US20080242849A1 - Wrinkle-Diminishing Agent - Google Patents
Wrinkle-Diminishing Agent Download PDFInfo
- Publication number
- US20080242849A1 US20080242849A1 US10/586,877 US58687705A US2008242849A1 US 20080242849 A1 US20080242849 A1 US 20080242849A1 US 58687705 A US58687705 A US 58687705A US 2008242849 A1 US2008242849 A1 US 2008242849A1
- Authority
- US
- United States
- Prior art keywords
- skin
- wrinkles
- eugenyl
- wrinkle
- glycoside
- 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
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
-
- 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
- A61Q19/08—Anti-ageing preparations
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- 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
Definitions
- the present invention relates to an antiwrinkle agent comprising an eugenyl glycoside having excellent wrinkle alleviating effect on the wrinkles formed due to aging, especially on exposed skin portions, and being capable of keeping skins healthy from the viewpoint of dermatology and beauty.
- organs gradually deteriorate after they are born and as they grow old, and the functions of some of them stop later and the number of the organs of which functions have stopped reaches a certain value or more, resulting in a death.
- a process in which the functions gradually deteriorate is called aging.
- Skins are affected directly by their environments, and have an important function to maintain the conditions inside a living body and hence all functions of the skins rarely stop, but the skin is an organ likely to remarkably show signs of aging, such as wrinkles or spots, being of dull color, or being loose, which are marked especially at skin portions exposed to daylight.
- retinoic acid As a substance having a wrinkle alleviating effect on the wrinkles caused by the photoaging, retinoic acid is used as a prescription drug in the United States, but the retinoic acid has a strong side effect and has a problem from the viewpoint of safety, and hence it has not yet been approved in Japan. Further, as substances for alleviating the wrinkles, retinol (vitamin A) which is believed that it is absorbed by a body and then converted to retinoic acid to exhibit the effect, ascorbic acid (vitamin C) having an antioxidant action and a collagen synthesis promotion effect, and tocopherol (vitamin E) having a strong antioxidant action have been proposed (see, for example, Japanese Unexamined Patent Publication Nos. Hei 7-165567 and Sho 62-164609), but these substances disadvantageously do not have a satisfactory effect. Therefore, a satisfactorily effective and safe substance for diminishing the wrinkles has not yet been developed.
- Eugenol is known as a fragrance component of clove which is a kind of spice, and it is known that the eugenol is generally used as an analgesic agent for toothache and others, and further has a blood flow promotion effect or demelanizing effect when applied to a surface topical site, and it is applied to a dermis collagen fascicular reconstruction agent (see, for example, Japanese Unexamined Patent Publication Nos. Hei 9-249549, Hei 6-227959, and 2002-104921).
- the eugenol has problems in that it has a characteristic odor and that it induces sensitization when used in a high concentration (see, for example, Contact Dermatitis, 1992, No. 27, p. 98-104).
- the present inventors have found that a glycoside formed from eugenol can solve these problems, and have proposed a hair tonic and a sustained-release aromatic composition for human surface skin (see Japanese Unexamined Patent Publication Nos. Hei 9-40531 and Hei 7-179328), but they have made no studies on a wrinkle alleviating effect of the glycoside of eugenol.
- the present inventors have conducted extensive and intensive studies mainly on eugenol derivatives.
- the antiwrinkle agent comprising an eugenyl glycoside is advantageous not only in that it can keep skins healthy from the viewpoint of beauty, but also in that it has excellent wrinkle alleviating effect on the wrinkles formed due to aging, especially on exposed skin portions, and thus the present invention has been completed.
- the present invention is directed to an antiwrinkle agent comprising an eugenyl glycoside. Further, the present invention is directed to the antiwrinkle agent wherein the eugenyl glycoside is eugenyl- ⁇ -D-glucoside.
- an antiwrinkle agent which is advantageous not only in that it has excellent wrinkle alleviating effect on the wrinkles formed due to aging, especially on exposed skin portions, but also in that it keeps skins healthy from the viewpoint of dermatology and beauty.
- Eugenol is generally known as a fragrance component of clove which is a kind of spice. It is known that the eugenol has an analgesic effect, and it is also used as an analgesic agent for toothache and others.
- the eugenyl glycoside in the present invention can be obtained by forming a glycoside from eugenol with an O-glycoside bond by a general method.
- the glycosyl residue of the eugenyl glycoside in the present invention is monosaccharide or oligosaccharide, and examples include monosaccharides such as glucose, galactose, xylose, rhamnose, mannose, glucosamine, and galactosamine; and disaccharides such as lactose, maltose, sucrose, cellobiose and gentiobiose. Preferred are glucose, galactose, xylose, lactose and maltose.
