WO2008148694A1 - Cosmetic composition comprising galacto-oligosaccharides - Google Patents

Cosmetic composition comprising galacto-oligosaccharides Download PDF

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Publication number
WO2008148694A1
WO2008148694A1 PCT/EP2008/056611 EP2008056611W WO2008148694A1 WO 2008148694 A1 WO2008148694 A1 WO 2008148694A1 EP 2008056611 W EP2008056611 W EP 2008056611W WO 2008148694 A1 WO2008148694 A1 WO 2008148694A1
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Prior art keywords
galacto
cosmetic composition
skin
oligosaccharide
gal
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PCT/EP2008/056611
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French (fr)
Inventor
Tomomi Kuromiya
Daisuke Suzuki
Masayoshi Miyamoto
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Chanel Parfums Beaute
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Publication of WO2008148694A1 publication Critical patent/WO2008148694A1/en

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
    • 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
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/007—Preparations for dry skin

Definitions

  • Cosmetic composition comprising galacto-oligosaccharides
  • the present invention relates to a plant extract, a cosmetic composition comprising the same, and a cosmetic skin care method using said cosmetic composition.
  • Cosmetic compositions in general, must possess high skin moisturizing effect in addition to their intrinsic benefits and effects. Specifically, imparting suitable moisture to the skin is extremely effective for fully displaying such intrinsic benefits and effects in cosmetic compositions directed at el iciting anti -aging effects, for instance by preventing and improving rough skin conditions , promoting skin whitening, preventing wrinkles or preventing skin fiabbiness and the like.
  • cosmetic compositions contain ordinarily moisturizer having high skin moisturizing effect .
  • moisturizers conventionally used include, for instance, glycerin, propylene glycol , sorbitol, maltitol, amino acids , pyrrolidone carboxylic acid, hyaluronic acid , plant extracts and the like.
  • glycerin propylene glycol
  • sorbitol maltitol
  • amino acids pyrrolidone carboxylic acid
  • hyaluronic acid hyaluronic acid
  • polyhydric alcohols such as glycerin, sorbitol and the like are problematic as regards their texture, since although relatively superior in skin moisturizing effect, in high concentrations they are prone to exhibit stickiness.
  • natural polysaccharide compounds such as hyaluronic acid or the like have little stickiness and are relatively superior as regards texture during application, but when formulated at high concentrations, in order to achieve a sufficient skin moisturizing effect, they end up increasing viscosity of formulation, which precludes displaying a sufficient skin moisturizing effect.
  • Oligosaccharides being formulated as moisturizer in cosmetic compositions .
  • "Oligosaccharides" of which there exist numerous examples depending on the type, number and bonding pattern of the constituent monosaccharide units, refer herein to compounds obtained through dehydration condensation of 2 to about 10 monosaccharides.
  • Japanese Patent Application Laid-open No. Hll-322574 describes a cosmetic material containing the trisaccharide raffinose as a moisturizer.
  • Japanese Patent Application Laid-open No. H07-330577 describes a galacto-oligosaccharide obtained through dehydration condensation of 3 to 6 monosaccharides, as a moisturi zer . Disclosure of Invention
  • the cosmetic composition according to the present invention is a cosmetic composition comprising a galacto-oligosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue .
  • the galacto-oligosaccharide has preferably a glucose residue .
  • galacto-oligosaccharide is preferably expressed by the following formula (1) :
  • each Gal independently represents a galactose residue
  • GIc represents a glucose residue
  • Fru represents a fructose residue
  • n represents an integer from 1 to 7.
  • the galacto-oligosaccharide is preferably at least one type selected from stachyose, verbascose and ajugose.
  • the inventors found out, moreover, that the galacto-oligosaccharide can be extracted at high concentrations from specific plants, and that adding such a galacto-ol igosaccharide in the cosmetic composition of the present invention is useful .
  • a galacto-oligosaccharide extracted from the Lamiaceae family flora allows suppressing stickiness and enhancing the skin moisturizing effect .
  • the Lamiaceae family flora belongs to the Stachys or Lycopus genus proved to be especially useful.
  • the inventors discovered that formulating a polyhydric alcohol together with the galacto-oligosaccharide in the cosmetic composition further enhances synergist ically the skin moisturizing effect, without causing stickiness associated with the polyhydric alcohol.
  • the term “cosmetic composition” refers to "a composition used on the human body through application, spreading or the like, for the purpose of cleaning, beautifying and imparting attractiveness to the body, for modifying personal appearance, or for preserving skin or hair healthiness, having therefore a gentle effect on the human body", as defined in Article 2(3) of the Japanese Pharmaceutical Affairs Law.
  • the term “cosmetic composition” encompasses herein also compositions for use in the applications defined in Article 1(2) or 1(3) of the Japanese Pharmaceutical Affairs Law, as well as quasi -drug compositions defined in Article 2(2) of the Japanese Pharmaceutical Affairs Law.
  • the term includes also compositions referred ordinarily to as "cosmetic materials” .
  • the cosmetic composition of the present invention thus, can provide excellent texture, low stickiness and enhanced skin moisturizing effect and can smoothen and hydrate the skin upon drying.
  • the cosmetic composition of the present invention can also be effective in enhancing the barrier function of the skin, strengthening the resistance of the skin to external and/or internal stress, strengthening the resistance of the skin to pollution, and enhancing the brightness of the skin, Best Mode for Carrying Out the Invention
  • the cosmetic composition of the present invention comprises as one essential constituent thereof a galacto-ol igosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue.
  • the type of galacto-oligosaccharide is not particularly limited, but it is preferably a galacto-oligosaccharide expressed by the following formula (1) :
  • each Gal independently represents a galactose residue
  • GIc represents a glucose residue
  • Fru represents a fructose residue
  • n represents an integer from 1 to 7, preferably from 1 to 3.
  • Gal preferably refers to ⁇ -D-galactose
  • GIc preferably refers to ⁇ -D-glucose
  • Fru preferably refers to ⁇ -D- fructose .
  • galacto-oligosaccharides include, for instance, stachyose, which includes an ⁇ -D-galactopyranosyl - ⁇ -D-galactopyranosyl - ⁇ -D-glucopyr anosyi -J3-D- fructofuranoside ; verbascose, which includes an ⁇ -D-galactopyranosyl - ⁇ -D-galactopyranosyl - ⁇ -D-galactop yranosyl - ⁇ -D-glucopyranosyl - ⁇ -D- fructofuranoside ; and ajugose, which includes an ⁇ -D-galactopyranosyl - ⁇ -D-galactopyranosyl - ⁇ -D-galactop yranosyl - ⁇ -D-galactopyranosyl - ⁇ -D-glucopyranosyl - ⁇ -D- f ruc
  • the galacto-oligosaccharide employed in the present invention can be obtained extracted from Lamiaceae family flora with a high yield.
  • galacto-oligosaccharides extracted from Lamiaceae family flora contain high concentrations of galacto-oligosaccharides that consists of 4 to 10 monosaccharide units and has a fructose residue or fructose residues including stachyose .
  • Such Lamiaceae family flora includes, for instance, plants belonging to the Stachys or Lycopus genus and the like.
  • plants belong to the Stachys genus include, for instance, Stachys tuberifera, Stachys sieboldii (CHOROGI / Chinese artichoke) , Stachys arvensis (YABUCHOROGI I stagger weed) ; specific examples of plants belong to the Lycopus genus include, for instance, Lycopus lucidus ( SHIRONE or Eleorchis japonica) , Lycopus maackianus ⁇ HIMESHIRONE), Lycopus ramosissimus
  • Stachys sieboldii and Lycopus lucidus are particularly preferred for use in this invention. Particularly preferred are roots of Lycopus lucidus ⁇ SHIRONE or Eleorchis japonica) , and Stachys sieboldii (CHOROGI I Chinese artichoke) , on account of their high safty and edibility. These plants may be used singly on in combinations of two or more.
  • Methods that can be used for extracting galacto-ol igosaccharides from such Lamiaceae family flora include, for instance, conventional extraction methods such as the one described in Japanese Patent Application Laid-open No. H05-207900.
  • a method for isolating and purifying target galacto-ol igosaccharides may involve, by way of example, using untreated or suitably dried, and optionally ground, parts (leaves, flowers, stalks, roots, preferably roots) of the aforementioned plants as a raw material that is then subjected to liquid phase extraction using water, an organic solvent such as alcohol or the like (preferably water) , or to gas phase extraction using water vapor or the like, followed for instance by chromatographic separation and suitable concentration of the obtained extract.
  • Examples of such isolation and purification methods can be found, for instance, in the Journal of the Research Society of Japan Sugar Refineries ' Technologists, Vol.38, p. 39-45 (1990) , and in the Research Journal of Food and Agriculture, Vol. 2 7 No . 2 , p . 2 9 - 3 2 ( 2 0 0 4 ) .
  • This invention also pertains to the plant extracts from the Lamiaceae family flora that contain galacto-ol igosaccharides as mentioned herein, and which may be obtained as described above, and to cosmetic compositions containing these plant extracts.
  • these plant extracts contain galacto-oligosaccharides, including raffinose and others , among which those described herein represent at least 70%, preferably at least 80%, for example at least 90%, of the total amount of galato-oligosaccharides .
  • the amount of the galacto-oligosaccharides as defined herein in the cosmetic composition of the present invention is not particularly limited, but ranges preferably from 0.1 to 30wt%, more preferably from 0.1 to 20wt%, and yet more preferably from 1 to 10wt%.
  • a cosmetic composition with an amount of a galacto-oligosaccharide below 0.1wt% may not achieve a sufficiently enhanced skin moisturizing effect with suppressed stickiness; on the other hand, at contents above 30wt% the effect may not be worth the increased amount.
  • the galacto-oligosaccharides according to this invention preferably contain at least 3 Owt% of stachyose , for example at least 50% of stachyose . In the present invention, "weight %" and "mass equivalent .
  • the cosmetic composition of the present invention contains preferably also a polyhydric alcohol. It has been found that such a concomitant use of a galacto-oligosaccharide and a polyhydric alcohol affords not only a higher skin moisturizing effect than when the galacto-oligosaccharide or the polyhydric alcohol are formulated singly but also suppress the stickiness ordinarily associated with polyhydric alcohols.
  • the present invention thus also pertains to a method for reducing or eliminating the sticky feel of a composition containing a polyhydric alcohol, comprising the step of mixing with said polyhydric alcohol at least one galacto-oligosaccharide as defined herein.
  • the detailed mechanism for such a synergistic effect of enhanced skin moisturizing effect and suppression of stickiness associated with polyhydric alcohol has not been elucidated as yet, although stickiness suppression is presumed to be the result of interference by galacto-oligosaccharide with the interaction between the hydroxy1 groups (-OH groups) of the polyhydric alcohol and water, which cause the stickiness .
  • the effect is not limited thereto.
  • the amount of polyhydric alcohol in the cosmetic composition is not particularly limited, and ranges preferably from 0.1 to 30wt%, more preferably from 1 to 20wt%, for example from 3 to 10wt%.
  • a cosmetic composition with an amount of polyhydric alcohol below 0.1wt% may not sufficiently exhibit the synergistic skin moisturizing effect, whereas a cosmetic composition containing polyhydric alcohol in excess of 30wt% may not suppress stickiness associated with the polyhydric alcohol even in the presence of the galacto-ol igosaccharide .
  • polyhydric alcohols include, for instance, glycerin, diglycerin, polyglycerin, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 3 -methyl - 1 , 3 -butanediol , 1,3-butylene glycol, polyethylene glycol, sugar alcohols such as sorbitol, maltitol or the like; these polyhydric alcohols may be used singly or in combinations of two or more thereof.
  • the form of the cosmetic composition of the present invention is not particularly limited, and may include a wide variety of forms such as an aqueous solution (for instance a lotion or the like) , an emulsion (for instance a milky lotion, cream or the like) , a powder, an oil, a gel, an ointment, a water-oil two-layer (phase) (w/o emulsion , o/w emulsion and the 1 ike ), or a water-oil -powder three-layer (phase) .
  • the composition includes a physiologically acceptable medium comprising water , such as purified water, hot spring water or deep water.
  • the application or formulation of the cosmetic composition of the invention are not particularly limited either, and may include any arbitrary formulation used ordinarily in cosmetics, such as a cream, milky lotion, lotion, pack, lipstick, foundation, jelly, ointment, film, powder or the like.
  • the method for preparat ion of the cosmet ic composition of the present invention is not particularly limited, and any conventional method may be used.
  • the cosmetic composition can be prepared for instance by dissolving the above -described moisturizer, i.e. galacto-ol igosaccharide in an aqueous phase , together with an emuisifier, followed by mixing and emulsifying this aqueous phase with a fused oil phase, under stirring.
  • the cosmetic composition of the present invention can be appl ied in the morning and/or the evening , over the entire face, neck and, optionally, low neck, or even body.
  • This composition can contain various adjuvants, such as at least one compound chosen from: oils, which can be chosen in part icular from : linear or cyclic, volatile or nonvolatile silicone oils, such as polydimethylsiloxanes (dimethicones ) , polyalkylcyclosiloxanes (cycloraethicones) and polyalkylphenylsiloxanes (phenyl dimethicones) ; synthetic oils such as fluoro oils, alkyl benzoates and branched hydrocarbons such as polyisobutylene / plant oils, and in particular soybean oil or jojoba oil; and mineral oils such as paraffin oil; waxes, such as ozokerite , polyethylene wax, beeswax or carnauba wax; - silicone elastomers obtained, in particular, by reaction, in the presence of a catalyst, of a polysiloxane having at least one reactive group (hydrogen or vinyl, in particular) and bearing at least one terminal and
  • fatty alcohol sulfate salts such as linear fatty alcohols, and in particular cetyl and stearyl alcohols; - thickeners and/or gelling agents , and in particular hydrophilic or amphiphilic, crosslinked or noncrosslinked homopolymers and copolymers of acryloylmethylpropanesulfonic acid (AMPS) and/or of acrylamide and/or of acrylic acid and/or of acrylic acid salts or esters; xanthan gum or guar gum; cellulose-based derivatives; and silicone gums (dimethiconol ) ; organic screening agents , such as dibenzoylmethane derivatives (including butylmethoxydibenzoylmethane) , cinnamic acid derivatives (including ethyl
  • UY sunscreen agents - dyes; preserving agents; fillers, and inparticular powders with a soft - focus effect , which can in particular be chosen from polyamides , silica, talc, mica, fibers (in particular of polyamide or of cellulose) ; sequestering agents such as EDTA salts; fragrances; and mixtures thereof, without this list being limiting .
  • CTFA dictionary International Cosmetic Ingredient Dictionary and Handbook published by The Cosmetic , Toiletry and Fragrance Association, 9th edition, 2002
  • composition used according to the invention can also provide additional benefits, including a soothing or ant i- inflammatory activity, a whitening or depigmenting activity, an anti-ageing activity and/or a cleansing activity .
