[go: up one dir, main page]

US20180015017A1 - Use of glucosylglycerol - Google Patents

Use of glucosylglycerol Download PDF

Info

Publication number
US20180015017A1
US20180015017A1 US15/717,093 US201715717093A US2018015017A1 US 20180015017 A1 US20180015017 A1 US 20180015017A1 US 201715717093 A US201715717093 A US 201715717093A US 2018015017 A1 US2018015017 A1 US 2018015017A1
Authority
US
United States
Prior art keywords
glucosylglycerol
enzyme
substances
cell protective
human skin
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.)
Abandoned
Application number
US15/717,093
Inventor
Julia Kruger
Gerhard Stumm
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.)
Bitop AG
Original Assignee
Bitop AG
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 Bitop AG filed Critical Bitop AG
Priority to US15/717,093 priority Critical patent/US20180015017A1/en
Assigned to BITOP AG reassignment BITOP AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KRUGER, JULIA, STUMM, GERHARD
Publication of US20180015017A1 publication Critical patent/US20180015017A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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

Definitions

  • the invention relates to the use of glucosylglycerol within the framework of cosmetic or dermatological preparations.
  • Glucosylglycerol or more specific 2-O- ⁇ -D-glucosylglycerol, is a natural substance synthetized, for example, from cyanobacteria which make use of its properties for osmoprotective purposes. In this manner cyanobacteria are capable of growing in saline media with concentrations of up to 1.5 M NaCl. The molecule accumulates in high concentrations in the cytoplasm and in this way causes the existing osmotic pressure existing in such an environment due to the high salt concentration to be reduced thus protecting the cell against water losses.
  • An example here is the cyanobacterium Synechocystis sp. PCC 6803.
  • the molecule is also synthetized by plants of genus myrothamnus . These plants are growing in humid-to-dry environments. Myrothamnus flabellifolia is a small shrub found in the southern region of Africa growing on rock slabs up to a height of 60 cm. The plant survives completely unharmed and in desiccated condition drought periods occurring in the southern African region and lasting several months. However, as soon as it rains again the plant begins to sprout within a few hours so that it is also known under the byword of “resurrection plant”.
  • the structure of 2-O- ⁇ -D-glucosylglycerol is as follows:
  • the invention relates to the use of glucosylglycerol with a view to increasing the expression of cell protective enzymes for the protection and stabilization of human skin and/or mucous membranes.
  • glucosylglycerol was proved based on tests conducted with keratinocytes and fibroblasts. In these tests appropriate cell cultures were treated with a glucosylglycerol solution and the transcribed mRNA quantified. For this purpose the mRNA was first extracted to produce a 33 P labeled target with the help of a reverse transcriptase. Following this, these targets were applied to a cDNA chip and the radioactivity measured by means of the phosphor imaging method.
  • the cDNA chip contained an array of the cDNAs of various proteins.
  • Cell protection enzymes are in particular those that are capable of decomposing reactive oxygen compounds.
  • An example here is the superoxide dismutase which is an enzyme that protects eukaryotic cells against reactive superoxide ions.
  • the oxidized form of the enzyme reacts with a superoxide anion thus producing oxygen and the reduced form of the enzyme.
  • This form then reacts with a second superoxide anion giving rise to the formation of hydrogen peroxide and causing a re-formation of the oxidized form of the enzyme.
  • This can expediently be expressed by the following equation:
  • catalase which disproportionates hydrogen peroxide to form oxygen and water. In this manner catalase similar to superoxide dismutase reduces the oxidative stress acting on the skin cells.
  • Glutathione peroxidase as well plays a significant role in the cellular defense system combatting negative effects of oxidative stress. Glutathione peroxidase catalyzes the glutathione-dependent reduction of organic peroxides and hydrogen peroxide.
  • cell protection enzymes which are capable of decomposing reactive oxygen compounds, in particular superoxide anions, hydroxyl radicals and peroxides, play an important part in the protection against oxidative stress.
  • reactive oxygen compounds in particular superoxide anions, hydroxyl radicals and peroxides
  • oxidative stress As interface and surface of the human body the skin/mucous membrane is exposed to numerous external stresses.
  • Human skin is an organ that consists of a variety of specialized cell types—keratinocytes, melanocytes, Langerhans cells, Merkel cells and others—and protects the body against external influences.
  • Physical influences are, inter alia, thermal and mechanical influences as well as the effects of radiation such as, for example, UV, VIS and IR radiation.
  • Chemical influences particularly involve, inter alia, the exposure to and effects of chemicals, toxins, free radicals, allergens, denaturing substances, substances attaching to DNA and substances damaging or deactivating proteins. Airborne particulate may also have detrimental effects. External biological influences mean the effects caused by foreign organisms and their metabolic products. Human skin may also be affected by thermal influences. According to the present invention the use of glucosylglycerol can protect the skin against influences of the nature described above.
  • cell protection enzymes may also be upregulated, for example DNA repairing enzymes such as ligases. Chaperones represent another class and facilitate the correct folding of proteins.
  • the glucosylglycerol employed is preferably the naturally occurring 2-O- ⁇ -D glucosylglycerol which for example is accumulated by cyanobacteria of genus Synechocystis .
  • cyanobacteria of genus Synechocystis a group consisting of cyanobacteria, genus Synechocystis.
  • comparable effects can also be expected from the ⁇ -glycosidic linkage of glucose to the glycerol molecule or from the linkage of glucose to glycerol at the 1-position.
  • the following glucosylglycerols are thus conceivable, with only the notation of the molecules in the D-configuration being represented here:
  • Esters of glucosylglycerol may also be put to use.
  • the glucosylglycerol may be employed for purposes described hereinbefore in the form of cosmetic, dermatological and pharmaceutical preparations.
  • the concentration may, for example, range between 0.001% w/w and 10% w/w, in particular between 0.01% w/w and 6% w/w in relation to the total weight of the preparation.
  • the glucosylglycerol is provided in an aqueous solution.
  • emulsions and microemulsions of the type water-in-oil (W/O) or of type oil-in-water (O/W) are basically conceivable as well.
  • Customary cosmetic auxiliary agents may be used, for example carrier substances, preservation agents, bactericides, perfumes, solutizers, vitamins, stabilizers, antifoaming agents, thickeners, colorants, surfactants, emulsifiers, moisturizers and the like.
  • the cosmetic or dermatological preparations containing glucosylglycerol are meant to be administered topically. They may, for example, be used in the form of solutions, suspensions, emulsions, pastes, ointments, gels, creams, lotions, powder, soaps, surfactant-containing cleansing preparations, oils, sprays and lipsticks.
  • Ointments, pastes, creams and gels may contain customary carrier substances such as, for example, animal and vegetable fats, waxes, paraffins, starch, traganth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talcum and zinc oxide or mixtures/blends of these substances.
  • customary carrier substances such as, for example, animal and vegetable fats, waxes, paraffins, starch, traganth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talcum and zinc oxide or mixtures/blends of these substances.
  • powders and sprays may contain the customary propellants, e.g. propane/butane or dimethyl ether.
  • Solutions and emulsions may contain customary carrier substances such as solvents, solutizers and emulsifiers or oils.
  • Suspensions typically contain additional carrier substances such as water or ethanol.
  • Glucosylglycerol may be produced in accordance with a method described in WO 2008/034158 A2.
  • a saccharose phosphorylase is allowed to interact with a blend that has a glucosyl donor and glycerol as glucosyl acceptor.
  • the glucosyl donor is saccharose.
  • NHEK epidermal keratinocytes
  • NHDF dermal fibroblasts
  • Keratinocytes Keratinocyte-SFM (Invitrogen 17005-034) blended with epidermal growth factor (EGF) 0.25 ng/ml, pituitary extract (PE) 25 ⁇ g/ml (Invitrogen 3700015), Gentamycin 25 ⁇ m/ml (Sigma G1397).
  • EGF epidermal growth factor
  • PE pituitary extract
  • Gentamycin 25 ⁇ m/ml
  • Fibroblasts DMEM (Invitrogen 21969035), blended with L-glutamine 2 mM (Invitrogen 25030024), Penicillin 50 Ul/ml/Streptomycin 50 ⁇ g/ml (Invitrogen 15070063), fetal calf serum 10% (FCS, Invitrogen 10270098).
  • the extraction of mRNA of each culture was achieved using TriReagent as per a standard protocol.
  • the relevant cDNAs with 33 P-labeled targets was produced by reverse transcription of mRNA using [ ⁇ 33 P]-dATP and oligodT.
  • the labeled cDNA targets were hybridized to the specific cDNA probes covalently fixed to minichips. After thorough washing the relative amount of the hybridized targets was determined by means of the phosphor imaging method. This analysis was performed by measuring the radioactivity by means of a “Cyclone” Phosphor Imager (Packard Instruments; 72 hours exposure time) and using the ImageQuant TL-Software (Amersham Biosiences).

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Dermatology (AREA)
  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Toxicology (AREA)
  • Biochemistry (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The invention relates to the use of glucosylglycerol or glucosylglycerol esters with a view to increasing the expression of cell protective enzymes for the protection and stabilization of human skin and/or mucous membranes. It has been demonstrated that glucosylglycerol plays an effective role in the stimulation and activation of cell protective enzymes such as superoxide dismutase. It is thus possible in this manner to protect human skin cells effectively against damaging external influences.

