JP2001046037A - Method for reducing astringent taste of proanthocyanidin - Google Patents
Method for reducing astringent taste of proanthocyanidinInfo
- Publication number
- JP2001046037A JP2001046037A JP11228182A JP22818299A JP2001046037A JP 2001046037 A JP2001046037 A JP 2001046037A JP 11228182 A JP11228182 A JP 11228182A JP 22818299 A JP22818299 A JP 22818299A JP 2001046037 A JP2001046037 A JP 2001046037A
- Authority
- JP
- Japan
- Prior art keywords
- astringency
- proanthocyanidin
- protein
- polysaccharide
- reducing
- 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
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- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は植物体を抽出して得られ
るプロアントシアニジンを主成分とする抽出物の渋味を
低減させる方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for reducing the astringency of an extract containing proanthocyanidin as a main component obtained by extracting a plant.
【０００２】[0002]
【従来の技術】例えばブドウの種子、皮、搾汁粕あるい
は樹皮や豆類等の植物体を抽出して得られるプロアント
シアニジンは強い抗酸化作用を有しており食品等の抗酸
化剤として利用されている。また種々の生理活性も有す
るところから、最近では健康食品素材として利用されて
いる。プロアントシアニジンは、ポリフェノールの1種
で次式2. Description of the Related Art Proanthocyanidins obtained by extracting plants such as grape seeds, bark, squeezed lees or bark and beans have a strong antioxidant action and are used as antioxidants in foods and the like. ing. Also, since it has various physiological activities, it is recently used as a health food material. Proanthocyanidins are a type of polyphenol and have the formula
【０００３】[0003]
【化１】 （式中Ｒ1は水素原子又は水酸基、Ｒ2、Ｒ6はそれぞれ
独立に水素原子、水酸基又はメトキシ基、Ｒ4、Ｒ3、Ｒ
7、Ｒ8はそれぞれ独立に水酸基又はメトキシ基、Ｒ5は
ガロイル基又はグルコピラノシル基を示す）で表され
る、フラバン-3-オールまたはフラバン-3,4-ジオールを
構成単位として、4-6位又は4-8位で縮合もしくは重合に
より結合した化合物群であり、各種植物体中に存在する
縮合型タンニンである。なお化１は、理解を助けるため
に4-8位で縮合した場合だけを示している。これらは酸
処理によりシアニジン、デルフィニジン、ペラルゴニジ
ン等のアントシアニジンを生成するところから、この名
称が与えられているものである。そして上記構成単位の
２量体、３量体、４量体さらに１０〜３０量体以上の高
分子のプロシアニジン、プロデルフィニジン、プロペラ
ルゴニジン等のプロアントシアニジンおよびそれらの立
体異性体等を含むものである。Embedded image (Wherein R 1 is a hydrogen atom or a hydroxyl group, R 2 and R 6 are each independently a hydrogen atom, a hydroxyl group or a methoxy group, R 4 , R 3 , R
7 and R 8 each independently represent a hydroxyl group or a methoxy group, and R 5 represents a galloyl group or a glucopyranosyl group), represented by flavan-3-ol or flavan-3,4-diol as a constituent unit. A group of compounds linked by condensation or polymerization at the 4th or 4th to 8th positions, and are condensed tannins present in various plants. In addition, chemical formula 1 shows only the case where condensation is performed at the 4-8 position to facilitate understanding. These are given the name because they produce anthocyanidins such as cyanidin, delphinidin and pelargonidin by acid treatment. The dimer, the trimer, the tetramer, and the 10 to 30-mer or more of the above structural units include proanthocyanidins such as procyanidin, prodelphinidin, and properargonidine, and stereoisomers thereof.
【０００４】しかしながらプロアントシアニジンには独
特の強い渋味があるため、抗酸化剤として食品に添加す
る場合、自ずとその量が制限され、あるいは健康食品と
してこれを食する場合、口腔内にひどいしびれを伴う不
快感を生ずるため、大量のプロアントシアニジンをその
まま摂取することは、極めて困難である。However, since proanthocyanidin has a unique strong astringency, its amount is naturally restricted when added to food as an antioxidant, or when it is eaten as a health food, severe numbness in the oral cavity is caused. It is extremely difficult to take large quantities of proanthocyanidins as they are due to the accompanying discomfort.
【０００５】このようなことからプロアントシアニジン
を主成分とする健康食品分野においては錠剤（糖衣錠も
含む）あるいはカプセルの形態が多く、粉剤や顆粒剤タ
イプの製品は見当たらない。[0005] For these reasons, in the field of health foods containing proanthocyanidin as a main component, there are many forms of tablets (including sugar-coated tablets) or capsules, and powder or granule type products are not found.
【０００６】ところで、医薬等の分野において苦味の低
減化方法が種々提案されているが、「渋味」は「辛味」
と同じ様に味覚とは異なり、味蕾以外の箇所（例えば口
腔内壁、舌裏部など）でも感じることのできる感覚で、
触覚や痛覚と同種のものである。すなわち味覚である苦
味の低減方法は、触覚や痛覚に近い渋味の低減には利用
できないのである。またタンニン系の「渋味食品」の代
表格は柿渋タンニンであるが、古くより柿渋の脱渋方法
として「焼酎・アルコール抜き」「湯抜き」「ドライア
イス・炭酸ガス抜き」「肺汁抜き」などが知られてい
る。しかしこれらは、柿果実の細胞に嫌気的呼吸をさせ
てアセトアルデヒドを発生させ、これが柿渋タンニンを
重合させ、その結果タンニンが不溶性化することによる
渋抜きであって、あらかじめ抽出した高濃度のプロアン
トシアニジンの渋味をこの方法により低減することは不
可能である。その他のタンニン系渋味を含有する食品の
渋味低減方法としては、紅茶にアルカリ処理ゼラチンを
添加してゼリー化する方法（特開平4-49984号）、タン
ニン等の渋味成分を含む食品にプロタミンを添加する方
法（特開平5-328935号、6-153875号）、酵素で渋味成分
をグリコシル化する方法（特開平7-327602号、特公平6-
88908号）、樹脂や活性炭で渋味成分を吸着除去する方
法（特開平8-173084号、9-220055号、11-103817号）、
サイクロデキストリンを用いたマスキング法（特開平7-
327602号、9-309902号、10-4919号）などが提案されて
いる。しかしこれらはいずれもごく少量含まれているタ
ンニンの渋味をマスクする方法やタンニン自体を除去し
てしまう方法、あるいは高価だったり一般的には使用さ
れていない物質を添加する方法などであり、プロアント
シアニジンの量的な損失を伴わず、安価で効率よく、し
かも安全な方法で渋味を低減する方法はこれまで知られ
ていない。[0006] By the way, various methods for reducing bitterness have been proposed in the field of medicine and the like.