  • composition used according to the invention can also comprise other act ive agents than the oligosaccharides, and in particular at least one active agent chosen from: keratolytic agents, and in particular ⁇ -hydroxy acids such as glycolic acid, lactic acid and citric acid, and esters thereof or salts thereof ; J3-hydroxy acids , such as salicylic acid and its derivatives; agents that stimulate the expression of the matriptase MT/SP1 such as an extract of carob pulp (Ceratonia siliqua) ; agents that increase keratinocyte differentiation and/or corneification , either directIy, or indirectly by stimulating, for example, the production of ⁇ -endorphins , such as extracts of Thermus thermophilics or of Theobroma cacao bean shells, water-soluble extracts of corn, peptide extracts of Voandzeia subterranea and niacinamide; epidermal lipids and agents that increase the synthesis of epidermal lipids , either directly, or by
  • the pH of the cosmetic composition of the present invention ranges from 4 to 8, preferably from 4.5 to 7.
  • Example 1 Preparation of a plant extrant from Lamiaceae family (Example 1-1)
  • Lucidus from the Lamiaceae family, were washed with water , peeled and, after being cut to a suitable size, were mixed in a mixer and were homogenized.
  • the obtained juice liquid was spun in a centrifuge ( 8000rpmxl5min . ) , then the supernatant was collected and passed through a cation-exchange resin (Diaion PK220 ) and an anion-exchange resin (WA30) .
  • the obtained extract (3.5 ml) was diluted with acetonitrile to a total volume of 10ml to give
  • Figure 1 shows an HPLC chart for Analytical Sample 1-1.
  • concentrations of each galacto-oligosaccharide in Analytical Sample 1-1 calculated based on the respective peak areas in Figure 1 are given in Table 1.
  • Example 1-2 Tuberous roots of CHOROGI (Stachys Sieboldii Miq) , from the Lamiaceae family, were washed with water, 5g of them were ground with a mortar and were mixed with purified water 5. Og to give an aqueous solution of an extract from CHOROGI. The aqueous solution (3.5 ml) was diluted with acetonitrile to a total volume of 10ml to give Analytical Sample 1-2.
  • CHOROGI Stachys Sieboldii Miq
  • Figure 2 shows the HPLC chart for Analytical Sample 1-2.
  • concentrations of each galacto-oligosaccharide in Analytical Sample 1-2 calculated based on the respective peak areas in Figure 2 are given in Table 2.
  • Example 2 Preparation of a cosmetic composition [Preparation of a galacto-oligosaccharide]
  • CHOROGI was washed with water and, after cutting to a suitable size, was charged in a mixer and was homogenized.
  • the obtained juice liquid was centrifuged ( 800 Orpnnx 15min . ) , then the supernatant was collected and was made to pass through a cation-exchange resin (Diaion PK220) and an anion-exchange resin (WA30) .
  • the obtained aqueous solution containing galacto-oligosaccharides was processed through column chromatography, then the stachyose fraction was collected, was concentrated in an evaporator, and was dried in accordance with the SprayDry method to yield stachyose (Gal 2 ⁇ Glc-Fru) .
  • Tuberous roots of of Eleorchis japonica (Lycopus Lucidus) were washed with water, were peeled and, after cutting to a suitable size, were mixed in a mixer and were homogenized.
  • the obtained juice liquid was spun in a centrifuge ( 8000rpmxl5min . ) , then the supernatant was collected and was made to pass through a cation-exchange resin (Diaion PK220) and an anion-exchange resin (WA30) .
  • the obtained aqueous solution containing galacto-oligosaccharides was processed through column chromatography, then the verbascose fraction was collected, was concentrated in an evaporator, and was dried in accordance with the SprayDry method to yield verbascose (GaI 3 -GIc-FrU) .
  • Oligomate S-HP (from Yakult Pharmaceutical Ind. Co., Ltd. ) was filtered through an aqueous filter (pore diameter 0.45 ⁇ l) and was passed through a cation-exchange resin (Diaion PK220) and an anion-exchange resin (WA30) .
  • the obtained aqueous solution containing galacto-oligosaccharides was processed through column chromatography, then the fraction of tetrasaccharide galacto-ol igosaccharide was collected, was concentrated in an evaporator, and was dried in accordance with the SprayDry method to yield a tetrasaccharide galacto-oligosaccharide (GaI 3 -GIc) .
  • number % denotes the content ("weight %" relative to the total weight of the cosmetic composition) .
  • Example 2-l A skin lotion was prepared in accordance with the formulation and preparative method below: (Formulation)
  • Stachyose (Preparative example 1) : 3.0%
  • Example 2-2> A cosmetic composition was prepared in Example 2-2 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of the verbascose of Preparative example 2 instead of 3.0% of the stachyose of Preparative example 1. ⁇ Example 2-3>
  • a cosmetic composition was prepared in Example 2-3 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of a stachyose hydrate ⁇ stachyose hydrate from Stachys tuberifera, from Sigma Aldrich Co.) instead of 3.0% of the stachyose of Preparative example 1 .
  • Example 2-5 A cosmetic composition was prepared in Example 2-4 in the same way as in Example 2-1, but by replacing herein 5,01 of the 89.471 of purified water in Example 1 with 5.0% of the polyhydric alcohol glycerin ⁇ "Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)). ⁇ Example 2-5>
  • Example 2-5 A cosmetic composition was prepared in Example 2-5 in the same way as in Example 2-2, but by replacing herein
  • Example 2 5.0% of the 89.47% of purified water in Example 2 with 5.0% of the polyhydric alcohol glycerin ( "Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)).
  • a cosmetic composition was prepared in Comparative example 2-2 in the same way as in Example 2-1, but by using herein, as the moisturi zer , 3.0% of raffinose (Gal -Glc-Fru) ("Oligo GGF" from Asahi Kasei Co. Ltd.), instead of 3.0% of the stachyose of Preparative example 1.
  • raffinose Gal -Glc-Fru
  • a cosmetic composition was prepared in Comparative example 2-3 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of the galacto-oligosaccharide comprising a tetrasaccharide having no fructose residues of the Comparative preparative example (GaI 3 -GIc) , instead of 3.0% of the stachyose of Preparative example 1.
  • the moisturizer 3.0% of the galacto-oligosaccharide comprising a tetrasaccharide having no fructose residues of the Comparative preparative example (GaI 3 -GIc) , instead of 3.0% of the stachyose of Preparative example 1.
  • a cosmetic composition was prepared in Comparative example 2-4 in the same way as in Example 2-1, but by using herein, as the moisturizer , 3.0% of glycerin ("Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)), instead of 3.0% of the stachyose of Preparative example 1.
  • a cosmetic composition was prepared in Comparative example 2-5 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of sodium pyrrolidone carboxylate ("PCA soda", from Aj inomoto Co . Ltd.), instead of 3.0% of the stachyose of Preparative example 1.
  • PCA soda sodium pyrrolidone carboxylate
  • a cosmetic composition was prepared in Comparative example 2-6 in the same way as in Comparative example 2-1, but by replacing herein 5.01 of the 89.47% of purified water in Comparative example 2-1 with 5.0% of the polyhydric alcohol glycerin ("Concentrated glycerin for cosmetic compositions" , by Kao (Ltd. ) ) .
  • Comparative example 2-7
  • a cosmetic composition was prepared in Comparative example 2-7 in the same way as in Comparative example 2-2, but by replacing herein 5.0% of the 89.47% of purified water in Comparative example 2-2 with 5.0% of the polyhydric alcohol glycerin ("Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)).
  • a cosmetic composition was prepared in Comparative example 2-8 in the same way as in Comparative example 2-3, but by replacing herein 5.0% of the 89.47% of purified water in Comparative example 2-3 with 5.0% of the polyhydric alcohol glycerin ("Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)).
  • Example 2 -3 60 65 60 61 59 58 58 63 63 58 60 .5 + 1
  • Table 4 summarizes the results of the evaluation of skin moisturizing effect and texture of Examples 2-1 to 2-5 and Comparative examples 2-1 to 2-8. [Table 4]
  • Example 2-1 to 2-5 corresponding to the cosmetic composition of the present invention, yielded a superior skin moisturizing effect and a superior texture (low degree of stickiness) vis-a-vis Comparative examples 2-1 to 2-8.
