WO2011096628A1 - 홍조류로부터 비독성 자외선 차단용 추출물을 제조하는 방법 및 이를 이용한 비독성 자외선 차단제 - Google Patents

홍조류로부터 비독성 자외선 차단용 추출물을 제조하는 방법 및 이를 이용한 비독성 자외선 차단제 Download PDF

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WO2011096628A1
WO2011096628A1 PCT/KR2010/006099 KR2010006099W WO2011096628A1 WO 2011096628 A1 WO2011096628 A1 WO 2011096628A1 KR 2010006099 W KR2010006099 W KR 2010006099W WO 2011096628 A1 WO2011096628 A1 WO 2011096628A1
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extract
toxic
sunscreen
red algae
hydrophobic
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PCT/KR2010/006099
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English (en)
French (fr)
Korean (ko)
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한태준
박진희
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인천대학교 산학협력단
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Priority to CN201080063299.5A priority Critical patent/CN102740869B/zh
Priority to JP2012551898A priority patent/JP2013518871A/ja
Publication of WO2011096628A1 publication Critical patent/WO2011096628A1/ko

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    • 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
    • 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
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • A61K2236/30—Extraction of the material
    • A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
    • A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH

Definitions

  • the present invention relates to a method for producing a non-toxic sunscreen extract from red algae and a non-toxic sunscreen using the extract, more specifically, Mycosporine-like amino acids (MAA) content of red algae It relates to a method for producing a non-toxic sunscreen extract from relatively high laver or jindubal and a non-toxic sunscreen using the ultraviolet absorption properties of the non-toxic sunscreen extract.
  • MAA Mycosporine-like amino acids
  • UV light not only causes acute skin reactions such as erythema, but also causes skin aging and skin cancer after prolonged exposure.
  • Ultraviolet ray (UV ray) included in the sunlight reaching the earth is divided into two areas according to the wavelength. UV-A (320-400 nm), which is long wave, and UV-B (280-, which is medium wave) 320 nm).
  • UV-B which is relatively energetic, is absorbed into the skin layer and is known to cause acute skin desorption, DNA mutation, or cancer.
  • UV-A is less energy than UV-B
  • UV-A is known to penetrate deeper than UV-B and cause premature skin aging. It causes the same inflammatory symptoms and alters the expression of genes. It is reported that UV-A activates transcription factors such as NF- ⁇ B and AP-1. The activation of transcription factors by UV-A induces a series of collagen and elastin degrading enzymes called matrix metalloproteinases (MMP's), resulting in reduced collagen content and fibrin fragmentation ultimately leading to typical photoaging. do.
  • MMP's matrix metalloproteinases
  • UV-A is well absorbed by urocanic acid or DNA, which is a pigment of the skin, and as a result, free radicals are generated and react with important molecules such as proteins and lipids, thereby destroying important biomolecules or losing their function.
  • UV-B The amount of UV-B varies depending on the season, time of day, cloud presence, latitude, etc., whereas UV-A reaches relatively high levels throughout the year. Protection is more important.
  • Sunscreens used to protect the skin from ultraviolet rays are largely divided into inorganic particle forms and organic compound forms.
  • the sunscreen agent in the form of inorganic particles includes inorganic particles such as ultrafine mineral particles such as zinc oxide, titanium dioxide and iron dioxide, and the inorganic particles adhere to the skin surface and serve as a barrier for reflecting sunlight (ultraviolet rays). do.
  • sunscreens in the form of inorganic particles keeps the skin cool, provides natural sun (ultraviolet) protection, and is not absorbed by the skin, which does not cause skin problems, while giving a heavy feeling to the skin and residue on the skin. There is a problem that leaves.
  • sunscreens in the form of organic compounds include active synthetic compounds that absorb UV light very well, such as parmeth (Dimethico-diethylbenzalmalonate, Parsol), benzophenone (Sodium Dihydroxy Dimethoxy Disulfobenzophenone), and paba (p-Aminobenzoic acid (PABA)).
  • UV-A penetrates deep into the skin, causing aging in collagen fibers and other tissues, and preventing sunburn or skin cancer from being induced by UV-B. And the disadvantage that it can easily decompose or produce free radicals, and recently, it has been reported that the organic compounds can cause side effects including endocrine disorders.
  • the present invention has been derived to solve the above problems, one object of the present invention is to produce a non-toxic sunscreen extract that can be used as a main component of the sunscreen with excellent UV absorption ability without phototoxicity or cytotoxicity, etc. To provide a method.
  • Another object of the present invention to provide a non-toxic sunscreen using a non-toxic sunscreen extract.
  • the inventors of the present invention through a myriad of experiments when extracting a sunscreen extract containing mycosporine-like amino acids (MAA) known as UV-A blocking material from seaweed and jindubal in red algae
  • MAA mycosporine-like amino acids
  • the present invention has been found to have a higher yield than when extracted from brown algae and red algae plants, and that the UV-protective extracts extracted from laver and laver are very low in phototoxicity and cytotoxicity.
  • the present invention comprises the steps of (a) preparing at least one red alga selected from laver or jindubal; (b) adding a mixed solvent having a volume ratio of 1 to 5 carbon atoms to water of 1: 9 to 9: 1 to the prepared red algae and maintaining the temperature at a temperature of 30 to 60 ° C. to extract the active ingredient; And (c) filtering the mixed solvent including the active ingredient and the remaining red algae solids into a supernatant and the remaining red algae solids. It provides a method for producing a non-toxic sunscreen extract comprising a.
  • the method for producing a non-toxic UV protection extract according to the present invention may preferably further comprise (d) removing impurities by passing the separated supernatant through a membrane filter.
  • the method for producing a non-toxic UV protection extract according to the present invention preferably comprises the steps of (e) concentrating and drying the separated supernatant or the supernatant from which impurities are removed to obtain a solidified crude extract; can do.
  • the method for preparing a non-toxic UV protection extract according to the present invention is preferably (f) dissolving the solidified crude extract in water when the solidified extract is not subjected to the step of removing impurities by a membrane filter. Passing through the membrane filter to remove impurities; may further include.
  • the method for producing a non-toxic UV protection extract according to the present invention is preferably (g) to the concentration gradient of water and alcohol having 1 to 5 carbon atoms in the crude extract aqueous solution from which impurities are removed by the step (f). Expanding and obtaining a crude extract fraction absorbing the ultraviolet wavelength of 280 ⁇ 400 nm; may further include. At this time, the UV detector is used to measure the absorption of the ultraviolet wavelength, and supplementary RI (refractive index) may be further used.
  • the method for producing a non-toxic sunscreen extract according to the present invention may preferably further comprise (h) passing the crude extract fraction through a hydrophobic mutual column to obtain a primary purified extract.
  • the method for producing a non-toxic UV protection extract according to the present invention preferably comprises the steps of (i) passing the first purified extract through a size exclusion column (Size Exclusion Column) to obtain a second purified extract; It may further include.
  • the method for producing a non-toxic sunscreen extract according to the present invention may preferably further comprise the step (j) to concentrate and dry the secondary tablet extract to obtain a solidified tablet extract.
  • the present invention provides a non-toxic sunscreen comprising a non-toxic sunscreen extract prepared by the above method.
  • the sunscreen extract contains Mycosporine-like amino acids (MAA) as an active ingredient, and as a kind of Mycosporine-like amino acids (MAA) contained, parine ( Palythine), Asterina-330, and Shinorine, and further include Porphyra-334.
  • Mycosporine-like amino acids (MAAs) have a cyclohexanone or cyclohexenimine pigment structure that absorbs UV light well in the UV-A (320-400 nm) region. The extinction coefficient is similar to that of the artificial sunscreen (sunscreen).
  • the method for preparing the non-toxic sunscreen extract according to the present invention uses laver or jindubal as an extraction material, the yield of the sunscreen extract containing Mycosporine-like amino acids (MAA) is increased. It has a relatively significant advantage over extraction from other green algae, brown algae and red algae plants.
  • the sunscreen extract extracted from laver or jindubal has very low phototoxicity and cytotoxicity, while at the same time giving irritating dermatitis, contact dermatitis, photoallergic or phototoxic dermatitis without giving heavy feeling to the skin or foreign substance by residue It can be used as a major component of sunscreens without side effects such as skin irritation, allergic reactions, and toxicity.
  • Figure 1 shows the process of the method for producing a non-toxic anti-UV extract according to an embodiment of the present invention.
  • Figure 2 is a graph showing the phototoxicity results of the non-toxic UV protection crude extract (PE) and secondary purified extract (P7) extracted from seaweed according to the photohemolysis test using human red blood cells.
  • PE non-toxic UV protection crude extract
  • P7 secondary purified extract
  • Figure 3 is a photograph showing the phototoxicity results according to the photohemolysis test using human erythrocytes when the concentration of non-toxic UV protection crude extract (PE) extracted from seaweed is 500 ⁇ g / ml.
  • PE non-toxic UV protection crude extract
  • Figure 4 is a photograph showing the phototoxicity results according to the photohemolysis test using human erythrocytes when the concentration of the non-toxic UV protection secondary tablet extract (P7) extracted from seaweed is 250 ⁇ g / ml.
  • One aspect of the present invention relates to a method for preparing a non-toxic sunscreen extract that can be used as a main component of a sunscreen because there is no phototoxicity or cytotoxicity and excellent UV absorption ability.
  • a method for producing a non-toxic UV protection extract according to the present invention will be described step by step through FIG.
  • Figure 1 shows a process of a method for producing a non-toxic UV protection extract according to a preferred embodiment, the technical idea of the present invention is not limited or limited to this can be variously modified by those skilled in the art Of course.
  • Laver or Jindubal is one of the red algae (Rhodophyta) plants, and according to the research of the present inventors, green algae, brown algae and red algae plants having different yields of sunscreen extracts containing Mycosporine-like amino acids (MAA) It has a relatively significant advantage over extraction from.
  • the laver or jindubal preferably uses dried ones, and more preferably, pulverized. Crushed laver or soybean hair has a very large surface area to improve extraction speed reading and extraction yield by the extraction solvent. Steaming or head can be crushed through a mortar or mortar or the like.
  • the extraction solvent is added to the red algae such as crushed laver or jindubal and maintained at a predetermined temperature to extract the active ingredient.
  • water, alcohol, or a mixed solvent of water and alcohol is used as the extraction solvent.
  • the volume ratio of alcohol to water is 1: 9 to 9: 1 mixed solvent, and more preferably, the volume ratio of alcohol to water is 4: 1. It is characterized by that. If the volume ratio of alcohol to water is lower than 1: 9, the content of alcohol is too small to reduce the extraction rate and extraction yield. If the volume ratio of alcohol to water is greater than 9: 1, the extraction rate and the increase rate of extraction rate are increased with the increase of alcohol content. It is not large, so it is inferior in economic efficiency, and the extraction rate, extraction yield, and economics are optimal when the volume ratio of alcohol to water is 4: 1.
  • Alcohols are those having 1 to 5 carbon atoms, preferably methanol or ethanol, more preferably methanol. When using methanol the extraction rate and extraction yield are higher than other alcohols.
  • the extraction temperature is not particularly limited in the range, but is preferably about 30 ⁇ 60 °C. If the extraction temperature is less than 30 °C extraction rate and extraction yield is too low and if the extraction temperature exceeds 60 °C some of the alcohol is vaporized and not available for extraction.
  • the mixed solvent including the active ingredient and the remaining red algae solid is filtered to separate the supernatant and the remaining red algae solids.
  • the filter medium used for the filtration is not particularly limited as long as it can effectively separate the supernatant from the remaining red algae solids.
  • the filter medium or the filter cloth has a pore size of about 0.1 ⁇ m to 0.005. It has a range of mm.
  • the remaining red algae solids separated by filtration after one extraction have an active ingredient such as Mycosporine-like amino acids (MAA), which is not extracted.
  • MAA Mycosporine-like amino acids
  • the method for producing the extract for non-toxic UV protection according to the present invention may further comprise the step of removing impurities by passing the separated supernatant through a membrane filter (Membrane filter).
  • the membrane filter is a membrane having a nano-sized pore size (less than about 100 nm) and serves to remove impurities, contaminants, and the like contained in the filtered supernatant from the supernatant.
  • the crude extract is obtained by solidifying the filtration separation or membrane filtered supernatant by concentration and drying.
  • the concentration of the supernatant is preferably characterized by concentration under reduced pressure, and drying is characterized by freeze drying.
  • concentration under reduced pressure the extraction solvent can be easily evaporated at low temperature, and the extract solidifies at low temperature by lyophilization, thereby preventing the active ingredient of the extract from being denatured by heat.
  • Crude crude extract is dissolved in water to prepare an aqueous crude extract.
  • the crude extract of the crude extract aqueous solution is not subjected to the membrane filter treatment in the manufacturing process, the crude extract aqueous solution is passed through the membrane filter to remove impurities and the like.
  • the crude extract aqueous solution from which impurities are removed is subjected to the fractionation and purification steps described below.
  • the supernatant after filtration and membrane filter treatment may be fractionated and purified.
  • the supernatant subjected to the filtration and membrane filter treatment was developed with a water-alcohol concentration gradient, and 280- in the developed crude extract aqueous solution.
  • a crude extract fraction is obtained which absorbs an ultraviolet wavelength of 400 nm.
  • an alcohol having 1 to 5 carbon atoms is used, and preferably methanol.
  • a specific example of the development of the water-alcohol concentration gradient is a method of sequentially developing water, an aqueous 50% alcohol solution.
  • a UV detector is used to measure the fraction of absorbing the ultraviolet wavelength of 80 ⁇ 400 nm in the developed extraction extract aqueous solution or supernatant, supplementary RI (refractive index) may be further used.
  • the collected crude extract fractions are passed through a hydrophobic mutual column to obtain a primary purified extract.
  • the type of hydrophobic cross-column used here is not limited, and specifically, a hydrophobic alkyl group, a hydrophobic aryl group, a hydrophobic cyano group, and a hydrophobic alkyl group on the surface of a base particle made of agarose gel, silica gel, or organic polymer resin, and One hydrophobic functional group selected from the group consisting of hydrophobic amine groups is combined.
  • Hydrophobic alkyl groups include butyl, octyl, and octadecyl groups.
  • Hydrophobic aryl groups include phenylethyl groups, hydrophobic cyano groups include cyanopropyl groups, and hydrophobic amine groups include aminopropyl groups.
  • the hydrophobic cross column used in the present invention is preferably characterized in that one hydrophobic functional group selected from the group consisting of a hydrophobic alkyl group, a hydrophobic aryl group, a hydrophobic cyano group, and a hydrophobic amine group is bonded to a silica gel surface.
  • Such hydrophobic interaction columns include CAPCELL PAK C8, CAPCEll PAk C18, etc. manufactured by Shiseido, Japan.
  • the CAPCELL PAK C18 is a single layer formed by depositing a silicon (Silicone) polymer on the surface of the gel-type silica gel to combine the octadecyl group on the single layer surface.
  • a silicon (Silicone) polymer on the surface of the gel-type silica gel to combine the octadecyl group on the single layer surface.
  • an aqueous acetic acid solution is used.
  • the primary purified extract is passed through a size exclusion column to obtain a secondary purified extract.
  • the size exclusion column to be used in the water-soluble system is not limited in kind, specifically, Shiseido's silica base water-based size exclusion column (KW-800 series, KW-400 series), polyhydroxy methacrylate Base size exclusion columns (OHpak series) and the like.
  • the secondary purified extract is concentrated and dried to give a solidified purified extract.
  • Concentration of the secondary purified extract is preferably characterized by concentration under reduced pressure, and drying is characterized by freeze drying.
  • solvents such as water can be easily evaporated at a low temperature, and when the freeze-dried solidifies the purified extract at a low temperature, the active ingredient of the purified extract can be prevented from being denatured by heat.
  • Another aspect of the present invention relates to a non-toxic sunscreen using a non-toxic sunscreen extract prepared by the production method according to the present invention.
  • the non-toxic sunscreen extract according to the present invention contains Mycosporine-like amino acids (MAA) as an active ingredient, and palytin (Mycosporine-like amino acids (MAA)). Palythine), Asterina-330 (Asterina-330), and Shinorine (Shinorine), and further includes Porphyra-334 (Porphyra-334), and excellent UV-A absorption capacity.
  • the non-toxic sunscreen extract (particularly the secondary tablet extract) according to the present invention can be used as a main component of the non-toxic sunscreen is very low phototoxicity or cytotoxicity.
  • non-toxic sunscreen extract as an active ingredient non-toxic sunscreen extract according to the present invention about 0.05 to 10% by weight, oil medium medium about 5 to 40% by weight, emulsifier about 1 to 10% by weight, trace amounts of auxiliary and residual amount Water phase media such as water.
  • Oily media include hydrocarbon oils such as paraffin and mineral oils, paraffin waxes, natural oils, silicone oils, fatty acid esters such as isopropyl palmitate, fatty acid alcohols such as stearyl alcohol, and oily media are water in water. It constitutes an oily component in oil or oil in water.
  • Emulsifiers include sorbitan esters (trade name SPAN), ethoxylated sorbitan esters (Sorbitan eser, trade name Tween), silicone polyols, potassium stearate, ethoxylated fatty acid esters, and the like.
  • Adjuvants include emollients, humectants, antioxidants, emulsion stabilizers, thickeners, preservatives, fragrances, colorants, and the like, which are commonly included in sunscreens.
  • Table 1 shows the results of ultraviolet absorption of the extract extracted from the green algae sample
  • Table 2 shows the results of ultraviolet absorption of the extract extracted from the brown algae sample
  • Table 3 shows the results of ultraviolet absorption of the extract extracted from the red algae sample.
  • Agardh 329 Hypnea charoides Lamouroux 320 Lomentaria catenata Harvey 330 Porphyra suborbiculata Kjellman 334 Porphyra yezoensis 337 Pachymeniopsis elliptica Yamada 328, 330, 334 Phacelocarpus japonicus Okamura 300 Pterocladia tenuis Okamura 334 Plocamium telfairiae Harvey 322 (trace) Schizymenia dubyi J. Agardh 334
  • red algae extracts As most of the red algae extracts were examined for the presence of UV-absorbing substances, four mycosporine-like amino acids (MAA), parlythine and asterina-330, were identified for red algae extracts. (Asterina-330), Shinorine, Porphyra-334 (Porphyra-334) were used as a standard to analyze the content of mycosporin-like amino acid components in red algae extracts, the results are shown in Table 4. . Analysis was performed by high performance liquid chromatography.
  • the yield based on the total content of the four Mycosporine-like amino acids (MAA) standards is about 1.7% in the Porphyra extract and about in the Chondrus extract. It was 1.3% higher than other red algae extracts (about 0.3 ⁇ 0.7%).
  • the seaweed extract contained all four standard substances, and showed a very high content of porphyrin-334.
  • the extract of Jindubal included three standard substances except porphyrin-334, and the content of palatin was found to be very high. Based on the results examined above, seaweed and jindubal were selected as candidates for the sunscreen extract.
  • the crude extract aqueous solution from which impurities are removed is composed of Prep LC system (dual pump (Koto, Japan), auto injector, UV / RI detector, and fraction collector) in water-methanol concentration gradient (first water, then 50% by volume methanol solution).
  • Prep LC system dual pump (Koto, Japan), auto injector, UV / RI detector, and fraction collector) in water-methanol concentration gradient (first water, then 50% by volume methanol solution).
  • the crude extract fraction absorbing the ultraviolet wavelength of 280-400 nm was obtained using UV detector and RI detector after development ().
  • the obtained crude extract fractions were developed at a rate of 10 ml / min with a 0.2% by volume aqueous acetic acid solution in a hydrophobic cross column (Capcellpak C18 UG120 semi-prepatative column; Shiseido, Japan) protected by a UG120 guard column (Shiseido, Japan). It was purified first. The first purified extract was purified on a size exclusion column (Ohpak 2002; Shiseido, Japan) with water at a rate of 2.5 ml / min for second purification. The secondary tablet extract was a bright yellow liquid, which was concentrated on a vacuum evaporator and lyophilized to give a solidified tablet extract (P7).
  • the photohemolysis test (Photohemolysis Test), which is known as an effective method of screening, was applied to evaluate phototoxicity. Fibrosismolecule derived from mouse (NIH / 3T3) was used for the 3T3 NRU phototoxicity test, and human erythrocytes (Human Erythrocyte) were used for the photohemolysis test.
  • the 3T3 neutral red uptake photoxicity test (3T3 NRU PT) was adopted as an alternative to the evaluation of cosmetic phototoxicity in April 2004 as an OECD Toxicity Test standard. It is an evaluation method to classify the cytotoxicity between light irradiated and non-irradiated cells by using the NRU test to classify the phototoxic substance when the difference (PIF, photoirritation factor) becomes 5 times or more.
  • Table 5 shows the phototoxicity results of PE and P7 extracts prepared from laver by the 3T3 NRU phototoxicity assay.
  • P7 a purified extract
  • IC 50 the amount by which a certain amount of a substance that is expected to be toxic to animals is used in the experiment. It was determined as a non-phototoxic substance with a PIF value of 1 exceeding 1000 mg / ml regardless of whether or not.
  • the mean half lethal concentration was lower than that of P7, and the degree of toxicity was relatively high.
  • Figure 2 is a graph showing the phototoxicity results of the non-toxic UV protection crude extract (PE) and secondary purified extract (P7) extracted from seaweed according to the photohemolysis test using human red blood cells.
  • Figure 3 is a photograph showing the phototoxicity results according to the photohemolysis test using human erythrocytes when the concentration of non-toxic UV protection crude extract (PE) extracted from seaweed is 500 ⁇ g / ml
  • Figure 4 It is a photograph showing the phototoxicity results according to the photohemolysis test using human erythrocytes when the concentration of the non-toxic UV blocking secondary tablet extract (P7) extracted from the 250 ⁇ g / ml.
  • UV- represents a state not irradiated with ultraviolet rays
  • UV + represents a state irradiated with ultraviolet rays.
  • the ultraviolet dose used in the photohemolysis test shown in FIGS. 2 to 4 was UVA 15J / cm 2.
  • the phototoxicity result by the photohemolysis test using human erythrocytes was almost the same as the phototoxicity test result by the 3T3 NRU phototoxicity test.
  • Cytotoxicity test was performed on HaCaT, a human keratinocyte, against PE and P7 extracts prepared from seaweed. The cytotoxicity was evaluated using the Neutral red assay.
  • Table 6 shows the results of cytotoxicity test on HaCaT, human keratinocytes of PE and P7, which are extracts prepared from 3 ginseng.
  • both the half lethal concentrations of HaCaT of PE and P7 were more than 5 mg / ml, which is considered to be a non-cytotoxic substance.
  • both the crude extract and the purified extract prepared from laver were found to be non-toxic sunscreen extracts, and the extract may be used as a main component of a cosmetic composition such as a sunscreen.
  • the cosmetic composition may be prepared in the form of cream, lotion, gel, tonic or mist, the content of the sunscreen injection may be appropriately selected in the range that does not cause toxicity to the skin.
  • the extract of laver or jindubal prepared by the method of the present invention can be used as an active ingredient of sunscreen cosmetics.

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PCT/KR2010/006099 2010-02-08 2010-09-08 홍조류로부터 비독성 자외선 차단용 추출물을 제조하는 방법 및 이를 이용한 비독성 자외선 차단제 WO2011096628A1 (ko)

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CN201080063299.5A CN102740869B (zh) 2010-02-08 2010-09-08 由红藻类制备无毒性紫外线屏蔽用提取物的方法及利用该方法的无毒性紫外线屏蔽剂
JP2012551898A JP2013518871A (ja) 2010-02-08 2010-09-08 紅そう類から非毒性紫外線遮断用抽出物を製造する方法及びこれを用いた非毒性紫外線遮断剤

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Cited By (3)

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KR20170002587A (ko) * 2014-05-13 2017-01-06 각코우호우징 기타사토켄큐쇼 미생물을 사용한 미코스포린 유사 아미노산을 생산하는 방법
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