WO2002078470A1 - Boissons contenant de l'isoleucyl-tyrosine - Google Patents

Boissons contenant de l'isoleucyl-tyrosine Download PDF

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Publication number
WO2002078470A1
WO2002078470A1 PCT/JP2002/003096 JP0203096W WO02078470A1 WO 2002078470 A1 WO2002078470 A1 WO 2002078470A1 JP 0203096 W JP0203096 W JP 0203096W WO 02078470 A1 WO02078470 A1 WO 02078470A1
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WO
WIPO (PCT)
Prior art keywords
beverage
tyr
tyrosine
tea
blood pressure
Prior art date
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PCT/JP2002/003096
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English (en)
Japanese (ja)
Inventor
Taku Sato
Yuji Sakamoto
Original Assignee
Kirin Beer Kabushiki Kaisha
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Kirin Beer Kabushiki Kaisha filed Critical Kirin Beer Kabushiki Kaisha
Publication of WO2002078470A1 publication Critical patent/WO2002078470A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • A23F3/163—Liquid or semi-liquid tea extract preparations, e.g. gels, liquid extracts in solid capsules
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • the present invention relates to tea drinks and health drinks to which dipeptide iso- mouth isyl tyrosine (Ile-Tyr) or a substance containing iso-mouth isyl tyrosine (excluding the extract of fruit body of B. aeruginosa) is added. And other functional beverages.
  • Dipeptide iso- mouth isyl tyrosine Ile-Tyr
  • a substance containing iso-mouth isyl tyrosine excluding the extract of fruit body of B. aeruginosa
  • beverages containing dipeptides include hydrated colloidal polysaccharides (eg, xantham gum, pectin), saccharin salts, and diptide sweeteners (eg, aspartyl phenylalanine methyl ester).
  • colloidal polysaccharides eg, xantham gum, pectin
  • saccharin salts e.g., aspartyl phenylalanine methyl ester
  • Beverage composition JP-A-6-90721
  • strong cadibatide sweetener Hi-I-L-aspartame-L-L-phenylalanine methyl ester
  • sodium carboxymethylcellulose dextran, algin, gum arabic
  • a storage fluid containing a stabilizing fluid consisting of carrageenan, xanthan gum, guar gum, hydroxy-propylmethylcellulose, methylcellulose, pectin, locust bean gum, sodium alginate, propylene glycol alginate, ramamel and mixtures thereof.
  • Stability, aqueous sweetener suspension, etc. (W_ ⁇ 9 5Z 1 5 6 9 7, WO 9 5/1 7 1 0 4) are known.
  • isoleucyl thycin is a known dipeptide having angiotensin I converting enzyme (ACE) inhibitory activity.
  • ACE angiotensin I converting enzyme
  • isoleucyl thycin is obtained by ion-exchange or gel filtration of a hydrolyzate of the red alga Porphyi'a yezoensis. Reported to be included in the obtained fraction (J. Mar. Biotechnol. 1998 Aug; 6 (3): 163-7).
  • Japanese Unexamined Patent Publication No. 59-292221 discloses a health drink containing Maiyuga extract
  • Japanese Unexamined Patent Publication No. 7-25774 discloses a drink containing deer mushroom extract
  • Japanese Unexamined Patent Publication No. Hei 8-23. No. 938 discloses an agaricus extract beverage.
  • methods for efficiently extracting the active ingredient of mushrooms vary depending on the type of raw material mushroom, the physical properties of the active ingredient, the purpose of extraction, and the like. In particular, when processing into a beverage containing an extract, etc., it is necessary to effectively prevent the occurrence of floc and browning during storage, and the extract of mushrooms has a unique flavor, so it is used.
  • the present inventors have previously developed an artificial cultivation method (bacterial bed cultivation method) capable of stably obtaining a fruit body of Beech achitake mushroom with stable quality throughout the year (Japanese Patent Application Laid-Open No. 2000-3000). 0 666 publication).
  • SHR spontaneously hypertensive rats
  • Healthy rats did not show a blood pressure lowering effect, and found that they contained a blood pressure lowering effect component that has a blood pressure increase suppressing effect in long-term administration, and to prevent and prevent hypertension by adding a pharmacological composition containing such a component.