  • Example 2-1 and Comparative example 2-3 within both of which a tetrasaccharide galacto-oligosaccharide was used, it is indicated that galacto-oligosaccharides having fructose residues have superior skin moisturizing effect and texture vis-a-vis galacto-oligosaccharides having no fructose residues.
  • Examples 2-4 and 2-5 show that combining a polyhydric alcohol with a galacto-oligosaccharide having fructose residues further enhances the skin moisturizing effect of the galacto-oligosaccharide.
  • the results of Comparative examples 2-6 and 2-8 indicate that the synergistic effect displayed in Examples 2-4 and 2-5 is not observed for other galacto-oligosaccharides (sucrose and the galacto-oligosaccharide of the Comparative preparative example) .
  • the cosmetic composition of the present invention thus, is virtually free of the stickiness problem of conventional moisturizers, and elicits moreover a remarkably high skin moisturizing effect.
  • the cosmetic composition of the present invention has less stickiness, a superior texture and a improved skin moisturizing effect and can smoothen and hydrate the skin , and hence it is useful as a cosmetic composition embodied in a wide variety of forms.

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Abstract

The present invention pertains to a moisturizing cosmetic composition comprising a galacto-oligosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue. This galacto-oligosaccharide may be obtained from a plant belonging to the Lamiaceae family flora. The invention also pertains to a novel extract from this plant. This composition has a satisfactorily improved skin moisturizing effect without stickiness. Moreover, the galacto-oligosaccharide provides for a specific synergetic effect with polyhydric alcohols, resulting in a further increased skin moisturizing effect.

Description

Cosmetic composition comprising galacto-oligosaccharides
Technical Field The present invention relates to a plant extract, a cosmetic composition comprising the same, and a cosmetic skin care method using said cosmetic composition. Background Art
Cosmetic compositions, in general, must possess high skin moisturizing effect in addition to their intrinsic benefits and effects. Specifically, imparting suitable moisture to the skin is extremely effective for fully displaying such intrinsic benefits and effects in cosmetic compositions directed at el iciting anti -aging effects, for instance by preventing and improving rough skin conditions , promoting skin whitening, preventing wrinkles or preventing skin fiabbiness and the like.
To that end, cosmetic compositions contain ordinarily moisturizer having high skin moisturizing effect . Examples of such moisturizers conventionally used include, for instance, glycerin, propylene glycol , sorbitol, maltitol, amino acids , pyrrolidone carboxylic acid, hyaluronic acid , plant extracts and the like. Although endowed with high skin moisturizing effect, however, such moisturizer sometimes exhibit, depending on the used amount, sticky texture, which tends to detract from the texture of the cosmetic composition. In other words, no moisturizer existed thus far that combined simultaneously high skin moisturizing effect with low stickiness. More specifically, polyhydric alcohols such as glycerin, sorbitol and the like are problematic as regards their texture, since although relatively superior in skin moisturizing effect, in high concentrations they are prone to exhibit stickiness. On the other hand, natural polysaccharide compounds such as hyaluronic acid or the like have little stickiness and are relatively superior as regards texture during application, but when formulated at high concentrations, in order to achieve a sufficient skin moisturizing effect, they end up increasing viscosity of formulation, which precludes displaying a sufficient skin moisturizing effect. There was thus a demand for a moisturizer, and a cosmetic composition comprising the same, that should not result in increasing viscosity, even when formulated in large amounts, and should suppress stickiness to afford excellent texture.
In this context, there have been studies on oligosaccharides being formulated as moisturizer in cosmetic compositions . "Oligosaccharides", of which there exist numerous examples depending on the type, number and bonding pattern of the constituent monosaccharide units, refer herein to compounds obtained through dehydration condensation of 2 to about 10 monosaccharides.
For instance, Japanese Patent Application Laid-open No. Hll-322574 describes a cosmetic material containing the trisaccharide raffinose as a moisturizer. Also, Japanese Patent Application Laid-open No. H07-330577 describes a galacto-oligosaccharide obtained through dehydration condensation of 3 to 6 monosaccharides, as a moisturi zer . Disclosure of Invention
Although the raffinose described in Japanese Patent Application Laid-open No. Hll-322574 does not increase viscosity of formulation, and hence does not cause stickiness or impair texture of cosmetic compositions even when formulated in substantial amounts, it is still not satisfactory enough as regards skin moisturizing effect, as is the case for the above-described natural polysaccharide components. Similarly, the galacto-oligosaccharide described in Japanese Patent Application Laid-open No. H07-330577 suppresses stickiness, but does not necessarily afford a sufficient skin moisturizing effect.
In light of the above, it is an object of the present invention to provide a cosmetic composition having excellent texture, low stickiness and sufficiently enhanced skin moisturizing effect, and capable of smoothening and hydrating the skin upon drying.
As a result of diligent research directed at solving the above problems, the inventors discovered that formulating in a cosmetic composition a galacto-oligosaccharide having at least four monosaccharide units and having a residue or residues of specific saccharide , as a moisturizer , allows sufficiently suppressing stickiness, while eliciting a remarkably high skin moisturizing effect.
Specifically, the cosmetic composition according to the present invention is a cosmetic composition comprising a galacto-oligosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue . The galacto-oligosaccharide has preferably a glucose residue .
Furthermore, the galacto-oligosaccharide is preferably expressed by the following formula (1) :
Gal- (Gal) n-Glc-Fru (1) In the formula, each Gal independently represents a galactose residue, GIc represents a glucose residue, Fru represents a fructose residue, and n represents an integer from 1 to 7.
Specifically, the galacto-oligosaccharide is preferably at least one type selected from stachyose, verbascose and ajugose.
The inventors found out, moreover, that the galacto-oligosaccharide can be extracted at high concentrations from specific plants, and that adding such a galacto-ol igosaccharide in the cosmetic composition of the present invention is useful . Specifically, it was found that using as the galacto-oligosaccharide a galacto-oligosaccharide extracted from the Lamiaceae family flora allows suppressing stickiness and enhancing the skin moisturizing effect . In particular , the Lamiaceae family flora belongs to the Stachys or Lycopus genus proved to be especially useful.
The inventors, moreover, discovered that formulating a polyhydric alcohol together with the galacto-oligosaccharide in the cosmetic composition further enhances synergist ically the skin moisturizing effect, without causing stickiness associated with the polyhydric alcohol.
In the present invention, the term "cosmetic composition" refers to "a composition used on the human body through application, spreading or the like, for the purpose of cleaning, beautifying and imparting attractiveness to the body, for modifying personal appearance, or for preserving skin or hair healthiness, having therefore a gentle effect on the human body", as defined in Article 2(3) of the Japanese Pharmaceutical Affairs Law. In addition to the above use purposes, the term "cosmetic composition" encompasses herein also compositions for use in the applications defined in Article 1(2) or 1(3) of the Japanese Pharmaceutical Affairs Law, as well as quasi -drug compositions defined in Article 2(2) of the Japanese Pharmaceutical Affairs Law. The term includes also compositions referred ordinarily to as "cosmetic materials" . The cosmetic composition of the present invention, thus, can provide excellent texture, low stickiness and enhanced skin moisturizing effect and can smoothen and hydrate the skin upon drying.
In addition to the skin moisturizing effect, the cosmetic composition of the present invention can also be effective in enhancing the barrier function of the skin, strengthening the resistance of the skin to external and/or internal stress, strengthening the resistance of the skin to pollution, and enhancing the brightness of the skin, Best Mode for Carrying Out the Invention
An embodiment of the invention is described in detail next .
As explained above, the cosmetic composition of the present invention comprises as one essential constituent thereof a galacto-ol igosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue. The type of galacto-oligosaccharide is not particularly limited, but it is preferably a galacto-oligosaccharide expressed by the following formula (1) :
Gal-(Gal)n-Glc-Fru (1)
In the formula, each Gal independently represents a galactose residue, GIc represents a glucose residue, Fru represents a fructose residue, and n represents an integer from 1 to 7, preferably from 1 to 3.
Moreover, "Gal" preferably refers to α-D-galactose , "GIc " preferably refers to α-D-glucose and " Fru" preferably refers to β-D- fructose .
Examples of such galacto-oligosaccharides include, for instance, stachyose, which includes an α-D-galactopyranosyl -α-D-galactopyranosyl -α-D-glucopyr anosyi -J3-D- fructofuranoside ; verbascose, which includes an α-D-galactopyranosyl -α-D-galactopyranosyl -α-D-galactop yranosyl -α-D-glucopyranosyl -β-D- fructofuranoside ; and ajugose, which includes an α-D-galactopyranosyl -α-D-galactopyranosyl -α-D-galactop yranosyl -α-D-galactopyranosyl - α-D-glucopyranosyl -β -D- f ructofuranoside ; these saccharides may be used singly or in combinations of two or more thereof. Apart from a method such as the one described in
Japanese Patent Appl icat ion Laid-open No . H08-168393, the galacto-oligosaccharide employed in the present invention can be obtained extracted from Lamiaceae family flora with a high yield.
Conventional methods for manufacturing galacto-oligosaccharides achieve normally low galacto-oligosaccharide yields on account of by-product formation. By contrast, it has been found that galacto-oligosaccharides extracted from Lamiaceae family flora contain high concentrations of galacto-oligosaccharides that consists of 4 to 10 monosaccharide units and has a fructose residue or fructose residues including stachyose . Such Lamiaceae family flora includes, for instance, plants belonging to the Stachys or Lycopus genus and the like. Specific examples of plants belong to the Stachys genus include, for instance, Stachys tuberifera, Stachys sieboldii (CHOROGI / Chinese artichoke) , Stachys arvensis (YABUCHOROGI I stagger weed) ; specific examples of plants belong to the Lycopus genus include, for instance, Lycopus lucidus ( SHIRONE or Eleorchis japonica) , Lycopus maackianus {HIMESHIRONE), Lycopus ramosissimus
(SARUDAHIMO or KOSHIRONE) , Lycopus uniflorus [EZOSHIRONE) and the like. Stachys sieboldii and Lycopus lucidus are particularly preferred for use in this invention. Particularly preferred are roots of Lycopus lucidus {SHIRONE or Eleorchis japonica) , and Stachys sieboldii (CHOROGI I Chinese artichoke) , on account of their high safty and edibility. These plants may be used singly on in combinations of two or more.
Methods that can be used for extracting galacto-ol igosaccharides from such Lamiaceae family flora include, for instance, conventional extraction methods such as the one described in Japanese Patent Application Laid-open No. H05-207900. More specifically, a method for isolating and purifying target galacto-ol igosaccharides may involve, by way of example, using untreated or suitably dried, and optionally ground, parts (leaves, flowers, stalks, roots, preferably roots) of the aforementioned plants as a raw material that is then subjected to liquid phase extraction using water, an organic solvent such as alcohol or the like (preferably water) , or to gas phase extraction using water vapor or the like, followed for instance by chromatographic separation and suitable concentration of the obtained extract. Examples of such isolation and purification methods can be found, for instance, in the Journal of the Research Society of Japan Sugar Refineries ' Technologists, Vol.38, p. 39-45 (1990) , and in the Research Journal of Food and Agriculture, Vol. 2 7 No . 2 , p . 2 9 - 3 2 ( 2 0 0 4 ) .
This invention also pertains to the plant extracts from the Lamiaceae family flora that contain galacto-ol igosaccharides as mentioned herein, and which may be obtained as described above, and to cosmetic compositions containing these plant extracts.
According to an embodiment of this invention, these plant extracts contain galacto-oligosaccharides, including raffinose and others , among which those described herein represent at least 70%, preferably at least 80%, for example at least 90%, of the total amount of galato-oligosaccharides .
The amount of the galacto-oligosaccharides as defined herein in the cosmetic composition of the present invention is not particularly limited, but ranges preferably from 0.1 to 30wt%, more preferably from 0.1 to 20wt%, and yet more preferably from 1 to 10wt%. A cosmetic composition with an amount of a galacto-oligosaccharide below 0.1wt% may not achieve a sufficiently enhanced skin moisturizing effect with suppressed stickiness; on the other hand, at contents above 30wt% the effect may not be worth the increased amount. Moreover, the galacto-oligosaccharides according to this invention preferably contain at least 3 Owt% of stachyose , for example at least 50% of stachyose . In the present invention, "weight %" and "mass equivalent .
In addition to the above-described galacto-oligosaccharide , the cosmetic composition of the present invention contains preferably also a polyhydric alcohol. It has been found that such a concomitant use of a galacto-oligosaccharide and a polyhydric alcohol affords not only a higher skin moisturizing effect than when the galacto-oligosaccharide or the polyhydric alcohol are formulated singly but also suppress the stickiness ordinarily associated with polyhydric alcohols.
The present invention thus also pertains to a method for reducing or eliminating the sticky feel of a composition containing a polyhydric alcohol, comprising the step of mixing with said polyhydric alcohol at least one galacto-oligosaccharide as defined herein.
The detailed mechanism for such a synergistic effect of enhanced skin moisturizing effect and suppression of stickiness associated with polyhydric alcohol has not been elucidated as yet, although stickiness suppression is presumed to be the result of interference by galacto-oligosaccharide with the interaction between the hydroxy1 groups (-OH groups) of the polyhydric alcohol and water, which cause the stickiness . The effect, however, is not limited thereto. The amount of polyhydric alcohol in the cosmetic composition is not particularly limited, and ranges preferably from 0.1 to 30wt%, more preferably from 1 to 20wt%, for example from 3 to 10wt%. A cosmetic composition with an amount of polyhydric alcohol below 0.1wt% may not sufficiently exhibit the synergistic skin moisturizing effect, whereas a cosmetic composition containing polyhydric alcohol in excess of 30wt% may not suppress stickiness associated with the polyhydric alcohol even in the presence of the galacto-ol igosaccharide . Specific examples of polyhydric alcohols include, for instance, glycerin, diglycerin, polyglycerin, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, 3 -methyl - 1 , 3 -butanediol , 1,3-butylene glycol, polyethylene glycol, sugar alcohols such as sorbitol, maltitol or the like; these polyhydric alcohols may be used singly or in combinations of two or more thereof.
The form of the cosmetic composition of the present invention is not particularly limited, and may include a wide variety of forms such as an aqueous solution (for instance a lotion or the like) , an emulsion (for instance a milky lotion, cream or the like) , a powder, an oil, a gel, an ointment, a water-oil two-layer (phase) (w/o emulsion , o/w emulsion and the 1 ike ), or a water-oil -powder three-layer (phase) . Preferably, the composition includes a physiologically acceptable medium comprising water , such as purified water, hot spring water or deep water. The application or formulation of the cosmetic composition of the invention are not particularly limited either, and may include any arbitrary formulation used ordinarily in cosmetics, such as a cream, milky lotion, lotion, pack, lipstick, foundation, jelly, ointment, film, powder or the like. The method for preparat ion of the cosmet ic composition of the present invention is not particularly limited, and any conventional method may be used. In the case of a milky lotion or a cream, for example, the cosmetic composition can be prepared for instance by dissolving the above -described moisturizer, i.e. galacto-ol igosaccharide in an aqueous phase , together with an emuisifier, followed by mixing and emulsifying this aqueous phase with a fused oil phase, under stirring.
The cosmetic composition of the present invention can be appl ied in the morning and/or the evening , over the entire face, neck and, optionally, low neck, or even body.
This composition can contain various adjuvants, such as at least one compound chosen from: oils, which can be chosen in part icular from : linear or cyclic, volatile or nonvolatile silicone oils, such as polydimethylsiloxanes (dimethicones ) , polyalkylcyclosiloxanes (cycloraethicones) and polyalkylphenylsiloxanes (phenyl dimethicones) ; synthetic oils such as fluoro oils, alkyl benzoates and branched hydrocarbons such as polyisobutylene / plant oils, and in particular soybean oil or jojoba oil; and mineral oils such as paraffin oil; waxes, such as ozokerite , polyethylene wax, beeswax or carnauba wax; - silicone elastomers obtained, in particular, by reaction, in the presence of a catalyst, of a polysiloxane having at least one reactive group (hydrogen or vinyl, in particular) and bearing at least one terminal and/or lateral alkyl (in particular methyl) or phenyl group, with an organosil icone such as an organohydrogenopolysiloxane ; surfactants, preferably emulsifiers , irrespective of whether they are nonionic, anionic, cationic or amphoteric , and in particular fatty acid esters of polyols , such as fatty acid esters of glycerol, fatty acid esters of sorbitan, fatty acid esters of polyethylene glycol and fatty acid esters of sucrose; fatty alcohol ethers of polyethylene glycol; alkylpolygiucosides ; polyether-modified polysiloxanes ; betaine and derivatives thereof; polyquaterniums ; ethoxylated. fatty alcohol sulfate salts; sulf©succinates ; sarcosinates ; alkyi phosphates and dialkyl phosphates and salts thereof; and fatty acid soaps; cosurfactants , such as linear fatty alcohols, and in particular cetyl and stearyl alcohols; - thickeners and/or gelling agents , and in particular hydrophilic or amphiphilic, crosslinked or noncrosslinked homopolymers and copolymers of acryloylmethylpropanesulfonic acid (AMPS) and/or of acrylamide and/or of acrylic acid and/or of acrylic acid salts or esters; xanthan gum or guar gum; cellulose-based derivatives; and silicone gums (dimethiconol ) ; organic screening agents , such as dibenzoylmethane derivatives (including butylmethoxydibenzoylmethane) , cinnamic acid derivatives (including ethylhexyl methoxycinnamate) , salicylates, para-aminobenzoic acids , β , β ' -diphenyl acrylates, benzophenones , benzyl idenecamphor derivatives, phenylbenzimidazoles , triazines, phenylbenzotriazoles and anthranilic derivatives ; - inorganic screening agents based on mineral oxides in the form of pigments or nanopigments , which are coated or uncoated, and in particular based on titanium dioxide or zinc oxide;
UY sunscreen agents; - dyes; preserving agents; fillers, and inparticular powders with a soft - focus effect , which can in particular be chosen from polyamides , silica, talc, mica, fibers (in particular of polyamide or of cellulose) ; sequestering agents such as EDTA salts; fragrances; and mixtures thereof, without this list being limiting . Examples of such adj uvants are mentioned in particular in the CTFA dictionary (International Cosmetic Ingredient Dictionary and Handbook published by The Cosmetic , Toiletry and Fragrance Association, 9th edition, 2002) , which describes a great diversity, without limitation, of cosmetic and pharmaceutical ingredients normally used in the skin care industry, which are suitable to be used as additional ingredients in the compositions according to the present invention.
The composition used according to the invention can also provide additional benefits, including a soothing or ant i- inflammatory activity, a whitening or depigmenting activity, an anti-ageing activity and/or a cleansing activity .
The composition used according to the invention can also comprise other act ive agents than the oligosaccharides, and in particular at least one active agent chosen from: keratolytic agents, and in particular α-hydroxy acids such as glycolic acid, lactic acid and citric acid, and esters thereof or salts thereof ; J3-hydroxy acids , such as salicylic acid and its derivatives; agents that stimulate the expression of the matriptase MT/SP1 such as an extract of carob pulp (Ceratonia siliqua) ; agents that increase keratinocyte differentiation and/or corneification , either directIy, or indirectly by stimulating, for example, the production of β-endorphins , such as extracts of Thermus thermophilics or of Theobroma cacao bean shells, water-soluble extracts of corn, peptide extracts of Voandzeia subterranea and niacinamide; epidermal lipids and agents that increase the synthesis of epidermal lipids , either directly, or by stimulating certain β-glucosidases which modulate the deglycosylat ion of lipid precursors such as glucosylceramide to ceramides, such as phospholipids, ceramides, or lupin protein hydrolysates and dihydroj asmonic acid derivatives; agents stimulating the expression of fructosamine 3-kinase (FN3K) or its related protein (FN3K RP) ; humectants, such as polyols, and in particular glycerol, glycosaminoglycans such as hyaluronic acid, sugars, their mixtures like the product sold by PENTAPHARM under the trade name Pentavitin® and their alkyl esters, amino acids such as glycine, arginine, histidine, alanine, threonine, lysine, glutamic acid, taurine, proline, serine and their derivatives, pyrrol idonecarboxyl ic acid (PCA) and its salts, urea and its derivatives, ectoin, glucosamine, creatine, choline, betaine , mineral salts such as chlorine salts, sodium salts , potassium salts , calcium salts , magnesium salts , zinc salts, manganese salts or phosphate salts , and humectant synthetic polymers such as homopolymers and copolymers of methacryloyloxyethylphosphorylcholine and homopolymers and copolymers of glyceryl (meth) acrylate ; filling systems; agents for facilitating percutaneous absorption, such as alcohols, fatty alcohols and fatty acids and their ester or ether derivatives, pyrrolidones , terpenes, essential oils and α-hydroxy acids; antioxidants and/or free-radical scavengers and/or ant ipollution agents, such as tocopherol and its esters, ascorbic acid and its alkyl and phosphoryl esters and certain extracts of plants or of algae, and in particular of Thermus thermophilus ; and mixtures thereof, without this list being limiting.
In terms of achieving a sufficient effect and of increasing safety, the pH of the cosmetic composition of the present invention ranges from 4 to 8, preferably from 4.5 to 7. Examples
The present invention is explained in more detail in the follwing examples, although the invention is not meant in any way to be limited to or by them. Example 1 : Preparation of a plant extrant from Lamiaceae family (Example 1-1)
Tuberous roots of Eleorchis japonica (Lycopus
Lucidus) , from the Lamiaceae family, were washed with water , peeled and, after being cut to a suitable size, were mixed in a mixer and were homogenized. The obtained juice liquid was spun in a centrifuge ( 8000rpmxl5min . ) , then the supernatant was collected and passed through a cation-exchange resin (Diaion PK220 ) and an anion-exchange resin (WA30) . The obtained extract (3.5 ml) was diluted with acetonitrile to a total volume of 10ml to give
Analytical Sample 1-1.
Galacto-ol igosaccharides in the obtained Analytical Samplel-1 were analyzed by high-performance liquid column chromatography under the following conditions. Analytical conditions
Column : Shodex AsahipakNH2P-504E (4.6mm I. D., 250mm long)
Mobile phase: acetonitrile-water (65:35) Flow rate: l.Oml/min Colum temperatue : 350C
Injection volume: lOμl
Detector: refractive index detector
Figure 1 shows an HPLC chart for Analytical Sample 1-1. The concentrations of each galacto-oligosaccharide in Analytical Sample 1-1 calculated based on the respective peak areas in Figure 1 are given in Table 1.
[Table 1] retention peak area concentration time ( min ) ( MV ) ( Wt % ) raff inose 9.356 3857 57 0.09 stachyose 13.169 3433 73 0.27 verbascose about less than
18.744 1011 414 0.20 aj ugose 27.285 4117 18 about 0.08
The result in Table 1 confirmed that an extract from
tuberous roots of Eleorchis japonica (Lycopus Lucidus) , from the Lamiaceae family, contained stachyose
(GaI2 -GIc -Fru) , verbascose (GaI3 -Glc-Fru) and ajugose (GaI4-GIc-FrU) in the ratio of roughly 3 : 2 : 1.
(Example 1-2) Tuberous roots of CHOROGI (Stachys Sieboldii Miq) , from the Lamiaceae family, were washed with water, 5g of them were ground with a mortar and were mixed with purified water 5. Og to give an aqueous solution of an extract from CHOROGI. The aqueous solution (3.5 ml) was diluted with acetonitrile to a total volume of 10ml to give Analytical Sample 1-2.
Galacto-oligosaccharides in the obtained Analytical Samplel-2 were analyzed in the same way as in Example 1-1.
Figure 2 shows the HPLC chart for Analytical Sample 1-2. The concentrations of each galacto-oligosaccharide in Analytical Sample 1-2 calculated based on the respective peak areas in Figure 2 are given in Table 2.
[Table 2]
Figure imgf000022_0001
The result in Table 2 confirmed that an extract from tuberous roots of CHOROGI, from the Lamiaceae family, contained stachyose and ajugose in the ratio of about
12 : 1.
Example 2: Preparation of a cosmetic composition [Preparation of a galacto-oligosaccharide]
(Preparative example 1) : Stachyose (from CHOROGI / Stachys sieholdii)
CHOROGI was washed with water and, after cutting to a suitable size, was charged in a mixer and was homogenized. The obtained juice liquid was centrifuged ( 800 Orpnnx 15min . ) , then the supernatant was collected and was made to pass through a cation-exchange resin (Diaion PK220) and an anion-exchange resin (WA30) . The obtained aqueous solution containing galacto-oligosaccharides was processed through column chromatography, then the stachyose fraction was collected, was concentrated in an evaporator, and was dried in accordance with the SprayDry method to yield stachyose (Gal2~Glc-Fru) .
(Preparative example 2) : verbascose (from Eleorchis japonica / Lycopus lucidus)
Tuberous roots of of Eleorchis japonica (Lycopus Lucidus) were washed with water, were peeled and, after cutting to a suitable size, were mixed in a mixer and were homogenized. The obtained juice liquid was spun in a centrifuge ( 8000rpmxl5min . ) , then the supernatant was collected and was made to pass through a cation-exchange resin (Diaion PK220) and an anion-exchange resin (WA30) . The obtained aqueous solution containing galacto-oligosaccharides was processed through column chromatography, then the verbascose fraction was collected, was concentrated in an evaporator, and was dried in accordance with the SprayDry method to yield verbascose (GaI3-GIc-FrU) .
(Comparative preparative example) : galacto-ol igosaccharide comprising a tetrasaccharide having no fructose residues
Oligomate S-HP (from Yakult Pharmaceutical Ind. Co., Ltd. ) was filtered through an aqueous filter (pore diameter 0.45 μl) and was passed through a cation-exchange resin (Diaion PK220) and an anion-exchange resin (WA30) . The obtained aqueous solution containing galacto-oligosaccharides was processed through column chromatography, then the fraction of tetrasaccharide galacto-ol igosaccharide was collected, was concentrated in an evaporator, and was dried in accordance with the SprayDry method to yield a tetrasaccharide galacto-oligosaccharide (GaI3-GIc) .
[Preparation of a cosmetic composition] Cosmetic compositions in Examples and Comparative examples were prepared as described below.
Herein, "numerical value %" denotes the content ("weight %" relative to the total weight of the cosmetic composition) .
<Example 2-l> A skin lotion was prepared in accordance with the formulation and preparative method below: (Formulation)
(1) Stachyose (Preparative example 1) : 3.0%
(2) Purified water: 89.47% (3) Xanthane gum: 0.1% (4) 1,3-butylene glycol: 3.0%
(5) Methyl benzoate : 0.2%
(6) Ethanol : 4.0%
(7) Polyoxyethylene (24 mole) polyoxypropylene (24 mole) glyceryl ether: 0.2%
(8) Fragrance: 0.03% (Preparative method)
The above component s (1) to (5) were mixed and dissolved to yield a mixture A. Also, the above components (6) to (8) were mixed and dissolved to yield a mixture B . The mixture B was added to the mixture A, under stirring, to homogenize the resulting mixture and yield thereby a cosmetic composition of Example 2-1. <Example 2-2> A cosmetic composition was prepared in Example 2-2 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of the verbascose of Preparative example 2 instead of 3.0% of the stachyose of Preparative example 1. <Example 2-3>
A cosmetic composition was prepared in Example 2-3 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of a stachyose hydrate {stachyose hydrate from Stachys tuberifera, from Sigma Aldrich Co.) instead of 3.0% of the stachyose of Preparative example 1 .
< Examp l e 2 - 4 >
A cosmetic composition was prepared in Example 2-4 in the same way as in Example 2-1, but by replacing herein 5,01 of the 89.471 of purified water in Example 1 with 5.0% of the polyhydric alcohol glycerin { "Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)). <Example 2-5>
A cosmetic composition was prepared in Example 2-5 in the same way as in Example 2-2, but by replacing herein
5.0% of the 89.47% of purified water in Example 2 with 5.0% of the polyhydric alcohol glycerin ( "Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)).
<Comparative example 2-l> A cosmetic composition was prepared in Comparative example 2-1 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of sucrose (Glc-Fru) (sucrose, Special grade, from Kanto Chemical Co. Ltd.) , instead of 3.0% of the stachyose of Preparative example 1.
<Comparative example 2-2>
A cosmetic composition was prepared in Comparative example 2-2 in the same way as in Example 2-1, but by using herein, as the moisturi zer , 3.0% of raffinose (Gal -Glc-Fru) ("Oligo GGF" from Asahi Kasei Co. Ltd.), instead of 3.0% of the stachyose of Preparative example 1.
<Comparative example 2-3>
A cosmetic composition was prepared in Comparative example 2-3 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of the galacto-oligosaccharide comprising a tetrasaccharide having no fructose residues of the Comparative preparative example (GaI3-GIc) , instead of 3.0% of the stachyose of Preparative example 1. <Comparative example 2-4>
A cosmetic composition was prepared in Comparative example 2-4 in the same way as in Example 2-1, but by using herein, as the moisturizer , 3.0% of glycerin ("Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)), instead of 3.0% of the stachyose of Preparative example 1.
<Comparative example 2-5>
A cosmetic composition was prepared in Comparative example 2-5 in the same way as in Example 2-1, but by using herein, as the moisturizer, 3.0% of sodium pyrrolidone carboxylate ("PCA soda", from Aj inomoto Co . Ltd.), instead of 3.0% of the stachyose of Preparative example 1.
<Comparative example 2-6>
A cosmetic composition was prepared in Comparative example 2-6 in the same way as in Comparative example 2-1, but by replacing herein 5.01 of the 89.47% of purified water in Comparative example 2-1 with 5.0% of the polyhydric alcohol glycerin ("Concentrated glycerin for cosmetic compositions" , by Kao (Ltd. ) ) . <Comparative example 2-7>
A cosmetic composition was prepared in Comparative example 2-7 in the same way as in Comparative example 2-2, but by replacing herein 5.0% of the 89.47% of purified water in Comparative example 2-2 with 5.0% of the polyhydric alcohol glycerin ("Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)). ■cComparative example 2-8>
A cosmetic composition was prepared in Comparative example 2-8 in the same way as in Comparative example 2-3, but by replacing herein 5.0% of the 89.47% of purified water in Comparative example 2-3 with 5.0% of the polyhydric alcohol glycerin ("Concentrated glycerin for cosmetic compositions", by Kao (Ltd.)).