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • This application is a continuation of U.S. application Ser. No. 13/060,122, filed on Apr. 27, 2011, which was the National Stage of International Application No. PCT/EP2009/006083, filed on Aug. 21, 2009, which claims the priority of German Application No. 10 2008 039 231.6, filed on Aug. 22, 2008, all of which are incorporated by reference herein.
    • BACKGROUND Field of Invention
  • The invention relates to the use of glucosylglycerol within the framework of cosmetic or dermatological preparations.
    • Related Art
  • DE 195 40 749 A1 describes the use of glycosyl glycerides in cosmetic and dermatological preparations. Substances of this nature can be put to use as so-called moisturizers, that is as substances having moisture-adding properties. Especially preferred here is the use of 2-O-β-D-glucosylglycerol.
  • Glucosylglycerol, or more specific 2-O-α-D-glucosylglycerol, is a natural substance synthetized, for example, from cyanobacteria which make use of its properties for osmoprotective purposes. In this manner cyanobacteria are capable of growing in saline media with concentrations of up to 1.5 M NaCl. The molecule accumulates in high concentrations in the cytoplasm and in this way causes the existing osmotic pressure existing in such an environment due to the high salt concentration to be reduced thus protecting the cell against water losses. An example here is the cyanobacterium Synechocystis sp. PCC 6803.
  • Furthermore, the molecule is also synthetized by plants of genus myrothamnus. These plants are growing in humid-to-dry environments. Myrothamnus flabellifolia is a small shrub found in the southern region of Africa growing on rock slabs up to a height of 60 cm. The plant survives completely unharmed and in desiccated condition drought periods occurring in the southern African region and lasting several months. However, as soon as it rains again the plant begins to sprout within a few hours so that it is also known under the byword of “resurrection plant”. The structure of 2-O-α-D-glucosylglycerol is as follows:
  • Figure US20180015017A1-20180118-C00001
    • SUMMARY
  • Surprisingly, it has now been found and ascertained through tests conducted with human skin cells that glucosylglycerols are capable of increasing the expression of cell protective enzymes. Therefore, the invention relates to the use of glucosylglycerol with a view to increasing the expression of cell protective enzymes for the protection and stabilization of human skin and/or mucous membranes.
    • DETAILED DESCRIPTION
  • The efficiency of glucosylglycerol could be proved based on tests conducted with keratinocytes and fibroblasts. In these tests appropriate cell cultures were treated with a glucosylglycerol solution and the transcribed mRNA quantified. For this purpose the mRNA was first extracted to produce a 33P labeled target with the help of a reverse transcriptase. Following this, these targets were applied to a cDNA chip and the radioactivity measured by means of the phosphor imaging method. The cDNA chip contained an array of the cDNAs of various proteins.
  • It has been found in this context that the expression of cell protection enzymes is upregulated. Cell protection enzymes are in particular those that are capable of decomposing reactive oxygen compounds. An example here is the superoxide dismutase which is an enzyme that protects eukaryotic cells against reactive superoxide ions. In this process the oxidized form of the enzyme reacts with a superoxide anion thus producing oxygen and the reduced form of the enzyme. This form then reacts with a second superoxide anion giving rise to the formation of hydrogen peroxide and causing a re-formation of the oxidized form of the enzyme. This can expediently be expressed by the following equation:

