WO2023063424A1 - Composition contenant un céramide et son procédé de production - Google Patents

Composition contenant un céramide et son procédé de production Download PDF

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WO2023063424A1
WO2023063424A1 PCT/JP2022/038436 JP2022038436W WO2023063424A1 WO 2023063424 A1 WO2023063424 A1 WO 2023063424A1 JP 2022038436 W JP2022038436 W JP 2022038436W WO 2023063424 A1 WO2023063424 A1 WO 2023063424A1
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ceramide
composition
wine
composition according
containing composition
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PCT/JP2022/038436
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English (en)
Japanese (ja)
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有宏 金
裕晃 山田
アンガ サンジャヤ，
英一 金
敦史 山津
武祚 金
Original Assignee
株式会社ファーマフーズ
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Publication of WO2023063424A1 publication Critical patent/WO2023063424A1/fr

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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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/164—Amides, e.g. hydroxamic acids of a carboxylic acid with an aminoalcohol, e.g. ceramides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • 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
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • 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
    • A61K8/42—Amides
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations

Definitions

  • the present invention relates to compositions containing ceramide. More specifically, it relates to compositions containing polyphenols and ceramides, especially free ceramides, and methods of making the same.
  • Ceramide is a type of sphingolipid and a major component of stratum corneum intercellular lipids. Ceramide is expected to have effects such as skin barrier effect (surface protection), moisturizing effect, moisture regulation, elasticity retention, collagen protection, and antioxidant effect when applied to the skin or taken orally. Many cosmetic products and functional foods are provided.
  • ceramides plant-derived ceramide raw materials have been put into practical use from many plants such as konnyaku and rice, and all of them contain glucosylceramide (sugar ceramide) as the main component and are mainly used as raw materials for food.
  • these glucosylceramides are non-human ceramides and differ in structure from human ceramides.
  • human ceramide is in a free form (free ceramide) in which sugars and phosphoric acids are not bound, and is not contained in normal living cells, so it is a component that hardly exists in the natural world. Therefore, the development of free ceramides derived from natural products is desired.
  • the present inventors have found a novel composition useful for health and/or beauty, containing polyphenols and ceramide (especially free ceramide).
  • the present inventors also found that a composition containing ceramide (particularly, free ceramide) in addition to polyphenols can be obtained by subjecting fermented lees produced during wine brewing to a specific treatment. rice field. Therefore, the present invention provides a composition derived from a natural product containing such polyphenols and ceramides, and a method for producing the same.
  • (Item 1) A cosmetic and/or oral composition containing polyphenols and ceramides.
  • (Item 2) The composition according to the preceding items, wherein the ceramide comprises free ceramide and glucosylceramide.
  • (Item 3) A composition according to any one of the preceding items, wherein the composition comprises at least about 1% by weight of free ceramide.
  • (Item 4) A composition according to any one of the preceding items, wherein said composition comprises at least about 1% by weight of glucosylceramide.
  • (Item 5) A composition according to any one of the preceding items, wherein the composition comprises at least about 1% by weight of polyphenols.
  • (Item 10) The composition according to any one of the above items, which is for food.
  • (Item 11) The composition according to any one of the above items, which is used for cosmetics.
  • (Item 12) The composition according to any one of the above items, wherein the polyphenol and the ceramide are derived from wine fermentation lees.
  • (Item 13) A composition according to any one of the preceding items for promoting keratinocyte differentiation.
  • (Item 14) A composition according to any one of the preceding items for promoting ceramide synthesis.
  • (Item A1) A ceramide-containing composition derived from wine fermentation lees.
  • (Item A2) A composition according to any one of the preceding items, wherein the ceramide-containing composition comprises at least about 1% by weight of free ceramide.
  • compositions according to any one of the preceding items, wherein the ceramide-containing composition comprises at least about 1% by weight of glucosylceramide.
  • compositions according to any one of the preceding items, wherein the ceramide-containing composition comprises at least about 1% by weight of polyphenols.
  • the weight ratio of free ceramide, glucosylceramide, and polyphenol in the composition is about 0.7 to about 2.4: about 1.0: about 1.4 to about 11.0. 13.
  • composition according to any one of the preceding items wherein the weight ratio of free ceramide, glucosylceramide and polyphenol in the ceramide-containing composition is about 1.0: about 1.0: about 1.0.
  • composition according to any one of the preceding items wherein the ceramide-containing composition has a pH of less than about 5.
  • composition according to any one of the preceding items comprising at least about 10 mg resveratrol per about 100 g.
  • the composition according to any one of the above items, which is for food. (Item A10) The composition according to any one of the above items, which is used for cosmetics.
  • (Item A11) A composition according to any one of the preceding items for promoting keratinocyte differentiation.
  • (Item A12) A composition according to any one of the preceding items for promoting ceramide synthesis.
  • (Item B1) A method for producing a ceramide-containing composition, comprising: A step of washing the wine fermented lees; and extracting the residue obtained by said washing with a polar solvent.
  • the method according to the preceding items, wherein the polar solvent comprises ethanol.
  • (Item B3) A method according to any one of the preceding items, wherein the ethanol concentration is about 95%.
  • (Item B4) A method according to any one of the preceding items, wherein the washing step is performed with water.
  • (Item B5) A method according to any one of the preceding items, further comprising the step of pH-adjusting the extract obtained by the step of extracting.
  • (Item B6) A method according to any one of the preceding items, wherein said pH adjustment is performed with tartaric acid or citric acid.
  • (Item C1) A method for promoting keratinocyte differentiation, comprising administering a composition according to any one of the preceding items.
  • (Item C2) A method for promoting ceramide synthesis, comprising administering a composition according to any one of the preceding items.
  • a composition containing polyphenols and ceramides, especially human-type free ceramides can be obtained.
  • a composition containing polyphenols and ceramides, especially human-type free ceramides, can be obtained.
  • fermented wine lees when such a composition is obtained from fermented wine lees, it uses fermented wine lees, which is a highly safe natural material. It has excellent safety and high utility value without adversely affecting the environment.
  • FIG. 1 is a graph according to an embodiment showing the difference between the composition of ceramide molecular species in wine starch and the composition of ceramide molecular species in soybean.
  • FIG. 2 is a graph according to one embodiment showing the difference between the amount of ceramide obtained from wine lees extract and the amount of ceramide obtained from wine.
  • FIG. 3 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. The left side of FIG. 3 shows the case where the ceramide extract was extracted from the starting wine lees with 95% ethanol, and the right side of FIG. 3 shows the case where the starting wine lees were washed with 50% ethanol.
  • FIG. 3 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. The left side of FIG. 3 shows the case where the ceramide extract
  • FIG. 4 is a graph according to one embodiment showing differences in composition of ceramide-containing compositions due to differences in washing processes.
  • FIG. 4 shows the content (mg) of each component.
  • FIG. 5 shows the difference in the composition of the ceramide-containing composition due to the difference in the washing process (when the ceramide extract is extracted from the raw wine lees with 95% ethanol and when the raw wine lees are washed with 50% ethanol).
  • 4 is a graph according to one embodiment;
  • FIG. 5 shows the ratio of each component.
  • FIG. 6 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition.
  • FIG. 7 is a graph according to an embodiment showing the difference in the composition of the ceramide-containing composition due to the difference in the washing process (when the raw wine starch was washed with water, 10%, 30%, or 50% ethanol). .
  • the left side of FIG. 7 shows the ratio of each component, and the right side of FIG. 7 shows the content (mg) of each component.
  • FIG. 8 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. It shows the case where the raw wine lees are washed with water at 40°C or 60°C.
  • FIG. 8 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. It shows the case where the raw wine lees are washed with water at 40°C or 60°C.
  • FIG. 9 is a graph according to one embodiment showing the difference in the composition of the ceramide-containing composition due to the difference in the washing process (when the raw wine starch is washed with water at 40° C. or 60° C.).
  • the left side of FIG. 9 shows the ratio of each component, and the right side of FIG. 9 shows the content (mg) of each component.
  • FIG. 10 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. Raw wine lees are shown washed with water for 30, 60, or 180 minutes.
  • FIG. 10 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. Raw wine lees are shown washed with water for 30, 60, or 180 minutes.
  • FIG. 11 is a graph according to one embodiment showing the difference in the composition of the ceramide-containing composition due to the difference in the washing process (when the raw wine lees are washed with water for 30, 60, or 180 minutes).
  • the left side of FIG. 11 shows the ratio of each component, and the right side of FIG. 11 shows the content (mg) of each component.
  • FIG. 12 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. It shows the case where the raw material wine sediment was washed with 10 times, 8.3 times, and 6.7 times the amount of water.
  • FIG. 12 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine the washing step in the process for producing a ceramide-containing composition. It shows the case where the raw material wine sediment was washed with 10 times, 8.3 times, and 6.7 times the amount of water.
  • FIG. 13 shows the difference in the composition of the ceramide-containing composition due to the difference in the washing process (when the raw wine starch was washed with 10 times, 8.3 times, and 6.7 times the amount of water) according to one embodiment.
  • the left side of FIG. 11 shows the ratio of each component, and the right side of FIG. 11 shows the content (mg) of each component.
  • FIG. 14 is a schematic diagram showing a process flow for producing a ceramide-containing composition, which was used to examine pH adjustment in the process for producing a ceramide-containing composition. It shows the case where tartaric acid, citric acid, or sodium carbonate is added to the ceramide extract extracted from the raw wine lees.
  • FIG. 15 is a photograph according to one embodiment showing the difference in color of the ceramide-containing composition due to the difference in pH.
  • FIG. 16 is a graph according to one embodiment showing the effect of a ceramide-containing composition on human epidermal cell proliferation.
  • human epidermal cells Hacat cells
  • FIG. 17 is a graph according to one embodiment showing the amount of resveratrol contained in red wine, wine lees (wine crystals), and ceramide-containing composition (wine ceramide).
  • FIG. 18 is a graph showing mRNA expression levels of differentiation markers (Pro-Filaggrin and Loricrin) when wine ceramide according to one embodiment of the present invention was added to a human epidermal keratinocyte Hacat cell line and cultured for 72 hours.
  • FIG. 19 is a graph showing the mRNA expression level of ceramide synthesis pathway marker (SPT: Serine-Palmitoyl Transferase) when wine ceramide according to one embodiment of the present invention was added to human epidermal keratinocyte Hacat cell line and cultured for 72 hours. is.
  • SPT Serine-Palmitoyl Transferase
  • FIG. 20 shows a differentiation marker (Pro-Filaggrin) and ceramide synthesis pathway when wine ceramide, glucosylceramide, and free ceramide according to one embodiment of the present invention were added to human epidermal keratinocyte Hacat cell line and cultured for 72 hours. It is a graph which shows the mRNA expression level of a marker (SPT).
  • FIG. 21 shows that wine ceramide according to one embodiment of the present invention and ceramides obtained from raw materials other than wine (rice ceramide, pine ceramide, and konjac ceramide) were added to human epidermal keratinocyte Hacat cell line, and 72 hours.
  • FIG. 1 is a graph showing mRNA expression levels of a differentiation marker (Pro-Filaggrin) and a ceramide synthesis pathway marker (SPT) when cultured.
  • FIG. 1 is a graph showing mRNA expression levels of a differentiation marker (Pro-Filaggrin) and a ceramide synthesis pathway marker (SPT) when cultured.
  • FIG. 22 is a photograph of a cell section when wine ceramide according to one embodiment of the present invention was added to 3D-cultured keratinocytes and
  • FIG. 23 is a photograph of a cell section when wine ceramide according to one embodiment of the present invention was added to 3D-cultured keratinocytes and cultured for 48 hours.
  • the amount of ceramide in the cell section was immunostained with an anti-ceramide antibody and observed under a phase-contrast microscope.
  • Wine ceramide according to one embodiment of the present invention significantly increased the amount of ceramide in the skin.
  • Ceramide is a kind of sphingolipid and refers to a group of compounds in which sphingosine and fatty acid are amide bonded.
  • Ceramide also includes ceramide derivatives. Ceramide is a compound having a structure (--NH--CO--) in which an amino group (--NH 2 ) of a sphingoid base is bonded to a carboxyl group (--COOH) of a fatty acid. The alcoholic hydroxyl group (--OH) of the sphingoid base of ceramide is further combined with a polar group such as sugar and phosphoric acid to form glycosphingolipids and phosphosphingolipids, respectively.
  • a polar group such as sugar and phosphoric acid
  • those bound with sugars are particularly called glycosylceramides, and particularly when the sugar is glucose, they are called glucosylceramides.
  • Ceramide is called free ceramide when sugar, phosphoric acid, etc. are not bound to ceramide. Since free ceramide is generally an intermediate metabolite in the sphingolipid synthesis system, it exists only in minute amounts, especially in animals and plants.
  • Galactosylceramide, glucosylceramide, and sphingomyelin, in which ceramide is bound with sugar or phosphoric acid, are extracted from animals and plants, but because the sugar or phosphoric acid is bound, they are not found in intercellular lipids. orientation is different from that of free ceramide.
  • polyphenol is a general term for compounds having multiple phenolic hydroxyl groups in the molecule, specifically flavonols, flavones, isoflavones, tannins, catechins, quercetin, anthocyanins, anthocyanidins, leucoanthocyanidins. , proanthocyanidins, propyl gallate, catechin, rutin, quercetin, ferulic acid, resveratrol, procyanidins, theaflavin, curcumin, pycnogenol, rosmarinic acid, ellagic acid, quinic acid, chlorogenic acid, hydroxytyrosol and the like.
  • washing refers to washing away and removing impurities by stirring and mixing wine fermented lees (wine lees) and liquid.
  • extraction means separating the analyte contained in the solution from other impurities, and is also referred to as solvent extraction or liquid-liquid extraction.
  • a cosmetic and/or oral composition containing polyphenols and ceramides is provided.
  • a ceramide-containing composition derived from wine fermentation lees is provided. Since both the cosmetic and/or oral intake composition containing polyphenol and ceramide and the ceramide-containing composition derived from fermented wine lees contain ceramide, they are not particularly mentioned in the present specification. Except for this, it can be collectively referred to as a "ceramide-containing composition". Moreover, in this specification, the ceramide-containing composition of the present invention may be referred to as "wine ceramide".
  • Ceramide is a type of sphingolipid and includes a group of compounds in which sphingosine and fatty acid are amide bonded.
  • ceramide is a non-permeable compound having one or more long-chain straight and/or branched alkyl or alkenyl groups, at least two hydroxyl groups, and one or more amide groups (and/or amino groups) in the molecule. It may be an ionic amphiphilic substance. Ceramide may also be a substance in which a phosphatidylcholine residue or a sugar residue is bound to the hydroxyl group of the nonionic amphiphilic substance (a type of so-called ceramide derivative).
  • ceramides include free ceramides and glucosylceramides.
  • ceramides include plant-derived ceramides, preferably wine fermentation lees-derived ceramides.
  • the free ceramide is not particularly limited as long as it can be used for cosmetics, external skin preparations, or food. 6I, and natural free ceramides such as ceramide 6II.
  • the ceramide-containing composition of the present invention can be obtained using materials that do not adversely affect the human body, so safety is important for food and skin applications. It is effective as a raw material for the intended use. In addition, since it contains human-type free ceramide, it is also suitable as a raw material for foods such as health foods.
  • the ceramide-containing composition of the present invention can contain only one type of these free ceramides or a combination of two or more types in any mixing ratio.
  • the ceramide in the ceramide-containing composition of the present invention has a barrier function that prevents moisture from evaporating from the skin, a function that restores the barrier function, a function that imparts firmness and elasticity to the hair, a function that promotes exfoliation of keratin, a function that smoothes the skin, and a skin
  • the ceramide-containing composition of the present invention has various functions such as a function of exerting a moisturizing effect when applied to hair and a function of exerting a ceramide production promoting effect, and the function of the ceramide-containing composition of the present invention is one of these functions or It is not limited to two or more, and may have a function as a ceramide other than these functions.
  • the ceramide-containing composition of the present invention may be applied to the skin or used as food. In either case, it is possible to enjoy the above-mentioned functions including moisturizing of the skin, improvement of dark spots and wrinkles, protection against ultraviolet rays, and the like.
  • the ceramide-containing composition of the present invention promotes differentiation of keratinocytes in the skin and/or promotes de novo synthesis of ceramide by being applied to the skin and/or ingested as food. can be promoted.
  • the ceramide-containing composition of the present invention can, for example, increase gene expression of keratinocyte differentiation markers.
  • the keratinocyte differentiation marker is not particularly limited as long as it can confirm keratinocyte differentiation, but preferably includes a genetic marker. factor (NMF)) and Loricrin (a protein that serves as a framework for normal formation of the stratum corneum).
  • the ceramide-containing composition of the present invention can promote ceramide synthesis, for example, by enhancing the expression of genes associated with ceramide synthesis in the ceramide synthesis pathway.
  • De novo synthesis of ceramide is based on Serine + Palmitoyl CoA ⁇ 3-keto-sphinganine ⁇ Sphinganine ⁇ Dihydroceramide ⁇ Ceramide is known.
  • the differentiation marker of the ceramide synthesis pathway is not particularly limited as long as it is involved in the ceramide synthesis pathway, but preferably includes a genetic marker. (enzyme). SPT catalyzes the conversion of Serine+Palmitoyl CoA to 3-keto-sphinganine in the ceramide synthesis pathway.
  • the ceramide-containing composition of the present invention can increase skin thickness and promote skin turnover by promoting the increase and differentiation of keratinocytes.
  • the ceramide-containing composition of the present invention comprises at least about 0.01 wt% or more free ceramide, preferably at least about 0.1 wt% or more, at least about 0.3 wt% or more. , at least about 0.5% by weight or more, or at least about 0.8% by weight or more of free ceramide, and more preferably at least about 1% by weight or more of free ceramide.
  • the ceramide-containing composition of the present invention comprises at least about 0.01 wt% or more of glucosylceramide, preferably at least about 0.1 wt% or more, at least about 0.3 wt% or more. , at least about 0.5% by weight or more, or at least about 0.8% by weight or more of glucosylceramide, and more preferably at least about 1% by weight or more of glucosylceramide.
  • Polyphenol is a compound having a plurality of phenolic hydroxyl groups in the molecule, and the type of polyphenol contained in the composition of the present invention is not particularly limited. Examples include flavonol, flavone, isoflavone, tannin, catechin, quercetin, Anthocyanin, anthocyanidin, leucoanthocyanidin, proanthocyanidin, propyl gallate, catechin, rutin, quercetin, ferulic acid, resveratrol, procyanidin, theaflavin, curcumin, pycnogenol, rosmarinic acid, ellagic acid, quinic acid, chlorogenic acid, hydroxytyrosol etc. In the composition of the present invention, these polyphenols may be contained singly or in combination of two or more.
  • the polyphenol content in the compositions of the present invention is at least about 0.01 wt% or more, preferably at least about 0.1 wt% or more, at least about 0.3 wt% or more, at least about It can be at least 0.5% by weight, or at least about 0.8% by weight or more, and more preferably at least about 1% by weight or more.
  • the composition of the present invention may comprise resveratrol as a polyphenol in an amount of at least about 1 mg, at least about 3 mg, at least about 5 mg, at least about 7 mg per about 100 g of the composition of the present invention. , or at least about 10 mg resveratrol.
  • ceramide as a food raw material, many plant-derived ceramides such as konjac and rice are produced, but since all of them contain glucosylceramide as the main component, the ceramide-containing composition of the present invention has the same level of glucosylceramide. It is useful in that it contains less or more free ceramide.
  • compositions of the present invention contain ceramides and polyphenols in a weight ratio of total ceramides: polyphenols of about 1.0: about 0.5 to about 5.0, preferably about 1.0: It can be from about 0.7 to about 4.0.
  • a method for producing a ceramide-containing composition comprising the steps of washing wine fermented lees and extracting the residue obtained by the washing with a polar solvent.
  • the method for producing a ceramide-containing composition of the present invention comprises washing wine fermentation lees (bitartrate) obtained during wine brewing, and then extracting the residue with a polar solvent to obtain a fermented product extract. Characterized by There are no particular restrictions on the grape variety, the type of yeast, or the wine production method used as the raw material for the wine fermented lees. It can be used as wine fermentation lees. Wine yeast used for wine fermentation is not particularly limited, but natural yeast and cultured yeast can be used. Therefore, no matter what type of wine lees is used as a starting material, a composition with an increased content of ceramide or glucosylceramide can be produced by the method for producing a ceramide-containing composition of the present invention.
  • polar solvents such as water, methanol, ethanol, isopropyl alcohol, 1,3-butylene glycol, ethylene glycol, propylene glycol, glycerin, and ethyl acetate can be used as polar solvents. Two or more of these solvents may be mixed.
  • the ceramide-containing composition of the present invention can be efficiently extracted by using ethanol or hydrous ethanol, which is a mixture of ethanol and water, as the polar solvent.
  • the concentration of ethanol is not particularly limited, for example, the ethanol concentration can be about 10% to about 99% (wt/wt), preferably the ethanol concentration is at least about 70%. % or more, about 75% or more, about 80% or more, about 85% or more, about 90% or more, about 93% or more, about 95% or more, about 98% or more, about 99% or more (wt/wt) can be done.
  • the extraction temperature in the extraction step is about 30°C to about 80°C, preferably about 40°C to about 60°C.
  • the extraction time can be about 1 hour to about 8 hours, preferably about 3 hours to about 6 hours.
  • stirring extraction can be performed using an oar-type or propeller-type stirrer as the extraction method.
  • a solvent such as ethanol
  • the mixture is filtered, and the filtrate can be used as a ceramide fraction (the ceramide-containing composition of the present invention).
  • the scale of extraction can be set appropriately, so in another embodiment, a beaker is placed in a water bath, and wine lees and a solvent (such as ethanol) are stirred in the beaker for extraction. .
  • the wine fermentation lees can be washed with water in the washing step.
  • washing can be performed while stirring the fermented wine lees and water using an oar-type or propeller-type agitator.
  • the fermented wine lees and water can be stirred while being heated. After stirring for a period of time, it can be filtered and the residue used in the extraction process. Examples of water include purified water, sterilized water, and tap water. Purified water or sterilized water is preferable because it contains few impurities.
  • the washing temperature can be about 30°C to about 80°C, preferably about 40°C to about 60°C.
  • the cleaning time can be about 5 minutes to about 6 hours, preferably about 1 hour to about 2 hours.
  • the method for producing the ceramide-containing composition of the present invention can further adjust the pH of the extract obtained by the extraction step with a polar solvent.
  • a polar solvent By such pH adjustment, the color of the obtained ceramide-containing composition can be adjusted, and preferably a desired wine color can be obtained.
  • Such pH adjustment can be performed with an acid or alkali, and the type of acid or alkali is selected within a range that does not impair the effects of the ceramide-containing composition of the present invention.
  • food for specified health use, supplements, pharmaceuticals, quasi-drugs, or external skin preparations but not limited to, for example, phosphoric acid, tartaric acid, citric acid, or sodium carbonate can be done.
  • the ceramide-containing compositions of the present invention can be pH-adjusted for color depending on the desired application, wherein the pH-adjustment as described above reduces the pH of the ceramide-containing composition to, for example, less than about 5. , less than about 4.8, less than about 4.0, or less than about 3.5.
  • the extraction, separation, purification, identification, etc. of the ceramide-containing composition of the present invention a wide range of normal operations can be applied. It is also possible to adjust the pH, mix with desired excipients as necessary, and perform concentration, heat sterilization, freeze-drying, and the like.
  • the ceramide-containing composition of the present invention is obtained by washing wine fermented lees (wine lees) with preferably about 10 times the amount of water at about 60°C for about 1 hour, and then removing the residue. Preferably, it can be obtained by performing extraction with an ethanol solution of about 95% at about 40° C. for about 6 hours. Further, in one preferred embodiment of the present invention, the ceramide-containing composition of the present invention can adjust the pH of the extract obtained as described above to less than about 4.0.
  • the ceramide-containing composition of the present invention is mixed with an excipient such as cyclodextrin, further concentrated by replacing ethanol with water, heat sterilized at about 120 ° C., It can be lyophilized and powdered.
  • the ceramide-containing composition of the present invention is obtained by the production method described above, and contains glucosylceramide, free ceramide, and polyphenol at a weight ratio of about 1.0:1. .0: about 1.0 ratio. Moreover, in one preferred embodiment of the present invention, the ceramide-containing composition of the present invention can contain at least about 10 mg of resveratrol per about 100 g of the composition of the present invention by being obtained by the method described above. .
  • the ceramide-containing composition produced by the method of the present invention can be applied or blended for various uses.
  • Applications include, for example, cosmetics, pharmaceuticals, reagents, and compositions for oral intake (eg, health foods, foods with function claims, foods for specified health uses, supplements, and foods for specific uses).
  • the product containing the ceramide-containing composition of the present invention may contain excipients, carriers, additives, etc., the types of which are commonly used and pharmaceutically acceptable It is not particularly limited as long as it is a substance, and the blending amount thereof can be changed as appropriate.
  • excipients include sodium chloride, sodium citrate, etc.
  • carriers include sterilized water, physiological saline, and various buffer solutions. Preservatives, preservatives and the like can be mentioned.
  • the dosage form of the pharmaceutical containing the ceramide-containing composition of the present invention is not particularly limited, and may be appropriately selected as necessary.
  • Oral agents such as granules and powders, and parenteral agents such as injections, suppositories, and ointments can be used.
  • the amount of the ceramide-containing composition of the present invention in these pharmaceuticals is not particularly limited, and can be appropriately set according to the type and application of the pharmaceutical.
  • compositions for oral intake containing the ceramide-containing composition of the present invention optionally contain dextrin. , lactose, starch, and other excipients, flavors, pigments, gelatin, etc., and the ceramide-containing composition of the present invention can be blended.
  • the amount of the ceramide-containing composition of the present invention blended in these compositions for oral intake is not particularly limited, and can be appropriately set according to the type and use of the composition for oral intake.
  • these compositions for oral ingestion can contain various ingredients depending on the type.
  • the ceramide-containing composition of the present invention can also be added to foods and drinks that are normally consumed.
  • the ceramide-containing composition of the present invention can also be incorporated into external skin preparations including cosmetics, pharmaceuticals, and quasi-drugs.
  • the ceramide-containing composition of the present invention can be used for skin lotions, milky lotions, creams, lotions, soaps, facial cleansers, bath agents, eau de colognes, cosmetic oils, suntan/sunscreen lotions, powders, foundations, perfumes, packs, eye creams, etc. It can be incorporated into creams, eye shadows, mascaras, eyeliners, lipsticks, lip balms, shampoos, rinses, hair dyes, ointments, creams, liquids for external use, and the like.
  • external skin preparations including cosmetics, pharmaceuticals, and quasi-drugs
  • ceramide-containing composition of the present invention contain:
  • Various ingredients used in usual external preparations for skin e.g., surfactants, fatliquors, hair protectants, moisturizers, polymers, UV absorbers, sequestering agents, solvents, pH adjusters, vitamins, oxidation Antioxidants, antioxidant aids, preservatives, fragrances, oily components, higher alcohols, fatty acids, polar lipids, antibacterial components, viscosity modifiers, pigments, and the like can be blended.
  • the ceramide-containing composition of the present invention is spray-dried, freeze-dried, or vacuum-dried, and then made into powder, granules, or a solution for use in external skin preparations, food and drink, pharmaceuticals, and the like. can be easily included.
  • Example 1 Ceramide molecular species in wine sediment
  • 50 g of wine lees (Bitartrate) was washed with water at 60° C. for 1 hour to obtain a residue.
  • the residue was extracted with 95% ethanol at 40° C. for 6 hours.
  • the composition of ceramide molecular species in this extract was compared with ceramide molecular species similarly obtained from soybean.
  • the results are shown in FIG. As can be seen from these results, ceramide obtained from soybean is only glucosylceramide and does not contain free ceramide, while ceramide obtained from wine starch contains both glucosylceramide and free ceramide.
  • soybean ceramide pure soybean-derived glucosylceramide manufactured by Nagara Science Co., Ltd. was used.
  • Fig. 2 shows the results of confirming the ceramide molecular species and their amounts contained in the wine lees extract and the wine itself. From this result, it can be seen that wine itself contains neither free ceramide nor glucosylceramide, but the extract obtained from wine lees contains both free ceramide and glucosylceramide.
  • FIG. 3 shows a method for producing the wine lees extract (“W ceramide extract” in the figure) investigated in this example.
  • W ceramide extract was extracted from wine starch using 95% ethanol (60° C., 6 hours), and then W ceramide extract was further extracted from the residue using 60% ethanol (60° C., 6 hours). 3 hours).
  • FIG. 3 shows a method for producing the wine lees extract (“W ceramide extract” in the figure) investigated in this example.
  • W ceramide extract was extracted from wine starch using 95% ethanol (60° C., 6 hours), and then W ceramide extract was further extracted from the residue using 60% ethanol (60° C., 6 hours). 3 hours).
  • 60% ethanol 60° C., 6 hours
  • FIGS. 4 and 5 show the content (mg) of each component, and FIG. 5 shows the ratio of each component.
  • Example 3 Examination of cleaning process 2
  • Example 2 it was found that impurities can be removed more effectively by washing the wine lees than by first extracting it with ethanol. Therefore, washing solutions were investigated.
  • wine lees were washed with water, 10% ethanol, 30% ethanol, or 50% ethanol (both at 40 ° C. for 3 hours), and then 95% ethanol was removed from the residue after washing. was used to extract W ceramide extract (40° C., 6 hours) (FIG. 6). The results are shown in FIG.
  • Example 4 Examination of washing temperature
  • wine lees were washed with water at 40° C. or 60° C. (both 500 ml, 3 hours), and then W ceramide extract was extracted from the residue after washing with 95% ethanol. (40° C., 6 hours) (FIG. 8).
  • FIG. 8 The results are shown in FIG. As can be seen from this figure, contaminants (indicated by "others" in the figure) were significantly reduced when washed at 60°C compared to when washed at 40°C.
  • Example 5 Examination of washing time
  • Example 4 it was found that washing the wine lees with water at 60° C. was optimal, and therefore the washing time was investigated.
  • wine lees were washed for 30 minutes, 60 minutes, and 180 minutes (500 ml, 60° C. in each case), and then W ceramide extract was extracted from the residue after washing using 95% ethanol ( 40° C., 6 hours) (FIG. 10). The results are shown in FIG.
  • Example 6 Examination of amount of water added
  • 50 g, 60 g, and 75 g of wine lees were washed with 500 ml of water (10 times water, 8.3 times water, and 6.7 times water, each at 60° C. for 1 hour), Thereafter, W ceramide extract was extracted from the residue after washing using 95% ethanol (40° C., 6 hours) (FIG. 12). The results are shown in FIG.
  • Example 7 Examination of pH adjustment
  • tartaric acid, citric acid, or sodium carbonate was added to the W ceramide extract obtained by ethanol extraction, and then an excipient (cyclodextrin) was added, followed by freeze-drying into powder. The powder color in the case was confirmed (Fig. 14). The results are shown in FIG.
  • Example 8 Cell proliferation test
  • HaCaT cells human epidermal cells
  • Human epidermal cells HaCaT cells
  • a medium containing various concentrations of ceramide extract obtained from wine lees were cultured in a medium containing various concentrations of ceramide extract obtained from wine lees.
  • Cell proliferation was measured after 3 hours of culture.
  • cell proliferation It was measured using Counting Kit 8 (manufactured by Dojin Kagaku Kenkyusho Co., Ltd.). The results are shown in FIG.
  • the ceramide extract obtained from wine lees promotes cell proliferation in keratinocyte cells (HaCaT cells) (see 0.01-1 ⁇ g/mL addition group in FIG. 16).
  • Example 9 resveratrol amount measurement
  • the amount of resveratrol in the ceramide-containing composition of the present invention was measured.
  • Resveratrol is one of polyphenols with antioxidant action and is known as a component contained in red wine.
  • effects such as preventing cell oxidation and improving skin elasticity are expected.
  • the amount of resveratrol contained in red wine, wine lees (wine crystals), and ceramide-containing composition (wine ceramide) was measured using HPLC. The results are shown in FIG.
  • the amount of resveratrol contained in the ceramide-containing composition (wine ceramide) of the present invention is significantly increased compared to the amount of resveratrol contained in red wine or wine sediment (wine crystals). It can be seen that
  • Example 10 Expression enhancement effect of various gene markers by wine ceramide
  • HaCaT human keratinocyte cell line
  • DMEM medium containing 10% FBS (37° C., 5% CO 2 ).
  • FBS-free DMEM medium
  • Ceramides derived from other raw materials were purchased from manufacturers listed in Table 1.
  • Wine ceramides were extracted by the optimized procedure shown in Examples 2-6 (water wash with 10 times water at 60°C for 60 minutes and 95% ethanol extraction at 40°C for 6 hours).
  • a DMEM medium (FBS-free) supplemented with DMSO to a final concentration of 0.1% was used as a control. After culturing for 72 hours, mRNA was collected from the cells and cDNA was prepared. Using this, the mRNA expression of each marker was measured by qPCR. Each marker evaluated is as follows. ⁇ Differentiation markers; Pro-Filaggrin, Loricrin ⁇ Ceramide synthesis pathway marker; Serine-Palmitoyl Transferase
  • wine ceramide increased the mRNA expression level of the ceramide synthesis pathway marker SPT: Serine-Palmitoyl Transferase (an enzyme of the ceramide de novo synthesis pathway) compared to the control. This indicates that wine ceramide promotes the ceramide synthesis pathway.
  • SPT Serine-Palmitoyl Transferase
  • FIG. 20 also shows the Pro-filagrin mRNA expression level and SPT mRNA expression level when comparing the wine ceramide of the present invention with glucosylceramide and free ceramide.
  • the amounts of glucosylceramide and free ceramide added were calculated based on the equivalent amounts of glucosylceramide and free ceramide contained in wine ceramide. /mL was used.
  • Glucosylceramide and free ceramide used were those isolated from wine ceramide. As can be seen from this figure, wine ceramide is more effective in increasing the respective mRNA expression levels than glucosylceramide alone or free ceramide alone.
  • FIG. 21 also shows the Pro-Filaggrin mRNA expression level and SPT mRNA expression when comparing the wine ceramide of the present invention with each ceramide obtained from raw materials other than wine (rice ceramide, pine ceramide, and konjac ceramide). indicated the quantity.
  • the composition of each ceramide is as shown in Table 1. As can be seen from this figure, wine ceramide is more effective in increasing the respective mRNA expression levels than rice ceramide or pine ceramide.
  • Example 11 Effect of wine ceramide on keratinocytes
  • the efficacy of wine ceramide was evaluated in primary cultured keratinocytes cultured in 3D using Transwell.
  • the same wine ceramide as in Example 10 was used.
  • a culture medium containing wine ceramide was added to each of the stratum corneum side (upper well) and the basement membrane side (bottom well) of the transwell for a predetermined period of time and cultured.
  • the cells were cultured in a medium containing 0.1% DMSO. After culturing in each medium, frozen sections of 3D-cultured primary cultured keratinocytes were prepared and subjected to hematoxylin-eosin staining and immunostaining using an anti-ceramide antibody.
  • the hematoxylin/eosin-stained sections were observed under a phase-contrast microscope, and the results of measuring the thickness of the epidermal layer are shown in FIG.
  • the wine ceramide treatment increases the thickness of the skin.
  • skin thickness it is known that skin turnover decreases and becomes thinner with aging. may have also promoted
  • Sections immunostained with an anti-ceramide antibody were also observed under a fluorescence microscope, and the results of measuring the ceramide content in the epidermal layer are shown in FIG.
  • the immunostained area is enlarged and the amount of ceramide is increased compared to the control group.
  • the mRNA expression level of the ceramide synthesis pathway marker (SPT) was increased.
  • SPT ceramide synthesis pathway marker
  • the present invention can provide a ceramide-containing composition derived from wine fermentation lees. Moreover, according to the method of the present invention, it is possible to stably extract a ceramide composition from wine fermentation lees while removing contaminants, and to control the color of the ceramide composition. Furthermore, the ceramide composition of the present invention contains free ceramide and uses highly safe natural materials such as wine fermented lees. It is useful in fields such as cosmetics, pharmaceuticals, and quasi-drugs because it has excellent safety.

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Abstract

L'invention concerne une composition contenant un céramide dérivé d'une substance naturelle.　La présente invention fournit une composition contenant un polyphénol et un céramide. La présente invention concerne en outre une composition contenant un céramide dérivé de lies de fermentation du vin. L'invention concerne également un procédé de production d'une composition contenant un céramide, le procédé comprenant une étape de lavage de lies de fermentation du vin et une étape d'extraction du résidu de lavage résultant en utilisant un solvant polaire.
PCT/JP2022/038436 2021-10-15 2022-10-14 Composition contenant un céramide et son procédé de production WO2023063424A1 (fr)

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Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000135071A (ja) * 1998-10-30 2000-05-16 Sunstar Inc ワイン搾汁粕抽出物を含有する食品又は医薬組成物
JP2002238497A (ja) * 2001-02-19 2002-08-27 Fancl Corp 食品組成物
JP2003527843A (ja) * 2000-02-11 2003-09-24 コグニス・フランス・ソシエテ・アノニム ワイン製造残留物からの抽出物
JP2009165427A (ja) * 2008-01-18 2009-07-30 Masaru Yoshino 食品添加素材の製造方法
JP5013348B2 (ja) * 2010-07-23 2012-08-29 宮鍋 征克 スフィンゴ脂質の取得方法
JP2015105272A (ja) * 2013-12-03 2015-06-08 宮鍋 征克 紫芋もろみ蒸留粕抽出物
WO2018021476A1 (fr) * 2016-07-29 2018-02-01 株式会社 サティス製薬 Extrait de la peau de châtaigne
CN109007819A (zh) * 2018-07-25 2018-12-18 广州正广生物科技有限公司 一种抗糖化产品及其制备方法
CN111358729A (zh) * 2020-03-13 2020-07-03 猫头鹰(福州)日用品有限公司 一种含红酒多酚的保湿面膜及其制备方法
CN112042933A (zh) * 2019-06-08 2020-12-08 白华 一种培养肠道菌群改善脾胃虚弱的内服减肥食品配方及其制作方法

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000135071A (ja) * 1998-10-30 2000-05-16 Sunstar Inc ワイン搾汁粕抽出物を含有する食品又は医薬組成物
JP2003527843A (ja) * 2000-02-11 2003-09-24 コグニス・フランス・ソシエテ・アノニム ワイン製造残留物からの抽出物
JP2002238497A (ja) * 2001-02-19 2002-08-27 Fancl Corp 食品組成物
JP2009165427A (ja) * 2008-01-18 2009-07-30 Masaru Yoshino 食品添加素材の製造方法
JP5013348B2 (ja) * 2010-07-23 2012-08-29 宮鍋 征克 スフィンゴ脂質の取得方法
JP2015105272A (ja) * 2013-12-03 2015-06-08 宮鍋 征克 紫芋もろみ蒸留粕抽出物
WO2018021476A1 (fr) * 2016-07-29 2018-02-01 株式会社 サティス製薬 Extrait de la peau de châtaigne
CN109007819A (zh) * 2018-07-25 2018-12-18 广州正广生物科技有限公司 一种抗糖化产品及其制备方法
CN112042933A (zh) * 2019-06-08 2020-12-08 白华 一种培养肠道菌群改善脾胃虚弱的内服减肥食品配方及其制作方法
CN111358729A (zh) * 2020-03-13 2020-07-03 猫头鹰(福州)日用品有限公司 一种含红酒多酚的保湿面膜及其制备方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
SAWABE, AKIYOSHI; KAWAMURA, HARUKI; YOSHIDA, HIROKAZU; TAKEDA, RYUJI; IIDA, AKIRA; HAMAHARA, NORIMASA; KOMEMUSHI, SADAO; KAWAKAMI,: "3B019 Anti-aging effect of wine ingredients and effective use of wine compression residue", PROCEEDINGS OF THE ANNUAL MEETING OF JAPAN SOCIETY FOR BIOSCIENCE, BIOTECHNOLOGY, AND AGROCHEMISTRY (JSBBA2016), vol. 2016, 5 March 2016 (2016-03-05), pages 897, XP009546125 *
YAMASHITA SHINJI, HIGAKI CHISATO, KIKUCHI NOBUHIRO, SUZUKI DAISUKE, KINOSHITA MIKIO, MIYAZAWA TERUO: "Sake (Rice Wine) Brewing Hydrolyzes Highly Polar Sphingolipids to Ceramides and Increases Free Sphingoid Bases", JOURNAL OF OLEO SCIENCE, JAPAN OIL CHEMISTS SOCIETY, TOKYO, JP, vol. 70, no. 8, 1 January 2021 (2021-01-01), JP , pages 1147 - 1156, XP093058281, ISSN: 1345-8957, DOI: 10.5650/jos.ess21125 *

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