CA2112237C - Cosmetic compositions containing oligosaccharides - Google Patents

Cosmetic compositions containing oligosaccharides Download PDF

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Publication number
CA2112237C
CA2112237C CA002112237A CA2112237A CA2112237C CA 2112237 C CA2112237 C CA 2112237C CA 002112237 A CA002112237 A CA 002112237A CA 2112237 A CA2112237 A CA 2112237A CA 2112237 C CA2112237 C CA 2112237C
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Canada
Prior art keywords
composition
oligosaccharides
alpha
oligosaccharide
general formula
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Expired - Lifetime
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CA002112237A
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French (fr)
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CA2112237A1 (en
Inventor
Jean-Pierre H. G. Lamothe
Yves G. Marchenay
Piere F. Monsan
Francois M. B. Paul
Vincent Pelenc
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Bioeurope
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Bioeurope
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0034Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/02Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair

Abstract

Cosmetic compositions providing a suitable medium for the development of beneficial endogenous flora, and including at least one oligosaccharide selected from the group consisting of gluco-oligosaccharides, fructo-oligosaccharides, µ- and .beta.-galacto-oligosaccharides and mixtures thereof. Examples of compositions are liquid soap,shampoo, body lotion, face cream and vaginal gel.

Description

21~23'~
WC~ 93/00067 1 PCT/FR92/00597 Cosmetic compositions containin oligosaccharides The invention relates to cosmetic compositions containing oligosaccharides.
Man and animals are host to populations of microorganisms which develop naturally both at the surface and in the cavities of their bodies.
These microbial flora, or endogenous microflara, are characteristic of the species and of the region of the body where they develop. In close contact with their host, certain microorganisms are known to have a beneficial action on the skin or vaginal mucous membrane, for example by maintaining a slightly acidic environment and/or by participating in the protection of the organism against infections by pathogenic microorganisms which are present in small numbers or which are not usually present on the skin or an the vaginal mucous membrane.
It would therefore be useful to have available cosmetics which create a medium favorable for the development of the beneficial endogenous flora and I 5 which orient the metabolism of the whole endogenous microflora such that the said microflora participates in maintaining the good physico-chemical balance of the skin and the mucous membranes while not concomitantly favoring the development of pathogenic microorganisms:
During extensive research studies, the Applicant has found that certain oligosaccharides constitute products which can be easily metabolized by several a beneficial strains of the skin microrlora and of the vagina! flora. A
substantial gluco-oligosaccharide metabolism by non-pathogenic strains such as Micro-coccus kristinae, Micrococcus sedentarius, Staphylococcus capitis, Caryne-bacterium xerosis and Lactobacillus perrtasus has thus been observed during in vitro culture studies: On the other hand, pathogenic or opportunistic strains such as Staphylococcus aureus, Gardnerellavaginalis and Propionibacterium acnes do not metabolize, or very slightly metabolize these oligosaccharides.
Furthermore, it has also beer observed that, in the presence of these oligosaccharides, certain strains such as Lactobacillus pentosus, Micrococcus kristinae, Gardnerella vaginalis, Propionibacterium avidum and Propionibacterium granulosum, acidify the culture medium. Lactobacilli produce in particular lactic acid.

