WO2012011214A1 - Procédé pour obtenir un sphingolipide et sphingolipide - Google Patents

Procédé pour obtenir un sphingolipide et sphingolipide Download PDF

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WO2012011214A1
WO2012011214A1 PCT/JP2011/002256 JP2011002256W WO2012011214A1 WO 2012011214 A1 WO2012011214 A1 WO 2012011214A1 JP 2011002256 W JP2011002256 W JP 2011002256W WO 2012011214 A1 WO2012011214 A1 WO 2012011214A1
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sphingolipid
ceramide
free
solvent
free ceramide
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PCT/JP2011/002256
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English (en)
Japanese (ja)
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恵太 柚木
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宮鍋 征克
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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

Definitions

  • the present invention relates to a method for obtaining a sphingolipid having a high content of free ceramide and a sphingolipid having a high content of free ceramide, which can be directly used for cosmetics and health foods. More specifically, it can be separated into glucosylceramide and free ceramide by purification, the former can be used for food and the latter can be used for cosmetics, and the content of free ceramide that is extremely rare in nature and human type
  • the present invention relates to a sphingolipid having a large amount and a method for obtaining the same.
  • Patent Document 1 Japanese Patent No. 4071062 in which attention is paid to a functional component in a fermenter and the component is utilized.
  • the invention described in Patent Document 1 relates to a composition for preventing or treating a tumor that is malignant melanoma.
  • the composition for the prevention or treatment of tumors that are malignant melanomas is obtained by drying a solid ethanol extract residue obtained by drying a liquid separated from a shochu distiller or a liquid separated from a shochu distiller. It contains an ethanol extract of the obtained solid content.
  • Patent Document 2 JP 2007-82427 A (Patent Document 2) clearly shows that glycosylceramide was obtained by extraction from beer koji.
  • the glycosylceramide is effective as a component of health foods and moisturizers.
  • JP 2000-80394 A discloses a method for producing sphingolipids in which a sphingolipid is extracted from soy sauce cake with an organic solvent, and the obtained sphingolipid is used as a raw material for cosmetics. it has been shown that that.
  • the sphingolipid has a common structure of a ceramide in which a long-chain fatty acid is an acid amide bond to a sphingoid base, which is a long-chain base, and a glycosphingolipid containing a glycosylceramide in which a sugar is glycosidically bonded to a phosphate and a base.
  • Patent Document 4 shows that a glycosphingolipid having a specific structure extracted from a sponge is effective as an antitumor agent or an immunostimulator.
  • Patent Document 5 JP 2004-131481 discloses that a glycosylceramide having a specific structure or a salt thereof is an NKT cell activator, an autoimmune disease (for example, systemic lupus erythematosus, systemic scleroderma, ulcer E. coli, encephalomyelitis, multiple sclerosis, human type I diabetes, etc.) and a fertility agent.
  • an autoimmune disease for example, systemic lupus erythematosus, systemic scleroderma, ulcer E. coli, encephalomyelitis, multiple sclerosis, human type I diabetes, etc.
  • a fertility agent for example, systemic lupus erythematosus, systemic scleroderma, ulcer E. coli, encephalomyelitis, multiple sclerosis, human type I diabetes, etc.
  • this sphingolipid acts as a moisturizing component that prevents water evaporation from the stratum corneum of the skin.
  • This keratin ceramide is produced by the degradation of glucosylceramide and sphingomyelin by the action of glucocerebrositase and sphingomyelinase in epidermal cells.
  • the amount of production decreases with age, and as skin dryness and wrinkles progress with age and atopic dermatitis is the cause, it prevents the reduction of sphingolipids in the skin. Therefore, as disclosed in Patent Document 3, it is blended in creams and ointments and used as a skin moisturizer.
  • shochu distilled spirit contains various components such as fiber derived from cereals, protein, ash, fat, partially unfermented sugar, fermenting microorganisms, organic acids and vitamins. Is disclosed. Further, a composition for preventing or treating a tumor which is a malignant melanoma, containing a liquid ethanol residue or an ethanol extract separated from the shochu distilled spirit is disclosed. However, there is no disclosure as to whether or not other components are contained in the shochu distiller and what effect the other components have.
  • Patent Document 2 a method for efficiently producing a plant ceramide-related substance from beer koji obtained in a production process such as beer, and a plant ceramide-related substance (ceramide, cerebroside) obtained by the method are disclosed. It is disclosed with respect to the product it contains. However, there is no disclosure about what other substances the plant ceramide-related substance obtained from beer koji contains.
  • Patent Document 3 discloses that sphingolipids conventionally extracted from nerve tissues such as bovine brain are extracted from soy sauce or soy sauce cake, which is a by-product of soy sauce, with an organic solvent such as hexane. However, there is no disclosure about what other substances the sphingolipid contains and how they act.
  • Patent Document 4 discloses that the glycosphingolipid is extracted from sponges
  • Patent Document 5 merely discloses that glycosylceramide is effective as a specific therapeutic agent and fertility agent.
  • the inventor produced by-products in the production of sake, shochu, soy sauce, beer, etc., and fermented rice that has been variously studied for its treatment, contains sphingolipids as functional components, Analyzing and identifying sphingolipids as functional components in the fermented rice cake that requires koji and yeast based on the fact that sphingolipids can be widely applied to various products, medicines, health foods and cosmetics.
  • the research was conducted based on the prediction that the fermented koji could be used more effectively.
  • a large amount of sphingolipids and free ceramide are included.
  • the content of free ceramide in the sphingolipid can be increased by a simple operation of multiple extractions and purifications.
  • the invention according to claim 1 of the present invention is When extracting sphingolipids using alcohol from the fermented rice cake, Add a solvent that does not dissolve the free ceramide to the resulting alcohol extract, A method for obtaining a sphingolipid, comprising obtaining a sphingolipid having an increased content of free ceramide by removing a component dissolved in the solvent.
  • the invention according to claim 2 of the present invention is Extract sphingolipids from the fermented rice using alcohol, Add a solvent that does not dissolve free ceramide to the sphingolipid obtained, The sphingolipid is obtained by removing the component dissolved in the solvent and extracting the sphingolipid again with alcohol.
  • the invention according to claim 3 of the present invention is The method for obtaining a sphingolipid according to claim 1 or 2,
  • the solvent that does not dissolve the free ceramide is It is characterized by being hexane and / or acetone.
  • the invention according to claim 4 of the present invention is The method for obtaining a sphingolipid according to claim 1 or 2,
  • the free ceramide is It contains human-type or human-type-like free ceramide.
  • the invention according to claim 5 of the present invention is Add a solvent that does not dissolve free ceramide to the alcoholic extract of fermented rice,
  • the sphingolipid is characterized in that the component dissolved in the solvent is removed to make the content of free ceramide 5% or more.
  • a solvent that does not dissolve free ceramide is added to the obtained alcohol extract and dissolved in this solvent.
  • the sphingolipid acquisition method of the present invention can be acquired using only food additives, it can be used as a method for acquiring raw materials for which toxicity is a concern, including for skin application. Is particularly effective.
  • human-type or human-type-like free ceramide is mainly used, and a large amount of sphingolipid having a high content of free ceramide that can be easily used as a raw material for foods and health foods can be obtained.
  • the free ceramide obtained in the present invention is J.I. A. It has the same structure or an approximate structure as nine types of human ceramides (ceramide 1 to ceramide 9) introduced by Boustra et al. Together with the skin protecting function. These human-type ceramides, ceramide 1 to ceramide 9, do not include the L-isomer, which is an optical isomer, and the cis isomer, which is a geometric isomer, and are said to have the following characteristics, respectively. (Biochimica et Biophysica Acta 1758 (2006) 2080-2095). Therefore, the free ceramide obtained in the present invention is also considered to have equivalent performance.
  • Ceramide 1 is said to strengthen the binding of intercellular lipids in multi-layered bilayers and is related to keratosis, ichthyosis, and atopic dermatitis due to lack. In addition, it is said to have an effect of improving the elasticity of the skin and the connectivity between cells, and is suitable for aging skin and dry skin.
  • Ceramide 2 has the same structure as ceramide present in skin and hair, and is a white to gray powder with a specific odor. Among the ceramides, ceramide 2 plays a role of water retention, and is suitable for high moisture retention and rough skin countermeasures. Yes.
  • Ceramide 3 (stearic acid binding type) is a white to light yellow powder with the same structure as ceramide present in the skin and has a specific odor, recovers the barrier function, and maintains the water retention function for a long time. . Also used to improve damaged hair.
  • Ceramide 3 (oleic acid binding type) has the same structure as ceramide present in the skin and has the same effect as N-stearoyl phytosphingosine, but it is easy to formulate and has high solubility in oil. If the concentration is up to about 0.5%, a transparent preparation can be made, and since the protective effect is high, it is suitable for sensitive skin and dry skin.
  • Ceramide 4 Ceramide 5 and Ceramide 6 promote the exfoliation action and smooth the skin.
  • free ceramide which is extremely rare in nature
  • sphingolipid with a high content of human-type free ceramide at least 5%, more than 30%, particularly more than 50% or more than 90%.
  • Sphingolipids containing free ceramides are obtained.
  • the obtained sphingolipid is used as a raw material for cosmetics or skin external preparations according to the above features and exhibits an excellent function, and is effectively used as a raw material component thereof.
  • the sphingolipid of this invention contains human-type free ceramide. Therefore, even if it is used as it is for cosmetics and health foods, it is expected to exhibit excellent functions, and the glucosyl type and free type are separated and the former is used for food and the latter is used for cosmetics. It is also possible, and it is an excellent one with a wide variety of usage methods.
  • FIG. 1 is a diagram showing the results of silicic acid TLC analysis of soy sauce lees total lipids.
  • FIG. 2 is a diagram showing the results of HPLC analysis of soy sauce koji polar lipids and soybean alkali-stable lipid, wherein A shows the soy sauce koji analysis results and B shows the soy sauce analysis results.
  • FIG. 3 is a diagram showing the structure of ceramide in shochu shochu, soy sauce koji, sake lees koji, and black vinegar moromi koji.
  • FIG. 4 is a diagram showing the results of silicic acid TLC analysis of the soy sauce cake extract and purified product.
  • FIG. 5 is a comparative diagram showing the results of TLC analysis of silicic acid for comparison between a soy sauce koji extract and a refined sake koji extract.
  • FIG. 6 shows the structure of the main ceramide present in soy sauce cake.
  • a soy sauce koji is preferable as a fermented koji used for extraction of sphingolipids.
  • other fermented rice cakes that is, vinegar rice cake, miso, awamori rice cake, etc. are extracted from shochu, oil refined rice cake, black vinegar rice cake, etc. Applicable to the invention.
  • foreign liquors Shaoxing liquor, Makgeolli, etc.
  • Extraction of sphingolipids from the fermented rice cake may be performed using alcohol, particularly ethanol.
  • a solvent for removing impurities other than free ceramide in the sphingolipid in other words, a solvent that does not dissolve free ceramide in order to obtain a sphingolipid with a high content of free ceramide, that is, a non-solvent of free ceramide. If it exists, various things are used.
  • Preferable solvents include hexane and / or acetone.
  • there are no special conditions for sphingolipid extraction separation, purification, identification, etc., and normal operations are widely applied.
  • the fermented rice cake used is a fermented rice cake made of soy sauce made from soybeans, and a fermented rice cake made of soy sauce made from yellow potato cake and purple potato cake.
  • FIG. 1 shows the result of analyzing the total lipid by silicic acid thin layer chromatography (TLC, 0.25 mm, manufactured by Merck & Co., Inc.).
  • the developing solvent was chloroform / methanol: water (90: 10: 1), and detection was performed by heating after spraying with 50% sulfuric acid.
  • this lipid contains a large amount of free fatty acids that are degradation products of lipids.
  • the polar lipid fraction was magnified with a dotted line, a spot of free ceramide, which is a lipid hardly present in soybean, was detected in addition to sterol glycoside and glucosylceramide, which are abundant in soybean.
  • silicic acid column chromatography of the total lipid was performed and fractionated into neutral lipid (NL) and polar lipid fraction (PL). That is, 100 mg of total lipids were dried and dissolved in a small amount of chloroform, and then subjected to a Sep-Pak silica cartridge (manufactured by Waters). First, neutral lipid was eluted with 50 mL of chloroform, and then polar lipid was eluted with 30 mL of methanol. When both fractions were concentrated and dried with a rotary evaporator and weighed, it was found that the total lipid contained 89.5% of the neutral lipid fraction and 10.5% of the polar lipid fraction.
  • the polar lipid fraction was subjected to HPLC analysis, and sphingolipid was quantified. Separation was performed by two-liquid gradient elution, and detection was performed using an evaporative light scattering detector (ELSD, manufactured by Shimadzu Corporation).
  • ELSD evaporative light scattering detector
  • Soybean analysis was performed on an alkali-stable lipid fraction obtained by alkaline decomposition of total lipid prepared in the same manner as described above with 0.4 M ethanolic KOH.
  • soy sauce cake has a large peak around 4 minutes, which is not present in the original soybean.
  • the amounts of free ceramide and glucosylceramide determined from the standard curve of standard ceramide and standard glucosyl ceramide were 380 mg and 80 mg per 100 g of dry weight, respectively. In the ratio, the free ceramide was 82.6%.
  • ⁇ Sphingolipid analysis of Satsuma shochu> In the same manner as in Example 1, the lipid analysis of shochu was performed using yellow candy and purple candy.
  • the raw material used was a solid part obtained by separating the shochu waste liquid with a solid-liquid separator (hereinafter referred to as yellow jade and purple koji).
  • the lipid content of jaundice (62% moisture) and purple koji (69% moisture) were 2.0 and 1.8 g / 100 g (per fresh weight), respectively.
  • FIG. 3 shows the data of sake mash and black vinegar moromi mash separately prepared and measured by the inventors, and other plants shown by Takakuwa et al. (Bioresource Technology, 96, 1089-92, 2005). The analytical values of were displayed together.
  • soy sauce cake and shochu contain a large amount of a functional material glucosylceramide (commonly known as plant ceramide) that is already widely recognized in the market.
  • glucosylceramide commonly known as plant ceramide
  • FIG. 3 measured the amount of glucosylceramide in various vegetable foods and residues, and reported that it was slightly more in apple pulp.
  • the amount of glucosylceramide in shochu as measured by the inventor is much higher than these, and soy sauce cake is equivalent to apple pulp but superior to others.
  • a large amount of free ceramide which is hardly contained in raw material soybeans, Satsuma koji, and other natural products, was contained in these fermented koji.
  • Free ceramide and glucosylceramide obtained from soy sauce cake were separated by silicic acid TLC under the same conditions as described above, and 1 mg each was reacted in 1 ml of 1M methanolic HCL at a temperature of 70 ° C. for 18 hours. After the reaction, 2 ml of hexane was added, and the extraction by stirring was repeated three times to extract the fatty acid. The lower layer (methanol layer) was adjusted to ph10 with 4M KOH, 1 mL of water was added, and the mixture was extracted 3 times with 2 mL of diethyl ether.
  • the collected diethyl ether layer was washed with distilled water three times, and then the organic layer was dried with nitrogen gas to obtain a sphingoid base fraction.
  • the result of TLC analysis of the obtained sphingoid base fraction is shown in FIG. 4, and a comparison with sake lees is shown in FIG.
  • the sphingoid base fraction was subjected to GC-MS analysis (QP2010, Shimadzu Corporation) as a trimethylsilyl derivative.
  • the fatty acids of glucosylceramide were all ⁇ -hydroxy fatty acids. 16h: 0, 22h: 0, and 24h: 0 characteristic of soybean were detected. Further, 20h: 0 characteristic of wheat and 18h: 0 and 18h: 1 characteristic of koji mold were detected, respectively. Furthermore, it can be seen that the soy sauce cake contains glucosylceramide specific to the raw material. In the notation such as 16h: 0, numbers such as “16” indicate the number of carbon atoms, h indicates an ⁇ -hydroxyl group, and the last number (such as 0) indicates the number of double bonds.
  • sphingoid bases 9-methyl sphingadienin (d19: 2), which is present only in fungi such as Neisseria gonorrhoeae and yeast, was detected.
  • the “d” is an abbreviation for dihydroxy base.
  • the constituent fatty acid of the free ceramide was 85% ⁇ -hydroxy fatty acid and the remaining 15% non-hydroxy fatty acid.
  • hydroxy fatty acids a lot of very long chain fatty acids such as 24 and 22 were detected.
  • 2,3 dihydroxy fatty acid (24h2: 0) was also detected, which is considered to be derived from Neisseria gonorrhoeae.
  • FIG. 6 the main structure of ceramide contained in soy sauce cake is summarized in FIG.
  • the X type is not included in the previous nine types, but was known as a part of the plant and fungal ceramide composition, and was the first to succeed in obtaining a free form. is there.
  • Ceramide X has many hydroxyl groups and is expected as a new material having a high moisturizing effect.
  • the free ceramide of the present invention is almost trans form unlike other natural ceramides containing cis isomers. , Human-type ceramide, or ceramide similar to it.
  • soy sauce cake contains four types of free ceramide and three types of glucosylceramide as main components. did.
  • soy sauce cake contains a lot of ceramides 6 and 7, and sake sake cake contains a lot of ceramide 3, and the human-type free ceramide obtained from each of them is judged to have a unique performance. Is.
  • Ethanol 500 mL was added to the precipitate, and stirring and centrifugation at a temperature of 40 ° C. for 15 minutes were repeated three times.
  • the ethanol solution was decolorized using activated carbon and then an anion exchange resin, and concentrated to dryness. Furthermore, it melt
  • the precipitate was treated in the same manner by adding 50 mL of hexane and 50 mL of acetone, and the precipitate was dried in a vacuum desiccator for 2 hours to obtain 4.3 g of ceramide powder (including glucosyl type).
  • the sphingolipid of the present invention contains a large amount of free ceramide which is rare in nature, particularly human-type free ceramide.
  • it since it is obtained in large quantities from fermented rice cake, it has been widely used in the industries that handle it as a raw material for health foods, cosmetics, or external preparations for skin. There is a possibility that
  • it since it is obtained in large quantities from fermented fermented products, it has been recognized that it has been toxic from natural products in place of chemical synthetic products that have been used as raw materials for health foods, cosmetics, or external preparations for skin. As a safe new material that has no effect, it has the potential to be widely used in industries dealing with health foods, cosmetics, and skin preparations.

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Abstract

La présente invention concerne un moyen permettant d'utiliser efficacement un résidu de fermentation (gâteau), à savoir un procédé qui consiste à éliminer les impuretés d'un extrait alcoolique d'un gâteau à l'aide d'un non solvant pour céramides libres, tel que l'hexane ou l'acétone, et ensuite à extraire le résidu avec un alcool à nouveau. L'invention concerne également un procédé permettant d'obtenir un sphingolipide contenant des céramides libres notamment, par exemple, des céramides libres de type humain, qui sont extrêmement rares dans la nature, et présentant une teneur élevée en céramides libres supérieure ou égale à 3 %, et même supérieure ou égale à 90 % dans certains cas, et le sphingolipide ainsi obtenu.
PCT/JP2011/002256 2010-07-23 2011-04-18 Procédé pour obtenir un sphingolipide et sphingolipide WO2012011214A1 (fr)

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JP2017137439A (ja) * 2016-02-04 2017-08-10 株式会社双葉紙器 セラミドとセラミド誘導体との製造方法
JP2020097539A (ja) * 2018-12-18 2020-06-25 株式会社ジェヌインＲ＆Ｄ セラミド分散組成物

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JP6619548B2 (ja) * 2014-06-09 2019-12-11 共栄化学工業株式会社 化粧料
JP6860209B2 (ja) * 2017-12-27 2021-04-14 株式会社 サティス製薬 セラミドｎｐの製造方法
JP6651201B2 (ja) * 2018-01-30 2020-02-19 学校法人金沢工業大学 レジスタントプロテイン含有物の製造方法
JP2021013355A (ja) * 2019-07-16 2021-02-12 株式会社ファーメンステーション 化粧品原料、食品原料又はサプリメント原料を製造する方法、及び該方法により製造された化粧品原料、食品原料又はサプリメント原料
WO2023063424A1 (fr) * 2021-10-15 2023-04-20 株式会社ファーマフーズ Composition contenant un céramide et son procédé de production

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JP2005120321A (ja) * 2003-10-20 2005-05-12 Nippon Beet Sugar Mfg Co Ltd スフィンゴ糖脂質の製造方法
JP2005263793A (ja) * 2004-02-18 2005-09-29 Rohto Pharmaceut Co Ltd 皮膚外用剤

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JP2015027985A (ja) * 2013-06-25 2015-02-12 株式会社東洋新薬 美容組成物
JP2017137439A (ja) * 2016-02-04 2017-08-10 株式会社双葉紙器 セラミドとセラミド誘導体との製造方法
JP2020097539A (ja) * 2018-12-18 2020-06-25 株式会社ジェヌインＲ＆Ｄ セラミド分散組成物

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