WO2009080857A1 - Procédé d'obtention de mélanines et applications correspondantes - Google Patents

Procédé d'obtention de mélanines et applications correspondantes Download PDF

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Publication number
WO2009080857A1
WO2009080857A1 PCT/ES2008/070219 ES2008070219W WO2009080857A1 WO 2009080857 A1 WO2009080857 A1 WO 2009080857A1 ES 2008070219 W ES2008070219 W ES 2008070219W WO 2009080857 A1 WO2009080857 A1 WO 2009080857A1
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WO
WIPO (PCT)
Prior art keywords
pheomelanins
melanins
obtaining
minutes
eumelanin
Prior art date
Application number
PCT/ES2008/070219
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English (en)
Spanish (es)
Inventor
Manuel Jaren Galan
Juan Garrido Fernandez
Juan Jose Negro Balmaseda
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Consejo Superior De Investigaciones Cientificas
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Publication of WO2009080857A1 publication Critical patent/WO2009080857A1/fr

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Classifications

    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
    • A61K35/36—Skin; Hair; Nails; Sebaceous glands; Cerumen; Epidermis; Epithelial cells; Keratinocytes; Langerhans cells; Ectodermal cells
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
    • G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
    • G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
    • G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
    • G01N21/33—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using ultraviolet light

Definitions

  • the present invention is included within the chemical sector. Specifically, it describes the obtaining and subsequent quantification of purified melanins by means of a low cost technique.
  • Melanin is a general term that describes a family of quinol-phenolic pigments of diverse origin and chemical nature. Depending on their biological origin, the melanins are divided into three groups: microbial, animal and vegetable. There are also synthetic melanins. Animal melanins are the most common pigments in the vertebrate tegument (McGraw 2006), including the skin of humans (Jablonski 2006). From the chemical point of view, there are two basic types of melanins: pheomelanins and eumelanins, which give rise to the huge palette of melanin colors observed according to their concentration, relative proportions and contrast with depigmented areas.
  • Pheomelanins contain sulfur and are perceived as reddish or blond colorations, both in the hair or skin of mammals and in the feathers of birds. Eumelanins are black or brown, and that is the color they confer to the integumentary structures.
  • the Melanins are synthesized by the body itself from amino acid precursors. They also differ in that while melanins can appear within the same pen as bands or points alternated with depigmented areas or with different degrees of mechanization, carotenoids occupy continuous regions of color. This feature allows infinite variants, and thus, for example, diurnal birds of prey (Order Falcon forms, with about 300 species), have distinctive and specifically melanin plumages and even numerous species among them have great individual variation. Among the feral pigeons (Columba livia) more basic types of coloration have been described than in any species of wild bird, and that phenotypic multiplicity again responds to multiple combinations of melanin tones.
  • melanins As for the role of melanins in the tegument, it is essentially photoprotective, since it avoids the damage caused by the sun's ultraviolet (UV) radiation. They have, however, other potential functions: due to their structure they can protect cells and tissues from oxidative stress by trapping free radicals (McGraw 2006) and, in the case of bird feathers, it has been suggested that melanized feathers are more resistant to the deterioration by abrasion or mechanical breakage (Burtt 1986), and perhaps also to the attack of bacteria (Burtt and Ichida 1999) although this last aspect has been questioned recently (Grande and Cois 2004).
  • the second group of methods consists in extracting all other materials, with the exception of melanin, by acid hydrolysis and washing with a suitable solvent until melanin is obtained.
  • enzymatic extraction methods are based on the use of proteases that degrade keratins that envelop melanins in the hair or feathers (Liu 2003).
  • the procedure presented in this invention describes, for the first time, a method for obtaining the pheromellic fraction on the one hand and of the eumelanic fraction on the other, starting from an alkaline digestion from bird feather or mammalian colored hair.
  • the possibility of solubilizing the insoluble concentrate of eumelanin in the form of pseudofeomelanin in alkaline medium allows spectrophotometrically quantifying the relative concentration of pheomelanin and eumelanin without resorting to HPLC.
  • this method allows to obtain dry concentrates of the three fractions, pheomelanins, eumelanins and pseudosfeomelanins, which can be used as a natural raw material for use in cosmetics or dermatology
  • the present invention describes, for the first time, a procedure for obtaining, from a raw material of zero utility such as the bird feather or certain colored mammalian hairs, of purified extracts of pheomelanin , eumelanin and pseudofeomelanin.
