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WO2006068254A1 - Agent de blanchiment de la peau - Google Patents

Agent de blanchiment de la peau Download PDF

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Publication number
WO2006068254A1
WO2006068254A1 PCT/JP2005/023680 JP2005023680W WO2006068254A1 WO 2006068254 A1 WO2006068254 A1 WO 2006068254A1 JP 2005023680 W JP2005023680 W JP 2005023680W WO 2006068254 A1 WO2006068254 A1 WO 2006068254A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
whitening
whitening agent
methyl group
chemical
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/JP2005/023680
Other languages
English (en)
Japanese (ja)
Inventor
Yoshihide Suwa
Seiichi Koshimizu
Haruo Nukaya
Kenji Oguchi
Yoshinori Nozawa
Yukihiro Akao
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.)
GIFU RESEARCH AND DEVELOPMENT FOUNDATION
Suntory Ltd
Gifu International Institute of Biotechnology
Original Assignee
GIFU RESEARCH AND DEVELOPMENT FOUNDATION
Suntory Ltd
Gifu International Institute of Biotechnology
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 GIFU RESEARCH AND DEVELOPMENT FOUNDATION, Suntory Ltd, Gifu International Institute of Biotechnology filed Critical GIFU RESEARCH AND DEVELOPMENT FOUNDATION
Priority to CN2005800447813A priority Critical patent/CN101102744B/zh
Priority to JP2006549073A priority patent/JP5095221B2/ja
Publication of WO2006068254A1 publication Critical patent/WO2006068254A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61K31/075—Ethers or acetals
    • A61K31/085—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon
    • A61K31/09—Ethers or acetals having an ether linkage to aromatic ring nuclear carbon having two or more such linkages
    • 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
    • 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
    • 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
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin

Definitions

  • the present invention relates to a whitening agent, and in particular, to prevent or treat the formation (deposition) of black (melanin) pigment, which is also the cause of the occurrence of skin spots, freckles, etc.
  • the present invention relates to a whitening agent that uses rio-resinol, which is effective in promoting reduction, as a whitening active ingredient.
  • the action of tyrosinase is inhibited, and the activity of melanocytes by melanocyte-stimulating hormone produced in the skin by Z or ultraviolet rays is inhibited, thereby producing a black (melanin) pigment.
  • It relates to foods, beverages, cosmetics and pharmaceuticals that have the ability to suppress and promote the reduction of the deposited pigment.
  • Skin Blemish 'Sobacus is regarded as a serious skin problem.
  • stains and freckles, and black pigmentation on the skin after tanning occur and increase with age and become disappeared, which is an inevitable problem for middle-aged and elderly people.
  • Most of the black pigment deposited on the skin is considered to be melanin, which is produced in melanin granules (melanosomes) in melanocytes (melanocytes) between the epidermis and dermis. It is said that it diffuses to neighboring cells by osmotic action.
  • Patent Document 1 those relating to ellagic acid (see Patent Document 1), ascorbic acid and ascorbic acid derivatives (see Patent Document 2), which mainly reduce blackish melanin by reducing melanin.
  • Kojic acid see patent document 3
  • hydroquinone see non-patent document 1
  • aractin which acts directly on melanin cells to inhibit tyrosinase activity and inhibit melanin production to suppress darkness
  • Others such as those that promote metabolism and excrete melanin pigments outside the body, such as placenta extract (placenta extract), are known (see Patent Document 4).
  • HI_MSH melanocyte stimulating hormone
  • (+)-Lioniresinol and / or (-)-Lioniresinol are known as compounds having antibacterial action, antioxidant action, and aroma enhancing action (see Patent Document 6), and antibacterial makeup. It is used as a fee (see Patent Document 7).
  • rio-resinol glycoside has an epidermal cell growth promoting action, it is also used as an anti-oxidant effect and a cosmetic for preventing aging (wrinkle, rough skin) using its performance (Patent Document) 8).