  • the present invention relates to a functional beverage (claim 1) comprising iso-isyltyrosine or a substance containing iso-isyl-tyrosine (excluding the extract of the fruit body of Prunus versicolor),
  • the functional beverage according to claim 1 wherein the content is 0.0000 to 5.0 wZV%, a tea beverage, a health drink, a fruit 3.
  • the functional beverage according to claim 1 or 2 wherein the beverage is a vegetable-based beverage, a carbonated beverage, a low-calorie beverage, or an alcoholic beverage.
  • FIG. 1 is a graph showing the ACE inhibitory activity of a Sepheadex G-25-treated fraction of a P. agaricus fruit body hot water extract.
  • FIG. 2 is a graph showing changes in systolic blood pressure 6 hours after the treatment of Sepheadex G-25 with a hot water extract of P. aeruginosa fruit body.
  • FIG. 3 is a graph showing an HPLC profile and an ACE inhibitory activity of a preparative HPLC-treated fraction of the fraction (B) treated with Sepheadex G-25 of a hot water extract of B. agaricus fruit body.
  • FIG. 4 shows the Sepheadex G-25-treated image of the hot water extract of the fruit body of B. agaricus
  • FIG. 2 is a view showing an elimination profile obtained by treating a fraction (C) with a preparative HP LC and an ACE inhibitory activity.
  • FIG. 5 is a graph showing changes in systolic blood pressure of Sephadex G-25 of the P. agaricus hot fruit extract and HPLC-treated fractions for preparative separation 6 hours later.
  • the functional beverage of the present invention may be any beverage to which isoroisyl tyrosine or a substance containing isoloisyl tyrosine (excluding the extract of the fruit body of B. aeruginosa) is added.
  • the term “beverage” means a beverage having an effect of preventing and / or improving hypertension such as a hypotensive effect.
  • Examples of the above-mentioned isoleucyl tyrosine include commercially available isoleucyl tyrosine products, recombinant isoloisyl tyrosine produced by genetic engineering, and iso-mouth isyl tyrosine separated and purified from iso-isyl tyrosine-containing substances such as fruit body of B.
  • the isoleucyl tyrosine-containing material is not particularly limited, as long as it contains isourisyl tyrosine, except for the extract of the fruit body of B. aeruginosa.
  • Examples include fractions obtained by subjecting a hydrolyzate of Porphyra yezoensis to ion exchange gel filtration.
  • the amount of the isoloisyl tyrosine or isoleucyl tyrosine-containing substance added to the beverage is not particularly limited.
  • the content of the isoleucyl tyrosine depends on the type of the beverage, 0.000 0 0 1 to 5.0 w // V%, preferably 0.0 0 0 5 to 0.5 wZv%, more preferably 0.05 to 0.5 w / v%
  • the amount is less than 0.000 w / v%, the effect of suppressing fading of the beverage and the effect of lowering blood pressure are not sufficient, and 5.0 w / v% Above this, it can be said that the discoloration inhibitory effect and blood pressure lowering effect of the beverage are sufficient, but economically disadvantageous.
  • the kind of the functional drink of the present invention is not particularly limited as long as it is a known drink, and tea drinks, health drinks, fruit / vegetable drinks, carbonated drinks, low calorie drinks, alcoholic drinks, etc. Can be specifically exemplified.
  • any of sugars, flavors, food additives and the like used in the general formulation of various drinks can be used. It may be used in combination with other functional materials such as ezogoki extract, lye extract, and tochu tea extract.
  • Tea-based beverages Iso-original isiltyrosine disoloisiruchiruchishin content, even when added to green tea, semi-fermented tea (oolong tea), fermented tea (black tea), etc., the original flavor and flavor of tea Without loss, the use of Chinese tea, especially golden katsura tea or tea leaves of the Jasmine plan, will suppress the fading and sedimentation.
  • the above tea leaves may be used alone, or in combination with tea leaves that can be expected to promote health, such as Tochu tea, Kakiha tea, Kumasa tea, Gyabaron tea, Corn tea, Hub tea, and Kikuhana tea. You may.
  • the method for producing the tea leaf extract is not particularly limited, but it is preferable to use 0.6% by weight or more of tea leaves.
  • the isomouth isyltyrosine and the isomouthlet siltycin-containing substance are usually added and blended into the tea leaf extract.