  • Said procedure is simple and inexpensive, and allows the use of the extracts obtained both for photoprotective creams, as for makeup for cosmetic purposes or dermatological purposes in diseases that occur with depigmentation of the skin.
  • the present invention presents a simple and reliable method of quantifying melanins. Therefore, one aspect of the present invention constitutes a method of separation, quantification and obtaining of concentrates.
  • Another aspect of the invention constitutes the use of solid concentrates of pheomelanin, eumelanin and pseudofeomelanin obtained by the process of the invention, as raw material for industrial purposes for the preparation of cosmetic compositions.
  • the cosmetic compositions thus obtained may comprise other products, for example: skin makeup, eyelashes, eyebrows, lips or nails, hair or hair dyes, tattoo dyes, or any other cosmetic product.
  • the present invention faces the problem of offering a simplified and reproducible procedure for the determination of melanins, and more specifically for the determination of the basic types of melanins, eumelanins and pheomelanins, and a method of extracting and obtaining both types of melanins in solid state.
  • the present method for determining eumelanins and pheomelanins is based on an initial alkaline treatment to separate pheomelanins, and a time-controlled alkaline oxidation of insoluble eumelanins to transform them, stoichiometrically, into soluble pseudofeomelanins in alkaline medium. Subsequently, the relative concentration of pheomelanins and eumelanins is measured, spectrophotometrically, by analyzing the former directly and the latter from their oxidatively obtained soluble product, without resorting to HPLC. It is important to highlight that there is currently no method in which the feomellanic and eumelanic fractions are obtained separately starting from an alkaline digestion from a bird's feather or colored mammalian hair.
  • the procedure for the initial separation of the pheomelanins begins with an alkaline digestion of the raw material used by the addition of 20% NaOH dissolved in water. Digestion is carried out in a bath with controlled temperature sonication, preferably at 6O 0 C, for 40 minutes with periodic agitation of the sample. Once the alkaline digestion is finished, the soluble pheromellic fraction is separated from the precipitated eumelanic fraction, preferably by centrifugation.
  • the sample is centrifuged for 15 minutes at 17500 g and 4 0 C, removing the supernatant consisting of the fraction of solubilized pheomelanins and the material solubilized after digestion, formed essentially by free amino acids from the keratin of the pen.
  • the precipitate is reserved for the subsequent study of the eumelanic fraction.
  • the determination of the colored solution, which constitutes the pheromellic fraction is performed in a spectrophotometer. More specifically, the determination is made by means of the absorbance measurement at 450nm, subtracting the one obtained at 600nm against a blank of 20% NaOH aqueous solution. The result obtained is divided by the original sample weight to express the concentration of pheomelanins as UA / g of raw material.
  • a washing is carried out to eliminate possible remains of pheomelanins. Specifically, 1 ml of 20% NaOH in water is added to the precipitated eumelanic fraction, stirred, until a suspension is obtained, and centrifuged at 1750 Og for 15 minutes. The supernatant is neglected and the washing process is repeated a second time.
  • the resulting precipitate which is dried in an oven at 6O 0 C, constitutes the eumelanic fraction, insoluble under alkaline conditions, free of pheomelanins.
  • the oxidation reaction of the eumelanins is stopped by the addition of an antioxidant, specifically 0.050 ml_ of 40% HNaS03 in water, and stirring. After the oxidation reaction, centrifugation and spectrophotometric measurement of the solution of eumelanins transformed by oxidation in pseudofeomelanins are carried out under identical conditions to those described above for the pheromellic fraction, the results also being expressed as UA / g pen.
  • An additional feature of the present invention is the obtaining of dry concentrates of pheomelanin and pseudofeomelanin from a process of neutralization of the solutions used for quantifications.
  • the solutions of pheomelanin and pseudofeomelanins are neutralized, separately, with two-stage hydrochloric acid (HCI) using first 20% HCI until reaching a pH close to 8-9 units and subsequently, with 0.1 N HCI, The solution is neutralized until reaching a pH between 6-7 units.
  • the neutralized solution is allowed to cool and centrifuged at 1750Og for 20 minutes.
  • the supernatant obtained is neglected and the precipitate, once washed by resuspension with deionized water and subsequent centrifugation under identical conditions, is finally dried in an oven at 6O 0 C.
  • the precipitate obtained is constituted by the pheromellanic or pseudofeomellanic fractions respectively.
  • the precipitated solids are intensely colored and interpose easily with diluents by mechanical dispersion. They are not soluble in hydrophilic or lipophilic media, they are simply dispersible in solids or semi-solids of high viscosity, giving different colors depending on their concentration and the original coloration of the excipient.
