FR2609998A1 - NOVEL ANTIOXIDANT SUBSTANCES DERIVED FROM AMINO ACIDS - Google Patents
NOVEL ANTIOXIDANT SUBSTANCES DERIVED FROM AMINO ACIDS Download PDFInfo
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- FR2609998A1 FR2609998A1 FR8700882A FR8700882A FR2609998A1 FR 2609998 A1 FR2609998 A1 FR 2609998A1 FR 8700882 A FR8700882 A FR 8700882A FR 8700882 A FR8700882 A FR 8700882A FR 2609998 A1 FR2609998 A1 FR 2609998A1
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- acid
- lipoamino
- lysine
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- arginine
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0042—Preserving by using additives, e.g. anti-oxidants containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/447—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof containing sulfur
-
- 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
- A61K8/64—Proteins; Peptides; Derivatives or degradation products 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A61K8/65—Collagen; Gelatin; Keratin; Derivatives or degradation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
- C09K15/22—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen containing an amide or imide moiety
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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- Oil, Petroleum & Natural Gas (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Wood Science & Technology (AREA)
- Dermatology (AREA)
- Materials Engineering (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
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Abstract
L'INVENTION CONCERNE DE NOUVELLES COMPOSITIONS DOUEES DE PROPRIETES ANTIOXYDANTES, CARACTERISEES EN CE QU'ELLES CORRESPONDENT A DES ASSOCIATIONS DE LIPOAMINOACIDES AVEC LA LYSINE OU L'ARGININE, AINSI QU'AUX LIPOAMINOACIDES COMPORTANT LA METHIONINE ACYLEE PAR DES CHAINES GRASSES DE C4 A C32, SATUREES OU INSATUREES.THE INVENTION RELATES TO NEW COMPOSITIONS HAVING ANTIOXIDANT PROPERTIES, CHARACTERIZED IN THAT THEY CORRESPOND TO ASSOCIATIONS OF LIPOAMINOACIDS WITH LYSINE OR ARGININE, AS WELL AS LIPOAMINOACIDS COMPRISING ACYLINE ACETYLATED WITH METHYLIN ACIN SATURATED OR UNSATURATED.
Description
I L J2609998I L J2609998
De nombreux travaux modernes montrent toute l'importance qu'il faut biologiquement Many modern works show all the importance that it takes biologically
attribuer aux lipoperoxydes et aux radicaux libres qui en sont issus. attribute to the lipoperoxides and to the free radicals which result therefrom.
De multiples publications indiquent que les peroxydes,comme les radicaux libres, jouent un role déterminant dans la formation de nombreux états pathologiques ainsi que dans le processus de vieillissement. Numerous publications indicate that peroxides, like free radicals, play a determining role in the formation of many pathological states as well as in the aging process.
Il est connu que la peroxydation des lipides,conduit à la formation de malonadial- It is known that lipid peroxidation leads to the formation of malonadial-
déhyde,qui a son tour réagit avec diverses structures,comme-les phosphoaminolipides dehyde, which in turn reacts with various structures, such as phosphoaminolipids
et acides aminés par exemple,pour donner lieu à un pigment fluorescent dénommé lipo- and amino acids for example, to give rise to a fluorescent pigment called lipo-
fuscine,que l'on trouve dans les tissus agés aussi bien animaux que végétaux. fuscine, which is found in old animal and plant tissues.
Récemment,il a été montré que les antioxydants jouaient un role important sur la longévité humaine comme animale et que,la superoxyde dismutase, pouvait être considérée comme le plus important agent de défense de 1 'organisme contre les effets toxiques du Recently, it has been shown that antioxidants play an important role in human and animal longevity and that, superoxide dismutase, can be considered as the most important defense agent of the organism against the toxic effects of
métabolisme de l'oxygène. (KUNIO YAGI-Lipids peroxides in biology an médicine-Acade- oxygen metabolism. (KUNIO YAGI-Lipids peroxides in biology an medicine-Acade-
mic Press 1982) (FRIDOVICH I- Adv in enzymology 1986) (MEHLBORN R-COLE GAdv Free Radical Biology & medicine i98S) (CUTLER R- antioxidants and longevity of mammalian mic Press 1982) (FRIDOVICH I- Adv in enzymology 1986) (MEHLBORN R-COLE GAdv Free Radical Biology & medicine i98S) (CUTLER R- antioxidants and longevity of mammalian
species- Life Sci.1985).species- Life Sci. 1985).
Nombreuses sont les publications concernant la formation des peroxydes et des There are many publications concerning the formation of peroxides and
moyens de les combattre par des antioxydants.C'est ainsi que l'utilisation d'anti- ways to combat them with antioxidants. This is how the use of anti
oxygène en alimentation humaine et animale est une nécessité sur le plan physiolo- oxygen in human and animal food is a physiological necessity
gique comme économique et, à cet égard un certain nombre de substances sont légale- economic and, in this respect, a number of substances are legal-
ment utilisées,comme le tocophérol,les gallates,ascorbates et, principalement les butyhydroxyanisol ou B H A et butylhydroxytoluène ou B H T. Il a été montré dans notre demande de brevet N 85 14536,que les associations acides gras-acides aminés basiques étaient douées de propriétés antioxydantes. La présente invention concerne de nouvelles substances antioxydantes,caractérisées en ce qu'elles comportent certains lipoaminoacides ou certaines de leur association avec des acides aminés basiques,comme la lysine et l'arginine,qui selon les cas,pourront être avantageusement utilisées pour la protection contre la dégradation oxydative des émulsions contenant des lipides,ou pour la protection des huiles et des graisses ment used, such as tocopherol, gallates, ascorbates and, mainly butyhydroxyanisol or BHA and butylhydroxytoluene or BH T. It has been shown in our patent application N 85 14536, that the fatty acid-basic amino acid associations were endowed with properties antioxidants. The present invention relates to new antioxidant substances, characterized in that they comprise certain lipoamino acids or some of their association with basic amino acids, such as lysine and arginine, which, depending on the case, may be advantageously used for protection against oxidative degradation of emulsions containing lipids, or for the protection of oils and fats
végétales ou animales.vegetable or animal.