- a glycoside has isomers having an ⁇ -bond or a ⁇ -bond.
- either any isomer or a mixture of the isomers can be used, but preferred is a glycoside having a ⁇ -bond.
- eugenyl- ⁇ -D-glucoside, a D-glucose glycoside of eugenol having a ⁇ -bond is especially preferably used from the viewpoint of obtaining the effect.
- the amount of the eugenyl glycoside formulated is 0.2 to 5.0% by weight (hereinafter, “%” is given by weight unless otherwise specified), based on the total weight of the antiwrinkle agent.
- % is given by weight unless otherwise specified
- the amount is more preferably 0.3 to 5.0%, further preferably 0.5 to 4.5%, especially preferably 1.0 to 4.0%.
- the antiwrinkle agent of the present invention can be formulated in cosmetics for skin, external drug preparation or bath salts, and can be used in the form of, for example, lotion, emulsion, cream or pack.
- a coloring agent, a fragrance, a preservative, a surfactant, a pigment or an antioxidant can be added in such an amount that the effect of the present invention is achieved.
- the wrinkle alleviating effect of the antiwrinkle agent of the present invention when applied to a skin which had suffered from photoaging was examined by the following test method.
- Comparative Example 1 only the base was used, and in Comparative Example 2, eugenol was added in the concentration shown in Table 1.
- Photoaging was caused by irradiating the mice with UVA and UVB once a day and five times per week for continuous eight weeks.
- a UVA dose of 20 J/cm 2 was increased to 25 J/cm 2 and then 30 J/cm 2 every week, and a UVB dose of 20 mJ/cm 2 was increased to 30 mJ/cm 2 and then 40 mJ/cm 2 every week, and the respective maximum doses were used on and after the third week.
- the wrinkle alleviating effect was evaluated in respect of the wrinkle score, the dermis collagen content and the epidermis thickness.
- the state of wrinkles was rated in accordance with the method of Bissett et. al. (Photochem Photobiol 46:367-378, 1987). Specifically, the wrinkles were macroscopically evaluated with respect to the size and depth and rated in 4 stages: “large and deep wrinkles can be recognized” was rated 3, “some wrinkles can be recognized” was rated 2, “any wrinkles cannot be recognized” was rated 1, and “normal and fine skin is observed” was rated 0.
- Example 1 (0.2% by weight of eugenyl- ⁇ -D- 2.4 ⁇ 0.1 glucoside) applied
- Example 2 (2.0% by weight of eugenyl- ⁇ -D- 2.2 ⁇ 0.2 glucoside) applied
- Example 3 (4.0% by weight of eugenyl- ⁇ -D- 2.1 ⁇ 0.1 glucoside) applied
- Comparative Example 1 (base only) applied 2.6 ⁇ 0.1 Comparative Example 2 (2.0% by weight of 2.7 ⁇ 0.1 eugenol) applied *
- Value is average ⁇ standard error.
- the wrinkle scores are shown in Table 1.
- the wrinkle scores of the antiwrinkle agent applied groups in Examples 1 to 3 are significantly low as compared to that in Comparative Example 1, which indicates that the antiwrinkle agent comprising the eugenyl glycoside is effective against the wrinkles caused due to the photoaging. Further, the antiwrinkle agent comprising eugenol in Comparative Example 2 did not show the antiwrinkle effect in the wrinkle score.
- the results of the measurements of the collagen content (hydroxyproline content) and the epidermis thickness are shown in Table 2.
- the collagen content of the antiwrinkle agent applied groups in Examples 1 to 3 was that significantly high as compared to in Comparative Example 1, which indicates that the eugenyl glycoside is effective against the reduction of the dermis collagen content due to the photoaging. Further, the antiwrinkle agent comprising eugenol in Comparative Example 2 did not show the effect on the reduction of the dermis collagen content due to the photoaging.
- the epidermis thickness of the antiwrinkle agent applied groups in Examples 1 to 3 was significantly thin as compared to that in Comparative Example 1, which indicates that the eugenyl glycoside is effective in inhibiting the increase of epidermis thickness due to the photoaging.
- the antiwrinkle agent comprising eugenol in Comparative Example 2 did not show the effect of inhibiting the increase of epidermis thickness due to the photoaging.
- retinoic acid of which the wrinkle alleviating effect has been confirmed, was applied to the present evaluation system, it was found that retinoic acid was effective with respect to the wrinkle score and collagen content, but retinoic acid increased the epidermis thickness. This action of retinoic acid to increase the epidermis thickness is one of problems for safety.
- the eugenyl glycoside had no such an action, and had no problems in a general safety test.
