WO2011027551A1 - 硫化水素産生酵素阻害剤 - Google Patents

硫化水素産生酵素阻害剤 Download PDF

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Publication number
WO2011027551A1
WO2011027551A1 PCT/JP2010/005384 JP2010005384W WO2011027551A1 WO 2011027551 A1 WO2011027551 A1 WO 2011027551A1 JP 2010005384 W JP2010005384 W JP 2010005384W WO 2011027551 A1 WO2011027551 A1 WO 2011027551A1
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WO
WIPO (PCT)
Prior art keywords
hydrogen sulfide
producing enzyme
gallate
enzyme inhibitor
solution
Prior art date
Application number
PCT/JP2010/005384
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English (en)
French (fr)
Japanese (ja)
Inventor
紗奈恵 菊池
成瀬　敦
桜井　孝治
Original Assignee
株式会社ロッテ
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.)
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Publication date
Application filed by 株式会社ロッテ filed Critical 株式会社ロッテ
Priority to CN2010800397020A priority Critical patent/CN102482662A/zh
Publication of WO2011027551A1 publication Critical patent/WO2011027551A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/74—Biological properties of particular ingredients
    • A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
    • A61K2800/782—Enzyme inhibitors; Enzyme antagonists

Definitions

  • Hydrogen sulfide is a gas with an irritating odor and is known to be toxic, such as irritating the skin mucous membrane and causing respiratory paralysis. The toxicity is regarded as a problem in society, and removal of hydrogen sulfide is desired. Hydrogen sulfide is naturally contained in volcanic gases and hot springs, and is artificially generated by the petrochemical industry. In addition, sulfur compounds may be reduced by anaerobic bacteria to generate hydrogen sulfide. For example, anaerobic bacteria may propagate in filth and wastewater and hydrogen sulfide may be generated. In addition, some bacteria that generate hydrogen sulfide live in the living body as oral bacteria and intestinal bacteria. These bacteria emit hydrogen sulfide from food residues and in-vivo proteins. Furthermore, it is also known that endogenous hydrogen sulfide is produced in vivo.
  • Patent Document 1 discloses a volatile sulfur compound production inhibitor purified by Pseudomonas bacteria or Escherichia coli.
  • the inhibitor is an inhibitor intended for use in household products containing a specific aldehyde, undecenal, alicyclic ketone, or other fragrance as an active ingredient, and is not safe to use in the human body. Absent.
  • JP 2008-173441 A JP 2007-99672 A JP 2007-1112735 A
  • Fusobacterium nucleatum, Porphyromonas gingivalis, and Treponema denticola are all known as oral bacteria, have high ability to produce hydrogen sulfide and methyl mercaptan, and are also known as periodontal disease bacteria (Non-patent Document 2, Non-patent document 3).
  • inhibitor candidates are referred to herein as (+)-catechin: C, ( ⁇ )-epicatechin: EC, ( ⁇ )-epigallocatechin: EGC, ( ⁇ )-epicatechin gallate: ECg, ( ⁇ ) -Epigallocatechin gallate: EGCg, ( ⁇ )-gallocatechin gallate: GCg, ( ⁇ )-catechin gallate: Cg, gallic acid: G, zinc chloride: ZnCl 2 .
  • Gallic acid is known for its bactericidal activity, and its derivatives are used as oral compositions.
  • Zinc chloride is known to have bad breath prevention activity and is used as a mouthwash.
  • the above culture was further inoculated into 200 ml of TSB, and anaerobically cultured at 37 ° C. until 24 hours after the growth reached the stationary phase (culture period 2 days).
  • the culture solution was centrifuged at 3,000 ⁇ g, 10 min, 4 ° C. to remove the medium components, and the cells were collected.
  • 50 mM Tris-HCl buffer (pH 7.5) (6.05 g of trishydroxymethylaminomethane (molecular weight 121) dissolved in water, adjusted to pH 7.5 with HCl, and made up to 1 l).
  • the cells were washed, the buffer solution was removed, and the cells were frozen at -80 ° C.
  • MBTH 3-methyl-2-benzothiazolinone hydrazone
  • Methioninase Inhibition Test by Gas Chromatography
  • enzyme inhibition activity against methioninase was measured.
  • Methioninase produces methyl mercaptan, ammonia and ⁇ -ketobutyric acid using methionine as a substrate.
  • methioninase inhibition test by gas chromatography the inhibitory activity of each reagent on methioninase was compared using the amount of methyl mercaptan produced by methioninase as an index.
  • Toothpaste, mouse spray, troche, chewing gum, candy, gummy jelly, and beverage containing a hydrogen sulfide producing enzyme inhibitor comprising the catechins of the present invention were produced by conventional methods. Their formulations are shown below. Note that the scope of the present invention is not limited by these.
  • Prescription ethanol for mouse spray 10.0% by weight Glycerin 5.0 Fragrance 0.05 Coloring 0.001 ECg 1.0 Water remaining 100.0