  • 2O2 −+2H+→H2O2+O2
  • Another important enzyme in this context is the catalase which disproportionates hydrogen peroxide to form oxygen and water. In this manner catalase similar to superoxide dismutase reduces the oxidative stress acting on the skin cells.
  • Glutathione peroxidase as well plays a significant role in the cellular defense system combatting negative effects of oxidative stress. Glutathione peroxidase catalyzes the glutathione-dependent reduction of organic peroxides and hydrogen peroxide.
  • The so-called cell protection enzymes which are capable of decomposing reactive oxygen compounds, in particular superoxide anions, hydroxyl radicals and peroxides, play an important part in the protection against oxidative stress. As interface and surface of the human body the skin/mucous membrane is exposed to numerous external stresses. Human skin is an organ that consists of a variety of specialized cell types—keratinocytes, melanocytes, Langerhans cells, Merkel cells and others—and protects the body against external influences. In this context a distinction must be made between physical, chemical and biological factors that may have impact on human skin. Physical influences are, inter alia, thermal and mechanical influences as well as the effects of radiation such as, for example, UV, VIS and IR radiation. Chemical influences particularly involve, inter alia, the exposure to and effects of chemicals, toxins, free radicals, allergens, denaturing substances, substances attaching to DNA and substances damaging or deactivating proteins. Airborne particulate may also have detrimental effects. External biological influences mean the effects caused by foreign organisms and their metabolic products. Human skin may also be affected by thermal influences. According to the present invention the use of glucosylglycerol can protect the skin against influences of the nature described above.
  • How cell protection enzymes are stimulated and activated could in particular be shown in the case of the superoxide dismutases SOD-1 and SOD-2. Regarding keratinocytes and using a 0.5-% glucosylglycerol solution it was possible to increase the expression of SOD-1 4.7 times within 24 hours, and raise it 19.6 times within 96 hours. As far as SOD-2 was concerned tests with fibroblasts using a 1-% glucosylglycerol solution have shown a 25.4 times higher expression within 24 hours and within 96 hours a 34.4-fold increase could be achieved.
  • Aside from enzymes decomposing reactive oxygen compounds other cell protection enzymes may also be upregulated, for example DNA repairing enzymes such as ligases. Chaperones represent another class and facilitate the correct folding of proteins.
  • The glucosylglycerol employed is preferably the naturally occurring 2-O-α-D glucosylglycerol which for example is accumulated by cyanobacteria of genus Synechocystis. However, comparable effects can also be expected from the β-glycosidic linkage of glucose to the glycerol molecule or from the linkage of glucose to glycerol at the 1-position. The following glucosylglycerols are thus conceivable, with only the notation of the molecules in the D-configuration being represented here:
  • Figure US20180015017A1-20180118-C00002
  • Esters of glucosylglycerol may also be put to use.
  • The glucosylglycerol may be employed for purposes described hereinbefore in the form of cosmetic, dermatological and pharmaceutical preparations. The concentration may, for example, range between 0.001% w/w and 10% w/w, in particular between 0.01% w/w and 6% w/w in relation to the total weight of the preparation.
  • In particular, the glucosylglycerol is provided in an aqueous solution. Nevertheless, emulsions and microemulsions of the type water-in-oil (W/O) or of type oil-in-water (O/W) are basically conceivable as well.
  • Customary cosmetic auxiliary agents may be used, for example carrier substances, preservation agents, bactericides, perfumes, solutizers, vitamins, stabilizers, antifoaming agents, thickeners, colorants, surfactants, emulsifiers, moisturizers and the like.
  • The cosmetic or dermatological preparations containing glucosylglycerol are meant to be administered topically. They may, for example, be used in the form of solutions, suspensions, emulsions, pastes, ointments, gels, creams, lotions, powder, soaps, surfactant-containing cleansing preparations, oils, sprays and lipsticks.
  • Ointments, pastes, creams and gels may contain customary carrier substances such as, for example, animal and vegetable fats, waxes, paraffins, starch, traganth, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicic acid, talcum and zinc oxide or mixtures/blends of these substances.
  • In addition to the customary carrier substances powders and sprays may contain the customary propellants, e.g. propane/butane or dimethyl ether.
  • Solutions and emulsions may contain customary carrier substances such as solvents, solutizers and emulsifiers or oils.
  • Suspensions typically contain additional carrier substances such as water or ethanol.
  • Glucosylglycerol may be produced in accordance with a method described in WO 2008/034158 A2. In this case a saccharose phosphorylase is allowed to interact with a blend that has a glucosyl donor and glycerol as glucosyl acceptor. Preferably, the glucosyl donor is saccharose.
  • The increase of the expression of cell protective enzymes could be shown as follows:
  • The investigations were carried out with epidermal keratinocytes (NHEK, normal human epidermal keratinocytes) and dermal fibroblasts (NHDF, normal human dermal fibroblasts). In the case of the keratinocytes a 0.5-% (w/w) and in the case of the fibroblasts a 1-% (w/w) aqueous glucosylglycerol solution was used for the treatment.
    • Culture Conditions:
  • 37° C., 5% CO2
    • Culturing Medium:
  • Keratinocytes: Keratinocyte-SFM (Invitrogen 17005-034) blended with epidermal growth factor (EGF) 0.25 ng/ml, pituitary extract (PE) 25 μg/ml (Invitrogen 3700015), Gentamycin 25 μm/ml (Sigma G1397).
  • Fibroblasts: DMEM (Invitrogen 21969035), blended with L-glutamine 2 mM (Invitrogen 25030024), Penicillin 50 Ul/ml/Streptomycin 50 μg/ml (Invitrogen 15070063), fetal calf serum 10% (FCS, Invitrogen 10270098).
  • Culturing took place for a period of 24 and 96 hours. At the end of the incubation period the cells were washed with PBS solution (Invitrogen 14190094).
  • The extraction of mRNA of each culture was achieved using TriReagent as per a standard protocol. The relevant cDNAs with 33P-labeled targets was produced by reverse transcription of mRNA using [α33P]-dATP and oligodT.
  • The labeled cDNA targets were hybridized to the specific cDNA probes covalently fixed to minichips. After thorough washing the relative amount of the hybridized targets was determined by means of the phosphor imaging method. This analysis was performed by measuring the radioactivity by means of a “Cyclone” Phosphor Imager (Packard Instruments; 72 hours exposure time) and using the ImageQuant TL-Software (Amersham Biosiences).
  • The following results were obtained:
    • Upregulation of the Cytosolic SOD-1 in Case of Keratinocytes
  • 24 h:
    • Control: 18.2
  • Treated with glucosylglycerol solution: 85
    96 h:
    • Control: 9.3
  • Treated with glucosylglycerol solution: 182
    • Upregulation of SOD-2 in Case of Fibroblasts
  • 24 h:
    • Control: 16.5
  • Treated with glucosylglycerol solution: 419
    96 h:
    • Control: 9.1
  • Treated with glucosylglycerol solution: 313

Claims (14)

What is claimed is:
1. A method of increasing expression of cell protective enzymes of a human having damaged skin and/or mucous membranes, for protection and stabilization of the human skin and/or mucous membranes, comprising treating the human skin and/or mucous membranes with glucosylglycerol and/or a glucosylglycerol ester so as to increase expression of a cell protective enzyme,
wherein the skin and membranes are damaged by reactive oxygen compounds, free radicals, chemicals, toxins, allergens, denaturing substances, substances attaching to DNA, substances damaging or deactivating proteins, or airborne particulate matter.
2. The method of claim 1, wherein the method is for the protection of human skin and/or mucous membrane against oxidative stress.
3. The method of claim 2, wherein the method is for the protection of human skin and/or mucous membranes against reactive oxygen compounds or free radicals.
4. The method of claim 1, wherein the method is for the protection of human skin and/or mucous membranes against chemicals, toxins, allergens, denaturing substances, substances attaching to DNA, substances damaging or deactivating proteins, or airborne particulate matter.
5. The method of claim 1, wherein the glucosylglycerol is 2-O-α-D-glucosylglycerol.
6. The method of claim 1, wherein the cell protective enzyme is an enzyme decomposing reactive oxygen compounds.
7. The method of claim 6, wherein the enzyme is a superoxide dismutase, a catalase or a glutathione peroxidase.
8. The method of claim 7, wherein the superoxide dismutase is SOD-1 or SOD-2.
9. The method of claim 1, wherein the cell protective enzyme is a DNA repairing enzyme.
10. The method of claim 9, wherein the cell protective enzyme is a ligase.
11. The method of claim 1, wherein the cell protective enzyme is a chaperone.
12. The method of claim 1, wherein the glucosylglycerol is provided in an aqueous solution.
13. The method of claim 1, wherein the concentration of glucosylglycerol ranges between 0.001% w/w and 10% w/w.
14. The method of claim 13, wherein the concentration of glucosylglycerol ranges between 0.01% w/w and 6% w/w.
US15/717,093 2008-08-22 2017-09-27 Use of glucosylglycerol Abandoned US20180015017A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US15/717,093 US20180015017A1 (en) 2008-08-22 2017-09-27 Use of glucosylglycerol

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE102008039231A DE102008039231A1 (en) 2008-08-22 2008-08-22 Use of glucosylglycerol
DE102008039231.6 2008-08-22
PCT/EP2009/006083 WO2010020424A2 (en) 2008-08-22 2009-08-21 Use of glucosylglycerol
US201113060122A 2011-04-27 2011-04-27
US15/717,093 US20180015017A1 (en) 2008-08-22 2017-09-27 Use of glucosylglycerol

Related Parent Applications (2)

Application Number Title Priority Date Filing Date
US13/060,122 Continuation US9867767B2 (en) 2008-08-22 2009-08-21 Use of glucosylglycerol
PCT/EP2009/006083 Continuation WO2010020424A2 (en) 2008-08-22 2009-08-21 Use of glucosylglycerol

Publications (1)

Publication Number Publication Date
US20180015017A1 true US20180015017A1 (en) 2018-01-18

Family

ID=41566715

Family Applications (2)

Application Number Title Priority Date Filing Date
US13/060,122 Active US9867767B2 (en) 2008-08-22 2009-08-21 Use of glucosylglycerol
US15/717,093 Abandoned US20180015017A1 (en) 2008-08-22 2017-09-27 Use of glucosylglycerol

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US13/060,122 Active US9867767B2 (en) 2008-08-22 2009-08-21 Use of glucosylglycerol

Country Status (7)

Country Link
US (2) US9867767B2 (en)
EP (1) EP2328545B1 (en)
JP (1) JP2012500781A (en)
DE (1) DE102008039231A1 (en)
ES (1) ES2551157T3 (en)
PL (1) PL2328545T3 (en)
WO (1) WO2010020424A2 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9089568B2 (en) * 2005-03-12 2015-07-28 Bitop Ag Method of using compatible solutes containing ectoine and/or hydroxyectoine
DE102008039231A1 (en) 2008-08-22 2010-02-25 Bitop Ag Use of glucosylglycerol
AU2012341425B2 (en) 2011-11-24 2017-03-02 Otsuka Pharmaceutical Factory, Inc. Protective agent for keratoconjunctiva or suppressive agent for keratoconjunctival disorder
JP6061474B2 (en) * 2012-02-17 2017-01-18 東洋精糖株式会社 Method for inhibiting denaturation and / or degradation of proteins by radicals
DE102012013482A1 (en) 2012-07-09 2014-01-09 Bitop Ag Composition for promoting the recovery of injured body tissue
JP2014058472A (en) * 2012-09-18 2014-04-03 Toyo Seito Kk Cosmetics for preventing skin aging
FR2997853B1 (en) * 2012-11-09 2016-11-04 Oreal USE OF EXTRACT OF MYROTHAMNUS FLABELLIFOLIA AND RHAMNOSE TO COMBAT THE SIGNS OF SKIN AGING.
JP6077899B2 (en) * 2013-03-21 2017-02-08 サッポロビール株式会社 Acetaldehyde dehydrogenase inhibitor
US10543158B2 (en) 2017-04-17 2020-01-28 W Skincare, LLC Autophagy activating complex, compositions and methods
CN109998937B (en) * 2019-03-22 2021-06-29 南京工业大学 Series of cosmetics containing glycerol glucoside (αGG) and preparation method thereof
JP2020158449A (en) * 2019-03-27 2020-10-01 東洋精糖株式会社 Glutathione reductase expression promoter, antioxidant capacity improver
JPWO2020196484A1 (en) * 2019-03-28 2020-10-01