-2- Selon la nature des corps gras ou des compositions en renfermant qu'il est indispensable de protéger contre l'auto-oxydation,nous aurons gràce à la présentE invention,un certain nombre de structures à caractère strictement biologique du fait que les constituants de ce type d'antioxydants,se trouvent normalement dans l'organisme;qu'ils sont dénués d'action toxique et qu'ils peuvent,de plus être considérés comme des nutriments.Ce type d'antioxydants est caractérisé par de -2- Depending on the nature of the fatty substances or of the compositions containing it which is essential to protect against auto-oxidation, we will have, thanks to the present invention, a certain number of structures of a strictly biological nature due to the fact that the constituents of this type of antioxidants, are normally found in the body; that they are devoid of toxic action and that they can, moreover, be considered as nutrients. This type of antioxidants is characterized by
puissantes propriétés antioxygàne,parfois plus élevées,que celles des plus act- powerful antioxidant properties, sometimes higher, than those of the most active
ifs antioxygènes de synthèse.,utilisés aux doses légales pour la protection des yew synthetic antioxidants, used at legal doses for the protection of
graisses,tels les B H T et B H A précédemment évoqués. fats, such as the B H T and B H A previously mentioned.
Afin de déterminer l'activité antioxydante des différentes structures bio- In order to determine the antioxidant activity of the different bio- structures
logiques faisant l'objet de l'invention,on aura recours à une exposition aux radiations U.V.(252 nm),durant quinze heures,à des températures,selon les cas de 50 à 60 .Les huiles,graisses ou émulsions,à raison de 10 g par essai,sont placées dans des petites boites de Pétri de même diamètre,qui seront ainsi logic subject of the invention, use will be made of exposure to UV radiation (252 nm), for fifteen hours, at temperatures, depending on the case from 50 to 60. Oils, fats or emulsions, at a rate of 10 g per test, are placed in small Petri dishes of the same diameter, which will thus be
irradiées à des températures accélerant le processus de peroxydation. irradiated at temperatures accelerating the peroxidation process.
Après irradiation,on prélève I g de la substance,qu'on introduit dans un ballon de IOO ml,muni d'un bouchon et d'un tube de verre de 50 cm environ. On y After irradiation, I g of the substance are taken, which is introduced into a 100 ml flask, fitted with a stopper and a glass tube of approximately 50 cm. We
ajoute I g d'Iodure de Potassium et 25 ml d'un mélange d'acide acétique/chloro- add I g of potassium iodide and 25 ml of a mixture of acetic acid / chloro-
forme:3/2. On porte le ballon muni de son tube dans une enceinte noire, pour shape: 3/2. We carry the balloon with its tube in a black enclosure, to
tre à l'abri de la lumière,on amène a ébullition durant trois minutes exacte- protect from light, bring to the boil for three minutes exactly-
ment.La solution est refroidie,puis additionnée d'une cinquantaine de ml d'eau et quelques gouttes d'empoi d'amidon.On titre avec une solution d'hyposulfite de sodium N/200,jusqu'à ce que la solution devienne incolore.Le nombre de ml consom The solution is cooled, then added with about fifty ml of water and a few drops of starch solution. Titrate with a solution of sodium hyposulfite N / 200, until the solution becomes colorless The number of ml consumed
més pour neutraliser l'iode libéré,correspond à l'indice de peroxyde de la sub- set to neutralize the released iodine, corresponds to the peroxide index of the sub-
stance,indiqué dans les tableaux par lettre A.En fonction de l'indice du témoin stance, indicated in the tables by letter A. Depending on the witness index
n'ayant pas reçu d'antioxygène,on calcule aisément l'indice de protection, indi- not having received an antioxidant, the protection index is easily calculated,
qué par la lettre B.qué by the letter B.
Les recherches effectuées par rapport à la nature des huiles ou des grais- Research carried out in relation to the nature of the oils or
ses,et en fonction des structures lipoaminoacides étudiées,montrent que: 1-Les structures lipoaminoacides sont généralement de faibles antioxygène dans ses, and depending on the lipoamino acid structures studied, show that: 1-Lipoamino acid structures are generally weak antioxidants in
les huiles comme dans les graisses.oils as in fats.
3 26099983 2609998
2- Que la combinaison lipoaminoacides-acides aminés basiques comme la lysine et l'arginine,conduit à des antioxydants très actifs,mais ne peuvent être utilisés 2- That the combination lipoamino acids and basic amino acids such as lysine and arginine, leads to very active antioxidants, but cannot be used
dans les graisses en raison de leur insolubilité. in fats due to their insolubility.