  • it is known to have various antioxidant activities such as lipid peroxide production inhibition, radical scavenging activity, oxygen radical scavenging activity.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 64-79103
  • Patent Document 2 JP-A-2-45408
  • Patent Document 3 JP-A-53-3538
  • Patent Document 4 Japanese Patent Laid-Open No. 8-104616
  • Patent Document 5 Republished WO2004 / 017980
  • Patent Document 6 Japanese Unexamined Patent Publication No. 2003-128568
  • Patent Document 7 JP-A-10-139601
  • Patent Document 8 Japanese Patent Laid-Open No. 10-236940
  • Patent Document 9 Japanese Patent Laid-Open No. 11-2555639
  • Non-Patent Document 1 JAMA., No. 194, p. 965-967, 1965
  • Non-Patent Document 2 J. Cell Sci., 105, p. 1079-1084, 1993
  • Non-Patent Document 3 J. Cell Sci., 107, p. 205-211, 1994
  • Non-Patent Document 4 Anal. Biochem., 159, p. 191-197, 1986
  • Non-Patent Document 5 Pro Natl. Acad. Sci. USA, 92nd, p. 1792-1793, 1995
  • Non-Patent Document 6 Biochem. Biophys. Acta., Pp. 1313, p. 130-138, 1996
  • Non-Patent Document 7 British J. Darmatol, p. 139, p. 216-224, 1998 Disclosure of the Invention
  • the present invention provides a whitening agent having an excellent whitening effect even at a low blending amount, which provides a compound having excellent safety such as skin irritation and excellent stability. It provides food, drink, cosmetics and pharmaceuticals to facilitate ingestion or administration.
  • (+) rio diresinol has a high inhibitory action on melanocyte activation by a-MSH
  • (1) rio diresinol has a tyrosinase activity inhibitory action. It has been found that a mixture of (+)-rioniresinol and (1) rioniresinol, which is a whitening material having different mechanisms of action, is useful as a whitening agent, suppressing or preventing melanin formation. The invention has been completed.
  • the present invention provides:
  • the whitening agent according to the above (1) characterized in that it is rioniresinol represented by
  • Whitening active ingredient strength Whitening agent according to (1) or (2) characterized by having an inhibitory action on S-melanin production
  • a cosmetic, food or drink, or pharmaceutical comprising at least one compound described in (1) or (2) as a whitening active ingredient
  • a method of whitening the skin which comprises administering to a mammal a whitening agent containing at least one of rio-resinols represented by the formula:
  • (+)-rio diresinol represented by:
  • the whitening agent provided by the present invention inhibits or suppresses the action of tyrosinase, which is the first step in the above-mentioned cause of melanogenesis, and melanocyte-stimulating hormone (hypertensive hormone) produced in the skin by Z or ultraviolet rays.
  • melanocyte-stimulating hormone hypertensive hormone
  • Inhibiting the activity of melanocytes by (MSH) suppresses the production of the melanin pigment itself and at the same time reduces the amount of the pigment deposited.
  • a whitening material with a different mechanism of action that is, having a tyrosinase activity inhibitory action (1) a mixture of lio diresinol and melanocyte activity inhibitory action (+)-lio diresinol is formulated at a low concentration.
  • the whitening agent provided by the present invention contains rio diresinol and its isomers contained in whiskey, ume vinegar and the like that have been ingested for food and drink as active whitening ingredients, and only skin irritation. Or when taken orally, it is safe.
  • the whitening agent provided by the present invention has a feature that it is excellent in stability.
  • the whitening agent provided by the present invention can be produced by chemical synthesis, it has the advantage that it can be provided to consumers as an inexpensive whitening agent.
  • FIG. 1 is a graph showing the lyoniresinol content of extracts obtained by extracting American white oak and Spanish oak (new wood, old wood) with aqueous ethanol solutions of various concentrations.
  • ⁇ indicates 40% ethanol
  • ⁇ indicates 60% ethanol
  • mouth indicates 70% ethanol
  • ⁇ indicates 96% ethanol.
