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WO2014092175A1 - Polyphénol spécifique utilisé dans des produits alimentaires et de boisson, des compléments, des produits pharmaceutiques, et similaires et procédé de fabrication dudit polyphénol spécifique - Google Patents

Polyphénol spécifique utilisé dans des produits alimentaires et de boisson, des compléments, des produits pharmaceutiques, et similaires et procédé de fabrication dudit polyphénol spécifique Download PDF

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Publication number
WO2014092175A1
WO2014092175A1 PCT/JP2013/083429 JP2013083429W WO2014092175A1 WO 2014092175 A1 WO2014092175 A1 WO 2014092175A1 JP 2013083429 W JP2013083429 W JP 2013083429W WO 2014092175 A1 WO2014092175 A1 WO 2014092175A1
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WO
WIPO (PCT)
Prior art keywords
polyphenol
gel filtration
specific
clpr
tetramer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2013/083429
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English (en)
Japanese (ja)
Inventor
みどり 夏目
公一郎 角
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Meiji Co Ltd
Original Assignee
Meiji Co Ltd
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 Meiji Co Ltd filed Critical Meiji Co Ltd
Priority to HK15108393.9A priority Critical patent/HK1207646B/xx
Priority to JP2014552097A priority patent/JP6297501B2/ja
Priority to CN201380063561.XA priority patent/CN104837824B/zh
Publication of WO2014092175A1 publication Critical patent/WO2014092175A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
    • C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • the present invention relates to a specific polyphenol useful for foods and drinks, supplements, pharmaceuticals, and the like, and a method for producing the same.
  • Polyphenols are said to "suppress the action of active oxygen, which is said to cause various diseases such as cancer and arteriosclerosis", and “have an allergy suppressing effect and a stress suppressing effect”.
  • plants containing polyphenols, processed products and extracts of the plants, and the like are widely used as raw materials and additives in the fields of foods and drinks, supplements and pharmaceuticals.
  • cacao is richer in polyphenols than other plants.
  • cocoa powder and cocoa extract are attracting particular attention as such raw materials and additives.
  • cocoa-derived polyphenol examples include, for example, a monomer catechin, a dimer procyanidin B2, a trimer procyanidin C1, and a tetramer cinnamtannin A2. Etc.
  • an object of the present invention is to provide a method for producing a polyphenol having a relatively high purity and a tetramer having a relatively high purity by accurately separating the polyphenol having a tetramer or more from the polyphenol mixture.
  • an eluent containing no acid (hereinafter also referred to as “acid-free eluent”) is used to convert a polyphenol of tetramer or higher from a polyphenol mixture into a gel filtration fraction.
  • “polyphenol” is a general term for plant components having a plurality of phenolic hydroxyl groups.
  • the “polyphenol mixture” referred to here is, for example, a cacao extract.
  • the tetramer or higher polyphenol (hereinafter also referred to as “specific polyphenol”) is preferably a tetramer or higher procyanidin.
  • Procyanidin is an oligomer of catechins such as catechin and epicatechin.
  • the upper limit of the degree of polymerization of polyphenol or procyanidin is preferably 20.
  • liquid chromatography including high performance liquid chromatography
  • gel filtration chromatography can be used. At this time, it is preferable to use silica particles chemically bonded with glyceropropyl groups as the gel filtration material.
  • composition of the acid-free eluent as the eluent in the gel filtration fractionation.
  • the composition of the acid-free eluent is preferably changed in at least four stages. It is because it can suppress effectively that this specific polyphenol mixes the polyphenol below a trimer.
  • this specific polyphenol production method As a result of intensive studies by the inventors of the present application, when this specific polyphenol production method is used, a tetraphenol or higher polyphenol is accurately separated from a polyphenol mixture to produce a relatively high purity tetramer or higher polyphenol. It became clear that it could be done. At this time, it is preferable that this specific polyphenol does not contain catechin, epicatechin and procyanidins of trimer or less. However, this means “substantially” free of catechins, epicatechins and trimeric procyanidins.
  • this specific polyphenol has a ratio of “total mass of polyphenols of tetramer or more” to “total mass of catechin, epicatechin and polyphenols of trimer or less” of 9 or more, preferably 10 or more, more preferably 11 In other words, it can be paraphrased as a polyphenol mixture, more preferably 12 or more.