21I223°~
2 P~T/FR92/Od597 The invention therefore relates to cosmetic compositions, characterized in that they comprise at least one oligosaccharide chosen from the group consisting of gluco-oligosaccharides, fructo-oligosaccharides, a- and ,d~galacto-aligosaccharides and mixtures thereat.
Glucosaccharides which can be used in the cosmetic compositions of the invention are especially gluco-oligosaccharides corresponding to the general formula:
(O-a-D~glucopyranosyl)n A
where A is a residue of a glucose-accepting sugar chosen from maltose, isomaltose, isomaltotriose, methyl a-glucaside and glucose, and n ~ 1 to 10, the glucoside bonds being of the a(1-~6) and, optionally, cr(1-~2) and/or cr(1-~3) type, the a(1-a2) band, if present, being situated at the non-reducing end or constituting a branch point.
The above oligosaccharides can be produced by known processes for enzymatic synthesis by means of the enzyme glucosyl-transferase derived from the bacteria Leuconostoc mesenteroides, in the presence of sucrose and a glucose-accepting sugar chosen from maltose, isomaltose, isomaltotriose, methyl a glucoside and glucose.
Such processes are described in the literature, for example in EPA
0,325,872, by Paul et al. in Carbohydrate Research, 149 (1986), pages 433-44~
and in US-A-2,726;190. Strains of L~ueanostoc mesenteroides,r which are preferred for the implementation of the process of synthesis are the trains N
RRL
B-512(F) (for the production of gluco-oligosaCCharides with only a(1-~6) bonds) and NRRL B-1299 (for the production of gluco-aligosaccharides with cr(1-~6) and a(1-~2) bonds):
Maltose is most particularly preferred as glucose-accepting sugar.
Useful fructo-oligosaccharides, separately or in the form of a mixture, are especially hose corresponding to the general formula GFn or to the general for-mula Fm where G is a glucose residue, F'a fructose residue and n equals 1 to 10, in particular 2 to 4, and m equals 1 to 10, in particular 2 to 4. Such fructo-oligosaccharides exist in the natural'stat~ in a number of plants such as onion, garlic, artichoke, cf-~icory and the like. They' can be synthesized by the action, ~~~.~237 on sucrose, of a transfer enzyme, fructosyl transferase, extracted from an Aspergillus. Usefuf branched fructo-oligosaccharides can also be prepared from inulin from chicory roots by enzymatic processes, as described in WO-A1-91 13076.
Useful fructo-oligosaccharides (also called oligofructoses) are commercially available under the names Actilight~ (sold by Beghin-Meiji Industries, Paris, France) or Raftilosea (produced by Raffinerie Tirfemontoise, Tienen, Belgium).
Useful a-galacto-oligosaccharides, separately or in the form of a mixture, are especially those which possess a sucrose residue at one of their ends and correspond to the general formula:
(a-Gal(1 > 6))~ La-Glu(1 --> 2)~fi fructose,, sucrose where n equals 1 to 3, namely raffinose (n ~ 1), stachyose (n m 2) and verbascose (n ~ 3) which can be extracted from sc~yabean. Useful cr-galacto-oligosaccharides .are available commercially from the Japanese company Calpis Food industries. See also jP-A2-3 151 854 which describes these compounds.
Useful ~3-galacto-oligosaccharides, separ'atefy or in the form of a mixture, are especially those which possess a lactose residue at one of their ends and correspond to the formula:
(,13 - Gal (1 > a))~ \ ~3 - Gal (1 -> '4) glucose, '" ~Y"_' lactose where n ~ 1, 2 or 3 and a _ 2, 3; 4 and 6, the ,Q"(1 ----> 6) isomer being predorninant. Such /3-galacto-oligosaccharides can be obtained by enzymatic synthesis, for example by the action of ,Q-galactosidase in the presence of concentrated lactose, _ and are available commercially from the Japanese company Yal~ult Honsha. See also JP-A2-2 156 893 and EP-A-272 095 which describe these compocinds and their preparation.
By virtue of the presence of the oligosaccharide, the compositions of the invention make it possible to maintain a~ medium which is favorable for the development of the beneficial endogenous flora.
The quantity of oligosaccharide present in the cosmetic composition of the invention may range from 0.1 °/° by weight to 20°/° and more, preferably from 1 to 10°~ by weight. Below 0.196 by weight, the effect of the oligosaccharide becomes negligible. Furthermore, there is no particular advantage in incorporating more than 2096 by weight of oligosaccharide although this is pertectly possible.
Considerations of an economic nature also result in limiting the quantity of oligosaccharide to 2096 by weight, preferably to 109~o by weight, and very advantageously to 59~o by weight.
Usually, the oligosaccharide constituent will constitute a mixture of oligosaccharides insofar as the process for the manufacture of the compounds produce such mixtures.
In addition to the oligosaccharide constituent, the cosmetic compositions of the invention may contain the ingredients usually incorporated into this type of composition such as suitable carriers and other typical ingredients. It goes without saying, obviously, that it is advisable to avoid incorporating into the compositions ingredients whose properties would intertere with the desired aim which is to favor the development of the beneficial skin or vaginal microflora and the preservation of acidic conditions.
Thus, it is advisable to avoid incorporating bactericidal ingredients in proportions which would anhilate the endogenous microflora, or ingredients which confer a pronounced basic character on the composition.
For example, it will be good to avoid using high proportions of ionic surtace-active agents such as sodium lauryl sulfate, whose bactericidal properties are well known. If there is a need to incorporate a high proportion a surtace-active agent into the composition (for example in the case of liquid soap or a shampoo), a non-ionic surface-active agent such as an alkyl glucoside or a dialkyl ester will be used instead.
Nevertheless, incorporating into the compositions of the invention a small proportion (for example less than 1 % by weight) of preserving agent having a bacteriostatic and, optionally an antifungal action can be tolerated in order to allow the preservation of the said compositions for long periods.
Advantageously, the cosmetic compositions of the invention contain an acidic buffer which adjust the pH of the composition to the 5 to 7 range, preferably 5 to 8, such as a malic acid/sodium malate buffer, so as to favor rapid reimplantation of the microflora.

