WO2020230095A1 - Composition pour la prévention et le traitement de signes du vieillissement cutané - Google Patents

Composition pour la prévention et le traitement de signes du vieillissement cutané Download PDF

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Publication number
WO2020230095A1
WO2020230095A1 PCT/IB2020/054602 IB2020054602W WO2020230095A1 WO 2020230095 A1 WO2020230095 A1 WO 2020230095A1 IB 2020054602 W IB2020054602 W IB 2020054602W WO 2020230095 A1 WO2020230095 A1 WO 2020230095A1
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WIPO (PCT)
Prior art keywords
composition
skin
extract
proline
withania somnifera
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PCT/IB2020/054602
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English (en)
Inventor
Giammaria Giuliani
Fabio Rinaldi
Barbara MARZANI
Daniela PINTO
Original Assignee
Giuliani S.P.A.
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Filing date
Publication date
Application filed by Giuliani S.P.A. filed Critical Giuliani S.P.A.
Priority to EP20742849.1A priority Critical patent/EP3968947A1/fr
Publication of WO2020230095A1 publication Critical patent/WO2020230095A1/fr

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    • 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
    • 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
    • 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]

Definitions

  • the present invention relates to a composition for the prevention and treatment of signs of skin aging.
  • the present invention relates to the nutraceutical and cosmetics sector and aesthetic dermatology.
  • the present invention relates to a composition for preventing or treating the signs of skin aging resulting from oxidative stress in cells.
  • the aging of the human body is a natural gradual degenerative type process mainly caused by a combination of factors of genetic and environmental origin. Some factors or events such as the development of diseases, taking medicinal products and some unnecessary behaviour can accelerate the decay of the organism.
  • Some tissues such as the epidermis, are more subject than others to the harmful action of environmental agents, mainly exposure to solar radiation and therefore they reveal the signs of aging of the organism more greatly.
  • the cells of the epidermis gradually lose their ability to proliferate, causing the skin to become thinner. This phenomenon is accompanied by a loss of elasticity and a thickening of the outer keratin layers whereas the slowing of cell proliferation causes an imbalance in the physiological water evaporation process and a reduction in collagen content.
  • UVB rays In relation to exposure to the sun’s rays, it has been found that exposure to UVB rays mainly causes damage to the more superficial layers of the skin. A typical example of this damage also associated with burning is presented in cases of sunburn. Vice versa, UVA rays have a greater capacity to penetrate into the skin’s layer and their exposure can cause early aging of the skin and the appearance of actinic or precancerous lesions.
  • UV rays are in fact able to generate reactive oxygen species (ROS) and thus alter cellular homeostasis.
  • ROS reactive oxygen species
  • ECM extracellular matrix
  • Oxidative stress is determined by an imbalance between the production of ROS and their neutralization by the antioxidant systems of the cells.
  • Non-neutralized ROSs promote different types of cell damage: lipoperoxidization which damages the cell membranes, the alteration of the structure and functionality of many enzymes, as well as promoting the oxidization of carbohydrates.
  • the skin In response to the attacks of the ROSs, the skin has a protective system constituted by endogenous antioxidants of the enzymatic and non-enzymatic type.
  • the cutaneous system of antioxidants becomes less efficient during aging and however is not able to stop continuous aggression from external agents, such as solar rays.
  • preparations containing substances with antioxidant activity such as, for example, vitamin C and vitamin E or epigallocatechin gallate is known for the purpose of preventing or reducing skin damage induced by UV rays.
  • One of the aims of the invention therefore consists in providing a combination of active substances that are effective in the reduction of the signs of skin aging such as wrinkles or loss of elasticity of the skin.
  • Another aim of the invention consists in providing a composition for the prevention and treatment of the signs of skin aging that can be applied topically or administered orally whose use is almost free of side effects.
  • the Applicant has found that by combining one or more active components available from a Withania somnifera extract with L-proline, an antiaging effect and a reduction in the typical signs of skin aging are obtained.
  • the inventors have also observed that the combination of biologically active components present or extracted from Withania somnifera with L-proline prevents or reduces oxidative stress in cells.
  • the present invention provides, according to a first aspect thereof, the non-therapeutic use of a composition comprising a Withania somnifera extract or withanolides in combination with L-proline or proline for reducing or delaying an aesthetic damage of the skin or signs of skin aging.