In the same way as the taste, unlike the taste buds, it can be felt in places other than taste buds (for example, the inner wall of the mouth, the back of the tongue, etc.)
It is akin to tactile and painful sensations. That is, the method of reducing bitterness, which is the taste, cannot be used to reduce astringency close to touch or pain. A typical example of tannin-based "astringent food" is persimmon astringent tannin. Etc. are known. However, in these, persimmon fruit cells undergo anaerobic respiration to generate acetaldehyde, which polymerizes persimmon astringent tannins, resulting in insolubilization of the tannins. It is not possible to reduce the astringency of this product by this method. Other methods of reducing the astringency of foods containing a tannin-based astringency include a method of adding an alkali-treated gelatin to black tea to form a jelly (JP-A-4-49984), and a method of reducing the astringency of foods containing astringent components such as tannin. A method of adding protamine (JP-A-5-328935, JP-A-6-138875), a method of glycosylating astringent components with an enzyme (JP-A-7-327602, JP-B-6-327602)
88908), a method of adsorbing and removing astringent components with a resin or activated carbon (JP-A-8-173084, 9-220055, 11-103817),
Masking method using cyclodextrin
327602, 9-309902, and 10-4919) have been proposed. However, all of these are methods of masking the astringency of tannin contained in a very small amount, methods of removing tannin itself, or methods of adding expensive or generally unused substances, There has been no known method for reducing the astringency in a safe, inexpensive, efficient, and safe manner without the loss of proanthocyanidins.
【０００７】[0007]
【発明が解決しようとする課題】以上のような状況か
ら、本発明の課題は植物体を抽出して得られるプロアン
トシアニジンを主成分とする抽出物の渋味を低減する方
法を提供することにある。SUMMARY OF THE INVENTION In view of the above circumstances, an object of the present invention is to provide a method for reducing the astringency of proanthocyanidin-based extracts obtained by extracting plants. is there.
【０００８】[0008]
【課題を解決するための手段】本発明者らは前記課題を
解決するために、鋭意検討を重ねた結果、植物体を抽出
して得られるプロアントシアニジンを主成分とする抽出
物に特定のタンパク質又は多糖類を添加することによ
り、プロアントシアニジンの渋味が顕著に低減できるこ
とを見出し、本発明を完成するに至った。Means for Solving the Problems The present inventors have conducted intensive studies in order to solve the above-mentioned problems, and as a result, have found that an extract containing proanthocyanidin as a main component obtained by extracting a plant body has a specific protein content. Alternatively, they have found that the addition of polysaccharides can significantly reduce the astringency of proanthocyanidins, and have completed the present invention.
【０００９】以下本発明を詳細に説明する。まず本発明
の対象となる植物体を抽出して得られるプロアントシア
ニジンを主成分とする抽出物とは、ブドウ、柿、リン
ゴ、松、大豆、小豆など植物体を水や有機溶媒で抽出し
て得られる抽出物であり、その主成分はプロアントシア
ニジンである。中でも含有量が多いことや糖類などの夾
雑物の含量も少ないため、高純度のプロアントシアニジ
ンが抽出によって容易に得られることから、ブドウ種子
抽出物が好適である。Hereinafter, the present invention will be described in detail. First, a proanthocyanidin-based extract obtained by extracting a plant object of the present invention is a grape, a persimmon, an apple, a pine, a soybean, a soybean, a plant such as red bean is extracted with water or an organic solvent. The resulting extract, the main component of which is proanthocyanidins. Among them, a grape seed extract is preferable because it has a high content and a low content of impurities such as saccharides, so that high-purity proanthocyanidins can be easily obtained by extraction.
【００１０】ブドウ種子からの抽出物以外では、小豆か
らの抽出物（有賀ら、アグリカルチュラル・バイオロジ
カル・ケミストリー（Agric.Biol.Chem.）第45巻、2709
-2712頁、1981年）、松の樹皮からの抽出物（R.W.Hemin
gwayら、フィトケミストリー（Phytochemistry）第22
巻、275-281頁、1983年）などがある。Except for the extract from grape seeds, the extract from red beans (Ariga et al., Agric. Biol. Chem.) 45, 2709
-2712, 1981), extract from pine bark (RWHemin
gway et al., Phytochemistry No. 22
Vol., Pp. 275-281, 1983).
【００１１】以上のようにして得られたプロアントシア
ニジンを主体とする抽出物は、液状もしくは半固形状の
形態で得られるが、このものから抽出溶媒を減圧留去、
スプレードライ、凍結乾燥などの公知の方法によって除
去すれば、そのままプロアントシアニジン含有濃縮物や
乾燥物として使用することができる。特開平11-80148号
の実施例に示すように、最適の原料と抽出条件を用いれ
ば、90％以上の高い純度を有するプロアントシアニジン
組成物を、簡単に得ることができる。The proanthocyanidin-based extract obtained as described above is obtained in a liquid or semi-solid form, and the extraction solvent is distilled off therefrom under reduced pressure.
If removed by a known method such as spray drying or freeze drying, it can be used as it is as a proanthocyanidin-containing concentrate or dried product. As shown in the examples of JP-A-11-80148, a proanthocyanidin composition having a high purity of 90% or more can be easily obtained by using optimal raw materials and extraction conditions.