3- Que les lipoaminoacides obtenus par acylation de chaines grasses saturées ou insaturées avec la méthionine,sont doués de puissantes propriétés antioxydantes; que de telles structures présentent un avantage tout particulier,du fait de la nature des constituants qui sont les éléments fondamentaux de la matière vivante;qu' enfin,de par leur nature biologique,ce type d'antioxygène est caractérisé par des 3- That the lipoamino acids obtained by acylation of saturated or unsaturated fatty chains with methionine, are endowed with powerful antioxidant properties; that such structures have a very particular advantage, due to the nature of the constituents which are the fundamental elements of living matter; that finally, by their biological nature, this type of antioxidant is characterized by
propriétés nutritionnelles.nutritional properties.
L'invention est donc caractérisée en ce qu'elle comporte des structures lipo- The invention is therefore characterized in that it comprises lipo- structures
aminoacides,douées de propriétés antioxydantes,répondant aux formules suivantes: 1) lipoaminoacide lysine: R-CH-COOH,H2N- ( CH2)4-CH- COOH amino acids, endowed with antioxidant properties, corresponding to the following formulas: 1) lysine lipoamino acid: R-CH-COOH, H2N- (CH2) 4-CH- COOH
I NHI NH
NH 2NH 2
CO-R' 2) Lipoaminoacide arginine: R-CH-COOH,H2N-C- NH-(CH2) 3-CH-COOH CO-R '2) Lipoamino acid arginine: R-CH-COOH, H2N-C- NH- (CH2) 3-CH-COOH
NH NH NHNH NH NH
N2 CO-R' Dans lesquelles R= un radical d'un acide aminé R'=un radical d'une chaîne grasse saturée ou insaturée de C4 à C32 3) Lipoaminoacide de méthionine: CH3-S-CH2-CH2 -CH-COOH N2 CO-R 'In which R = a radical of an amino acid R' = a radical of a saturated or unsaturated fatty chain from C4 to C32 3) Methionine lipoamino acid: CH3-S-CH2-CH2 -CH-COOH
3 2 2 13 2 2 1
NH CO-R Dans laquelle R= un radical gras saturé ou insaturé de C4 à C32 Les tableaux 1 et 2 montrent 1 'effet protecteur d'associations de lipoaminoacides avec la lysine et l'arginine,à raison de 2,5% dans différentes huiles végétales NH CO-R In which R = a saturated or unsaturated fatty radical from C4 to C32 Tables 1 and 2 show the protective effect of associations of lipoamino acids with lysine and arginine, at 2.5% in different vegetal oils
- comparativement aux lipoaminoacides non associés avec les acides aminés basiques. - compared to lipoamino acids not associated with basic amino acids.
Le B H T (E 321) utilisé comme référence à 0,2% est donc a une teneur très éloignée de la teneur légale qui est de 0,OI% (arrêté du 7 Aout 1962) puis, de 150 ppm,suite à The B H T (E 321) used as a reference at 0.2% is therefore at a content very far from the legal content which is 0, OI% (decree of August 7, 1962) then, of 150 ppm, following
L'_arrété du 16 Mars 1977).The order of March 16, 1977).
TABLEAU N 1TABLE N 1
Substances essayées Huile de Tournesol huile de Sésame Huile d'amandes douce Substances tested Sunflower oil Sesame oil Sweet almond oil
A B A B A BA B A B A B
Huiles témoins 6,6 5,8 9;2Control oils 6.6 5.8 9; 2
B H T à 0,2% 5,5 17% 2,5 57% 2,7. 71% B H T at 0.2% 5.5 17% 2.5 57% 2.7. 71%
Pcide palmitoylkeratinique 4,9 26% 3,0 48% 3,6 61% Palmitoylkeratinate de lysine 0,9 86% 0,1 98% 0,1 99% Acide palmitoylcaséinique 3,8 42% 2,4 55% 4,2 54% Palmitoylcaséinate de lysine 0,8 88% 0,1 99% 0,1 99% Io0 Acide palmitoylcollagénique 5,7 14% 3,3 43% 3,8 59% Palmitoylcollagénate de lysine 0,6 91% 0,6 90% 0,1 99% Acide palmitoylcystinique (+) 1,8 73% 1,0 83% 0,9 90% Palmitoylcystinate de lysine 0,1 99% 0,1 99% 0,1 99% Acide butyryllysinique 5,5 17% 4,3 26% 8,2 11% Butyryllysinate de lysine 0,7 89% 0,5 90% 1,5 84% Butyrylcystinate de lysine 0,8 84% 0,7 88% 1,8 80% Palmitoylkeratinic acid 4.9 26% 3.0 48% 3.6 61% Lysine palmitoylkeratinate 0.9 86% 0.1 98% 0.1 99% Palmitoylcaseinic acid 3.8 42% 2.4 55% 4.2 54% Lysine palmitoylcaseinate 0.8 88% 0.1 99% 0.1 99% Io0 Palmitoylcollagenic acid 5.7 14% 3.3 43% 3.8 59% Lysine palmitoylcollagenate 0.6 91% 0.6 90 % 0.1 99% Palmitoylcystinic acid (+) 1.8 73% 1.0 83% 0.9 90% Lysine palmitoylcystinate 0.1 99% 0.1 99% 0.1 99% Butyryllysinic acid 5.5 17 % 4.3 26% 8.2 11% Lysine butyryllysinate 0.7 89% 0.5 90% 1.5 84% Lysine butyrylcystinate 0.8 84% 0.7 88% 1.8 80%