  • composition of the invention is specifically indicated in the prevention or treatment of signs of skin aging, in particular the inherent signs caused by exposure to ultraviolet radiation, in particular solar radiations.
  • composition of the invention can be specifically used in preventing or treating skin damage caused by prolonged exposure to solar radiations that determine early skin aging.
  • Figure 1 illustrates bar graphs representative of the effects on gene expression, named in ordinate as Fold Change, of some significant markers for aging and skin inflammation, in particular MMP2 and S100A7A, of L-proline (15mg/ml) of Withania somnifera (15 mg/ml) individually and of the combination thereof (15 mg/ml) on a 3D skin model, according to the test of Example 6.
  • Figure 2 illustrates a flow-chart of an embodiment of the production process of a powdered extract from a Withania somnifera plant as described in Example 7.
  • the present invention originates from the finding that by combining a plant extract of Withania somnifera with L-proline or proline, a synergistic action on the main skin markers of a skin model is obtained. This action makes it possible both to prevent/treat aesthetic skin damage and to prevent/treat damage to the epidermis caused by exposure to ultraviolet radiation.
  • composition of the invention is therefore indicated in a non-therapeutic context in preventing and/or treating early skin aging, aging due to exposure to solar rays, in particular due to oxidative stress.
  • composition is provided as defined in the appended claim 1 .
  • composition of the invention can be applied in delaying skin aging and/or signs of skin aging in particular following exposure to ultraviolet radiation.
  • the invention relates to a composition
  • a composition comprising withanolides or an extract of Withania somnifera in combination with L-proline for use in reducing or delaying skin damage caused by exposure to ultraviolet radiation in particular the sun’s rays.
  • the composition is a pharmaceutical composition for use in therapy for preventing or treating skin diseases caused, originating or triggered by exposure to ultraviolet radiation, in particular dermatological affections selected from actinic lesions, precancerous skin lesions or a non-melanoma form of skin cancer.
  • composition of the invention may be used in the prevention or non-therapeutic treatment of aging due to exposure to solar rays.
  • composition of the invention may be used in preventing or treating signs of skin aging due to repeated exposure over time to ultraviolet radiations such as, for example, skin folds, wrinkles, skin thickening, skin sagging, dehydration and creasing of the skin on the body and in particular the face.
  • composition of the invention may be used, both for uses in the medical field and non-therapeutic ones, in the treatment of skin damaged by exposure to UBA, UVB or UVC rays and in general in photoaging.
  • UV-A radiation means radiation with a wavelength of 315 to 400 nm
  • UV-B radiation means radiation with a wavelength of 280 to 314 nm
  • UV-C radiation means radiation with a wavelength of 100 to 279 nm.
  • the biologically active components present in the composition both for medical and non-therapeutic use are the same. These components and other aspects of the composition of the invention are described in detail below.
  • composition of the invention a Withania somnifera extract or withanolides contained in this plant can be used.
  • Withania somnifera is a plant that belongs to the Nightshade family, Withania genus, with the common name of Ashwagandha.
  • the plant and its extracts contain biologically active substances, mainly present in the roots among which the most representative or most active substances are non-steroidal lactones known as withanolides.
  • composition of the invention it is preferable to use a Withania somnifera extract or alternatively withanolides which from a chemical point of view are typically steroidal lactones with the skeleton of ergostane present in the Withania somnifera plant.
  • a Withania somnifera extract can contain from 0.5% to 15%, from 1 to 10% from 2 to 7% by weight of withanolides (drug) expressed as a drug/extract ratio.
  • the withanolides described herein are of plant origin, however they may also be of synthetic origin, i.e. obtained by means of a chemical synthesis process.
  • Suitable withanolides comprise withaferin A, Withanolide I, II, III, A, D, E, F, G, H, I, J, K, L in particular withanolide D, isopelletierine (alkaloid), Anefrin (alckaloid), Salpichrolide A, Nicandrenon-1 , Ixocarpalactone A and mixtures thereof.
  • withaferin A, withanolide D and the mixture thereof are suitable, in particular obtained from a Withania somnifera extract according to an embodiment described herein.
  • a suitable vegetable/plant extract of Withania somnifera can be derived or extracted from the roots, leaves, fruits, berries or flowers of Withania somnifera or from two or more of these parts of the plant, preferably from the roots.
  • the vegetable plant extract described herein originates or is obtained from the roots of Withania somnifera and is advantageously in the form of powder, typically yellow/light brown coloured.
  • the Withania sominifera extract is in powdered or ground form, with powders/granules preferably with particle size passing through a 40 mesh sieve > 95% (p/p) or passing through an 80 mesh sieve > 85% (w/w).
  • Examples of particles of Withamnia somnifera extract are reported in the following Examples 7 and 8.