- Skin lotions having the compositions shown below were individually prepared by the method described below, and the lotions prepared as samples were evaluated with respect to the wrinkle alleviating effect in accordance with the following procedure.
- Five healthy persons (women; age: 44 to 55) having wrinkles at the corners of their eyes were selected as subjects, and they individually applied about 0.2 ml of each of the skin lotions in Example 4 and Comparative Example 3 to the respective portions of wrinkles at the corners of the left eye and the right eye (about 4 cm 2 or 2 cm ⁇ 2 cm around the corner of the eye per sample) after washing the face in the morning and after bathing in the evening, i.e., twice a day for continuous two months (sixty days). After the final application, they filled in a questionnaire about the conditions of the skins (wrinkles) at the corners of their left and right eyes.
- Ingredients Amount(%) Ingredient A (1) Olive oil 10.0 (2) Isopropyl myristate 1.0 (3) Polyoxyethylene (20) 0.5 sorbitan monolaurate (4) Propylene glycol 1.0 (5) Glycerol 2.0 Ingredient B (6) Methylparaben 0.1 (7) Ethanol 7.0 (8) Purified water Balance Ingredient C (9) Eugenyl- ⁇ -D-glucoside 2.0 (Example 4) or 0 (Comparative Example 3)
- the skin lotion in Example 4 considerably alleviated the wrinkles, as compared to that in Comparative Example 3, and further it improved the softness or color tone of the skin which deteriorated due to the photoaging.
- the skin lotion in the present invention caused no skin troubles, e.g., no stimulation or no itching.
- a skin cream containing eugenyl- ⁇ -D-glucoside and having the composition shown below was prepared by the method described below, and twenty healthy persons (women; age: 50 to 55), who preliminarily answered that they had skin troubles of wrinkles at the corners of their eyes, used the skin cream for one week or longer and then filled in a questionnaire.
- Ingredients Amount(%) Ingredient A (1) Bees wax 2.0 (2) Stearic acid 5.0 (3) Stearyl alcohol 5.0 (4) Reduced lanolin 2.0 (5) Squalene 20.0 (6) Sorbitan monostearate 3.0 (7) Polyoxyethylene (20) 3.0 sorbitan monostearate (8) Propylene glycol 5.0 Ingredient B (9) Methylparaben 0.2 (10) Purified water Balance Ingredient C (11) Eugenyl- ⁇ -D-glucoside 2.0
- Example 5 After the subjects individually used the skin cream in Example 5 for one week or longer, they filled in a questionnaire about the state of wrinkles in the items shown below. The numbers of the persons who answered that the description in each item was true after using the skin cream are shown below.
- the antiwrinkle agent of the present invention can be formulated in cosmetics for skin, external drug preparation or bath salts, and can be used in the form of, for example, lotion, emulsion, cream or pack, and it is very useful from the viewpoint of skin beauty.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Emergency Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/465,780 US8273719B2 (en) | 2004-01-21 | 2009-05-14 | Wrinkle-diminishing agent |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004012764A JP5244284B2 (ja) | 2004-01-21 | 2004-01-21 | シワ改善剤 |
JP2004-012764 | 2004-01-21 | ||
PCT/JP2005/000736 WO2005070387A1 (ja) | 2004-01-21 | 2005-01-21 | シワ改善剤 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2005/000736 A-371-Of-International WO2005070387A1 (ja) | 2004-01-21 | 2005-01-21 | シワ改善剤 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/465,780 Division US8273719B2 (en) | 2004-01-21 | 2009-05-14 | Wrinkle-diminishing agent |
Publications (1)
Publication Number | Publication Date |
---|---|
US20080242849A1 true US20080242849A1 (en) | 2008-10-02 |
Family
ID=34805355
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US10/586,877 Abandoned US20080242849A1 (en) | 2004-01-21 | 2005-01-21 | Wrinkle-Diminishing Agent |
