WO2010061921A1 - Method for stabilizing l-ascorbic acid, liquid extraction preparation, solid extract, and semi-fluid extract - Google Patents

Method for stabilizing l-ascorbic acid, liquid extraction preparation, solid extract, and semi-fluid extract Download PDF

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WO2010061921A1
WO2010061921A1 PCT/JP2009/070049 JP2009070049W WO2010061921A1 WO 2010061921 A1 WO2010061921 A1 WO 2010061921A1 JP 2009070049 W JP2009070049 W JP 2009070049W WO 2010061921 A1 WO2010061921 A1 WO 2010061921A1
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ascorbic acid
stabilizing
liquid extract
extract
rutin
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French (fr)
Japanese (ja)
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チャン カナレス アルテミオ
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株式会社ヤマノ
ヤマノ デル ペルー エス．エー．シー．
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/08—Solutions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/365—Lactones
    • A61K31/375—Ascorbic acid, i.e. vitamin C; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/67—Vitamins
    • A61K8/676—Ascorbic acid, i.e. vitamin C
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Definitions

  • the present invention relates to a method for stabilizing L-ascorbic acid (vitamin C) contained in a liquid extract from a plant for a long period of time.
  • L-ascorbic acid (common name: vitamin C) is widely known to cure scurvy.
  • L-ascorbic acid is known to contribute to various biological processes such as collagen synthesis, antioxidant, intestinal absorption of iron, and amino acid metabolism.
  • this L-ascorbic acid cannot be synthesized in the human body, it must be taken from the outside. Therefore, at present, in the fields of food, beverages, cosmetics and the like, L-ascorbic acid is added to products to increase added value as products that can maintain health, promote beauty, and the like.
  • L-ascorbic acid can be synthesized and produced, it is also a natural compound contained in many plants, and tends to be contained especially in fruits.
  • L-ascorbic acid as an additive used in the fields of foods, beverages, cosmetics and the like is not a synthesized L-ascorbic acid, but a natural product of plant-derived L-ascorbic acid due to an increase in health consciousness. Use is desired. Therefore, L-ascorbic acid is extracted from foods, beverages, cosmetics, etc. by extracting fruit juices, extracts, pulps, etc. from plants such as fruits and vegetables and processing them into solids such as liquids, semi-fluids, powders, etc. Used as an additive.
  • L-ascorbic acid contained in the extract is susceptible to oxidation by air and decomposition by heat, and the L-ascorbic acid content decreases with time immediately after extraction. Therefore, as an L-ascorbic acid additive, securing long-term storage has been a problem. Further, even at room temperature, an aqueous solution containing L-ascorbic acid is likely to be oxidized and decomposed when there is an environmental change such as a slight temperature change, and L-ascorbic acid may exist stably in the aqueous solution. It becomes difficult.
  • L-ascorbic acid additive must also be environmentally controlled when stored as an additive, and oxidation and decomposition of L-ascorbic acid occur when the temperature during addition processing to foods and cosmetics is high. Because it is easy, it is necessary to use an excessive amount of additive more than necessary in consideration of the amount of oxidation / decomposition, and there is a problem that the additive cost cannot be reduced because the use efficiency as an additive is poor. .
  • natural L-ascorbic acid contained in the product is not oxidized or decomposed as much as possible. That is, as a natural L-ascorbic acid additive, a method capable of storing the L-ascorbic acid so that the L-ascorbic acid does not oxidize or decompose for a certain period of time has been desired.
  • the present invention uses a component that is naturally present in a plant or the like in a plant-derived extract containing natural L-ascorbic acid, and enhances long-term preservation of L-ascorbic acid present in the extract.
  • a method for stabilizing L-ascorbic acid which can also improve heat resistance so that thermal decomposition does not occur, is provided.
  • Method for stabilizing L-ascorbic acid according to the present invention stabilizes L-ascorbic acid contained in liquid extracts obtained from all plants including fruits and vegetables.
  • the stabilizing solution preferably contains rutin and / or a derivative thereof in an amount of 0.5% w / v to 10% w / v.
  • the stabilizing solution is preferably an alkaline solution or a mixed solution obtained by mixing ethanol and rutin and / or a derivative thereof.
  • an alkaline aqueous solution containing potassium hydroxide or sodium hydroxide as the alkaline component is preferably used.
  • the alkaline aqueous solution containing potassium hydroxide or sodium hydroxide at a concentration of 0.2% w / v to 0.8% w / v is used. It is preferable.
  • the stabilizing solution is preferably an aqueous alcohol extract obtained by extracting rutin from a plant containing rutin with aqueous alcohol.
  • the prepared liquid extract may contain rutin and / or a derivative thereof at a concentration of 0.01% w / v to 1% w / v. preferable.
  • Prepared liquid extract according to the present invention The prepared liquid extract according to the present invention is characterized by being obtained by using the above-described method for stabilizing L-ascorbic acid.
  • Solid extract according to the present invention is a solid extract obtained by processing the liquid extract into a solid, and the liquid extract is an L according to the present invention.
  • the semi-fluid extract according to the present invention is a semi-fluid extract obtained by processing the liquid extract into a semi-fluid form.
  • the method for stabilizing L-ascorbic acid comprises adding a stabilizing solution containing rutin and / or a derivative thereof to a liquid extract containing L-ascorbic acid obtained from a plant. -Suppresses the oxidative degradation of ascorbic acid and makes it possible to maintain the content of L-ascorbic acid in the liquid extract for a long period of time. Therefore, by adopting this stabilization method, even when a liquid extract from a plant containing natural L-ascorbic acid is stored for a long period of time, oxidative degradation of the natural L-ascorbic acid contained is minimized. Since it can be suppressed, natural L-ascorbic acid contained in plants can be easily used in the food industry and the cosmetics industry.
  • the L-ascorbic acid stabilization method according to the present invention is a method of stabilizing L-ascorbic acid contained in a liquid extract obtained from plants such as fruits and vegetables.
  • liquid extract obtained from plants hereinafter simply referred to as “liquid extract” means juices, fruit juices, liquid colorants, syrups obtained from all plants such as fruits and vegetables. It is a term described as a concept that includes all of a liquid extract, a complete liquid state such as a paste, a semi-solid state mixed with a liquid and a part of a pulp, and a state that easily flows. It means one containing at least natural L-ascorbic acid.
  • the method for stabilizing L-ascorbic acid according to the present invention comprises mixing the liquid extract with a stabilizing solution containing rutin and / or a derivative thereof, so that L-ascorbine contained in the liquid extract is contained.
  • a stabilizing solution containing rutin and / or a derivative thereof so that L-ascorbine contained in the liquid extract is contained.
  • L-ascorbic acid which is a target for suppressing oxidative degradation
  • L-ascorbic acid is known to have a lactone structure.
  • This L-ascorbic acid is acidic in an aqueous solution, but it is not a property due to the carboxyl group in the structural formula of L-ascorbic acid, and the ⁇ electron of the double bond is located at the carbon 3 position. It is transmitted between a certain hydroxy group and a carbonyl group, and the hydroxyl group releases a proton and ionizes to form an anion to become a conjugated base having a resonance structure, delocalizing the negative charge, and being stabilized. Because.
  • the hydroxyl group at the position of carbon 2 may also dissociate to form a dianion.
  • the oxidation of L-ascorbic acid is changed by a reversible reaction to dehydroascorbate having a structure shown in Chemical Formula 1 by first releasing two protons from ascorbate.