Family Cites Families (52)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4261995A (en) 1979-08-31 1981-04-14 Syntex (U.S.A.) Inc. 4-Phenyl-and 5-phenyl-1,4,5,6-tetrahydropyrimidine derivatives
EP0053754B1 (en) 1980-12-06 1986-04-23 Reichert, Dietrich, Dr. med. Drug for antagonizing snore, and method for its application
DE3635522A1 (en) 1986-10-18 1988-04-28 Euro Celtique Sa PHARMACEUTICAL COMPOSITION
SE467340B (en) 1990-07-04 1992-07-06 Perstorp Ab USE OF INOSITOL MONOPHOSPHATE FOR THE PREPARATION OF AN EFFECTIVE EFFECT AS A NEUROPEPTID Y (NPY) ANTAGONIST
FR2674434B1 (en) 1991-03-27 1993-06-18 Nativelle Sa Ets NOVEL PHARMACEUTICAL COMPOSITION BASED ON TAURIN FOR INHALATION ADMINISTRATION.
IL100810A (en) 1992-01-30 1996-12-05 Yeda Res & Dev Pharmaceutical compositions comprising 2-methyl-4-carboxy-5-hydroxy-tetrahydropyrimidine and/or 2-methyl-4-carboxy-tetrahydropyrimidine methods for the isolation and purification of said compounds and substantially pure 2-methyl-4-carboxy-5-hydroxy-3, 4, 5, 6-tetrahydropyrimidine salts 5-ethers and 5-esters thereof
IL101056A (en) 1992-02-24 1997-03-18 Res & Dev Co Ltd Composition for nasal treatment
US5834473A (en) 1993-04-29 1998-11-10 Cultor, Ltd. Method for treating coccidiosis
DE4342560A1 (en) 1993-12-14 1995-06-22 Marbert Gmbh Use of 1,4,5,6-tetra:hydro-4-pyrimidine carboxylic acid derivs. in cosmetics
DE19540749A1 (en) 1995-11-02 1997-05-07 Beiersdorf Ag Cosmetic preparations with an effective content of glycosylglycerides
US5880098A (en) * 1996-04-12 1999-03-09 Pharmacia & Upjohn Aktiebolag Therapeutic treatment
PT101887A (en) 1996-06-28 1998-01-30 Inst De Biolog Ex E Tecnologic USES OF 2-0-MANOSILGLICERATE FOR THERMOESTABILIZATION, OSMOPROTECTION AND PROTECTION AGAINST ENZYME DEHYDRATION, OTHER CELL COMPONENETES AND CELLS
DE19634021A1 (en) * 1996-08-23 1998-02-26 Beiersdorf Ag Microbial adhesion inhibitor comprising glyco:glycero:lipid
US20010056068A1 (en) 1998-03-04 2001-12-27 Kristof Chwalisz Method of treatment and prevention of nitric oxide deficiency-related disorders with citrulline and citrulline derivatives
AU750027B2 (en) 1998-08-01 2002-07-11 Merck Patent Gmbh Use of ectoine or ectoine derivatives in cosmetic formulations
US6080401A (en) 1998-11-19 2000-06-27 Reddy; Malireddy S. Herbal and pharmaceutical drugs enhanced with probiotics
HK1042825A1 (en) 1998-12-22 2002-08-30 The University Of North Carolina At Chapel Hill Compounds and methods for the treatment of airway diseases and for the delivery of airway drugs
ES2204640T3 (en) 1999-06-12 2004-05-01 Bitop Aktiengesellschaft Fur Biotechnische Optimierung PHARMACEUTICAL PREPARED WITH PROTEIN CONTENT.
EP1272201B1 (en) 2000-04-12 2004-11-24 Bitop Aktiengesellschaft Für Biotechnische Optimierung Use of compatible solutes as substances having free radical scavenging properties
US6716819B2 (en) 2000-05-19 2004-04-06 University Of Iowa Research Foundation Use of xylitol to reduce ionic strength and activate endogenous antimicrobials for prevention and treatment of infections
US20040028631A1 (en) 2000-08-18 2004-02-12 Thomas Schwarz Cosmetic formulations
US7048910B2 (en) 2000-09-07 2006-05-23 Merck Patent Gmbh Use of ectoine or ectoine derivatives for oral care
US20020151541A1 (en) 2000-10-31 2002-10-17 Michel Pairet Pharmaceutical compositions containing tiotropium salts and antihistamines and their use
FR2819411B1 (en) 2001-01-18 2003-02-21 Oreal IRIDESCENT COSMETIC COMPOSITION AND USES THEREOF
FR2826011B1 (en) 2001-06-14 2004-12-10 Oreal NOVEL 7-OXO-DHEA DERIVATIVES AND COSMETIC USE
DE10133202A1 (en) 2001-07-07 2003-01-16 Beiersdorf Ag Topical compositions containing osmolytes, useful e.g. for treating or preventing dry skin or inflammatory conditions of the skin, e.g. eczema, polymorphic light dermatosis or psoriasis