【００１２】次に渋味を低減するためにプロアントシア
ニジンに添加するタンパク質／多糖類であるが、本質的
には渋味が低減されればどのようなタンパク質／多糖類
であってもよく、その由来原料、産地、時期、製造方法
等に制限はない。ただし添加によって渋味が低減された
プロアントシアニジンは主として食品として用いられる
ことから、食用のタンパク質／多糖類もしくはタンパク
質／多糖類を含有する食品を使用することが好ましい。
また渋味低減の原理がプロアントシアニジンとタンパク
質／多糖類の疎水結合（又は水素結合）に基づくもので
あると考えられることから、両者の分子の接触が時間的
にも面積的にも効率的に行なわれるために、水溶性もし
くは水中に分散可能なタンパク質／多糖類が好ましい。
さらに渋味が低減されたプロアントシアニジン（すなわ
ちプロアントシアニジン−タンパク質／多糖類の結合
体）の食品としての用途の選択肢が広くなることから、
この渋味低減化品（結合体）自身も水に溶ける又は分散
可能であることが望ましい。またその優れた生理活性を
利用するためには、成人で1日当たり50-500mg程度のプ
ロアントシアニジン摂取が必要となるが、経済的な因子
も満たされなければ現実的にはこの量を摂取することは
不可能である。そういう意味でここで用いられるタンパ
ク質／多糖類もしくはタンパク質／多糖類を含有する食
品は安価で、一定の品質のものを大量に、しかも容易に
入手できることが望まれる。Next, the protein / polysaccharide to be added to proanthocyanidin to reduce the astringency is essentially any protein / polysaccharide as long as the astringency is reduced. There are no restrictions on the source material, place of production, timing, production method, and the like. However, since proanthocyanidins whose astringency has been reduced by addition are mainly used as foods, it is preferable to use edible proteins / polysaccharides or foods containing proteins / polysaccharides.
Also, since the principle of astringency reduction is thought to be based on the hydrophobic bond (or hydrogen bond) between proanthocyanidin and the protein / polysaccharide, the contact of both molecules is efficient in terms of time and area. To be performed, proteins / polysaccharides that are water soluble or dispersible in water are preferred.
Further, since the choice of proanthocyanidins with reduced astringency (that is, the proanthocyanidin-protein / polysaccharide conjugate) as foods is broadened,
It is desirable that the astringency-reduced product (combined body) itself be soluble or dispersible in water. In addition, to take advantage of its excellent physiological activity, adults need to take about 50-500 mg of proanthocyanidin per day, but if economic factors are not satisfied, it is practical to take this amount. Is impossible. In this sense, it is desired that the protein / polysaccharide or the food containing the protein / polysaccharide used here is inexpensive, that a large quantity of a certain quality can be easily obtained.
【００１３】このような観点からタンパク質は、牛乳由
来のタンパク質及び大豆由来のタンパク質が好適であ
る。例えば、市販の食品では牛乳、全脂粉乳、全脂練
乳、脱脂粉乳、カゼイン、牛乳ホエー、ラクトアルブビ
ン、豆乳、粉末状分離大豆タンパク等が挙げられる。こ
の他上記の条件を満たすタンパク質の例として、ゼラチ
ン、コラーゲン、卵白アルブミン、可溶性小麦タンパク
質等も挙げられるが、計量が簡単であること、安価であ
ることなどから脱脂粉乳と粉末状分離大豆タンパクが好
適である。From such a viewpoint, the protein is preferably a protein derived from milk and a protein derived from soybean. For example, commercially available foods include milk, whole-fat milk powder, whole-fat condensed milk, skim milk powder, casein, milk whey, lactalbubin, soy milk, powdered isolated soy protein, and the like. In addition, examples of proteins satisfying the above conditions include gelatin, collagen, ovalbumin, soluble wheat protein, and the like.However, skim milk powder and powdery separated soy protein are used because they are easy to measure and inexpensive. It is suitable.
【００１４】同様に多糖類としては、デンプン及び寒天
が好適であり、特にデンプンの場合はアルファー化した
ものが好ましい。市販の食品ではデンプンとして小麦
粉、コーンスターチ、バレイショデンプン（片栗粉）、
米粉等、寒天では粉末寒天、棒寒天、フレーク寒天、糸
寒天等が例として挙げられる。この他上記の条件を満た
す多糖類の例として、サイリウムなどの食物繊維、ペク
チン、デキストラン、コンドロイチン硫酸等も挙げられ
るが、渋味低減効果が大きいこと、安価であることなど
から米粉、粉寒天が好適である。Similarly, as the polysaccharide, starch and agar are preferable, and particularly, in the case of starch, pregelatinized one is preferable. In commercial foods, starches such as flour, corn starch, potato starch (starch),
Examples of agar such as rice flour include powder agar, stick agar, flake agar, and thread agar. In addition, examples of polysaccharides satisfying the above conditions include dietary fiber such as psyllium, pectin, dextran, chondroitin sulfate, and the like. It is suitable.
【００１５】添加するタンパク質／多糖類の量はそのタ
ンパク質／多糖類の種類や純度によって影響されるが、
プロアントシアニジンとタンパク質／多糖類のそれぞれ
が100%純度のものとしたとき、重量混合比はプロアント
シアニジン：タンパク質／多糖類＝1:1〜1:100であり、
好ましくは1:1〜1:10である。The amount of protein / polysaccharide to be added is affected by the type and purity of the protein / polysaccharide.
When each of proanthocyanidin and protein / polysaccharide is 100% pure, the weight mixing ratio is proanthocyanidin: protein / polysaccharide = 1: 1 to 1: 100,
Preferably it is 1: 1 to 1:10.
【００１６】タンパク質／多糖類のプロアントシアニジ
ンへの添加方法には制限がないが、通常1〜10%濃度のプ
ロアントシアニジン水溶液へ、必要量のタンパク質／多
糖類をよくかき混ぜながら添加するとよい。タンパク質
／多糖類が固体であればはそのまま加えても、粉状にし
てから添加しても良いし、適度な濃度で水に溶解又は分
散させてから加えても良い。添加時の温度はタンパク質
の場合は変性の恐れがあるため通常5〜50℃、好ましく
は15〜40℃である。多糖類の場合は通常5〜90℃、好ま
しくは15〜50℃である。また粉状のプロアントシアニジ
ンと粉状のタンパク質／多糖類を乳鉢や粉体混合機など
で混合することもできる。The method of adding the protein / polysaccharide to the proanthocyanidin is not limited, but it is usually preferable to add the required amount of the protein / polysaccharide to the aqueous proanthocyanidin solution at a concentration of 1 to 10% while thoroughly stirring. If the protein / polysaccharide is a solid, it may be added as it is, or may be added after being powdered, or may be added after being dissolved or dispersed in water at an appropriate concentration. The temperature at the time of addition is usually 5 to 50 ° C, preferably 15 to 40 ° C, because of the possibility of denaturation in the case of proteins. In the case of polysaccharides, the temperature is usually 5 to 90 ° C, preferably 15 to 50 ° C. Further, powdery proanthocyanidin and powdery protein / polysaccharide can be mixed in a mortar, a powder mixer or the like.
【００１７】渋味が低減化されたプロアントシアニジン
の食品としての形態には特に制限がないが、水や牛乳に
溶解又は分散させた液体の形、ゼリーなどのゲルの形、
粉体・顆粒状の形などが例として挙げられる。もちろん
従来通り、カプセルや錠剤の形を利用しても良い。There are no particular restrictions on the form of the proanthocyanidin with reduced astringency as a food, but the form of a liquid dissolved or dispersed in water or milk, the form of a gel such as jelly,
Examples include powdery and granular forms. As a matter of course, capsules and tablets may be used as usual.
【００１８】[0018]
【発明の効果】本発明によれば、プロアントシアニジン
の量的な損失を伴わず、安価で効率よく大量に、しかも
安全にプロアントシアニジンの渋味を低減することがで
きる。その結果、粉末タイプであっても渋味が軽度であ
り、錠剤やカプセル剤の形態での摂取が困難な小児や高
齢者であっても容易にプロアントシアニジンが摂取で
き、また渋味が低減化されたプロアントシアニジン組成
物を広く市場に提供することができる。According to the present invention, the astringency of proanthocyanidins can be reduced safely, inexpensively, in large quantities, and safely without loss of the quantity of proanthocyanidins. As a result, even if it is a powder type, the astringency is mild, and even children and elderly people who have difficulty in taking tablets or capsules can easily take proanthocyanidins and reduce astringency. The obtained proanthocyanidin composition can be widely marketed.
【００１９】なお、本発明において、渋味の尺度は以下
のようにして定めた。 ＜渋味の尺度の設定（渋味評価標準曲線の作製）＞渋味
の強さを表す単位、尺度あるいは標準品が存在しないた
め、種々の濃度でブドウ種子抽出物（キッコーマン(株)
製、「グラビノールスーパー」、プロアントシアニジン
純度95%、以下GVSと略す。）を水に溶解し、15人のパネ
ラーを使って、その水溶液の渋味を官能評価し、渋味評
価標準曲線を作製した。渋味評価点は次の様に定めた。 ｛0点；渋味を感じない、1点；わずかに渋い、2点；渋
い、3点；かなり渋い。｝ パネラーによる渋味評価平均点が1点になる濃度を「渋
味発現最低濃度」と定めた。In the present invention, the scale of astringency is determined as follows. <Setting of Astringency Scale (Preparation of Astringency Evaluation Standard Curve)> Since there is no unit, scale or standard representing astringency intensity, grape seed extract (Kikkoman Co., Ltd.) at various concentrations
Manufactured by "Grabinol Super", proanthocyanidin purity 95%, hereinafter abbreviated as GVS. ) Was dissolved in water, and the astringency of the aqueous solution was organoleptically evaluated using 15 panelists to prepare a standard curve for evaluating astringency. The astringency evaluation points were determined as follows. ｛0 points: no astringency, 1 point; slightly bitter, 2 points; bitter, 3 points;濃度 The concentration at which the average astringency evaluation score by the panelists is 1 point is defined as the "minimum concentration for expressing astringency".
【００２０】官能評価試験は25℃、室内、昼食後1〜3時
間後に実施。各濃度のサンプル5ｍLを、濃度の薄い方か
ら順番に口腔内に5-10秒間含んだ後、嚥下して官能評価
を行なった。各サンプルの官能評価終了後直ちに、水で
口腔うがいを実施し、2分間以上間隔を開けてから次の
サンプルの官能評価を実施した。GVS水溶液の渋味の官
能評価試験結果を表1及び図1に示す。The sensory evaluation test was carried out at 25 ° C. in a room, 1 to 3 hours after lunch. After 5 mL of a sample of each concentration was contained in the oral cavity for 5 to 10 seconds in order from the one with the lowest concentration, it was swallowed and the sensory evaluation was performed. Immediately after the end of the sensory evaluation of each sample, oral gargling was performed with water, and after an interval of 2 minutes or more, the sensory evaluation of the next sample was performed. The results of a sensory evaluation test of the astringency of the GVS aqueous solution are shown in Table 1 and FIG.
【００２１】[0021]
【表１】 図1の渋味評価標準曲線より、GVS水溶液の渋味発現最低
濃度は約0.06%と判る。[Table 1] From the astringency evaluation standard curve in FIG. 1, it can be seen that the minimum concentration for expressing astringency of the GVS aqueous solution is about 0.06%.
【００２２】[0022]
【実施例】以下に実施例を示して本発明をさらに具体的
に説明するが、本発明はこれらの例に限定されるもので
はない。 ＜実施例1＞牛乳を用いた渋味の低減効果 種々の濃度でGVSを牛乳に溶解し、13人のパネラーを使
って、渋味を官能評価した。牛乳は雪印乳業（株）製3.
5牛乳を使用した。GVS牛乳溶液の渋味評価試験の結果を
表2及び図2に示す。The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. <Example 1> Effect of reducing astringency using milk GVS was dissolved in milk at various concentrations, and the astringency was sensory evaluated using 13 panelists. Milk is manufactured by Snow Brand Milk Products Co., Ltd. 3.
Five milks were used. Table 2 and FIG. 2 show the results of the astringency evaluation test of the GVS milk solution.
【００２３】[0023]
【表２】 [Table 2]
【００２４】図2の渋味評価曲線より、GVS牛乳溶液の渋
味発現最低濃度は約1.7%と判る。これは水溶液の場合の
約30倍の濃度であり、牛乳に渋味低減効果があることが
明確に判る。また牛乳中のタンパク質は約7%であること
から、渋味発現最低濃度における重量比はおよそ、GV
S：牛乳タンパク質＝1：４である。From the astringency evaluation curve in FIG. 2, it can be seen that the minimum concentration of astringent taste expression of the GVS milk solution is about 1.7%. This is about 30 times the concentration of the aqueous solution, and clearly shows that milk has an astringency reducing effect. Also, since the protein in milk is about 7%, the weight ratio at the lowest concentration of astringent expression is approximately GV
S: milk protein = 1: 4.
【００２５】＜実施例2＞豆乳を用いた渋味の低減効果 実施例１と同様に、種々の濃度でGVSを市販の豆乳飲料
（名古屋製酪（株）「豆腐のできる豆乳」）に溶解し、
15人のパネラーを使って、渋味を官能評価した。GVS豆
乳溶液の渋味評価試験の結果を表3及び図3に示す。Example 2 Effect of Reducing Astringency Using Soy Milk As in Example 1, GVS was dissolved at various concentrations in a commercially available soy milk drink (Nagoya Dairy Co., Ltd. “Tofu-forming soy milk”). And
Sensory evaluation of astringency was conducted using 15 panelists. Table 3 and FIG. 3 show the results of the astringency evaluation test of the GVS soymilk solution.
【００２６】[0026]
【表３】 [Table 3]
【００２７】図3の渋味評価曲線より、GVS豆乳溶液の渋
味発現最低濃度は約3.9%と判る。これは水溶液の場合の
60〜70倍濃度であり、豆乳に渋味低減効果があることが
明確に判る。また豆乳中のタンパク質は約12%であるこ
とから、渋味発現最低濃度における重量比はおよそ、GV
S：豆乳タンパク質＝1：3である。From the astringency evaluation curve of FIG. 3, it can be seen that the minimum concentration of astringent expression of the GVS soymilk solution is about 3.9%. This is the case for aqueous solutions
It is 60-70 times the concentration, which clearly shows that soy milk has an astringency reducing effect. Since the protein in soy milk is about 12%, the weight ratio at the lowest concentration of astringent taste expression is approximately GV
S: soy milk protein = 1: 3.
【００２８】＜実施例3＞うるち米粉を用いた渋味の低
減効果 GVSを最終的に0.5％の濃度になるように水に溶解し、そ
こに種々の比率になるようにうるち米粉（上白粉）を添
加、よくかき混ぜて溶解後、15人のパネラーにより渋味
を官能評価した。うるち米粉は山形県食料（株）の上白
粉（アルファー化）を用いた。GVS−うるち米粉混合物
の渋味評価試験の結果を表5及び図4に示す。<Example 3> Reduction effect of astringency using glutinous rice flour GVS is dissolved in water so as to have a final concentration of 0.5%, and glutinous rice flour (Kami-Shirami) in various ratios there. ) Was added, mixed well and dissolved, and then the sensory evaluation of astringency was carried out by 15 panelists. Uruchi rice flour used was Yamagata Prefectural Foods Co., Ltd. Kamigaku flour (pre-alpha). Table 5 and FIG. 4 show the results of the astringency evaluation test of the GVS-glutinous rice flour mixture.
【００２９】[0029]
【表４】 [Table 4]
【００３０】図4の渋味評価曲線より、GVS／うるち米粉
の渋味発現最低混合比は約0.11と判る。またうるち米粉
中のデンプンは約80%であることから、渋味発現最低混
合比における重量比はおよそ、GVS：うるち米粉デンプ
ン＝1：7である。From the astringency evaluation curve of FIG. 4, it can be seen that the minimum mixing ratio of GVS / glutinous rice flour to express astringency is about 0.11. Also, since the starch in the glutinous rice flour is about 80%, the weight ratio in the minimum mixture ratio for expressing astringency is approximately GVS: glutinous rice flour starch = 1: 7.
【００３１】＜実施例4＞粉末寒天を用いた渋味の低減
方法 うるち米粉の代わりに粉末寒天を用いること以外、実施
例3と同様の操作を行ない、15人のパネラーによる渋味
の官能評価を実施した。粉末寒天は伊那食品（株）製ウ
ルトラ寒天ＡX−３０を使用した。GVS−粉末寒天混合物
の渋味評価試験の結果を表6及び図5に示す。Example 4 Method for Reducing Astringency Using Powder Agar The same operation as in Example 3 was performed, except that powder agar was used instead of glutinous rice flour, and sensory evaluation of astringency was performed by 15 panelists. Was carried out. The powder agar used was Ultra Agar AX-30 manufactured by Ina Foods Co., Ltd. The results of the astringency evaluation test of the GVS-powder agar mixture are shown in Table 6 and FIG.
【００３２】[0032]
【表５】 [Table 5]
【００３３】図5の渋味評価曲線より、GVS／粉末寒天の
渋味発現最低混合比は約0.30と判る。また粉末寒天中の
寒天含有量が約70%であることから、渋味発現最低混合
比における重量比はおよそ、GVS：寒天＝1：2である。From the astringency evaluation curve in FIG. 5, it can be seen that the minimum mixing ratio of GVS / powder agar for expressing astringency is about 0.30. In addition, since the agar content in the powder agar is about 70%, the weight ratio in the minimum mixture ratio for expressing astringency is approximately GVS: agar = 1: 2.
