JP5300461B2 - Chlorogenic acid bitterness masking agent - Google Patents

Description

  The present invention relates to a bitterness masking agent specific to chlorogenic acid.

  Chlorogenic acid is attracting attention as an antioxidant that removes active oxygen that causes cancer and aging. It has also been shown to have antimutagenic activity that suppresses the production of carcinogen nitrosamines in the body and inactivates the movement of nitroso compounds.

  Although chlorogenic acid is useful as an antioxidant and the like, there is a problem that it is difficult to ingest due to its bitter taste. A typical beverage containing chlorogenic acid is a coffee beverage. In particular, among coffee beverages, black coffee and straight coffee have a problem that it is difficult to continue drinking due to the strength of the taste, especially bitterness and irritation to the stomach.

  As a method of removing the bitter taste of polyphenols, a method of bonding with a compound such as amines containing amino groups, amino acids, or heat treatment with saccharides is disclosed (Patent Document 1). Although this method is based on the knowledge that polyphenols bind to a compound having an amino group relatively easily, there is no disclosure regarding chlorogenic acid and coffee beverages.

Moreover, the method of adding protein, a peptide, or an amino acid in the manufacturing process of a coffee drink is examined from viewpoints, such as flavor deterioration suppression of coffee drink, prevention of precipitation, etc. (patent documents 2-7).
JP 2000-287630 A JP 2002-186425 A Japanese Patent Laid-Open No. 11-9190 JP 2002-119210 A JP-A-7-87891 JP-A-4-20244 JP 2007-166940 A

  As described above, although chlorogenic acid is useful as an antioxidant and the like, there is a problem that it is difficult to ingest due to its bitter taste. For example, with regard to coffee beverages that contain chlorogenic acid and one of the main ingredients of its bitterness is chlorogenic acid, many consumers prefer coffee whose bitterness is masked with sugar or milk. Yes. However, the method of masking the bitter taste by adding milk or sugar has a problem that it may cause cavities and obesity, and will be avoided from those who are diet- or health-conscious.

  In view of the above-mentioned present situation, an object of the present invention is to provide a bitterness masking agent for chlorogenic acid.

  As a result of intensive studies to solve the above problems, the present inventors have found that the bitterness caused by chlorogenic acid can be remarkably masked by adding a certain type of amino acid. The present invention was completed by finding that it is easy to drink while having the flavor of.

  That is, the present invention relates to a chlorogenic acid bitterness masking agent containing one or more amino acids selected from L-ornithine hydrochloride, D, L-alanine, L-valine and glycine.

  The present invention also relates to a bitterness masking agent for a chlorogenic acid-containing beverage, which comprises one or more amino acids selected from L-ornithine hydrochloride, D, L-alanine, L-valine and glycine.

  Furthermore, the present invention contains (A) chlorogenic acid and (B) L-ornithine hydrochloride, and the content ratio (weight ratio) of component (A) to component (B) is 1 (B) / (A). The present invention relates to a chlorogenic acid-containing beverage that is 0.0 or more.

  Moreover, this invention contains (A) chlorogenic acid and (B) D, L-alanine, and the content ratio (weight ratio) of a component (A) and a component (B) is (B) / (A) is 1. The present invention relates to a chlorogenic acid-containing beverage that is 0.0 or more.

  The present invention contains (A) chlorogenic acid and (B) L-valine, and the content ratio (weight ratio) of component (A) to component (B) is (B) / (A) of 1.0 or more. The present invention relates to a chlorogenic acid-containing beverage.

  The present invention also includes (A) chlorogenic acid and (B) glycine, and the content ratio (weight ratio) of component (A) to component (B) is (B) / (A) is 1.0 or more. It relates to a chlorogenic acid-containing beverage.

  Furthermore, the present invention comprises (A) chlorogenic acid and (B) one or more amino acids selected from L-ornithine hydrochloride, D, L-alanine, L-valine, and glycine, The content ratio (weight ratio) of a component (B) is related with the chlorogenic acid containing drink whose (B) / (A) is 1.0 or more.

  Moreover, this invention is a masking method of the bitter taste of a chlorogenic acid containing drink, Comprising: With respect to (A) chlorogenic acid, it is selected from (B) L-ornithine hydrochloride, D, L-alanine, L-valine, and glycine. Adding one or more amino acids together so that the content ratio (weight ratio) of component (B) to component (A) is at least component (B) / (A) = 1.0. Said method.

  ADVANTAGE OF THE INVENTION According to this invention, the bitter taste of chlorogenic acid is masked, The drink which is easy to drink while having the original flavor of a chlorogenic acid containing drink, and a drink favored by the direction of a health consciousness are provided.

(1) Chlorogenic acid bitterness masking agent and masking method The chlorogenic acid bitterness masking agent of the present invention is one or more amino acids selected from L-ornithine hydrochloride, D, L-alanine, L-valine, and glycine. including.

  The amino acid contained is selected from L-ornithine hydrochloride, D, L-alanine, L-valine, glycine. Among these, D, L-alanine or glycine is preferable. These amino acids may be contained alone or in combination of two or more. In addition, amino acids other than the above amino acids may also be included.

  L-ornithine hydrochloride, D, L-alanine, L-valine and glycine may be either natural or synthetic. L-ornithine hydrochloride is generally known to have an effect of protein synthesis and muscle strengthening by promoting the secretion of growth hormone. D, L-alanine is generally known to have fat burning, collagen regeneration, liver function improvement, and alcohol metabolism promoting action. Glycine is generally used for the treatment of hypoglycemia, hyperacidity and the like. L-valine is deeply involved in human growth and is generally known to have an effect of adjusting the nitrogen balance in blood. The above-mentioned effects can be expected from the masking agent of the present invention.

  The masking agent of the present invention can be added, for example, in the production process of a chlorogenic acid-containing beverage to obtain a beverage in which the bitterness derived from chlorogenic acid is masked. A representative example of the chlorogenic acid-containing beverage is coffee. The coffee beverage may be any so-called coffee beverage such as black coffee, coffee with milk, coffee with sugar, coffee with milk sugar, etc., but is preferably black coffee. The masking agent of the present invention can also be used by consumers by adding it to drip coffee or commercially available instant coffee.

  The amount of the masking agent added to the chlorogenic acid-containing beverage may be equal to or greater than the amount that shows the effect of suppressing the bitter taste of chlorogenic acid. That is, a certain amount or more may be added with respect to the chlorogenic acid content.

  Chlorogenic acid is 5-caffeoylquinic acid in monocaffeoylquinic acid. In coffee, monocaffeoylquinic acid other than 5-caffeoylquinic acid, ferulaquinic acid, and dicaffeoylquinic acid also exist, and chlorogenic acids other than 5-caffeoylquinic acid are called. Although all the above components are contained in the green coffee beans, 5-caffeoylquinic acid (ie, chlorogenic acid) is the most abundant.

(2) Chlorogenic acid-containing beverage The chlorogenic acid-containing beverage of the present invention is added with one or more amino acids selected from L-ornithine hydrochloride, D, L-alanine, L-valine, and glycine. Features.

  The chlorogenic acid-containing beverage of the present invention suppresses the bitter taste of chlorogenic acid by adding one or more amino acids selected from L-ornithine hydrochloride, D, L-alanine, L-valine and glycine. It is a drink that is easy to drink.

  The chlorogenic acid-containing beverage includes all beverages containing chlorogenic acid. Examples include juice drinks with addition of coffee, black tea, green tea, fruit juice or vegetable juice, soft drinks with carbonates, soft drinks without addition of fruit juices, and the like.

  The coffee beverage may be any so-called coffee beverage such as black coffee, coffee with milk, coffee with sugar, coffee with milk sugar, etc., preferably black coffee. Black coffee refers to so-called sugar-free black coffee that does not use sweeteners such as sugar and artificial sweeteners or milk. Moreover, those coffee drinks may be hot or iced. Further, chlorogenic acid may be added to the coffee beverage. In the case of a coffee beverage, an additive added to the coffee beverage, for example, a pH adjuster, an emulsifier, a fragrance and the like may be included.

The present invention can also be applied to foods that preferably mask coffee-derived bitterness, such as coffee jelly.
The added amino acid is selected from L-ornithine hydrochloride, D, L-alanine, L-valine, glycine. Among these, D, L-alanine or glycine is preferable. These amino acids may be added alone or in combination of two or more. In addition, amino acids other than the above amino acids may be added.

  L-ornithine hydrochloride, D, L-alanine, L-valine and glycine may be either natural or synthetic. L-ornithine hydrochloride is generally known to have an effect of protein synthesis and muscle strengthening by promoting the secretion of growth hormone. D, L-alanine is generally known to have fat burning, collagen regeneration, liver function improvement, and alcohol metabolism promoting action. Glycine is generally used for the treatment of hypoglycemia, hyperacidity and the like. L-valine is deeply involved in human growth and is generally known to have an effect of adjusting the nitrogen balance in blood. By adding L-ornithine hydrochloride, D, L-alanine, L-valine, and glycine to a chlorogenic acid-containing beverage, the above-mentioned effects can be expected.

  The amount of amino acid to be added may be equal to or greater than the amount that shows the effect of suppressing the bitter taste of chlorogenic acid. For example, in the case of a coffee beverage, a certain amount or more may be added with respect to the chlorogenic acid content contained in the coffee beverage.