  • the plant extract of the invention can be obtained by extraction from a part of the plant, in particular the roots using as the extraction means a physiologically acceptable or edible solvent.
  • the term“edible” means a physiologically acceptable solvent that can be used or administered to a human being.
  • a suitable solvent for obtaining the plant extract is a physiologically acceptable and/or edible liquid in which the biologically active components are soluble and wherein they do not undergo any significant alteration such as to compromise the biological activity.
  • a suitable extract is obtained through aqueous extraction or organic extraction using ethanol or a hydro-alcoholic mixture.
  • the solvent is hydrophilic and is selected from water, ethanol, ethyl acetate or mixtures thereof and is preferably water.
  • the extraction of one or more biologically active components takes place by grinding a plant matrix or portion in a suitable solvent, e.g. a hydroalcoholic mixture.
  • a suitable solvent e.g. a hydroalcoholic mixture.
  • a suitable extraction envisages that the Withania somnifera roots are ground to provide a powder from which the extraction is performed using a suitable solvent such as water or a water-ethanol mixture, or ethanol, for an amount of time suitable to enrich the solvent with one or more biologically active components, e.g. 10 minutes.
  • the extract can be sonified. And centrifuged for example at 3000 rpm for 4-6 minutes.
  • the extract obtained is collected and can be diluted with water, alcohol, typically ethanol or a water-ethanol mixture, for example to obtain a final volume of 10 ml if starting with 1 gram of initial powder.
  • the extraction of the solvent of the biologically active components present in the plant tissues of the plant can thus take place by diffusion and osmosis.
  • the extract obtained from Withania somnifera may be fluid, soft or dry.
  • 1 ml of extract contains biologically active components soluble in 1 g of herbal drug
  • the solvent is partially evaporated in particular until the extract wets a filter paper, in the dry extract the solvent is almost completely evaporated to obtain a powder.
  • the extraction takes place using a weight ratio between solvent and plant matrix comprised between 1 : 10 and 10: 1 .
  • plant extract denotes an extract obtained by extraction from Withania somnifera or withanolides contained therein.
  • a further component of the composition of the invention is the proline of a non-polar amino acid also known as 2(S)-pyrrolidine-carboxylic acid.
  • a non-polar amino acid also known as 2(S)-pyrrolidine-carboxylic acid.
  • L-proline is used.
  • proline or L- proline it is possible to use the hydroxyproline identified in the lUPAC as (2S,4R)-4- hydroxypyrrolidine-2-carboxylate.
  • the Applicants have unexpectedly observed that the combination of a Withania somnifera extract or withanolides contained therein with L-proline has anti-aging activity which at epidermal level manifests itself with an improvement to the appearance of the treated skin.
  • This cosmetic or aesthetic effect manifests itself both in the case of topical skin treatment with the combination of Withania somnifera/withanolides and L-proline and in the case of oral administration of the combination or a composition that contains it.
  • composition of the invention can therefore be intended for external use and for oral administration.
  • composition of the invention can be authorized for sale as a cosmetic product for local application, or as a drug, a dietary or nutritional supplement intended for oral administration.
  • the composition of the invention comprises a carrier, diluent or physiologically and/or cosmetically acceptable excipient.
  • the physiologically or cosmetically acceptable carrier of the composition of the invention is an excipient, carrier or diluent suitable for topical application and/or oral administration.
  • the term“carrier” refers to an excipient, carrier, diluent or coadjuvant that may be present in the composition of the invention. Any carrier and/or excipient suitable for the desired form of preparation for administration is contemplated in the uses of the plant extract or active ingredients present therein described here.
  • the composition of the invention contains one or more components of plant origin that are biologically active and substantially free from side effects, when administered orally or locally.
  • the carrier, diluent or physiologically or pharmaceutically acceptable excipient may be selected on the basis of the administration route for which the resulting pharmaceutical composition is intended.
  • composition may be in the form for oral administration.
  • compositions for oral administration may be in solid or liquid form.
  • Typical compositions in solid form comprise tablets, capsules, powders, granules and pills.
  • Typical compositions in liquid form comprise solutions, emulsions, suspensions and syrups. All the compositions also comprise controlled release forms thereof.
  • a preferred embodiment of the composition is the one in tablet form.
  • the tablets generally comprise a suitable carrier or excipient in which the plant extract is dispersed, typically in dry form.
  • suitable excipients contained in the formulation are cellulose and derivatives thereof such as hydroxymethyl cellulose, hydroxypropyl methyl cellulose, methyl cellulose, hydroxypropyl cellulose, hydroxyethyl cellulose, carboxyethyl cellulose, ethyl hydroxyethyl cellulose, carboxymethyl cellulose, cellulose acetate butyrate, cellulose acetate phthalate, and mixtures thereof.
  • excipients comprise polymers that are part of the family of lactam family such as pyrrolidone and derivatives thereof, for example polyvinylpyrrolidone, polyvinylpolypyrrolidone and mixtures thereof, inorganic salts such as calcium or dicalcium phosphate, lubricants such as for example magnesium stearate, triacylglycerides and mixtures thereof.
  • the tablet can further comprise one or more of the following excipients: bulking agents such as calcium phosphates, stabilizers such as crosslinked sodium carboxymethylcellulose, coating agents such as polyvinyl alcohol, polyethylene glycol, talc, anticaking agents such as magnesium salts of fatty acids; silicon dioxide.
  • bulking agents such as calcium phosphates, stabilizers such as crosslinked sodium carboxymethylcellulose
  • coating agents such as polyvinyl alcohol, polyethylene glycol, talc
  • anticaking agents such as magnesium salts of fatty acids
  • silicon dioxide silicon dioxide.
  • the two biologically active synergistic components contained in the composition of the invention may be present in variable quantities, e.g. comprised from 0.0001 % by weight to 50% by weight, from 0.1 % by weight to 20% by weight, typically from 0.5 to 5% by weight.
  • composition of the invention further comprises one or more active ingredients such as vitamins, minerals, micronutrients and other active ingredients.
  • biologically active suitable substances that can be included in the formulation of the composition are selected from the group comprising glycine, Moringa seeds or extract, N-acetylglucosamine, niacin, fermented Goji hyaluronic acid and mixtures thereof.
  • N-acetylglucosamine increases the synergistic effect of antiaging and/or reduction of oxidative stress in the cells of the two basic components of the composition of the invention.
  • the composition for oral administration is a functional food, a nutraceutical composition, a dietary product, a supplement or nutritional product or a medical device.
  • Functional food means any modified food or food ingredient that can provide a benefit or protection against a drawback or physiological affection, in addition to the traditional nutrients that it contains.
  • Nutraceutical product means an isolated or purified product from edible substances. A nutraceutical is such when it is demonstrated that it has a physiological benefit or that it provides protection against a drawback or physiological disorder.
  • Dietary or food supplement means a product that contains a vitamin, mineral, plant extract, amino acid, metabolyte, extract, concentrate or mixture of these ingredients.
  • the amount administered and the frequency of administration of the composition will depend on the nature and gravity of the affection to be treated.
  • the administration route of the composition of the invention is the topical one.
  • the composition is for topical use and is applied to the skin.
  • composition for topical application may be in solid, semi-solid or fluid form.
  • Suitable formulations in solid form include creams, balms, pastes, ointments.
  • the formulation for local administration is in fluid form, e.g. in the form of lotions, jellies, shampoos, suspensions or semi-fluid e.g. in the form of gels and emulsions.
  • compositions of the invention may comprise excipients commonly used in the formulation of cosmetic or pharmaceutical preparations, for local use, such as preservatives, anti-bacterial agents, stabilizers, emulsifiers, buffers, wetting agents, dyes and other excipients commonly used in cosmetic/pharmaceutical preparation techniques.
  • the formulation for local application is in emulsion form containing the extract carried in a suitable excipient.
  • the composition for topical application comprises an excipient of the hydroxymethyl cellulose type and/or gelling agents suitable for the formulation and for the substances.
  • a cosmetic treatment method comprises the application onto the skin of an effective quantity of a composition for topical use as previously described.
  • composition in tablet form containing the following active substances
  • Microcrystalline cellulose 20-200 mg mono- and diglycerides of fatty acids . 5-14 mg
  • Soy oil ( Glycine max L.) . 100-400 mg
  • Soy lecithin Glycine max L.
  • Soy lecithin 5-10 mg mono- and diglycerides of fatty acids . 5-30 mg
  • composition of the shell is composition of the shell:
  • the biological model used is represented by the Phenion ® Full-Thikness (FT) Skin Model supplied by Henkel. It is a full-thickness model obtained from the co-culture of keratinocytes and fibroblasts coming from a single donor, which simulates the histological and physiological properties of human skin.
  • the model is presented in the form of a 1 .3 cm circular disc kept in culture for at least 10 days and that allows repeated treatments.
  • the Phenion® skin model comprising different types of cells, derived from human skin.
  • the fibroblasts are cultivated within a collagen framework and form the connective tissue that will act as a base for the overlying layers of epithelial cells to mimic the in vivo conditions.
  • the de novo synthesis of collagen and of the elastic matrix can be observed, consisting of proteins such as elastin and fibrillin-1 .