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Organic Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Botany (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Non-Alcoholic Beverages (AREA)
PCT/JP2010/005384 2009-09-03 2010-09-01 硫化水素産生酵素阻害剤 WO2011027551A1 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN2010800397020A CN102482662A (zh) 2009-09-03 2010-09-01 硫化氢生成酶抑制剂

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009-203689 2009-09-03
JP2009203689A JP2011051946A (ja) 2009-09-03 2009-09-03 硫化水素産生酵素阻害剤

Publications (1)

Publication Number Publication Date
WO2011027551A1 true WO2011027551A1 (ja) 2011-03-10

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ID=43649106

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PCT/JP2010/005384 WO2011027551A1 (ja) 2009-09-03 2010-09-01 硫化水素産生酵素阻害剤

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JP (1) JP2011051946A (zh)
KR (1) KR20120073265A (zh)
CN (1) CN102482662A (zh)
TW (1) TW201124135A (zh)
WO (1) WO2011027551A1 (zh)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9790533B2 (en) 2011-05-13 2017-10-17 Biogen Ma Inc. Methods of preventing and removing trisulfide bonds
US10308706B2 (en) 2009-10-02 2019-06-04 Biogen Ma Inc. Methods of preventing and removing trisulfide bonds
EP3878460A4 (en) * 2018-11-05 2022-11-23 Amorepacific Corporation GREEN TEA EXTRACT WITH MODIFIED INGREDIENT CONTENT AND COMPOSITION THEREOF

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2497619B (en) 2011-12-15 2016-04-06 Lg Display Co Ltd Polarization glasses type stereoscopic image display
JP6373551B2 (ja) * 2012-05-30 2018-08-15 味の素株式会社 ガロタンニン含有組成物
JP6165077B2 (ja) * 2014-02-10 2017-07-19 森永乳業株式会社 含硫アミノ酸リアーゼ阻害剤
CN108635378B (zh) * 2018-04-23 2020-01-24 山东大学 一种用于日常口腔健康维护的口腔喷剂及其制备方法
CN108567773B (zh) * 2018-04-23 2020-04-17 山东大学 一种用于清除口臭的口腔喷剂及其制备方法
CN109043383A (zh) * 2018-09-05 2018-12-21 旌德县板桥现代渔业家庭农场 一种醋化乌龟蛋及其制备方法
CN116041100B (zh) * 2023-02-24 2023-10-20 东北农业大学 一种降低堆肥中硫化氢释放量的方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005162697A (ja) * 2003-12-04 2005-06-23 Lotte Co Ltd メチオニナーゼ阻害剤及びそれを含有する口腔用組成物並びに飲食品

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Publication number Priority date Publication date Assignee Title
WO2004012522A1 (en) * 2002-07-26 2004-02-12 Dsm Ip Assets B.V. Compositions comprising lactoferrin
JP2004105157A (ja) * 2002-09-20 2004-04-08 Pharmafoods Kenkyusho:Kk 糖類分解酵素阻害飲食組成物
JP2005082495A (ja) * 2003-09-04 2005-03-31 Pharma Foods International Co Ltd 脳細胞保護のための組成物
JP2006129757A (ja) * 2004-11-04 2006-05-25 Pharma Foods International Co Ltd 苦味やえぐ味を低減した緑茶抽出物、及び該抽出物を含有する飲食品

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005162697A (ja) * 2003-12-04 2005-06-23 Lotte Co Ltd メチオニナーゼ阻害剤及びそれを含有する口腔用組成物並びに飲食品

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Abstracts of the General Meeting of the American Society for Microbiology, 2003", vol. 103, article ZHU M. ET AL.: "Effect of Tea Polyphenols on Growth and H2S Production of Halitosis Causing Bacteria", pages: 226 *
SANAE KIKUCHI ET AL.: "Koshu ni Kan'yo suru Koku Nai Saikin Yurai Sokoso ni Taisuru Ryokucha Catechin-rui no Sogai Koka", JOURNAL OF DENTAL HEALTH, vol. 59, no. 4, 30 August 2009 (2009-08-30), pages 391 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10308706B2 (en) 2009-10-02 2019-06-04 Biogen Ma Inc. Methods of preventing and removing trisulfide bonds
US9790533B2 (en) 2011-05-13 2017-10-17 Biogen Ma Inc. Methods of preventing and removing trisulfide bonds
US10590454B2 (en) 2011-05-13 2020-03-17 Biogen Ma Inc. Methods of preventing and removing trisulfide bonds
EP3878460A4 (en) * 2018-11-05 2022-11-23 Amorepacific Corporation GREEN TEA EXTRACT WITH MODIFIED INGREDIENT CONTENT AND COMPOSITION THEREOF

Also Published As

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TW201124135A (en) 2011-07-16
CN102482662A (zh) 2012-05-30
JP2011051946A (ja) 2011-03-17
KR20120073265A (ko) 2012-07-04

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