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WO2025173760A1 - Huile de pépins de raisin et procédé de production associé - Google Patents

Huile de pépins de raisin et procédé de production associé

Info

Publication number
WO2025173760A1
WO2025173760A1 PCT/JP2025/004884 JP2025004884W WO2025173760A1 WO 2025173760 A1 WO2025173760 A1 WO 2025173760A1 JP 2025004884 W JP2025004884 W JP 2025004884W WO 2025173760 A1 WO2025173760 A1 WO 2025173760A1
Authority
WO
WIPO (PCT)
Prior art keywords
oil
grape seed
grape
derived
activity
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/JP2025/004884
Other languages
English (en)
Japanese (ja)
Inventor
昭吾 鳥井
章悟 鈴木
健介 四本
建斗 國廣
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Albion Co Ltd
Original Assignee
Albion Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Albion Co Ltd filed Critical Albion Co Ltd
Publication of WO2025173760A1 publication Critical patent/WO2025173760A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61K8/96—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
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to an oil extracted from the seeds of the genus Vitaceae, particularly European grape (Vitis vinifera), wild grape (Vitis coignetiae), or hybrids thereof (hereinafter simply referred to as "grapes"), and a method for producing the same.
  • the present invention relates to an oil that contains a certain amount of grape seed-derived polyphenols as an active ingredient, and is safe, stable, and functional enough to be incorporated into cosmetics (including quasi-drugs; the same applies hereinafter), and a method for producing the same.
  • the present invention also relates to cosmetics containing grape seed-derived oil.
  • Grape seed oil is expected to contain polyphenols derived from grape seeds, but to increase safety, shelf life, and purity, refined oil, which is extracted from crude oil through a refining process to remove impurities, is used in cosmetics and other products.
  • this refining method also removes functional components such as polyphenols as impurities, so typical grape seed oil contains only a few tens of ppm to 100 ppm of polyphenols (Non-Patent Document 2). For this reason, there was an issue of not having an oil that contains a certain amount of polyphenols found in grape seeds and is safe, stable, and functional enough to be incorporated into cosmetics.
  • Patent Document 1 proposes an extraction method using liquefied dimethyl ether to obtain water-soluble natural products that contain both water-soluble and fat-soluble natural components and are not subject to denaturation associated with thermal decomposition.
  • polyphenols can be obtained from grape seeds as water-soluble components, and oil can be obtained as a fat-soluble component.
  • the grape seed-derived oil obtained by this method has poor stability due to its excessively high polyphenol concentration, and is highly irritating to the skin, making it difficult to use as a cosmetic ingredient.
  • grape seeds contain many useful polyphenols
  • conventional purification and extraction methods either produce too little or too much polyphenol, making it difficult to achieve the functionality required for cosmetics or to ensure safety and stability when used as an active ingredient in cosmetics.
  • the main objective of the present invention is to provide grape seed-derived oil containing an appropriate amount of polyphenols and a method for producing the same.
  • a first aspect of the present invention relates to grape seed-derived oil.
  • Grape seed-derived oil is preferably composed essentially of only natural ingredients, including natural grape seed-derived oil. However, the extraction solvent used to extract the oil from grape seeds may remain at 1 wt% or less.
  • the oil according to the present invention contains grape seed-derived polyphenols at 0.02 wt% or more and 0.10 wt% or less. Note that polyphenols are a general term for compounds with multiple phenolic hydroxyl groups. As shown in Example 1 below, if the grape seed-derived polyphenol content is 0.02 wt% or more, the functionality attributed to polyphenols can be fully exerted, making it suitable for cosmetics. Furthermore, if the grape seed-derived polyphenol content is 0.10 wt% or less, the oil is sufficiently mild in skin irritation, allowing it to be incorporated as an active ingredient in cosmetics.
  • the polyphenols preferably include catechin and epicatechin.
  • the oil of the present invention preferably contains grape seed-derived polyphenols as an active ingredient and possesses one or more of the following functionalities: antioxidant activity, anti-glycation activity, and anti-inflammatory activity. In this way, the present invention can impart functionality not exhibited by ordinary grape seed-derived oils.
  • the oil of the present invention contains grape seed-derived polyphenols as an active ingredient and preferably has one or more of the following activities: DPPH radical scavenging activity, ABTS radical scavenging activity, AGEs production inhibitory activity, SOD2 promotion activity, IL-1 ⁇ inhibitory activity, IL- ⁇ inhibitory activity, and GCLC promotion activity.
  • the grape seeds are seeds extracted from fresh grapes that have not undergone a fermentation process.
  • unpleasant odors and deterioration of the oil due to fermentation can be prevented, and refining processes that remove polyphenols, such as deodorization and deacidification, can be minimized.
  • the oil of the present invention does not cause skin sensitization.
  • the stability of the oil of the present invention is preferably guaranteed for at least three months when stored in a dark place at room temperature (15-30°C). Stability means that no solid precipitation or formation of an aqueous phase is observed under the above conditions.
  • a second aspect of the present invention is a cosmetic product containing the grape seed-derived oil according to the first aspect described above. More specifically, the grape seed-derived oil can be incorporated into cosmetics intended primarily for use as a skin topical agent.
  • a third aspect of the present invention is a method for producing grape seed-derived oil.
  • the oil production method of the present invention comprises steps 1 to 3.
  • step 1 fat-soluble components with a melting point of 4°C or higher are precipitated and removed from the crude grape seed oil extract.
  • step 2 components that volatilize at temperatures between 10°C and 35°C are separated from the crude grape seed oil extract under a reduced pressure of 1 to 6 kPa. While steps 1 and 2 may be performed in either order, it is preferable to perform step 2 after step 1.
  • the third step is a step for removing insoluble components from the extracted oil after steps 1 and 2. This allows for the efficient production of oil containing grape seed-derived polyphenols at 0.02 wt% to 0.10 wt%.
  • the present invention provides grape seed-derived oil containing an appropriate amount of polyphenols, as well as a method for producing the same.
  • an appropriate amount of polyphenols such as polyphenols, as well as a method for producing the same.
  • FIG. 1 is a flow diagram illustrating an example of a method for producing grape seed oil.
  • FIG. 2 shows an example of an extraction apparatus used in the production of grape seed oil.
  • FIG. 3 shows the extraction equipment used to produce the bulrush seed oil of Example 1.
  • FIG. 4 shows the extraction rate and total polyphenol content of the extract of Example 1 as a function of extraction time.
  • FIG. 5 shows the change in the total polyphenol content of the oil for each step in Example 1.
  • FIG. 6 shows the results of a comparison of the total polyphenol amounts between Example 1 and Comparative Example 1.
  • FIG. 7 shows the results of the qualitative test of polyphenols in the oil of Example 1.
  • FIG. 8 shows the measurement results of the DPPH radical scavenging activity of Example 1 and Comparative Example 1.
  • Example 9 shows the measurement results of the ABTS radical scavenging activity in Example 1 and Comparative Example 1.
  • FIG. 10 shows the results of measuring the AGE production inhibitory activity of Example 1 and Comparative Example 2.
  • FIG. 11 shows the results of measuring the gene expression activity in Example 1.
  • FIG. 12 shows the results of measuring the gene expression activity in Example 1.
  • the method for producing grape seed oil includes, in this order, a washing and drying step (step S1), a crushing step (step S2), an extraction step (step S3), a solvent separation step (step S4), a first filtration step (step S5), a reduced pressure distillation step (step S6), a second filtration step (step S7), a cold treatment step (step S8), and a sterilization filtration step (step S9).
  • step S1 washing and drying step
  • a crushing step S2 a crushing step
  • step S3 an extraction step
  • step S4 a solvent separation step
  • step S5 a first filtration step
  • step S6 a reduced pressure distillation step
  • step S7 a second filtration step
  • step S8 a cold treatment step
  • sterilization filtration step step S9
  • the washing and drying process involves washing and then drying the seeds extracted from fresh grape berries. Any method can be used for washing and drying, but it is preferable to use a method that does not deteriorate the components of the seeds (a method that does not apply heat). It is also preferable that the grapes used as the raw material for the oil are berries that have not undergone a fermentation process.
  • the grape fermentation process can be carried out using only the natural yeast contained in the grapes themselves, or by adding artificial yeast (yeast cultivated for winemaking) to the grape juice or seeds. Grapes generally begin to ferment naturally seven days after harvest, so it is preferable to carry out the washing and drying process within seven days (168 hours) of harvest.
  • the crushing step (step S2) is a step in which the grape seeds are crushed. Any crushing method can be used, but it is preferable to use a method that can powder the grape seeds in a short time so as not to deteriorate the components of the skin.
  • a known crusher used in the crushing of food products can be used to crush the grape seeds. It is preferable to crush the grape seeds immediately before the extraction step described below (specifically, within one hour) to avoid deterioration due to oxidation and light.
  • the grape seeds need to be stored for more than one hour after crushing, they should be stored in a sealed, light-blocking container to prevent deterioration due to oxidation and light.
  • the extraction process (step S3) is a process for extracting components from grape seeds. Any extraction method can be used, as long as the grape seeds are immersed in the extraction solvent and the grape seed components are dissolved into the extraction solvent.
  • a solution containing liquefied dimethyl ether is preferably used as the extraction solvent. Liquefied dimethyl ether is brought to a liquid state by raising the dimethyl ether above its saturated vapor pressure, but it may also be one to which a subsaturated amount of auxiliary solvent, such as water or alcohol, has been added.
  • the amount of auxiliary solvent added is preferably less than the saturation amount for the liquefied dimethyl ether, more specifically, less than 7% by mass of the liquefied dimethyl ether.
  • the extraction conditions are preferably 4 to 40°C and 1.0 MPa or less, and more specifically, 25°C and 0.7 MPa or less.
  • Other extraction solvents that can be used include, for example, ethanol, 1,3-butylene glycol, or an aqueous solution of these. This process results in an extract containing the grape seed extract and the extraction solvent.
  • the solvent separation step separates the extracted components from the extraction solvent by volatilizing the extraction solvent from the extract.
  • the extraction solvent can be volatilized by leaving the extract at a temperature between 15°C and 40°C under atmospheric pressure (101.33 kPa), or by irradiating the extract with ultrasound for a short period of time (10 minutes or less). More specifically, if liquefied dimethyl ether is used as the extraction solvent, the liquefied dimethyl ether is volatilized and separated from the extract by heating the extract to 30°C under atmospheric pressure. Even after this volatilization step, traces of liquefied dimethyl ether may remain in the extract.
  • Any remaining dissolved liquefied dimethyl ether can be volatilized by irradiating it with ultrasound for 10 minutes. This allows the extraction solvent (liquefied dimethyl ether) to be almost completely separated from the extract. In this way, the extraction solvent is separated from the extract to obtain the extracted crude oil.
  • the first filtration step (step S5) filters the extracted crude oil to remove impurities and solids, such as lipids with high melting points, that are mixed in the extracted crude oil.
  • This first filtration step is primarily intended to precipitate and remove fat-soluble components with melting points of 4°C or higher from the extracted crude oil from grape seeds.
  • the extracted crude oil contains fat-soluble components derived from grape seeds with melting points of 4°C or higher, such as monounsaturated fatty acids such as oleic acid (melting point approximately 13°C), saturated fatty acids such as palmitic acid (melting point approximately 63°C) and stearic acid (melting point approximately 70°C), phytosterols (melting point approximately 136°C), and carotenoids (melting point approximately 63-183°C).
  • the first filtration step is preferably performed under temperature and pressure conditions (specifically, atmospheric pressure, 13°C or lower) that result in at least oleic acid being in a solid state.
  • an example of a fat-soluble component derived from grape seeds with a melting point of 4°C or higher is linoleic acid (melting point approximately -5°C).
  • Any filtering method can be used, but filter paper or a membrane filter with a mesh size of 1.0 to 10 ⁇ m can be used, for example.
  • This process removes impurities and lipids from the extracted crude oil, leaving a mixture of water, water-soluble components, and oil derived from grape seeds.
  • This water-soluble component includes polyphenols.
  • the filtered mixture typically contains polyphenols at a very high concentration of 3 wt% (3,000 mg/kg) or more. Therefore, while this mixture is expected to be highly functional, its stability and safety are poor for cosmetic applications, and it cannot be used as a cosmetic ingredient in its current state.
  • the reduced-pressure distillation process separates volatile components that volatilize at reduced pressure below 35°C from the filtered mixture.
  • This reduced-pressure distillation process primarily aims to remove water and other volatile substances from the filtered mixture. When removing water from the mixture, heating the mixture above 35°C may denature the active ingredients contained in the mixture. Therefore, it is preferable to keep the mixture temperature below 35°C and instead place the mixture under reduced pressure.
  • the saturated vapor pressure of water at 10°C is 1.227 kPa
  • the saturated vapor pressure of water at 35°C is 5.6216 kPa.
  • the second filtration step involves filtering the extracted oil again after vacuum distillation to remove any remaining solids.
  • Any filtering method can be used; for example, a filter paper or membrane filter with a mesh size of 0.3 to 0.6 ⁇ m can be used.
  • This step removes the solids precipitated in the vacuum distillation step (step S6), yielding a clear grape seed-derived oil (refined oil).
  • This solid contains some of the grape seed-derived polyphenols. Therefore, when comparing the mixture after the first filtration step (step S5) with the oil after the second filtration step (step S7), the latter has a lower polyphenol concentration. However, because not all polyphenols are removed after the second filtration step, a moderate amount of polyphenols remains in the oil.
  • This grape seed-derived oil has a polyphenol concentration of 0.02 to 0.10 wt% (200 to 1000 mg/kg). This polyphenol concentration satisfies the stability and safety requirements for cosmetic use, so this oil can be used as a cosmetic ingredient.
  • the cold treatment step (step S8) is a step aimed at precipitating insoluble matter contained in the grape seed-derived oil.
  • the method of cold treatment is not important, but specifically, it is preferable to leave the oil in a refrigerator at 4°C or similar, and store it in a storage facility where there is no temperature change and it is not exposed to light. This step allows the precipitating of insoluble matter that was not completely removed in the filtration step (step S7).
  • the sterile filtration process (step S9) is a process in which the grape seed-derived oil after the cold treatment process is sterile filtered and sterilized.
  • Sterile filtration can be performed using, for example, a membrane filter with a mesh size of 0.22 ⁇ m or less.
  • the sterilized grape seed-derived oil is filled into a sterilized container.
  • Sterile filtration is preferably performed in a clean environment, such as a clean room or clean bench.
  • this grape seed-derived oil has a polyphenol concentration of 0.02-0.10 wt% (200-1000 mg/kg).
  • the oil that underwent the vacuum distillation process (S6) and filtration process (S7) was able to sufficiently reduce the total polyphenol content to approximately 0.02 wt%, satisfying the stability and safety requirements for cosmetic use.
  • the oil that did not undergo these vacuum distillation processes (S6) and filtration (S7) had a total polyphenol content of approximately 0.3 wt%, which resulted in poor stability and skin safety.
  • the total polyphenol content of the oil is excessive at approximately 0.3 wt%, and the appropriate total polyphenol content should be approximately one-third of that, at 0.10 wt%. Therefore, based on the results obtained in Example 1 described below, it is appropriate to set the lower limit of polyphenol concentration for grape seed-derived oil at 0.02 wt% and the upper limit at 0.10 wt%.
  • Figure 2 shows an example of an extraction apparatus for producing grape seed oil according to this embodiment. Note that Figure 2 merely shows a schematic representation of the shape, size, and arrangement of the components, sufficient to enable understanding of the extraction apparatus.
  • the extraction system 100 includes a storage tank 1 for storing liquefied dimethyl ether 2, an extraction tank 6 for bringing a raw material 7 into contact with the liquefied dimethyl ether 2, a separation tank 11 for separating the liquid extracted from the extraction tank 6, and a pump 3 for pumping the liquefied dimethyl ether 2 from the storage tank 1 to the extraction tank 6.
  • the extraction device 100 also has conduits 5, 10, 12, 14, 16, 19, 20, and 23 for introducing and discharging liquefied dimethyl ether 2, and valves 4, 9, 13, 15, 18, 21, and 22 for adjusting the air pressure in each tank to control the introduction and discharge of liquefied dimethyl ether 2.
  • the pressure in the extraction tank 6 and separation tank 11 can be adjusted to maintain the liquefied dimethyl ether 2 in a liquid state.
  • the storage tank 1 functions as a storage means for storing liquefied dimethyl ether 2.
  • the pump 3, valve 4, and conduit 5 function as a liquid delivery means for delivering the liquefied dimethyl ether 2 from the storage tank 1 to the extraction tank 6.
  • the extraction tank 6 functions as a contact means for bringing the liquefied dimethyl ether 2 into contact with the raw material 7 to obtain an extract.
  • the valve 9 and conduit 10 function as a discharge means for delivering the extract from the extraction tank 6 to the separation tank 11.
  • the separation tank 11 functions as a separation means for separating the liquefied dimethyl ether 2 from the extract.
  • the conduit 12 and valve 13 connected to the separation tank 11 function as a vaporization means for vaporizing the liquefied dimethyl ether.
  • the condenser 17 connected to the conduit 16 functions as a condensation means for condensing the dimethyl ether discharged from the separation tank 11 from a gas back into a liquid.
  • the conduits 19 and 20 function as a supply means for supplying the liquefied dimethyl ether 2 to the storage tank 1.
  • the extraction device 100 may further include optional components such as a thermometer and a pressure gauge for detecting the temperature and air pressure within each of the storage tank 1, extraction tank 6, and separation tank 11, an agitator for stirring within each tank, and a device for circulating an inert gas such as nitrogen to purge active gases such as oxygen within each tank and conduit.
  • optional components such as a thermometer and a pressure gauge for detecting the temperature and air pressure within each of the storage tank 1, extraction tank 6, and separation tank 11, an agitator for stirring within each tank, and a device for circulating an inert gas such as nitrogen to purge active gases such as oxygen within each tank and conduit.
  • extracted crude oil from the raw material 7 can be obtained as follows.
  • the raw material 7 is the aforementioned grape seeds that have been washed, dried, and then crushed.
  • Filters 8 are installed on both the upstream and downstream sides of extraction tank 6.
  • Raw material 7 (grape seeds) is introduced into this extraction tank 6.
  • valves 4, 9, 13, 15, 18, 21, and 22 are all closed. If there is not enough liquefied dimethyl ether 2 stored in storage tank 1, valve 21 is opened and liquefied dimethyl ether 2 is supplied to storage tank 1 via conduit 20, after which valve 21 is closed. At this time, valve 18 may be opened when valve 21 is opened, and valve 18 may be closed when valve 21 is closed.
  • valve 4 is opened, and pump 3 extracts liquefied dimethyl ether 2 from storage tank 1 and sends it to extraction tank 6 via conduit 5. After liquefied dimethyl ether 2 has been introduced into extraction tank 6 until it comes into contact with raw material 7, valve 4 is closed.
  • valves 4 and 9 are opened, and pump 3 introduces liquefied dimethyl ether 2 from storage tank 1 into extraction tank 6 via conduit 5.
  • the extract in extraction tank 6 is then introduced into separation tank 11 via conduit 10.
  • new liquefied dimethyl ether 2 is drawn from storage tank 1 into extraction tank 6, the extract in extraction tank 6 is pushed into separation tank 11.
  • the contents of extraction tank 6 are replaced with new liquefied dimethyl ether, but raw material 7 remains in extraction tank 6 due to the presence of filters 8 upstream and downstream of extraction tank 6.
  • new liquefied dimethyl ether is introduced into extraction tank 6, the extract is pushed out of extraction tank 6 and separated from raw material 7.
  • Valves 4 and 9 are opened after a predetermined time has elapsed since liquefied dimethyl ether 2 was introduced into extraction tank 6, allowing the moisture and other components of raw material 7 to transfer to liquefied dimethyl ether 2. At this time, liquefied dimethyl ether 2 may be left in contact with raw material 7 for a predetermined period of time, or the liquefied dimethyl ether 2 may be stirred.
  • valves 4 and 15 and opening valves 9, 13, and 22 the pressure in the path from valve 4 to valve 13 becomes less than the saturated vapor pressure of dimethyl ether.
  • the liquefied dimethyl ether 2 in this path then vaporizes and is discharged from conduit 23 via conduit 14.
  • pump 3 can be used to discharge the dimethyl ether if necessary.
  • the extracted crude oil remains in separation tank 11, with the liquefied dimethyl ether 2 having evaporated and been separated from the extract.
  • valve 22 leading to the outside air is open and valve 15 leading to condenser 17 is closed, but valve 22 may also be closed and valve 15 open.
  • vaporized dimethyl ether is introduced into condenser 17 via conduit 16.
  • dimethyl ether is re-condensed in condenser 17 to produce liquefied dimethyl ether 2.
  • valve 18 by opening valve 18, the produced liquefied dimethyl ether 2 is introduced into storage tank 1 via conduit 19. This allows it to be reused as liquefied dimethyl ether 2.
  • the extracted crude oil remaining in the separation tank 11 is subjected to the first filtration step (step S5), vacuum distillation step (step S6), second filtration step (step S7), cold treatment step (step S8), and sterilization filtration step (step S9) described above.
  • the extracted crude oil can be subjected to steps S6 to S9 using a known membrane filter or evaporator.
  • the grape seed-derived oil obtained through the above process may be used as is, but ingredients used in cosmetics and quasi-drugs can be added as appropriate, provided that the effects of the oil are not impaired.
  • ingredients used in cosmetics and quasi-drugs include oils and fats, waxes, hydrocarbons, fatty acids, alcohols, esters, surfactants, metal soaps, pH adjusters, preservatives, fragrances, moisturizers, powders, UV absorbers, thickeners, pigments, antioxidants, whitening agents, chelating agents, excipients, and film-forming agents.
  • Grape seed-derived oil can also be incorporated into cosmetics or quasi-drugs, primarily for use as topical skin preparations.
  • cosmetic and quasi-drug formulations include lotions, creams, emulsions, gels, aerosols, essences, packs, cleansers, bath additives, foundations, dusting powders, lipsticks, ointments, and patches.
  • the antioxidant composition of the present invention can also be incorporated into soaps, body washes, facial cleansers, shampoos, rinses, treatments, and toothpastes, for example.
  • DPPH radical scavenging activity was measured by reacting a sample with a DPPH radical solution (room temperature, 30 min), measuring the absorbance (517 nm) of the solution using a plate reader, and calculating the activity (%) relative to the blank.
  • ABTS radical scavenging activity was measured by reacting a sample with an ABTS radical solution (37°C, 4 min), measuring the absorbance (734 nm) of the solution using a plate reader, and calculating the activity (%) relative to the blank.
  • the anti-glycation activity of grape seed oil was measured using an AGEs (advanced glycation end products) production inhibitory activity test.
  • a BSA (bovine serum albumin) solution and a glucose solution were added to the sample and allowed to react (60°C, 96 hours).
  • the fluorescence of the reaction solution was measured using a plate reader (excitation wavelength 370 nm, fluorescence wavelength 440 nm), and the activity (%) relative to the blank was calculated.
  • RNA extraction reagent "TRI Reagent" (Merck KGaA, Darmstadt, Germany).
  • RNA was synthesized by reverse transcription with Oligo dT Primer using the "Primescript RT reagent kit" (Takara Bio, Shiga, Japan). mRNA levels were quantified by PCR using primers for each gene in a "LightCycler 96" PCR device (Roche, Basel, Switzerland) with the PCR reagent "Luna Universal qPCR Master Mix” (New England Biolabs, MA, USA). The Cq values of the measurement data were calculated using the delta Ct method, and the expression level of each gene was shown as a relative value based on the Cq value of GAPDH.
  • RNA was synthesized by reverse transcription with Oligo dT Primer using the "Primescript RT reagent kit" (Takara Bio, Shiga, Japan). mRNA levels were quantified by PCR using primers for various genes in a PCR device "LightCycler 96" (Roche, Basel, Switzerland) with the PCR reagent "Luna Universal qPCR Master Mix” (New England Biolabs, MA, USA). The Cq values of the measurement data were calculated using the delta Ct method, and the expression level of each gene was shown as a relative value based on the Cq value of GAPDH.
  • Example 1 grape seed oil was produced according to the procedure shown in Figure 1.
  • the grape seeds used as the raw material were extracted from fresh grapes that had not undergone fermentation, washed, and seeds that floated on the water were removed (sorted). The seeds were then dried to a moisture content of approximately 6% by mass and crushed to a size of 1.0 mm or less immediately before extraction.
  • an extract was produced from grape seeds using the extraction apparatus shown in Figure 3. Specifically, 18.0 g of grape seeds 57, crushed to a length of approximately 1.0 mm or less, were placed in a 25 mL extraction tank 56, with filters 55, 58 installed upstream and downstream. Next, valve 52 was closed and valve 53 was open, and dimethyl ether 51 was filled into syringe pump 50, which was then liquefied at 25°C and 0.7 MPa. The atmosphere in separation tank 62 was previously replaced with dimethyl ether, and valves 52, 53, 54, 59, 60, and 61 were closed.
  • the extraction apparatus shown in Figure 3 is configured in such a way that dimethyl ether is not circulated as in the extraction apparatus 100 shown in Figure 2.
  • valves 53, 54, 59, and 60 were opened, and liquefied dimethyl ether was supplied to extraction tank 56 by syringe pump 50.
  • syringe pump 50 was stopped, valves 54 and 59 were closed, and crushed grape seeds 57 were immersed in the liquefied dimethyl ether.
  • Valves 54 and 59 were opened, and liquefied dimethyl ether was again supplied using syringe pump 50.
  • the flow rate was adjusted to 2.5 mL/min and the residence time to 10 minutes, and 30 mL of extract was collected in separation tank 62.
  • Valve 60 was then closed, separation tank 62 was removed from the apparatus, and the pressure was returned to atmospheric pressure in a designated draft chamber to volatilize the liquefied dimethyl ether and produce an extract.
  • the resulting extract was then irradiated with ultrasound for 10 minutes using an ultrasonic cleaner, and then left to stand overnight at 4°C to completely volatilize the liquefied dimethyl ether, yielding an extracted crude oil.
  • This extracted crude oil was first filtered using 7 ⁇ m filter paper to remove solid lipids and impurities, and then distilled under reduced pressure using an evaporator at 40°C for 5 hours to separate the water and volatile components, yielding the extracted oil.
  • the air pressure inside the evaporator was set to 5.6 kPa.
  • the precipitate in the extracted oil that formed during vacuum distillation was separated by a second filtration using a 0.45 ⁇ m membrane filter. This precipitate is presumed to be some of the water-soluble components that had dissolved in the water.
  • the mixture was then left to stand overnight at 4°C for cold treatment (precipitation), and after sterilization filtration using a 0.22 ⁇ m membrane filter in a clean bench, the resulting oil (refined oil) was filled into brown bottles.
  • Comparative Example 1 used oil produced by pressing grape seeds of the same variety as in Example 1. Specifically, the grape seeds were washed, sorted, dried, and crushed using the same procedures as in Example 1. The crushed grape seeds were then pressed using a screw press to extract the oil. The oil thus extracted was processed using the same procedures as in Example 1, including the second filtration, cold treatment, and sterilization filtration, and then bottled in brown bottles.
  • Comparative Example 2 oil (extracted crude oil) was used, which was obtained by omitting the filtration step (step S5) and subsequent steps in Example 1.
  • Comparative Example 3 oil (filtered crude oil extract) was used, which was obtained by omitting the vacuum distillation (moisture removal) step (step S6) and subsequent steps in Example 1.
  • FIG. 4 shows the extraction rate and total polyphenol content of the extract obtained in the extraction process of Example 1 as a function of extraction time.
  • the extraction conditions were 25°C, 0.7 MPa, and a residence time of 10 minutes.
  • the crude oil was dried in a vacuum dryer (40°C, 5.33 kPa, 12 hours), and the remaining extract was removed.
  • the extraction rate was 16.5% by mass and the total polyphenol content was 3136 mg/kg (0.3136 wt%) at extraction times of 36 minutes or longer, and remained almost constant thereafter. Therefore, a 36-minute extraction time was determined to be optimal.
  • the amount of liquefied dimethyl ether delivered was 3.3 kg per 1 g of grape seeds.
  • the oil obtained in the extraction process contained a high amount of total polyphenols, which is expected to have high functionality. However, due to its poor stability and skin safety, it cannot be used as a cosmetic ingredient as is, and therefore requires further processing.
  • Figure 5 shows the change in the total polyphenol content of the oil after each step of the extraction process (S3) in Example 1.
  • the total polyphenol content in the oil was 3100 mg/kg (0.31 wt%) in the solvent separation process (S4), and was reduced to 2900 mg/kg (0.29 wt%) by removing the solids in the first filtration process (S5).
  • the water was then removed in the vacuum distillation process (S6), and the precipitated solids were separated in the filtration process (S7).
  • the total polyphenol content was reduced to 250 mg/kg (0.025 wt%). While most of the polyphenols obtained by extraction were removed, the remaining polyphenols are presumed to be relatively soluble in the oil.
  • the total polyphenol content in the oil after the cold treatment process (S8) and the sterilization filtration process (S9) was 250 mg/kg (0.025 wt%), showing almost no change. Therefore, it can be said that the vacuum distillation step (S6) and the filtration step (S7) contribute to achieving an appropriate amount of total polyphenols in the oil.
  • GCLC is a type of enzyme called glutamylcysteine ligase, which is involved in the biosynthesis of glutathione (GSH). GSH plays an important role in eliminating oxidative stress and toxins within cells, as well as providing antioxidant defense within cells. GCLC combines glutamic acid with cysteine to form glutamylcysteine, which then leads to the biosynthesis of GSH.
  • Example 1 promotes the production of enzymes involved in glutathione synthesis in human skin keratinocytes, and is expected to have antioxidant effects such as eliminating oxidative stress and toxins, and providing antioxidant protection within cells.
  • the grape seed oil of the present invention exhibits its functionality by containing a certain amount of polyphenols contained in grape seeds themselves, while also ensuring safety and stability. Therefore, the grape seed oil of the present invention is suitable for use in cosmetics.

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Abstract

Sont divulgués une huile issue de pépins de raisin contenant une quantité appropriée d'un polyphénol ; et un procédé de production de l'huile. Le procédé de production d'une huile issue de pépins de raisin, comprend : une première étape de précipitation et d'élimination d'un composant liposoluble ayant un point de fusion de 4 °C ou supérieur à partir d'une huile extraite brute issue de pépins de raisin ; une deuxième étape consistant à séparer un composant qui se volatilise de l'huile extraite brute dans une condition de température de 10 à 35 °C, dans une atmosphère à pression réduite de 1 à 6 kPa ; et une troisième étape consistant à éliminer les composants insolubles d'une huile extraite obtenue après la première et la deuxième étape. Ainsi, une huile contenant de 0,02 à 0,10 % en poids inclus d'un polyphénol tiré de pépins de raisin est obtenue.
PCT/JP2025/004884 2024-02-14 2025-02-14 Huile de pépins de raisin et procédé de production associé Pending WO2025173760A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006058382A1 (fr) * 2004-12-02 2006-06-08 Bio Extracts Holdings Pty Ltd Procede d’extraction
JP2020006357A (ja) * 2018-06-29 2020-01-16 株式会社リコー 液体の製造方法及び液体の製造装置
JP2020519642A (ja) * 2017-05-12 2020-07-02 シャクリー コーポレイション 美容利用のための局所マスカダイン配合物
KR102135551B1 (ko) * 2019-08-29 2020-07-20 주식회사 씨앤피코스메틱스 포름오노네틴을 지표성분으로 포함하는 레드 프로폴리스 추출물을 포함하는 안티에이징 효과가 우수한 화장료 조성물
CN111869821A (zh) * 2020-07-31 2020-11-03 廊坊师范学院 一种葡萄籽复配营养代餐粉及其制备方法
CN114836258A (zh) * 2022-04-20 2022-08-02 宁夏松海盛华农林科技开发有限公司 利用酿酒后的葡萄籽提取葡萄籽油的方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006058382A1 (fr) * 2004-12-02 2006-06-08 Bio Extracts Holdings Pty Ltd Procede d’extraction
JP2020519642A (ja) * 2017-05-12 2020-07-02 シャクリー コーポレイション 美容利用のための局所マスカダイン配合物
JP2020006357A (ja) * 2018-06-29 2020-01-16 株式会社リコー 液体の製造方法及び液体の製造装置
KR102135551B1 (ko) * 2019-08-29 2020-07-20 주식회사 씨앤피코스메틱스 포름오노네틴을 지표성분으로 포함하는 레드 프로폴리스 추출물을 포함하는 안티에이징 효과가 우수한 화장료 조성물
CN111869821A (zh) * 2020-07-31 2020-11-03 廊坊师范学院 一种葡萄籽复配营养代餐粉及其制备方法
CN114836258A (zh) * 2022-04-20 2022-08-02 宁夏松海盛华农林科技开发有限公司 利用酿酒后的葡萄籽提取葡萄籽油的方法

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