  • Health drinks can be manufactured by adding and blending isoloisyl tyrosine or isoloisyl cysteine with ordinarily or simultaneously with components normally used in the manufacture of health drinks. By adding isoleucyl tyrosine, the health drink is not affected by its flavor and flavor, and its discoloration and precipitation are suppressed.
  • Fruit and vegetable drinks are one kind of fruit juice such as orange, apple, grape, peach, strawberry, banana, lemon, and vegetable juice such as tomato, carrot, cabbage, and celery. Or a mixture of two or more, and then adding and blending a substance containing isoleucyl tyrosine diisoloisyl tyrosine. , And its discoloration and precipitation are suppressed.
  • Carbonated beverages can be produced by adding or blending isoleucyltyrosine or a substance containing isoleucyltyrosine at the same time or before or after the components usually used in the production of carbonated beverages. What is necessary is just to make it the carbonation pressure (0.1-0.4 Mpa) of the same level as ordinary carbonated drinks. Carbonated beverages generally have a sharp aftertaste, but the addition of isoleucyl tyrosine does not impair the sharp aftertaste, and the discoloration of a colored carbonated beverage is suppressed.
  • High-sugar beverages have the image of causing obesity, and in order to dispel that image, we started with high-intensity sweeteners such as stevia, aspartame, and sucralose, and erythritol and maltitol.
  • a low-strength liquid beverage made into a low-strength liquid using a low-calorie sweetener such as a sugar alcohol can be mixed with a compound containing iso-isyltyrosine-disoloisyl-tyrosine.
  • Addition and compounding of iso-or-isyl tyrosine or iso-or-isyl tyrosine-containing substances can be performed in any process, and if the low-strength liquid beverage is a colored low-strength liquid beverage, its discoloration is suppressed. be able to.
  • Alcoholic beverages are manufactured by adding and blending isoloisyl tyrosine and iso-mouth isyl tyrosine-containing substances to any process of alcoholic beverage production such as low-malt beer and whiskey liquids. However, it is preferable to produce such alcoholic beverages such as happoshu and whiskey and liqueurs, and then add and blend isoloisyl tyrosine disoloisyl tyrosine-containing material. Such an isoloisyl tyrosine-containing alcoholic beverage does not lose its original flavor and flavor, and its discoloration is suppressed.
  • the isoloisyl tyrosine-containing functional beverage of the present invention has excellent functions of maintaining the original color of the beverage without impairing the original flavor of the beverage, suppressing the formation of sediment, and having a blood pressure lowering effect. Although it is a beverage, it is also nutritionally useful. Isoleucine-tyrosine is an essential amino acid and is nutritionally essential. In particular, tyrosine is a precursor of neurotransmitter and essential for maintaining brain function. However, isoleucine monosaccharide was not suitable as a beverage material because of its bitter taste. In contrast, iso-isyltyrosine has no bitter taste and does not precipitate, which is a major problem in beverages.
  • Bunakogakus (380 g), dried beer lees (37.5 g), dried okara (37.5 g), tap water (545 g), total l OOO g, 1.2 kg PP (polypropylene)
  • the medium was prepared by filling the bag. Further, the bag was covered with a pyrene cap sandwiched with a filter and sterilized under pressure at 121 ° C for 50 minutes. After cooling the medium, inoculate a fungus of Buna mushroom, pre-culture in place at a temperature of 23 to 25 ° C and a humidity of 60 to 80% for 40 days, and then perform the medium culture process.
  • the temperature is 13 to 15 ° C
  • the primordial fungus was formed.
  • One portion of the bag where the primordium with a diameter of about 3 cm was observed was cut out, and the process was shifted to the post-culture step.
  • the culture of 13 to: L 5 ° (: 80 to 95% humidity, 200 lux illuminance) for 17 days will produce 1 strain of Buna hachitake fruit body.
  • the obtained fruit body of B. agarita was 232.5 g, and the total number of days required for cultivation was 87 days.
  • ACE inhibitory activity is described in the literature (Shunro Kawagishi, "Biochemical Experimental Methods 38, Research Methods for Biological Function Modulating Substances in Foods", Gakkai Shuppan Center, pp. 119-121, 199 ) Measured according to the method described.
  • Amino acid analysis The sample was dried, 1 mL of constant boiling hydrochloric acid (6N) was added, and the mixture was sealed under reduced pressure and hydrolyzed for 20 hours. After the hydrochloric acid was blown off, the sample was analyzed by a conventional method using an amino acid composition analyzer (Aminolaizer-124, SIC) for a hydrolysis sample.
  • Amino acid composition analyzer Aminolaizer-124, SIC
  • N-terminal amino acid sequence analysis Each sample was dropped on a polybutene-treated gas filter, dried, and analyzed by Sequencer-492 (manufactured by PE Biosystems).
  • MALD I-TO FMS analysis Each sample was mixed with 10 mg / mL of a-cyan-4-hydroxycinnamic acid on a sample plate, dried to dryness, and MALDI-TO FMS analyzer (Voyager_D ESTR, PE, Biosystems) according to a standard method.
  • Purification and identification of the following blood pressure lowering substances are basically based on the blood pressure lowering effect of SHR, but the ACE inhibitory activity, which is relatively easy to measure due to the mechanism of action of the blood pressure lowering substance, is also an auxiliary index.
  • the second fraction (B) which has the highest SHR blood pressure lowering activity, was collected, concentrated on a rotary evaporator and filtered, and then an 8% acetonitrile solution containing 0.1% TFA was added.
  • the eluate was supplied to preparative HPLC. 100 LL of each fraction (3.5 mL) collected was dried with a centrifugal concentrator, and the ACE inhibitory activity was measured. The results are shown in Figure 3. As shown in FIG. 3, several peaks indicating ACE inhibitory activity were obtained. Isocratic HPLC, which was used as an eluent for the peak showing the strongest activity, was renecked twice to obtain a single peak.
  • the third peak (C) of gel filtration which showed weak activity in in vivo, was concentrated and then subjected to the recrystallization of isocratic HP LC of 8% acetonitrile containing 0.1% TFA.
  • ACE inhibitory activity was measured for the fractions.
  • Fig. 4 shows the results. As shown in FIG. 4, three peaks showing ACE inhibitory activity were obtained, and amino acid sequence analysis was performed. From the two fractions, isoloisyl tributophan (Ile-Trp) and The presence of Rilto Livtojuan (Val-Trp) was estimated. The remaining fraction contains alanyl tributofan (Ala-Trp) and glycyltributophan.
  • Ile-Tyr The content of each peptide estimated from ACE activity was 5.4, 9.2, 1.6 ugZg dry powder for Ile-Tyr, Ile-Ti'p and Val- Val ⁇ ' ⁇ , respectively.
  • Ile-Tyr was scarcely detected in shiitake mushrooms and mushrooms, which are representative mushrooms and have reported hypotensive effects.
  • Ile-Tyr was identified as a substance having a blood pressure effect on SHR from the hot water extract of the fruit body of B. agaricus. At the same time, dipeptides containing five tryptophan were obtained, but when administered orally to SHR, the effect was not as low as Ile-Tyr.
  • dipeptides containing tryptophan which have stronger ACE inhibitory activity than Ile-Trp, Val-Trp, etc., are less effective at in vivo than Ile-Tyr.
  • Ile-Tyr is not detected in such species as Shiitake-maitake, and it is not present in any mushrooms, and the mechanism of generation of these Ile-Tyr is interesting. In general, it is thought that the protein is produced by the action of the protease on the precursor protein.
  • Ile-Tyr aqueous solution The above-mentioned Ile-Tyr sample solution (100 mg) was dissolved in tap water (100 mL). The lie-Tyr aqueous solution is colorless and transparent, tasteless and tasteless and odorless, and has no problem in drinking. Was.
  • He aqueous solution An aqueous Ile-Tyr aqueous solution in which 100 mg of the above-mentioned lie sample was dissolved in 100 mL of tap water was colorless and transparent, had a strong bitter taste, and was difficult to drink.
  • Tyr aqueous solution The Tyr aqueous solution obtained by dissolving 100 mg of the above Tyr sample in 100 mL of tap water was colorless and transparent, had a strong bitter taste, and was difficult to drink.
  • Reference sample aqueous solution The reference sample aqueous solution in which 50 g of the above Ile-Tyr-containing reference sample was dissolved in 100 mL of tap water was brown and transparent, had a tasteful taste, and was evaluated as preferable as a beverage. .
  • golden katsura tea without Ile_Tyr was found to precipitate by standing at 37 ° C for 1 week, and fading was observed 1 week after sunlight irradiation.