FR2832156B1 (en) 2001-11-15 2004-05-28 Oreal PREPARATION OF POLYSACCHARIDE BETAINATE COMPOUNDS, COMPOUNDS OBTAINED, THEIR USE AND COMPOSITIONS COMPRISING THE SAME
US6485711B1 (en) 2002-03-21 2002-11-26 Michael J. Olmstead Organic toothpaste containing saponin
DE10240923A1 (en) 2002-09-02 2004-03-04 Merck Patent Gmbh Flavonoid derivatives for eczema treatment
WO2004024187A2 (en) 2002-09-13 2004-03-25 Zicam, Llc. Compositions to reduce congestion and methods for application thereof to the nasal membrane
JP2004331583A (en) * 2003-05-08 2004-11-25 Noevir Co Ltd Skin cleanser
JP4307148B2 (en) * 2003-05-08 2009-08-05 株式会社ノエビア Cell activator
JP4039567B2 (en) * 2003-05-08 2008-01-30 株式会社ノエビア Aqueous cosmetics
DE10330243A1 (en) 2003-07-03 2005-01-20 bitop Aktiengesellschaft für biotechnische Optimierung Use of osmolytes derived from extremophilic bacteria for the manufacture of medicines for the external treatment of atopic dermatitis
DE10330768A1 (en) 2003-07-07 2005-02-24 bitop Aktiengesellschaft für biotechnische Optimierung Use of osmolytes obtained from extremophilic bacteria for the preparation of inhalable medicaments for the prophylaxis and treatment of pulmonary and cardiovascular diseases, and an inhalation device containing osmolyte as an active ingredient
EP1694293A2 (en) 2003-11-29 2006-08-30 Passion For Life Healthcare Limited Composition and delivery system comprising multilayered microparticles
DE102004049062A1 (en) 2004-03-30 2005-10-13 bitop Aktiengesellschaft für biotechnische Optimierung Topical preparation for application on the skin containing natural oil of the evening primrose (Oenothera biennis) (= Oleum Oenothera) and osmolytes from extremophilic microorganisms
KR20070110087A (en) 2005-02-23 2007-11-15 알자 코포레이션 Nasal administration of active agents to the central nervous system
US9089568B2 (en) 2005-03-12 2015-07-28 Bitop Ag Method of using compatible solutes containing ectoine and/or hydroxyectoine
DE102005023639A1 (en) * 2005-05-19 2006-11-23 Beiersdorf Ag Active substance combination, useful for skin moisturizing and for stabilizing skin barrier, comprises glucosylglycerides, boundary surface-active glucose derivatives and boundary surface-active oligoglycerine derivatives
DE102005023636A1 (en) * 2005-05-19 2006-11-23 Beiersdorf Ag Active ingredient combinations of glucosylglycerides and creatine and / or creatinine
DE102005023640A1 (en) * 2005-05-19 2006-11-23 Beiersdorf Ag Active substance combination, useful for skin moisturizing and stabilization of skin barrier, comprises glucosylglycerides and partially neutralized esters of monoglyceride and/or diglyceride fatty acids with citronic acids
WO2007124991A1 (en) * 2006-04-27 2007-11-08 Beiersdorf Ag Cosmetic preparation with aquaporin stimulators and the use thereof
JP2008024622A (en) * 2006-07-20 2008-02-07 Noevir Co Ltd Collagen type iv production promoter and basement membrane enhancer
AT504347B8 (en) * 2006-09-21 2008-09-15 Univ Graz Tech PROCESS FOR THE PREPARATION OF GLUCOSE DERIVATIVES
DE102006055041A1 (en) * 2006-11-17 2008-05-21 Beiersdorf Ag Cosmetic formulation with glucosylglycerides and cationic emulsifiers
DE102006056766A1 (en) 2006-12-01 2008-06-05 Bitop Ag Use of compatible solutes
DE102007040615A1 (en) 2007-08-27 2009-03-05 Bitop Ag Osmolyte for the treatment of allergic or viral respiratory diseases
DE102007052380A1 (en) 2007-10-31 2009-05-07 Bitop Ag Osmolyte-containing preparations for use in dry mucous membranes
DE102008039231A1 (en) 2008-08-22 2010-02-25 Bitop Ag Use of glucosylglycerol
DE102008053549A1 (en) 2008-10-28 2010-04-29 Bitop Ag Glucosylglycerol containing composition
DE102011113059A1 (en) 2011-09-09 2013-03-14 Bitop Ag Therapeutic Applications of Ectoin

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Yamamura JP2004331583, published on November 25, 2004 and provided with certified English translation here for citation, hereinafter referred to as �583, see attached English translation dated in January 2016 *

Also Published As

Publication number Publication date
EP2328545B1 (en) 2015-08-05
DE102008039231A1 (en) 2010-02-25
US9867767B2 (en) 2018-01-16
WO2010020424A2 (en) 2010-02-25
JP2012500781A (en) 2012-01-12
WO2010020424A3 (en) 2010-04-29
ES2551157T3 (en) 2015-11-16
US20110207681A1 (en) 2011-08-25
EP2328545A2 (en) 2011-06-08
PL2328545T3 (en) 2016-04-29

Similar Documents

Publication Publication Date Title
US9867767B2 (en) Use of glucosylglycerol
CN109414398B (en) Antioxidant composition for skin
US20200155444A1 (en) Yeast-based masks for improved skin, hair and scalp health
KR20130008081A (en) Cosmetic composition comprising an extract of the leaves of castanea sativa
JP6868724B2 (en) Peptides showing melanin production promoting activity and their uses
KR102386995B1 (en) Cosmetic composition containing Artemisia Capillaris extracts prepared by a method based on natural deep eutectic solvents
EP3144316A1 (en) Peptide having efficacy for remedying hypopigmentation and inhibiting adipogenesis, and use of same
ES2741874T3 (en) Use of Tiliacora triandra in cosmetics and compositions thereof
JP4975412B2 (en) Moisturizer for skin and external preparation for skin
KR20110083480A (en) Free radical scavengers, radical scavengers and oxidative cell disorder inhibitors
JP5856847B2 (en) Skin external preparation composition containing Matsune extract
JP4413387B2 (en) Collagen production promoter, elastase activity inhibitor, collagenase activity inhibitor and skin cosmetic
US11925702B2 (en) Methods for extracting compound from ginseng, ginseng extract comprising the compound and composition for enhancing skin barrier comprising the same
KR100544034B1 (en) Anti-aging cosmetic composition containing vergenin
KR20210036803A (en) Cosmetic composition for preventing skin aging and improving skin winkle comprising extracts of Selaginella rossii
US12357559B2 (en) Cosmetic composition for preventing skin aging and reducing skin wrinkles, comprising Viburnum stellato-tomentosum extract
KR101640735B1 (en) Composition for improving skin wrinkle
KR101784331B1 (en) 6,7-dimethoxy-2,2-dimethyl-2H-chromene for increasing the expression of Aquaporin-3 and uses thereof
KR101640736B1 (en) Composition for improving skin wrinkle
KR102869149B1 (en) Composition for skin moisturizing comprising rose flower extract extracted with skin cosmetic solution as a solvent
KR101526592B1 (en) Composition for improving skin wrinkles
KR20210004126A (en) A composition comprising a peptide sequence of a domain having DNA damage repair and skin damage repair effect in human ribosomal protein S3
KR20260010707A (en) Active peptides and their compositions and uses
KR20240047006A (en) Cosmetic composition for antioxidant or whitening containing Eckmaxol as an active ingredient
ES2715761T3 (en) Galactolipid for use in healing and in the prevention and / or treatment of skin aging

Legal Events

Date Code Title Description
AS Assignment

Owner name: BITOP AG, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KRUGER, JULIA;STUMM, GERHARD;SIGNING DATES FROM 20171109 TO 20171113;REEL/FRAME:044456/0799

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION