US20120283270A1 - Extracts and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-, (3s,6s)- - Google Patents

Extracts and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-, (3s,6s)- Download PDF

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US20120283270A1
US20120283270A1 US13/516,488 US201013516488A US2012283270A1 US 20120283270 A1 US20120283270 A1 US 20120283270A1 US 201013516488 A US201013516488 A US 201013516488A US 2012283270 A1 US2012283270 A1 US 2012283270A1
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Prior art keywords
meat
extract
compound
liquid
beverages
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Hideki Matsubayashi
Kenji Yamamoto
Hiroshi Watanabe
Lee Kian Hong
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PRICE RANDY RAY
Suntory Holdings Ltd
Suntory Beverage and Food Asia Pte Ltd
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Suntory Holdings Ltd
Cerebos Pacific Ltd
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Assigned to PRICE, RANDY RAY reassignment PRICE, RANDY RAY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PRICE, RANDY RAY, TAGGE, RONALD F.
Assigned to CEREBOS PACIFIC LIMITED, SUNTORY HOLDINGS LIMITED reassignment CEREBOS PACIFIC LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HONG, LEE KIAN, MATSUBAYASHI, HIDEKI, YAMAMOTO, KENJI, WATANABE, HIROSHI
Publication of US20120283270A1 publication Critical patent/US20120283270A1/en
Abandoned legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • 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
    • A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
    • A23L13/30—Meat extracts
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/66—Proteins
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • 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 foods and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-,(3S,6S)—, and more particularly relates to extracts and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-,(3S,6S)— at a high concentration, wherein the pH is 5 or more.
  • Dipeptides composed of two amino acids attached to each other has received attention as a functional substance.
  • Dipeptides can be designed to have additional physical properties and/or new functions, which cannot be seen in single amino acids, and hence they are expected to be applicable to a wider range than that of amino acids.
  • the inventors of the present invention have found that a 2,5-diketopiperazine derivative, i.e., 2,5-piperazinedione,3,6-bis(phenylmethyl)-,(3S,6S)— (CA Registry Number: 2862-51-3) (hereinafter referred to as “compound A”) has an improving effect on learning motivation (the co-filed patent application: Japanese Patent Application No. 2009-296164).
  • Products known to contain compound A include chicken extracts in liquid form which are obtained by decocting meat of livestock, as well as chicken consomme and the like in solid form.
  • compound A is hardly soluble in water and hence cannot be simply added as such when attempting to incorporate compound A, which is a useful substance with an improving effect on learning motivation, into beverages at a high concentration and in an easy-to-ingest form.
  • the present invention aims to provide an extract or beverage containing compound A, which is a useful substance with an improving effect on learning motivation, in an easy-to-ingest form and at a high concentration.
  • extracts and beverages which not only contain compound A at a high concentration but also have low Bx values and which are good in flavor and feeling on the tongue and further have a good appearance. This success led to the completion of the present invention.
  • the present invention is directed to [1] to [15] shown below.
  • the extract according to [3] above, wherein the naturally occurring product is meat of livestock or poultry, fish meat, or shellfish meat.
  • the extract according to [3] or [4] above, wherein the naturally occurring product is chicken meat.
  • a dried extract obtainable by drying the extract according to any one of [1] to [5] above.
  • a capsule or tablet encapsulating the extract according to any one of [1] to [5] above or the dried extract according to [6] above.
  • a beverage obtainable by addition of the extract according to any one of [1] to [5] above.
  • the beverage according to [8] or [9] above which contains compound A in an amount of 60 ⁇ g/100 g or more.
  • a packaged beverage wherein the beverage according to any one of [8] to [10] above is packed in a container.
  • a process for producing the extract according to [1] above which comprises:
  • the present invention provides extracts and beverages, in which compound A having an improving effect on learning motivation and being highly safe without side effects can be contained at a high content with Bx values remaining low.
  • the extracts of the present invention can be added to beverages and so on without impairing the taste inherent to foods and beverages.
  • the extracts or beverages of the present invention, as well as foods and beverages comprising the same can be ingested continuously over a long period of time as foods and beverages useful for improvement of learning motivation.
  • FIG. 1 shows the test results of whether the ingestion of a test sample reduces the time required for mice to find out an escape platform when repeating the test.
  • FIG. 2 shows the test results of whether the ingestion of a test sample reduces the time required for mice to find out an escape platform when repeating the test.
  • FIG. 3 shows the quantification results of compound A in extracts obtained with various starting materials.
  • the extract of the present invention contains compound A, which is a useful substance with an improving effect on learning motivation, at a high content and in an easy-to-ingest form. More specifically, it is an extract which contains compound A at a high concentration and whose ratio between the content of compound A (unit: ⁇ g/100 g) and Brix (Bx) is 6 ( ⁇ g/100 g)/Bx or more.
  • compound A is a useful substance with an improving effect on learning motivation, it is more desirable to have a higher content in the extract. More specifically, the content is preferably 60 ⁇ g/100 g or more; and more preferably 75 ⁇ g/100 g or more.
  • an extract with a high Brix value means that various substances (e.g., bitter components) originating from starting materials are contained at high concentrations, and such an extract is in itself unsuitable as a beverage and also affects the flavor or feeling on the tongue so greatly that it is unsuitable for use in beverages. Thus, a lower Brix value is more desirable.
  • Bx used herein can be determined with a commercially available Bx meter.
  • an extract being rich in compound A, which is a useful substance, and having a low Brix value, i.e., an extract whose ratio between the content of compound A (unit: ⁇ g/100 g) and Brix (Bx) is high. More specifically, the ratio between the content of compound A (unit: ⁇ g/100 g) and Brix (Bx) is preferably 6 ( ⁇ g/100 g)/Bx or more, and more preferably 10 ( ⁇ g/100 g)/Bx or more.
  • the concentration of compound A can be quantified in various manners, for example, by high performance liquid chromatography (HPLC).
  • HPLC high performance liquid chromatography
  • the extract of the present invention is advantageous in that it can be incorporated in small amounts into beverages and allows more latitude in beverage design because of its relatively low Bx value although it contains compound A at a high content. As a result, it is possible to prepare beverages which are excellent in appearance (causing no sediment or turbidity) and whose flavor is not impaired.
  • the extract of the present invention preferably has a pH of 5 or more such that it leaves no sediment, e.g., when added to a liquid of neutral pH.
  • the pH is preferably 10 or less, and more preferably 8 or less for direct ingestion.
  • extract used herein is intended to mean a liquid extract, which may be ingested as such or may be added to foods and beverages.
  • the extract can be easily converted into a powder form through a step of lyophilization or freeze-drying, etc.
  • the resulting extract powder is water-soluble and can be easily dissolved in a liquid of pH 5 or more (e.g., water) before ingestion.
  • conversion into a powder form facilitates addition of the extract to various foods and beverages, and allows easy use of the extract.
  • soft capsules or tablets encapsulate the extract of the present invention, or an extract powder or granule thereof.
  • foods and beverages into which the extract or extract powder is incorporated there is no limitation on the type or form of foods and beverages into which the extract or extract powder is incorporated.
  • they can be provided in the form of health foods in a tablet form (e.g., tablets and capsules), solid foods including yogurt, processed foods, desserts and sweets (e.g., gum, candy, jelly), liquid beverages including coffee, oolong tea, tea, soft drinks and drinkable preparations.
  • a tablet form e.g., tablets and capsules
  • solid foods including yogurt, processed foods, desserts and sweets (e.g., gum, candy, jelly)
  • liquid beverages including coffee, oolong tea, tea, soft drinks and drinkable preparations.
  • pet foods and animal feeds are also included.
  • the present invention is directed to a beverage which contains compound A and whose ratio of compound A content/Bx is 6 ( ⁇ g/100 g)/Bx or more, and more particularly a beverage which contains compound A in an amount of 60 ⁇ g/100 g or more.
  • the beverage of the present invention is good in flavor and feeling on the tongue and further has a good appearance.
  • the beverage of the present invention also has an improving effect on learning motivation and can be ingested continuously over a long period of time.
  • the pH of the beverage of the present invention is not limited in any way, but it preferably ranges from 5 to 10.
  • the beverage of the present invention can be provided in the form of a packaged beverage, as in the case of conventional beverages.
  • the present invention is directed to an extract or beverage containing compound A, in which the concentration of compound A can be increased even at a low Bx value.
  • an extract or beverage can be prepared, for example, by the production process shown below:
  • a preferred starting material used in the above pretreatment step (1) is a naturally occurring product from which compound A, a useful component, can be efficiently obtained, particularly meat of livestock or poultry, fish meat, or shellfish meat.
  • meat of livestock or poultry include meat of livestock, i.e., cattle, pig, horse, sheep or goat, meat of non-livestock animals such as wild boar or deer, meat of poultry, i.e., chicken, turkey, quail, domestic duck or crossbred duck, as well as meat of non-poultry wild birds such as wild duck, pheasant, sparrow or thrush.
  • meat of poultry i.e., chicken, turkey, quail, domestic duck or crossbred duck
  • meat of non-poultry wild birds such as wild duck, pheasant, sparrow or thrush.
  • fish meat and shellfish meat which are eaten in the course of a normal diet.
  • plant materials such as coffee and cocoa can also be used.
  • chicken meat is preferred for use because compound A can be
  • any treatment for reducing water-soluble proteins contained in a starting material may be performed, for example, by boiling in water at 100° C. to 160° C. for 30 minutes to several hours (preferably about 3 to 8 hours, more preferably about 3 to 4 hours).
  • a heating device e.g., a pressure cooker, an autoclave and so on can be combined for use depending on the intended conditions.
  • an additional liquid e.g., water
  • an additional starting material may further be added to adjust the concentration of an extract or beverage.
  • the heating step (2) is preferably accomplished at a high temperature under a high pressure (100° C. or more and 1 atm or more), for example, at 100° C. or more, and more preferably at 125° C. or more.
  • the heating time in the heating step (2) preferably ranges from 30 minutes to several hours, more preferably from about 3 to 7 hours.
  • a heating device a pressure cooker, an autoclave and so on can also be combined for use depending on the intended conditions.
  • the pretreatment step (1) and the heating step (2) may be performed continuously as a single step without liquid replacement.
  • the pretreatment step may be followed by removal of the pre-treated meat and then replacement of the liquid before the meat is subjected to the heating step. Since samples with lower Brix values can be obtained when liquid replacement is performed after the pretreatment step (1) and before the heating step (2), it is more desirable to use liquid replacement.
  • the concentration step so as to enrich compound A it is also more desirable to use liquid replacement between the pretreatment step (1) and the heating step (2) because good results will be obtained in terms of overall flavor including bitterness and slack, and the resulting samples will be less likely to affect the flavor of beverages upon addition.
  • heat treatment in the steps (1) and (2) is preferably performed in a solvent in order to prevent plant and animal materials from burning.
  • a solvent preferred for use include water, ethanol, or mixtures thereof. Namely, a plant or animal material containing proteins (preferably proteins rich in the contiguous phenylalanine (-Phe-Phe-) structure) is mixed with a solvent and subjected to heat treatment, followed by collection of the solvent to obtain a solution rich in compound A.
  • the power of filtration in the filtration step (3) may be selected as appropriate, depending on the form of foods into which the resulting extract is incorporated, and the filtration method may also be determined as appropriate by those skilled in the art. For example, in cases where the extract is used for solid foods (e.g., tablets) and where the resulting beverages do not need to be clear (e.g., canned beverages whose appearance is hidden in containers), it is sufficient to filter off sediments and filtration through a strainer may be used for this purpose. Alternatively, in a case where the extract needs to be clear (e.g., used for beverages in transparent bottles or plastic bottles), powerful filtration should be used. For clarification purposes, filtration through a strainer may be followed by filtration through a membrane (ion exchange membrane, RO membrane, zeta potential membrane) and/or filtration through diatomaceous earth, etc.
  • a membrane ion exchange membrane, RO membrane, zeta potential membrane
  • this solution rich in compound A may be used directly or, if necessary, may be concentrated to further increase the concentration of compound A.
  • the concentration step (4) may be accomplished by using an evaporator or by lyophilization, etc. After the concentration step (4), the resulting concentrate may be added to another liquid to produce the beverage of the present invention.
  • the extract and beverage of the present invention are intended to contain compound A in a dissolved state and have a Bx value of 0.01 or more.
  • the beverage of the present invention may be provided as appropriate in the form of a packaged beverage, when needed.
  • Compound A was evaluated for its enhancing effect on learning motivation by the method known in the art, i.e., Morris Water Maze (MWM).
  • MVM Morris Water Maze
  • mice Male, 9 weeks of age
  • mice will cause changes in their behavior and enter a state corresponding to depression.
  • mice were divided into 7 groups.
  • mice were each orally administered with compound A (Bachem AG (Bubendorf, Switzerland)) or with a comparative drug, fluvoxamine maleate. After 60 minutes, each mouse was transferred to the tank provided with the escape platform, and measured for the time required to find out the invisible escape platform placed below the water surface (i.e., the time required to reach the escape platform) to evaluate the spatial memory and learning ability of each mouse (MWM).
  • MWM spatial memory and learning ability of each mouse
  • FIG. 1 The results obtained are shown in FIG. 1 .
  • the time required to find out the escape platform was reduced when repeating the test, whereas the mice experiencing OSS showed reduced learning motivation and there was no reduction in the time required to reach the escape platform (OSS-Saline).
  • the group receiving compound A showed a dose-dependent reduction in the time required to reach the escape platform.
  • the time required to reach the escape platform at 10 days of MWM was reduced by around 20%, when compared to the control group (OSS-Saline) in which animals experiencing OSS were administered with physiological saline.
  • the time required to reach the escape platform at 10 days of MWM was substantially the same as that of the group (OSS-Fluvoxamine) receiving fluvoxamine maleate, which is frequently used as SSRI. This indicates that compound A has an enhancing effect on learning motivation.
  • mice were administered with 20 mg/kg compound A and then subjected to the MWM test.
  • a linear dipeptide Phe-Phe was administered at 20 mg/kg, followed by the MWM test.
  • beef meat, pork meat, fish, quail meat, corbicula clam and chicken meat (Black Chicken, Chicken) were used.
  • Each animal material was mixed with one volume of water and introduced into a container, followed by heat treatment in an autoclave at 135° C. for 4 hours (as a pretreatment step) and further at 135° C. for 4 hours (as a heating step).
  • the heat-treated liquid was collected and eluted with acetonitrile from a pretreatment column (OASIS MAX (Waters: 30 mg/1 cc)), followed by high performance liquid chromatography (HPLC) to quantify the content of compound A. Conditions for HPLC are as shown below. The results obtained are shown in FIG. 3 .
  • UV detector wavelength 215 nm
  • a compound A-containing liquid can also be collected from roasted coffee beans themselves, whereas compound A was not detected in coffee beverages extracted from roasted beans.
  • the pH, the content of compound A and the Bx value were measured for each extract to calculate the ratio of compound A content/Bx.
  • Bx values For determination of Bx values, a Bx meter (RX-5000 ⁇ : Atago Co., Ltd., Japan) was used for measurement.
  • extracts (sample Nos. 1 to 11) were prepared under 11 different conditions according to steps (1) to (3) shown below.
  • Extract 3 of Example 4 above (1 g) was added to liquids (100 g each), which had been adjusted to various pH values with citric acid and 3Na citrate, to test whether sediment occurred.
  • the extract was found to cause no sediment even when added to a liquid of pH 5 or more.
  • the conventionally used heating step was repeated again on a commercially available chicken extract to confirm how the content of compound A and Bx value were changed.
  • the conventionally used heating step is intended to mean a heating step in a pressure cooker for household use. It should be noted that the heating temperature in such a pressure cooker is about 120° C.
  • Extract 3 prepared in Example 4 above was added to prepare beverages.
  • the recipe used is as shown below. Each sample was adjusted to the same Bx value of 10. When compared to the commercially available chicken extract, the starting materials prepared according to this recipe were found to have a higher compound A content even at the same Bx value and further to be excellent in flavor and appearance.
  • the extract prepared in Example 4 above was lyophilized by spray drying to prepare an extract powder.
  • the extract (extract 3 of Example 4; 100 g) was taken into a 200 ml recovery flask. 2. This flask was stored in a freezer ( ⁇ 18° C.) for 2 or 3 days until the extract was completely frozen. 3. The flask was mounted on a lyophilizer (LABCONCO, set at ⁇ 40° C. or less) and lyophilized to complete dryness. 4. A dried powder was obtained in a yield of 1.38 g. 5. The powder obtained in 4 above was taken in an amount of 0.817 g and stirred in 99.183 g of water to give an ingestible liquid containing compound A at a concentration of 60 ⁇ g/100 g.
  • the present invention provides extracts and beverages having an improving effect on learning motivation and being highly safe without side effects.
  • the extracts of the present invention can be added to beverages and so on without impairing the taste inherent to foods and beverages.
  • the extracts or beverages of the present invention, as well as foods and beverages comprising the same can be ingested continuously over a long period of time as foods and beverages useful for improvement of learning motivation.

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US13/516,488 2009-12-25 2010-02-26 Extracts and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-, (3s,6s)- Abandoned US20120283270A1 (en)

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PCT/JP2010/053592 WO2011077759A1 (en) 2009-12-25 2010-02-26 Extracts and beverages containing 2, 5-piperazinedione, 3, 6-bis (phenylmethyl) -, (3s, 6s) -

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US9877960B2 (en) 2012-11-21 2018-01-30 Suntory Holdings Limited Learning and memory improver
US20180125106A1 (en) * 2016-11-09 2018-05-10 Campbell Soup Company Chicken products with reduced concentrations of off-flavor compounds
US10631559B2 (en) 2009-12-25 2020-04-28 Suntory Holdings Limited Acidic extracts and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-(3S,6S)-

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US8960290B2 (en) * 2011-12-19 2015-02-24 Halliburton Energy Services, Inc. Method for delayedly crosslinking environmentally friendly fluids
JP6669497B2 (ja) * 2013-06-10 2020-03-18 サントリーホールディングス株式会社 ジケトピペラジンを含有する植物エキス及びその製造方法
WO2017014149A1 (ja) * 2015-07-17 2017-01-26 サントリーホールディングス株式会社 抗肥満用組成物
JP6777632B2 (ja) 2015-07-27 2020-10-28 サントリーホールディングス株式会社 環状ジペプチド及び甘味料を含有する組成物
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US9623073B2 (en) 2009-12-25 2017-04-18 Suntory Holdings Limited Learning motivation improvers
US10631559B2 (en) 2009-12-25 2020-04-28 Suntory Holdings Limited Acidic extracts and beverages containing 2,5-piperazinedione,3,6-bis(phenylmethyl)-(3S,6S)-
US9877960B2 (en) 2012-11-21 2018-01-30 Suntory Holdings Limited Learning and memory improver
US20180125106A1 (en) * 2016-11-09 2018-05-10 Campbell Soup Company Chicken products with reduced concentrations of off-flavor compounds

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AU2010334163B2 (en) 2014-06-05
CN102665452A (zh) 2012-09-12
CN102665452B (zh) 2015-04-22
US20160206685A1 (en) 2016-07-21
AU2010334163A1 (en) 2012-07-19
TW201141392A (en) 2011-12-01
TWI535387B (zh) 2016-06-01

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