【００３４】＜実施例5＞脱脂粉乳を用いた渋味の低減
効果 うるち米粉の代わりに脱脂粉乳を用いること以外、実施
例3と同様の操作を行ない、15人のパネラーによる渋味
の官能評価試験を実施した。脱脂粉乳は雪印乳業（株）
製スキムミルクを使用した。GVS−脱脂粉乳混合物の渋
味評価試験の結果を表7及び図6に示す。<Example 5> Effect of reducing astringency using skim milk powder The same operation as in Example 3 was performed except that skim milk powder was used instead of glutinous rice powder, and sensory evaluation of astringency was performed by 15 panelists. The test was performed. Skim milk powder is Snow Brand Milk Products Co., Ltd.
Skim milk made by the company was used. The results of the astringency evaluation test of the GVS-skim milk powder mixture are shown in Table 7 and FIG.
【００３５】[0035]
【表６】 [Table 6]
【００３６】図6の渋味評価曲線より、GVS／脱脂粉乳の
渋味発現最低混合比は約0.32と判る。また脱脂粉乳中の
タンパク質は約40%であることから、渋味発現最低混合
比における重量比はおよそ、GVS：脱脂粉乳タンパク質
＝3：８である。From the astringency evaluation curve in FIG. 6, it can be seen that the minimum mixing ratio of GVS / skim milk powder to express astringency is about 0.32. Also, since the protein in skim milk powder is about 40%, the weight ratio in the minimum astringency expression mixture ratio is approximately GVS: skim milk protein = 3: 8.
【００３７】＜実施例6＞大豆プロテインを用いた渋味
の低減効果 うるち米粉の代わりに大豆プロテインを用いること以
外、実施例3と同様の操作を行ない、15人のパネラーに
よる渋味の官能評価試験を実施した。大豆プロテインは
不二製油（株）製スプロ670を使用した。GVS−大豆プロ
テイン混合物の渋味評価試験の結果を表8及び図7に示
す。Example 6 Effect of Reducing Astringency Using Soy Protein The same operation as in Example 3 was carried out except that soy protein was used instead of glutinous rice flour, and sensory evaluation of astringency was performed by 15 panelists. The test was performed. The soybean protein used was Supro 670 manufactured by Fuji Oil Co., Ltd. The results of the astringency evaluation test of the GVS-soy protein mixture are shown in Table 8 and FIG.
【００３８】[0038]
【表７】 [Table 7]
【００３９】図7の渋味評価曲線より、GVS／大豆プロテ
インの渋味発現最低混合比は約0.42と判る。また大豆プ
ロテイン中のタンパク質は約80%であることから、渋味
発現最低混合比における重量比はおよそ、GVS：脱脂粉
乳タンパク質＝1：2である。From the astringency evaluation curve in FIG. 7, it can be seen that the minimum mixing ratio of GVS / soy protein to express astringency is about 0.42. In addition, since the protein in soy protein is about 80%, the weight ratio in the minimum mixing ratio for expressing astringency is approximately GVS: skim milk protein = 1: 2.
【００４０】＜実施例８＞寒天−渋味低減化プロアント
シアニジン組成物の製造 GVS：24ｇと伊那寒天（株）製ウルトラ寒天AX-30：96ｇ
をよく混合し蒸留水0.6Lを加え、よく撹拌して完全に溶
解させた。これを凍結乾燥し、粉状のプロアントシアニ
ジン組成物を120ｇ得た。この組成物の渋味のパネラー1
5人による官能評価点は、0.533であり、ほとんど渋味は
感じられない。またこの組成物10ｇは室温下で、水50ｍ
Lに瞬時に分散できた。<Example 8> Production of agar-astringency-reduced proanthocyanidin composition GVS: 24 g and Ultra agar AX-30 manufactured by Ina agar Co., Ltd .: 96 g
Was thoroughly mixed, 0.6 L of distilled water was added, and the mixture was thoroughly stirred to completely dissolve. This was freeze-dried to obtain 120 g of a powdery proanthocyanidin composition. Astringent paneler 1 of this composition
The sensory evaluation score by five persons was 0.533, and almost no astringency was felt. Also, 10 g of this composition is 50 m water at room temperature.
L was instantly dispersed.
【００４１】＜実施例9＞大豆プロテイン−渋味低減化
プロアントシアニジン組成物の製造 GVS：24ｇと不二製油（株）製スプロ670：96ｇをよく混
合し蒸留水0.6Lを加え、よく撹拌して完全に溶解させ
た。これを凍結乾燥し、粉状のプロアントシアニジン組
成物を120ｇ得た。この組成物の渋味のパネラー15人に
よる官能評価点は、0.333であり、ほとんど渋味は感じ
られない。またこの組成物10ｇは室温下で、水50ｍLに
瞬時に分散できた。<Example 9> Production of soybean protein-astringent taste-reduced proanthocyanidin composition GVS: 24 g and Fuji Oil Co., Ltd.'s Supro 670: 96 g were mixed well, 0.6 L of distilled water was added, and the mixture was stirred well. And completely dissolved. This was freeze-dried to obtain 120 g of a powdery proanthocyanidin composition. The sensory evaluation score of 15 a panelists of astringency of this composition was 0.333, and almost no astringency was felt. Also, 10 g of this composition could be instantaneously dispersed in 50 mL of water at room temperature.
【００４２】＜実施例10＞顆粒状食品 １包が下記の処方になるように、水及びエタノールを用
いて湿式造粒した後アルミニウムヒートシール包装を実
施し、顆粒状食品2.6gを分包（１包当たりGVSとして400
mg含有）した。 Example 10 Granulated food was wet-granulated using water and ethanol so that one package had the following formulation, and then aluminum heat-sealed and packaged, and 2.6 g of granular food was packaged ( 400 GVS per packet
mg).