TABLEAU N 2TABLE N 2
Témoins huiles 7,5 5,2 9,2Oil indicators 7.5 5.2 9.2
B H T à 0,2% 5 33% 3,6 31% 2,7 71%B H T at 0.2% 5 33% 3.6 31% 2.7 71%
Acide palmitoylkératinique 4,5 40%5 1,0 80% 3,6 61% Palmitoylkératinate d'arginine 0,1 99% 0,1 99% 0,7 93% Acide palmitoylcaséinique 5,4 28% 1,3 75% 4,2 54% Palmitoylcaséinate d'arginine 0,1 99% 0,1 99% 0,1 99% Acide palmitoylcollagénique 6,2 17% 2,2 58% 3,8 59% Palmitoylcollagénate d'arginine 0,3 94% 0,1 99% 0,6 93% Acide palmitoylcystinique (+) 2,4 68% 0,8 85% 0,9 80% Palmitoylkeratinic acid 4.5 40% 5 1.0 80% 3.6 61% Arginine palmitoylkeratinate 0.1 99% 0.1 99% 0.7 93% Palmitoylcaseinic acid 5.4 28% 1.3 75% 4 , 2 54% Arginine palmitoylcaseinate 0.1 99% 0.1 99% 0.1 99% Palmitoylcollagenic acid 6.2 17% 2.2 58% 3.8 59% Arginine palmitoylcollagenate 0.3 94% 0 , 1 99% 0.6 93% Palmitoylcystinic acid (+) 2.4 68% 0.8 85% 0.9 80%
Palmitoylcystinate-Palmitoylcystinate-
d'arginine 1,1 86% 0,3 94% 0,6 94% (+) difficilement soluble,nécessite un chauffage trop élevé altérant l'huile arginine 1.1 86% 0.3 94% 0.6 94% (+) sparingly soluble, requires too high heating to alter the oil
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-s- 2609998-s- 2609998
Le tableau c-après montre la protection de quatre huiles végétales par diffé- The table below shows the protection of four vegetable oils by different
rents acides lipométhioniques,après 15 heures d'irradiation U V à 60 rents lipomethionic acids, after 15 hours of irradiation U V to 60
TABLEAU N 3TABLE N 3
Substances essayées H. de tournesol H.de noisette H. de sésame H. d'amandes douces Substances tested H. sunflower H. hazelnut H. sesame H. sweet almonds
__________________________________________________________________________ __________ __________________________________________________________________________ __________
A B A B A B A BA B A B A B A B
Témoins huiles 13 20,2 6,9 15Oil witnesses 13 20.2 6.9 15
B H T à 0,2% 7,7 41% 11 46% 5,9 15% 7 53% B H T at 0.2% 7.7 41% 11 46% 5.9 15% 7 53%
Acide palmitoylméthioniquePalmitoylmethionic acid
à 25 1,9 86% 1,0 95% 0,9 87% 1,0 94% at 25 1.9 86% 1.0 95% 0.9 87% 1.0 94%
Acide caprylylméthioniqueCaprylylmethionic acid
1,9 86% 1,0 95% 0,6 91% 1,2 92%..DTD: Acide lauroylméthionique 1,9 86% 1,0 95% 0,8 89% 1,2 92% iI ii Acide butyrvlméthionique 2,0 85% 1,2 95% 0,8 89% 1,8 88% e5... Acide oléoylméthionique le 0,8 94% 0,8 96% 0,4 94% 0,7 95% Le tableau suivant montre la protection de trois graisses différentes par les acides lipométhioniques à des teneurs de 3%,2% et 1%,comparativement au BHT à 0, 2% et un dérivé acylé de la sarcosine,qui biochimiquement n'est pas un lipoaminoacide 1.9 86% 1.0 95% 0.6 91% 1.2 92% .. DTD: Lauroylmethionic acid 1.9 86% 1.0 95% 0.8 89% 1.2 92% iI ii Butyrvlmethionic acid 2.0 85% 1.2 95% 0.8 89% 1.8 88% e5 ... Oleoylmethionic acid le 0.8 94% 0.8 96% 0.4 94% 0.7 95% The following table shows the protection of three different fats by lipomethionic acids at 3%, 2% and 1%, compared to 0, 2% BHT and an acylated derivative of sarcosine, which biochemically is not a lipoamino acid
TABLEAU N 4TABLE N 4
__________________________________________________________________________ __________- __________________________________________________________________________ __________-
Substances essayées Saindoux Suif brut Suif raffiné Substances tested Lard Raw tallow Refined tallow
__________________________________________________________________________ _____ __________________________________________________________________________ _____
A B A B A BA B A B A B
Témoins graisses 31,5 3,5 14Fat indicators 31.5 3.5 14
B H T à 0,2% 2,3 93% 1,5 58% 1,5 89% B H T at 0.2% 2.3 93% 1.5 58% 1.5 89%
Acide PalmitoylméthioniquePalmitoylmethionic acid
à 3% 3,2 90%/0 1,0 72% 1,6 89%at 3% 3.2 90% / 0 1.0 72% 1.6 89%
" " à 2% 3,2 90% 1,2 66% 1,7 88%"" at 2% 3.2 90% 1.2 66% 1.7 88%
310" " à 1% 9,7 69% 2,1 40(/0 4,5 68% 310 "" at 1% 9.7 69% 2.1 40 (/ 0 4.5 68%
Acide caprylyl fi.Caprylyl acid fi.
