WO2016035221A1 - Peach extract and method for producing same - Google Patents

Peach extract and method for producing same Download PDF

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Publication number
WO2016035221A1
WO2016035221A1 PCT/JP2014/080656 JP2014080656W WO2016035221A1 WO 2016035221 A1 WO2016035221 A1 WO 2016035221A1 JP 2014080656 W JP2014080656 W JP 2014080656W WO 2016035221 A1 WO2016035221 A1 WO 2016035221A1
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Prior art keywords
peach
extract
hexane
extraction
ethanol
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PCT/JP2014/080656
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French (fr)
Japanese (ja)
Inventor
武蔵 岡安
耕平 黒田
淳子 山川
真起子 小林
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株式会社岡安商店
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Publication of WO2016035221A1 publication Critical patent/WO2016035221A1/en

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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
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/09—Mashed or comminuted products, e.g. pulp, purée, sauce, or products made therefrom, e.g. snacks
    • 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
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin

Definitions

  • the present invention relates to a peach extract having active oxygen scavenging ability and containing glycosphingolipid (ceramide component), and a method for producing the same.
  • the present inventors also focused on useful trace components contained in by-products produced in the production process of edible rice bran oil made from vegetable oil and fat, especially rice bran, and as a result, a method for extracting and producing rice ceramide And has been providing naturally derived rice ceramide (sphingoglycolipid).
  • the rice ceramide provided by the present inventors is a ceramide derived from a natural material, and its safety is high and its purity is extremely high, so far, food, cosmetics, quasi drugs, and those It has been widely used as a material for processed products.
  • Ceramide is a kind of sphingolipid and is a generic name for a group of compounds in which sphingosine, which is a long-chain amino alcohol, and an fatty acid are amide-bonded.
  • This ceramide is known to exist in high concentrations in the cell membrane, and in particular, it exists as a main component of the skin keratinocyte lipid, and has a barrier function as a moisturizing function that prevents evaporation of moisture from inside the skin. I'm in charge.
  • ceramide in keratinocyte lipids decreases with aging and moisturizing ability declines, causing dry skin, wrinkles, or rough skin.
  • ceramide is insufficient as a cause of not only skin aging but also skin roughness and rough skin caused by atopic dermatitis. That is, dry skin in atopic dermatitis is originally characterized by low ceramide, and as the barrier function of the skin decreases, moisture tends to be lost from the inside of the skin to the outside. It has been reported that chemicals and chemicals can easily enter the skin, resulting in allergic reactions and various symptoms such as itching and inflammation.
  • Patent Document 1 various studies on plant-derived ceramide components such as various fruits or vegetables have been studied.
  • peach is said to have a high content of ceramide, and a technique for extracting ceramide from peach has been proposed (Patent Document 2).
  • Patent Document 2 Regarding the peach content, not only ceramide extraction but also the physiological activity of the peach fruit itself has been studied, and the polyphenol contained in the peach fruit and the active oxygen scavenging function of the peach itself have also been reported.
  • the extraction of ceramide from peach described in Patent Document 2 described above is the preparation of a glucosylceramide fraction by an extraction method using a chloroform / methanol mixture as an extraction solvent, taking into account the toxicity of chloroform and methanol used as the extraction solvent. In this case, it is not preferable from the viewpoint of safety. Therefore, examination of the extraction method of the ceramide from the peach which can ensure more safety is requested
  • Examples of techniques for extracting and producing ceramide components from plant components such as various fruits and vegetables that have been proposed so far include, for example, alcohol-based solvents (for example, grapes, cherries, wheat, rice, soybeans, etc.) 2) selected from water, ethanol, acetone, hexane, and a method of extracting the rice bran with ethanol after degreasing and pretreating the camellia rice cake with hexane (Patent Document 1) Extraction method using a mixed solvent of at least seeds (Patent Document 4), after hydrolyzing plant materials such as wheat, soybeans, corn, rice bran, etc. with an alkaline ethanol solvent, extraction method using a mixed solvent of hexane, acetone, and water (Patent Document 5 and Patent Document 6) are known.
  • alcohol-based solvents for example, grapes, cherries, wheat, rice, soybeans, etc.
  • Patent Document 4 Extraction method using a mixed solvent of at least seeds
  • Patent Document 5 and Patent Document 6 extraction method using a
  • the present inventors also tried the extraction methods described in the above-mentioned patent documents in order to extract the ceramide component from peach, but were not satisfied. Therefore, in view of the present situation, as a result of examining a method for efficiently and safely extracting a ceramide component from peach, the peach raw material was extracted with ethanol or an ethanol / hexane mixture, and the obtained extract was further diluted with hexane / water. It has been found that a peach extract having an active oxygen scavenging ability and containing a glycosphingolipid (ceramide component) can be efficiently obtained by partition extraction, and the present invention has been completed.
  • the present invention provides a method for efficiently and safely extracting a peach extract having active oxygen scavenging ability obtained from peaches, and a method for extracting active peaches obtained by the production method, and a glycosphingolipid ( It is an object to provide a peach extract containing a ceramide component).
  • a peach processed peach, mature peach, or a processed peach residue containing fiber components obtained by removing seeds and fruit juice from the extracted peach or mature peach, ethanol, or ethanol /
  • the present invention is a peach extract whose active oxygen scavenging ability is DPPH (diphenylpicrylhydrazyl) activity.
  • DPPH diphenylpicrylhydrazyl
  • the present invention is a peach extract having a DPPH activity of 5% or more and a ceramide content of 0.5% or more.
  • the present invention is a method for producing a peach extract having active oxygen scavenging ability and containing a sphingolipid (ceramide component), specifically, a fruit peach, a mature peach, or Peach processing residue containing fiber components obtained by removing seeds and fruit juice from plucked peach or mature peach is extracted with ethanol or ethanol / hexane mixture, and the resulting extract is further partitioned and extracted with hexane / water And a method for producing a peach extract containing a sphingoglycolipid (ceramide component).
  • ceramide component specifically, a fruit peach, a mature peach, or Peach processing residue containing fiber components obtained by removing seeds and fruit juice from plucked peach or mature peach is extracted with ethanol or ethanol / hexane mixture, and the resulting extract is further partitioned and extracted with hexane / water
  • the volume ratio of the extract used for extracting the peach processing residue and the hexane and water used for the partition extraction of the extract is 1: 0.5: 0.5 to 1: 2: 2 is a peach extract, and a production method thereof.
  • the present invention is a powdery product obtained by mixing the above-mentioned extract with cyclodextrin, or a food, cosmetic, quasi-drug, or processed product thereof in the form of an aqueous solution.
  • a peach extract having active oxygen scavenging ability can be obtained more efficiently than a peach raw material by a relatively simple method with excellent safety.
  • the method for producing a peach extract provided by the present invention is not limited to the point that an extract of ethanol or an ethanol / hexane mixture, ie, a so-called primary extract, is further partitioned and extracted with hexane / water. This is a manufacturing method that has not been studied and is extremely specific.
  • the peach extract thus produced contains ceramide (sphingoglycolipid), polyphenol and glycoside, has active oxygen scavenging ability, high safety, food, cosmetics or pharmaceuticals. It is extremely useful as a raw material for quasi-drugs and processed products.
  • the present invention extracts a peach processed residue containing a fiber component obtained by removing seeds and fruit juice from a fruit peach, mature peach, or fruit peach or mature peach, which is a peach raw material, with ethanol or an ethanol / hexane mixture.
  • a peach extract characterized by having an active oxygen scavenging ability obtained by further partitioning and extracting the extract with hexane / water and containing a glycosphingolipid (ceramide component).
  • the fruit peach used as a raw material is a fruit peach (young peach) by pruning in the peach production process, and the mature peach is a peach suitable for being shipped to the market as a peach.
  • a peach processing residue is a peach processing residue containing the fiber component which remove
  • the peach harvest is about 150,000 tons annually nationwide, and the fruit peach (young peach) produced during the harvesting process is said to be about 15,000 tons, which is about 10% of the peach harvest.
  • a small part of this fruit peach is processed for food such as pickles, but most of it is used as fertilizer as it is without being processed. There was no means for effective use.
  • peach fruit juice peach juice
  • about 1500 tons of peach processing residue is produced as a by-product per year, but it is discarded without any effective use.
  • a peach extract is produced by a specific combination of extraction solvents from fruit peaches that have been discarded without being effectively used, or peach processing residues, and by-products are effectively used. It is very specific in terms.
  • peaches containing the flesh and fruit skins from which the seeds have been removed from these fruit peaches (young peaches) or mature peaches are required. If there is, it can be used as a raw material for extraction after pre-freezing, finely pulverizing with a mixer or the like, and dried by hot air drying, reduced pressure drying, or reduced pressure drying.
  • the primary extraction solvent used in the production of a peach extract from these peach raw materials provided by the present invention is characterized in that ethanol alone or an ethanol / hexane mixture is used.
  • the peach extraction solvent disclosed in Patent Document 2 is a mixed solvent having a 1: 1 volume ratio of chloroform / methanol, and the obtained glucosylceramide fraction (extract) contains chloroform or methanol having high toxicity. Residuals are feared, and it is not necessarily preferable.
  • ethanol and hexane used in food processing and fat processing are used, and the safety of the obtained extract is extremely high.
  • the amount of extraction solvent used for the peach raw material that is the raw material for extraction, but it is better to use it in a conversion of about 0.1 to 1 L with respect to 100 g of the peach fine powder or peach processing residue as the raw material.
  • the mixing ratio is 1 to 5 volumes, preferably 1 to 3 volumes of ethanol with respect to 1 volume of hexane.
  • the extraction temperature and time in this case are not particularly limited, but it is preferable to carry out the extraction at a temperature of about room temperature to 80 ° C. for about 0.1 to 24 hours.
  • the extraction process which is a method for producing the peach extract of the present invention
  • primary extraction is performed with ethanol alone or a mixture of ethanol / hexane.
  • hydrous ethanol can also be used.
  • a so-called primary extract extracted with ethanol alone or a mixed solution of ethanol / hexane is further subjected to partition extraction with hexane / water, so that A peach extract having an active oxygen scavenging ability and containing a glycosphingolipid (ceramide component) is obtained.
  • the volume ratio of the extraction liquid in the primary extraction and the hexane and water used for the partition extraction of the extraction liquid is 1: 0.5: 0.5 to 1: 2: 2.
  • the volume ratio of hexane and water in the hexane / water partition extraction with respect to the primary extract is 0.5 hexane. It is preferable that the amount be appropriately selected within the range of 0.5 to 2 volumes of water.