  • the differentiation of the cells within the stratified multi-epithelium can be viewed through the detection of specific markers such as cytokeratin 10, filaggrin, involucrin and transglutaminase.
  • FT inserts Panion ® Full- Thickness (FT) must be treated in sterile conditions. Immediately after arrival the FT inserts were removed from the semi-solid transport medium according to the guidelines reported below.
  • the inserts normally reach Friday (6th day of differentiation). They are seeded as reported above and used for treatment on Monday (9th day of differentiation).
  • the protocol envisages the stimulation of the FT inserts with Triton-X (45mg/ml_) in order to induce system inflammation.
  • Validated protocols recommend the induction of inflammation with Triton-X in the amount of 0.12mg/cm 2 .
  • the gene expression of the gene markers of skin-aging was evaluated through quantitative reverse transcription- polymerase chain reaction- qRT-PCR.
  • RNA concentrations in pg/mL of total RNA were calculated extracted at the wavelength of 260 nm.
  • the integrity of the RNA (2 pg/mL) was calculated using 1 % agarose gel electrophoresis.
  • RNA was converted into cDNA (complementary DNA), using the commercial“RT 2 First Strand Kit” (Qiagen, Italy).
  • thermocycler Stratagene Mx3000P Real Time PCR System, Agilent Technologies Italia S.p.A., Milano, Italy
  • qRT-PCR represents an amplification and quantification method in real time for the amplified products monitoring the fluorescence emitted during the reaction.
  • RT-PCR amplification a custom kit containing anti-aging gene markers (Qiagen, Italia) was used and the amplification performed through RT2 SYBR® Green qPCR Mastermix (Qiagen, Italy).
  • the amplification was performed on a final volume of 25 uL under the following conditions:
  • AACt ACt target-housekeeping (contl ol)-ACt target-housekeeping (treated cells) Assuming an amplification efficiency of 100% the 2-AACt was calculated.
  • the appended Figure 1 summarizes the following gene expression data of genetic markers related to aging phenomena, in particular skin aging.
  • the combination of Withania somnifera and L-proline can act synergistically on the stimulation of POT1 , SIRT1 , LMNA, CASP1 , COL1A1 , COL3A1 , KRT13, the increase in which is positively connected to anti-aging activity. At the same time it is able to synergistically inhibit the gene expression of MMP2 and S100A7A.
  • the aging process is complex and envisages a series of mechanisms that range from genetic programming to neuroendocrine and immune decline, inflammation and oxidative stress for excessive production of free radicals and incapacity of their detoxification by the other.
  • Numerous experimental investigations highlight how genes such as SIRT1 or LMNA are also able to perform antioxidant activity with multiple mechanisms.
  • SIRT1 stimulates mitochondrial biogenesis, reduces the production of superoxide from the respiratory chain and improves the expression of manganese-dependent superoxide dismutase (SOD2) in the mitochondria, with the consequent increase in mitochondrial superoxide dismutase. Furthermore, SIRT1 accelerates the detoxification of ROS up-regulating the antioxidant cell enzymes, including SOD1 , catalase, glutathione peroxidase 1 and thioredoxin-1 , Li H. (2014) Sirtuin 1 (SIRT1 ) and Oxidative Stress. In: Laher I. (eds) Systems Biology of Free Radicals and Antioxidants. Springer, Berlin, Heidelberg.
  • Fig. 1 highlights the effects on gene expression (fold-change) of the main aging markers and skin inflammation of L-Proline (15mg/mL), of Withania somnifera (15mg/mL) and of the combination thereof (L-Proline+Withania somnifera, 30mg/mL) on a 3D skin model.
  • the extract of Withania somnifera (Ashwagandha) root was produced according to current Good Manufacturing Practices (GMP), as indicated in the appended Figure 2.
  • GMP Good Manufacturing Practices
  • the roots of the ashwagandha plant grown organically using GACP Good Agricultural and Collection Practices
  • GACP Good Agricultural and Collection Practices
  • the selected roots are washed with water (reverse osmosis and demineralized) to remove sand, dust and undesired material in a washer designed specifically and then dried in hot air.
  • the dried roots are then ground to a fine powder in a pulverizer. Subsequently the fine pulverized powder is mixed with an equal amount of water and agitated for 2 hours. The liquid mixture thus obtained is transferred into a heating tank with more added water and continuous heating for 20 minutes under temperature and pressure control.
  • the slurry is cooled and then passed through a fine filter to remove undesired material such as waste particles and fibre.
  • the decoction obtained is placed in a vacuum dryer and dried at low temperatures until a humidity content of 2-3% is obtained.
  • the final product obtained is powdered and is further subjected to micro-pulverization, with consequent free flow fine powder. This powder is then inserted into a vibrating sieve, to obtain the final powder of the desired particle size.
  • the powder is packaged in double polyethylene food grade plastic and then inserted into watertight HDPE drums. The entire manufacturing process is performed in a clean room, following good manufacturing practices.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Gerontology & Geriatric Medicine (AREA)
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Abstract