  • FIG. 2 shows a process for identifying an active ingredient for inhibiting tyrosinase activity from an ethanol extract (whiskey) of a beech family Quercus.
  • FIG. 3 shows the tyrosinase inhibitory activity of (+) rio-niresinol and (1) rioniresinol.
  • the vertical axis represents the inhibition rate (%).
  • FIG. 4 is a graph showing the amount of melanin produced in melanoma cells in mouse cells of lyoniresinol (racemate), (+)-ryoniresinol and (1) mono-lioresinol.
  • FIG. 5 shows the transition of lightness of guinea pig skin with respect to test sample application and ultraviolet irradiation.
  • the vertical axis shows the UV value when the L value immediately before application of the test sample is 0.
  • the difference in L value (AL) force from the start of application of the test sample to before irradiation, the number of days is shown on the horizontal axis.
  • a whitening agent characterized by containing at least one lioresinol of a compound represented by the formula as a whitening active ingredient.
  • the above formulas (A) to (H) are stereoisomers, and in the above formula, the compound represented by (A) is represented as (+) _ Lioniresinol ((+) _ Lyoniresinol) and represented by (E).
  • the resulting compound is known as (1) 1 lyone diresinol ((1) 1 Lyoniresinol).
  • lio-resinol is a compound represented by the formulas (A) and (E).
  • a tyrosinase activity inhibitor As a tyrosinase activity inhibitor, at least one of the two benzene rings having a carbon skeleton of lignans or norlignans is a 4-substituted resorcinol skeleton, followed by a benzylic skeleton.
  • a tyrosinase activity inhibitor see Patent Document 9 containing a lignan derivative and / or a kalelignan derivative as a whitening active ingredient in which the carbon atom has no substituent (see Patent Document 9).
  • the compounds according to the present invention represented by A) to (H) are lignans having an arylene tetralin skeleton, they are different from the above lignans having a resorcinol skeleton.
  • Rio diresinols used in the present invention that is, rio diresinol and its isomers are naturally occurring, but can also be obtained by chemical synthesis, and can be obtained by any means. Even if it exists, it can be used without trouble in the present invention.
  • a natural product it is not limited to purified rioniresinol, but a raw material extract or crude product containing rioniresinol can also be used as a whitening agent of the present invention, for example, beechaceae (Fagaceae) Quercus plants, aqueous extracts of lower alcohols of these plants, or purified products thereof can be used.
  • beechaceae Fagaceae Quercus plants, aqueous extracts of lower alcohols of these plants, or purified products thereof
  • ume vinegar that is produced as a by-product in the production of umeshu and umeboshi, extracts thereof, or purified products from ume vinegar extract can be used.
  • Quercus genus plants include, for example, Q. mongolica Fisch. ), White oak (Quercus alba L.), common oak (Quercus robur L .; also called Limousin oak, French oak or Spanish oak), stiil oak (Quercus oetraea L.), cork oak (Quercus suber L.), etc. Can be mentioned. Different forces depending on the plant's production area, harvest time, extraction conditions, etc. Among the above Quercus plants, the plant group (plants called oaks) used as raw materials for the production and storage of whiskey and brandy etc. In particular, common oak and Mizunara are preferred because they contain rio-niresinol at a high concentration.
  • Examples of the extraction solvent used for the production of the lower alcohol aqueous extract of the Quercus genus plant include aqueous solutions of lower alcohols having 1 to 4 carbon atoms (for example, methanol, ethanol, propanol, butanol, etc.). be able to. It is important that the concentration of the lower alcohol in the aqueous solution is a concentration at which rioniresinol can be efficiently extracted. Specifically, the lower alcohol concentration in the lower alcohol aqueous solution is about 10 to 100 volumes. %, Preferably about 30-70% by volume, more preferably about 40-60% by volume.
  • an aqueous ethanol solution is preferably used as the extraction solvent from the viewpoint of safety.
