WO2009071213A1 - Propriétés anti-glycation de l'acide asiatique et de l'acide madécassique - Google Patents

Propriétés anti-glycation de l'acide asiatique et de l'acide madécassique Download PDF

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Publication number
WO2009071213A1
WO2009071213A1 PCT/EP2008/009912 EP2008009912W WO2009071213A1 WO 2009071213 A1 WO2009071213 A1 WO 2009071213A1 EP 2008009912 W EP2008009912 W EP 2008009912W WO 2009071213 A1 WO2009071213 A1 WO 2009071213A1
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Prior art keywords
glycation
reducing
preventing
acid
inhibiting
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PCT/EP2008/009912
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English (en)
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Caroline Segond
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Bayer Consumer Care Ag
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Priority to EP08856329A priority Critical patent/EP2229165A1/fr
Publication of WO2009071213A1 publication Critical patent/WO2009071213A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/191—Carboxylic acids, e.g. valproic acid having two or more hydroxy groups, e.g. gluconic acid
    • 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)
    • A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
    • 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
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q7/00—Preparations for affecting hair growth

Definitions

  • the present invention relates to the use of the use of compounds from Centella Asiatica selected from the group consisting of Asiatic acid and Madecassic acid, and plant extracts containing both acids in cosmetics, pharmaceuticals and food supplements for preventing the glycation phenomenon and the glycation consequences in tissues.
  • Centella asiatica also known as Violette marronne (Reunion Island), as Gotu Kola or as Indian pennywort (India), or as Centella repanda (North America) and as Talapetraka (Madagascar), is a polymorphous herb and belongs to the family of Umbelliferae (Apiaceae), particularly to the Hydrocotyle subfamily that grows wild in pantropical moist and shady regions at an ideal altitude of 600 to 1200m. Centella asiatica includes three varieties called Typica, Abyssinica and Floridana. It is known and used for healing, sedative, analgesic, antidepressant, antiviral and antimicrobial properties.
  • the biological activity is enabled by active molecules from the triterpene series such as Asiaticoside (I), Madecassoside (under its 2 isomeric forms : madecassoside itself and terminoloside) (JX), Asiatic acid (IDf) and Madecassic Acid (IV). They contribute to the natural defense of the plants against environmental aggression thanks to the anti-bacterial properties of the genins (HI, IV), which are obtained by hydrolysis from the heterosidic reserve form (I, II).
  • active molecules from the triterpene series such as Asiaticoside (I), Madecassoside (under its 2 isomeric forms : madecassoside itself and terminoloside) (JX), Asiatic acid (IDf) and Madecassic Acid (IV). They contribute to the natural defense of the plants against environmental aggression thanks to the anti-bacterial properties of the genins (HI, IV), which are obtained by hydrolysis from the heterosidic reserve form (I, II).
  • Extracts containing these compounds are used in the pharmaceutical and cosmetic industry regarding skin care and skin diseases, respectively for treating wounds, scars and venous insufficiency and for dermis restoration and anti-inflammatory properties as disclosed in WO2004/062678.
  • Glycation is a slow, spontaneous, non-en2ymatic reaction which happens in organism. It corresponds to the covalent linking between a protein and an oxidation derivative from sugar, more specifically a glucose oxidation derivative. Glycation occurs in three steps with first the reaction between protein amino groups with glucose-carbonyl group to form an unstable Schiff s base, wbich then rearranges rapidly to more stable Amadori products. The Amadori structure undergoes a series of slow reactions involving rearrangement, oxidation, and dehydration to form stable, heterogeneous adducts known as glycation products - like pyrralin, pentosidine, crosline, Advanced Glycation End Products (AGEs) — which remain tightly bound to the protein. This reaction is irreversible and leads gradually to the loss of the functional activity of the glycated proteins, their stocking and the generation of oxidative secondary reactions.
  • AGEs Advanced Glycation End Products
  • glycation occurs in the dermis and more specifically towards collagen fibres.
  • Collagen glycation increases gradually with years leading to the gradual formation of glycation products. Consequently physico-chemical changes of collagen changes with a decrease of its solubility and more sensitive to degradation. This phenomenon leads to tissue stiffening and a loss of the skin tonicity.
  • the topical application of an anti-glycation agent has been proved to improve the water content and elasticity of aged skin (S.Vasan et al / Archives of Biochemistry and Biophysics VoI 419, p.89-96, 2003).
  • cytoskelett e.g. Vimentin
  • fibroblast contractility alterations of the cytoskelett (e.g. Vimentin) and negative impact on fibroblast contractility
  • Glycation phenomenon and consequences of AGEs are related to age but also with chronic diseases such as type ⁇ diabetes mellitus, Alzheimers' disease (damaged endothelium and collagen), cancer (acrylamide and other side products are released, peripheral neuropathy (the myelin is attacked) and other sensory losses such as deafness and blindness (microvascular damage in the retina).
  • the negative influence on fibroblast contractility caused by alterations of the the cytoskelett (vimentin) (T.Kueper et al. / Journal of Biological Chemistry VoI 282(32), p.23427-36, 2007), could also contribute to delayed healing and reduced reorganisation of collagen in aged and/or diabetic skin.
  • the present invention relates to the use of compounds from Centella Asiatica selected from the group consisting of Asiatic acid and Madecassic acid for preventing the glycation phenomenon and the glycation consequences in tissues.
  • Asiatic acid and Madecassic acid are well-known and commercially available compounds. Their glycolated derivatives asiaticoside and madecassoside can be isolated from e.g. Centella asiatica and the free acids can be prepared by hydrolysis as described in GB923414
  • Subject of the present invention is the use of Asiatic acid and/or Madecassic acid or plant extracts comprising one or both acids for the manufacture of a composition for preventing the glycation phenomenon and the glycation consequences in tissues.
  • the solvent of the extract is preferably a mixture of water and alcohol e.g. ethanol.
  • the ratio of the volume between water and alcohol can be from 50:50 up to 90:10, preferably 75:25.
  • Asiatic acid and Madecassic acid can be used in combination or as single isolated substances or in combination with one or more other compounds such as asiaticoside, madecassoside and/or terminoloside.
  • Preference is given to a combination or plant extract comprising at least Asiatic acid and/or Madecassic acid and optionally Asiaticoside, Madecassoside and/or Terminoloside.
  • Compounds, mixtures and extracts of the present invention can be administered in any form by any effective route, including, e.g., oral, parenteral, enteral, intravenous, intraperitoneal, topical, transdermal (e.g., using any standard patch), ophthalmic, nasally, local, non-oral, such as aerosol, inhalation, subcutaneous, intramuscular, buccal, sublingual, rectal, vaginal, intra-arterial, and intrathecal, etc. They can be administered alone, or in combination with any ingredient(s), active or inactive. Preference is given to a topical administration.
  • any effective route including, e.g., oral, parenteral, enteral, intravenous, intraperitoneal, topical, transdermal (e.g., using any standard patch), ophthalmic, nasally, local, non-oral, such as aerosol, inhalation, subcutaneous, intramuscular, buccal, sublingual, rectal, vaginal, intra-arterial, and intrathe
  • compositions used as food supplement can be converted in a known manner into the usual formulations such as cosmetic or pharmaceutical compositions or compositions used as food supplement.
  • These may be liquid or solid formulations e.g. without limitation normal and enteric coated tablets, capsules, pills, powders, granules, elixirs, tinctures, solution, suspensions, suppositories, syrups, solid and liquid aerosols, emulsions, pastes, creams, ointments, milks, gels, salves, serums, foams, shampoos, sticks or lotions.
  • a cosmetic composition in a form of an aqueous solution, a white or colored cream, ointment, milk, gel, salve, serum, foam, shampoo, stick, cream, paste, or lotion.
  • additives include any of the substances already mentioned, as well as any of those used conventionally, such as those described in Remington: The Science and Practice of Pharmacy (Gennaro and Gennaro, eds, 20th edition,
  • the dosage of the compounds, mixtures and extracts of the present invention can be selected with reference to the other and/or the type of disease and/or the disease status in order to provide the desired therapeutic activity. These amounts can be determined routinely for a particular patient, where various parameters are utilized to select the appropriate dosage (e.g., type of disease, age of patient, disease status, patient health, weight, etc.), or the amounts can be relatively standard.
  • the amount of the administered active ingredient can vary widely according to such considerations as the particular compound and dosage unit employed, the mode and time of administration, the period of treatment, the age, sex, and general condition of the patient treated, the nature and extent of the condition treated, the rate of drug metabolism and excretion, the potential drug combinations and drug-drug interactions, and the like.
  • composition comprising Asiatic acid and/or Madecassic acid in an amount of from 0.005% up to 10%, preferably 0.01 up to 5%, more preferably 0.1% up to 3% by weight of the total composition.
  • Asiatic acid and/or Madecassic acid or extracts containing one or both acids can also be combined with other anti-aging or wound healing promoting and scar reducing agents like anti-glycation active ingredients e.g. aminoguanidin, anti-wrinkles products, anti-oxidizing agents, activators or protectants of the ECM compound synthesis, anti-inflammatory agents, chelating agents, vitamins (e.g. Vitamin E, C, B3,...), UV filters or sunscreens, growth factors, (micro-)nutrients, amino acids, physiological (ceramides, cholesterol, free fatty acids) and moisturizing agents e.g. dexpanthenol, pantothenic aicd or derivatives thereof.
  • the pharmaceutical or cosmetic composition according to the invention is administered one or more, preferably up to three, more preferably up to two times per day. Preference is given to a topical administration.
  • Asiatic acid and/or Madecassic acid, or extracts, combinations or compositions comprising one or both acids can be used for preventing the glycation phenomenon and the glycation consequences in tissues.