à 3% 3,1 90% 1,2 66% 1,9 87%at 3% 3.1 90% 1.2 66% 1.9 87%
". . à 2% 3,1 90% 1,2 66% 2,0 86%".. to 2% 3.1 90% 1.2 66% 2.0 86%
"I" à 1% 5,4 83% 1,6 55% 4,9 65%"I" at 1% 5.4 83% 1.6 55% 4.9 65%
Acide lauroyl " "Lauroyl acid ""
à 3% 3,2 90% 1,0 72% 1,4 90%at 3% 3.2 90% 1.0 72% 1.4 90%
" à 2% 3,2 90% 1,1 69% 2,O0 86%"at 2% 3.2 90% 1.1 69% 2, O0 86%
" à 1% 6,8 78% 2,2 37% 5,0 65%"at 1% 6.8 78% 2.2 37% 5.0 65%
Acide butyryl..Butyryl acid ..
à 3% 5,2 84% 1,3 63% 4,0 72%at 3% 5.2 84% 1.3 63% 4.0 72%
" à 2% 5,6 83% 1,3 63% 4,9 64%"at 2% 5.6 83% 1.3 63% 4.9 64%
" à 1% 12,2 62% 2,3 35% 6,0 57%"at 1% 12.2 62% 2.3 35% 6.0 57%
Acide oléoyl ".Oleoyl acid ".
4^5 à 3% 0,1 99% OO I0/0% 0,9 94%4 ^ 5 to 3% 0.1 99% OO I0 / 0% 0.9 94%
à 2% 0,3 98% 00 100% 0,9 94%at 2% 0.3 98% 00 100% 0.9 94%
Lauroylsarcosine à 3% 26,7 15% 4,7 - 13,7 - Lauroylsarcosine 3% 26.7 15% 4.7 - 13.7 -
-6- Le tableau suivant nous montre la faible protection antioxydante de quelques exemples de lipoaminoacides,concernant le suif raffiné, comparativement au tableau N 4 -6- The following table shows us the weak antioxidant protection of some examples of lipoamino acids, concerning refined tallow, compared to table N 4
TABLEAU N 5TABLE N 5
A BA B
Témoin 11Witness 11
BHT à 0,2% 2 82%0.2% BHT 2 82%
Acide palmitoylcollagéniquePalmitoylcollagenic acid
à 2% 7,2 35%at 2% 7.2 35%
Acide palmitoylcaséiniquePalmitoylcaseinic acid
"... 5 55%"... 5 55%
Acide palmitoylkératinique il.I 4,7 58% Palmitoylkeratinic acid il.I 4.7 58%
Acide palmitoylhydroxyproli-Palmitoylhydroxyproli- acid
nique.. 10,5 0,5% Acide Palmitoylcystinique I" t 9,7 1,4% Acide Palmitoylprolinique 10.5 0.5% Palmitoylcystinic acid I "t 9.7 1.4% Palmitoylprolinic acid
" 10,5 0,5%"10.5 0.5%
Acide Palmitoyl phénylalanique 9,8 1,2% Le tableau ci-après nous montre l'évolution de la peroxydation 8 jours après irradiation du suif raffiné, dont les chiffres initiaux figurent dans le tableaix4 Palmitoyl phenylalanic acid 9.8 1.2% The table below shows the evolution of peroxidation 8 days after irradiation of refined tallow, the initial figures of which appear in table 4
TABLEAU N 6TABLE N 6
______________________________________________________________________________ ______________________________________________________________________________
Substances essayées immédiatement après 8 jours après irradiation UV Substances tested immediately after 8 days after UV irradiation
A B A BA B A B
Témoin I4 24,5Witness I4 24.5
BH T à 0,2% 1,5 89% 1,9 93%BH T at 0.2% 1.5 89% 1.9 93%
Acide palmitoylméthionique à % 1,6 89% 1,9 93% i. à 2% 1,7 88% 2,1 91% Acide caprylyl '. à 3% 1,9 87% 2,5 90% Palmitoylmethionic acid at 1.6% 89% 1.9 93% i. at 2% 1.7 88% 2.1 91% Caprylyl acid. at 3% 1.9 87% 2.5 90%
'. à 2% 2,0 86% 2,0 92%'. at 2% 2.0 86% 2.0 92%
Acide lauroyl " " à 3% 1,4 90% 2,8 89% Lauroyl acid "" at 3% 1.4 90% 2.8 89%
" à 2% 2,0 86% 2,2 91%"at 2% 2.0 86% 2.2 91%
Acide Oléoyl ". à 3% 0,8 94% 1,1 95% - Oleoyl acid ". At 3% 0.8 94% 1.1 95% -
. à 2% 0,8 94% 1,1 95%..DTD: Comme on le voit,à la lumière de ces tableaux,il est surprenant qu'une chaine . at 2% 0.8 94% 1.1 95% .. DTD: As we can see, in the light of these tables, it is surprising that a chain
grasse insaturée,tel l'acide oléique,facilement autooxydable,acylée à la méthio- unsaturated fat, such as oleic acid, easily self-rusting, acylated with methio-
nine,lui confère de remarquables propriétés antioxydantes.Il est également surpre- nine, gives it remarkable antioxidant properties.