【００４３】＜実施例11＞粉末状食品 １包が下記の処方になるように、各成分をよく混合した
後、アルミニウムヒートシール包装を実施し、粉末状食
品2.5gを分包（１包当たりGVSとして400mg含有）した。 <Example 11> After the ingredients were mixed well so that one package of powdered food had the following formulation, aluminum heat seal packaging was carried out, and 2.5 g of powdered food was packaged (per packet). (Containing 400 mg as GVS).
【００４４】＜実施例12＞錠剤状食品 1錠が下記の処方になるように、各成分をよく混合した
後打錠機により圧縮成型し、錠剤状食品250mgを製造し
た（1錠当たりGVSとして40mg含有）した。 Example 12 Tablet Foods 250 mg of tablet food was produced by mixing each component well and compressing it with a tableting machine so that one tablet had the following formulation, and produced a tablet food (GVS per tablet). 40 mg).
【００４５】＜実施例13＞ドリンク剤 下記の処方のドリンク剤を製造した。1本当たりGVSとし
て400mg含有。 Example 13 Drink Preparation A drink preparation having the following formulation was produced. Contains 400mg as GVS per bottle.
【００４６】[0046]
【図１】渋味評価標準曲線図FIG. 1 is a standard curve diagram for evaluating astringency
【図２】牛乳の渋味低減効果を示す図FIG. 2 is a diagram showing the effect of reducing the astringency of milk.
【図３】豆乳の渋味低減効果を示す図FIG. 3 is a graph showing the effect of reducing the astringency of soy milk.
【図４】うるち米粉の渋味低減効果を示す図FIG. 4 is a diagram showing the effect of reducing the astringency of glutinous rice flour.
【図５】粉末寒天の渋味低減効果を示す図FIG. 5 is a diagram showing the effect of reducing the astringency of powder agar.
【図６】脱脂粉乳の渋味低減効果を示す図FIG. 6 is a diagram showing the astringency reducing effect of skim milk powder
【図７】大豆プロテインの渋味低減効果を示す図FIG. 7 is a graph showing the astringency reducing effect of soy protein.
─────────────────────────────────────────────────────
────────────────────────────────────────────────── ───
【手続補正書】[Procedure amendment]
【提出日】平成１１年８月２７日（１９９９．８．２
７）[Submission date] August 27, 1999 (1999.8.2
7)
【手続補正１】[Procedure amendment 1]
【補正対象書類名】明細書[Document name to be amended] Statement
【補正対象項目名】０００３[Correction target item name] 0003
【補正方法】変更[Correction method] Change
【補正内容】[Correction contents]
【０００３】[0003]
【化１】 （式中Ｒ1は水素原子又は水酸基、Ｒ2、Ｒ6はそれぞれ
独立に水素原子、水酸基又はメトキシ基、Ｒ4、Ｒ3、Ｒ
7、Ｒ8はそれぞれ独立に水酸基又はメトキシ基、Ｒ5は
ガロイル基又はグルコピラノシル基を示す）で表され
る、フラバン-3-オールまたはフラバン-3,4-ジオールを
構成単位として、4-6位又は4-8位で縮合もしくは重合に
より結合した化合物群であり、各種植物体中に存在する
縮合型タンニンである。なお化１は、理解を助けるため
に4-8位で縮合した場合だけを示している。これらは酸
処理によりシアニジン、デルフィニジン、ペラルゴニジ
ン等のアントシアニジンを生成するところから、この名
称が与えられているものである。そして上記構成単位の
２量体、３量体、４量体さらに１０〜３０量体以上の高
分子のプロシアニジン、プロデルフィニジン、プロペラ
ルゴニジン等のプロアントシアニジンおよびそれらの立
体異性体等を含むものである。Embedded image (Wherein R 1 is a hydrogen atom or a hydroxyl group, R 2 and R 6 are each independently a hydrogen atom, a hydroxyl group or a methoxy group, R 4 , R 3 , R
7 and R 8 each independently represent a hydroxyl group or a methoxy group, and R 5 represents a galloyl group or a glucopyranosyl group), represented by flavan-3-ol or flavan-3,4-diol as a constituent unit. A group of compounds linked by condensation or polymerization at the 4th or 4th to 8th positions, and are condensed tannins present in various plants. In addition, chemical formula 1 shows only the case where condensation is performed at the 4-8 position to facilitate understanding. These are given the name because they produce anthocyanidins such as cyanidin, delphinidin and pelargonidin by acid treatment. The dimer, the trimer, the tetramer, and the 10 to 30-mer or more of the above structural units include proanthocyanidins such as procyanidin, prodelphinidin, and properargonidine, and stereoisomers thereof.
Claims (5)
アニジンを主成分とする抽出物にタンパク質及び／又は
多糖類を添加することを特徴とするプロアントシアニジ
ンの渋味低減方法。1. A method for reducing the astringency of proanthocyanidins, comprising adding a protein and / or a polysaccharide to an extract containing proanthocyanidins as a main component obtained by extracting a plant.
ウの種子、ブドウの皮又はブドウの搾汁粕のいずれかの
抽出物から選ばれた１種である請求項１記載のプロアン
トシアニジンの渋味低減方法。2. The proanthocyanidin according to claim 1, wherein the plant extract is one selected from extracts of fermented grape food, grape seed, grape skin and grape juice cake. Astringency reduction method.
豆蛋白である請求項１記載のプロアントシアニジンの渋
味低減方法。3. The method for reducing astringency of proanthocyanidins according to claim 1, wherein the protein is skim milk powder and / or isolated soy protein.
項１記載のプロアントシアニジンの渋味低減方法。4. The method for reducing astringency of proanthocyanidins according to claim 1, wherein the polysaccharide is starch and / or agar.
アニジンを主成分とする抽出物にタンパク質及び／又は
多糖類を添加した、渋味の低減されたプロアントシアニ
ジン組成物。5. A proanthocyanidin composition having reduced astringency, wherein a protein and / or polysaccharide is added to an extract containing proanthocyanidin as a main component obtained by extracting a plant.