  • the proposed determination methodology represents a remarkable advance in the field of melanins. With simple and inexpensive treatments, the content of pheomelanins can be directly quantified and indirectly that of eumelanins by correlation with the direct measurement of pseudofeomelanins.
  • Figure 1. It is shown how the process of solubilization of pheomelanins takes place as a function of time.
  • Figure 2. Verification of the linearity between the content of pheomelanins in the samples and the absorbance measured in three different bird species.
  • Figure 3. Detail of electron microscopy of the solid obtained after the separation of the pheromellic fraction and washing with water from the precipitate. Set of melanosomes containing eumelanin.
  • Figure 4. Evolution of the insoluble matter content and color of an eumelanic nature in samples treated under conditions of alkaline oxidation in the presence and absence of antioxidant.
  • Figure 5. FT-IR spectrum of pheomelanin, eumelanin and its alkaline oxidation product, pseudofeomelanin.
  • Figure 6. Verification of the linearity between the content of eumelanins in the samples and the absorbance measured in three different bird species.
  • Example 1 Methodologies of extraction, quantification and precipitation of pheomelanins.
  • the procedure set up is based on the known solubility of the pheomelanins in alkaline medium. Rooster pen of black coloration is used in the base and dark golden coloration in the tips. Cut into small pieces of approximately 1 g of rachis-free feathers and discard and mix to homogenize. Twenty samples of approximately 5 mg are taken and placed in Eppendorf tubes, 1.5 ml_ capacity and hermetically sealed, and 1 ml_ of 20% NaOH are added simultaneously. The tube set is Enter in a thermostated sonication bath at 6O 0 C. Two tubes are removed every 5 minutes, to minimize re-extraction after the established time, they are immersed in an ice bath and centrifuged at 4 0 C and 17.50Og for 15 minutes .
  • the amount of color extracted is a function of the weight used, following the Lambert-Beer law, in a wide weight range as long as the rest of the parameters set for the extraction remain identical.
  • Using feathers of three species with ugly and eumelanic content, in Figure 2 it can be seen that the linearity between featherweight and absorbance obtained has a correlation coefficient (r) in all three cases greater than 0.98.
  • the alkaline solution containing the solubilized pheomelanins is brought to neutrality with 20% HCI until the solution reaches a pH alkaline close to neutrality and it is finished accessing to the point of neutrality using HCI 0.1 N to be able to adjust more accurately that the final pH does not fall below 6.
  • the pheomelanins become insoluble forming a fine suspension that separates by centrifugation at 1750Og for 20 minutes and temperature of 4 0 C.
  • the suspension is formed by a fine powder with little tendency to precipitate, so that sometimes the precipitation is not complete and the supernatant retains some color.
  • Example 2 Development of methodologies for extraction and quantification of eumelanins.
  • the solubilization of the solid eumelanic residue, free of pheomelanins, is carried out by an oxidative treatment in alkaline medium.
  • the resuspension of the eumelanic precipitate in 1 ml of 20% NaOH solution is carried out first by stirring and subsequent sonication in an ultrasonic bath.
  • the oxidative treatment is carried out by adding 0.02 ml_ of 30% H2O2.
  • the reaction is carried out in an ultrasonic bath at 6O 0 C and allowed to run for 10 minutes.
  • the residue subsequently washed is dried in an oven and the weight of each of the samples is determined to know the content of the eumelanic concentrate from which it is started before starting the oxidative treatment.
  • measures of eumelanin content are also expressed in absorbance units per gram of initial pen.
  • the degradation reaction has been paralyzed, and the color that is measured is stable, at least within the 20 minutes that the reaction has been allowed to pass.
  • the antioxidant stabilization procedure is effective and allows for a reasonable timeframe for the spectrophotometric measurement, knowing that no degradative reaction is occurring.
  • the measurement carried out in this way is affected by the error of the under-quantification of oxidized eumelanins by the destruction that has occurred of them during the period necessary for the solubilization of the oxidized eumelanins.
  • the measured value is 136, when according to the extrapolation carried out of the degradation line it should have been 152.
  • eumelanins cannot be carried out directly because they are insoluble, but by means of oxidative treatment, the original eumelanin is transformed into another compound colored and soluble in alkaline medium that can be quantified as in the case of pheomelanin and correlate the value obtained with the eumelanic content original.
  • the characteristics of the product formed are partly pronounced of those of the pheomelanin, such as its solubility in alkaline medium and show an apparent coloration with golden brown tones, very different from the intense black color that intact eumelanins have.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