nant que seuls,?7 les acides lipométhioniques assurent une protection importante pour les huiles végétales comme pour les graisses animales,ce qui n'est pas le cas pour l'un des plus puissants antioxydants,comme le B H T. -7- Comparaison d'activité protectrice de certains lipoaminoacides et de leurs dérivés d'arginine et de lysine,dans trois huiles émulsifiées. Huile:10%,alcool gras polyoxyéthyléné 1CO%,lipoaminoacide ou dérivé:5%:, QS Eau-I5 heures d'irradiation à .L'eau évaporée est remplacée.TABLEAU N 7 nant that only? 7 lipomethionic acids provide significant protection for vegetable oils as for animal fats, which is not the case for one of the most powerful antioxidants, such as BH T. -7- Comparison of protective activity of certain lipoamino acids and their arginine and lysine derivatives in three emulsified oils. Oil: 10%, polyoxyethylenated fatty alcohol 1CO%, lipoamino acid or derivative: 5% :, QS Water-I5 hours of irradiation with. Evaporated water is replaced. TABLE N 7
Nature des substances.Nature of substances.
sNature des substances Tournesol Noisette Sésame essayée __ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ Nature of the substances Sunflower Hazelnut Sesame tried __ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
A B A B A BA B A B A B
Témoins 18 9 4,4Witnesses 18 9 4.4
B H T à 0,2% 6,8 62% 2,8 69% 2,1 52% B H T at 0.2% 6.8 62% 2.8 69% 2.1 52%
Acide palmitoylcollagénique 8,5 53% 4,5 50% 3,6 18% Palmitoylcollagénate de lysine 4,5 75% 2,5 72% 2,0 55% " I d'arginine 4,2 77% 3,8 58% 2,2 50% Acide palmitoylkératinique 8,2 54% 3,7 57% 3,7 16% Paimitoylkératinate de lysine 3,2 82% 3,2 65% 2,2 50% 15. " d'arginine 3,1 83% 3,2 65% 2,4 45% Acide palmitoylcaseinique 7,8 57% 3,4 62% 3,4 33% Palmitoylcaséinate de lysine 3,5 80% 2,9 68% 2,0 55% .. d'arginine 3,2 82% 3,1 66% 2,3 75% Acide palmitoylcystinique 7,0 61% 3,2 65% 2,8 47% Palmitoylcystinate de lysine 4,5 75% 2,2 76% 2,6 61% Acide palmitoylhydroxyproliniq.10,3 43% 6, 0 33% 3,8 14% Palmitoylhydroxyprolinate de lysine 4,5 75% 4,2 53% 2,8 47% Palmitoylcollagenic acid 8.5 53% 4.5 50% 3.6 18% Lysine palmitoylcollagenate 4.5 75% 2.5 72% 2.0 55% "I of arginine 4.2 77% 3.8 58% 2.2 50% Palmitoylkeratinic acid 8.2 54% 3.7 57% 3.7 16% Lysine paimitoylkeratinate 3.2 82% 3.2 65% 2.2 50% 15. "of arginine 3.1 83 % 3.2 65% 2.4 45% Palmitoylcaseinic acid 7.8 57% 3.4 62% 3.4 33% Lysine palmitoyl casease 3.5 80% 2.9 68% 2.0 55% .. d arginine 3.2 82% 3.1 66% 2.3 75% Palmitoylcystinic acid 7.0 61% 3.2 65% 2.8 47% Lysine palmitoylcystinate 4.5 75% 2.2 76% 2.6 61 % Palmitoylhydroxyproliniq acid 10.3 43% 6.03% 3.8 14% Lysine palmitoylhydroxyprolinate 4.5 75% 4.2 53% 2.8 47%
Activité protectrice d'émulsions contenant 10% d'huile,par cinq acides lipométhio- Protective activity of emulsions containing 10% oil, by five lipomethio acids
nique aux teneurs de 2 et 02%fuck at 2 and 02%
_ ----------- - TABLEAU N 8 ____________ _ ----------- - TABLE N 8 ____________
Substances essayées Tournesol Noisette Substances tested Sunflower Hazelnut
__________________________________________________________________________ _____ __________________________________________________________________________ _____
A B A BA B A B
Témoin 23 6,5Witness 23 6.5
B H T à 0,2% 1,9 92% 2,9 53%B H T at 0.2% 1.9 92% 2.9 53%
Acide Palmitoylméthionique à 2% 1,5 95% 0,0 I00% " "Caprylyl " " 0,3 99% 0,0 100% " Lauroyl " " 0,3 99% 0,0 100% " Butyryl " " 4,5 80% 0,0 100% 35. 'Oléoyl " " 0,2 99% 0,0 100% Témoin 20,5 7,8 Palmitoylmethionic acid 2% 1.5 95% 0.0 100% "" Caprylyl "" 0.3 99% 0.0 100% "Lauroyl" "0.3 99% 0.0 100%" Butyryl "" 4, 5 80% 0.0 100% 35. 'Oléoyl "" 0.2 99% 0.0 100% Control 20.5 7.8
B H T à 0,02% 15,0 27% 6,7 24%B H T at 0.02% 15.0 27% 6.7 24%
Acide palmitoylméthionique à 0,2% 15,2 26% 5,5 30% Il Caprylyl ". 14,0 32% 5,8 26% " " Lauroyl " " 15,3 27% 5,9 25% ""Butyryl " " 14,8 28% 5,9 25% ""Oléoyl ""14,2 30% 5,5 30% -8- L'invention s'étend à toutes compositions cosmétiques,pharmaceutiques,alimentaires ou industrielles comportant des graisses ou des huiles d'origine animale (terrestre ou marine)ou d'origine végétale,ou encore d'origine minérale,qui seront protégées de la dégradation oxydative par incorporation de sels de lysine ou d'arginine de lipoaminoacides,ou par un lipoaminoacide issu de l'acylation d'une chaine grasse à 0.2% palmitoylmethionic acid 15.2 26% 5.5 30% Il Caprylyl ". 14.0 32% 5.8 26%" "Lauroyl" "15.3 27% 5.9 25%" "Butyryl" "14.8 28% 5.9 25%" "Oléoyl" "14.2 30% 5.5 30% -8- The invention extends to all cosmetic, pharmaceutical, food or industrial compositions comprising fats or oils of animal origin (terrestrial or marine) or of vegetable origin, or even of mineral origin, which will be protected from oxidative degradation by incorporation of lysine or arginine salts of lipoamino acids, or by a lipoamino acid derived from l acylation of a fatty chain to
la méthionine,conformément aux structures décrites page 3. methionine, in accordance with the structures described on page 3.