  • This dehydroascorbic acid maintains the function expected of L-ascorbic acid.
  • the lactone structure of dehydroascorbic acid has extremely low chemical stability compared to the lactone of ascorbic acid, it is very easily hydrolyzed and converted to 2,3-diketogulonic acid. This 2,3-diketogulonic acid may be decomposed later by a decarboxylation reaction.
  • This 2,3-diketogulonic acid and its degradation products do not show the same activity as L-ascorbic acid and do not show the expected function of L-ascorbic acid. Therefore, unless the oxidative degradation of L-ascorbic acid in the liquid extract is prevented, there is a high possibility that the effect of L-ascorbic acid cannot be obtained even if natural L-ascorbic acid is used in foods, cosmetics, etc. It is not preferable.
  • L-ascorbic acid may be catalyzed by ascorbic acid oxidase, which is abundant in some plants.
  • L-ascorbic acid is relatively stable even in the presence of oxygen if no metal component is present, but if there is a metal component exhibiting a catalytic action such as iron or copper in the environment, These act similarly to the coenzyme and cause chemical oxidation of L-ascorbic acid.
  • copper has a remarkable catalytic action, easily acts as a coenzyme, and oxidatively decomposes ascorbic acid with 80 times the efficiency of iron.
  • the method for stabilizing L-ascorbic acid according to the present invention includes a liquid extract from plants such as fruits and vegetables as a method that does not depend on metal components contained in the liquid extract of plants, By mixing with a stabilizing solution containing rutin and / or a derivative thereof, the oxidative degradation of L-ascorbic acid contained in the liquid extract is suppressed, and the L-ascorbic acid contained in the liquid extract is maintained for a long time. The method of stabilizing was adopted.
  • Rutin (sometimes called Rutin, Lutoside, Quercetin-3-rutinoside, etc.) is a kind of citrus flavonoid.
  • the molecular formula of this rutin is C 27 H 30 O 16 and is a glycoside in which ⁇ -rutinose (6-O- ⁇ -L-rhamnosyl-D- ⁇ -glucose) is bound to the oxygen at position 3 of quercetin.
  • natural rutin is used for this rutin. Natural rutin is insoluble in water and can be dissolved in polar solvents such as alcohol.
  • the rutin derivative in the present invention is a natural rutin derivative and refers to flavonoids naturally present in many vegetables and fruits, for example, flavonoids such as diosmin and diosmoside.
  • rutin and its derivatives themselves have an antioxidative action, so they remove blood with active oxygen, purify blood, lower blood pressure and blood sugar, activate pancreatic function, strengthen capillary walls It has an effect, a capillary permeation suppression effect, an antiallergic effect, and the like, and is said to have an effect of preventing internal bleeding such as intracerebral hemorrhage.
  • the antioxidant action of rutin and its derivatives against L-ascorbic acid is exerted by at least two mechanisms.
  • the first effect is that rutin and its derivative donate one electron to the L-ascorbic acid side, thereby neutralizing the free radical generated in L-ascorbic acid, and dehydroascorbine from L-ascorbic acid. The chain reaction that converts to acid is stopped.
  • the second action exhibits the effect of inhibiting the function of ascorbic acid oxidase that functions as an oxidation catalyst contained in the liquid extract together with L-ascorbic acid.
  • rutin and its derivatives may function as chelating agents that chelate and inactivate metals that act as oxidation catalysts.
  • natural rutins In the method for stabilizing L-ascorbic acid according to the present invention, natural rutin and / or a derivative thereof (hereinafter simply referred to as “natural rutins”) are used. However, natural rutins often have the property of being hardly soluble in water. Even if these are added as powdered solids to a liquid extract from a plant, the effect of preventing oxidative degradation of L-ascorbic acid is hardly obtained.
  • a stabilizing solution (A) an alkaline solution or a mixed solution in which ethanol and rutin and / or a derivative thereof are mixed, or (B) an aqueous alcohol extract obtained from a plant containing rutin, Either of these is preferably used.
  • the former stabilization solution a mixed solution obtained by mixing this with rutin and / or a derivative thereof using either an alkaline solution or ethanol as a solvent is used. That is, when an alkaline solution is used alone as a solvent, ethanol may be used alone.
  • the reason why the alkaline solution and ethanol are used is that they can be used as components having no toxicity to the human body. Which solvent is used depends on whether the liquid extract of the plant obtained by using the method for stabilizing L-ascorbic acid according to the present invention is used in the food field, soft drink field, cosmetic field, etc. In consideration of the field, a usable solvent may be appropriately selected and used.
  • potassium hydroxide aqueous solution or sodium hydroxide aqueous solution when using an alkali solution as a solvent of the said stabilization solution, it is preferable to use potassium hydroxide aqueous solution or sodium hydroxide aqueous solution.
  • the potassium hydroxide aqueous solution or sodium hydroxide aqueous solution at this time is an aqueous solution containing potassium hydroxide or sodium hydroxide as an alkali component at a concentration of 0.2% w / v to 0.8% w / v. It is preferable to use it.
  • the alkali component concentration is less than 0.2% w / v, it becomes difficult to dissolve rutin and / or a derivative thereof in a temperature range from room temperature to room temperature.
  • the alkaline component exceeds 0.8% w / v, depending on the amount of the stabilizing solution added to the liquid extract, the amount of the alkaline component in the liquid extract increases.
  • the amount of the alkaline component in the liquid extract increases.
  • the aqueous alcohol extract referred to here is obtained by extracting natural rutin components contained in a plant containing rutin with aqueous alcohol.
  • These stabilizing solutions preferably contain 0.5% w / v to 10% w / v rutin and / or a derivative thereof.
  • the content of rutin and / or derivative thereof contained in the stabilizing solution is less than 0.5% w / v, it is impossible to obtain the stabilizing effect of L-ascorbic acid with a small amount of addition.
  • the stabilizing effect of L-ascorbic acid is considered in consideration of the amount normally contained in the liquid extract from plants. Becomes saturated, and a higher stabilization effect is not obtained.
  • a solution in which rutin is dissolved at a ratio of 5 parts is used as a stabilizing solution.
  • the content of rutin and / or its derivative in the liquid extract is a concentration of 0.01% w / v to 1% w / v. It is preferable to add a stabilizing solution amount.
  • the content of rutin and / or its derivative in the liquid extract after addition of the stabilizing solution is less than 0.01% w / v, the effect of inhibiting the oxidation of natural L-ascorbic acid contained in the liquid extract Can not get enough.
  • the stabilizing solution is preferably added at the stage immediately after extraction when obtaining a liquid extract containing L-ascorbic acid. That is, it means that it is added in the first step of processing vegetables and fruits containing L-ascorbic acid as raw materials.
  • the addition method There is no particular limitation on the addition method, and the necessary amount may be added all at once and stirred, or an appropriate amount may be gradually added continuously in accordance with the extraction amount. For example, when juice is obtained as a processed product, the addition amount of the stabilizing solution is gradually added in accordance with the collection amount when collecting fruit juice of vegetables and fruits.
  • Examples of plants from which the liquid extract is obtained include camcam (CAMU; scientific name Myrciaria dubia), acerola, orange, lemon and the like, which are known to have a high L-ascorbic acid content.
  • Examples of the liquid extract include fruit juices from plants and liquids obtained by extracting plants with water or other solvents. These fruit juices and liquids may contain plant pulp and skin components and residues.