[Evaluation of skin moisturizing effect] The skin moisturizing effect of the cosmetic compositions of Examples 2-1 to2-5 and Comparat ive examples 2-1 to 2-8 was evaluated as follows: Ten female subjects in their twenties to fifties washed first their faces by the usual method and then applied themselves the cosmetic compositions on their cheeks, at a room temperature of 21°C and a relative humidity of 50%. The skin moisture content of the cheeks of the subjects three hours after application of the cosmetic composition was measured using a CORNEOMETER CM825 (by Integral Co. Ltd.) . The measurement results of skin moisture content are given in Table 3. The average values for each Example and Comparative example and "skin moisturizing effect" being the differences between each average values and reference value of 60 are given together in Table 3. Skin moisture content is an indicator of skin moisturizing effect and a larger numerical value of the skin moisture content denotes an enhanced skin moisturi zing effect .
[ Tabl e 3 ]
Skin
1 2 3 4 Average moistur-
5 6 7 8 9 10 value i zing
X effect
Example 2 -1 60 67 63 62 60 60 63 59 62 61 61 .7 + 2
Example 2 -2 65 66 62 62 61 62 60 61 63 63 62 .5 + 3
Example 2 -3 60 65 60 61 59 58 58 63 63 58 60 .5 + 1
Example 2 -4 64 65 63 66 66 65 63 66 64 63 64 .5 + 5
Example 2 -5 63 63 65 64 61 63 68 66 62 65 64 .6 + 5
Comparative 60 56 59 56 55 57 54 60 56 54 56 .7 -3 example 2 -1
Comparative 53 55 51 54 56 54 53 52 56 53 53 .7 -6 example 2 -2
Comparative 62 55 59 56 54 58 59 61 56 56 57 .6 -2 example 2 _ 2
Comparative 55 54 57 53 58 56 55 58 56 55 55 7 -4 example 2 _4
Comparative 60 58 62 56 57 60 57 60 55 58 58 3 -2 example 2
Comparative 61 57 59 54 56 56 57 60 57 55 57 2 -3 example 2 -6 1
Comparative 62 58 61 58 58 60 56 61 60 59 59 3 - 1 example 2 -7 !
ComparaI tive 60 57 62 59 55 61 58 62 59 58 59 1 - 1 example 2 -8 [Evaluating texture (sensory test)]
The texture of the cosmetic compositions of Examples
2-1 to 2-5 and Comparative examples 2-1 to 2-8 was evaluated as follows : Ten female subj ects in their twenties to fifties applied themselves the cosmetic compositions on their hands and faces, whereupon they judged the degree of stickiness on the skin that they felt. The texture of each cosmetic composition was evaluated in accordance with the evaluat ion criteria below, on the basis of the above judgment results . (Evaluation criteria for texture)
Number of subjects that indicate the composition was non-sticky
® : at least 9 individuals among the 10 subjects O: 7 or 8 individuals among the 10 subjects
Δ : 5 or 6 individuals among the 10 subjects x: 4 or fewer individuals among the 10 subjects
Table 4 summarizes the results of the evaluation of skin moisturizing effect and texture of Examples 2-1 to 2-5 and Comparative examples 2-1 to 2-8. [Table 4]
Figure imgf000032_0001
The results in Table 4 show that in Examples 2-1 to 2-5, corresponding to the cosmetic composition of the present invention, yielded a superior skin moisturizing effect and a superior texture (low degree of stickiness) vis-a-vis Comparative examples 2-1 to 2-8. Upon comparison of Example 2-1 and Comparative example 2-3, within both of which a tetrasaccharide galacto-oligosaccharide was used, it is indicated that galacto-oligosaccharides having fructose residues have superior skin moisturizing effect and texture vis-a-vis galacto-oligosaccharides having no fructose residues. Upon comparison of Examples 2-1 to 2-3 and Comparative examples 2-1 and 2-2, it transpires that among galacto-oligosaccharides having fructose residues, those with at least four monosaccharide units elicit a distinctly" superior skin moisturizing effect and markedly improved texture .
Moreover, the results of Examples 2-4 and 2-5 show that combining a polyhydric alcohol with a galacto-oligosaccharide having fructose residues further enhances the skin moisturizing effect of the galacto-oligosaccharide. On the other hand, the results of Comparative examples 2-6 and 2-8 indicate that the synergistic effect displayed in Examples 2-4 and 2-5 is not observed for other galacto-oligosaccharides (sucrose and the galacto-oligosaccharide of the Comparative preparative example) .
The cosmetic composition of the present invention, thus, is virtually free of the stickiness problem of conventional moisturizers, and elicits moreover a remarkably high skin moisturizing effect.
The cosmetic composition of the present invention has less stickiness, a superior texture and a improved skin moisturizing effect and can smoothen and hydrate the skin , and hence it is useful as a cosmetic composition embodied in a wide variety of forms.

Claims

What is claimed is:
1. A plant extract from Lamiaceae family flora, that contains galacto-ol igosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue .
2. A plant extract according to claim 1 , wherein said Lamiaceae family flora belongs to the Stachys or Lycopus genus .
3. A plant extract according to claim 1 or 2 , wherein said galacto-oligosaccharide is expressed by the following formula ( 1 ) ;
Gal- (Gal) n-Glc-Fru (1) wherein each Gal independently represents a galactose residue, GIc represents a glucose residue, Fru represents a fructose residue, and n represents an integer from 1 to 7.
4. A plant extract according to any one of claims 1 to 3, wherein said galacto-oligosaccharide is at least one from among stachyose, verbascose and ajugose.
5. A plant extract according to any of Claims 1 to 4, wherein the galacto-oligosaccharides as defined in
Claims 1 to 4 represent at least 70%, preferably at least 80%, for example at least 90%, of the total amount of galato-ol igosaccharides in the plant extract.
6. A cosmetic composition comprising a plant extract according to any of Claims 1 to 5.
7. A cosmetic composition comprising a galacto-ol igosaccharide that consists of 4 to 10 monosaccharide units and has at least one fructose residue .
8. The cosmetic composition according to Claim 7, wherein said galacto-oligosaccharide is expressed by the following formula (1) ;
Gal- (Gal) n-Glc-Fru (1) wherein each Gal independently represents a galactose residue, GIc represents a glucose residue, Fru represents a fructose residue, and n represents an integer from 1 to 7.
9. The cosmetic composition according to any one of claims 7 and 8, wherein said galacto-oligosaccharide is at least one from among stachyose, verbascose and ajugose.
10. The cosmetic composition according to any one of claims 7 and 9, wherein the cosmetic composition contains from 0.1 to 30wt%, preferably from 1 to 20wt% and more preferably from 3 to 10wt% of polyhydric alcohol.
11. A cosmetic skin care method for enhancing the barrier function of the skin, and/or enhancing moisturi zation of the skin, and/or strengthening the resistance of the skin to internal and/or external stress, and/or strengthening the resistance of the skin to pollution, and/or enhancing the brightness of the skin, comprising a step of applying the cosmetic composition according to any one of claims 6 to 10 to the skin.
12. A method for reducing or eliminating the sticky feel of a composition containing a polyhydric alcohol, comprising the step of mixing with said polyhydric alcohol at least one galacto-oligosaecharide as defined in any of Claims 7 to 9.
PCT/EP2008/056611 2007-06-04 2008-05-29 Cosmetic composition comprising galacto-oligosaccharides WO2008148694A1 (en)

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US11564879B2 (en) 2016-11-23 2023-01-31 Gojo Industries, Inc. Sanitizer composition with probiotic/prebiotic active ingredient
US11234997B2 (en) 2017-06-27 2022-02-01 Rottapharm Spa Antibacterial activity of galactooligosaccharide and xylitol in dermatological treatments
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