  • 1 g of the above Ile-Tyr standard 1 g of the above-mentioned lie standard or 1 g of the above-mentioned Tyr standard was added, and both lie-added golden katsura tea and Tyr-added golden katsura tea were light brown and transparent. However, it was bitter and not suitable for drinking.
  • the golden katsura tea with the lie-Tyr-containing material to which the above reference sample lg was added in place of the above 1 g of Ile-Tyr standard was not only light brown and transparent, had the original flavor, but also had a rich body The taste was increased, and the beverage was evaluated as favorable. No precipitation was observed even after one week at 37 ° C, and no fading was observed even after one week of irradiation with sunlight.
  • the lie-Tyr-containing health drink to which 1 g of the above-mentioned reference sample was added instead of the 1 g of the lie-Tyr preparation described above was not only light-brown and transparent and had an original flavor, but also a rich body and body.
  • the feeling and umami increased, and the evaluation that it was preferable as a beverage was obtained. No precipitation was observed even after standing at 37 for 1 week, and no fading was observed even after 1 week of irradiation with sunlight.
  • Example 2 blood pressure effect of lie-Tyr aqueous solution
  • the effect of the lie-Tyr aqueous solution on SHR blood pressure was examined.
  • An aqueous solution of Ile-Tyr prepared by dissolving 100 mg of lie-Tyr sample in 100 mL of tap water was orally administered to SHR (spontaneously hypertensive rat), and the blood pressure lowering activity was measured.
  • Distilled water, the lie aqueous solution and the Tyr aqueous solution were used as control groups.
  • the reference sample aqueous solution was used as a reference section.
  • the test group, the control group, and the reference group were each performed with 6 animals per group, and the blood pressure lowering activity was measured as follows.
  • the reference sample aqueous solution was orally administered to the stomach by a sonde, and kept at 40 ° C for 10 minutes at regular intervals, and the systolic blood pressure was measured using a non-invasive blood pressure measuring device (“BP-98 )).
  • BP-98 non-invasive blood pressure measuring device
  • the functional flavor which does not impair the original flavor of a drink, maintains the original color tone of a drink, suppresses precipitation during storage, and has a blood pressure lowering effect can be provided.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Mycology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Dispersion Chemistry (AREA)
  • Non-Alcoholic Beverages (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Tea And Coffee (AREA)

Abstract

L'invention concerne des boissons fonctionnelles ayant pour effet d'abaisser la pression artérielle et présentant une sédimentation maîtrisée lors de leur stockage tout en conservant leur couleur inhérente et sans souffrir d'une altération quelconque de leur goût inhérent. Ces boissons fonctionnelles sont obtenues par addition d'isoleucyl-tyrosine (Ile-Tyr) ou d'une substance contenant de l'isoleucyl-tyrosine à des boissons à base de thé, des boissons santé, etc. La teneur en isoleucyl-tyrosine de ces boissons est comprise, de préférence, dans la plage 0,00001-5,0 % en poids/volume.
PCT/JP2002/003096 2001-03-30 2002-03-28 Boissons contenant de l'isoleucyl-tyrosine WO2002078470A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001100000A JP2002291452A (ja) 2001-03-30 2001-03-30 イソロイシルチロシン含有飲料
JP2001-100000 2001-03-30

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WO2002078470A1 true WO2002078470A1 (fr) 2002-10-10

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WO (1) WO2002078470A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005333815A (ja) * 2004-05-24 2005-12-08 Meiji Milk Prod Co Ltd 茶抽出液の沈澱及び／又はオリ発生抑制剤
JP5963093B2 (ja) * 2014-02-18 2016-08-03 株式会社 レオロジー機能食品研究所 Ｔｒｐ含有ペプチドの製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10175997A (ja) * 1996-12-12 1998-06-30 Shirako:Kk 海苔から得られるペプチド混合物
JP2000300066A (ja) * 1999-04-19 2000-10-31 Kirin Brewery Co Ltd ブナハリタケの栽培方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10175997A (ja) * 1996-12-12 1998-06-30 Shirako:Kk 海苔から得られるペプチド混合物
JP2000300066A (ja) * 1999-04-19 2000-10-31 Kirin Brewery Co Ltd ブナハリタケの栽培方法

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