  • Natural camcam is known to have a very high content of L-ascorbic acid, and the region around Peru in South America is the fruit of its origin. At present, cam cams cannot be cultivated outside Peru, so the only cam cams that are distributed outside Peru are only processed products. However, the content of L-ascorbic acid contained in the processed product of the cam cam is reduced with time by being easily oxidized and decomposed within the normal transportation process and storage period until the product processing. For this reason, the processed cam cam product distributed outside Peru has a reduced L-ascorbic acid content in the processed product. Therefore, for efficient addition to foods, dietary supplements, cosmetics, etc., it is preferable to store, transport, etc. as a prepared liquid extract subjected to the method for stabilizing L-ascorbic acid according to the present invention.
  • Form of prepared liquid extract according to the present invention The prepared liquid extract according to the present invention described above is obtained by using the method for stabilizing L-ascorbic acid according to the present invention.
  • Examples of the prepared liquid extract include fruit juices from plants, juices obtained by mixing the fruit juices with water or other solvents, and the like.
  • the solid extract according to the present invention is a solid extract obtained by processing the prepared liquid extract into a solid. That is, the liquid extract was prepared as a prepared liquid extract subjected to L-ascorbic acid stabilization using the L-ascorbic acid stabilization method according to the present invention, and was obtained by processing it into a solid form. It is characterized by this.
  • processing into a solid state includes dehydration extraction, freeze drying processing, spray drying processing, and the like.
  • the semi-fluid extract according to the present invention is a semi-fluid extract obtained by processing the liquid extract into a semi-fluid form.
  • the semi-fluid referred to here is jam, jelly, hard paste with poor fluidity, and the like.
  • This semi-liquid extract is also a prepared liquid extract subjected to L-ascorbic acid stabilization using the L-ascorbic acid stabilization method according to the present invention, and this is processed into a semi-fluid form. It is characterized by being obtained.
  • the prepared liquid extract preferably has a rutin and / or derivative content of 0.01% w / v to 1% w / v. Even when a stabilizing solution is added to the extract of the solid extract or semi-liquid extract, rutin and / or a derivative thereof is included in the final solid extract or semi-fluid extract. Is preferably prepared so as to have a concentration of 0.01% w / w to 1% w / w. When the rutin concentration in the final solid extract or semi-liquid extract is less than 0.01% w / w, the effect of inhibiting the oxidation of L-ascorbic acid cannot be sufficiently obtained. On the other hand, even if the rutin and / or its derivative concentration exceeds 1% w / w, the effect of inhibiting the oxidation of L-ascorbic acid is saturated and becomes excessive. Examples and comparative examples are shown below.
  • Preparation of stabilizing solution First, a 0.5% sodium hydroxide solution in which sodium hydroxide was dissolved in distilled water was prepared. 5 g of natural rutin was added to the 0.5% sodium hydroxide solution, and the total liquid volume after the addition was 100 ml. This stabilizing solution was prepared with 0.05 g (50 mg) of natural rutin in 1 ml of the solution, that is, with a rutin concentration of 0.5% w / v.
  • Preparation of prepared liquid extract Preparation liquid extracts having different rutin contents were prepared by changing the addition amount of the stabilizing solution with respect to 500 ml of the above cam cam juice.
  • a method for adding the stabilizing solution a method of collectively adding the stabilizing solution to the liquid extract was used.
  • a stabilizing solution having a rutin concentration of 0.5% w / v was added to 500 ml of the liquid extract (camcam juice), and the rutin concentration was 0.10 g / L (0.010% w / v).
  • a prepared liquid extract was prepared.
  • the sample M2 has a rutin concentration of 0.25 g / L (0.025% w / v)
  • the sample M3 has a rutin concentration of 0.5 g / L (0.05% w / v)
  • the sample M4 has a rutin concentration of 0.1.
  • Sample M5 was a prepared liquid extract having a rutin concentration of 1 g / L (0.10% w / v). Each sample M1 to M5 was placed in a glass vial and kept at 10 ° C. Table 1 shows the preparation conditions of samples M1 to M5.
  • the comparative example is an example in which the stabilizing solution is not added to the liquid extract used in the example, and is shown as a sample M6. That is, as the sample M6, 500 ml of camcam juice itself, which is a liquid extract, was used.
  • Sample M31 Sterilized and kept refrigerated Sample M32: Sterilized and kept at room temperature Sample M33: Not sterilized and kept refrigerated Sample M34: Not sterilized and kept at room temperature
  • Method for measuring content of L-ascorbic acid The content of L-ascorbic acid was measured by oxidation-reduction titration (Redox titration). Specifically, iodine titration was performed on a reference sample adjusted to a known concentration using an L-ascorbic acid reagent and samples M1 to M6. The amount of L-ascorbic acid contained in samples M1 to M6 was calculated by comparing the amount of iodine standard solution dropped on the reference sample with the amount of iodine standard solution dropped on samples M1 to M6. .
  • Redox titration oxidation-reduction titration
  • iodine standard solution The iodine concentration of the iodine standard solution was set to 0.1N. Specifically, 1.4 g of iodine (I) reagent and 3.6 g of potassium iodide (KI) reagent were dissolved in 10 ml of distilled water in a beaker, and 0.15 ml of concentrated hydrochloric acid was added. Thereafter, distilled water was further added to make this aqueous solution 100 ml to prepare an iodine standard solution.
  • Preparation of indicator A 5% strength starch solution was prepared.
  • L-ascorbic acid reference solution Preparation of L-ascorbic acid reference solution: USP (United States Pharmacopeia) grade L-ascorbic acid reagent (purity: 99.6%) 50 mg was accurately weighed, dissolved in 10 ml of distilled water in a beaker, and further 2N 2.5 ml of sulfuric acid was added to prepare an L-ascorbic acid standard solution.
  • USP United States Pharmacopeia
  • Titration of L-ascorbic acid reference solution 0.5 ml of an indicator was added to the L-ascorbic acid reference solution, and then the iodine standard solution was titrated until a blue color developed to obtain a titer.
  • Titration of samples M1 to M6 5 ml from each sample was accurately weighed, dissolved in 10 ml of distilled water in a beaker, and further 2.5 ml of 2N sulfuric acid was added to obtain a measurement sample. After adding 0.5 ml of an indicator to this measurement sample, the iodine standard solution was titrated until a blue color developed, and the titration amount was determined.
  • L-ascorbic acid concentration in the sample The measurement by the oxidation-reduction titration described above was repeated three times, and the arithmetic average of the titration amounts of the reference sample and each of the samples M1 to M6 was obtained. The L-ascorbic acid concentration in the sample was calculated based on the obtained titer of the reference sample and the titres of the samples M1 to M6.
  • the method for stabilizing L-ascorbic acid According to the method for stabilizing L-ascorbic acid according to the present invention, denaturation of L-ascorbic acid contained in a liquid extract from a plant can be prevented for a long time, and the content of L-ascorbic acid over time can be prevented. Reduction can be suppressed.
  • the decomposition of L-ascorbic acid due to heat is prevented, there is no loss during processing when used as an additive, and the efficiency of addition can be improved. Therefore, when a liquid extract containing L-ascorbic acid is added and processed as an additive for food or cosmetics, the L-ascorbic acid concentration does not decrease even during heat processing, so there are no restrictions during processing.
  • the additive is efficient by suppressing the quantitative loss during processing.
  • plants with a high L-ascorbic acid content are less susceptible to the preservation environment and can maintain the L-ascorbic acid concentration for a long period of time. It can be transported without losing volume, and an increase in demand can be expected.

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Abstract

Disclosed is a method for stabilizing L-ascorbic acid, which is characterized by utilizing a component that naturally occurs in a plant or the like.  The method can improve the long-term storage stability of natural L-ascorbic acid contained in a plant-derived extract containing the L-ascorbic acid, and can also improve the heat resistance of the L-ascorbic acid so that the L-ascorbic acid cannot be thermally degraded.  Specifically disclosed is a method for stabilizing L-ascorbic acid contained in a liquid extract from any one of all plants including fruits and vegetables, which is characterized by mixing the liquid extract with a stabilizing solution containing rutin and/or a derivative thereof to produce a liquid extract preparation in which the oxidative degradation of L-ascorbic acid contained in the liquid extract is inhibited.

Description

Ｌ－アスコルビン酸の安定化方法、調製液体抽出物、固体状抽出物、半流動体抽出物Method for stabilizing L-ascorbic acid, prepared liquid extract, solid extract, semi-liquid extract
　本発明は、植物からの液体抽出物に含まれるＬ－アスコルビン酸（ビタミンＣ）を長期間安定化させる方法に関する。 The present invention relates to a method for stabilizing L-ascorbic acid (vitamin C) contained in a liquid extract from a plant for a long period of time.
　従来から、Ｌ－アスコルビン酸（通称：ビタミンＣ）は、壊血病を治すことが広く知られている。その他、Ｌ－アスコルビン酸は、コラーゲンの合成、抗酸化、鉄の腸内吸収、アミノ酸の代謝等の数多くの生物学的な種々の過程に寄与することが知られている。ところが、このＬ－アスコルビン酸は、人間の体内では合成できないものであるため、外部から摂取する必要があるものである。従って、現代では、食品、飲料、化粧品等の分野において、商品にＬ－アスコルビン酸を添加して、健康維持、美容促進等を図ることの出来る商品としての付加価値を高めている。 Conventionally, L-ascorbic acid (common name: vitamin C) is widely known to cure scurvy. In addition, L-ascorbic acid is known to contribute to various biological processes such as collagen synthesis, antioxidant, intestinal absorption of iron, and amino acid metabolism. However, since this L-ascorbic acid cannot be synthesized in the human body, it must be taken from the outside. Therefore, at present, in the fields of food, beverages, cosmetics and the like, L-ascorbic acid is added to products to increase added value as products that can maintain health, promote beauty, and the like.
　このＬ－アスコルビン酸は、合成して製造可能となっているが、多くの植物が含有する天然化合物でもあり、特に果物類に多く含まれる傾向がある。近年では、健康志向の高まりにより、食品、飲料、化粧品等の分野で使用する添加物としてのＬ－アスコルビン酸は、合成したＬ－アスコルビン酸ではなく、自然物である植物由来のＬ－アスコルビン酸の使用が望まれている。そこで、果物や野菜等の植物から果汁、エキス、果肉等を抽出して、これらを液体、半流動体、粉末等の固体等に加工した抽出物を食品、飲料、化粧品等のＬ－アスコルビン酸添加剤として用いている。 Although this L-ascorbic acid can be synthesized and produced, it is also a natural compound contained in many plants, and tends to be contained especially in fruits. In recent years, L-ascorbic acid as an additive used in the fields of foods, beverages, cosmetics and the like is not a synthesized L-ascorbic acid, but a natural product of plant-derived L-ascorbic acid due to an increase in health consciousness. Use is desired. Therefore, L-ascorbic acid is extracted from foods, beverages, cosmetics, etc. by extracting fruit juices, extracts, pulps, etc. from plants such as fruits and vegetables and processing them into solids such as liquids, semi-fluids, powders, etc. Used as an additive.
特開２００８－１７９６２９号公報JP 2008-179629 A
　しかし、前記抽出物の含有するＬ－アスコルビン酸は、空気による酸化、熱による分解を受けやすく、抽出直後から経時的にＬ－アスコルビン酸含有量が減少する。そのため、Ｌ－アスコルビン酸添加物としては、長期保存性を確保することが問題となってきた。また、常温においても、Ｌ－アスコルビン酸を含有する水溶液は、僅かな温度変化等の環境変化があると酸化・分解を起こしやすく、当該水溶液中でＬ－アスコルビン酸が安定して存在することが困難になる。このため、Ｌ－アスコルビン酸添加剤は、添加剤として保存する際の環境管理も必須となり、食品や化粧品等への添加加工時の温度が高い場合にはＬ－アスコルビン酸の酸化・分解が起こりやすいため、酸化・分解の量を考慮して、必要以上に過剰の添加剤を使用する必要が生じ、添加剤としての使用効率が悪いため、添加剤コストの削減が不可能という問題があった。 However, L-ascorbic acid contained in the extract is susceptible to oxidation by air and decomposition by heat, and the L-ascorbic acid content decreases with time immediately after extraction. Therefore, as an L-ascorbic acid additive, securing long-term storage has been a problem. Further, even at room temperature, an aqueous solution containing L-ascorbic acid is likely to be oxidized and decomposed when there is an environmental change such as a slight temperature change, and L-ascorbic acid may exist stably in the aqueous solution. It becomes difficult. For this reason, L-ascorbic acid additive must also be environmentally controlled when stored as an additive, and oxidation and decomposition of L-ascorbic acid occur when the temperature during addition processing to foods and cosmetics is high. Because it is easy, it is necessary to use an excessive amount of additive more than necessary in consideration of the amount of oxidation / decomposition, and there is a problem that the additive cost cannot be reduced because the use efficiency as an additive is poor. .
　以上のことから、以下のことが容易に考えられる。即ち、果物、野菜、その他の植物から抽出した果汁、エキス、果肉等から得られる天然のＬ－アスコルビン酸添加剤を用いる場合には、人工物では無いために、純粋なＬ－アスコルビン酸含有量には一定の限界がある。従って、天然のＬ－アスコルビン酸添加剤の場合には、当該天然のＬ－アスコルビン酸添加剤が含有するＬ－アスコルビン酸自体の酸化・分解を出来る限り防止する方法が求められる。特に、産業である食品分野、化粧品分野に使用することを考えると、商品の製造過程には一定の時間を要し、市場を流通した商品が消費者の手元に届き消費が行われるまでの期間、当該商品中に含有させた天然のＬ－アスコルビン酸が可能な限り酸化・分解しないことが求められる。即ち、天然のＬ－アスコルビン酸添加剤として、ある一定の期間、当該Ｌ－アスコルビン酸が酸化・分解しないように保存することのできる方法、保管方法等が望まれてきた。 From the above, the following can be considered easily. That is, when a natural L-ascorbic acid additive obtained from fruits, vegetables, fruit juices extracted from other plants, pulp, etc. is used, since it is not an artificial product, pure L-ascorbic acid content Have certain limits. Therefore, in the case of a natural L-ascorbic acid additive, a method for preventing oxidation and decomposition of L-ascorbic acid itself contained in the natural L-ascorbic acid additive as much as possible is required. In particular, considering the use in the food and cosmetic fields, which are industries, the manufacturing process takes a certain amount of time, and the period from when the product distributed in the market reaches the consumer and is consumed. Therefore, it is required that natural L-ascorbic acid contained in the product is not oxidized or decomposed as much as possible. That is, as a natural L-ascorbic acid additive, a method capable of storing the L-ascorbic acid so that the L-ascorbic acid does not oxidize or decompose for a certain period of time has been desired.
　よって、本発明は、天然のＬ－アスコルビン酸を含有する植物由来の抽出物において、植物等に天然に存在する成分を用い、当該抽出物中に存在するＬ－アスコルビン酸の長期保存性を高めるとともに、同時に熱分解が起こらないように耐熱性の向上も可能なＬ－アスコルビン酸の安定化方法を提供する。 Therefore, the present invention uses a component that is naturally present in a plant or the like in a plant-derived extract containing natural L-ascorbic acid, and enhances long-term preservation of L-ascorbic acid present in the extract. At the same time, a method for stabilizing L-ascorbic acid, which can also improve heat resistance so that thermal decomposition does not occur, is provided.
　そこで、本件発明者は、鋭意研究の結果、以下に述べる方法をもって、上記目的を達成できることに想到した。 Therefore, as a result of earnest research, the present inventor has conceived that the above object can be achieved by the method described below.
本件発明に係るＬ－アスコルビン酸の安定化方法：　本件発明に係るＬ－アスコルビン酸の安定化方法は、果実や野菜を含む全ての植物から得られる液体抽出物が含有するＬ－アスコルビン酸を安定化させる方法であって、当該液体抽出物と、ルチン及び／又はその誘導体を含む安定化溶液とを混合することにより、当該液体抽出物が含有するＬ－アスコルビン酸の酸化分解を抑制した調製液体抽出物とすることを特徴とするものである。 Method for stabilizing L-ascorbic acid according to the present invention: The method for stabilizing L-ascorbic acid according to the present invention stabilizes L-ascorbic acid contained in liquid extracts obtained from all plants including fruits and vegetables. A liquid prepared by suppressing the oxidative degradation of L-ascorbic acid contained in the liquid extract by mixing the liquid extract with a stabilizing solution containing rutin and / or a derivative thereof It is characterized by being an extract.
　本件発明に係るＬ－アスコルビン酸の安定化方法において、前記安定化溶液は、ルチン及び／又はその誘導体を０．５％ｗ／ｖ～１０％ｗ／ｖ含有するものを用いることが好ましい。 In the method for stabilizing L-ascorbic acid according to the present invention, the stabilizing solution preferably contains rutin and / or a derivative thereof in an amount of 0.5% w / v to 10% w / v.
　本件発明に係るＬ－アスコルビン酸の安定化方法において、前記安定化溶液は、アルカリ溶液又はエタノールと、ルチン及び／又はその誘導体とを混合させた混合溶液を用いることが好ましい。 In the method for stabilizing L-ascorbic acid according to the present invention, the stabilizing solution is preferably an alkaline solution or a mixed solution obtained by mixing ethanol and rutin and / or a derivative thereof.
　本件発明に係るＬ－アスコルビン酸の安定化方法において、前記安定化溶液の構成成分として、アルカリ溶液を用いる場合、アルカリ成分として水酸化カリウム又は水酸化ナトリウムを含有するアルカリ水溶液を用いることが好ましい。 In the method for stabilizing L-ascorbic acid according to the present invention, when an alkaline solution is used as a component of the stabilizing solution, an alkaline aqueous solution containing potassium hydroxide or sodium hydroxide as the alkaline component is preferably used.
　本件発明に係るＬ－アスコルビン酸の安定化方法において、前記アルカリ水溶液は、水酸化カリウム又は水酸化ナトリウムを０．２％ｗ／ｖ～０．８％ｗ／ｖの濃度で含有するものを用いることが好ましい。 In the method for stabilizing L-ascorbic acid according to the present invention, the alkaline aqueous solution containing potassium hydroxide or sodium hydroxide at a concentration of 0.2% w / v to 0.8% w / v is used. It is preferable.
　本件発明に係るＬ－アスコルビン酸の安定化方法において、前記安定化溶液は、ルチンを含有する植物から、水性アルコールによりルチンを抽出して得られる水性アルコール抽出物を用いることも好ましい。 In the method for stabilizing L-ascorbic acid according to the present invention, the stabilizing solution is preferably an aqueous alcohol extract obtained by extracting rutin from a plant containing rutin with aqueous alcohol.
　本件発明に係るＬ－アスコルビン酸の安定化方法において、前記調製液体抽出物は、ルチン及び／又はその誘導体が０．０１％ｗ／ｖ～１％ｗ／ｖ濃度となるように含有させることが好ましい。 In the method for stabilizing L-ascorbic acid according to the present invention, the prepared liquid extract may contain rutin and / or a derivative thereof at a concentration of 0.01% w / v to 1% w / v. preferable.
本件発明に係る調製液体抽出物：　本件発明に係る調製液体抽出物は、上述のＬ－アスコルビン酸の安定化方法を用いて得られることを特徴とするものである。 Prepared liquid extract according to the present invention: The prepared liquid extract according to the present invention is characterized by being obtained by using the above-described method for stabilizing L-ascorbic acid.
本件発明に係る固体状抽出物：　本件発明に係る固体状抽出物は、前記液体抽出物を固体状に加工して得られる固体状抽出物であって、当該液体抽出物を本件発明に係るＬ－アスコルビン酸の安定化方法を用いてＬ－アスコルビン酸の安定化処理を施した調製液体抽出物とし、これを固体状に加工して得られたことを特徴とするものである。 Solid extract according to the present invention: The solid extract according to the present invention is a solid extract obtained by processing the liquid extract into a solid, and the liquid extract is an L according to the present invention. -A prepared liquid extract subjected to L-ascorbic acid stabilization using an ascorbic acid stabilization method, which is obtained by processing it into a solid form.
本件発明に係る半流動体抽出物：　本件発明に係る半流動体抽出物は、前記液体抽出物を半流動体状に加工して得られる半流動体抽出物であって、当該液体抽出物を本件発明に係るＬ－アスコルビン酸の安定化方法を用いてＬ－アスコルビン酸の安定化処理を施した調製液体抽出物とし、これを半流動体状に加工して得られたことを特徴とするものである。 Semi-fluid extract according to the present invention: The semi-fluid extract according to the present invention is a semi-fluid extract obtained by processing the liquid extract into a semi-fluid form. A prepared liquid extract subjected to L-ascorbic acid stabilization using the L-ascorbic acid stabilization method according to the present invention, which is obtained by processing it into a semi-fluid form Is.
　本発明に係るＬ－アスコルビン酸の安定化方法は、植物から得られるＬ－アスコルビン酸を含有した液体抽出物に対し、ルチン及び／又はその誘導体を含む安定化溶液を添加することにより、当該Ｌ－アスコルビン酸の酸化分解を抑制し、当該液体抽出物中のＬ－アスコルビン酸の含有量を長期間維持することを可能にする。従って、この安定化方法を採用することで、天然のＬ－アスコルビン酸を含有する植物からの液体抽出物を長期間保存しても、含有した天然のＬ－アスコルビン酸の酸化分解を最小限に抑制できるため、植物の含有する天然のＬ－アスコルビン酸の食品産業、化粧品産業での使用が容易となる。 The method for stabilizing L-ascorbic acid according to the present invention comprises adding a stabilizing solution containing rutin and / or a derivative thereof to a liquid extract containing L-ascorbic acid obtained from a plant. -Suppresses the oxidative degradation of ascorbic acid and makes it possible to maintain the content of L-ascorbic acid in the liquid extract for a long period of time. Therefore, by adopting this stabilization method, even when a liquid extract from a plant containing natural L-ascorbic acid is stored for a long period of time, oxidative degradation of the natural L-ascorbic acid contained is minimized. Since it can be suppressed, natural L-ascorbic acid contained in plants can be easily used in the food industry and the cosmetics industry.
　また、植物から得られた天然のＬ－アスコルビン酸の酸化分解の抑制、酸化時間の遅延安定剤として、化学的に合成された人工添加物を用いる必要がない。即ち、自然界の産物として得られるルチン及び／又はその誘導体を、当該Ｌ－アスコルビン酸の酸化分解抑制剤として用いている。よって、植物から得られるＬ－アスコルビン酸を含有した液体抽出物が、Ｌ－アスコルビン酸の酸化分解抑制剤を含有していても、自然界の天然物で構成されているため、食品、飲料、化粧品等への添加物として用いても、人体に対する悪影響が無く、安心して使用できる添加物となる。 Also, it is not necessary to use chemically synthesized artificial additives as a oxidative degradation inhibitor of natural L-ascorbic acid obtained from plants and as a delay stabilizer for oxidation time. That is, rutin and / or a derivative thereof obtained as a natural product is used as an oxidative degradation inhibitor for L-ascorbic acid. Therefore, even if the liquid extract containing L-ascorbic acid obtained from plants contains an oxidative degradation inhibitor of L-ascorbic acid, it is composed of natural products in the natural world. Even if it is used as an additive to the human body, it has no adverse effect on the human body and can be used with confidence.
実施例及び比較例におけるＬ－アスコルビン酸含有量の減少率を示すグラフである。It is a graph which shows the decreasing rate of L-ascorbic acid content in an Example and a comparative example.
Ｌ－アスコルビン酸の安定化方法の形態：　本件発明に係るＬ－アスコルビン酸の安定化方法は、果実や野菜等の植物から得られる液体抽出物が含有するＬ－アスコルビン酸を安定化させる方法である。ここで、「植物から得られる液体抽出物」（以下、単に「液体抽出物」と称する。）とは、果物、野菜等の全ての植物から得られたジュース、果汁、液体着色剤、シロップ、液体エキス、ペースト等の完全な液体状、液体と一部果肉の固体物と混合したセミソリッド状態の全てを含むものであり、容易に流動する状態の全てを含む概念として記載した用語であり、少なくとも天然のＬ－アスコルビン酸を含有しているものを意味する。 Form of L-ascorbic acid stabilization method: The L-ascorbic acid stabilization method according to the present invention is a method of stabilizing L-ascorbic acid contained in a liquid extract obtained from plants such as fruits and vegetables. is there. Here, “liquid extract obtained from plants” (hereinafter simply referred to as “liquid extract”) means juices, fruit juices, liquid colorants, syrups obtained from all plants such as fruits and vegetables. It is a term described as a concept that includes all of a liquid extract, a complete liquid state such as a paste, a semi-solid state mixed with a liquid and a part of a pulp, and a state that easily flows. It means one containing at least natural L-ascorbic acid.
　そして、本件発明に係るＬ－アスコルビン酸の安定化方法は、当該液体抽出物と、ルチン及び／又はその誘導体を含む安定化溶液とを混合することにより、当該液体抽出物が含有するＬ－アスコルビン酸の酸化分解を抑制した調製液体抽出物とすることで、液体抽出物が含有するＬ－アスコルビン酸の安定化を図るのである。 The method for stabilizing L-ascorbic acid according to the present invention comprises mixing the liquid extract with a stabilizing solution containing rutin and / or a derivative thereof, so that L-ascorbine contained in the liquid extract is contained. By preparing a prepared liquid extract in which acid oxidative decomposition is suppressed, L-ascorbic acid contained in the liquid extract is stabilized.
　ここで、酸化分解の抑制対象物であるＬ－アスコルビン酸について説明する。一般的に、Ｌ－アスコルビン酸は、ラクトン構造を有することが知られている。このＬ－アスコルビン酸は、水溶液中で酸性を示すものであるが、Ｌ－アスコルビン酸の構造式中にあるカルボキシル基に起因する性質ではなく、二重結合のπ電子が、炭素３の位置にあるヒドロキシ基とカルボニル基との間に伝わり、ヒドロキシル基がプロトンを放出しイオン化してアニオンを形成し、共鳴構造をもつ共役塩基となり、負電荷を非局在化させて安定化した状態となるからである。このときの解離常数は、ｐＫ＝４．０４である。一方、炭素２の位置にあるヒドロキシル基の場合には、炭素３の位置にあるヒドロキシル基のように、共鳴構造による安定化が起こらない。従って、その解離常数がｐＫ＝１１．４と高くなる。但し、一定の条件の下では、炭素２の位置にあるヒドロキシル基も解離し、ジアニオンを形成する場合もある。 Here, L-ascorbic acid, which is a target for suppressing oxidative degradation, will be described. Generally, L-ascorbic acid is known to have a lactone structure. This L-ascorbic acid is acidic in an aqueous solution, but it is not a property due to the carboxyl group in the structural formula of L-ascorbic acid, and the π electron of the double bond is located at the carbon 3 position. It is transmitted between a certain hydroxy group and a carbonyl group, and the hydroxyl group releases a proton and ionizes to form an anion to become a conjugated base having a resonance structure, delocalizing the negative charge, and being stabilized. Because. The dissociation constant at this time is pK = 4.04. On the other hand, in the case of the hydroxyl group at the carbon 2 position, stabilization due to the resonance structure does not occur unlike the hydroxyl group at the carbon 3 position. Therefore, the dissociation constant is as high as pK = 11.4. However, under certain conditions, the hydroxyl group at the position of carbon 2 may also dissociate to form a dianion.
　次に、Ｌ－アスコルビン酸の酸化について説明する。Ｌ－アスコルビン酸の酸化は、最初にアスコルビン酸（ａｓｃｏｒｂａｔｅ）から、プロトンを２個放出して、化１に示す構造のデヒドロアスコルビン酸（ｄｅｈｙｄｒｏａｓｃｏｒｂａｔｅ）に可逆的な反応で変わる。このデヒドロアスコルビン酸は、Ｌ－アスコルビン酸に期待される機能を維持している。しかし、デヒドロアスコルビン酸のラクトン構造は、アスコルビン酸のラクトンと比べて、化学的安定性が極めて低いため、非常に容易に加水分解し、２，３－ジケトグロン酸に転換する。この２，３－ジケトグロン酸は、事後的に脱カルボキシル化反応によって、分解することがある。この２，３－ジケトグロン酸及びその分解生成物は、Ｌ－アスコルビン酸と同様の活性を示さず、Ｌ－アスコルビン酸に期待される機能を全く示さない。従って、液体抽出物中のＬ－アスコルビン酸の酸化分解を防止しない限り、天然のＬ－アスコルビン酸を食品、化粧品等に使用しても、Ｌ－アスコルビン酸の効能を得られない可能性が高くなり好ましくない。 Next, the oxidation of L-ascorbic acid will be described. The oxidation of L-ascorbic acid is changed by a reversible reaction to dehydroascorbate having a structure shown in Chemical Formula 1 by first releasing two protons from ascorbate. This dehydroascorbic acid maintains the function expected of L-ascorbic acid. However, since the lactone structure of dehydroascorbic acid has extremely low chemical stability compared to the lactone of ascorbic acid, it is very easily hydrolyzed and converted to 2,3-diketogulonic acid. This 2,3-diketogulonic acid may be decomposed later by a decarboxylation reaction. This 2,3-diketogulonic acid and its degradation products do not show the same activity as L-ascorbic acid and do not show the expected function of L-ascorbic acid. Therefore, unless the oxidative degradation of L-ascorbic acid in the liquid extract is prevented, there is a high possibility that the effect of L-ascorbic acid cannot be obtained even if natural L-ascorbic acid is used in foods, cosmetics, etc. It is not preferable.
Figure JPOXMLDOC01-appb-C000001
Figure JPOXMLDOC01-appb-C000001
　また、Ｌ－アスコルビン酸の酸化反応は、一部の植物に豊富に含まれるアスコルビン酸の酸化酵素の触媒作用を受けることがある。更に、Ｌ－アスコルビン酸は、金属成分が全く存在しなければ、酸素が存在する場合でも比較的安定しているが、環境中に鉄や銅等の触媒化作用を示す金属成分が存在すると、これらが補酵素と同様に作用し、化学的にみたＬ－アスコルビン酸の酸化が起こる。特に、銅は、触媒化作用が顕著で、補酵素として作用しやすく、鉄の８０倍もの効率でアスコルビン酸を酸化分解する。一方、銅に対しては、キレート剤を用いてＬ－アスコルビン酸の酸化防止を行う方法が比較的効果があることが知られているが、このキレート化法は、鉄に対しては効果が無い。即ち、植物の液体抽出物に含まれる金属成分に応じた、Ｌ－アスコルビン酸の酸化分解抑制方法の採用が必要と考えられる。 In addition, the oxidation reaction of L-ascorbic acid may be catalyzed by ascorbic acid oxidase, which is abundant in some plants. Furthermore, L-ascorbic acid is relatively stable even in the presence of oxygen if no metal component is present, but if there is a metal component exhibiting a catalytic action such as iron or copper in the environment, These act similarly to the coenzyme and cause chemical oxidation of L-ascorbic acid. In particular, copper has a remarkable catalytic action, easily acts as a coenzyme, and oxidatively decomposes ascorbic acid with 80 times the efficiency of iron. On the other hand, for copper, it is known that a method for preventing oxidation of L-ascorbic acid using a chelating agent is relatively effective, but this chelation method is effective for iron. No. That is, it is considered necessary to adopt a method for inhibiting oxidative degradation of L-ascorbic acid according to the metal component contained in the liquid extract of the plant.
　そこで、本発明に係るＬ－アスコルビン酸の安定化方法は、植物の液体抽出物に含まれる金属成分等に左右されることの無い方法として、果実や野菜等の植物からの液体抽出物と、ルチン及び／又はその誘導体を含む安定化溶液とを混合することにより、当該液体抽出物が含有するＬ－アスコルビン酸の酸化分解を抑制して、液体抽出物に含有するＬ－アスコルビン酸を長期間安定化させる方法を採用した。より具体的に言えば、ルチン及び／又はその誘導体の抗酸化特性を利用し、フリーラジカルの中和作用並びに酸化分解を引き起こす酵素作用を阻害し、同時に金属のキレート化メカニズムによる効果を得て、Ｌ－アスコルビン酸の安定化を行うのである。 Therefore, the method for stabilizing L-ascorbic acid according to the present invention includes a liquid extract from plants such as fruits and vegetables as a method that does not depend on metal components contained in the liquid extract of plants, By mixing with a stabilizing solution containing rutin and / or a derivative thereof, the oxidative degradation of L-ascorbic acid contained in the liquid extract is suppressed, and the L-ascorbic acid contained in the liquid extract is maintained for a long time. The method of stabilizing was adopted. More specifically, by utilizing the antioxidant properties of rutin and / or its derivatives, it inhibits the neutralizing action of free radicals and the enzyme action causing oxidative degradation, and at the same time obtains the effect of the metal chelation mechanism, L-ascorbic acid is stabilized.
　ここで、ルチン及びその誘導体に関して説明する。ルチン（Ｒｕｔｉｎ、ルトサイド、ケルセチン－３－ルチノシド等と称される場合がある。）は、柑橘フラボノイドの一種である。このルチンの分子式は、Ｃ２７Ｈ３０Ｏ１６であり、クエルセチンの３位の酸素にβ－ルチノース（６－Ｏ－α－Ｌ－ラムノシル－Ｄ－β－グルコース）が結合した配糖体である。本発明では、このルチンに天然ルチンを用いる。天然ルチンは、水に対して不溶性で、アルコール等の極性溶媒には溶解可能である。そのため、天然ルチンを水溶性にするため糖化して得られるα－グリコシル－ルチン等の食品添加物として使用可能な誘導体を使用することも可能である。しかし、本発明におけるルチンの誘導体とは、天然のルチン誘導体であり、多くの野菜や果物中に天然に存在するフラボノイド類、例えば、ジオスミン、ジオスモサイド等のフラボノイドをいう。 Here, rutin and its derivatives will be described. Rutin (sometimes called Rutin, Lutoside, Quercetin-3-rutinoside, etc.) is a kind of citrus flavonoid. The molecular formula of this rutin is C 27 H 30 O 16 and is a glycoside in which β-rutinose (6-O-α-L-rhamnosyl-D-β-glucose) is bound to the oxygen at position 3 of quercetin. . In the present invention, natural rutin is used for this rutin. Natural rutin is insoluble in water and can be dissolved in polar solvents such as alcohol. Therefore, it is also possible to use derivatives that can be used as food additives such as α-glycosyl-rutin obtained by saccharification to make natural rutin water-soluble. However, the rutin derivative in the present invention is a natural rutin derivative and refers to flavonoids naturally present in many vegetables and fruits, for example, flavonoids such as diosmin and diosmoside.
　このルチン及びその誘導体自体は、人体においては、抗酸化作用を備えるため血液中の活性酸素除去を行う血液浄化作用、血圧や血糖値の降下作用、膵臓機能の活性化作用、毛細血管壁の強化効果、毛細血管の透過抑制効果、抗アレルギー作用等があり、脳内出血等の体内出血予防の効果があると言われている。 In the human body, rutin and its derivatives themselves have an antioxidative action, so they remove blood with active oxygen, purify blood, lower blood pressure and blood sugar, activate pancreatic function, strengthen capillary walls It has an effect, a capillary permeation suppression effect, an antiallergic effect, and the like, and is said to have an effect of preventing internal bleeding such as intracerebral hemorrhage.