  • the extraction solvent is not limited to lower alcohol, and other solvents may be used as long as the extraction efficiency is not greatly impaired.
  • Components for example, water-soluble components such as sugars, salts, acids, alkalis or amino acids, and various other solvents such as ethyl acetate and acetone may be contained.
  • the extraction time may be set as appropriate, but in general, the longer the extraction time, the more rioniresinol can be extracted.
  • the rioniresinols according to the present invention can be produced by chemical synthesis, and the synthesis can be carried out generally as follows. That is, using 4-hydroxy-1,3,5-dimethyoxyphenylpropionic acid as a raw material, Indian Journal Chemistry, 1976, 14-8, 128 (INDIAN J. CHEM., VOL. 14B, FEBRUARY, 19 (P. 128, p. 128).
  • (+)-Lioniresinol and (I) Mono-Lioresinol are both useful materials as whitening agents, and their action mechanisms are different.
  • (+) _ Lionisinol has a high inhibitory effect on melanocyte activation by melanocyte-stimulating hormone (a-MSH), and effectively exerts a whitening effect from outside the cell.
  • Irioniresinol works directly on melanocytes to inhibit tyrosinase activity and inhibit melanin production.
  • these purified (+) _ rioniresinol and (1)-rioniresinol are used at an arbitrary ratio [about 1:99 to about 99: 1 (WZW)] depending on the purpose. It can be used by mixing.
  • the whitening agent of the present invention is produced by blending lio-resinols as a whitening active ingredient.
  • lio-resinols for example, foods, drinks, cosmetics and pharmaceuticals having an excellent whitening effect can be obtained.
  • the amount of rioniresinols to be added to the food, beverage, cosmetics and pharmaceuticals of the present invention varies depending on the form and use. Usually, about 0.0001 to 10% by weight is preferred. Weight percent is particularly preferred.
  • Examples of the food and drink containing the whitening active ingredient in the present invention include sports drinks, carbonated drinks, various drinks including fruit juices, soft drinks such as tea drinks, cakes, biscuits, breads, strawberries, and ice creams. Sweets such as cream, udon, soba, ramen, nosta, noodles such as somen, miso, soy sauce, vinegar, salad oil, sesame oil, butter, cheese, soy milk or What can be ingested as food, regardless of the type and form, such as milk. These can be produced by dissolving, mixing, etc., the whitening active ingredient of the present invention in food.
  • cosmetics include, for example, lotions, jewels, lotions, creams, pack si IJs, emulsions, emulsions or cream-like foundations, lipsticks, powders, facial cleansers, hair tonics, solids, etc. , Sol-like, paste-like, suitable for external use, soft capsules that break in the mouth, or those sprayed in the mouth, etc. are mentioned as cosmetics of the present invention.
  • These can be produced by a method known per se using other commonly used materials in addition to the whitening active ingredient according to the present invention.
  • Other commonly used materials include oils and fats (e.g.
  • waxes such as beeswax and carnavalou, jojoba oil, mink oil, cacao butter, palm oil, palm kernel oil, camellia oil, sesame oil, castor Oil, olive oil, etc.
  • surfactant for example, glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene alkyl ether, polyoxyethylene cetyl ether, sorbitan fatty acid ester, polyoxyethylene hydrogenated castor oil, polyglycerin
  • Fatty acid esters Fatty acid esters
  • lower or higher alcohols for example, cetanol, isostearyl alcohol, lauryl alcohol, hexadecyl alcohol, behenyl alcohol, otatildodecanol, etc.
  • fatty acids for example, lauric acid, myristic acid
  • Palmitic acid for example, Aric acid, undecylenic acid, oleic acid, etc.
  • water-soluble polymers eg,
  • pharmaceuticals for example, externally used liniments, patches, ointments, sol coatings, etc., granules to be taken orally, fine granules, tablets, capsules, syrups Or a liquid agent etc. are mentioned. These can be produced by a method known per se using other commonly used materials in addition to the whitening active ingredient according to the present invention.
  • excipients eg, lactose, sucrose, glucose, starch, crystalline cellulose, etc.
  • binders eg, starch paste, hydroxypropyl cellulose solution.
  • Carmellose solution gum arabic solution, gelatin solution, sodium alginate solution, etc.
  • disintegrant eg starch, carmellose sodium, calcium carbonate etc.
  • lubricant eg magnesium stearate, talc, stearic acid, stearin
  • surfactants eg polysorbate 80, polyoxyethylene hydrogenated castor oil, etc.
  • thickeners eg hydroxyethyl cellulose, hydroxypropyl cellulose, polybutyl alcohol, polyethylene glycol etc.
  • dosage forms for oral medicines and cosmetics include chewable tablets and troches.
  • oak American white oak and Spanish oak, old wood
  • the lyoniresinol content of the obtained extract was measured.
  • the measurement conditions are as follows.
  • a new pot was prepared as a whiskey storage raw liquor. That is, the germinated barley (malt) is pulverized, mixed with warm water, saccharified, yeast is added to the filtered sugar solution and fermented to obtain moromi having an alcohol content of 7.0 to 7.5% by volume. It was. The koji was placed in a copper pot still (single distiller) and distilled twice to obtain a composition (new pot) having an alcohol concentration of 60% by volume. Next, whiskey production barrels (white oak, spanish oak, mizunara new barrels) are used, the above new pots are put in these barrels, stoppered, and stored in the storage for 5 years to obtain barrel extract. It was. After 5 years, the rio-resinol content of the obtained barrel extract was measured.
  • the lyoniresinol content of the various barrel extracts was 4.9 mg / L for white oak, 11 ⁇ 39 mg / L for Spanish oak, and 10 ⁇ 7 mg / L for Mizunara.
  • a barrel extract of whiskey was made by using American white oak barrels (old wood) for whiskey production and a new pot produced in the same manner as in Example 2. Barrel extracts were collected over time (0, 4, 8, 12 years), and the lio-resinol content of the extract was measured.
  • the rio-resinol content of the barrel extract collected over time is 0 years: Omg / L, 4 years: 0.668 mg / L, 8 years: 1. 13 mg / L, 12 years: 2. 15 mg / L Met.
  • DMEM Dulbecco's Modified Eagle
  • the sample and crude tyrosinase enzyme solution prepared from B16 mouse melanoma cells were mixed, and L-dopa was added as a substrate to a concentration of 0 ⁇ 05% (W / W).
  • the mixture was reacted at 37 ° C for 20 minutes, and absorbance A at 492 nm (proportional to the amount of dopachrome) was measured.
  • absorbance B at 492 nm was measured, and the tyrosinase inhibition rate was calculated from the following formula.
  • Inhibition rate (%) (1 Absorbance AZ Absorbance B) X 100
  • Example 4 The active substance (fraction) isolated and purified in Example 4 was subjected to mass spectrometry (FAB MASS) and nuclear magnetic resonance NMR, 13 C-NMR) according to conventional methods, and spectral analysis was performed. went. As a result of dissolving FAB-MASS after dissolving the active substance in DMSO-D,
  • HPLC high performance liquid chromatography
  • the optical purity of the obtained fractions (+)-rioniresinol and (1) rioniresinol was 98% ee or higher, respectively.
  • the ratio of (+)-lio diresinol and (1) -lio diresinol obtained was about 1: 1 (w / w).
  • (+)-lio diresinol and (1) lio diresinol collected in Example 7 were used. 5 mg of the test substance was dissolved in DMSO (dimethyl sulfoxide), and tyrosinase inhibitory activity was measured in the same manner as in Example 4.
  • DMSO dimethyl sulfoxide
  • tyrosinase inhibitory activity was measured in the same manner as in Example 4.
  • arbutin which is widely used in the market as having tyrosinase activity inhibition, was prepared in the same manner as described above, and tyrosinase inhibitory activity was measured.
  • the whiskey congeners containing (+)-Lioniresinol and (I) -LioniResinol prepared in Example 7 and rioniresinol prepared in Example 4 were used, and DMSO ( Each was prepared to have a final concentration force of S100 ⁇ g / mL. 4 ⁇ 10 4 mouse B 16 melanoma cells were seeded in a 60 mm plastic dish and precultured. After 24 hours of pre-culture, the test substance was added and mixed, and further cultured at 37 ° C for 3 days.
  • the cells were washed with PBS, lysed by adding 1 mL of 1M NaOH to 1 ⁇ 10 6 centrifugal residues, and the absorbance at 470 nm was measured.
  • 0.1 ImM Nle ⁇ -Phe-a-melanocyte stimulating hormone (NDP-a_MSH) and the test substance were added and mixed, and further cultured at 37 ° C for 3 days.
  • the absorbance at 470 nm was measured.
  • the absorbance at 470 nm of the sample to which neither the test substance nor NDP-a-MSH was added was defined as an intracellular melanin amount of 100%, and the ratio of each sample was calculated.
  • saplinole was prepared in the same manner as described above using alpinin as a positive control, and the amount of intracellular melanin was measured.
  • Weiser maples (brown male guinea pig 4 weeks old) was purchased at room temperature 23.5.
  • C relative humidity 50 ⁇ 10%, ventilation rate 10-15 times / hour, lighting time 7:00 to 19: 0
  • polycarbonate gauge width 29.2cm, height 20cm, Preliminary breeding for 1 week at a depth of 44 cm.
  • Commercial chow and water (public tap water) were freely consumed.
  • body weight was measured once a week.
  • a group of 12 guinea pigs preliminarily raised was used, and each back was depilated with an electric clipper and an electric shever.
  • the guinea pig was placed on the back with a pattern, fixed on a compensator made of Sumipec 010 (UV transparent acrylic) and irradiated with ultraviolet rays.
  • a compensator made of Sumipec 010 (UV transparent acrylic) and irradiated with ultraviolet rays.
  • UV irradiation use UV irradiation device (CS & TOREX DERM ARAY medical UV irradiation device M— DMR 80 type) and UV-B lamp (TOREX FL20S -E-30 / DMR 20WAT TOSHIBA MEDICAL SUPPLY).
  • UV intensity meter (DERMARAY UVR-3036ZS2). From the first day of the test, the pigment was deposited by irradiating with ultraviolet rays once a day for 3 consecutive days.
  • test sample was started. Once a day, 40 / L was applied to each site.
  • the measurement site was measured five times using a color difference meter (Koni force Minolta COLOR READER CR-10), the skin color was displayed in the Lab color system, and the L value (lightness) was used for evaluation.
  • the average value of L values (AL value) was calculated and used as an index.
  • Fig. 5 shows the transition of skin color (AL value) when the test guinea pig was irradiated with ultraviolet rays (UV-B). A decrease in L value due to pigmentation was observed after the start of UV irradiation. In order to avoid measurement due to fluctuations in the amount of UV irradiation, the analysis was performed with the L value immediately before the start of application of the test sample as 0.
  • the group to which the test sample containing rioniresinol according to the present invention was applied showed the same melanin pigmentation inhibitory effect as the test sample containing arbutin. Considering that the concentration of the test sample containing rioniresinol according to the present invention is one-seventh the concentration of the test sample containing arbutin, rioniresinol according to the present invention has an excellent melamine pigmentation inhibitory effect. I found out.
  • test sample containing rio diresinol according to the present invention is apparently dermatitis, etc. No symptoms were observed.
  • Example 6 In 80 g of purified water, 0.5 g of poly (sodium acrylate) was dissolved, and rio diresinol (racemic) lg obtained in Example 6 was mixed with 18.5 g of ethyl alcohol, and a small amount of citrus essence was added. In preparation, a gel was prepared.
  • the present invention relates to a whitening treatment that contains liodiresinols that inhibit melanin production by inhibiting tyrosinase activity involved in melanin pigment production and / or inhibiting melanocyte activity by a-MSH.
  • An agent is provided. Therefore, the present invention is used in various products such as foods and drinks, cosmetics, and pharmaceuticals provided for the purpose of whitening.

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  • Life Sciences & Earth Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
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  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L’invention concerne un agent de blanchiment de la peau comprenant un lyonirésinol servant d’ingrédient efficace pour le blanchiment de la peau. Cet agent de blanchiment de la peau est utile sous forme d’aliment, de boisson, de produit cosmétique ou de produit pharmaceutique, etc. pour la prévention et le traitement du dépôt du pigment mélanine.
PCT/JP2005/023680 2004-12-24 2005-12-22 Agent de blanchiment de la peau Ceased WO2006068254A1 (fr)

Priority Applications (2)

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CN2005800447813A CN101102744B (zh) 2004-12-24 2005-12-22 美白剂
JP2006549073A JP5095221B2 (ja) 2004-12-24 2005-12-22 美白剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004374996 2004-12-24
JP2004-374996 2004-12-24

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WO2006068254A1 true WO2006068254A1 (fr) 2006-06-29

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CN (1) CN101102744B (fr)
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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2008048691A (ja) * 2006-08-25 2008-03-06 Suntory Ltd アルコール飲料の呈味向上剤
JP2010150152A (ja) * 2008-12-24 2010-07-08 Suntory Holdings Ltd リオニレシノール又はその類似体の製造方法
JP2010202598A (ja) * 2009-03-04 2010-09-16 Suntory Holdings Ltd 抗アレルギー剤
JP2010235483A (ja) * 2009-03-31 2010-10-21 Kose Corp 一重項酸素消去剤ならびにこれを含有する皮膚外用剤および化粧料
JP2011121921A (ja) * 2009-12-14 2011-06-23 Kracie Home Products Ltd 膵リパーゼ阻害剤並びにそれを含有する飲食品組成物及び医薬品組成物
WO2012099247A1 (fr) * 2011-01-21 2012-07-26 花王株式会社 Agent de blanchiment de la peau
JP2012149020A (ja) * 2011-01-21 2012-08-09 Kao Corp 美白剤
JP2012214434A (ja) * 2011-03-25 2012-11-08 Kose Corp 梅酢含有化粧料、及び梅酢を有効成分とする薬効剤
JP2013053077A (ja) * 2011-09-01 2013-03-21 Kao Corp 美白剤

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JP6270741B2 (ja) * 2012-12-25 2018-01-31 サントリーホールディングス株式会社 ハーブ抽出組成物

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JP2008048691A (ja) * 2006-08-25 2008-03-06 Suntory Ltd アルコール飲料の呈味向上剤
JP2010150152A (ja) * 2008-12-24 2010-07-08 Suntory Holdings Ltd リオニレシノール又はその類似体の製造方法
JP2010202598A (ja) * 2009-03-04 2010-09-16 Suntory Holdings Ltd 抗アレルギー剤
JP2010235483A (ja) * 2009-03-31 2010-10-21 Kose Corp 一重項酸素消去剤ならびにこれを含有する皮膚外用剤および化粧料
JP2011121921A (ja) * 2009-12-14 2011-06-23 Kracie Home Products Ltd 膵リパーゼ阻害剤並びにそれを含有する飲食品組成物及び医薬品組成物
WO2012099247A1 (fr) * 2011-01-21 2012-07-26 花王株式会社 Agent de blanchiment de la peau
JP2012149020A (ja) * 2011-01-21 2012-08-09 Kao Corp 美白剤
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JP2012214434A (ja) * 2011-03-25 2012-11-08 Kose Corp 梅酢含有化粧料、及び梅酢を有効成分とする薬効剤
JP2013053077A (ja) * 2011-09-01 2013-03-21 Kao Corp 美白剤

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CN101102744A (zh) 2008-01-09
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