JP2003128664A - Polyphenol salt, food product and beverage, and method for reducing acerbity, bitterness or astringency of polyphenol or extract containing polyphenol - Google Patents
Polyphenol salt, food product and beverage, and method for reducing acerbity, bitterness or astringency of polyphenol or extract containing polyphenolInfo
- Publication number
- JP2003128664A JP2003128664A JP2001328146A JP2001328146A JP2003128664A JP 2003128664 A JP2003128664 A JP 2003128664A JP 2001328146 A JP2001328146 A JP 2001328146A JP 2001328146 A JP2001328146 A JP 2001328146A JP 2003128664 A JP2003128664 A JP 2003128664A
- Authority
- JP
- Japan
- Prior art keywords
- polyphenol
- salt
- astringency
- hydroxide
- extract
- 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
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 133
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 68
- -1 Polyphenol salt Chemical class 0.000 title claims abstract description 61
- 235000019606 astringent taste Nutrition 0.000 title claims abstract description 52
- 235000013305 food Nutrition 0.000 title claims abstract description 51
- 239000000284 extract Substances 0.000 title claims abstract description 32
- 235000013361 beverage Nutrition 0.000 title claims abstract description 23
- 235000019658 bitter taste Nutrition 0.000 title claims abstract description 18
- 235000002639 sodium chloride Nutrition 0.000 title abstract description 51
- 238000000034 method Methods 0.000 title abstract description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 57
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000003513 alkali Substances 0.000 claims abstract description 22
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000000920 calcium hydroxide Substances 0.000 claims abstract description 10
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims abstract description 10
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims abstract description 10
- 239000000347 magnesium hydroxide Substances 0.000 claims abstract description 10
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims abstract description 10
- 159000000007 calcium salts Chemical class 0.000 claims abstract description 6
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 6
- 159000000003 magnesium salts Chemical class 0.000 claims abstract description 5
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- 239000005018 casein Chemical group 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical group NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 235000004132 ellagic acid Nutrition 0.000 description 1
- 229960002852 ellagic acid Drugs 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 1
- 235000012734 epicatechin Nutrition 0.000 description 1
- 150000002170 ethers Chemical class 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
- 235000004515 gallic acid Nutrition 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 239000008273 gelatin Chemical group 0.000 description 1
- 229920000159 gelatin Chemical group 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 235000020333 oolong tea Nutrition 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 239000001814 pectin Chemical group 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- OHHNJQXIOPOJSC-UHFFFAOYSA-N stevioside Natural products CC1(CCCC2(C)C3(C)CCC4(CC3(CCC12C)CC4=C)OC5OC(CO)C(O)C(O)C5OC6OC(CO)C(O)C(O)C6O)C(=O)OC7OC(CO)C(O)C(O)C7O OHHNJQXIOPOJSC-UHFFFAOYSA-N 0.000 description 1
- 229940013618 stevioside Drugs 0.000 description 1
- 235000019202 steviosides Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Chemical group 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical group [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Tea And Coffee (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- General Preparation And Processing Of Foods (AREA)
- Non-Alcoholic Beverages (AREA)
- Pyrane Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、ポリフェノール塩、食
品、飲料およびポリフェノールまたはポリフェノール含
有抽出物の渋味、苦味または収斂味の軽減方法に関す
る。TECHNICAL FIELD The present invention relates to a method for reducing astringency, bitterness or astringency of polyphenol salts, foods, beverages and polyphenols or polyphenol-containing extracts.
【0002】[0002]
【従来の技術】カテキンに代表されるポリフェノール
は、茶、カカオなどの様々な植物に含まれ、各地に広く
分布する天然化合物であり、抗菌活性、抗酸化活性、抗
う食活性、抗ウィルス活性、抗アレルギー活性、α−ア
ミラーゼ阻害活性、血圧上昇抑制作用、血中コレステロ
ール低下作用などの様々な生理活性を有することから、
健康食品などへの適用が注目されている。しかしなが
ら、ポリフェノールは渋味、苦味または収斂味(以下、
「渋味等」という。)を有する化合物であり、これが多
量に含まれた食品を摂取すると、著しい渋味等を感じる
という問題があった。このような渋味等を軽減するに
は、ポリフェノールの持つ前記生理活性を犠牲にして、
ポリフェノールの摂取量または食品へのポリフェノール
の添加量を減らさなければならなかった。2. Description of the Related Art Polyphenols typified by catechin are natural compounds widely contained in various plants such as tea and cacao, and have antibacterial activity, antioxidant activity, anticaries activity, antiviral activity, Since it has various physiological activities such as antiallergic activity, α-amylase inhibitory activity, blood pressure elevation inhibitory activity, blood cholesterol lowering activity,
Its application to health foods is drawing attention. However, polyphenols have astringency, bitterness or astringency (hereinafter,
It is called "astringency". There is a problem in that when a food containing a large amount of this is ingested, a noticeable astringency is felt. To reduce such astringency, sacrifice the physiological activity of polyphenols,
The intake of polyphenols or the addition of polyphenols to foods had to be reduced.
【0003】[0003]
【発明が解決しようとする課題】本発明の主たる目的
は、渋味等が軽減され、しかも高い生理活性効果が得ら
れるポリフェノール塩、食品および飲料を提供すること
である。本発明の他の目的は、ポリフェノールおよびポ
リフェノール含有抽出物の渋味等の軽減方法を提供する
ことである。SUMMARY OF THE INVENTION The main object of the present invention is to provide a polyphenol salt, a food and a beverage, in which astringency and the like are reduced and a high physiologically active effect is obtained. Another object of the present invention is to provide a method for reducing the astringency of polyphenols and polyphenol-containing extracts.
【0004】[0004]
【課題を解決するための手段】本発明者らは、上記課題
を解決するために鋭意研究を行った結果、ポリフェノー
ルを特定のポリフェノール塩とすることによって、ポリ
フェノールの渋味等が軽減され、しかも、このポリフェ
ノール塩は、胃内と同等の酸性環境下では元のポリフェ
ノールに戻って本来の生理活性を発揮するという新たな
事実を見出し、本発明を完成させるに至った。Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems, the present inventors reduced the astringency and the like of polyphenol by using polyphenol as a specific polyphenol salt, and The present inventors have found the new fact that this polyphenol salt returns to the original polyphenol and exerts its original physiological activity in an acidic environment equivalent to that in the stomach, and has completed the present invention.
【0005】すなわち、本発明のポリフェノール塩は、
ポリフェノールのナトリウム塩、カルシウム塩、マグネ
シウム塩またはカリウム塩であることを特徴とする。こ
のポリフェノール塩は、渋味等が軽減されているので、
多量摂取が可能であり、しかも胃内では元のポリフェノ
ールに戻るので、多量摂取による高い生理活性効果が期
待される。また、ポリフェノール塩は、ポリフェノール
と比較して、水溶性が向上するので、水溶液とした場合
に濁りや沈殿物が生じにくい。このポリフェノール塩は
食品添加物、食品素材として好適に使用される。That is, the polyphenol salt of the present invention is
It is characterized in that it is a sodium salt, calcium salt, magnesium salt or potassium salt of polyphenol. This polyphenol salt has reduced astringency and the like,
A large amount can be ingested, and since it returns to the original polyphenol in the stomach, a high physiologically active effect due to the large amount is expected. Further, since the polyphenol salt has improved water solubility as compared with polyphenol, turbidity and precipitates are less likely to occur when it is used as an aqueous solution. This polyphenol salt is preferably used as a food additive or a food material.
【0006】本発明の食品は、前記ポリフェノール塩を
含有することを特徴とする。本発明では、ポリフェノー
ルそれ自体を中和する以外に、ポリフェノール含有植物
の抽出物を中和し、これを食品に含有させてもよい。The food of the present invention is characterized by containing the above polyphenol salt. In the present invention, in addition to neutralizing the polyphenol itself, the polyphenol-containing plant extract may be neutralized and added to the food.
【0007】すなわち、本発明の他の食品は、水酸化ナ
トリウム、水酸化カルシウム、水酸化マグネシウムおよ
び水酸化カリウムよりなる群から選ばれるアルカリで中
和したポリフェノール含有植物の抽出物を含有すること
を特徴とする。That is, another food of the present invention contains an extract of a polyphenol-containing plant neutralized with an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide. Characterize.
【0008】本発明における食品には、固形食品、クリ
ーム状ないしジャム状の半流動食品、ゲル状食品、飲料
などの他、これらに添加する食品添加物、食品素材など
も含むものである。上記食品の具体例としては、飲料、
焼き菓子、ガム、キャンディー、チョコレート、グミ、
ゼリー、乳製品、即席麺、アイスクリーム、氷菓、パン
などが挙げられる。The food products in the present invention include solid food products, cream-like or jam-like semi-liquid food products, gel food products, beverages and the like, as well as food additives and food materials added thereto. Specific examples of the above foods include beverages,
Baked goods, gum, candy, chocolate, gummy,
Examples include jelly, dairy products, instant noodles, ice cream, frozen desserts, and bread.
【0009】さらに、本発明では、ポリフェノール含有
茶葉の抽出液である飲料自体を中和してもよい。すなわ
ち、本発明の飲料は、ポリフェノール含有茶葉の抽出液
を水酸化ナトリウム、水酸化カルシウム、水酸化マグネ
シウムおよび水酸化カリウムよりなる群から選ばれるア
ルカリで中和して得られることを特徴とする。Further, in the present invention, the beverage itself, which is an extract of polyphenol-containing tea leaves, may be neutralized. That is, the beverage of the present invention is characterized by being obtained by neutralizing an extract of tea leaves containing polyphenol with an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide.
【0010】本発明にかかるポリフェノールの渋味、苦
味または収斂味の軽減方法は、ポリフェノールを水酸化
ナトリウム、水酸化カルシウム、水酸化マグネシウムお
よび水酸化カリウムよりなる群から選ばれるアルカリを
用いてポリフェノール塩とすることを特徴とする。The method for reducing the astringency, bitterness or astringency of polyphenols according to the present invention is a polyphenol salt obtained by using polyphenol as an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide. It is characterized by
【0011】本発明にかかるポリフェノール含有抽出物
の渋味、苦味または収斂味の軽減方法は、ポリフェノー
ル含有植物の抽出物を水酸化ナトリウム、水酸化カルシ
ウム、水酸化マグネシウムおよび水酸化カリウムよりな
る群から選ばれるアルカリで中和することを特徴とす
る。The method for reducing the astringency, bitterness or astringency of a polyphenol-containing extract according to the present invention is a method in which the polyphenol-containing plant extract is selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide. It is characterized by being neutralized with a selected alkali.
【0012】なお、本発明おいて、「中和する」とは、
pH6.5〜7.0、好ましくは6.8〜7.0の範囲
に調整することをいう。In the present invention, "neutralize" means
It means adjusting the pH to a range of 6.5 to 7.0, preferably 6.8 to 7.0.
【0013】[0013]
【発明の実施の形態】以下、本発明の一実施形態につい
て詳細に説明する。BEST MODE FOR CARRYING OUT THE INVENTION An embodiment of the present invention will be described in detail below.
【0014】1.ポリフェノール塩
本発明のポリフェノール塩は、ポリフェノールのナトリ
ウム塩、カルシウム塩、マグネシウム塩またはカリウム
塩である。1. Polyphenol Salt The polyphenol salt of the present invention is a sodium salt, calcium salt, magnesium salt or potassium salt of polyphenol.
【0015】ポリフェノールとは、同一ベンゼン環上に
2個以上のフェノール性水酸基を持つ化合物のことであ
る。本発明において使用されるポリフェノールとして
は、食用として許容されるものが挙げられ、例えばエピ
カテキン、エピカテキンガレート、エピガロカテキン、
エピガロカテキンガレート、カテキン、ガロカテキン、
カテキンガレート、ガロカテキンガレート、ロイコアン
トシアニン、没食子酸、没食子酸塩、エラグ酸等が挙げ
られ、いずれも渋味等を有する。これらポリフェノール
は、合成されたものであってもよいが、後述する植物か
ら抽出単離されたものであってもよい。The polyphenol is a compound having two or more phenolic hydroxyl groups on the same benzene ring. Examples of the polyphenol used in the present invention include those that are edible and include, for example, epicatechin, epicatechin gallate, epigallocatechin,
Epigallocatechin gallate, catechin, gallocatechin,
Examples include catechin gallate, gallocatechin gallate, leucoanthocyanin, gallic acid, gallate, ellagic acid, etc., all of which have astringency. These polyphenols may be synthetic ones or may be ones extracted and isolated from the plants described later.
【0016】前記ポリフェノール塩は、ポリフェノール
の有するフェノール性水酸基の水素原子がナトリウム、
カルシウム、マグネシウムまたはカリウムに置換された
ものである。このポリフェノール塩は、ポリフェノール
水溶液に水酸化ナトリウム、水酸化カルシウム、水酸化
マグネシウムまたは水酸化カリウムを添加しpHを約
6.5〜7.0、好ましくは約6.8〜7.0に調整す
ることにより得られる。In the polyphenol salt, the hydrogen atom of the phenolic hydroxyl group of the polyphenol is sodium,
It has been replaced with calcium, magnesium or potassium. The pH of this polyphenol salt is adjusted to about 6.5 to 7.0, preferably about 6.8 to 7.0 by adding sodium hydroxide, calcium hydroxide, magnesium hydroxide or potassium hydroxide to an aqueous polyphenol solution. It is obtained by
【0017】上記水酸化ナトリウムなどのアルカリは、
前記ポリフェノール水溶液に対して固体の形態で添加し
てもよいが、好ましくは水溶液の形態で添加するのがよ
い。アルカリとしては、ポリフェノールが中和反応によ
りポリフェノール塩となることが必要であるため、上記
した水酸化物が好適である。なお、食品添加物である重
曹やかん水なども、上記アルカリに代えて使用すること
ができる。The alkali such as sodium hydroxide is
The polyphenol aqueous solution may be added in the form of a solid, but it is preferably added in the form of an aqueous solution. As the alkali, the above-mentioned hydroxide is preferable because it is necessary that the polyphenol is converted into the polyphenol salt by the neutralization reaction. It should be noted that food additives such as baking soda and brackish water may be used instead of the above alkali.
【0018】必要に応じて、得られたポリフェノール塩
水溶液を乾燥させて粉末などに加工することもできる。
粉末にする際には、必要に応じてデキストリンなどの添
加物を配合してもよい。乾燥させる手段は、特に限定さ
れず、例えば流動層乾燥器などを使用することができ
る。このようにして渋味等が軽減されたポリフェノール
塩は、該塩のまま摂取することもできるが、後述するよ
うに、食品に添加して摂取することもできる。If necessary, the obtained polyphenol salt aqueous solution may be dried and processed into powder or the like.
When powdered, additives such as dextrin may be added as necessary. The means for drying is not particularly limited, and for example, a fluidized bed dryer or the like can be used. The polyphenol salt in which the astringency and the like are reduced in this manner can be ingested as it is, but can also be ingested by adding it to foods, as described later.
【0019】2.抽出物
前記したように、ポリフェノールは植物から抽出単離さ
れたものであってもよい。このようなポリフェノール含
有植物としては、例えば茶葉、豆類、果実、根菜類、き
のこ類などが挙げられ、具体的には、例えば緑茶葉、ウ
ーロン茶葉、紅茶葉、カカオ豆、リンゴの果実、柿の果
実、ジャガイモなどが挙げられる。上記以外でポリフェ
ノールが含まれている植物としてはユーカリ属植物など
が挙げられる。ユーカリ属の植物のうち、抽出に供する
部分は、特に制限されないが、葉、実、蕾、幹、根等が
挙げられ、特に葉が好ましい。2. Extract As described above, the polyphenol may be extracted and isolated from the plant. Examples of such polyphenol-containing plants include tea leaves, beans, fruits, root vegetables, mushrooms, and the like, and specifically, for example, green tea leaves, oolong tea leaves, black tea leaves, cacao beans, apple fruits, persimmon leaves. Examples include fruits and potatoes. Examples of plants containing polyphenols other than those mentioned above include Eucalyptus plants. The part of the Eucalyptus plant used for extraction is not particularly limited, but examples thereof include leaves, fruits, buds, stems, roots, and the like, with leaves being particularly preferred.
【0020】抽出は植物の種類に応じて通常使用されて
いる方法を用いればよい。具体的には、例えば上記植物
(必要に応じて粉末などに加工されたもの)を水、有機
溶媒またはこれらの混合物などと混ぜ合わせて有効成分
を抽出する。有機溶媒としては、例えばメタノール、エ
タノール、プロパノール等の低級アルコール、アセト
ン、酢酸エチル、ジエチルエーテル等のエーテル類等が
挙げられる。抽出方法としては、特に制限はなく、常温
ホモジナイズ抽出、還流抽出、超臨界流体抽出などが使
用可能である。抽出後、必要に応じて、得られたエキス
を水飽和n−ブタノール、酢酸エチル等でさらに抽出を
行い、さらに得られた抽出エキスを水含有エタノール等
で抽出処理を行ってもよい。このようにして得られる抽
出物は、上記植物からの抽出処理によって得られるもの
ゆえ、分画および精製が不十分であっても安全性に問題
はない。Extraction may be carried out by a method which is usually used depending on the type of plant. Specifically, for example, the above-mentioned plant (which has been processed into powder or the like if necessary) is mixed with water, an organic solvent, a mixture thereof, or the like to extract the active ingredient. Examples of the organic solvent include lower alcohols such as methanol, ethanol and propanol, ethers such as acetone, ethyl acetate and diethyl ether. The extraction method is not particularly limited, and normal temperature homogenization extraction, reflux extraction, supercritical fluid extraction and the like can be used. After extraction, the obtained extract may be further extracted with water-saturated n-butanol, ethyl acetate or the like, and the obtained extract may be extracted with water-containing ethanol or the like. Since the extract thus obtained is obtained by the extraction treatment from the above plant, there is no problem in safety even if the fractionation and purification are insufficient.
【0021】抽出後、吸着クロマトグラフィー、分配ク
ロマトグラフィー、イオン交換クロマトグラフィー等を
使用してポリフェノールを単離し、さらに常法に従って
精製を行ってもよい。このようにして得られた抽出物
は、ポリフェノール塩の生成反応に供せられる。After the extraction, the polyphenol may be isolated by using adsorption chromatography, partition chromatography, ion exchange chromatography and the like, and further purified by a conventional method. The extract thus obtained is subjected to a reaction for producing a polyphenol salt.
【0022】上記のようにして得られたポリフェノール
含有植物の抽出液は、この抽出液に前記水酸化ナトリウ
ムなどのアルカリを添加しpHを約6.5〜7.0、好
ましくは約6.8〜7.0に調整することにより渋味等
が軽減される。アルカリは、前記ポリフェノール水溶液
に対して固体の形態で添加してもよいが、好ましくは水
溶液の形態で添加するのがよい。なお、必要に応じて、
抽出液を乾燥させて粉末などに加工することもできる。
粉末にする際には、必要に応じてデキストリンなどの添
加物を配合してもよい。乾燥させる手段は、特に限定さ
れず、例えば流動層乾燥器などを使用することができ
る。このようにして渋味等が軽減されたポリフェノール
含有抽出物は、該抽出物のまま摂取することもできる
が、後述するように、食品に添加して摂取することもで
きる。The polyphenol-containing plant extract obtained as described above has a pH of about 6.5 to 7.0, preferably about 6.8, by adding an alkali such as sodium hydroxide to the extract. By adjusting to ~ 7.0, the astringency and the like are reduced. The alkali may be added to the polyphenol aqueous solution in the form of a solid, but it is preferable to add the alkali in the form of an aqueous solution. If necessary,
The extract may be dried and processed into powder or the like.
When powdered, additives such as dextrin may be added as necessary. The means for drying is not particularly limited, and for example, a fluidized bed dryer or the like can be used. The polyphenol-containing extract in which the astringency and the like are reduced in this way can be ingested as it is, but can also be ingested by adding it to foods, as described later.
【0023】3.食品
本発明の食品は、(1)前記1で得られるポリフェノール
塩を食品に添加したもの、(2)前記2で中和処理した抽
出物を食品に添加したもの、および(3)ポリフェノール
を含有する食品にアルカリを直接添加して中和したもの
である。3. Food The food of the present invention contains (1) a product obtained by adding the polyphenol salt obtained in 1 above to a food product, (2) a product obtained by adding the extract neutralized in 2 above to a food product, and (3) a polyphenol It is obtained by directly adding an alkali to a food product.
【0024】前記食品としては、固形食品、クリーム状
ないしジャム状の半流動食品、ゲル状食品、飲料などの
他、これらに添加する食品添加物、食品素材などが挙げ
られ、具体的には、例えば飲料、焼き菓子、ガム、キャ
ンディー、チョコレート、グミ、ゼリー、乳製品、即席
麺、アイスクリーム、氷菓、パンなどが挙げられる。Examples of the foods include solid foods, cream-like or jam-like semi-liquid foods, gel foods, beverages and the like, as well as food additives and food materials added to these, specifically, Examples thereof include beverages, baked goods, gum, candy, chocolate, gummy, jelly, dairy products, instant noodles, ice cream, frozen desserts, and bread.
【0025】(1)ポリフェノール塩を食品に添加する場
合
ポリフェノール塩を食品に添加する際には、水溶液の形
態で添加してもよく、あるいは乾燥させて粉末などの固
体の形態で添加してもよい。ポリフェノール塩の食品へ
の添加量は特に限定されず、食品の形態、嗜好などに応
じて適宜決定すればよい。具体的には、例えば飲料の場
合、飲料100mLに対して約50〜100mgのポリ
フェノール塩を添加するのがよい。また、焼き菓子、ガ
ム、チョコレートなどの固形物の場合、固形物100g
に対して約50〜1000mgのポリフェノール塩を添
加するのがよい。(1) When adding polyphenol salt to food When adding polyphenol salt to food, it may be added in the form of an aqueous solution or may be dried and added in the form of solid such as powder. Good. The amount of the polyphenol salt added to the food is not particularly limited, and may be appropriately determined depending on the form of the food, taste and the like. Specifically, for example, in the case of a beverage, it is preferable to add about 50 to 100 mg of polyphenol salt to 100 mL of the beverage. In the case of solids such as baked goods, gum and chocolate, 100g of solids
It is advisable to add about 50 to 1000 mg of polyphenol salt.
【0026】(2)中和処理した抽出物を食品に添加する
場合
この抽出物を食品に添加する際にも、上記と同様に、水
溶液の形態で添加してもよく、あるいは乾燥させて粉末
などの固体の形態で添加してもよい。抽出物の食品への
添加量は特に限定されず、食品の形態、嗜好などに応じ
て適宜決定すればよい。具体的には、例えば飲料の場
合、飲料100mLに対して、飲料に含まれるポリフェ
ノール塩の量が約50〜100mgとなるようにポリフ
ェノール塩含有抽出物を添加するのがよい。また、焼き
菓子、ガム、チョコレートなどの固形物の場合、固形物
100gに対して、食品に含まれるポリフェノール塩の
量が約50〜1000mgとなるようにポリフェノール
塩含有抽出物を添加するのがよい。(2) Addition of Neutralized Extract to Food When adding this extract to food, it may be added in the form of an aqueous solution or powdered by drying, as described above. May be added in a solid form such as. The amount of the extract added to the food is not particularly limited and may be appropriately determined depending on the form of the food, taste and the like. Specifically, for example, in the case of a beverage, the polyphenol salt-containing extract is preferably added to 100 mL of the beverage so that the amount of the polyphenol salt contained in the beverage is about 50 to 100 mg. In the case of solids such as baked goods, gum, and chocolate, it is preferable to add the polyphenol salt-containing extract so that the amount of the polyphenol salt contained in the food is about 50 to 1000 mg based on 100 g of the solid. .
【0027】(3) ポリフェノールを含有する食品にアル
カリを直接添加して中和する場合
ポリフェノールを含有する食品に前記水酸化ナトリウム
などのアルカリを添加してpHを約6.5〜7.0、好
ましくは約6.8〜7.0に調整すればよい。アルカリ
は、固体の形態で前記ポリフェノール水溶液に添加して
もよいが、好ましくは水溶液で添加するのがよい。得ら
れた食品は、必要に応じて、液状、固形状、クリーム
状、ジャム状、ゲル状などの食品形態に加工することが
できる。これにより渋味等が軽減された食品が得られ
る。(3) When an alkali is directly added to a polyphenol-containing food to neutralize it, the alkali such as sodium hydroxide is added to the polyphenol-containing food to adjust the pH to about 6.5 to 7.0. Preferably, it may be adjusted to about 6.8 to 7.0. The alkali may be added to the polyphenol aqueous solution in the form of a solid, but it is preferable to add it as an aqueous solution. The obtained food can be processed into a liquid, solid, cream, jam, gel, or other food form, if necessary. As a result, a food product with reduced astringency is obtained.
【0028】なお、ポリフェノールを含有する食品に
は、食品を構成する素材にポリフェノールが元々含まれ
ていた場合や、食品にポリフェノールを後で添加した場
合などが含まれる。The food containing polyphenol includes the case where the material constituting the food originally contained polyphenol, the case where polyphenol was added to the food later, and the like.
【0029】ポリフェノール塩と共に食品に配合される
各種成分は特に制限はなく、通常使用される各種成分が
いずれも使用可能である。このような成分としては、例
えばブドウ糖、果糖、ショ糖、マルトース、ソルビトー
ル、ステビオサイド、コーンシロップ、乳糖、クエン
酸、酒石酸、リンゴ酸、コハク酸、乳酸、L−アスコル
ビン酸、dl−α−トコフェロール、グリセリン、プロ
ピレングリコール、グリセリン脂肪酸エステル、ポリグ
リセリン脂肪酸エステル、ショ糖脂肪酸エステル、ソル
ビタン脂肪酸エステル、プロピレングリコール脂肪酸エ
ステル、アラビアガム、カラギーナン、カゼイン、ゼラ
チン、ペクチン、寒天、ビタミンB群、ニコチン酸アミ
ド、パントテン酸カルシウム、アミノ酸類、カルシウム
塩類、色素、香料、保存剤等が挙げられ、これらを食品
の種類に応じて適宜配合すればよい。There are no particular restrictions on the various components that are blended in the food together with the polyphenol salt, and various commonly used components can be used. Examples of such components include glucose, fructose, sucrose, maltose, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid, succinic acid, lactic acid, L-ascorbic acid, dl-α-tocopherol, Glycerin, propylene glycol, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, propylene glycol fatty acid ester, gum arabic, carrageenan, casein, gelatin, pectin, agar, vitamin B group, nicotinic acid amide, pantothene Examples thereof include calcium acid, amino acids, calcium salts, dyes, flavors, preservatives, and the like, and these may be appropriately mixed depending on the type of food.
【0030】なお、上記pH調整には、前記アルカリ、
重曹、かん水などの他、ビタミンCなどを使用すること
ができる。また、本発明の食品は、前記(1)〜(3)を併用
した手段により得ることもできる。For adjusting the pH, the alkali,
In addition to baking soda and brackish water, vitamin C and the like can be used. Further, the food of the present invention can also be obtained by a means in which the above (1) to (3) are used in combination.
【0031】[0031]
【実施例】以下、実施例を挙げて本発明を詳細に説明す
るが、本発明は以下の実施例のみに限定されるものでは
ない。The present invention will be described in detail below with reference to examples, but the present invention is not limited to the following examples.
【0032】実施例1
<ポリフェノール塩の製造>日本新薬社製「カテピュ
ア」(成分:総ポリフェノール含量94.7%、総カテ
キン含量86.3%、エピガロカテキンガレート含量4
2.4%)1gをイオン交換水50gに溶解させた。得
られた水溶液のpHは約4.5であった。この水溶液を
0.1Nの水酸化ナトリウム水溶液で中和してpHを
7.0に調整した。中和された水溶液を凍結乾燥し、ポ
リフェノール塩約1gを得た。Example 1 <Production of polyphenol salt>"Catepure" manufactured by Nippon Shinyaku Co., Ltd. (components: total polyphenol content 94.7%, total catechin content 86.3%, epigallocatechin gallate content 4)
2.4%) 1 g was dissolved in 50 g of ion-exchanged water. The pH of the obtained aqueous solution was about 4.5. This aqueous solution was neutralized with a 0.1N aqueous sodium hydroxide solution to adjust the pH to 7.0. The neutralized aqueous solution was freeze-dried to obtain about 1 g of polyphenol salt.
【0033】実施例2
<緑茶飲料>容器に緑茶葉10gを入れ、80℃の水を
500g注いだ。5分後に緑茶葉を濾し取ることにより
緑茶抽出液を得た(pH約6)。この緑茶抽出液を室温
まで冷却した後、0.1Nの水酸化ナトリウム水溶液を
添加してpHを7.0に調整することにより緑茶飲料を
得た。Example 2 <Green Tea Beverage> 10 g of green tea leaf was placed in a container and 500 g of water at 80 ° C. was poured. After 5 minutes, the green tea leaf was filtered off to obtain a green tea extract (pH about 6). After cooling this green tea extract to room temperature, a 0.1N sodium hydroxide aqueous solution was added to adjust the pH to 7.0 to obtain a green tea beverage.
【0034】比較例1
水酸化ナトリウム水溶液で中和しない他は、実施例2と
同様にして緑茶飲料を得た。Comparative Example 1 A green tea beverage was obtained in the same manner as in Example 2 except that it was not neutralized with an aqueous sodium hydroxide solution.
【0035】比較例2
容器に実施例2の半分量の緑茶葉(5g)を入れ、水酸
化ナトリウム水溶液で中和しない他は、実施例2と同様
にして緑茶飲料を得た。Comparative Example 2 A green tea beverage was obtained in the same manner as in Example 2 except that half the amount of green tea leaves (5 g) of Example 2 was placed in a container and was not neutralized with an aqueous sodium hydroxide solution.
【0036】実施例2、比較例1および比較例2で得ら
れた緑茶飲料を5名の専門パネラーで飲み比べたとこ
ろ、専門パネラー全員が、比較例1は過剰な渋味があ
り、比較例1と緑茶葉が同量の実施例2は程良い渋味で
あり、緑茶葉の量が実施例2の半分である比較例2は実
施例2と同程度の程良い渋味であったと回答した。When the green tea beverages obtained in Example 2, Comparative Example 1 and Comparative Example 2 were compared with each other by 5 expert panelists, all the expert panelists had an excessive astringency in Comparative Example 1, and Example 2 in which the amount of green tea leaves was the same as that of Example 1 had a moderate astringency, and Comparative Example 2 in which the amount of green tea leaves was half that of Example 2 had a moderate astringency similar to that of Example 2. did.
【0037】実施例3
<混合茶飲料>表1に示す割合で茶葉および水を容器に
入れて混合した。Example 3 <Mixed Tea Beverage> Tea leaves and water were put in a container at a ratio shown in Table 1 and mixed.
【表1】
10分後に茶葉を濾し取ることにより混合茶抽出液を得
た(pH約6)。この抽出液に重曹を添加してpHを
7.0に調整し、室温まで冷却した。ついで、冷却した
抽出液1000gに実施例1で得たポリフェノール塩を
0.5g添加することにより混合茶飲料を得た(pH
7.0)。[Table 1] After 10 minutes, the tea leaves were filtered off to obtain a mixed tea extract (pH about 6). Sodium bicarbonate was added to this extract to adjust the pH to 7.0, and the mixture was cooled to room temperature. Then, 0.5 g of the polyphenol salt obtained in Example 1 was added to 1000 g of the cooled extract to obtain a mixed tea beverage (pH
7.0).
【0038】比較例3
実施例1で得たポリフェノール塩に代えて、日本新薬社
製「カテピュア」(前出)を0.5g添加した他は、実
施例3と同様にして混合茶飲料を得た。Comparative Example 3 A mixed tea beverage was obtained in the same manner as in Example 3 except that 0.5 g of "Catepure" (described above) manufactured by Nippon Shinyaku Co., Ltd. was added instead of the polyphenol salt obtained in Example 1. It was
【0039】実施例3および比較例3で得られた混合茶
飲料を5名の専門パネラーで飲み比べたところ、専門パ
ネラー全員が、比較例3は過剰な渋味があり、実施例3
は程良い渋味であったと回答した。When the mixed tea beverages obtained in Example 3 and Comparative Example 3 were compared with each other by 5 specialized panelists, all of the specialized panelists had an excessive astringency in Comparative Example 3, and Example 3
Replied that it had a good astringency.
【0040】実施例4
<クッキー>表2に示す材料を用いて、クッキーを下記
手順で作製した。Example 4 <Cookie> Using the materials shown in Table 2, a cookie was prepared by the following procedure.
【表2】
(作製手順)
(1)バターをクリーム状になるまでよく撹拌した。
(2)撹拌したバターに粉糖を3回に分けて加え、混ぜ合
わせた。次に卵黄を入れてさらに撹拌した。
(3)これにベーキングパウダーと実施例1で得たポリフ
ェノール塩とを混ぜ合わせ、さらに、ふるいにかけた小
麦粉を60g加えてよく撹拌した。ついで、残りの小麦
粉を加えてよく撹拌し、冷蔵庫で1時間寝かせた。
(4)ついで、冷蔵庫から取り出した混合物を直径3cm
の棒状に形作った。
(5)これをラップフィルムで包み、冷蔵庫で十分に固く
なるまで冷却した。
(6)ついで、冷蔵庫から取り出した棒状の固形物を厚さ
5〜6mm程度の輪切りにした。
(7)輪切りにした固形物を予め180℃に熱したオーブ
ンに入れて適当な時間焼き上げて、クッキーを得た。[Table 2] (Preparation procedure) (1) The butter was stirred well until it became creamy. (2) Powdered sugar was added to the stirred butter in 3 portions and mixed. Next, egg yolk was added and further stirred. (3) The baking powder and the polyphenol salt obtained in Example 1 were mixed with this, and 60 g of sieved wheat flour was added and stirred well. Then, the rest of the flour was added, and the mixture was stirred well and left to stand in the refrigerator for 1 hour. (4) Then, the mixture taken out from the refrigerator is 3 cm in diameter.
Shaped like a stick. (5) This was wrapped with wrap film and cooled in a refrigerator until it became sufficiently hard. (6) Then, the rod-shaped solid substance taken out from the refrigerator was cut into slices having a thickness of about 5 to 6 mm. (7) The sliced solid matter was placed in an oven preheated to 180 ° C. and baked for an appropriate time to obtain a cookie.
【0041】実施例5
ポリフェノール塩の添加量を3gとし、小麦粉の添加量
を237gとした他は、実施例4と同様にしてクッキー
を作製した。Example 5 A cookie was prepared in the same manner as in Example 4 except that the amount of polyphenol salt added was 3 g and the amount of wheat flour added was 237 g.
【0042】実施例6
ポリフェノール塩の添加量を5gとし、小麦粉の添加量
を235gとした他は、実施例4と同様にしてクッキー
を作製した。Example 6 A cookie was prepared in the same manner as in Example 4 except that the amount of polyphenol salt added was 5 g and the amount of wheat flour added was 235 g.
【0043】比較例4
ポリフェノール塩に代えて日本新薬社製「カテピュア」
(前出)を1g添加した他は、実施例4と同様にして、
クッキーを作製した。Comparative Example 4 "Catepure" manufactured by Nippon Shinyaku Co., Ltd. in place of the polyphenol salt
In the same manner as in Example 4 except that 1 g (of the above) was added,
I made a cookie.
【0044】比較例5
ポリフェノール塩に代えて日本新薬社製「カテピュア」
を3g添加し、小麦粉の添加量を237gとした他は、
実施例4と同様にしてクッキーを作製した。Comparative Example 5 "Catepure" manufactured by Nippon Shinyaku Co., Ltd. in place of the polyphenol salt
Except that the amount of wheat flour added was 237 g,
A cookie was prepared in the same manner as in Example 4.
【0045】比較例6
ポリフェノール塩に代えて日本新薬社製「カテピュア」
を5g添加し、小麦粉の添加量を235gとした他は、
実施例4と同様にしてクッキーを作製した。Comparative Example 6 "Catepure" manufactured by Nippon Shinyaku Co., Ltd. in place of the polyphenol salt
Except that the amount of wheat flour added was 235 g,
A cookie was prepared in the same manner as in Example 4.
【0046】実施例4〜6および比較例4〜6で得られ
たクッキーの渋味、苦味および収斂味について官能検査
を実施した。評価は、6名の専門パネラーが以下の評価
基準で実施した。検査の結果、それぞれの評価基準に該
当した人数を表3に示す。
(評価基準)
○:渋味、苦味および収斂味を感じない。
△:わずかに渋味、苦味および収斂味を感じる。
×:かなり渋味、苦味および収斂味を感じる。Sensory tests were carried out on the astringency, bitterness and astringency of the cookies obtained in Examples 4 to 6 and Comparative Examples 4 to 6. The evaluation was performed by 6 professional panelists based on the following evaluation criteria. Table 3 shows the number of people who met the respective evaluation criteria as a result of the inspection. (Evaluation Criteria) ○: Astringency, bitterness and astringency are not felt. Δ: Slightly astringent, bitter and astringent. X: A fairly astringent, bitter and astringent taste is felt.
【表3】 [Table 3]
【0047】表3に示すように、ポリフェノール塩を添
加した実施例4〜6の方が、「カテピュア」を添加した
比較例4〜6よりも渋味、苦味および収斂味が軽減され
ていることがわかった。As shown in Table 3, the astringency, bitterness and astringent taste were reduced in Examples 4 to 6 to which the polyphenol salt was added, as compared to Comparative Examples 4 to 6 to which "Catepure" was added. I understood.
【0048】試験例1
<渋味等の軽減効果の確認>日本新薬社製「カテピュ
ア」の水溶液Aおよび実施例1で得たポリフェノール塩
の水溶液Bの渋味、苦味および収斂味について官能検査
を実施した。すなわち、「カテピュア」および前記ポリ
フェノール塩をそれぞれイオン交換水で希釈し、0.1
25重量%の水溶液AおよびBをそれぞれ得た。つい
で、水溶液Aの渋味、苦味および収斂味が水溶液Bの渋
味、苦味および収斂味と同程度になるまで水溶液Aをイ
オン交換水で徐々に希釈し、官能検査を繰り返した。評
価は、専門パネラー5名にて実施した。その結果、水溶
液Aと水溶液Bの渋味、苦味および収斂味が同等になっ
たと専門パネラー全員が判断した時、水溶液Aの濃度は
0.04重量%であった。これにより、実施例1で得た
ポリフェノール塩の渋味、苦味および収斂味は、「カテ
ピュア」の約1/3に軽減されていると言える。Test Example 1 <Confirmation of the effect of reducing astringency and the like> A sensory test was conducted on the astringency, bitterness and astringency of the aqueous solution A of "Catepure" manufactured by Nippon Shinyaku Co., Ltd. and the aqueous solution B of the polyphenol salt obtained in Example 1. Carried out. That is, "catapure" and the polyphenol salt are diluted with ion-exchanged water to give 0.1
25 wt% aqueous solutions A and B were obtained respectively. Then, the aqueous solution A was gradually diluted with ion-exchanged water until the astringency, bitterness and astringent taste of the aqueous solution A became similar to the astringency, bitterness and astringent taste of the aqueous solution B, and the sensory test was repeated. The evaluation was carried out by 5 specialized panelists. As a result, when all the expert panelists judged that the astringency, bitterness and astringency of the aqueous solution A and the aqueous solution B were equal, the concentration of the aqueous solution A was 0.04% by weight. Thus, it can be said that the astringency, bitterness and astringency of the polyphenol salt obtained in Example 1 are reduced to about 1/3 that of "catapure".
【0049】試験例2
<pHとポリフェノール構造との関係>エピガロカテキ
ンガレート(以下、「EGCg」という。)水溶液中に
おけるEGCgの構造と水溶液のpHとの関係について
調べるために、以下の試験を実施した。Test Example 2 <Relationship between pH and polyphenol structure> In order to investigate the relationship between the structure of EGCg in an aqueous solution of epigallocatechin gallate (hereinafter referred to as "EGCg") and the pH of the aqueous solution, the following test was conducted. Carried out.
【0050】EGCg(純度80%)1gをイオン交換
水500mlに溶解し、pH4.5のEGCg水溶液を
得た。このEGCg水溶液に0.1Nの水酸化ナトリウ
ム水溶液を適量添加することによってpHを上げ、pH
が5.0、5.9、6.5および7.0のEGCg水溶
液をそれぞれ得た。ついで、pH7.0のEGCg水溶
液の一部を採取し、これに0.1Nの塩酸を適量添加す
ることによってpHを下げ、pHが6.5、6.0、
5.3、3.9、3.0および2.2のEGCg水溶液
をそれぞれ得た。1 g of EGCg (purity 80%) was dissolved in 500 ml of deionized water to obtain an EGCg aqueous solution having a pH of 4.5. The pH is raised by adding an appropriate amount of 0.1N sodium hydroxide aqueous solution to this EGCg aqueous solution,
To obtain EGCg aqueous solutions of 5.0, 5.9, 6.5 and 7.0, respectively. Next, a part of the EGCg aqueous solution having a pH of 7.0 was collected, and the pH was lowered by adding an appropriate amount of 0.1 N hydrochloric acid to the pH of 6.5, 6.0,
EGCg aqueous solutions of 5.3, 3.9, 3.0 and 2.2 were obtained, respectively.
【0051】上記のようにしてpHを変化させた11種
類のEGCg水溶液のUV吸収スペクトルをそれぞれ測
定した。測定には、島津製作所社製のUV2200Aを
用いた。この測定により得られた各水溶液の吸収スペク
トルには、波長273nm付近にピークが生じていた。
このピークはフェノール性水酸基の吸収スペクトルであ
る。したがって、このピーク高さを比較することによっ
て、EGCg水溶液中のEGCgの構造変化を評価する
ことができる。すなわち、ピーク高さが低いほど、フェ
ノール性水酸基の水素原子がナトリウムに置換されてい
ることを示している。The UV absorption spectra of 11 kinds of EGCg aqueous solutions having different pH values were measured as described above. UV2200A manufactured by Shimadzu Corporation was used for the measurement. The absorption spectrum of each aqueous solution obtained by this measurement had a peak near a wavelength of 273 nm.
This peak is an absorption spectrum of a phenolic hydroxyl group. Therefore, by comparing the peak heights, the structural change of EGCg in the EGCg aqueous solution can be evaluated. That is, the lower the peak height is, the more the hydrogen atom of the phenolic hydroxyl group is replaced with sodium.
【0052】図1は、波長273nm付近のピーク高さ
とEGCg水溶液のpHとの関係を示したグラフであ
る。図1に示すように、水酸化ナトリウム水溶液により
pHを4.5から7.0に変化させていく過程(図1中
に黒丸でプロット)において、pH6.0付近からピー
ク高さが急激に低下している。すなわち、pH6.0付
近からEGCg水溶液中のポリフェノール塩(EGCg
ナトリウム塩)が急激に増加して、フェノール性水酸基
が急激に減少していることを示している。FIG. 1 is a graph showing the relationship between the peak height near the wavelength of 273 nm and the pH of the EGCg aqueous solution. As shown in Fig. 1, in the process of changing the pH from 4.5 to 7.0 with an aqueous sodium hydroxide solution (plotted with black circles in Fig. 1), the peak height sharply decreased from around pH 6.0. is doing. That is, the polyphenol salt (EGCg in the EGCg aqueous solution from about pH 6.0)
It shows that the sodium salt) sharply increases and the phenolic hydroxyl group sharply decreases.
【0053】一方、塩酸によりpHを7.0から2.2
に変化させていく過程(図1中に白三角でプロット)に
おいては、pH7.0から6.0にかけて急激にピーク
高さが高くなっており、その後もpH2.2まで徐々に
ピーク高さが高くなっている。すなわち、pHが低くな
るにつれてフェノール性水酸基が復元され、増加してい
ることがわかる。この場合、pHが6.5まで低下した
時点では、フェノール性水酸基の復元率(pH4.5の
EGCg水溶液を基準とする。)は38%に満たない
が、pHが2.2まで低下すると復元率は約92%であ
った。On the other hand, the pH was adjusted to 7.0 to 2.2 with hydrochloric acid.
In the process of changing to (indicated by a white triangle in FIG. 1), the peak height increased sharply from pH 7.0 to 6.0, and thereafter, the peak height gradually increased to pH 2.2. It's getting higher. That is, it can be seen that the phenolic hydroxyl group is restored and increases as the pH decreases. In this case, the restoration rate of the phenolic hydroxyl group (based on the EGCg aqueous solution of pH 4.5) is less than 38% at the time when the pH is reduced to 6.5, but it is restored when the pH is reduced to 2.2. The rate was about 92%.
【0054】以上の結果より、EGCg水溶液のpHが
6.5程度の弱酸性環境下ないしpHが7.0程度の中
性環境下においては、EGCgのフェノール性水酸基の
水素原子の多くがナトリウムに置換される、すなわち渋
味軽減効果が得られるが、これが胃内のような酸性環境
下に置かれるとほとんどのフェノール性水酸基が復元さ
れる、すなわちポリフェノール本来の生理活性が発揮さ
れる状態に復元されることがわかる。From the above results, in a weak acidic environment where the pH of the EGCg aqueous solution is about 6.5 or in a neutral environment where the pH is about 7.0, most of the hydrogen atoms of the phenolic hydroxyl group of EGCg are converted to sodium. It is replaced, that is, the astringency-relieving effect is obtained, but when it is placed in an acidic environment such as the stomach, most of the phenolic hydroxyl groups are restored, that is, the state where the polyphenol's original physiological activity is exerted is restored. I understand that it will be done.
【0055】[0055]
【発明の効果】本発明のポリフェノール塩は、ポリフェ
ノールのナトリウム塩、カルシウム塩、マグネシウム塩
またはカリウム塩であるので、渋味等が軽減されてお
り、多量摂取が可能であり、しかも胃内の酸性下では元
のポリフェノールに戻るので、多量摂取による高い生理
活性効果が期待され、また、ポリフェノール塩は、ポリ
フェノールと比較して、水溶性が向上するので、水溶液
とした場合に濁りや沈殿物が生じにくいという効果があ
る。Since the polyphenol salt of the present invention is a sodium salt, calcium salt, magnesium salt or potassium salt of polyphenol, it has a reduced astringency and the like and can be ingested in a large amount and has an acidity in the stomach. Since it returns to the original polyphenol below, it is expected to have a high physiological activity effect by a large intake, and since the polyphenol salt has improved water solubility compared to polyphenol, turbidity and precipitates will occur when made into an aqueous solution. It has the effect of being difficult.
【0056】本発明の食品は、ポリフェノールをアルカ
リで中和したポリフェノール塩を含有しているので、渋
味等が軽減されており、該食品に含まれたポリフェノー
ル塩の多量摂取が可能であり、しかも胃内の酸性下では
元のポリフェノールに戻るので、多量摂取による高い生
理活性効果が期待できるという効果がある。Since the food of the present invention contains a polyphenol salt obtained by neutralizing polyphenol with an alkali, astringency and the like are reduced, and a large amount of the polyphenol salt contained in the food can be ingested. Moreover, since it returns to the original polyphenol under acidic conditions in the stomach, there is an effect that a high physiological activity effect can be expected by a large intake.
【0057】本発明の飲料は、ポリフェノール含有抽出
液をアルカリで中和しているので、渋味等が軽減されて
おり、ポリフェノール塩の多量摂取が可能であり、しか
も胃内の酸性下では元のポリフェノールに戻るので、多
量摂取による高い生理活性効果が期待できるという効果
がある。In the beverage of the present invention, since the polyphenol-containing extract is neutralized with an alkali, the astringency and the like are reduced, and a large amount of polyphenol salt can be ingested. Since it returns to the polyphenol, it has the effect that a high physiological activity effect can be expected by a large intake.
【図1】EGCg水溶液のUV吸収スペクトルにおける
波長273nm付近のピーク高さとEGCg水溶液のp
Hとの関係を示したグラフである。FIG. 1 is a peak height around a wavelength of 273 nm in the UV absorption spectrum of an EGCg aqueous solution and p of the EGCg aqueous solution.
It is a graph showing the relationship with H.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.7 識別記号 FI テーマコート゛(参考) // A21D 13/08 A23L 2/00 F 4C062 (72)発明者 古川 靖 大阪府茨木市五日市1丁目3番30号 長岡 香料株式会社技術開発研究所内 (72)発明者 竹内 弘明 大阪府茨木市五日市1丁目3番30号 長岡 香料株式会社技術開発研究所内 Fターム(参考) 4B017 LC02 LC03 LG14 LK01 LK06 LL09 LP01 4B018 LB01 LB08 MD02 MD03 MD04 MD08 MD59 MD60 ME04 ME06 ME07 ME09 MF01 MF06 4B027 FB01 FB10 FC02 FC06 FK01 FK02 FK09 FP72 FP74 4B032 DB21 DK01 DK05 DK29 DL06 DL20 4B035 LC01 LG01 LG02 LG04 LG31 LK19 LP22 LP56 4C062 FF11 FF90 ─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. 7 Identification code FI theme code (reference) // A21D 13/08 A23L 2/00 F 4C062 (72) Inventor Yasushi Furukawa 1-3, Itokaichi, Ibaraki, Osaka No. 30 Nagaoka Fragrance Co., Ltd. Technology Development Laboratory (72) Inventor Hiroaki Takeuchi 1-3-30 Gokaichi, Ibaraki, Osaka Prefecture Nagaoka Fragrance Co., Ltd. Technical Development Laboratory F-term (reference) 4B017 LC02 LC03 LG14 LK01 LK06 LL09 LP01 4B018 LB01 LB08 MD02 MD03 MD04 MD08 MD59 MD60 ME04 ME06 ME07 ME09 MF01 MF06 4B027 FB01 FB10 FC02 FC06 FK01 FK02 FK09 FP72 FP74 4B032 DB21 DK01 DK05 DK29 DL06 LG21 LG90LF22 LG31 LG02 LG22 LG04 LG04 LG22 LG04 LG22
Claims (7)
ム塩、マグネシウム塩またはカリウム塩であるポリフェ
ノール塩。1. A polyphenol salt which is a sodium salt, calcium salt, magnesium salt or potassium salt of polyphenol.
ることを特徴とする食品。2. A food containing the polyphenol salt according to claim 1.
酸化マグネシウムおよび水酸化カリウムよりなる群から
選ばれるアルカリで中和したポリフェノール含有植物の
抽出物を含有することを特徴とする食品。3. A food product comprising an extract of a polyphenol-containing plant neutralized with an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide.
ョコレート、グミ、ゼリー、乳製品、即席麺、アイスク
リーム、氷菓またはパンである請求項2または3記載の
食品。4. The food according to claim 2 or 3, which is a beverage, baked goods, gum, candy, chocolate, gummy, jelly, dairy product, instant noodles, ice cream, frozen dessert or bread.
ナトリウム、水酸化カルシウム、水酸化マグネシウムお
よび水酸化カリウムよりなる群から選ばれるアルカリで
中和して得られる飲料。5. A beverage obtained by neutralizing an extract of tea leaves containing polyphenol with an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide.
化カルシウム、水酸化マグネシウムおよび水酸化カリウ
ムよりなる群から選ばれるアルカリと反応させてポリフ
ェノール塩とすることを特徴とするポリフェノールの渋
味、苦味または収斂味の軽減方法。6. Astringency, bitterness or astringency of polyphenol, characterized by reacting polyphenol with an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide to form a polyphenol salt. How to reduce taste.
ナトリウム、水酸化カルシウム、水酸化マグネシウムお
よび水酸化カリウムよりなる群から選ばれるアルカリで
中和することを特徴とする、ポリフェノール含有抽出物
の渋味、苦味または収斂味の軽減方法。7. An astringent a polyphenol-containing extract, characterized in that the extract of a polyphenol-containing plant is neutralized with an alkali selected from the group consisting of sodium hydroxide, calcium hydroxide, magnesium hydroxide and potassium hydroxide. How to reduce taste, bitterness or astringency.
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