  • the degree of separation in partition extraction and the content of the ceramide component can be increased.
  • the emulsification is eliminated by treatment such as addition of salt, heating / cooling, or filtration using an inert carrier such as celite. It is known that it can be.
  • the adoption of these methods is also studied, and the emulsification is eliminated by treatment such as salting out, heating / cooling, or filtration with an inert carrier such as celite at a mixing ratio exhibiting an emulsified state. In some cases, it was possible.
  • the peach processing residue containing the fiber component obtained by removing seeds and juice from the young peach, mature peach, or young peach or mature peach to be extracted is used.
  • the pulverized and dried product can be degreased with hexane in advance, and this degreasing treatment reduces the lipid content in the peach extract, and as a result, the ceramide content ratio can be improved.
  • the extraction operation can be performed under moderate alkaline conditions, but the extraction operation under such alkaline conditions is not essential.
  • the extract has a high polyphenol content when extracted using ethanol alone as the extraction solvent. Therefore, the extraction conditions can be appropriately selected according to the intended use of the components contained in the extract, and in that respect, the method for producing a peach extract of the present invention is extremely specific. It can be said that there is.
  • the extract obtained by the above extraction treatment is concentrated under reduced pressure, and further dried under reduced pressure, whereby the peach extract targeted by the present invention can be obtained as a solid.
  • the peach extract thus produced contains ceramide (glycosphingolipid), polyphenol and glycoside, and has active oxygen scavenging ability due to the inclusion of the polyphenol and other antioxidant active substances.
  • the content of ceramide is high, and so-called “peach ceramide” can be efficiently applied to foods, cosmetics, quasi drugs, and processed products thereof.
  • the active oxygen scavenging ability is 5% or more as DPPH (diphenylpicrylhydrazyl) activity, and the ceramide content is 0.5% or more.
  • the peach extract is, for example, in the form of a powder mixed with cyclodextrin, or a solution dissolved in an aqueous solution, food, cosmetics, quasi drugs, and processed products thereof. Applies to
  • Test Example 1 Measurement of ceramide content
  • the ceramide content (purity) of the peach extract in the following examples was measured as follows. 1. As a measurement sample, a peach extract was dissolved in a chloroform / methanol (2: 1 v / v) mixed solution so as to be 20 mg / mL to obtain a sample solution. 2. For the standard product, use a matreya (USA) standard substance (purified soybean-derived product) and dissolve in a chloroform / methanol (2: 1 v / v) mixture so that the concentration is 2 mg / mL. Prepared as a standard solution. 3.
  • Test Example 2 Measurement of DPPH radical scavenging activity DPPH (diphenylpicrylhydrazyl) radical scavenging activity in the following Examples was measured as follows. 1. Each measurement sample was adjusted to 2 mg / mL with ethanol. 2. DPPH was adjusted to 0.4 mM with ethanol. 3. The measurement sample solution was prepared as follows. (1) Sample 2 mg / mL sample solution 2 mL mixed with DPPH solution 1 mL and ethanol 1 mL (2) Sample blank 2 mg / mL sample solution 2 mL mixed with ethanol 2 mL (3) Control 3 mL ethanol and DPPH solution 1 mL mixed (4) Control blank ethanol 4mL 4). After the measurement sample solution was prepared, the reaction was allowed to occur for 20 minutes while protected from light. After the reaction, the absorbance (OD) at 571 nm was measured with a spectrophotometer.
  • DPPH diphenylpicrylhydrazyl
  • Test Example 3 Content measurement of total polyphenols The content of total polyphenols in the following examples was measured as follows. 1. The measurement sample was adjusted to 10 mg / mL with 80% ethanol, and further diluted 10-fold with distilled water to 1.0 mg / mL. 2. A standard gallic acid was prepared as follows. 28ppm, 14ppm, 7ppm, 33.5ppm, 1.75ppm 3. A 10% aqueous sodium carbonate solution was prepared. 4). A 5-fold diluted phenol reagent was prepared with purified water. 5. 2 mL of 5-fold diluted phenol reagent and 2 mL of 10% aqueous sodium carbonate solution were added to 2 mL of each measurement sample, and the mixture was stirred and reacted for 1 hour. 6). The reaction solution was filtered and the absorbance was measured at 760 nm. 7). A calibration curve was prepared with gallic acid to determine the total polyphenol (total PP) content (mg / g).
  • Reference Example 1 Preparation of extract from peach processing residue by extraction with ethanol alone To 10 g of dried peach processing residue, 20 mL of 95% ethanol was added and extracted with stirring at 42 ° C for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, while the extraction residue was again extracted in the same manner to obtain an extract. Both extracts were combined, concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 1.17 g of an orange solid.
  • Reference Example 2 Production of extract from peach processing residue by extraction with hexane alone 60 mL of hexane was added to 60 g of dried peach processing residue, followed by extraction (defatting) at 60 ° C. for 2 hours with stirring operation. The extract was filtered under reduced pressure, and 60 mL of hexane was used for eviction. The obtained filtrate was concentrated under reduced pressure, and the residue was dried under reduced pressure to obtain 0.3 g of a yellow starch candy.
  • Example 1 Production of extract from fruit peach (young peach) ⁇ Extraction solvent: ethanol alone, hexane / water partition extraction with alkali treatment> Frozen fruit peach (young peach) was thawed for 15 minutes in a microwave oven, finely pulverized with a mixer, and dried. To 50 g of this powder, 300 mL of 95% ethanol (containing 9.6 g of sodium hydroxide) and 37.5 mL of purified water were added and extracted at 42 ° C. for 30 minutes with stirring. The extract was filtered under reduced pressure, 300 mL of hexane and 150 mL of purified water were added to the filtrate, and the mixture was extracted by partitioning. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 160.7 mg of a green solid.
  • extraction solvent ethanol alone, hexane / water partition extraction with alkali treatment>
  • Example 2 Production of extract from fruit peach (young peach) ⁇ Extraction solvent: ethanol alone, hexane / water partition extraction, no alkali treatment> Frozen fruit peach (young peach) was thawed for 15 minutes in a microwave oven, finely pulverized with a mixer, and dried. 50 g of this powder was added with 300 mL of 95% ethanol and 37.5 mL of purified water, and extracted at 42 ° C. for 30 minutes with stirring. The extract was filtered under reduced pressure, 300 mL of hexane and 150 mL of purified water were added to the filtrate, and the mixture was extracted by partitioning. The hexane layer was collected, the solvent was concentrated under reduced pressure with an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 486.0 mg of a green solid.
  • Example 3 Production of extract from peach processing residue ⁇ After degreasing process Extraction solvent: Ethanol alone, hexane / water partition extraction>
  • the squeezed rice cake (peach processed residue) after producing peach juice was dried, and 800 mL of hexane was added to 200 g of the peach processed residue, followed by stirring at 70 ° C. for 4 hours for degreasing treatment.
  • the peach processing residue after the degreasing treatment was recovered by filtration under reduced pressure. 800 mL of 95% ethanol was added to the resulting defatted peach processed residue, extracted at 70 ° C. for 60 minutes, and filtered under reduced pressure to obtain an extract.
  • the extraction residue was treated again in the same manner to obtain an extract.
  • Example 4 Production of extract from peach processing residue ⁇ Extraction solvent: ethanol alone, hexane / water partition extraction with alkali treatment> To 100 g of the dried peach processing residue, 200 mL of 95% ethanol (containing 6.4 g of sodium hydroxide) and 25 mL of purified water were added, and the mixture was extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, and the extraction residue was similarly treated again to obtain an extract. Both extracts were combined, 400 mL of hexane and 200 mL of purified water were added, and the mixture was stirred and distributed for 1 hour. The hexane layer was collected, the solvent was concentrated under reduced pressure with an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 131.3 mg of an orange solid.
  • extraction solvent ethanol alone, hexane / water partition extraction with alkali treatment>
  • Example 5 Preparation of extract from peach processing residue ⁇ Extraction solvent: ethanol alone, hexane / water partition extraction, no alkali treatment> To 100 g of the undried peach processing residue, 200 mL of 95% ethanol and 25 mL of purified water were added, and extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, and the extraction residue was similarly treated again to obtain an extract. Both extracts were combined, 400 mL of hexane and 200 mL of purified water were added, and the mixture was stirred and distributed for 1 hour. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 172.1 mg of an orange solid.
  • extraction solvent ethanol alone, hexane / water partition extraction, no alkali treatment>
  • Example 6 Preparation of extract from peach processing residue ⁇ Extraction solvent: Ethanol / hexane mixture hexane / water partition extraction> To 100 g of the undried peach processing residue, 200 mL of 95% ethanol, 100 mL of hexane and 25 mL of purified water were added, and the mixture was extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, and 100 mL of hexane and 100 mL of purified water were added to the filtrate, and the mixture was stirred at 42 ° C. for 1 hour and partitioned and extracted with hexane / water. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 177.8 mg of an orange solid.
  • extraction solvent Ethanol / hexane mixture hexane / water partition extraction>
  • Example 7 Preparation of extract from peach processing residue ⁇ Extraction solvent: ethanol alone, hexane / water partition extraction> To 50 g of the dried peach processing residue, 200 mL of 95% ethanol was added, and extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure, and 50 mL of 95% ethanol was used to drive out the extract. The residue was extracted again in the same manner, filtered under reduced pressure, and expelled. 150 mL of hexane was added to the combined filtrate (150 mL) and stirred for 30 minutes, and then 150 mL of distilled water was added and stirred for 30 minutes to perform partition extraction with hexane / water. The hexane layer was collected and concentrated under reduced pressure, and the residue was dried under reduced pressure to obtain 3.85 g of an orange-colored starch candy as an extract.
  • extraction solvent ethanol alone, hexane / water partition extraction>
  • Example 8 Examination of partition extraction conditions of hexane / water for peach raw material extract Extraction of hexane / water to a primary extract obtained by degreasing a dried peach processed residue with hexane and extracting with 95% ethanol The ratio of the solvent capacity was examined at the solvent ratio (primary extract: hexane: water) described in Table 1 below. The primary extract was added to the test tube, then hexane was added and shaken vigorously for 10 seconds, then water was added, shaken vigorously again for 10 seconds, and then allowed to stand to examine the state of separation of the solution.
  • a peach extract having an active oxygen scavenging ability could be efficiently obtained by using a specific extraction method from a peach raw material according to the present invention.
  • the obtained extract has not only active oxygen scavenging ability but also contains peach ceramide, and is highly safe in that ethanol and hexane are used as the extraction solvent.
  • peach ceramide contains peach ceramide, and is highly safe in that ethanol and hexane are used as the extraction solvent.
  • a peach extract containing ceramide (glycosphingolipid), glycoside, and polyphenol and having active oxygen scavenging ability can be produced from peach by a safe extraction method.
  • the peach extract obtained by the present invention can obtain a peach extract in which the content of the target component is changed by various combinations of extraction solvents used for the extraction, for example, the content of peach ceramide
  • the raw material is a peach processing residue generated from processing processes such as fruit peach (young peach) or peach juice produced in the peach production process, It is extremely specific in that by-products can be used effectively.

Abstract

The purpose of the present invention is to provide a peach extract obtained from peaches, said peach extract having an active oxygen-scavenging ability, and a highly safe method for producing the same. Provided is a peach extract having an active oxygen-scavenging ability that is obtained by: extracting a starting peach material with ethanol or an ethanol/hexane mixture, said starting peach material comprising picked peaches (young peaches), matured peaches or a residue that is obtained from processing of peaches and contains fiber components remaining after removing seeds and juice from picked peaches or matured peaches; and partition extracting the thus obtained primary extract with hexane/water. The peach extract contains ceramides (sphingo glycolipids) and polyphenols. Also provided is a method for producing the peach extract. The peach extract obtained in the present invention is usable as foods, cosmetics, quasi-drugs and processed products thereof.

Description

桃抽出物及びその製造方法Peach extract and method for producing the same
　本発明は、活性酸素消去能を有し、且つスフィンゴ糖脂質（セラミド成分）を含有する桃抽出物、及びその製造方法に関する。 The present invention relates to a peach extract having active oxygen scavenging ability and containing glycosphingolipid (ceramide component), and a method for producing the same.
　最近、安全性の面から天然成分由来の素材についての研究が行われており、種々の有効な生理活性を有する植物抽出物が提案されてきている。
　本発明者等も植物油脂、特に米の糠を原料とした食用こめ油の製造過程で生成される副産物に含まれる有用微量成分に着目し、検討を行い、その結果、コメセラミドの抽出製造法を確立し、天然由来のコメセラミド（スフィンゴ糖脂質）を提供してきている。
　本発明者等が提供するコメセラミドは、天然素材由来のセラミドであり、その安全性は高いものであり、またその純度も極めて高く、これまでに食品、化粧品、或いは医薬部外品、及びそれらの加工品の素材として広く利用されてきている。 Recently, studies on materials derived from natural ingredients have been conducted from the viewpoint of safety, and plant extracts having various effective physiological activities have been proposed.
The present inventors also focused on useful trace components contained in by-products produced in the production process of edible rice bran oil made from vegetable oil and fat, especially rice bran, and as a result, a method for extracting and producing rice ceramide And has been providing naturally derived rice ceramide (sphingoglycolipid).
The rice ceramide provided by the present inventors is a ceramide derived from a natural material, and its safety is high and its purity is extremely high, so far, food, cosmetics, quasi drugs, and those It has been widely used as a material for processed products.
　セラミドは、スフィンゴ脂質の一種であり、長鎖アミノアルコールであるスフィンゴシンと脂肪酸とがアミド結合した化合物群の総称である。このセラミドは、細胞膜に高濃度で存在することが知られており、特に、皮膚の角質細胞間脂質の主成分として存在し、皮膚内部からの水分の蒸発を防止する保湿能としてのバリア機能を担っている。
　しかしながら、加齢と共に角質細胞間脂質中のセラミドが減少し、保湿能が衰退することから、乾燥肌、シワ、或いは肌荒れの原因となることが報告されている。 Ceramide is a kind of sphingolipid and is a generic name for a group of compounds in which sphingosine, which is a long-chain amino alcohol, and an fatty acid are amide-bonded. This ceramide is known to exist in high concentrations in the cell membrane, and in particular, it exists as a main component of the skin keratinocyte lipid, and has a barrier function as a moisturizing function that prevents evaporation of moisture from inside the skin. I'm in charge.
However, it has been reported that ceramide in keratinocyte lipids decreases with aging and moisturizing ability declines, causing dry skin, wrinkles, or rough skin.
　また、皮膚の老化に限らず、アトピー性皮膚炎によって起こる肌のカサつき、肌荒れなどの要因として、セラミドが不足していることが報告されている。すなわち、アトピー性皮膚炎における乾燥肌は、もともとセラミドが少ないという特徴があり、皮膚のバリア機能の低下に伴い、皮膚内部から外部へ水分が失われやすくなり、皮膚がカサカサと乾燥して、抗原や化学物質が皮膚内部に入りやすく、その結果アレルギー反応が起こり、かゆみや炎症などの様々な症状を呈することが報告されている。 In addition, it is reported that ceramide is insufficient as a cause of not only skin aging but also skin roughness and rough skin caused by atopic dermatitis. That is, dry skin in atopic dermatitis is originally characterized by low ceramide, and as the barrier function of the skin decreases, moisture tends to be lost from the inside of the skin to the outside. It has been reported that chemicals and chemicals can easily enter the skin, resulting in allergic reactions and various symptoms such as itching and inflammation.
　このように、皮膚におけるセラミド含量は、皮膚の健康状態の一つの指標とされており、不足したセラミドの補充が肌の保湿効果、或いは美白効果に有効であるとされ、セラミドは化粧品原料としてその需要が高まり、また、アトピー性皮膚炎症状を緩和する機能性食品として広く利用されるに至っている。
　さらにまた、セラミドには免疫賦活作用、抗腫瘍効果等も確認されており、今後ますますその需要が高まるものといえる。 Thus, the content of ceramide in the skin is regarded as one index of the health condition of the skin, and supplementation of insufficient ceramide is effective for the moisturizing effect or whitening effect of the skin, and ceramide is used as a cosmetic raw material. The demand has increased, and it has been widely used as a functional food for alleviating atopic skin inflammation.
Furthermore, ceramide has been confirmed to have an immunostimulatory effect, an antitumor effect, and the like, and it can be said that its demand will increase further in the future.
　ところで、最近に至り、種々の果実、或いは野菜等、植物由来のセラミド成分の研究が種々検討されてきている（特許文献１）。そのなかでも、桃にはセラミドの含有量が多いとされており、桃からセラミドを抽出する技術が提案されている（特許文献２）。
　この桃の含有成分については、セラミド抽出のみならず、桃果実自体についての生理活性の検討も行われており、桃果実に含まれるポリフェノール、桃自体の活性酸素消去機能等の検討も報告されている（非特許文献１～３）。 By the way, recently, various studies on plant-derived ceramide components such as various fruits or vegetables have been studied (Patent Document 1). Among them, peach is said to have a high content of ceramide, and a technique for extracting ceramide from peach has been proposed (Patent Document 2).
Regarding the peach content, not only ceramide extraction but also the physiological activity of the peach fruit itself has been studied, and the polyphenol contained in the peach fruit and the active oxygen scavenging function of the peach itself have also been reported. (Non-Patent Documents 1 to 3).
　上記した特許文献２に記載される桃からセラミドの抽出は、抽出溶媒としてクロロホルム／メタノール混液を用いた抽出方法によるグルコシルセラミド画分の調製であり、抽出溶媒として用いるクロロホルム及びメタノールの毒性を考慮した場合、安全性の面から好ましいものとはいえない。
　したがって、より安全性が確保できる桃からのセラミドの抽出方法の検討が要求されている。 The extraction of ceramide from peach described in Patent Document 2 described above is the preparation of a glucosylceramide fraction by an extraction method using a chloroform / methanol mixture as an extraction solvent, taking into account the toxicity of chloroform and methanol used as the extraction solvent. In this case, it is not preferable from the viewpoint of safety.
Therefore, examination of the extraction method of the ceramide from the peach which can ensure more safety is requested | required.
　これまで提案されている、種々の果実、野菜等の植物成分からセラミド成分を抽出・製造する技術としては、例えば、ブドウ、サクランボ、小麦、米、大豆等の植物原料からアルコール系溶媒（例えば、エタノール）により抽出する方法（特許文献１）、ツバキ絞り粕をヘキサンにより脱脂・前処理したのち、エタノールで抽出する方法（特許文献３）、米糠を水、エタノール、アセトン、ヘキサンから選択される２種以上の混合溶媒を用いて抽出する方法（特許文献４）、小麦、大豆、トウモロコシ、米糠等の植物原料をアルカリ性エタノール溶媒で加水分解したのち、ヘキサン、アセトン、及び水の混合溶媒による抽出方法（特許文献５及び特許文献６）などが知られている。 Examples of techniques for extracting and producing ceramide components from plant components such as various fruits and vegetables that have been proposed so far include, for example, alcohol-based solvents (for example, grapes, cherries, wheat, rice, soybeans, etc.) 2) selected from water, ethanol, acetone, hexane, and a method of extracting the rice bran with ethanol after degreasing and pretreating the camellia rice cake with hexane (Patent Document 1) Extraction method using a mixed solvent of at least seeds (Patent Document 4), after hydrolyzing plant materials such as wheat, soybeans, corn, rice bran, etc. with an alkaline ethanol solvent, extraction method using a mixed solvent of hexane, acetone, and water (Patent Document 5 and Patent Document 6) are known.
　本発明者らも、桃からセラミド成分を抽出するべく上記した各特許文献に記載の抽出方法を試みたが、満足するものではなかった。そこで、かかる現状を鑑み、桃からセラミド成分を効率良く安全に抽出する方法を検討した結果、桃原料をエタノール、又はエタノール／ヘキサン混液で抽出を行い、得られた抽出液を更にヘキサン／水により分配抽出することにより、活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有する桃抽出物が効率よく得られることを新規に見出し、本発明を完成させるに至った。 The present inventors also tried the extraction methods described in the above-mentioned patent documents in order to extract the ceramide component from peach, but were not satisfied. Therefore, in view of the present situation, as a result of examining a method for efficiently and safely extracting a ceramide component from peach, the peach raw material was extracted with ethanol or an ethanol / hexane mixture, and the obtained extract was further diluted with hexane / water. It has been found that a peach extract having an active oxygen scavenging ability and containing a glycosphingolipid (ceramide component) can be efficiently obtained by partition extraction, and the present invention has been completed.
特許第４１０８０６９号掲載公報Japanese Patent No. 4108069 特許第４７２３６３０号掲載公報Patent No. 4723630 publication 特開２００７－３０８４２４号公報JP 2007-308424 A 特開平１１－２７９５８６号公報JP 11-279586 A 特開２００２－３００９３号公報Japanese Patent Laid-Open No. 2002-30093 特開２００６－２３２６９９号公報JP 2006-232699 A
　したがって本発明は、桃から得られる活性酸素消去能を有する桃抽出物を、効率良く安全に抽出する方法、及び該製造方法により得られた活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有する桃抽出物を提供することを課題とする。 Therefore, the present invention provides a method for efficiently and safely extracting a peach extract having active oxygen scavenging ability obtained from peaches, and a method for extracting active peaches obtained by the production method, and a glycosphingolipid ( It is an object to provide a peach extract containing a ceramide component).
　かかる課題を解決するための本発明は、その基本的態様として、摘果桃、成熟桃、又は摘果桃若しくは成熟桃から種子及び果汁を取り除いた繊維成分を含む桃加工残渣を、エタノール、又はエタノール／ヘキサン混液で抽出し、該抽出液を、さらにヘキサン／水により分配抽出することにより得られた活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有することを特徴とする桃抽出物である。 As a basic aspect of the present invention for solving such a problem, a peach processed peach, mature peach, or a processed peach residue containing fiber components obtained by removing seeds and fruit juice from the extracted peach or mature peach, ethanol, or ethanol / A peach characterized by being extracted with a hexane mixed solution, and having an active oxygen scavenging ability obtained by further partitioning and extracting the extract with hexane / water and containing a glycosphingolipid (ceramide component) It is an extract.
　より具体的には、本発明は、上記活性酸素消去能が、ＤＰＰＨ（ジフェニルピクリルヒドラジル）活性である桃抽出物である。 More specifically, the present invention is a peach extract whose active oxygen scavenging ability is DPPH (diphenylpicrylhydrazyl) activity.
　もっとも具体的には、本発明は、ＤＰＰＨ活性が５％以上であり、セラミド含有量が０．５％以上である桃抽出物である。 Most specifically, the present invention is a peach extract having a DPPH activity of 5% or more and a ceramide content of 0.5% or more.
　また本発明は、別の態様として、活性酸素消去能を有し、且つ、スフィンゴ脂質（セラミド成分）を含有する桃抽出物の製造方法であり、具体的には、摘果桃、成熟桃、又は摘果桃若しくは成熟桃から種子及び果汁を取り除いた繊維成分を含む桃加工残渣をエタノール、又はエタノール／ヘキサン混液で抽出して、得られた抽出液を、さらにヘキサン／水により分配抽出することを特徴とする活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有する桃抽出物の製造方法である。 In another aspect, the present invention is a method for producing a peach extract having active oxygen scavenging ability and containing a sphingolipid (ceramide component), specifically, a fruit peach, a mature peach, or Peach processing residue containing fiber components obtained by removing seeds and fruit juice from plucked peach or mature peach is extracted with ethanol or ethanol / hexane mixture, and the resulting extract is further partitioned and extracted with hexane / water And a method for producing a peach extract containing a sphingoglycolipid (ceramide component).
　より具体的には、本発明は、桃加工残渣の抽出に用いる抽出液と、抽出液の分配抽出に用いるヘキサン及び水の容量比が、１：０．５：０．５～１：２：２である桃抽出物、及びその製造方法である。 More specifically, in the present invention, the volume ratio of the extract used for extracting the peach processing residue and the hexane and water used for the partition extraction of the extract is 1: 0.5: 0.5 to 1: 2: 2 is a peach extract, and a production method thereof.
　更に本発明は、上記した桃抽出物を含む食品、化粧品、或いは医薬部外品、及びそれらの加工品である。 Furthermore, the present invention is a food, cosmetic or quasi drug containing the peach extract described above, and a processed product thereof.
　さらに具体的には、本発明は、上記した物抽出物をシクロデキストリンと混合した粉末状物、或いは水溶液の状態とした食品、化粧品、或いは医薬部外品、及びそれらの加工品である。 More specifically, the present invention is a powdery product obtained by mixing the above-mentioned extract with cyclodextrin, or a food, cosmetic, quasi-drug, or processed product thereof in the form of an aqueous solution.
　本発明により、安全性に優れた、比較的簡便な方法により、桃原料より効率よく活性酸素消去能を有する桃抽出物を得ることができる。
　本発明が提供する桃抽出物の製造方法は、桃原料に対する、エタノール、又はエタノール／ヘキサン混液による抽出液、すなわち、いわゆる一次抽出液を、さらにヘキサン／水で分配抽出する点で、これまで何ら検討されていなかった製造方法であり、極めて特異的なものである。
　その結果、かくして製造された桃抽出物は、セラミド（スフィンゴ糖脂質）、ポリフェノール及び配糖体を含有するものであり、活性酸素消去能を有し、安全性が高く、食品、化粧品、或いは医薬部外品、及びそれらの加工品の素材として極めて有用性の高いものである。 According to the present invention, a peach extract having active oxygen scavenging ability can be obtained more efficiently than a peach raw material by a relatively simple method with excellent safety.
The method for producing a peach extract provided by the present invention is not limited to the point that an extract of ethanol or an ethanol / hexane mixture, ie, a so-called primary extract, is further partitioned and extracted with hexane / water. This is a manufacturing method that has not been studied and is extremely specific.
As a result, the peach extract thus produced contains ceramide (sphingoglycolipid), polyphenol and glycoside, has active oxygen scavenging ability, high safety, food, cosmetics or pharmaceuticals. It is extremely useful as a raw material for quasi-drugs and processed products.
　上記したとおり、本発明は、桃原料である摘果桃、成熟桃、又は摘果桃若しくは成熟桃から種子及び果汁を取り除いた繊維成分を含む桃加工残渣を、エタノール、又はエタノール／ヘキサン混液で抽出し、該抽出液を、さらにヘキサン／水により分配抽出することにより得られた活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有することを特徴とする桃抽出物である。
　原料となる摘果桃とは、桃の生産過程における剪定による摘果桃（若桃）であり、成熟桃とは、桃として市場に出荷されるに適した桃である。
　また、桃加工残渣とは、摘果桃（若桃）若しくは成熟桃から種子および果汁を取り除いた繊維成分を含む桃加工残渣である。 As described above, the present invention extracts a peach processed residue containing a fiber component obtained by removing seeds and fruit juice from a fruit peach, mature peach, or fruit peach or mature peach, which is a peach raw material, with ethanol or an ethanol / hexane mixture. A peach extract characterized by having an active oxygen scavenging ability obtained by further partitioning and extracting the extract with hexane / water and containing a glycosphingolipid (ceramide component).
The fruit peach used as a raw material is a fruit peach (young peach) by pruning in the peach production process, and the mature peach is a peach suitable for being shipped to the market as a peach.
Moreover, a peach processing residue is a peach processing residue containing the fiber component which remove | eliminated the seed and fruit juice from picked peach (young peach) or mature peach.
　桃の収穫量は全国で年間約１５万トンであり、その収穫過程で生じる摘果桃（若桃）は、桃収穫量の約１０％となる約１．５万トンといわれている。この摘果桃は、そのごく一部が漬物などの食品用として加工されているが、大半は処理されることなくそのままの形で肥料として桃栽培農場（桃農園）に撒き使用されており、その有効利用としての手段はなかった。
　一方、桃の果汁（桃ジュース）等の加工企業からは、年間１５００トン程度の桃加工残渣が副産物として生じるが、何ら有効利用されることなく廃棄されている。 The peach harvest is about 150,000 tons annually nationwide, and the fruit peach (young peach) produced during the harvesting process is said to be about 15,000 tons, which is about 10% of the peach harvest. A small part of this fruit peach is processed for food such as pickles, but most of it is used as fertilizer as it is without being processed. There was no means for effective use.
On the other hand, from processing companies such as peach fruit juice (peach juice), about 1500 tons of peach processing residue is produced as a by-product per year, but it is discarded without any effective use.
　本発明にあっては、これら有効使用されることなく廃棄されていた摘果桃、或いは桃加工残渣から、抽出溶媒の特異的な組合せにより桃抽出物を製造するものであり、副産物を有効利用する点で、極めて特異的なものである。 In the present invention, a peach extract is produced by a specific combination of extraction solvents from fruit peaches that have been discarded without being effectively used, or peach processing residues, and by-products are effectively used. It is very specific in terms.
　抽出原料となる桃原料として、摘果桃（若桃）、又は成熟桃を使用する場合には、これら摘果桃（若桃）若しくは成熟桃から種子を取り除いた果肉及び果皮を含む桃を、必要であれば予め凍結して、それぞれミキサー等で細かく粉砕し、温風乾燥、或いは減圧乾燥、若しくは減圧乾燥により乾燥させたものを、抽出用の原料として使用することができる。
　また、抽出原料となる桃原料として、摘果桃若しくは成熟桃から種子および果汁を取り除いた繊維成分を含む桃加工残渣を使用する場合には、桃の果汁等の加工工程から副産物として生じる桃加工残渣（いわゆる、桃パルプ）を、上記と同様の方法により乾燥し、抽出用の原料として使用することができる。
　もちろん、桃の果汁等の加工工程から副産物として生じる桃加工残渣を、乾燥することなく抽出用原料としても良いことは、いうまでもない。 When using fruit peaches (young peaches) or mature peaches as peach raw materials to be extracted, peaches containing the flesh and fruit skins from which the seeds have been removed from these fruit peaches (young peaches) or mature peaches are required. If there is, it can be used as a raw material for extraction after pre-freezing, finely pulverizing with a mixer or the like, and dried by hot air drying, reduced pressure drying, or reduced pressure drying.
In addition, when using peach processing residue containing fiber components obtained by removing seeds and fruit juice from extracted peach or mature peach as a peach raw material as an extraction raw material, the peach processing residue generated as a by-product from processing processes such as peach juice (So-called peach pulp) can be dried by the same method as described above and used as a raw material for extraction.
Of course, it goes without saying that a peach processing residue generated as a by-product from a processing step such as peach juice may be used as a raw material for extraction without drying.
　本発明が提供する、これらの桃原料から桃抽出物の製造に使用する一次抽出溶媒としては、エタノール単独、又はエタノール／ヘキサン混液を使用することに特徴を有するものである。
　特許文献２に開示される桃の抽出溶媒は、クロロホルム／メタノールの１：１の体積比率による混合溶媒であり、得られたグルコシルセラミド画分（抽出物）には、毒性の強いクロロホルム或いはメタノールの残留が懸念され、必ずしも好ましいものとはいえない。
　これに対して本発明では、食品加工や油脂加工で用いられるエタノール及びヘキサンを使用するものであって、得られた抽出物の安全性は極めて高いものとなる。
　一次抽出溶媒としては、エタノールまたはエタノール／ヘキサンのほかに、メタノール、プロパノール、イソプロパノール、ブタノール、イソブタノールなどの水と混和する低級アルコール類や、アセトンなどを単独で、或いはこれらの溶媒同士の混合液、或いはこれらの溶媒とヘキサンとの混液として使用することができる。 The primary extraction solvent used in the production of a peach extract from these peach raw materials provided by the present invention is characterized in that ethanol alone or an ethanol / hexane mixture is used.
The peach extraction solvent disclosed in Patent Document 2 is a mixed solvent having a 1: 1 volume ratio of chloroform / methanol, and the obtained glucosylceramide fraction (extract) contains chloroform or methanol having high toxicity. Residuals are feared, and it is not necessarily preferable.
On the other hand, in the present invention, ethanol and hexane used in food processing and fat processing are used, and the safety of the obtained extract is extremely high.
As primary extraction solvent, in addition to ethanol or ethanol / hexane, lower alcohols miscible with water such as methanol, propanol, isopropanol, butanol, isobutanol, acetone, etc. alone or a mixture of these solvents Alternatively, it can be used as a mixture of these solvents and hexane.
　抽出用原料である桃原料に対する抽出溶媒の使用量は特に制限はないが、原料である桃の微粉末、或いは桃加工残渣１００ｇに対して０．１～１Ｌ程度の換算で使用するのがよい。
　また、エタノール／ヘキサン混液による抽出の場合、その混合比は、ヘキサン１容量に対して、エタノールを１～５容量、好ましくは１～３容量とするのがよい。
　この場合の抽出温度、時間は特に制限はないが、室温～８０℃程度の温度で、０．１～２４時間程度で行うのがよい。 There is no particular limitation on the amount of extraction solvent used for the peach raw material that is the raw material for extraction, but it is better to use it in a conversion of about 0.1 to 1 L with respect to 100 g of the peach fine powder or peach processing residue as the raw material. .
In the case of extraction with an ethanol / hexane mixture, the mixing ratio is 1 to 5 volumes, preferably 1 to 3 volumes of ethanol with respect to 1 volume of hexane.
The extraction temperature and time in this case are not particularly limited, but it is preferable to carry out the extraction at a temperature of about room temperature to 80 ° C. for about 0.1 to 24 hours.
　上記したように、本発明の桃抽出物の製造方法である抽出工程においては、エタノール単独、或いはエタノール／ヘキサンの混液で一次抽出を行う。エタノール単独抽出においては、含水エタノールを用いることもできる。
　本発明の桃抽出物の製造方法にあっては、エタノール単独、或いはエタノール／ヘキサンの混液で抽出したいわゆる一次抽出液を、さらにヘキサン／水で分配抽出を行うことにより、ヘキサン溶液層から目的とする活性酸素消去能を有し、且つスフィンゴ糖脂質（セラミド成分）を含有する桃抽出物を得る。 As described above, in the extraction process, which is a method for producing the peach extract of the present invention, primary extraction is performed with ethanol alone or a mixture of ethanol / hexane. In ethanol extraction alone, hydrous ethanol can also be used.
In the method for producing a peach extract of the present invention, a so-called primary extract extracted with ethanol alone or a mixed solution of ethanol / hexane is further subjected to partition extraction with hexane / water, so that A peach extract having an active oxygen scavenging ability and containing a glycosphingolipid (ceramide component) is obtained.
　本発明者らの検討によれば、一次抽出における抽出液と、抽出液の分配抽出に用いるヘキサン及び水の容量比が、１：０．５：０．５～１：２：２であるのが好ましいものであることが判明した（後記する実施例を参照）。
　したがって、一次抽出で使用した抽出液（エタノール単独、或いはエタノール／ヘキサン混液）を１容量とした場合に、一次抽出液に対するヘキサン／水の分配抽出におけるヘキサンと水の容量比は、ヘキサン０．５～２容量であり、水０．５～２容量の範囲内で適宜選択するのがよい。
　この容量比率で一次抽出液、ヘキサン／水の分配抽出を行うことにより、分配抽出における分離度、並びにセラミド成分の含有率を高めることができる。
　一般的に、有機層と水層が分離せず、乳化状態を呈した場合、塩の添加や加温・冷却、或いはセライトなどの不活性担体を用いた濾過などの処理により、乳化を解消させることができることが知られている。本発明においても、当然それらの方法の採用も検討され、乳化状態を呈した混合比において、塩析や、加温・冷却、或いはセライトなどの不活性担体による濾過などの処理により乳化を解消することができたケースが認められた。
　しかしながら、塩の添加やセライト濾過などの処理においては、抽出物中に塩や担体の混入が避けられない。また、加温・冷却などの方法は、温度管理や時間管理など処理工程が煩雑になるうえ、必ずしも分離が保証されない場合が多い。
　一方、本発明の溶媒比においては、混合後、放置するのみで、効率よく分離される。
　この一次抽出液に対するヘキサン／水による分配抽出、その溶媒比率は、本発明者らの検討の結果新規に見出されたものであり、その点で極めて特異的なものである。
　また、このヘキサン／水の分配抽出で得たヘキサン溶液層を、所望により、例えば活性炭処理や、クロマトグラフ処理などを行い、抽出物の精製度をより高めることもできる。 According to the study by the present inventors, the volume ratio of the extraction liquid in the primary extraction and the hexane and water used for the partition extraction of the extraction liquid is 1: 0.5: 0.5 to 1: 2: 2. Was found to be preferred (see Examples below).
Therefore, when the volume of the extract used in the primary extraction (ethanol alone or ethanol / hexane mixture) is 1 volume, the volume ratio of hexane and water in the hexane / water partition extraction with respect to the primary extract is 0.5 hexane. It is preferable that the amount be appropriately selected within the range of 0.5 to 2 volumes of water.
By performing partition extraction of the primary extract and hexane / water at this volume ratio, the degree of separation in partition extraction and the content of the ceramide component can be increased.
Generally, when an organic layer and an aqueous layer are not separated and present in an emulsified state, the emulsification is eliminated by treatment such as addition of salt, heating / cooling, or filtration using an inert carrier such as celite. It is known that it can be. In the present invention, of course, the adoption of these methods is also studied, and the emulsification is eliminated by treatment such as salting out, heating / cooling, or filtration with an inert carrier such as celite at a mixing ratio exhibiting an emulsified state. In some cases, it was possible.
However, in the treatment such as addition of salt or filtration with celite, it is inevitable that salt or carrier is mixed in the extract. In addition, methods such as heating and cooling have complicated processing steps such as temperature management and time management, and separation is not always guaranteed.
On the other hand, in the solvent ratio of the present invention, the mixture is efficiently separated by simply leaving it after mixing.
The partition extraction with hexane / water and the solvent ratio of the primary extract are newly found as a result of the study by the present inventors, and are extremely specific in that respect.
In addition, the hexane solution layer obtained by this hexane / water partition extraction can be subjected to, for example, activated carbon treatment or chromatographic treatment to further increase the degree of purification of the extract.
　なお、本発明の桃抽出物の製造方法である抽出手段においては、抽出対象である若桃、成熟桃、又は若桃若しくは成熟桃から種子および果汁を取り除いた繊維成分を含む桃加工残渣の微粉砕乾燥物を、予めヘキサンにより脱脂処理をすることもでき、この脱脂処理により桃抽出物中の脂質含量が少なくなり、その結果セラミドの含有比率を向上させることができる。 In the extraction means, which is a method for producing a peach extract of the present invention, the peach processing residue containing the fiber component obtained by removing seeds and juice from the young peach, mature peach, or young peach or mature peach to be extracted is used. The pulverized and dried product can be degreased with hexane in advance, and this degreasing treatment reduces the lipid content in the peach extract, and as a result, the ceramide content ratio can be improved.
　また、上記の一次抽出操作においては、適度なアルカリ条件下で抽出操作を行うこともできるが、かかるアルカリ条件での抽出操作は、必須のものではない。 Further, in the primary extraction operation described above, the extraction operation can be performed under moderate alkaline conditions, but the extraction operation under such alkaline conditions is not essential.
　更にまた、抽出溶媒としてエタノール単独溶媒として用いて抽出した場合には、抽出物にはポリフェノールの含有量が多いことが判明した。
　したがって、目的とする抽出物の含有成分の如何による用途に応じて、抽出条件を適宜選択できるものであって、その点で、本発明の桃抽出物の製造方法は、極めて特異的なものであるといえる。 Furthermore, it has been found that the extract has a high polyphenol content when extracted using ethanol alone as the extraction solvent.
Therefore, the extraction conditions can be appropriately selected according to the intended use of the components contained in the extract, and in that respect, the method for producing a peach extract of the present invention is extremely specific. It can be said that there is.
　上記の抽出処理により得られた抽出エキスを、減圧下に濃縮し、更に減圧乾燥することにより固形物として、本発明が目的とする桃抽出物を得ることができる。
　かくして製造された桃抽出物には、セラミド（スフィンゴ糖脂質）、ポリフェノール及び配糖体などが含有されており、そのポリフェノール及びその他の抗酸化活性物質の含有により活性酸素消去能を有するものであり、また、セラミドの含有量も高く、いわゆる「桃セラミド」として、食品、化粧品、或いは医薬部外品、及びそれらの加工品に効率良く応用できるものである。 The extract obtained by the above extraction treatment is concentrated under reduced pressure, and further dried under reduced pressure, whereby the peach extract targeted by the present invention can be obtained as a solid.
The peach extract thus produced contains ceramide (glycosphingolipid), polyphenol and glycoside, and has active oxygen scavenging ability due to the inclusion of the polyphenol and other antioxidant active substances. In addition, the content of ceramide is high, and so-called “peach ceramide” can be efficiently applied to foods, cosmetics, quasi drugs, and processed products thereof.
　特に本発明が提供する桃抽出物にあっては、活性酸素消去能が、ＤＰＰＨ（ジフェニルピクリルヒドラジル）活性として５％以上であり、セラミド含有量が０．５％以上である。
　この桃抽出物は、より具体的には、例えば、シクロデキストリンと混合した粉末状物、或いは水溶液中に溶解させた溶液の状態として、食品、化粧品、或いは医薬部外品、及びそれらの加工品に適用される。 In particular, in the peach extract provided by the present invention, the active oxygen scavenging ability is 5% or more as DPPH (diphenylpicrylhydrazyl) activity, and the ceramide content is 0.5% or more.