  • the upper limit of this ratio is infinity ( ⁇ ), and the higher the ratio, the better. For example, the upper limit of this ratio is 100.
  • the specific polyphenol according to the second aspect of the present invention has a polyphenol content of trimer or less of 10% by mass or less.
  • the content of polyphenols of trimer or less is preferably 9% by mass or less, more preferably 8% by mass or less, further preferably 7% by mass or less, and 6% by mass or less. Particularly preferred is 5% by mass or less.
  • the specific polyphenol is a raw material for food and drink (material, composition), a raw material for supplement (material, composition). And as a raw material for pharmaceuticals (raw material, composition) and the like, more preferably as a raw material for food and drink and a raw material for supplement, and further more preferable as a raw material for food and drink.
  • Example 3 is a chart showing the results of gel filtration fractionation according to Example 1. It is a chart which shows the result of the gel filtration fractionation concerning Example 2.
  • 2 is a chart showing analysis results of the content of high polymerization procyanidins contained in each fraction after gel filtration fractionation according to Example 2 (a) cocoa extract (CLPr), b) low polymerization fraction (CLPr ⁇ L), c) High polymerization fraction (CLPr-H)). It is a chart which shows the result of the gel filtration fraction which concerns on the comparative example 1.
  • the tetrameric or higher cocoa procyanidins (hereinafter also referred to as “highly polymerized procyanidins”) according to an embodiment of the present invention can be obtained by subjecting a cocoa extract to gel filtration fractionation.
  • an “eluent containing no acid” is used as the eluent.
  • a cocoa extract may purchase a commercial item etc., and may extract it from a cocoa bean and cacao powder by a well-known method.
  • the “cocoa beans” that can be used in the embodiment of the present invention are not limited by the production area, the growth situation, the presence or absence of roasting, and the like.
  • HPLC high performance liquid chromatography
  • GFC gel filtration chromatography
  • HPLC high performance liquid chromatography
  • GFC gel filtration chromatography
  • sica particles chemically bonded with glyceropropyl groups for normal phase separation are used to elute from molecules with low polarity (in the present invention, polyphenols having a low degree of polymerization). It is preferable to carry out HPLC, GFC, etc. using the principle of elution in order.
  • the “eluent containing no acid” as used herein means an eluent substantially free of acetic acid, phosphoric acid, formic acid, trifluoroacetic acid and the like that is generally added to the eluent.
  • a polar organic solvent such as acetonitrile / methanol, water, or a mixed solution thereof is preferably used.
  • No acid is judged based on the fact that it does not substantially affect the gel filtration fraction of cocoa polyphenols of trimer or less and cocoa polyphenols (cacaoprocyanidins) of tetramer or more. be able to.
  • the present invention will be described in more detail with reference to examples.
  • this invention is not limited to the Example shown below.
  • the term “low polymerization” means that the degree of polymerization is 1 or more and 3 or less, that is, a monomer to trimer
  • the term “high polymerization” means that the degree of polymerization is 4 That is, it means a tetramer or more.
  • Example 1 (1) Preparation of raw material solution After CLPr was dissolved in an aqueous methanol solution (50% by mass) so that the concentration of the cacao extract (hereinafter also referred to as “CLPR”) native to Ecuador was 30 mg / mL, this CLPr solution was The raw material liquid was prepared by filtering through a regenerated cellulose membrane having a pore diameter of 0.45 ⁇ m.
  • CLPR cacao extract
  • CLPr-L mainly contains catechin, epicatechin and dimers and trimers thereof
  • CLPr-H mainly contains procyanidins of tetramer or higher. That is, the content of highly polymerized procyanidins contained in each fraction and the yield of each fraction were the same as the results of Example 2 described later.
  • the fraction point a point in time where CLPr-H contained no catechin, epicatechin and dimer or trimer procyanidin as much as possible was set.
  • Apparatus Semi-preparative liquid chromatography system (manufactured by Shimadzu, system configuration: LC-6AD, 2 units, CBM-20A, CTO-20A, SIL-10AF, SPD-20A, FRC-10A, LCsolution software) Column: Deverosil 100 Diol-5 8.0 ⁇ 300mm ⁇ Flow rate: 2.4 ml / min ⁇ Detection wavelength: UV 280 nm Eluent: acetonitrile and methanol aqueous solution (97% by mass) Gradient: (mass% of aqueous methanol solution (97 mass%)) 0 (0 min), 20 (4-9 min), 40 (13-18 min), 0 (20-30 min)