La présente invention concerne un procédé d'obtention, puis de quantification, de pigments de mélanines, caractérisé en ce qu'il consiste à réaliser un traitement alcalin initial, à séparer les phéomélanines, à obtenir un concentré sec d'eumélanine par lavage du précipité puis par centrifugation, à solubiliser le concentré sec d'eumélanine par oxydation alcaline régulée dans le temps, et à neutraliser les solutions afin d'obtenir des concentrés secs de phéomélanine et de pseudo-phéomélanine. Plus particulièrement, l'invention concerne l'obtention de concentrés secs de phéomélanine, d'eumélanine et de pseudo-phéomélanine naturelles à partir de plumes d'oiseaux ou de poils colorés de mammifère, ainsi que leur utilisation comme matière première à l'échelle industrielle en cosmétique (crèmes, maquillages et teintures) et en dermatologie (pour le traitement de maladies caractérisées par une dépigmentation).
PCT/ES2008/070219 2007-12-21 2008-11-27 Procédé d'obtention de mélanines et applications correspondantes WO2009080857A1 (fr)

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ESP200703395 2007-12-21
ES200703395A ES2322530B1 (es) 2007-12-21 2007-12-21 Procedimiento de obtencion de melaninas y sus aplicaciones.

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140105996A1 (en) * 2011-05-02 2014-04-17 Cocky Smart Pty Ltd Avian-Based Treatment
CN106596425A (zh) * 2016-12-04 2017-04-26 西北农林科技大学 一种检测油菜角果皮光合色素含量的方法
CN109406434A (zh) * 2018-09-14 2019-03-01 安徽大学 一种防晒产品的防晒功效测试方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2203437A (en) * 1987-04-08 1988-10-19 Scopelead Limited The use of hydrolysed hair as an ultraviolet absorbing agent
WO2006018714A1 (fr) * 2004-08-19 2006-02-23 Warner-Lambert Company Llc Essai biologique de melanogenese

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2203437A (en) * 1987-04-08 1988-10-19 Scopelead Limited The use of hydrolysed hair as an ultraviolet absorbing agent
WO2006018714A1 (fr) * 2004-08-19 2006-02-23 Warner-Lambert Company Llc Essai biologique de melanogenese

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
HAYWOOD, R.M. ET AL.: "Synthetic melanin is a model for soluble natural eumelanin in UVA-photosensitised superoxide production", JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY B: BIOLOGY, vol. 82, 2006, pages 224 - 235, XP028056397, DOI: doi:10.1016/j.jphotobiol.2005.12.007 *
ITO, S. ET AL.: "Quantitative Analysis of Eumelanin in Humans, Mice, and Other Animals: a Comparative Review", PIGMENT CELL RESEARCH, vol. 16, 2003, pages 523 - 531 *
KOLCZYNSKA-SZAFRANIEC, U. ET AL.: "Infrared Studies of Natural Pheomelanins", CURRENT TOPICS IN BIOPHYSICS, vol. 16, no. 2, 1992, pages 77 - 80 *
LIU, Y. ET AL.: "Comparison of the Structural and Physical Properties of Human Hair Eumelanin Following Enzymatic or Acid/Base Extraction", PIGMENT CELL RESEARCH, vol. 16, 2003, pages 355 - 365, XP009186851 *
NAPOLITANO, A. ET AL.: "Microanalysis of Melanins in Mammalian Hair by Alkaline Hydrogen Peroxide Degradation: Identification of a New Structural Marker of Pheomelanin", THE JOURNAL OF INVESTIGATIVE DERMATOLOGY, vol. 114, no. 6, 2000, pages 1141 - 1147, XP002352415, DOI: doi:10.1046/j.1523-1747.2000.00977.x *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140105996A1 (en) * 2011-05-02 2014-04-17 Cocky Smart Pty Ltd Avian-Based Treatment
CN106596425A (zh) * 2016-12-04 2017-04-26 西北农林科技大学 一种检测油菜角果皮光合色素含量的方法
CN109406434A (zh) * 2018-09-14 2019-03-01 安徽大学 一种防晒产品的防晒功效测试方法

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ES2322530B1 (es) 2010-04-16

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