2~1~23°~
The oligosaccharides can be incorporated into a wide variety of cosmetic compositions such as liquid soap, shampoo, body milk, face cream, vaginal gel and the like.
These compositions can be easily prepared by techniques commonly used in the cosmetics industry.
In order to illustrate the invention, the following non-restrickive examples of cosmetic compositions according to the invention are given below.
In examples 1 to 5, the oligosaccharide constituent used was a rnixture of gluco-oligosaccharides produced by the company BIOEUROPE in accordance with the teachings of EP-A-0,325,872, using maltose as glucose-accepting sugar and glucosyl-transferase derived from the strain Leuconostoc mesenteroides NRLL B-1299. This mixture of glucose-oligosaccharides with a(1-~6) and a(1~2) bonds was predominantly made up of oligosaccharides with the degrees of polymerization 3 to 7 (n ~ 1 to 5).
in the examples, alf the proportions indicated are in % by weight.
Example 1 Liquid Soar Gluco-~oligosaccharides "Bioeurope" 5 Non-ionic surface-active agent (ORAMIX°NS10) 18 Thickener (Sepigel° 305) 2 Preservative (Sepicide°I-iB) 0.7 Malic acid/sodium malate buffer (qs pH 5.5) # 0.10 Water qs 100 Notes: ORAMIX°NS10 is an alkyl glucoside sold by the company SEPPIC.
SEPIGEL°305 is a thickening and stabilizing agent for emulsions sold by the company ~EPFIC, which is provided in the form of a neutral fluid emulsion:
It is a polymeric material referenced under the name: palyacrylamide (and) isoparaffin (end) laureth-7 (CTFA name).
SEPICiDE°HB is a liquid preserving agent, sold by the company SEPPIC, for the protection of health care and beauty products against microbial contamination. it consists of methyl; ethyl, propyl and butyl esters of para-hydroxybenzoic acid in combinationwith phenoxyethyi alcohol.

2~,~2~3'~
6 PCT/FR92/00597, Exarr~ple 2 Shampao Gluco-oligosaccharide "Bioeurope" 5 Surface-active agent of Ex. 1 10 Polysorbate 80 5 Preservative of Ex. 1 0.7 Buffer of Ex. 1 (qs pH 5.5) # 0.1 Water qs 100 Note : Polysorbate 80 is an emulsifier.a polyaxyethylene (20)-sorbitan It is monooleate.

Example 3 Bod~Milk (emulsion) Gluco-oligosaccharide "Bioeurope" 5 Cetyl and stearyl octanoate (fatty phase) 10 Polysorbate 80 3~~

Glycol palmitate (fatty phase) , 2.0 Thickener of Ex. 1 1.5 Sorbitan ester (emulsifying agent) 0.7 t' Preservative of Ex. 1 ~ 0.7 Buffer of Ex. 1 qs pH 6 Water , qs 100 Example 4 Face Cream (emulsion) Gluco-oligosaccharide "Bioeurope" 5 -Cetyl and stearyi octanoate (fatty phase) 3 2 5 Polysorbate 80 Microp~arl M 100 (pearlescent ageqt sold by the Japanese company Matsiumoto)3 Preservative of Ex:' 1 0.7 Buffer of Ex. 1 qs pH 6 Water qs 100 _ 211223' 7 . PCTlFR92/0(~597 Example 5 Va ig nil Cel Gluco-oligosaccharide "Bioeurope" 5 Thickener of Ex. 1 3 Preservative of Ex. 1 0.7 Buffer of Ex. 1 qs pH 6 Water qs 100 Example 6 Cosmetic compositions similar to those of Examples 1 to 5 were prepared except that the above described gluco-oligosaccharide "Bioeurope" was replaced by a gluco-oligosaccharide produced in a manner similar to gfuco-oligosaccharide "Bioeurope" but using the gfucosyl-transferase obtained from the strain Leuconostoc mesenteroides NRLL B-512(F).
The resultant gluco-oligosaccharide had duly a(1-~6) glucoside bands.
The cosmetic compositions thus produced had properties comparable to those of Examples 1-5 Example 7 Cosmetic compositions similar to those of Examples 1 to 5 were prepared except that the above-described gluco-oligosaccharide "Bioeurope" was replaced by identical quantities of the fructo-oligosaccharides Actilight~ P available from the company Beghin-Meiji Industries.
The cosmetic compositions'thus produced had properties comparable to those of Examples 1-5.
Example 8 Cosmetic compositions similar to those of Examples 1 to S were prepared except that the above-described gluCO-oli~osaccharide "Bioeurope" was replaced fly 25% higher quantities of the frtacto-oligosaccharide Raftilose°
L55; syrup.
(containing 80°/° dry extract).
Exam 1e 99 Cosmetic compositions similar to those of Examples 1 to 5 were prepared except that the above-described gluco-oiigosaecharide "Bioeurape" was replaced by similar quantities of the a-galacto-oligosaccharides extracted fram soyabean available from the company Ca[pis Food Industry Co., Ltd.