More specifically, the peach extract is, for example, in the form of a powder mixed with cyclodextrin, or a solution dissolved in an aqueous solution, food, cosmetics, quasi drugs, and processed products thereof. Applies to
　以下に、本発明の桃抽出物の具体的製造方法を、実施例として記載することにより、本発明を更に詳細に説明していくが、本発明はこれらの実施例に限定されるものではなく、本発明の技術的思想を逸脱しない範囲での種々の変更は可能である。 Hereinafter, the present invention will be described in more detail by describing the specific production method of the peach extract of the present invention as examples, but the present invention is not limited to these examples. Various modifications can be made without departing from the technical idea of the present invention.
試験例１：セラミドの含有量測定
　以下の実施例における桃抽出物のセラミド含有量（純度）の測定は、以下のようにして行った。
１．測定サンプルは、桃抽出物を２０ｍｇ／ｍＬとなるように、クロロホルム／メタノール（２：１v/v）混液に溶解し、サンプル溶液とした。
２．標準品は、マトレア社（Matreya：USA）の標準物質（大豆由来精製品）を用い、２ｍｇ／ｍＬとなるように、クロロホルム／メタノール（２：１v/v）混液に溶解し、順次希釈系列を作成し、標準液とした。
３．ＴＬＣプレート（Analtech社、Silica Gel GF、Scored　１０×２０ｃｍ、２５０μｍ）に、サンプル溶液および標準液を各々１μＬスポットし、展開溶媒（クロロホルム：メタノール：酢酸：水＝２０：３．５：２．３：０．７v/v/v/v）で展開した。展開後、プレートを室温で乾燥し、５０％硫酸を噴霧し、１５０℃で６分間加熱して発色させた。
　桃抽出物中のセラミド含有量（純度）は、プレート上の発色スポットの濃度を、デンシトメーター（アトー社製、CS Analyzer）で測定し、標準液から作成した検量線から算出した。 Test Example 1: Measurement of ceramide content The ceramide content (purity) of the peach extract in the following examples was measured as follows.
1. As a measurement sample, a peach extract was dissolved in a chloroform / methanol (2: 1 v / v) mixed solution so as to be 20 mg / mL to obtain a sample solution.
2. For the standard product, use a matreya (USA) standard substance (purified soybean-derived product) and dissolve in a chloroform / methanol (2: 1 v / v) mixture so that the concentration is 2 mg / mL. Prepared as a standard solution.
3. 1 μL each of sample solution and standard solution was spotted on a TLC plate (Analtech, Silica Gel GF, Scored 10 × 20 cm, 250 μm), and developing solvent (chloroform: methanol: acetic acid: water = 20: 3.5: 2.3). : 0.7 v / v / v / v). After development, the plate was dried at room temperature, sprayed with 50% sulfuric acid, and heated at 150 ° C. for 6 minutes for color development.
The ceramide content (purity) in the peach extract was calculated from a calibration curve prepared from a standard solution by measuring the concentration of the colored spots on the plate with a densitometer (CS Analyzer, manufactured by Ato).
試験例２：ＤＰＰＨラジカル消去活性の測定
　以下の実施例における、ＤＰＰＨ（ジフェニルピクリルヒドラジル）ラジカル消去活性の測定は、以下のようにして行った。
１．測定サンプルをそれぞれエタノールで２ｍｇ／ｍＬに調整した。
２．ＤＰＰＨをエタノールで０．４ｍＭに調整した。
３．次のように測定サンプル溶液を調整した。
（１）サンプル
　　２ｍｇ／ｍＬサンプル溶液２ｍＬにＤＰＰＨ溶液１ｍＬ、エタノール１ｍＬを混合
（２）サンプルブランク
　　２ｍｇ／ｍＬサンプル溶液２ｍＬにエタノール２ｍＬを混合
（３）コントロール
　　エタノール３ｍＬとＤＰＰＨ溶液１ｍＬを混合
（４）コントロールブランク
　　エタノール４ｍＬ
４．上記の測定サンプル溶液を調製後、２０分間遮光して反応させた。反応後、５７１ｎｍの吸光度（ＯＤ）を分光光度計で測定した。 Test Example 2: Measurement of DPPH radical scavenging activity DPPH (diphenylpicrylhydrazyl) radical scavenging activity in the following Examples was measured as follows.
1. Each measurement sample was adjusted to 2 mg / mL with ethanol.
2. DPPH was adjusted to 0.4 mM with ethanol.
3. The measurement sample solution was prepared as follows.
(1) Sample 2 mg / mL sample solution 2 mL mixed with DPPH solution 1 mL and ethanol 1 mL (2) Sample blank 2 mg / mL sample solution 2 mL mixed with ethanol 2 mL (3) Control 3 mL ethanol and DPPH solution 1 mL mixed (4) Control blank ethanol 4mL
4). After the measurement sample solution was prepared, the reaction was allowed to occur for 20 minutes while protected from light. After the reaction, the absorbance (OD) at 571 nm was measured with a spectrophotometer.
　ラジカル消去率（％）は、以下の式から求めた。
ラジカル消去率（％）＝
［１－（サンプルＯＤ－サンプルブランＯＤ）÷（コントロールＯＤ－コントロールブランクＯＤ）］×１００ The radical scavenging rate (%) was obtained from the following formula.
Radical scavenging rate (%) =
[1- (Sample OD−Sample Blanc OD) ÷ (Control OD−Control Blank OD)] × 100
試験例３：総ポリフェノールの含有量測定
　また、以下の実施例における総ポリフェノールの含有量の測定は、以下のようにして行った。
１．測定サンプルを８０％エタノールで１０ｍｇ／ｍＬに調整し、さらに蒸留水にて１０倍希釈して１．０ｍｇ／ｍＬとし、測定サンプルとした。
２．標準品の没食子酸を次のように作製した。
　　　２８ｐｐｍ、１４ｐｐｍ、７ｐｐｍ、3３．５ｐｐｍ、１．７５ｐｐｍ
３．１０％炭酸ナトリウム水溶液を作製した。
４．精製水で５倍希釈フェノール試薬を作製した。
５．各測定サンプル２ｍＬに５倍希釈フェノール試薬２ｍＬ、１０％炭酸ナトリウム水溶液２ｍＬを加え、攪拌して１時間反応させた。
６．反応液を濾過し、７６０ｎｍで吸光度を測定した。
７．没食子酸で検量線を作成して、総ポリフェノール（総ＰＰ）含量（ｍｇ／ｇ）を求めた。 Test Example 3: Content measurement of total polyphenols The content of total polyphenols in the following examples was measured as follows.
1. The measurement sample was adjusted to 10 mg / mL with 80% ethanol, and further diluted 10-fold with distilled water to 1.0 mg / mL.
2. A standard gallic acid was prepared as follows.
28ppm, 14ppm, 7ppm, 33.5ppm, 1.75ppm
3. A 10% aqueous sodium carbonate solution was prepared.
4). A 5-fold diluted phenol reagent was prepared with purified water.
5. 2 mL of 5-fold diluted phenol reagent and 2 mL of 10% aqueous sodium carbonate solution were added to 2 mL of each measurement sample, and the mixture was stirred and reacted for 1 hour.
6). The reaction solution was filtered and the absorbance was measured at 760 nm.
7). A calibration curve was prepared with gallic acid to determine the total polyphenol (total PP) content (mg / g).
参考例１：桃加工残渣から、エタノール単独抽出による抽出物の製造
　乾燥した桃加工残渣１０ｇに、９５％エタノール２０ｍＬ加え、４２℃にて３０分間攪拌しながら抽出した。抽出物を減圧濾過して抽出液を得、一方、抽出残渣は再度同様に抽出処理して抽出液を得た。両抽出液を合わせ、エバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥し、オレンジ色の固形物１．１７ｇを得た。 Reference Example 1: Preparation of extract from peach processing residue by extraction with ethanol alone To 10 g of dried peach processing residue, 20 mL of 95% ethanol was added and extracted with stirring at 42 ° C for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, while the extraction residue was again extracted in the same manner to obtain an extract. Both extracts were combined, concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 1.17 g of an orange solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：０．７％
　ＤＰＰＨ活性：８８．８％
　総ポリフェノール含量：１９．０ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 0.7%
DPPH activity: 88.8%
Total polyphenol content: 19.0 mg / g
参考例２：桃加工残渣から、ヘキサン単独抽出による抽出物の製造
　乾燥した桃加工残渣６０ｇにヘキサン２４０ｍＬを加え、６０℃にて２時間、撹拌操作を加えながら抽出（脱脂）した。抽出物を減圧濾過し、追い出しにヘキサン６０ｍＬを用いた。得られた濾液を減圧濃縮し、残渣を減圧乾燥させ、黄色の水あめ状物０．３ｇを得た。 Reference Example 2: Production of extract from peach processing residue by extraction with hexane alone 60 mL of hexane was added to 60 g of dried peach processing residue, followed by extraction (defatting) at 60 ° C. for 2 hours with stirring operation. The extract was filtered under reduced pressure, and 60 mL of hexane was used for eviction. The obtained filtrate was concentrated under reduced pressure, and the residue was dried under reduced pressure to obtain 0.3 g of a yellow starch candy.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：０．０％
　ＤＰＰＨ活性：２４．６％
　総ポリフェノール含量：２．７ｍｇ／ｇ
　なお、この抽出物は、ほとんどが脂質であった。 About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 0.0%
DPPH activity: 24.6%
Total polyphenol content: 2.7 mg / g
The extract was mostly lipid.
実施例１：摘果桃（若桃）からの抽出物の製造
＜抽出溶媒：エタノール単独　ヘキサン／水分配抽出　アルカリ処理有り＞
　冷凍摘果桃（若桃）を電子レンジで１５分間解凍し、ミキサーにて細かく粉砕し、乾燥させた。この粉末５０ｇに９５％エタノール３００ｍＬ（水酸化ナトリウム９．６ｇ含有）と精製水３７．５ｍＬを加え、攪拌しながら４２℃で３０分間抽出した。抽出物を減圧濾過し、濾液にヘキサン３００ｍＬ及び精製水１５０ｍＬを加え攪拌し、分配抽出した。ヘキサン層を回収し、溶媒をエバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥して、緑色固形物１６０．７ｍｇを得た。 Example 1: Production of extract from fruit peach (young peach) <Extraction solvent: ethanol alone, hexane / water partition extraction with alkali treatment>
Frozen fruit peach (young peach) was thawed for 15 minutes in a microwave oven, finely pulverized with a mixer, and dried. To 50 g of this powder, 300 mL of 95% ethanol (containing 9.6 g of sodium hydroxide) and 37.5 mL of purified water were added and extracted at 42 ° C. for 30 minutes with stirring. The extract was filtered under reduced pressure, 300 mL of hexane and 150 mL of purified water were added to the filtrate, and the mixture was extracted by partitioning. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 160.7 mg of a green solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：１．８％
　ＤＰＰＨ活性：６．５％
　総ポリフェノール含量：０．４ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 1.8%
DPPH activity: 6.5%
Total polyphenol content: 0.4 mg / g
実施例２：摘果桃（若桃）からの抽出物の製造
＜抽出溶媒：エタノール単独　ヘキサン／水分配抽出　アルカリ処理無し＞
　冷凍摘果桃（若桃）を電子レンジで１５分間解凍し、ミキサーにて細かく粉砕し、乾燥させた。この粉末５０ｇを９５％エタノール３００ｍＬと精製水３７．５ｍＬを加え、攪拌しながら４２℃で３０分間抽出した。抽出物を減圧濾過し、濾液にヘキサン３００ｍＬ及び精製水１５０ｍＬを加え攪拌し、分配抽出した。ヘキサン層を回収し、溶媒をエバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥して、緑色固形物４８６．０ｍｇを得た。 Example 2: Production of extract from fruit peach (young peach) <Extraction solvent: ethanol alone, hexane / water partition extraction, no alkali treatment>
Frozen fruit peach (young peach) was thawed for 15 minutes in a microwave oven, finely pulverized with a mixer, and dried. 50 g of this powder was added with 300 mL of 95% ethanol and 37.5 mL of purified water, and extracted at 42 ° C. for 30 minutes with stirring. The extract was filtered under reduced pressure, 300 mL of hexane and 150 mL of purified water were added to the filtrate, and the mixture was extracted by partitioning. The hexane layer was collected, the solvent was concentrated under reduced pressure with an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 486.0 mg of a green solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：２．２％
　ＤＰＰＨ活性：２２．５％
　総ポリフェノール含量：３．４ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 2.2%
DPPH activity: 22.5%
Total polyphenol content: 3.4 mg / g
実施例３：桃加工残渣からの抽出物の製造
＜脱脂処理後　抽出溶媒：エタノール単独　ヘキサン／水分配抽出＞
　モモジュース製造後の絞り粕（桃加工残渣）を乾燥し、その桃加工残渣２００ｇにヘキサン８００ｍＬを加えて、７０℃で４時間攪拌して脱脂処理した。脱脂処理後の桃加工残渣を減圧濾過して回収した。得られた脱脂処理後の桃加工残渣に９５％エタノール８００ｍＬ加え、７０℃で６０分間抽出し、減圧濾過して抽出液を得た。抽出残渣は再度同様に処理して抽出液を得た。
　両抽出液を合わせ、９５％エタノールにて容量を１６００ｍＬに調整し、ヘキサン１６００ｍＬを添加し、７０℃で６０分間攪拌した。さらに精製水１６００ｍＬを加え、７０℃で６０分間、分配抽出した。ヘキサン層を回収し、溶媒をエバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥して、褐色固形物４．３６ｇを得た。 Example 3: Production of extract from peach processing residue <After degreasing process Extraction solvent: Ethanol alone, hexane / water partition extraction>
The squeezed rice cake (peach processed residue) after producing peach juice was dried, and 800 mL of hexane was added to 200 g of the peach processed residue, followed by stirring at 70 ° C. for 4 hours for degreasing treatment. The peach processing residue after the degreasing treatment was recovered by filtration under reduced pressure. 800 mL of 95% ethanol was added to the resulting defatted peach processed residue, extracted at 70 ° C. for 60 minutes, and filtered under reduced pressure to obtain an extract. The extraction residue was treated again in the same manner to obtain an extract.
Both extracts were combined, the volume was adjusted to 1600 mL with 95% ethanol, 1600 mL of hexane was added, and the mixture was stirred at 70 ° C. for 60 minutes. Further, 1600 mL of purified water was added, and partition extraction was performed at 70 ° C. for 60 minutes. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 4.36 g of a brown solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：８．８％
　ＤＰＰＨ活性：７２．７％
　総ポリフェノール含量：７．６ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 8.8%
DPPH activity: 72.7%
Total polyphenol content: 7.6 mg / g
実施例４：桃加工残渣からの抽出物の製造
＜抽出溶媒：エタノール単独　ヘキサン／水分配抽出　アルカリ処理有り＞
　未乾燥桃加工残渣１００ｇに９５％エタノール２００ｍＬ（水酸化ナトリウム６．４ｇ含有）と精製水２５ｍＬを加え、４２℃にて３０分間攪拌しながら抽出した。抽出物を減圧濾過して抽出液を得、抽出残渣は再度同様に処理して抽出液を得た。両抽出液を合わせ、ヘキサン４００ｍＬと精製水２００ｍＬを加え、１時間攪拌、分配抽出した。ヘキサン層を回収し、溶媒をエバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥して、オレンジ色の固形物１３１．３ｍｇを得た。 Example 4: Production of extract from peach processing residue <Extraction solvent: ethanol alone, hexane / water partition extraction with alkali treatment>
To 100 g of the dried peach processing residue, 200 mL of 95% ethanol (containing 6.4 g of sodium hydroxide) and 25 mL of purified water were added, and the mixture was extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, and the extraction residue was similarly treated again to obtain an extract. Both extracts were combined, 400 mL of hexane and 200 mL of purified water were added, and the mixture was stirred and distributed for 1 hour. The hexane layer was collected, the solvent was concentrated under reduced pressure with an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 131.3 mg of an orange solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：１０．７％
　ＤＰＰＨ活性：２２．２％
　総ポリフェノール含量：４．３ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 10.7%
DPPH activity: 22.2%
Total polyphenol content: 4.3 mg / g
実施例５：桃加工残渣からの抽出物の製造
＜抽出溶媒：エタノール単独　ヘキサン／水分配抽出　アルカリ処理無し＞
　未乾燥桃加工残渣１００ｇに９５％エタノール２００ｍＬと精製水２５ｍＬを加え、４２℃にて３０分間攪拌しながら抽出した。抽出物を減圧濾過して抽出液を得、抽出残渣は再度同様に処理して抽出液を得た。両抽出液を合わせ、ヘキサン４００ｍＬと精製水２００ｍＬを加え、１時間攪拌、分配抽出した。ヘキサン層を回収し、溶媒をエバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥して、オレンジ色の固形物１７２．１ｍｇを得た。 Example 5: Preparation of extract from peach processing residue <Extraction solvent: ethanol alone, hexane / water partition extraction, no alkali treatment>
To 100 g of the undried peach processing residue, 200 mL of 95% ethanol and 25 mL of purified water were added, and extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, and the extraction residue was similarly treated again to obtain an extract. Both extracts were combined, 400 mL of hexane and 200 mL of purified water were added, and the mixture was stirred and distributed for 1 hour. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 172.1 mg of an orange solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：１１．７％
　ＤＰＰＨ活性：６１．９％
　総ポリフェノール含量：４．４ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 11.7%
DPPH activity: 61.9%
Total polyphenol content: 4.4 mg / g
実施例６：桃加工残渣からの抽出物の製造
＜抽出溶媒：エタノール／ヘキサン混液　ヘキサン／水分配抽出＞
　未乾燥桃加工残渣１００ｇに９５％エタノール２００ｍＬ、ヘキサン１００ｍＬ及び精製水２５ｍＬを加え、４２℃にて３０分間攪拌しながら抽出した。抽出物を減圧濾過して抽出液を得、濾液にヘキサン１００ｍＬと精製水１００ｍＬを加え、４２℃で１時間攪拌、ヘキサン／水による分配抽出した。ヘキサン層を回収し、溶媒をエバポレーターで減圧濃縮し、残渣を６０℃にて減圧乾燥して、オレンジ色の固形物１７７．８ｍｇを得た。 Example 6: Preparation of extract from peach processing residue <Extraction solvent: Ethanol / hexane mixture hexane / water partition extraction>
To 100 g of the undried peach processing residue, 200 mL of 95% ethanol, 100 mL of hexane and 25 mL of purified water were added, and the mixture was extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure to obtain an extract, and 100 mL of hexane and 100 mL of purified water were added to the filtrate, and the mixture was stirred at 42 ° C. for 1 hour and partitioned and extracted with hexane / water. The hexane layer was collected, the solvent was concentrated under reduced pressure using an evaporator, and the residue was dried under reduced pressure at 60 ° C. to obtain 177.8 mg of an orange solid.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：１０．７％
　ＤＰＰＨ活性：２１．４％
　総ポリフェノール含量：１．４ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 10.7%
DPPH activity: 21.4%
Total polyphenol content: 1.4 mg / g
実施例７：桃加工残渣からの抽出物の製造
＜抽出溶媒：エタノール単独　ヘキサン／水分配抽出＞
　乾燥した桃加工残渣５０ｇに９５％エタノール２００ｍＬを加え、４２℃にて３０分間撹拌をしながら抽出した。抽出物を減圧濾過し、追い出しには９５％エタノールを５０ｍＬ用いた。残渣を同様の方法で再度抽出し、減圧濾過、追い出しを行った。合わせた濾液（１５０ｍＬ）にヘキサン１５０ｍＬを添加し、３０分間撹拌し、次いで蒸留水１５０ｍＬを添加し、３０分間撹拌処理をしてヘキサン／水による分配抽出を行った。ヘキサン層を回収して減圧濃縮を行い、残渣を減圧乾燥して、抽出物としてオレンジ色をした水あめ状物３．８５ｇを得た。 Example 7: Preparation of extract from peach processing residue <Extraction solvent: ethanol alone, hexane / water partition extraction>
To 50 g of the dried peach processing residue, 200 mL of 95% ethanol was added, and extracted with stirring at 42 ° C. for 30 minutes. The extract was filtered under reduced pressure, and 50 mL of 95% ethanol was used to drive out the extract. The residue was extracted again in the same manner, filtered under reduced pressure, and expelled. 150 mL of hexane was added to the combined filtrate (150 mL) and stirred for 30 minutes, and then 150 mL of distilled water was added and stirred for 30 minutes to perform partition extraction with hexane / water. The hexane layer was collected and concentrated under reduced pressure, and the residue was dried under reduced pressure to obtain 3.85 g of an orange-colored starch candy as an extract.
　得られた抽出物について、上記した試験例１、２および３に基づき、セラミド含量（純度）、ＤＰＰＨ活性及び総ポリフェノール含量を測定した結果、以下のとおりであった。
　セラミド含量（純度）：２．４％
　ＤＰＰＨ活性：３６．５％
　総ポリフェノール含量：２９．２ｍｇ／ｇ About the obtained extract, as a result of measuring ceramide content (purity), DPPH activity, and total polyphenol content based on Test Examples 1, 2, and 3 described above, the results were as follows.
Ceramide content (purity): 2.4%
DPPH activity: 36.5%
Total polyphenol content: 29.2 mg / g
実施例８：桃原料の抽出液に対するヘキサン／水の分配抽出条件の検討
　乾燥した桃加工残渣をヘキサンにて脱脂処理し、９５％エタノールにて抽出した一次抽出液に対する、ヘキサン／水の分配抽出の溶媒容量の比率の検討を、下記表１に記載の溶媒比（一次抽出液：ヘキサン：水）で行った。
　試験管に一次抽出液を加え、次にヘキサンを加え１０秒間激しく振とうし、次いで水を加え、再び１０秒間激しく振とうした後静置し、溶液の分離状況を検討した。
　また、ヘキサン層（上澄み層）について、薄層クロマトグラフィー（ＴＬＣ）にて、デンシトメーターを用いて、セラミドの含有量を比較した。
　一次抽出液：ヘキサン：水＝１：１：１で抽出処理をした場合のセラミド含有量を１００％として、各混合比におけるセラミド量を比較した。
　結果を、下記表１に示した。 Example 8: Examination of partition extraction conditions of hexane / water for peach raw material extract Extraction of hexane / water to a primary extract obtained by degreasing a dried peach processed residue with hexane and extracting with 95% ethanol The ratio of the solvent capacity was examined at the solvent ratio (primary extract: hexane: water) described in Table 1 below.
The primary extract was added to the test tube, then hexane was added and shaken vigorously for 10 seconds, then water was added, shaken vigorously again for 10 seconds, and then allowed to stand to examine the state of separation of the solution.
Moreover, about the hexane layer (supernatant layer), content of the ceramide was compared with the densitometer by thin layer chromatography (TLC).
The amount of ceramide in each mixing ratio was compared with the content of ceramide in the case of extraction with primary extract: hexane: water = 1: 1: 1 as 100%.
The results are shown in Table 1 below.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
注１：分離度の表示は以下を意味する。
　　◎：分離が１０分以内で行われ、極めて良好に分離する。
　　○：分離に時間を要せず、３０分以内に良好に分離する。
　　△：分離に３０分以上を要し、中間層が認められるが、一応分離する。
　　×：乳化状態であり、分離しない。 Note 1: The indication of separation means the following.
(Double-circle): Separation is performed within 10 minutes and separation is extremely good.
○: Separation does not take time and is well separated within 30 minutes.
(Triangle | delta): It takes 30 minutes or more for isolation | separation, Although an intermediate | middle layer is recognized, it isolate | separates temporarily.
X: Emulsified and not separated.
　以上の結果から判断すると、本発明の桃原料からの一次抽出溶媒、ついでヘキサン／水による分配抽出にあっては、一次抽出における抽出液と、抽出液の分配抽出に用いるヘキサン及び水の容量比が、１：０．５：０．５～１：２：２のとき、分離度及びセラミド回収量が良好であることがよく理解される。 Judging from the above results, in the primary extraction solvent from the peach raw material of the present invention, and then in the partition extraction with hexane / water, the volume ratio of hexane and water used in the extraction of the primary extraction and the partition extraction of the extract However, when 1: 0.5: 0.5 to 1: 2: 2, it is well understood that the resolution and the amount of ceramide recovered are good.
　上記に示した各実施例から判明するように、本発明により桃原料から特異的な抽出方法を用いることにより、活性酸素消去能を有する桃抽出物を効率良く得ることができた。
　得られる抽出物は活性酸素消去能を有するばかりでなく、桃セラミドを含有するものであり、また、その抽出溶媒として、エタノール及びヘキサンを用いている点で安全性の高いものであり、これら溶媒を適宜組み合わせ、それぞれ目的に応じた抽出手段により、目的とする桃セラミドを含有する抽出物を調製できる点で、極めて特異的なものである。 As can be seen from each of the examples described above, a peach extract having an active oxygen scavenging ability could be efficiently obtained by using a specific extraction method from a peach raw material according to the present invention.
The obtained extract has not only active oxygen scavenging ability but also contains peach ceramide, and is highly safe in that ethanol and hexane are used as the extraction solvent. These are very specific in that an extract containing the desired peach ceramide can be prepared by an extraction means suitable for each purpose.
　本発明により、桃からセラミド（スフィンゴ糖脂質）、配糖体、ポリフェノールを含有し、活性酸素消去能を有する桃抽出物を、安全な抽出方法により製造することができる。
　本発明により得られる桃抽出物は、その抽出に使用する抽出溶媒を種々組み合わせることにより目的とする含有成分の含有量を変化させた桃抽出物を得ることができ、例えば、桃セラミドの含有量を高めた抽出物を提供することができ、更に、活性炭処理やクロマトグラフィーなどの精製方法を適宜組み合わせることにより精製度を高めた抽出物を提供することができ、食品、化粧品、或いは医薬部外品、及びそれらの加工品の素材として用いることができる
　また、原料は、桃の生産過程で生じる摘果桃（若桃）、或いは、桃の果汁等の加工工程から発生する桃加工残渣であり、副生物の有効利用ができる点で、極めて特異的なものである。 According to the present invention, a peach extract containing ceramide (glycosphingolipid), glycoside, and polyphenol and having active oxygen scavenging ability can be produced from peach by a safe extraction method.
The peach extract obtained by the present invention can obtain a peach extract in which the content of the target component is changed by various combinations of extraction solvents used for the extraction, for example, the content of peach ceramide In addition, it is possible to provide an extract with a high degree of purification by appropriately combining purification methods such as activated carbon treatment and chromatography, and can be used for food, cosmetics, or quasi-drugs. In addition, the raw material is a peach processing residue generated from processing processes such as fruit peach (young peach) or peach juice produced in the peach production process, It is extremely specific in that by-products can be used effectively.

Claims (9)

  1. 　摘果桃、成熟桃、又は摘果桃若しくは成熟桃から種子及び果汁を取り除いた繊維成分を含む桃加工残渣を、エタノール、又はエタノール／ヘキサン混液で抽出し、該抽出液を、さらにヘキサン／水により分配抽出することにより得られた、活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有することを特徴とする桃抽出物。 Peached peach, mature peach, or peach processing residue containing fiber components from which seed and fruit juice have been removed from extracted peach or mature peach are extracted with ethanol or ethanol / hexane mixture, and the extract is further distributed with hexane / water A peach extract obtained by extraction, having active oxygen scavenging ability and containing glycosphingolipid (ceramide component).
  2. 　摘果桃、成熟桃、又は桃加工残渣の抽出に用いる抽出液と、抽出液の分配抽出に用いるヘキサン及び水の容量比が、１：０．５：０．５～１：２：２である請求項１に記載の桃抽出物。 The volume ratio of the extract used for extracting the fruit peach, mature peach, or peach processing residue and the hexane and water used for the partition extraction of the extract is 1: 0.5: 0.5 to 1: 2: 2. The peach extract according to claim 1.
  3. 　活性酸素消去能が、ＤＰＰＨ（ジフェニルピクリルヒドラジル）活性である請求項１又は２に記載の桃抽出物。 The peach extract according to claim 1 or 2, wherein the active oxygen scavenging ability is DPPH (diphenylpicrylhydrazyl) activity.
  4. 　ＤＰＰＨ活性が５％以上であり、セラミド含有量が０．５％以上である請求項１～３のいずれかに記載の桃抽出物。 The peach extract according to any one of claims 1 to 3, having a DPPH activity of 5% or more and a ceramide content of 0.5% or more.
  5. 　摘果桃、成熟桃、又は摘果桃若しくは成熟桃から種子及び果汁を取り除いた繊維成分を含む桃加工残渣をエタノール抽出、又はエタノール／ヘキサン混液で抽出して、得られた抽出液を、さらにヘキサン／水により分配抽出することを特徴とする、活性酸素消去能を有し、且つ、スフィンゴ糖脂質（セラミド成分）を含有する桃抽出物の製造方法。 Peached peach, mature peach, or processed peach residue containing fiber components from which seed and fruit juice have been removed from plucked peach or mature peach is extracted with ethanol extraction or ethanol / hexane mixture, and the resulting extract is further mixed with hexane / A method for producing a peach extract having active oxygen scavenging ability and containing glycosphingolipid (ceramide component), characterized by partitioning extraction with water.
  6. 　摘果桃、成熟桃、又は桃加工残渣の抽出に用いる抽出液と、抽出液の分配抽出に用いるヘキサン及び水の容量比が、１：０．５：０．５～１：２：２である請求項５に記載の桃抽出物の製造方法。 The volume ratio of the extract used for extracting the fruit peach, mature peach, or peach processing residue and the hexane and water used for the partition extraction of the extract is 1: 0.5: 0.5 to 1: 2: 2. The manufacturing method of the peach extract of Claim 5.
  7. 　請求項１～４のいずれかに記載の桃抽出物を含む食品、化粧品、或いは医薬部外品、及びそれらの加工品。 Foods, cosmetics or quasi drugs containing the peach extract according to any one of claims 1 to 4, and processed products thereof.
  8. 　請求項１～４のいずれかに記載の桃抽出物をシクロデキストリンと混合し、粉末状物とした請求項７に記載の食品、化粧品、或いは医薬部外品、及びそれらの加工品。 8. The food, cosmetic or quasi-drug of claim 7, wherein the peach extract according to any of claims 1 to 4 is mixed with cyclodextrin to form a powder, and processed products thereof.
  9. 　請求項１～４のいずれかに記載の桃抽出物を含有する水溶液の状態とした請求項７に記載の食品、化粧品、或いは医薬部外品、及びそれらの加工品。 The food, cosmetic or quasi-drug of claim 7, which is in the form of an aqueous solution containing the peach extract according to any one of claims 1 to 4, and a processed product thereof.
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