  • Example 2 Preparation of raw material liquid CLPr was prepared in the same manner as in Example 1. (2) Gel filtration fraction The environmental conditions of the HPLC system were changed as shown below, and the above-mentioned raw material liquid was injected into the HPLC system in 1960 ⁇ L. Then, the elution fraction from 45 to 85 minutes after injection of the raw material liquid was CLPr-L, and the elution fraction from 90 to 135 minutes after injection of the raw material liquid was CLPr-H. Each was fractionated (see FIG. 2).
  • CLPr-H contained tetramer or higher procyanidin at 90% by mass or more.
  • procyanidins of tetramer or higher were not detected in CLPr-L. These procyanidins were quantified by preparing a calibration curve with epicatechin according to the method of reverse phase HPLC analysis and calculating the procyanidin concentration of each degree of polymerization as epicatechin equivalent.
  • Example 1 Preparation of raw material liquid CLPr was prepared in the same manner as in Example 1. (2) Gel filtration fraction The environmental conditions of the HPLC system were changed as shown below, and 50 ⁇ L of the above raw material solution was injected into the HPLC system. Example 1 except that the elution fraction from 8 minutes to 18.5 minutes after injection of the raw material liquid was CLPr-L, and the elution fraction from 19 minutes to 30 minutes after injection of the raw material liquid was CLPr-H. In the same manner as above, each fraction was collected (see FIG. 4). As shown in FIG. 4, in this comparative example, the peaks of the trimer and the tetramer are close to each other. For this reason, CLPr-H contains a relatively large amount of catechin, epicatechin and their dimers and trimers procyanidins, and it was difficult to obtain high-purity CLPr-H. .
  • Apparatus Semi-preparative liquid chromatography system (manufactured by Shimadzu, system configuration: LC-6AD, 2 units, CBM-20A, CTO-20A, SIL-10AF, SPD-20A, FRC-10A, LCsolution software) Column: Deverosil 100 Diol-5 8.0 ⁇ 300mm ⁇ Flow rate: 2.4 ml / min ⁇ Detection wavelength: UV 280 nm Eluent: Acetonitrile / acetonitrile solution (2% by mass) and acetic acid / methanol aqueous solution (acetic acid: 2% by mass, methanol 95% by mass) Gradient: (mass% of acetic acid / methanol aqueous solution) 0 (0 min), 40 (18-23 min), 0 (25-35 min)
  • highly-purified highly polymerized cacaoprocyanidins that is, cacaoprocyanidins having a tetramer or higher
  • the method for producing a specific polyphenol according to the present invention is not limited to extraction of highly polymerized procyanidins from cocoa powder and cocoa extract by gel filtration fractionation, but other plants and foods and drinks containing polyphenols such as tea and fruits. It can also be applied when polyphenols are extracted by gel filtration fractionation (eg grapes, apples, blueberries, etc.), cereals (sesame seeds, soybeans, buckwheat etc.) or powders thereof, or extracts thereof.
  • the highly polymerized procyanidins produced by the method for producing the specific polyphenol according to the present invention can be used not only as an active ingredient of pharmaceuticals such as blood glucose level control agents, but also added to foods and drinks, supplements, etc. It can also be used.
  • these pharmaceuticals etc. may be administered orally, may be administered by tube, and may be administered enterally.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Vascular Medicine (AREA)
  • Neurosurgery (AREA)
  • Urology & Nephrology (AREA)
  • Biochemistry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Toxicology (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention aborde le problème de proposer un procédé de fabrication d'un polyphénol à ≥ 4 mères à pureté élevée de façon comparative par isolement de façon précise dudit polymère à ≥ 4 mères à partir d'un mélange polyphénol. Ce procédé de fabrication d'un polyphénol spécifique utilise un éluant ne contenant pas d'acide pour isoler un polyphénol à ≥ 4 mères à partir d'un mélange de polyphénol par fractionnement par filtration sur gel, par exemple chromatographie liquide ou chromatographie par filtration sur gel.
PCT/JP2013/083429 2012-12-14 2013-12-13 Polyphénol spécifique utilisé dans des produits alimentaires et de boisson, des compléments, des produits pharmaceutiques, et similaires et procédé de fabrication dudit polyphénol spécifique Ceased WO2014092175A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
HK15108393.9A HK1207646B (en) 2012-12-14 2013-12-13 Specific polyphenol used in food and drink products, supplements, pharmaceuticals, and the like and method for manufacturing said specific polyphenol
JP2014552097A JP6297501B2 (ja) 2012-12-14 2013-12-13 飲食品、サプリメントおよび医薬品等に用いられる特定カカオプロシアニジンおよびその製造方法
CN201380063561.XA CN104837824B (zh) 2012-12-14 2013-12-13 饮食品、补品和医药品等使用的特定多酚及其制造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2012273126 2012-12-14
JP2012-273126 2012-12-14