  • Asiatic acid and/or Madecassic acid, or extracts, combinations or compositions comprising one or both acids can be used for preventing or inhibiting of the glycation of the proteins in the dermis, in particular the glycation of collagen, preventing or inhibiting of the cross-linking of collagens and/or of the extracellular matrix proteins in the dermis, preventing or inhibiting of accelerate aging, impaired wound healing, and appearance of scars.
  • Asiatic acid and/or Madecassic acid, or extracts, combinations or compositions comprising one or both acids can be used for preventing or inhibiting of the glycation of intracellular proteins, in particular cytoskeletal proteins like Vimentin, preventing or inhibiting of the cross-linking of Vimentin and/or other intracellular proteins, preventing or inhibiting impaired cellular contraction in skin ageing, wound healing, and scar tissue remodelling.
  • Asiatic acid and/or Madecassic acid, or extracts, combinations or compositions comprising one or both acids can be used for treating aging symptoms of skin, nails and/or hair in relation with glycation.
  • Asiatic acid and/or Madecassic acid, or extracts, combinations or compositions comprising one or both acids can be used for the prevention or treatment of capillaritis (pigmented purpura), acanthosis nigricans, Sclerosis, sclerodermiformis syndroms, xerosis, Dupuytren disease, Rubeosis, conjonctive alterations, Xanthochromia, Chronic Venous Insuffiency (Heavy legs), general disturbances of microcirculation..
  • glycation phenomenon is important in microvascular angiopathy and the associated cutaneous disorders such as acanthosis nigricans, rubeosis and purpural and pigmented capillaritis (Flagothier C. et al., Rev Med Med vide 2005, 60, 5-6, 553-559).
  • Xerosis and Dupuytren diseases can be quoted among the affections linked to diabetes, glycation and microangiopathy and the consequent reduced blood flow (Diris N et al., Ann Dermatol Venereol 130(11), 1009-1014, 2003; Rosenblomm AL et al, Endocrinol Metab Clin North Am 25(2), 473-483, 1966; Melling M et al, Arch. Pathol. Lab Med. 124 (9) 1275-1281, 2000; Melling M et al, Anat.Rec 255(4) 401-406, 1999).
  • Xanthochromia corresponds to a skin and nail coloration that can be caused by glycation.
  • Example 1 In vitro evaluation of the activity of Asiatic acid on glvcation (fibres reticulation " )
  • Glycation is induced by addition of glucosone and the glycation level is characterized by the visual evaluation of the collagen colour (Browning effect appears with induction of glycation) and by collagen migration in SDS-PAGE electrophoresis after controlled digestion by pepsine followed by silver nitrate dyeing. Test is performed in duplicate.
  • Aminoguanidine is used as a reference molecule as known to inhibit glycation reaction.
  • Asiatic acid is tested after solubilization in DMSO (Dimethyl sulfoxide) and dilution in PBS buffer (0.05M, pH 7.4). Tested concentrations are l ⁇ g/mL, lO ⁇ g/mL and 50 ⁇ g/mL.
  • Tendons (about 100 mg) are incubated during 15 days with glucosone (2.5 mM) in presence of the tested substance and aminoguanidine (10 mM) at 37°C. Unglycated control is obtained after incubation during 15 days without other treatment and glycation control with aminoguanidine treatment only.
  • Collagen is then solubilized in a solution at 3% acetic acid. After complete solubilization, pepsine is added (0.05 mg/ml) for treatment overnight at room temperature. Collagen precipitation is then obtained by adding NaCl 5M before being rinsed out to eliminate pepsine.
  • Collagen is solubilized again in acetic acid (3%) to enable protein quantification. 2 ⁇ g of proteins are denaturated by heating (90%) in presence of sodium lauryl sulfate and ⁇ -mercaptoethanol and are laid down on a polyacrylamide gel surface. Electrophoretic migration is performed during 3 hours before the final dying with silver nitrate.
  • Asiatic acid is able to prevent the collagen glycation induction by glucosone.
  • the activity is similar and even greater than that of aminoguanidine.
  • Asiatic acid can therefore be used in cosmetic or pharmaceutical preparations which aim at glycation phenomena and more widely the tissue status and appearance linked to the dermal structure preservation.
  • Example 2 In vitro evaluation of the activity of Genins on Advanced Glycation End products (AGEsVinduced apoptosis
  • Genins are therefore able to protect the cells against Advanced Glycation End products and to protect the skin against glycation consequences.
  • Cream 1
  • Ingredients 1.0% of Asiatic acid, or extract of Centella asiatica according to the invention), 1.5% of beheneth-10, 1.5% of beheneth-25, 5.0% of dycaprylyl carbonate, 5.0% of hexyl laurate, 5.0% of isohexadecane, 5.0% of cetearyl isononaoate, 1.0% of dimethicone, 2.0% of behenyl alcohol, 2.0% of hydrogenated vegetable glycerides, 0.5% of phenoxyethanol and parabens, 0.5% of tocopherol acetate, 3.0% of glycerol, 2.0% butylenes glycol, 0.1% of xanthan gum, 0.2% of carbomer and water (qs 100).
  • ESfCI w/w%: 1.0% of Asiatic acid, or extract of Centella asiatica according to the invention), 5.0% of cetearyl glucoside and cetearyl alcohol, 5.0% of caprylic/capric triglyceride, 5.0% of squalane, 3.0% of cetearyl isononaoate, 2.0% of dimethicone crosspolymer, 1.5% of stearyl alcohol, 5,0% of dycaprylyl carbonate, 0.1% parabens, 0.5% of phenoxyethanol and parabens, 2.0% of glycerol, 0.3% of carbomer, 2.0% of PEG 32, 0.2% of xanthan gum, 2.0% of aluminium starch octenyl succinate and water (qs 100).