L'invention est caractérisée en ce qu'elle permet non seulement de protéger les The invention is characterized in that it not only protects the
corps gras contre la dégradation oxydative,mais de pouvoir introduire dans l'orga- fatty substance against oxidative degradation, but to be able to introduce into the organ-
nisme,des structures à caractère strictement biologique,en conformité avec celles qui y sont présentes,et de pouvoir ainsi s'opposer à l'influence des radicaux libres endogènes ou exogènes,responsables en grande partie de l'accélération du processus nism, strictly biological structures, in accordance with those present therein, and thus being able to oppose the influence of endogenous or exogenous free radicals, responsible in large part for the acceleration of the process
de vieillissement et de la genèse de multiples maladies. of aging and the genesis of multiple diseases.
Claims (2)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8700882A FR2609998B1 (en) | 1987-01-26 | 1987-01-26 | NOVEL ANTIOXIDANT SUBSTANCES DERIVED FROM AMINO ACIDS |
| GB08801560A GB2200633A (en) | 1987-01-26 | 1988-01-25 | Antioxygen agents |
| JP63015700A JPS63218649A (en) | 1987-01-26 | 1988-01-26 | Antioxidant amino acid base substance and antioxidant |
| DE3802216A DE3802216A1 (en) | 1987-01-26 | 1988-01-26 | ANTIOXIDIZERS DERIVED FROM AMINO ACIDS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8700882A FR2609998B1 (en) | 1987-01-26 | 1987-01-26 | NOVEL ANTIOXIDANT SUBSTANCES DERIVED FROM AMINO ACIDS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2609998A1 true FR2609998A1 (en) | 1988-07-29 |
| FR2609998B1 FR2609998B1 (en) | 1994-04-15 |
Family
ID=9347272
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8700882A Expired - Lifetime FR2609998B1 (en) | 1987-01-26 | 1987-01-26 | NOVEL ANTIOXIDANT SUBSTANCES DERIVED FROM AMINO ACIDS |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS63218649A (en) |
| DE (1) | DE3802216A1 (en) |
| FR (1) | FR2609998B1 (en) |
| GB (1) | GB2200633A (en) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2654107B1 (en) * | 1989-11-03 | 1995-03-31 | Jean Morelle | LIPOAMINOACIDS WITH NON-PEROXIDABLE FATTY CHAINS. |
| JPH03178913A (en) * | 1989-12-06 | 1991-08-02 | Shiseido Co Ltd | Skin external agent |
| FR2697159B1 (en) * | 1992-10-22 | 1995-01-13 | Oreal | Cosmetic or dermo-pharmaceutical composition containing in combination a lauroylmethionate of a basic amino acid and at least one polyphenol. |
| FR2747309B1 (en) * | 1996-04-16 | 1998-05-22 | Morelle Jean | NOVEL COMPOSITIONS FOR THE TREATMENT OF BURNS AND INJURIES, CONTAINING DIFFERENT ACYLAMINOACIDS AND LIPOYLAMINOACIDS |
| FR2779911B1 (en) * | 1998-06-17 | 2003-10-03 | Jean Morelle | COMPOSITIONS FOR THE PROTECTION OF PLANTS AGAINST OXIDATIVE STRESS |
| KR20010075000A (en) | 1998-10-09 | 2001-08-09 | 에가시라 구니오 | Cysteine derivatives |
| JPWO2002055073A1 (en) * | 2001-01-05 | 2004-05-13 | 協和醗酵工業株式会社 | Arthritis prevention agent |
| EP2833739B1 (en) * | 2012-03-30 | 2020-12-02 | Givaudan SA | N-acyl proline derivatives as food flavouring compounds |
| US10645955B2 (en) | 2012-03-30 | 2020-05-12 | Givaudan Sa | N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds |
| KR102068375B1 (en) | 2012-03-30 | 2020-01-20 | 지보당 에스아 | N-acyl-amino acid derivatives for improvement of the flavour profile edible compositions |
| WO2013149031A2 (en) | 2012-03-30 | 2013-10-03 | Givaudan S.A. | Powder flavour composition |
| BR112014024323B1 (en) | 2012-03-30 | 2020-03-10 | Givaudan Sa | COMPOSITIONS UNDERSTANDING N-ACYLATED CARBOXYLIC 1-AMINOCYCLEALKYL ACIDS, STANDARD SOLUTION AND USE |
