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WO2007026035A2 - Aminoacide de type mycosporine (porphyre 334) utilise comme antioxydant - Google Patents

Aminoacide de type mycosporine (porphyre 334) utilise comme antioxydant Download PDF

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Publication number
WO2007026035A2
WO2007026035A2 PCT/ES2006/000488 ES2006000488W WO2007026035A2 WO 2007026035 A2 WO2007026035 A2 WO 2007026035A2 ES 2006000488 W ES2006000488 W ES 2006000488W WO 2007026035 A2 WO2007026035 A2 WO 2007026035A2
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Prior art keywords
porphyra
mycosporin
amino acid
extracted
leucosticta
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Ceased
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English (en)
Spanish (es)
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WO2007026035A3 (fr
Inventor
Francisca De La Coba Luque
José AGUILERA ARJONA
Félix LÓPEZ FIGUEROA
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Universidad de Malaga
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Universidad de Malaga
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/175—Amino acids
    • 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
    • A61K36/02—Algae
    • A61K36/04—Rhodophycota or rhodophyta (red algae), e.g. Porphyra
    • 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
    • A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
    • 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
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/12—Ophthalmic agents for cataracts
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • 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
    • 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

Definitions

  • the present invention is part of the biotechnology sector and describes the potential use as antioxidant substances of certain secondary metabolites called mycosporin-type amino acids (MAAs) isolated from red algae and marine lichens in addition to their possible application in pharmaceutical preparations, nutraceuticals, functional foods for the prevention of oxidative stress.
  • MAAs mycosporin-type amino acids
  • UV radiation is one of biological factors that limit the survival, physiology and growth of many organisms. Some of the multiple harmful effects of UV radiation include the alteration of DNA and protein molecules, inactivation of enzymes and the formation of free radicals, which attack cell membranes and other target molecules altering their functionality. All aerobic organisms have a wide variety of both enzymatic and non-enzymatic antioxidant defense systems that cooperatively coordinate and protect the body from the risks of oxidative stress.
  • SOD superoxide dismutase
  • GPX glutathione peroxidase
  • CAT catalase
  • Free radical means any chemical species that contains one or more missing electrons in its external orbitals so that a compound can become a free radical by capturing or losing an electron.
  • free radicals of a very different nature exist, it is the species that derive from the oxygen molecule (ROS) the most abundant in aerobic organisms, highlighting products of the rupture or excitation of O 2 such as singlet oxygen 1 O 2 and species of oxygen that are partially reduced such as the bidroxyl radical (OH » ), superoxide anions (O 2 " ) and hydrogen peroxide (H 2 O 2 ). These unstable molecules travel through the body taking electrons, thus recovering their electrochemical stability.
  • ROS oxygen molecule
  • Free radicals give rise to important alterations in molecules such as
  • DNA, lipids and proteins seriously altering the cycle and cellular functionality.
  • the DNA can suffer loss of bases as well as the rupture of one or both strands of the genetic material, alterations that can result in irreversible mutations.
  • Many proteins are capable of absorbing a large amount of oxidation without apparently affecting their function.
  • the damage caused by OH » and 1 O 2 are irreversible and generally mark the proteins for degradation.
  • Cell membranes can also be seriously damaged in oxidative stress because phospholipids that have fatty acids with several double bonds are very susceptible to oxidation due to the loss of a hydrogen (allyl).
  • allyl Once the carbon radical has been generated in a fatty acid, it reacts with molecular oxygen forming a peroxyl radical.
  • the peroxyl radical can take an allylic hydrogen to another methylene whereby the reaction is propagated.
  • Hydroperoxides which are stable compounds, if they come into contact with transition metal ions will produce more free radicals that will initiate and propagate other chain reactions. Thus, the membranes are seriously damaged and therefore their functionality is altered.
  • Free radicals are associated with a wide range of pathologies and diseases such as Alzheimer's or Parkinson's and conditions related to sun exposure such as the appearance of cataracts, photoaging, inflammatory episodes and neoplasms. They are also responsible for the oxidation of food fats, which is the most important form of deterioration after alterations caused by microorganisms. With oxidation, stale odors and flavors appear, the color and texture are altered, and the nutritional value decreases when some vitamins and polyunsaturated fatty acids are lost. In addition, products formed in oxidation can become harmful to health.
  • Mycosporin-type amino acids consist of a cyclohexenone or cyclohexenimine ring, conjugated with a nitrogenous substituent of an amino acid or its amino alcohol that acts as a chromophore allowing the absorption of certain shortwave radiation.
  • the metabolites that are isolated in fungi have an absorption range between 310 and 320 nm and have cyclohexenone rings exclusively, being known by the name of mycosporins in reference to their origin.
  • metabolites that are isolated from marine organisms and algae contain cyclohexenimine rings, with maximum absorptions between 310 and 360 nm and they are known as mycosporin-like amino acids ⁇
  • mycosporine-glycine and mycosporine taurine are aminocyclohexenones isolated from marine organisms.
  • mycosporins described in fungi and 23 MAAs in marine organisms. They are small molecules, with molecular weights around 330 Da and have high photostability. They behave like amphoteric molecules, similar to amino acids, so that they have positive and negative charges on the same molecule. They show physicochemical characteristics of ionic compounds, for example, high effusion point and high water solubility.
  • patent US2004228875 refers to the antioxidant properties of extracts obtained from algae of the genus Porphyra, although without concluding on the possible role played by MAAs.
  • An antioxidant is defined as a substance that in low concentrations compared to an oxidizable substrate, delays or prevents its oxidation.
  • the present invention describes the potentiality of the porphyra 334 MAA isolated from Porphyra leucosticta as a radical scavenger and lipid peroxidation inhibitor. In the tests carried out, the new antioxidant is compared with another known antioxidant, ⁇ -tocopherol.
  • the described compound could be used in therapeutic applications, and in non-medical applications for the stabilization of compounds susceptible to oxidative deterioration, in the preservation of food or related products, and in nutritional, nutraceutical, functional or parapharmaceutical supplements for their antioxidant properties for prevent oxidative stress.
  • MAAs are found naturally in isolated organisms in the order of mg / g PS, highlighting porphyra 334 found in the Porphyra leucosticta algae in the order of 3-6 mg / gPS.
  • seaweed has been used as human food since ancient times, especially in Eastern countries and whose culture is expanding worldwide.
  • Porphyra (whose vulgar name in Japan is nori) is one of the most seaweed important used as human food.
  • Porphyra has been listed in Japanese fisheries statistics as the third catch in order of importance and has a high content of valuable edible proteins so that this study could give added value to certain types of natural foods.
  • the present invention presents an isolated compound of Porphyra leucosticta with the following structure and useful as an antioxidant and free radical sequestrant.
  • Preparative scale extraction was performed by dissolving 60-80 g (PF) of biological material in 1 liter of methanol to 20% v / v and incubated in a thermostatic bath at 45 0 C for
  • the purification was performed in three consecutive steps in which chromatographic absorption techniques are combined by the application of active carbon, precipitation of polysaccharides by adding 100% methanol to the sample and final separation by ion exchange chromatography. Finally, aqueous solutions of MAA were obtained in a high degree of purity at concentrations of the order of mM.
  • Antioxidant capacity of mycosporin-like amino acids To measure the activity as a water-soluble radical sequestrant, the ABTS peroxidase method has been used, which allows to determine the total antioxidant activity (TAA) of a sample understood as a parameter that allows quantifying the capacity of a sample, natural or processed, of sequestering free radicals present in an aqueous solution.
  • TAA total antioxidant activity
  • Porphyra 334 isolated from Porphyra leucosticta has no significant antioxidant activity at any pH tested as an inhibitor of water-soluble free radical production (ABTS + I
  • Porphyra 334 isolated from Porphyra leucosticta was studied as an inhibitor of lipid peroxidation in vitro using the ⁇ -carotene bleaching technique.
  • the method of decolorization of ⁇ -carotene is widely used to determine the antioxidant capacity of various substances in lipophilic medium, most of them extracted from fruits, vegetables and other products intended for food consumption in order to determine their greater or lesser degree of self-preservation in a natural state.
  • ⁇ -tocopherol ( ⁇ -TOC) was used as a positive control.
  • Porphyra 334 isolated from Porphyra leucosticta shows moderate antioxidant activity at the level of lipid peroxidation inhibition. It is thus constituted as an antioxidant of moderate activity in vitro.
  • this compound in extracts or preparations containing it, could be used in pharmaceutical preparations or formulations for the prevention and therapeutic treatment of diseases or conditions related to free radicals, in parapharmacy products, in functional foods, nutritional supplements and nutraceutical preparations, and in the food industry as an antioxidant potential (additive).
  • FIG. 3 Dose ( ⁇ M) - antioxidant activity response (%) of porphyra 334 isolated from Porphyra leucosticta with respect to 10 ⁇ M of ⁇ -tocopherol by the method of decolorization of ⁇ -carotene. The values represent the mean values and standard deviation of 3 experiments. Porphyra 334 isolated from Porphyra leucosticta is a good antioxidant at a concentration of 100-200 ⁇ M.
  • the mobile phase used was 2.5% methanol (v / v, HPLC quality) plus 0.1% acetic acid (v / v) isocratically pumped at a flow rate of 0.5 ml min "1.
  • a UV detector was used.
  • Figure 1 shows the percentages in area of the chromatographed peaks of different algal extracts, some identified as MAAs and others unknown. Purification objective was to isolate the major MAA in Porphyra leucosticta in the aqueous phase, in addition to removing traces and other types of unidentified compounds.
  • Preparative scale extraction was performed by dissolving 60-80 g (PF) of biological material in 1 liter of methanol to 20% v / v and incubated in a thermostatic bath at 45 0 C for 2 hours. Extract at 14,000 rpm for 15 min and then centrifuged at rotary evaporation 45 was 0 C to remove part of the methanol in the sample.
  • the purification is carried out in three consecutive steps in which chromatographic absorption techniques are combined by the application of active carbon, precipitation of polysaccharides by adding 100% methanol to the sample and final separation by ion exchange chromatography (Dowex 50 W x 8 resin -100).
  • chromatographic absorption techniques are combined by the application of active carbon, precipitation of polysaccharides by adding 100% methanol to the sample and final separation by ion exchange chromatography (Dowex 50 W x 8 resin -100).
  • double-distilled water was used as eluent, with a slightly alkaline pH (7.2).
  • aqueous solutions of MAA were obtained in a high degree of purity at concentrations of the order of mM.
  • the ABTS peroxidase method allows to determine the total antioxidant activity (TAA) of a sample understood as a parameter that allows quantifying the capacity of a sample, natural or processed, of sequestering free radicals present in an aqueous solution.
  • TAA total antioxidant activity
  • This parameter is aimed at giving information on the antioxidant activity that a specific sample can present, regardless of the partial activities that each of its components may present or the synergism effects that could be established.
  • ABTS 2,2'- Azino -bis- (3- ethyl-benzothiazoline-6- sulfonic acid) or ABTS is a compound that has high chemical stability, high water solubility and maximum absorption in the UVA band at 342 nm .
  • This compound in the presence of H 2 O 2 and peroxidases enzymes derives to a metastable radical (ABTS + ) with a characteristic absorption spectrum and different from ABTS, presenting maximum absorption in the UV spectral region and visible at 413, 645, 727 and 811 nm.
  • ABTS is a product that has great stability over a wide pH range, showing the same absorbance spectrum at pH 4 and pH 8.5.
  • the formation of the ABTS + radical is also carried out in that pH range but the enzymatic activity of the peroxidase itself is dependent on the pH of the reaction medium so that when the activity is alkalized the activity decreases, thus increasing the period of delay or "lag time".
  • the activity of our enzyme could be adjusted to an exponential curve so that it is maximum at pH 4.5 and ceases to be active at pH higher than 10.
  • Our assays will run at pH 6-8.5 so that we ensure the activity of the enzyme.
  • the quantification of the free radical sequestration capacity of a sample is carried out by decolorization tests in which the formation of ABTS + results in a characteristic coloration that will decrease proportionally to the amount of substances capable of trapping these. radicals added to the reaction volume. This loss of color can be measured by kinetic monitoring of loss of absorbency at 413 nm (wavelength that does not interfere with other molecules) over a minute using HRP as peroxidase and ascorbic acid (L-ASC) as a negative control. .
  • the reaction medium is composed of 50 mM phosphate buffer pH 6, 7.5, 8, 2 mM H 2 O 2 , 2 mM ABTS, 0.25 ⁇ M HRP enzyme and sample at increasing concentrations.
  • TAA The calculation of TAA is established according to the relationship between the slopes (Abs / min) of enzymatic tests in which the course of the reaction is estimated in the absence of antioxidants (positive control), and in the presence of different concentrations of substances with possible activity antioxidant
  • the slope of the control kinetics would correspond to a TAA of zero percent, based on this the percentage of inhibition of the other curves.
  • Lipid peroxidation is a well-established mechanism of cell damage in plants and animals, as well as food spoilage (thickening). This process leads to the production of lipid peroxides and degradation aldehydes that leads to loss of cell membrane function and integrity.
  • Porphyra 334 isolated from Porphyra leucosticta was studied as an inhibitor of lipid peroxidation in vitro using the ⁇ -carotene bleaching technique.
  • the method of decolorization of ⁇ -carotene is widely used to determine the antioxidant capacity of various substances in lipophilic medium, most of them extracted from fruits, vegetables and other products intended for food consumption in order to determine their greater or lesser degree of self-preservation in a natural state. It is a spectrophotometric method that measures the inhibition caused by an antioxidant on the discoloration of ⁇ -carotene in an aqueous system emulsified with Tween 20 and linoleic acid.
  • Linoleic acid self-oxidizes at a high rate in the presence of specially activated hydrogen atoms.
  • ⁇ -carotene a precursor to vitamin A, is also known as a lipophilic antioxidant that prevents lipid peroxidation in membranes by sequestering singlet oxygen molecules and peroxyl lipid radicals.
  • the ⁇ -carotene when it is in the presence of linoleic acid, yields electrons by delaying the initiation stage of the linoleic acid self-oxidation process as well as limiting the propagation phase of the damage by simultaneously eliminating formed peroxidic radicals.
  • ⁇ -carotene has a maximum absorption at 470 nm. This maximum varies when the molecule oxidizes since it loses double bonds and the structure of the molecule's chromophore is altered, thus losing its characteristic orange color and can be detected spectrophotometrically.
  • the absorbency of the reaction medium will remain unchanged over time in the presence of antioxidant substances, with a drop in the absorbency of the sample when measured in the absence of antioxidants.
  • the measurement of the antioxidant capacity of a substance will be inversely proportional to the slope drop of the curve that describes the oxidation of ⁇ -carotene (measured at the wavelength of
  • ⁇ -tocopherol ( ⁇ -TOC) was used as a positive control.
  • P refers to the slopes of the obtained fading curves (Abs / time).
  • the superoxides (O 2 ' ) radicals are mediators of autooxidation reactions of some compounds. Most of the time these oxidized compounds are characterized by having a characteristic absorption spectrum quantifiable by spectrophotometry. Pyrogallol (1,2,3-benzenotriol) is a substance that rapidly oxidizes in the presence of oxygen, especially in alkaline solutions. At pH 7.9 the SOD inhibits 99% of the reaction indicating a practically total participation of the superoxide anion O 2 " in the reaction.
  • the oxidized pyrogallol has a maximum absorption at 420 nm so that the ability of MAAs to sequester superoxide radicals was measured as loss of absorbency of spectrophotometrically monitored kinetic assays (Shimadzu UV 1603) during one minute of reaction.
  • the protocol that was carried out was based on Marklund & Marklund (1974, Eur. J. Biochem., 47: 469-474 ) with some modifications.
  • the reaction mixture contained 0.4 mM pyrogallol and MAA at different concentrations in 50 raM phosphate buffer at pH 8.2, containing 1 mM diethylenetriaminepentaacetic acid in a final volume of ImI incubation.
  • the temperature was stable at 20 ⁇ 1 0 C.
  • the positive control was the kinetic curve of generation of oxidized pyrogallol radicals in the absence of antioxidants to compare them with different concentrations of SOD as a known antioxidant. Dose-response relationships for the MAAs under study were determined at different concentrations.
  • the sequestration capacity of superoxide radicals of the purified extracts was evaluated according to the following formula:
  • P refers to the slopes of the kinetic oxidation curves of pyrogallol (Abs)

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Abstract

L'invention porte sur un aminoacide de type mycosporine (porphyre 334) utilisé comme antioxydant. L'invention concerne le secteur biotechnologique et décrit l'utilisation éventuelle d'un aminoacide de type mycosporine (MAA), en particulier de la porphyre 334 isolée de l'algue rouge Porphyra leucostica, comme substance antioxydante. L'invention concerne également l'utilisation éventuelle dudit aminoacide dans des préparations pharmaceutiques, nutritionnelles ou dans des aliments fonctionnels, notamment pour la prévention du stress oxydatif.
PCT/ES2006/000488 2005-08-31 2006-08-28 Aminoacide de type mycosporine (porphyre 334) utilise comme antioxydant Ceased WO2007026035A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ES200502161A ES2301293B1 (es) 2005-08-31 2005-08-31 Uso de aminoacido tipo micosporina (porphyra 334) como antioxidante.
ESP200502161 2005-08-31

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WO2007026035A2 true WO2007026035A2 (fr) 2007-03-08
WO2007026035A3 WO2007026035A3 (fr) 2007-05-10

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102196422B1 (ko) * 2019-07-15 2020-12-30 주식회사 바이오에프디엔씨 포피라334를 이용한 성체세포를 유도만능 줄기세포로 역분화시키는 방법

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Publication number Priority date Publication date Assignee Title
ES2317741B1 (es) * 2006-06-20 2010-02-10 Universidad De Malaga Composicion para proteccion solar a base de extractos de algas y liquenes.

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2655268B1 (fr) * 1989-12-06 1994-10-14 Secma Utilisation d'extraits d'algues pour la preparation de compositions pharmaceutiques, cosmetiques, alimentaires ou a usage agricole.
CA2251457A1 (fr) * 1998-10-23 2000-04-23 Norman Huner Compositions comprenant des composes d'origine naturelle tires de plantes, d'algues et de cyanobacteries pour la protection contre les rayons solaires
FR2803201B1 (fr) * 1999-12-30 2004-11-26 Gelyma Extrait d'algue a activite filtrante vis a vis des radiations ultraviolettes
GB0028161D0 (en) * 2000-11-17 2001-01-03 Natural Environment Res Personal care compositions
WO2003041679A2 (fr) * 2001-11-14 2003-05-22 Larena Produit contenant un extrait d'algue rouge du genre porphyra
FR2882894B1 (fr) * 2005-03-11 2009-04-03 Larena Sa Composition alimentaire suppletive

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102196422B1 (ko) * 2019-07-15 2020-12-30 주식회사 바이오에프디엔씨 포피라334를 이용한 성체세포를 유도만능 줄기세포로 역분화시키는 방법

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ES2301435A1 (es) 2008-06-16
ES2301434A1 (es) 2008-06-16
ES2301433A1 (es) 2008-06-16
ES2301434B1 (es) 2009-05-01
WO2007026035A3 (fr) 2007-05-10
ES2301436A1 (es) 2008-06-16
ES2301293A1 (es) 2008-06-16
ES2301437A1 (es) 2008-06-16
ES2301436B1 (es) 2009-05-08
ES2301437B1 (es) 2009-05-01
ES2301293B1 (es) 2009-05-01
ES2301435B1 (es) 2009-05-01

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