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Abstract

La présente invention concerne l'utilisation de composés issus de Centella Asiatica choisis dans le groupe constitué par l'acide asiatique et l'acide madécassique, et d'extraits de plantes contenant les deux acides dans des produits cosmétiques, des produits pharmaceutiques et des compléments alimentaires afin de prévenir le phénomène de glycation ainsi que les conséquences de la glycation dans les tissus, plus particulièrement pour prévenir le vieillissement de la peau, pour augmenter la cicatrisation des plaies, pour traiter une insuffisance veineuse, etc.
PCT/EP2008/009912 2007-12-06 2008-11-22 Propriétés anti-glycation de l'acide asiatique et de l'acide madécassique WO2009071213A1 (fr)

Priority Applications (1)

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EP08856329A EP2229165A1 (fr) 2007-12-06 2008-11-22 Propriétés anti-glycation de l'acide asiatique et de l'acide madécassique

Applications Claiming Priority (2)

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EP07291467 2007-12-06
EP07291467.4 2007-12-06

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WO2009071213A1 true WO2009071213A1 (fr) 2009-06-11

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EP (1) EP2229165A1 (fr)
AR (1) AR069518A1 (fr)
CL (1) CL2008003505A1 (fr)
PE (1) PE20091235A1 (fr)
TW (1) TW200938215A (fr)
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Cited By (4)

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WO2014095289A3 (fr) * 2012-12-20 2014-12-31 Unilever Plc Méthode de traitement du vieillissement capillaire
US9233062B2 (en) 2011-05-10 2016-01-12 Mary Kay Inc. Cosmetic compositions
GB2543091A (en) * 2015-10-09 2017-04-12 Carlene Weller Kerri-Anne A topical herbal healing formulation
CN111920760A (zh) * 2020-07-28 2020-11-13 长沙医学院 一种羟基积雪草酸固体脂质纳米粒凝胶

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US10980851B2 (en) * 2018-06-08 2021-04-20 The Procter & Gamble Company Topical skincare compositions comprising Centella asiatica selected triterpenes

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US10322080B2 (en) 2011-05-10 2019-06-18 Mary Kay Inc. Cosmetic compositions
WO2014095289A3 (fr) * 2012-12-20 2014-12-31 Unilever Plc Méthode de traitement du vieillissement capillaire
GB2543091A (en) * 2015-10-09 2017-04-12 Carlene Weller Kerri-Anne A topical herbal healing formulation
WO2017060535A1 (fr) * 2015-10-09 2017-04-13 Weller Kerri-Anne Carlene Formulation topique de cicatrisation à base de plantes
CN111920760A (zh) * 2020-07-28 2020-11-13 长沙医学院 一种羟基积雪草酸固体脂质纳米粒凝胶
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