| KR102045589B1 (en) | 2012-03-30 | 2019-11-15 | 지보당 에스아 | N-acyl-amino acid derivatives as food flavouring compounds |
| CA2868058C (en) * | 2012-03-30 | 2019-12-17 | Givaudan S.A. | N-acylated methionine derivatives as food flavouring compounds |
| WO2015050538A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| WO2015048991A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan Sa | Organic compounds having taste-modifying properties |
| US10674755B2 (en) | 2013-10-02 | 2020-06-09 | Givaudan S.A. | Organic Compounds |
| CN105658089B (en) | 2013-10-02 | 2019-07-09 | 奇华顿股份有限公司 | Organic compound |
| CN105636457B (en) | 2013-10-02 | 2020-03-10 | 奇华顿股份有限公司 | Organic compounds with taste-improving properties |
| US11122826B2 (en) | 2013-10-02 | 2021-09-21 | Givaudan Sa | Organic compounds |
| WO2015050535A1 (en) | 2013-10-02 | 2015-04-09 | Givaudan S.A. | Organic compounds |
| GB201317424D0 (en) | 2013-10-02 | 2013-11-13 | Givaudan Sa | Improvements in or relating to organic compounds |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52156787A (en) * | 1976-06-23 | 1977-12-27 | Shiseido Co Ltd | Oil-in-water type emulsified composition |
| JPS5352631A (en) * | 1976-10-22 | 1978-05-13 | Kouichi Ogawa | Cosmetics |
| FR2422400A1 (en) * | 1978-04-13 | 1979-11-09 | Morelle Jean | Compsns. for treating human lice - contg. an aminoacid acylated with a fatty acid |
| JPS5939818A (en) * | 1982-08-31 | 1984-03-05 | Lion Corp | Hair cosmetic |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL132126C (en) * | 1966-10-13 | |||
| JPS5919596B2 (en) * | 1980-02-13 | 1984-05-07 | 川研フアインケミカル株式会社 | New transparent solid cleaning agent |
| FR2587900B1 (en) * | 1985-10-01 | 1988-10-07 | Morelle Jean | BASIC FATTY-AMINO ACID ASSOCIATIONS WITH EMOLLIENT, EMULSIFIING AND ANTIOXIDANT PROPERTIES FOR COSMETICS, DERMATOLOGY AND FOOD |
-
1987
- 1987-01-26 FR FR8700882A patent/FR2609998B1/en not_active Expired - Lifetime
-
1988
- 1988-01-25 GB GB08801560A patent/GB2200633A/en not_active Withdrawn
- 1988-01-26 JP JP63015700A patent/JPS63218649A/en active Pending
- 1988-01-26 DE DE3802216A patent/DE3802216A1/en active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52156787A (en) * | 1976-06-23 | 1977-12-27 | Shiseido Co Ltd | Oil-in-water type emulsified composition |
| JPS5352631A (en) * | 1976-10-22 | 1978-05-13 | Kouichi Ogawa | Cosmetics |
| FR2422400A1 (en) * | 1978-04-13 | 1979-11-09 | Morelle Jean | Compsns. for treating human lice - contg. an aminoacid acylated with a fatty acid |
| JPS5939818A (en) * | 1982-08-31 | 1984-03-05 | Lion Corp | Hair cosmetic |
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| Title |
|---|
| CHEMICAL ABSTRACTS, vol. 101, no. 2, 9 juillet 1984, page 289, résumé no. 12017c, Columbus, Ohio, US; & JP-A-59 39 818 (LION CORP.) 05-03-1984 * |
| CHEMICAL ABSTRACTS, vol. 70, no. 9, 3 mars 1969, page 386, résumé no. 38057g, Columbus, Ohio, US; T. SCIORTINO et al.: "Antiviral activity. VIII. Higher N-acyl derivatives of some amino acids", & BOLL. CHIM. FARM. 1968, 107(8), 498-505 * |
| CHEMICAL ABSTRACTS, vol. 88, no. 18, 1er mai 1978, page 314, résumé no. 126184y, Columbus, Ohio, US; & JP-A-77 156 787 (SHISEIDO CO., LTD) 27-12-1977 * |
| CHEMICAL ABSTRACTS, vol. 89, no. 18, 30 octobre 1978, page 355, résumé no. 152571n, Columbus, Ohio, US; & JP-A-78 52 631 (Y. OGAWA) 13-05-1978 * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2609998B1 (en) | 1994-04-15 |
| DE3802216A1 (en) | 1988-08-04 |
| GB8801560D0 (en) | 1988-02-24 |
| DE3802216C2 (en) | 1991-06-20 |
| JPS63218649A (en) | 1988-09-12 |
| GB2200633A (en) | 1988-08-10 |
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