US12/465,780 Expired - Fee Related US8273719B2 (en) | 2004-01-21 | 2009-05-14 | Wrinkle-diminishing agent |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/465,780 Expired - Fee Related US8273719B2 (en) | 2004-01-21 | 2009-05-14 | Wrinkle-diminishing agent |
Country Status (7)
Country | Link |
---|---|
US (2) | US20080242849A1 (ja) |
EP (1) | EP1712217A4 (ja) |
JP (1) | JP5244284B2 (ja) |
KR (1) | KR100797664B1 (ja) |
CN (1) | CN1909880B (ja) |
TW (1) | TWI328461B (ja) |
WO (1) | WO2005070387A1 (ja) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030054021A1 (en) * | 2001-06-14 | 2003-03-20 | Maria Dalko | 7-oxo-DHEA compounds for treating keratinous conditions/afflictions |
US20030165547A1 (en) * | 2001-05-18 | 2003-09-04 | Elisabeth Picard-Lesboueyries | Cosmetic uses of 3beta-acetoxy-7-oxo-DHEA |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0678223B2 (ja) | 1986-01-14 | 1994-10-05 | 鐘紡株式会社 | 皮膚化粧料 |
JPH06227959A (ja) * | 1993-02-01 | 1994-08-16 | Yakult Honsha Co Ltd | メラニン生成抑制剤および皮膚化粧料 |
FR2710841B1 (fr) | 1993-10-05 | 1995-11-17 | Oreal | Composition cosmétique ou pharmaceutique pour la peau, anhydre et stable, à base de rétinol et son utilisation en vue du traitement des maladies de la peau. |
JP3304219B2 (ja) | 1993-11-11 | 2002-07-22 | カネボウ株式会社 | 人体表面用徐放性芳香組成物 |
JP3162962B2 (ja) * | 1995-07-27 | 2001-05-08 | カネボウ株式会社 | 養毛料 |
JPH09249549A (ja) * | 1996-03-18 | 1997-09-22 | Lion Corp | 化粧料組成物 |
JP2000169358A (ja) * | 1998-12-07 | 2000-06-20 | Mikimoto Pharmaceut Co Ltd | 化粧料、医薬部外品、医薬品、食品 |
JP4025487B2 (ja) * | 2000-05-19 | 2007-12-19 | 花王株式会社 | 抗炎症剤 |
JP2002104921A (ja) * | 2000-09-29 | 2002-04-10 | Pola Chem Ind Inc | 真皮コラーゲン線維束再構築剤及びそれを含有する組成物 |
JP4789334B2 (ja) * | 2001-03-01 | 2011-10-12 | ポーラ化成工業株式会社 | シワ改善及び予防対応用皮膚外用剤 |
FR2824737A1 (fr) * | 2001-05-18 | 2002-11-22 | Oreal | Utilisations cosmetiques de la 3beta-acetoxy-7-oxo dhea |
JP4162898B2 (ja) * | 2002-01-31 | 2008-10-08 | 株式会社ファンケル | ラミニン5産生促進剤およびインテグリンα6β4産生促進剤を含む組成物 |
JP2004107250A (ja) * | 2002-09-18 | 2004-04-08 | Kanebo Ltd | 敏感肌改善剤、神経成長因子生成抑制剤及び敏感肌改善用皮膚外用組成物 |
-
2004
- 2004-01-21 JP JP2004012764A patent/JP5244284B2/ja not_active Expired - Fee Related
-
2005
- 2005-01-21 CN CN2005800026000A patent/CN1909880B/zh not_active Expired - Fee Related
- 2005-01-21 KR KR1020067016681A patent/KR100797664B1/ko active IP Right Grant
- 2005-01-21 TW TW094101885A patent/TWI328461B/zh not_active IP Right Cessation
- 2005-01-21 WO PCT/JP2005/000736 patent/WO2005070387A1/ja active Application Filing
- 2005-01-21 US US10/586,877 patent/US20080242849A1/en not_active Abandoned
- 2005-01-21 EP EP05703964A patent/EP1712217A4/en not_active Withdrawn
-
2009
- 2009-05-14 US US12/465,780 patent/US8273719B2/en not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20030165547A1 (en) * | 2001-05-18 | 2003-09-04 | Elisabeth Picard-Lesboueyries | Cosmetic uses of 3beta-acetoxy-7-oxo-DHEA |
US20030054021A1 (en) * | 2001-06-14 | 2003-03-20 | Maria Dalko | 7-oxo-DHEA compounds for treating keratinous conditions/afflictions |
Also Published As
Publication number | Publication date |
---|---|
CN1909880B (zh) | 2011-07-06 |
CN1909880A (zh) | 2007-02-07 |
TW200524634A (en) | 2005-08-01 |
US8273719B2 (en) | 2012-09-25 |
TWI328461B (en) | 2010-08-11 |
EP1712217A4 (en) | 2008-07-09 |
WO2005070387A1 (ja) | 2005-08-04 |
KR100797664B1 (ko) | 2008-01-23 |
KR20060127981A (ko) | 2006-12-13 |
EP1712217A1 (en) | 2006-10-18 |
US20090227525A1 (en) | 2009-09-10 |
JP5244284B2 (ja) | 2013-07-24 |
JP2005206480A (ja) | 2005-08-04 |
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Owner name: KAO CORPORATION, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:IKEMOTO, TAKESHI;KOMIYA, AYA;HARATAKE, AKINORI;REEL/FRAME:018096/0166 Effective date: 20060703 |
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Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |