JP7706688B2 - Composition containing an aqueous extract of ripe Japanese pepper - Google Patents

Description

The present invention relates to a composition containing an aqueous extract of ripe Japanese pepper, and in particular to a salty taste sensitizing composition, a composition for improving the persistence of the taste of food and beverages in the mouth, and food and beverages, all of which contain an aqueous extract of ripe Japanese pepper.

In response to the growing health consciousness, it is desired to reduce the intake of salt, which can be a cause of lifestyle-related diseases. On the other hand, foods with low salt equivalents are perceived as lacking in flavor, so various researches are being conducted to enhance their saltiness. For example, Patent Document 1 describes a saltiness enhancer to be used before meals, which contains crushed Japanese pepper and a base material for leaving the spicy components of the crushed pepper in the mouth for about several minutes before a meal, and contains a specified amount of sanshool. Patent Document 2 describes a saltiness enhancer for a specified food or drink, which contains Japanese pepper extract and phthalides as active ingredients. And Patent Document 3 describes a saltiness sensitizing composition containing Japanese pepper extract and a sulfide compound having an alkyl group.

Patent No. 5625089 Patent No. 5733737 JP 2020-142 A

Conventionally, it was thought that sanshools contained in pepper extract were one of the active ingredients that enhance saltiness or sensitize saltiness, but other active ingredients had not been thoroughly studied. Therefore, the present invention aims to provide a composition that contains a new active ingredient and is suitable for sensitizing saltiness.

The present inventors have conducted extensive research to solve the above-mentioned problems, and have found that the aqueous extract of fully ripe pepper with red skin, not the green-skinned pepper (unripe pepper) that is commonly used as a food ingredient, contains an active ingredient that has a salty taste sensitizing effect other than sanshools, and that this active ingredient also has the effect of improving the taste persistence in the mouth of food whose taste intensity is reduced due to a decrease in salt concentration, and have completed the present invention. That is, the present invention provides the following salty taste sensitizing composition, the composition for improving the taste persistence in the mouth of food and drink, and food and drink.
[1] A salty taste sensitizing composition comprising an aqueous extract of ripe Japanese pepper.
[2] A composition for improving the persistence of the taste of food or beverage in the mouth, comprising an aqueous extract of ripe Japanese pepper.
[3] The composition described in [2] above, wherein the food or beverage is a reduced-salt food or beverage.
[4] The composition according to any one of [1] to [3], wherein the aqueous extract comprises a water extract and/or an alcohol extract of ripe pepper.
[5] The composition according to any one of [1] to [4] above, wherein the aqueous extract contains a compound represented by the formula C ₁₀ H ₁₈ O ₂ or C ₁₀ H ₁₆ O ₂ .
[6] A food or beverage containing an aqueous extract of ripe Japanese pepper.
[7] The food or beverage described in [6] above, which is a reduced-salt food.
[8] The food or beverage described in [6] or [7], wherein the aqueous extract comprises a water extract and/or an alcohol extract of ripe Japanese pepper.
[9] The food or drink according to any one of [6] to [8] above, wherein the extract contains a compound represented by the composition formula C ₁₀ H ₁₈ O ₂ or C ₁₀ H ₁₆ O ₂ .

According to the present invention, by using an aqueous extract of ripe Japanese pepper, it is possible to enhance the saltiness of food and drink, and also improve the persistence of the taste of the food and drink in the mouth. Therefore, for example, reduced-salt foods can be eaten more deliciously.

The results of evaluation using the visual analog scale (VAS) method are shown. The results of evaluation by the time intensity measurement method (TI method) are shown. 1 shows a chromatogram of an aqueous extract of ripe Japanese pepper.

The present invention will now be described in further detail.
The present invention relates to a composition for saltiness sensitization comprising an aqueous extract of ripe Japanese pepper. The term "saltiness sensitization" as used herein means that the saltiness felt when a food or drink is placed in the oral cavity becomes stronger, even though the salt content of the food or drink does not change. In other words, when the composition of the present invention is ingested before or at the same time as placing the food or drink in the oral cavity of a subject, the saltiness of the food or drink can be felt stronger.

The present invention also relates to a composition for improving the persistence of the taste of food and beverages in the mouth, comprising an aqueous extract of ripe Japanese pepper. The composition of the present invention increases the intensity of the flavor of food and beverages, allowing the flavor to last longer in the mouth. For example, it is believed that the intensity of the flavor felt first when the food or beverage is placed in the mouth (initial taste), followed by the flavor felt next (intermediate taste), and the flavor that remains in the mouth thereafter (aftertaste) will be increased, resulting in a longer duration in the mouth overall. When the composition of the present invention is ingested before or simultaneously with placing the target food or beverage in the oral cavity, the flavor of the food or beverage can be enjoyed for a longer period of time.

There are no particular limitations on the food and drink whose salty taste is sensitized or whose taste persistence in the mouth is improved by the composition of the present invention, but if the food and drink is a reduced-salt food, the salty taste sensitizing effect or taste persistence improving effect of the composition can be felt more strongly. Note that "reduced-salt food" as described in this specification refers to food whose salt concentration is lower than that of general forms that are normally distributed. The salt concentration of the reduced-salt food is not particularly limited, but may be, for example, about 25 to about 70% lower by mass in terms of salt equivalent than that of general forms that are normally distributed.

The term "fully ripe pepper" as used herein refers to the fruit of a plant of the genus Zanthoxylum in the family Rutaceae that has ripened on the tree until the skin is reddish in color, and is sometimes called red pepper. As the plant of the genus Zanthoxylum in the family Rutaceae, any plant commonly used in the art can be used without any particular limitation, and examples thereof include Zanthoxylum piperitum DC, Zanthoxylum niger DC. forma inerme Makino, and Zanthoxylum niger DC. forma brevispinosum Makino, ...

The aqueous extract can be prepared by extracting the fully ripe pepper with an aqueous solvent, either as is or after crushing, grinding, drying, etc. The extraction method is not particularly limited as long as the active ingredients described below are extracted, but for example, solvent extraction, steam distillation extraction, and supercritical or subcritical extraction may be used. The aqueous solvent is not particularly limited, but for example, water, alcohols such as ethanol and methanol, etc. may be used, or two or more of these may be mixed and used. In one embodiment, the aqueous extract contains a water extract (particularly a hot water extract) of fully ripe pepper and/or an alcohol extract (particularly an ethanol extract) of fully ripe pepper.

The content of the aqueous extract is not particularly limited as long as it exerts the salty taste sensitizing effect or the taste duration improving effect, but may be, for example, an amount equivalent to a concentration of hydroxy α sanshool present at about 3.0×10 ⁻⁵ to about 100 mass ppm (hereinafter simply referred to as “ppm”) relative to the total mass of the composition of the present invention, and preferably an amount equivalent to a concentration of hydroxy α sanshool present at about 0.01 to about 10 ppm. When the aqueous extract is contained in such an amount, the salty taste sensitizing effect and the taste duration improving effect are more satisfactorily exerted, and the influence on the flavor of food and drink taken simultaneously with or successively with the composition of the present invention can be minimized. Note that hydroxy α sanshool is not an active ingredient of the present invention, but is merely described as a guideline for the content of the aqueous extract. Even if the aqueous extract is fractionated and an aqueous solution of a fraction not containing hydroxy α sanshool is used as the aqueous extract, the content can be specified as the hydroxy α sanshool equivalent amount. For example, when the aqueous extract is fractionated into several fractions by medium pressure preparative chromatography for sensory evaluation, and then an aqueous solution of another fraction is prepared by adding water in the same ratio as that for preparing an aqueous solution of a fraction containing hydroxy α-sanshool to have a concentration of 1 ppm, the content of the aqueous extract in the aqueous solution is expressed as 1 ppm in terms of hydroxy α-sanshool equivalent.

（この表は、移動相のメタノール濃度を、０～８分の間では５０％に維持し、８～１５分の間では５０％から７５％に徐々に上昇させ、１５～３５分の間では７５％に維持し、３５～３５．５分の間では７５％から９５％に上昇させ、３５．５～４５分の間では９５％に維持し、４５～４５．５分の間では９５％から５０％に低下させ、４５．５分～６０分の間では５０％に維持することを示している。以降の移動相条件の表も、同様に解釈される。） In one embodiment, the aqueous extract of ripe pepper contains _a compound represented by _the formula _C10H18O2 (compound A) or _C10H16O2 (compound B ₎ . Without being bound by any particular theory, these compounds are contained in relatively small amounts in the aqueous extract of unripe pepper, and are contained in considerable amounts in the fraction _that exerts the salty taste sensitizing effect and the taste sustaining effect in the mouth that are specific to the aqueous extract of ripe pepper, and therefore compounds A and B may be the active ingredients responsible for these effects. The retention times of compounds A and B when analyzed by liquid chromatography mass spectrometry (LC-MS) under the following conditions are 20.96 minutes and 20.86 minutes, respectively.
Equipment used: Ultimate 3000 (Thermo Scientific), Orbitrap velos pro (Thermo Scientific)
Column: ODS column (Unison-UK-C18, manufactured by Imtakt)
Size: 4.6 x 250 mm
Particle size: 3μm
Mobile phase: methanol/0.1% formic acid/distilled water (see Table 1)
Flow rate: 0.4mL/min Temperature: 30℃
Injection volume: 3μL
(Orbitrap conditions)
Ionization mode: positive Heater temperature: 200°C
Spray voltage: 3.5 kV
Capillary temperature: 300°C
Sheath gas: 50 L/h
Auxiliary gas: 15L/h
Collision energy: 35 eV

(This table shows that the methanol concentration of the mobile phase is maintained at 50% between 0 and 8 minutes, gradually increased from 50% to 75% between 8 and 15 minutes, maintained at 75% between 15 and 35 minutes, increased from 75% to 95% between 35 and 35.5 minutes, maintained at 95% between 35.5 and 45 minutes, decreased from 95% to 50% between 45 and 45.5 minutes, and maintained at 50% between 45.5 and 60 minutes. The following tables of mobile phase conditions are interpreted in the same way.)

The characteristics of Compound A and Compound B as determined from the results of LC-MS and the like are summarized in Table 2 below.

The form of the composition of the present invention is not particularly limited as long as it is edible, and may be, for example, a liquid, jelly, paste, powder, granules, block, or the like. Specifically, the composition may be in the form of a beverage such as tea, jelly, candy, furikake, miso soup, seasoning, or the like. The composition may be consumed as is, or may be incorporated into food or beverage for which a stronger saltiness is desired. The composition may also be incorporated into other food or beverage to be consumed together with the food or beverage for which a stronger saltiness is desired, and these may be consumed alternately.

In another aspect, the present invention also relates to a food or beverage containing an aqueous extract of ripe Japanese pepper. The food or beverage of the present invention contains the aqueous extract of ripe Japanese pepper, and therefore, due to its saltiness sensitizing effect or taste persistence improving effect, even if the food has a low salt concentration, the taste intensity is increased and the taste persistence in the mouth is improved, making it possible to eat it deliciously.

The salty taste sensitizing composition, the composition for improving the duration of the taste of a food or drink in the mouth, and the food or drink of the present invention may further contain any food ingredient or any additive commonly used in the art, or may further contain other additives effective for salty taste sensitization or improving the duration of taste, as long as the purpose of the present invention is not impaired.

The present invention will be described in detail below with reference to examples, but the scope of the present invention is not limited to these examples.

[Test Example 1]
10g of raw (frozen) berries of ripe grape pepper (red) and unripe grape pepper (green) were prepared, and 100g of each hot water extract was prepared by a conventional method. The concentration of hydroxy α-sanshoal in each hot water extract was measured by high performance liquid chromatography (HPLC), and the concentration was 34ppm in the hot water extract of ripe grape pepper and 18ppm in the hot water extract of unripe grape pepper. These hot water extracts were added to oolong tea so that the final concentration of hydroxy α-sanshoal was 1.5ppm, and the taste enhancement effect of this oolong tea was evaluated by nine panelists. That is, each panelist took one mouthful (about 20 mL) of oolong tea containing either of the hot water extracts or oolong tea not containing either of the extracts (control group), then took bonito soup stock with a salt content of 0.4%, and evaluated the "initial taste", "thickness of taste", "aftertaste extension", "strength of taste", "absence of wateriness", "satisfaction", and "taste" by visual analog scale (VAS) using sensory evaluation software (FIZZ, ver. 2.51 c 02, BIOSSYSTEMS). In addition, the "strength of taste" was also evaluated by the time intensity method (TI method) using the same sensory evaluation software.

In the VAS method, a horizontal line closed at both ends by short vertical lines was displayed on a computer screen, and the standards for both ends were set as shown in Table 3 below, and the panelists wrote their evaluations as vertical lines on the line. The distance from the left end to the vertical line written by the panelists was then measured, and the value obtained by dividing the distance by the total length of the line was used to obtain a score, and a Dunnett's test was performed.

The results of the evaluation using the VAS method and the TI method are shown in Figures 1 and 2, respectively. As shown in Figure 1, the bonito stock with a salt content of 0.4% was tasteless and watery due to its low salt concentration, but the scores of each evaluation item increased when oolong tea containing a hot water extract of unripe Japanese pepper was consumed beforehand. Furthermore, when oolong tea containing a hot water extract of fully ripe Japanese pepper was consumed beforehand, the scores were even higher, except for the item of initial taste. In particular, the improvement of "depth of flavor" and "lengthening of aftertaste" are issues that must be resolved in order to ingest foods with low salt concentrations deliciously, and as a result of these improvements, "strength of flavor," "absence of wateriness," "satisfaction," and "taste" also improved, indicating that aqueous extracts such as hot water extract of fully ripe Japanese pepper are suitable for enhancing the saltiness of reduced-salt foods.

Furthermore, as shown in Figure 2, compared with the case of prior ingestion of control oolong tea (solid line) not containing hot water extract of Japanese pepper, prior ingestion of oolong tea containing hot water extract of unripe Japanese pepper (dashed line) increased the intensity of the flavor and prolonged the duration of the flavor in the mouth, whereas prior ingestion of oolong tea containing hot water extract of fully ripe Japanese pepper (dash-dotted line) prolonged the duration of the flavor in the mouth even further. In other words, aqueous extracts such as hot water extract of fully ripe Japanese pepper not only increase sensitivity to taste but also improve the duration of the flavor in the mouth, making them even more suitable for adjusting the flavor of reduced-salt foods.

[Test Example 2]
Ripe grape pepper berries (dried material) were prepared, and 100 parts by mass of 40% ethanol extract (concentration of hydroxy α-sanshoal: 260 ppm) was prepared from 5 parts by mass of the berries by a conventional method. Fractions 1 to 5 (Fr. 1 to Fr. 5 in Figure 3) were separated from this ethanol extract by medium pressure preparative chromatography for sensory evaluation under the following conditions.
Column: ODS column (ODS-SM-50C, Yamazen Corporation)
Mobile phase: water/methanol (see Table 4)
Flow rate: 30mL/min Temperature: 30℃
Detection wavelength: 270 nm

HPLC analysis using a standard substance revealed that fraction 3 contained hydroxy α-sanshoul and fraction 4 contained α-sanshoul. The solvent of each fraction was evaporated to dryness using an evaporator, and the amount of the dried matter recovered was measured (Table 5). Then, the dried matter of fraction 3 was considered to be entirely hydroxy α-sanshoul, and 1 mg of it was dissolved in 1 mL of 60% ethanol (1000 ppm), and this was diluted with water to a final concentration of 1.0 ppm. The same procedure was performed for the other fractions, and each aqueous solution was prepared so that the final dilution ratio was the same as that of fraction 3, that is, the ratio of the recovered amount of each dried matter was the same as the ratio of the dissolved amount in the aqueous solution.

After taking a mouthful (about 20 mL) of each aqueous solution of the fraction, four panelists drank miso soup with a salt content of 0.7% and evaluated which of the initial taste, middle taste, and aftertaste of the miso soup they felt was strongest. The results are shown in Table 6.

Many panelists felt that the miso soup had a stronger initial taste when they drank it after ingesting fraction 3, fraction 4, or fraction 5, but many panelists felt that the miso soup had a stronger aftertaste when they drank it after ingesting fraction 2. Hydroxy α-sanshool contained in fraction 3 and α-sanshool contained in fraction 4 can also be contained in aqueous extracts of unripe sansho, but are not contained in fraction 2. Therefore, the components that have the effects unique to ripe sansho, which increase the intensity of the flavor and improve the persistence of the flavor in the mouth, may be contained in fraction 2.

[Test Example 3]
Ripe grape pepper fruit and unripe grape pepper fruit (dried product) were prepared, and 100 parts by mass of 40% ethanol extract was prepared from 5 parts by mass of fruit by a conventional method. An aqueous solution of fraction 2 of medium pressure preparative chromatography for sensory evaluation was prepared in the same manner as in Test Example 2, and its concentration was adjusted to 1.0 ppm (0.2 ppm based on the dried product of fraction 2) in terms of hydroxy α-sanshool equivalent (Table 7).

After taking a mouthful (approximately 20 mL) of each solution, three panelists drank miso soup with a salt content of 0.7% and rated which of the miso soup's initial taste, middle taste, and aftertaste they felt was strongest. As a result, all three panelists answered that Fraction 2 of unripe pepper did not affect the taste of the miso soup, but that taking Fraction 2 of fully ripe pepper enhanced the saltiness of the miso soup and gave it a stronger aftertaste. Therefore, the effect of enhancing the saltiness and prolonging the taste in the mouth is unique to fully ripe pepper.

[Test Example 4]
Fraction 2 derived from a 40% ethanol extract of fully ripe Japanese pepper was further divided into five fractions (Fr. 2-1 to Fr. 2-5). The effects on the taste of miso soup were investigated in the same manner as in Test Example 3. As a result, all three panelists answered that the second and third fractions (Fr. 2-2 and Fr. 2-3) had the effect of enhancing the salty taste and prolonging the taste in the mouth, but that the other fractions had no such effect.

[Test Example 5]
Fraction 2 derived from 40% ethanol extract of ripe and unripe grape pepper prepared in the same manner as in Test Example 3 was analyzed by LC-MS, and the results of both analyses were compared. It was found that two compounds with retention times of 20 to 22 minutes when analyzed by high performance liquid chromatography under the following conditions were specifically contained in ripe pepper, and that the absolute amounts of these compounds were also large.
Equipment used: Ultimate 3000 (Thermo Scientific), Orbitrap velos pro (Thermo Scientific)
Column: ODS column (Unison-UK-C18, manufactured by Imtakt)
Size: 4.6 x 250 mm
Particle size: 3μm
Mobile phase: methanol/0.1% formic acid/distilled water (see Table 8)
Flow rate: 0.4mL/min Temperature: 30℃
Injection volume: 3μL
(Orbitrap conditions)
Ionization mode: positive Heater temperature: 200°C
Spray voltage: 3.5 kV
Capillary temperature: 300°C
Sheath gas: 50 L/h
Auxiliary gas: 15L/h
Collision energy: 35 eV

From the results of LC-MS, it was _found that the compound with a retention time of 20.96 minutes (compound A) had a molecular weight of 170.13 and a composition formula _{of C10H18O2} , and from the appearance of the fragmentation pattern, it was found to have one or more OH _groups . The other compound with a retention time of 20.86 minutes (compound B) had a molecular weight of 168.11 and a composition formula of _{C10H16O2 .} Furthermore, since neither compound showed characteristic UV absorption, they did not have conjugated double bonds or the like.