  The amount of amino acid added that shows the bitterness-inhibiting effect of the chlorogenic acid-containing beverage is i) (A) content ratio (weight ratio) of (B) D, L-ornithine hydrochloride (B) / (A). 1.0 or more, ii) (A) chlorogenic acid and (B) L-alanine content ratio (weight ratio) (B) / (A) is 1.0 or more, iii) (A) chlorogenic acid and (B) L-valine content ratio (weight ratio) (B) / (A) is 1.0 or more, or iv) (A) chlorogenic acid and (B) glycine content ratio (weight ratio) (B) / (A) Is 1.0 or more.

Moreover, these amino acids can also add 2 or more types, (B) The content ratio (weight ratio) of the said amino acid total amount (B) / (A) is 1.0 or more with respect to (A) chlorogenic acid. It is.
More preferably, i) (A) chlorogenic acid and (B) D, L-ornithine hydrochloride content ratio (weight ratio) (B) / (A) is 1.5 or more, ii) (A) chlorogenic acid and (B) Content ratio (weight ratio) of L-alanine (B) / (A) is 1.5 or more, iii) Content ratio (weight ratio) of (A) chlorogenic acid and (B) L-valine (B) / (A) is 1.5 or more, or iv) The content ratio (weight ratio) (B) / (A) of (A) chlorogenic acid and (B) glycine is 1.5 or more. When two or more of these amino acids are added, the content ratio (weight ratio) of (B) total amino acid to (A) chlorogenic acid is (B) / (A) is 1.5 or more.

  Most preferably, i) (A) chlorogenic acid and (B) D, L-ornithine hydrochloride content ratio (weight ratio) (B) / (A) is 3.0 or more, ii) (A) chlorogenic acid and (B) Content ratio (weight ratio) of L-alanine (B) / (A) is 3.0 or more, iii) Content ratio (weight ratio) of (A) chlorogenic acid and (B) L-valine (B) / (A) is 3.0 or more, or iv) The content ratio (weight ratio) (B) / (A) of (A) chlorogenic acid and (B) glycine is 3.0 or more. When two or more of these amino acids are added, the content ratio (weight ratio) of (B) the total amount of amino acids to (A) chlorogenic acid is (B) / (A) is 3.0 or more.

Commercially available coffee beverages contain 20 mg / 100 ml to 150 mg / 100 ml of chlorogenic acid.
Further, even when these 4 types of amino acids are added to black coffee at 5 mg / ml, the coffee beverage of the present invention is also excellent in that it has no off-taste due to the added amino acids and has excellent palatability. One.

  The amount of chlorogenic acids can be quantified by HPLC analysis or the like. Also, the amount of chlorogenic acid (5-caffeoylquinic acid) itself can be quantified by a general method such as HPLC analysis, for example (Survey Report of Agricultural and Forestry Standard Laboratory (No. 10)) Chromatographic determination of chlorogenic acids and caffeine in coffee beverages ”, March 1986).

  The airtight container filled with the beverage is not limited to a can, but may have any form such as a bottle or a bag. Moreover, filling, sealing, deoxygenation method, sterilization method and the like of beverages in these containers can be performed with all information.

The present invention will be described in more detail with reference to examples, but the scope of the present invention is not limited to these examples.
[Example 1] Masking effect of various amino acids on the bitter taste of black coffee 2 g of commercially available instant coffee was dissolved in 140 ml of hot water to prepare black coffee (chlorogenic acids: 56-84 mg / 100 ml).

  2. Various amino acids (glycine, L-serine, L-ornithine hydrochloride, D, L-alanine, L-alanine, L-proline, L-threonine, L-phenylalanine, L-valine, L-lysine, L-leucine, L -Isoleucine, L-histidine hydrochloride, L-arginine, L-glutamate Na, L-aspartate Na, L-glutamate, L-tryptophan, L-cystine, L-tyrosine) 0.21 mg / ml. 42mg, 0.83mg, 1.67mg, 5.00mg each Added to the black coffee prepared in

  3. A panel of three people subjectively evaluated the bitterness masking effect of various amino acids on coffee (◎ bitterness is well masked; ○ bitterness is masked; △ bitterness is slightly felt; × bitterness is strongly felt) . At the same time, for black coffee to which various amino acids were added at a concentration of 5.00 mg / ml, the taste was evaluated subjectively by three panels. (◎ very good; ○ good; △ somewhat bad; × bad).

  As a result, it was found that in a system in which L-ornithine hydrochloride, D, L-alanine, L-valine, glycine and the like were added at 5.00 mg / ml, bitterness was masked and a coffee with excellent taste was obtained. .