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WO2014092175A1 true WO2014092175A1 (fr) 2014-06-19

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JP (1) JP6297501B2 (fr)
CN (1) CN104837824B (fr)
WO (1) WO2014092175A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06247959A (ja) * 1993-02-24 1994-09-06 Suntory Ltd フラボノイド重合物およびこれを有効成分とするグルコシルトランスフェラーゼ阻害剤
JPH10218769A (ja) * 1997-02-06 1998-08-18 Kikkoman Corp 抗潰瘍剤
WO2000064883A1 (fr) * 1999-04-23 2000-11-02 Kyowa Hakko Kogyo Co., Ltd. Methodes de purification d'oligomeres de proanthocyanidine
JP2005314316A (ja) * 2004-04-30 2005-11-10 Kikkoman Corp 抗ｓａｒｓコロナウイルス剤
WO2006068212A1 (fr) * 2004-12-22 2006-06-29 Kikkoman Corporation Inhibiteur de lipase et medicament prophylactique / remede pour maladies cutanees
JP2010260823A (ja) * 2009-05-08 2010-11-18 Fujicco Co Ltd プロアントシアニジンの分離精製方法
WO2010150538A1 (fr) * 2009-06-23 2010-12-29 独立行政法人国立循環器病研究センター Médicament destiné à inhiber le récepteur de type lectine des ldl oxydées et médicament destiné à prévenir l'artériosclérose
JP2011178728A (ja) * 2010-03-02 2011-09-15 Kobe Univ Ａｍｐｋ活性化剤、ｇｌｕｔ４活性化剤、およびそれらを用いた医薬品・飲食品

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06247959A (ja) * 1993-02-24 1994-09-06 Suntory Ltd フラボノイド重合物およびこれを有効成分とするグルコシルトランスフェラーゼ阻害剤
JPH10218769A (ja) * 1997-02-06 1998-08-18 Kikkoman Corp 抗潰瘍剤
WO2000064883A1 (fr) * 1999-04-23 2000-11-02 Kyowa Hakko Kogyo Co., Ltd. Methodes de purification d'oligomeres de proanthocyanidine
JP2005314316A (ja) * 2004-04-30 2005-11-10 Kikkoman Corp 抗ｓａｒｓコロナウイルス剤
WO2006068212A1 (fr) * 2004-12-22 2006-06-29 Kikkoman Corporation Inhibiteur de lipase et medicament prophylactique / remede pour maladies cutanees
JP2010260823A (ja) * 2009-05-08 2010-11-18 Fujicco Co Ltd プロアントシアニジンの分離精製方法
WO2010150538A1 (fr) * 2009-06-23 2010-12-29 独立行政法人国立循環器病研究センター Médicament destiné à inhiber le récepteur de type lectine des ldl oxydées et médicament destiné à prévenir l'artériosclérose
JP2011178728A (ja) * 2010-03-02 2011-09-15 Kobe Univ Ａｍｐｋ活性化剤、ｇｌｕｔ４活性化剤、およびそれらを用いた医薬品・飲食品

Also Published As

Publication number Publication date
HK1207646A1 (en) 2016-02-05
CN104837824A (zh) 2015-08-12
CN104837824B (zh) 2017-10-20
JP6297501B2 (ja) 2018-03-20
JPWO2014092175A1 (ja) 2017-01-12

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