211~~3°~

Ex_ amr~le 1 U
Cosmetic compositions similar to those of Examples 1 to 5 were prepared except that the above-described gluco-oligosaccharide "gioeurope" was replaced by similar quantitir~s of the /3-galacto-oligosaccharides available from the Japanese company Yakult Honshu.
The cosmetic compositions thus produced had properties comparable to those of Examples 1 - 5, 1t goes without saying that the embodiments described are merely examples and they can be modified, especially by substitution of equivalent 1 U techniques, without as a result departing from the framework of the invention.

Claims (7)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A composition which favours the development of beneficial skin or vaginal microflora, said composition comprising at least 0.1% by weight of at least one oligosaccharide selected from the group consisting of gluco-oligosaccharides of the general formula:
(O-.alpha.-D-glucopyranosyl)n-A
wherein A is a residue of a glucose-accepting sugar selected from the group consisting of maltose, isomaltose, isomaltotriose, methyl .alpha.-glucoside and glucose, and n=1 to 10, the glucoside bonds being of the .alpha.(1-6) and optionally, .alpha.(1-2) and/or a(1-3) type, the optional .alpha.(1-2) bond being situated at a non-reducing end of the oligosaccharide molecule or constituting a branching point of said molecule;
fructo-oligosaccharides of the general formula GFn or an oligosaccharide of the general formula, Fm wherein G is a glucose residue, F a fructose residue, n=1 to 10 and m=1 to 10;
.alpha.-galacto-oligosaccharides of the general formula:
(.alpha.-Gal(1-6)n .alpha.-Glu(1-2).beta.-fructose, wherein n=1, 2 or 3;
.beta.-galacto-oligosaccharides of the general formula (.beta.-Gal(1-a))n .beta.-Gal(1-4)glucose wherein n=1, 2 or 3 and a=6 and 2, 3 or 4;
and mixtures thereof;
and a carrier;
said composition having a pH of 5 to 7.
2. The composition according to claim 1, wherein said composition comprises from 0.1 to 20% by weight of said oligosaccharide.
3. The composition according to claim 1 or 2, wherein said composition further comprises a non-ionic surface-active agent.
4. The composition according to any one of claims 1 to 3, wherein said composition further comprises a buffer which maintains the pH at 5 to 7.
5. The composition according to any one of claims 1 to 4, wherein said composition is applied in the form of a liquid soap, a shampoo, a body milk, a face cream or a vaginal gel.
6. Use of the composition of any one of claims 1 to 5, for favouring the development of beneficial skin or vaginal microflora.
7. Use of the composition of any one of claims 1 to 5, for favouring the development of at least one strain selected from the group consisting of Micrococcus kristinae, Micrococcus sedentarius, Staphylococcus capitis, Corynobacterium xerosis and Lactobacillus pentosus.
CA002112237A 1991-06-27 1992-06-26 Cosmetic compositions containing oligosaccharides Expired - Lifetime CA2112237C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR91/07955 1991-06-27
FR9107955A FR2678166B1 (en) 1991-06-27 1991-06-27 COSMETIC COMPOSITIONS CONTAINING GLUCOOLIGOSACCHARIDES.
PCT/FR1992/000597 WO1993000067A1 (en) 1991-06-27 1992-06-26 Cosmetic compositions containing oligosaccharides

Publications (2)

Publication Number Publication Date
CA2112237A1 CA2112237A1 (en) 1993-01-07
CA2112237C true CA2112237C (en) 2003-02-18

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CA002112237A Expired - Lifetime CA2112237C (en) 1991-06-27 1992-06-26 Cosmetic compositions containing oligosaccharides

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US (1) US5518733A (en)
EP (1) EP0591443B1 (en)
JP (1) JP3366632B2 (en)
KR (1) KR100229589B1 (en)
AU (1) AU2243492A (en)
CA (1) CA2112237C (en)
DE (1) DE69214815T2 (en)
ES (1) ES2097342T3 (en)
FR (1) FR2678166B1 (en)
WO (1) WO1993000067A1 (en)

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FR2678166A1 (en) 1992-12-31
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EP0591443B1 (en) 1996-10-23
EP0591443A1 (en) 1994-04-13
AU2243492A (en) 1993-01-25
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CA2112237A1 (en) 1993-01-07
ES2097342T3 (en) 1997-04-01
JP3366632B2 (en) 2003-01-14
FR2678166B1 (en) 1993-10-22
US5518733A (en) 1996-05-21
JPH06508832A (en) 1994-10-06
KR100229589B1 (en) 1999-11-15

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