 ° C. for 30 minutes to 3 hours. This is achieved by bringing the product into contact with activated carbon and adsorbing impurities such as coloring substances and precipitating substances. In the present invention, the low-temperature activated carbon is stored and used at a low temperature. Even activated carbon that has been subjected to low temperature treatment may lose its effect when stored at room temperature.
本発明のポリフェノール含有組成物の精製方法によれば、精製前のポリフェノール含量を損なうことなく効果的に脱色が行えるとともに、不快な味が除去され、沈殿の少ない風味に優れたポリフェノール含有組成物を得ることができる。
したがって当該ポリフェノール含有組成物を各種飲食物に添加することにより、沈殿などの発生を伴わず、さらにはその風味を損なうことなく、各種ポリフェノールの有する機能性を付与することができる。
本発明の精製方法により精製されたポリフェノール含有組成物は、飲食品の加工段階で適宜添加することができ、添加量はポリフェノール含有組成物の性状により異なるが、一般的には飲食品に対して０.０１〜１００質量％、好ましくは０.１〜１０質量％の添加量（固形成分として）が適当である。
According to the method for purifying a polyphenol-containing composition of the present invention, a polyphenol-containing composition excellent in flavor with reduced unpleasant taste and less precipitation can be effectively removed without impairing the polyphenol content before purification. Can be obtained.
Therefore, by adding the polyphenol-containing composition to various foods and drinks, the functionality of various polyphenols can be imparted without causing precipitation or the like and without impairing the flavor.
The polyphenol-containing composition purified by the purification method of the present invention can be appropriately added at the processing stage of the food and drink, and the addition amount varies depending on the properties of the polyphenol-containing composition, but generally for food and drink. An addition amount (as a solid component) of 0.01 to 100% by mass, preferably 0.1 to 10% by mass is appropriate.
本発明の精製方法により精製されたポリフェノール含有組成物は、以下のとおり、各種飲食品に幅広く、特に制限なく使用することができる。
例えば、果実類またはその加工品、野菜またはその加工品、魚介類またはその加工品、練製品、調理食品、総菜類、スナック類、珍味類、加工食品、栄養食品、茶飲料およびコーヒー飲料などの嗜好飲料、果汁飲料、炭酸飲料、清涼飲料、機能性飲料、アルコール飲料、アイスクリーム、シャーベット等の冷菓類、ゼリー、プリン、羊かん等のデザート類、クッキー、ケーキ、チョコレート、チューイングガム、饅頭等の菓子類、菓子パン、食パン等のパン類、ジャム類、ラムネ、タブレット、錠菓類などがあげられる。
さらに、日本料理のだし、例えば、鰹節、魚介類、昆布、シイタケ、鶏肉、野菜類などのだし汁および和風調味料、または、西洋料理のスープストック、例えば、牛肉、鶏肉、豚肉、魚介類、野菜類などのだし汁および洋風調味料、または、中華料理のタン（湯）、例えば、牛肉、鶏肉、豚肉、魚介類、野菜類などからとったスープおよび中華調味料などがあげられる。
また、茶類抽出物は、適宜、香味成分あるいは色素を調合し、香味および色調を増強することもできる。調合に使用される香味成分あるいは色素には特に制限はなく、公知の香味成分あるいは色素が目的に応じて適宜配合して用いられる。
The polyphenol-containing composition purified by the purification method of the present invention is widely used for various foods and drinks as follows, and can be used without particular limitation.
For example, fruits or processed products thereof, vegetables or processed products thereof, seafood or processed products thereof, paste products, cooked foods, prepared vegetables, snacks, delicacies, processed foods, nutritional foods, tea drinks and coffee drinks Taste drinks, fruit juice drinks, carbonated drinks, soft drinks, functional drinks, alcoholic drinks, ice cream, confectionery such as sherbet, desserts such as jelly, pudding, sheep cane, cookies, cakes, chocolate, chewing gum, buns, etc. , Breads such as confectionery bread and bread, jams, ramunes, tablets and tablet confectionery.
In addition, soup stock of Japanese cuisine, such as bonito, seafood, kelp, shiitake, chicken, vegetables, etc., or soup stock of Western cuisine, eg, beef, chicken, pork, seafood, vegetables Soup and Chinese seasonings such as soup taken from soup stock and soy sauces such as seafood, or tang (hot water) of Chinese cuisine such as beef, chicken, pork, seafood, vegetables and the like.
In addition, the tea extracts can be appropriately mixed with flavor components or pigments to enhance the flavor and color tone. There is no restriction | limiting in particular in the flavor component or pigment | dye used for preparation, A well-known flavor component or pigment | dye is suitably mix | blended and used according to the objective.
以下に実施例を挙げて本発明を具体的に説明するが、本発明は実施例の記載に限定されるものではない。 EXAMPLES The present invention will be specifically described below with reference to examples, but the present invention is not limited to the description of the examples.
［調製例１］
市販の活性炭（フタムラ化学社製「ＳＧ」）を冷凍庫に保存し、−１５℃で８時間処理することにより本発明に使用する活性炭Ａを得た。
この活性炭Ａを使用する直前まで冷蔵保管（５℃）し、以下の試験例に供した。
[Preparation Example 1]
Commercially available activated carbon (“SG” manufactured by Futamura Chemical Co., Ltd.) was stored in a freezer and treated at −15 ° C. for 8 hours to obtain activated carbon A used in the present invention.
The activated carbon A was refrigerated (5 ° C.) until just before use, and used for the following test examples.
［調製例２］
市販の活性炭（フタムラ化学社製「ＳＧ」）を冷凍庫に保存し、５℃で８時間処理することにより本発明に使用する活性炭Ｂを得た。
この活性炭Ｂを使用する直前まで冷蔵保管（５℃）し、以下の試験例に供した。
[Preparation Example 2]
Commercially available activated carbon (“SG” manufactured by Futamura Chemical Co., Ltd.) was stored in a freezer and treated at 5 ° C. for 8 hours to obtain activated carbon B used in the present invention.
The activated carbon B was refrigerated (5 ° C.) until just before use, and used for the following test examples.
［比較品１］
市販の活性炭（フタムラ化学社製「ＳＧ」）を室温（２１〜２８℃）で保存し、比較品の活性炭Ｃとし、以下の試験例に供した。
[Comparative product 1]
Commercially available activated carbon (“SG” manufactured by Futamura Chemical Co., Ltd.) was stored at room temperature (21 to 28 ° C.) to obtain activated carbon C as a comparative product, which was used in the following test examples.
［実施例１］
市販のカテキン製剤（三井農林社製「ポリフェノン７０（登録商標）」）を５０％エタノール水溶液に溶解し、ポリフェノール含量１０％のポリフェノール含有液を調製した（コントロール）。このものに、調製例１の活性炭Ａを１質量％添加し、３０分常温にて攪拌後、活性炭をろ過除去することにより、ポリフェノール含有組成物を得た。
得られたポリフェノール含有組成物の色調（450nm吸光度）、ポリフェノール含量を表１に示した。
[Example 1]
A commercially available catechin preparation (“Polyphenon 70 (registered trademark)” manufactured by Mitsui Norin Co., Ltd.) was dissolved in a 50% ethanol aqueous solution to prepare a polyphenol-containing liquid having a polyphenol content of 10% (control). To this, 1% by mass of activated carbon A of Preparation Example 1 was added, stirred for 30 minutes at room temperature, and then the activated carbon was removed by filtration to obtain a polyphenol-containing composition.
Table 1 shows the color tone (absorbance at 450 nm) and polyphenol content of the obtained polyphenol-containing composition.
［実施例２］
市販のカテキン製剤（三井農林社製「ポリフェノン７０（登録商標）」）を５０％エタノール水溶液に溶解し、ポリフェノール含量１０％のポリフェノール含有液を調製した（コントロール）。このものに、調製例２の活性炭Ｂを１質量％添加し、３０分常温にて攪拌後、活性炭をろ過除去することにより、ポリフェノール含有組成物を得た。
得られたポリフェノール含有組成物の色調（450nm吸光度）、ポリフェノール含量を表１に示した。
[Example 2]
A commercially available catechin preparation (“Polyphenon 70 (registered trademark)” manufactured by Mitsui Norin Co., Ltd.) was dissolved in a 50% ethanol aqueous solution to prepare a polyphenol-containing liquid having a polyphenol content of 10% (control). To this, 1% by mass of activated carbon B of Preparation Example 2 was added, and after stirring at room temperature for 30 minutes, the activated carbon was removed by filtration to obtain a polyphenol-containing composition.
Table 1 shows the color tone (absorbance at 450 nm) and polyphenol content of the obtained polyphenol-containing composition.
［比較例１］
市販のカテキン製剤（三井農林社製「ポリフェノン７０（登録商標）」）を５０％エタノール水溶液に溶解し、ポリフェノール含量１０％のポリフェノール含有液を調製した（コントロール）。このものに、比較品１の活性炭Ｃを１質量％添加し、３０分常温にて攪拌後、活性炭をろ過除去することにより、ポリフェノール含有組成物を得た。
得られたポリフェノール含有組成物の色調（450nm吸光度）、固形あたりのポリフェノール含量を表１に示した。
[Comparative Example 1]
A commercially available catechin preparation (“Polyphenon 70 (registered trademark)” manufactured by Mitsui Norin Co., Ltd.) was dissolved in a 50% ethanol aqueous solution to prepare a polyphenol-containing liquid having a polyphenol content of 10% (control). 1 mass% of the activated carbon C of the comparative product 1 was added to this, and after stirring at room temperature for 30 minutes, the activated carbon was removed by filtration to obtain a polyphenol-containing composition.
Table 1 shows the color tone (450 nm absorbance) of the obtained polyphenol-containing composition and the polyphenol content per solid.
［実施例３］
市販のグレープフルーツ果汁（ガットフーズ社製「Ｂｘ．４２」）に、調製例１の活性炭Ａを１質量％添加し、３０分常温にて攪拌後、活性炭をろ過除去することにより、本発明のポリフェノール含有組成物（グレープフルーツ果汁Ａ）を得た。
[Example 3]
The polyphenol of the present invention is obtained by adding 1% by mass of activated carbon A of Preparation Example 1 to commercially available grapefruit juice (“Bx.42” manufactured by Gat Foods), stirring the mixture at room temperature for 30 minutes, and filtering off the activated carbon. A containing composition (grapefruit juice A) was obtained.
［実施例４］
市販のグレープフルーツ果汁（ガットフーズ社製「Ｂｘ．４２」）に、調製例２の活性炭Ｂを１質量％添加し、３０分常温にて攪拌後、活性炭をろ過除去することにより、本発明のポリフェノール含有組成物（グレープフルーツ果汁Ｂ）を得た。
[Example 4]
The polyphenol of the present invention is obtained by adding 1% by mass of activated carbon B of Preparation Example 2 to commercially available grapefruit juice (“Bx.42” manufactured by Gat Foods), stirring the mixture at room temperature for 30 minutes, and removing the activated carbon by filtration. The containing composition (grapefruit juice B) was obtained.
［比較例２］
市販のグレープフルーツ果汁（ガットフーズ社製「Ｂｘ．４２」）に、比較品１の活性炭Ｃを１質量％添加し、３０分常温にて攪拌後、活性炭をろ過除去することにより、本発明のポリフェノール含有組成物（グレープフルーツ果汁Ｃ）を得た。
[Comparative Example 2]
The polyphenol of the present invention is obtained by adding 1% by mass of the activated carbon C of the comparative product 1 to commercially available grapefruit juice (“Bx.42” manufactured by Gat Foods Co., Ltd.), stirring the mixture at room temperature for 30 minutes, and then filtering off the activated carbon. The containing composition (grapefruit juice C) was obtained.
［試験例１］
実施例３、実施例４及び比較例２のグレープフルーツ果汁について、評価を行った。評価項目は色調（450nm吸光度）及び香味評価とし、香味評価は、訓練されたパネラー５人の官能試験による自由記述とした。評価結果のまとめを表２に示した。
[Test Example 1]
The grapefruit juice of Example 3, Example 4 and Comparative Example 2 was evaluated. The evaluation items were color tone (absorbance at 450 nm) and flavor evaluation, and the flavor evaluation was freely described by a sensory test of five trained panelists. A summary of the evaluation results is shown in Table 2.
表１及び表２の結果から、本発明の精製方法による効果は明らかである。 From the results in Tables 1 and 2, the effect of the purification method of the present invention is clear.
本発明のポリフェノール含有組成物の精製方法によれば、ポリフェノール含量を損なうことなく効果的に脱色が行えるとともに、不快な味が除去され、沈殿の少ない風味に優れたポリフェノール含有組成物を得ることができる。 According to the method for purifying a polyphenol-containing composition of the present invention, it is possible to effectively remove the color without impairing the polyphenol content, remove an unpleasant taste, and obtain a polyphenol-containing composition excellent in flavor with less precipitation. it can.
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