尚、クロロゲン酸類の分析方法は以下のとおりである。クロロゲン酸類は、試料となるコーヒー飲料を０．４５μｍのメンブランフィルターで濾過した後、ＨＰＬＣに注入して定量した。測定条件は以下のとおり。

In addition, the analysis method of chlorogenic acids is as follows. Chlorogenic acids were quantified by filtering a coffee drink as a sample through a 0.45 μm membrane filter and injecting it into HPLC. The measurement conditions are as follows.

  The retention times of chlorogenic acids are 13.0 minutes, 13.8 minutes, 15.6 minutes, 16.5 minutes, 16.7 minutes, 17.4 minutes, 20.0 minutes, 20.6 minutes, 23.6. The chlorogenic acids were determined from the sum of the retention time peak areas.

(HPLC measurement conditions)
Column: TSK-gel ODS-80TsQA (4.6mmφx150mm, Tosoh Corporation)
-Mobile phase: A: Water: Trifluoroacetic acid = 1000: 0.5
B: Acetonitrile: trifluoroacetic acid = 1000: 0.5
・ Flow rate: 1.0ml / min
・ Column temperature: 40 ℃
・ Gradient condition;
Keep solution A at 100% until 5 minutes after the start of analysis.
Liquid B 10.0% from 5 to 10 minutes,
B liquid 15.6% from 10 to 16 minutes,
B liquid 17.0% from 16 to 26 minutes,
Liquid B 80% from 26 to 27 minutes,
Hold B 80% from 27 to 35 minutes,
Liquid B 0% from 35 to 36 minutes
・ Injection volume: 5.0μl
・ Detection wavelength: Chlorogenic acids (325nm)
・ Standard substance: Chlorogenic acid hemihydrate (Nacalai Tesque)
[Example 2] Masking effect of various amino acids on the bitter taste of chlorogenic acid Six solutions each containing 42 mg, 56 mg, 70 mg, 84 mg and 112 mg of chlorogenic acid were prepared per 100 ml of the aqueous solution.

0 mg, 21 mg, 42 mg, 83 mg, 167 mg, and 500 mg of L-ornithine hydrochloride were dissolved in each concentration of chlorogenic acid aqueous solution.
2. 0 mg, 21 mg, 42 mg, 83 mg, 167 mg, and 500 mg of L-ornithine hydrochloride were dissolved in sugar-free black coffee (commercial product A) (chlorogenic acid amount: 57 mg / 100 ml).

  3. A panel of three persons subjectively evaluated the bitter taste masking effect of L-ornithine hydrochloride on chlorogenic acid and coffee in an aqueous solution (◎ bitter taste is well masked; ○ bitter taste is masked; Δ bitter taste Feel a little; × feel bitterness strongly).

  4). D, L-alanine, L-valine and glycine were also evaluated in the same manner as in the above 1-3. D, L-alanine and glycine were also evaluated for bitterness masking effect on another sugar-free black coffee (commercially available product B) (chlorogenic acid amount: 46 mg / 100 ml).

The amount of chlorogenic acids was measured by the method described in Example 1.
The results are shown in the table below.

その結果、Ｌ−オルニチン塩酸塩、Ｄ，Ｌ−アラニン、Ｌ−バリン、グリシンのいずれのアミノ酸も、コーヒーの苦味およびクロロゲン酸の苦味を効果的にマスキングし、コーヒー飲料としての味も良好であることを見出した。特に、Ｄ，Ｌ−アラニンを添加するとほんのり甘く飲みやすくなったこと、グリシンを添加するとほんのりした弱い甘みがクロロゲン酸の苦味をマスキングしたことから、これら２つのアミノ酸は特にクロロゲン酸及びコーヒーの苦味マスキング剤として有効であることがわかった。

As a result, any amino acid of L-ornithine hydrochloride, D, L-alanine, L-valine and glycine effectively masks the bitter taste of coffee and the bitter taste of chlorogenic acid, and the taste as a coffee beverage is also good. I found out. In particular, the addition of D, L-alanine made it slightly sweeter and easier to drink, and the addition of glycine masked the bitter taste of chlorogenic acid due to the slightly weaker sweetness. It was found to be effective as an agent.

Claims (2)

The following components (A) and (B),
(A) Chlorogenic acid 20 mg / 100 ml to 150 mg / 100 ml,
(B) one or more amino acids selected from 500 mg / 100 ml or less of L-ornithine hydrochloride, 83 mg / 100 ml or less of D, L-alanine , and 500 mg / 100 ml or less of glycine;
A black coffee beverage in which the content ratio (weight ratio) of the component (A) to the component (B) is (B) / (A) is 1.0 or more.   The black coffee drink of Claim 1 in which amino acids other than L-ornithine hydrochloride, D, L-alanine, L-valine, and glycine are not added.