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|---|---|---|---|
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|---|---|---|---|
| JP22818299A JP3616286B2 (en) | 1999-08-12 | 1999-08-12 | Astringency reduction method of proanthocyanidins |
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ID=16872505
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002085135A1 (en) * | 2001-04-20 | 2002-10-31 | Toshiyuki Sakiura | Carotenoid-contaiing fish feeds having polyphenol added thereto |
| WO2005122794A1 (en) * | 2004-06-17 | 2005-12-29 | Toyo Shinyaku Co., Ltd. | Composition containing plant extract and material derived from milk |
| JP2007054019A (en) * | 2005-08-26 | 2007-03-08 | Otsuka Pharmaceut Co Ltd | Pine bark extract-containing beverage |
| JP2007082482A (en) * | 2005-09-22 | 2007-04-05 | Kikkoman Corp | Proanthocyanidin-containing food, and method for producing the same |
| JPWO2005087758A1 (en) * | 2004-03-15 | 2008-01-24 | 株式会社東洋新薬 | Proanthocyanidin water-soluble conjugate and composition containing the same |
| JP2009065899A (en) * | 2007-09-13 | 2009-04-02 | Shimane Pref Gov | Method for removing astringency from astringent component-containing fruit food, and production method for the astringent component-containing fruit food |
| EP2058297A1 (en) | 2007-11-08 | 2009-05-13 | Symrise GmbH & Co. KG | Use of alkamides for masking an unpleasant flavor |
| JP2011024600A (en) * | 2010-11-10 | 2011-02-10 | Shimane Prefecture | Method for removing astringency from fruit containing astringent component and method for producing food thereby |
| JP2013021948A (en) * | 2011-07-19 | 2013-02-04 | Ina Food Industry Co Ltd | Polyphenol agar conjugate |
| EP2597082A1 (en) | 2011-11-24 | 2013-05-29 | Symrise AG | Compounds for masking an unpleasant taste |
| KR101555751B1 (en) | 2013-11-12 | 2015-09-30 | 대구한의대학교산학협력단 | Food composition having extract of unripe astringent persimmon for removed astringent taste |
| JP2017099320A (en) * | 2015-11-30 | 2017-06-08 | サントリー食品インターナショナル株式会社 | Tea beverage comprising grape seed polyphenol |
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1999
- 1999-08-12 JP JP22818299A patent/JP3616286B2/en not_active Expired - Fee Related
Cited By (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002085135A1 (en) * | 2001-04-20 | 2002-10-31 | Toshiyuki Sakiura | Carotenoid-contaiing fish feeds having polyphenol added thereto |
| JPWO2005087758A1 (en) * | 2004-03-15 | 2008-01-24 | 株式会社東洋新薬 | Proanthocyanidin water-soluble conjugate and composition containing the same |
| JP4648309B2 (en) * | 2004-03-15 | 2011-03-09 | 株式会社東洋新薬 | Proanthocyanidin water-soluble conjugate and composition containing the same |
| WO2005122794A1 (en) * | 2004-06-17 | 2005-12-29 | Toyo Shinyaku Co., Ltd. | Composition containing plant extract and material derived from milk |
| JP2007054019A (en) * | 2005-08-26 | 2007-03-08 | Otsuka Pharmaceut Co Ltd | Pine bark extract-containing beverage |
| JP4510726B2 (en) * | 2005-08-26 | 2010-07-28 | 大塚製薬株式会社 | Beverage containing pine bark extract |
| JP4589212B2 (en) * | 2005-09-22 | 2010-12-01 | キッコーマン株式会社 | Proanthocyanidin-containing food and process for producing the same |
| JP2007082482A (en) * | 2005-09-22 | 2007-04-05 | Kikkoman Corp | Proanthocyanidin-containing food, and method for producing the same |
| JP2009065899A (en) * | 2007-09-13 | 2009-04-02 | Shimane Pref Gov | Method for removing astringency from astringent component-containing fruit food, and production method for the astringent component-containing fruit food |
| JP4714888B2 (en) * | 2007-09-13 | 2011-06-29 | 島根県 | Astringency and production method of fruit foods containing astringency ingredients |
| EP2058297A1 (en) | 2007-11-08 | 2009-05-13 | Symrise GmbH & Co. KG | Use of alkamides for masking an unpleasant flavor |
| US8828469B2 (en) | 2007-11-08 | 2014-09-09 | Symrise Ag | Use of alkamides for masking an unpleasant flavor |
| JP2011024600A (en) * | 2010-11-10 | 2011-02-10 | Shimane Prefecture | Method for removing astringency from fruit containing astringent component and method for producing food thereby |
| JP2013021948A (en) * | 2011-07-19 | 2013-02-04 | Ina Food Industry Co Ltd | Polyphenol agar conjugate |
| EP2597082A1 (en) | 2011-11-24 | 2013-05-29 | Symrise AG | Compounds for masking an unpleasant taste |
| KR101555751B1 (en) | 2013-11-12 | 2015-09-30 | 대구한의대학교산학협력단 | Food composition having extract of unripe astringent persimmon for removed astringent taste |
| JP2017099320A (en) * | 2015-11-30 | 2017-06-08 | サントリー食品インターナショナル株式会社 | Tea beverage comprising grape seed polyphenol |
| JP2020000202A (en) * | 2018-07-02 | 2020-01-09 | 伊那食品工業株式会社 | Molded food product and method for producing the same |
| JP7168971B2 (en) | 2018-07-02 | 2022-11-10 | 伊那食品工業株式会社 | Shaped food and its manufacturing method |
| JP2021087401A (en) * | 2019-12-05 | 2021-06-10 | 中野Ｂｃ株式会社 | Food product and method for producing the same, and agent |
| JP7161210B2 (en) | 2019-12-05 | 2022-10-26 | 中野Ｂｃ株式会社 | Food and its manufacturing method and agent |
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