La présente invention concerne une composition synergique comprenant des withanolides ou un extrait de Withania somnifera en association avec de la L-proline ou de la proline et un support physiologiquement acceptable. La composition est dotée d'une activité antioxydante cellulaire et peut être appliquée pour retarder le vieillissement cutané et pour prévenir ou réduire les dommages esthétiques causés à la peau ou les signes du vieillissement cutané, en particulier ceux provoqués par une exposition aux rayons solaires.
PCT/IB2020/054602 2019-05-16 2020-05-15 Composition pour la prévention et le traitement de signes du vieillissement cutané WO2020230095A1 (fr)

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EP20742849.1A EP3968947A1 (fr) 2019-05-16 2020-05-15 Composition pour la prévention et le traitement de signes du vieillissement cutané

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IT201900006899 2019-05-16

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050059727A1 (en) * 2003-09-11 2005-03-17 Board Of Trustees Of Michigan State University Withanamide and withanolide compositions and method of use thereof
JP2010083849A (ja) * 2008-10-02 2010-04-15 Tokiwa Shokubutsu Kagaku Kenkyusho:Kk 皮膚外用剤
WO2019026993A1 (fr) * 2017-08-02 2019-02-07 国立大学法人京都大学 Agent d'extension de durée de vie, agent anti-âge, produit cosmétique, et composition d'aliment/boisson

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050059727A1 (en) * 2003-09-11 2005-03-17 Board Of Trustees Of Michigan State University Withanamide and withanolide compositions and method of use thereof
JP2010083849A (ja) * 2008-10-02 2010-04-15 Tokiwa Shokubutsu Kagaku Kenkyusho:Kk 皮膚外用剤
WO2019026993A1 (fr) * 2017-08-02 2019-02-07 国立大学法人京都大学 Agent d'extension de durée de vie, agent anti-âge, produit cosmétique, et composition d'aliment/boisson

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BHARITKAR YOGESH P ET AL: "Chemistry of withaferin-A: chemo, regio, and stereoselective synthesis of novel spiro-pyrrolizidino-oxindole adducts of withaferin-A via one-pot three-component [3+2] azomethine ylide cycloaddition and their cytotoxicity evaluation", MOLECULAR DIVERSITY, ESCOM SCIENCE PUBLISHERS, LEIDEN, NL, vol. 19, no. 2, 8 March 2015 (2015-03-08), pages 251 - 261, XP035481573, ISSN: 1381-1991, [retrieved on 20150308], DOI: 10.1007/S11030-015-9574-6 *
SONAL SHAH ET AL: "Phytochemical and physiological changes in Ashwagandha (Withania somnifera Dunal) under soil moisture stress", BRAZILIAN JOURNAL OF PLANT PHYSIOLOGY, vol. 22, no. 4, 1 January 2010 (2010-01-01), pages 255 - 261, XP055633377, DOI: 10.1590/S1677-04202010000400005 *

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