When Fr. 2-1 to Fr. 2-5 fractions obtained in Test Example 4 were analyzed by LC-MS, Compound A and Compound B were found to be contained in Fr. 2-2 and Fr. 2-3, but not in other fractions. Therefore, Compound A and Compound B are considered to contribute to the salty taste enhancement or sensitization effect of the aqueous extract of ripe Japanese pepper and the effect of improving the persistence of the taste in the mouth.

From the above, it was found that the use of an aqueous extract of ripe Japanese pepper makes it possible to enhance the saltiness of food and drink, and also improves the persistence of the taste of the food and drink in the mouth. Therefore, for example, reduced-salt foods can be eaten more deliciously.

Claims (8)

A composition for increasing the intensity of flavor of a food or drink, comprising an aqueous extract of ripe Japanese pepper ,
The aqueous extract is a 40% ethanol extract of ripe Japanese pepper under the following conditions (preparative chromatography conditions).
Column: ODS column (ODS-SM-50C, Yamazen Corporation)
Mobile phase: water/methanol Flow rate: 30 mL/min Temperature: 30° C.
Detection wavelength: 270 nm

The composition is a fraction separated from between a peak having a retention time of about 10 minutes and a peak having a retention time of about 40 minutes in a chromatogram obtained by subjecting the composition to preparative chromatography. A salty taste sensitizing composition comprising an aqueous extract of ripe Japanese pepper ,
The aqueous extract is a 40% ethanol extract of ripe Japanese pepper under the following conditions (preparative chromatography conditions).
Column: ODS column (ODS-SM-50C, Yamazen Corporation)
Mobile phase: water/methanol Flow rate: 30 mL/min Temperature: 30° C.
Detection wavelength: 270 nm

The composition is a fraction separated from between a peak having a retention time of about 10 minutes and a peak having a retention time of about 40 minutes in a chromatogram obtained by subjecting the composition to preparative chromatography. A composition for improving the persistence of taste of a food or drink in the mouth, comprising an aqueous extract of ripe Japanese pepper ,
The aqueous extract is a 40% ethanol extract of ripe Japanese pepper under the following conditions (preparative chromatography conditions).
Column: ODS column (ODS-SM-50C, Yamazen Corporation)
Mobile phase: water/methanol Flow rate: 30 mL/min Temperature: 30° C.
Detection wavelength: 270 nm

The composition is a fraction separated from between a peak having a retention time of about 10 minutes and a peak having a retention time of about 40 minutes in a chromatogram obtained by subjecting the composition to preparative chromatography. The composition according to claim 1 or 3, wherein the food or drink is a reduced-salt food or drink. The composition of any one of claims 1 to 4, wherein the aqueous extract comprises a compound having the formula C ₁₀ H ₁₈ O ₂ or C ₁₀ H ₁₆ O ₂ . A food or drink comprising an aqueous extract of ripe Japanese pepper added thereto,
The aqueous extract is a 40% ethanol extract of ripe Japanese pepper under the following conditions (preparative chromatography conditions).
Column: ODS column (ODS-SM-50C, Yamazen Corporation)
Mobile phase: water/methanol Flow rate: 30 mL/min Temperature: 30° C.
Detection wavelength: 270 nm

The food or drink described above is a fraction separated from between a peak at a retention time of approximately 10 minutes and a peak at a retention time of approximately 40 minutes in a chromatogram when the food or drink is subjected to preparative chromatography. The food or drink according to claim 6, which is a reduced-salt food. _8. The food or drink according to claim 6 or ₇ , wherein the aqueous extract contains a compound represented by the _{formula C10H18O2} or _{C10H16O2 .}

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