　そして、ルチン及びその誘導体のＬ－アスコルビン酸に対する抗酸化作用は、少なくとも２つのメカニズムによって発揮される。第１の作用は、ルチン及びその誘導体が、１個の電子をＬ－アスコルビン酸側に供与することで、Ｌ－アスコルビン酸に生じたフリーラジカルを中和して、Ｌ－アスコルビン酸からデヒドロアスコルビン酸へ転化する連鎖反応を停止させるものである。第２の作用は、当該液体抽出物にＬ－アスコルビン酸と同時に含まれる酸化触媒として機能するアスコルビン酸の酸化酵素の働きを阻害する効果を発揮する。更に、第３の作用として、ルチン及びその誘導体は、酸化の触媒として働く金属をキレート化して不活性化させるキレート剤としても機能する場合もある。 And, the antioxidant action of rutin and its derivatives against L-ascorbic acid is exerted by at least two mechanisms. The first effect is that rutin and its derivative donate one electron to the L-ascorbic acid side, thereby neutralizing the free radical generated in L-ascorbic acid, and dehydroascorbine from L-ascorbic acid. The chain reaction that converts to acid is stopped. The second action exhibits the effect of inhibiting the function of ascorbic acid oxidase that functions as an oxidation catalyst contained in the liquid extract together with L-ascorbic acid. Furthermore, as a third action, rutin and its derivatives may function as chelating agents that chelate and inactivate metals that act as oxidation catalysts.
　次に、ルチン及び／又はその誘導体を含有した安定化溶液について説明する。本発明に係るＬ－アスコルビン酸の安定化方法では、天然のルチン及び／又はその誘導体（以下、単に「天然ルチン類」と称する。）を用いる。ところが、天然ルチン類は、水に溶けにくい性質を備える場合が多く見られる。これらを粉末状の固体のまま、植物からの液体抽出物に添加しても、Ｌ－アスコルビン酸の酸化分解を防止する効果は殆ど得られない。従って、天然ルチン類は、溶液状として当該液体抽出物に添加して、当該液体抽出物中に均一に分散拡散し、且つ、反応性を高めて当該液体抽出物に含まれるＬ－アスコルビン酸の酸化分解を防止する効果を迅速に得るため、ルチン及び／又はその誘導体が溶解した状態の安定化溶液を用いることが好ましい。 Next, a stabilizing solution containing rutin and / or a derivative thereof will be described. In the method for stabilizing L-ascorbic acid according to the present invention, natural rutin and / or a derivative thereof (hereinafter simply referred to as “natural rutins”) are used. However, natural rutins often have the property of being hardly soluble in water. Even if these are added as powdered solids to a liquid extract from a plant, the effect of preventing oxidative degradation of L-ascorbic acid is hardly obtained. Therefore, natural rutin is added to the liquid extract as a solution, and is uniformly dispersed and diffused in the liquid extract, and the reactivity is increased to increase the reactivity of L-ascorbic acid contained in the liquid extract. In order to quickly obtain the effect of preventing oxidative degradation, it is preferable to use a stabilizing solution in which rutin and / or a derivative thereof is dissolved.
　そこで、安定化溶液としては、（Ａ）アルカリ溶液又はエタノールと、ルチン及び／又はその誘導体とを混合させた混合溶液、若しくは、（Ｂ）ルチンを含有する植物から得られた水性アルコール抽出物、のいずれかを用いることが好ましい。 Therefore, as a stabilizing solution, (A) an alkaline solution or a mixed solution in which ethanol and rutin and / or a derivative thereof are mixed, or (B) an aqueous alcohol extract obtained from a plant containing rutin, Either of these is preferably used.
　前者の安定化溶液としては、アルカリ溶液、エタノールのいずれかを溶媒として用いて、これとルチン及び／又はその誘導体とを混合して得られる混合溶液を用いる。即ち、溶媒として、アルカリ溶液を単独で用いる場合、エタノールを単独で用いる場合がある。ここで、アルカリ溶液、エタノールを用いたのは、人体に対する毒性が無い成分として使用することが可能だからである。また、いずれの溶媒を用いるかは、本発明に係るＬ－アスコルビン酸の安定化方法を用いて得られる植物の液体抽出物の用途が、食品分野、清涼飲料水分野、化粧品分野等のいずれの分野であるのかを考慮して、適宜、使用可能な溶媒を選択使用すればよい。 As the former stabilization solution, a mixed solution obtained by mixing this with rutin and / or a derivative thereof using either an alkaline solution or ethanol as a solvent is used. That is, when an alkaline solution is used alone as a solvent, ethanol may be used alone. Here, the reason why the alkaline solution and ethanol are used is that they can be used as components having no toxicity to the human body. Which solvent is used depends on whether the liquid extract of the plant obtained by using the method for stabilizing L-ascorbic acid according to the present invention is used in the food field, soft drink field, cosmetic field, etc. In consideration of the field, a usable solvent may be appropriately selected and used.
　なお、当該安定化溶液の溶媒として、アルカリ溶液を用いる場合には、水酸化カリウム水溶液又は水酸化ナトリウム水溶液を用いることが好ましい。そして、このときの水酸化カリウム水溶液又は水酸化ナトリウム水溶液は、アルカリ成分としての水酸化カリウム又は水酸化ナトリウムを０．２％ｗ／ｖ～０．８％ｗ／ｖの濃度で含有する水溶液として用いることが好ましい。ここで、当該アルカリ成分濃度が０．２％ｗ／ｖ未満の場合には、常温～室温の温度範囲で、ルチン及び／又はその誘導体の溶解が困難になる。一方、当該アルカリ成分が０．８％ｗ／ｖを超える場合には、前記液体抽出物に対する当該安定化溶液の添加量にもよるが、液体抽出物中のアルカリ成分量が多くなるため、食品分野で使用する際に、人体に対する毒性は無いとしても、味覚に影響を与える場合があり、好ましくない。 In addition, when using an alkali solution as a solvent of the said stabilization solution, it is preferable to use potassium hydroxide aqueous solution or sodium hydroxide aqueous solution. The potassium hydroxide aqueous solution or sodium hydroxide aqueous solution at this time is an aqueous solution containing potassium hydroxide or sodium hydroxide as an alkali component at a concentration of 0.2% w / v to 0.8% w / v. It is preferable to use it. Here, when the alkali component concentration is less than 0.2% w / v, it becomes difficult to dissolve rutin and / or a derivative thereof in a temperature range from room temperature to room temperature. On the other hand, when the alkaline component exceeds 0.8% w / v, depending on the amount of the stabilizing solution added to the liquid extract, the amount of the alkaline component in the liquid extract increases. When used in the field, even if it is not toxic to the human body, it may affect the taste, which is not preferable.
　一方、安定化溶液として、水性アルコール抽出物を用いる場合について説明する。ここでいう水性アルコール抽出物は、ルチンを含有する植物に含まれる天然ルチンの成分を水性アルコールにより抽出して得られるものである。ルチンを含有する植物は多様に存在し、特に限定されるものではない。 On the other hand, the case where an aqueous alcohol extract is used as the stabilizing solution will be described. The aqueous alcohol extract referred to here is obtained by extracting natural rutin components contained in a plant containing rutin with aqueous alcohol. A variety of plants containing rutin exist and are not particularly limited.
　そして、これらの安定化溶液は、ルチン及び／又はその誘導体を０．５％ｗ／ｖ～１０％ｗ／ｖ含有することが好ましい。安定化溶液が含有するルチン及び／又はその誘導体の含有量が０．５％ｗ／ｖ未満の場合には、少量の添加でＬ－アスコルビン酸の安定化効果を得る事が出来なくなり、Ｌ－アスコルビン酸の安定化効果を得るためには、大量の安定化溶液の使用が必要になり、前記液体抽出物の希釈化が起こるため好ましくない。一方、安定化溶液におけるルチン及び／又はその誘導体の含有量を１０％ｗ／ｖを超える量としても、植物からの液体抽出物が通常含有する量を考慮すると、Ｌ－アスコルビン酸の安定化効果は飽和してしまい、より高い安定化効果が得られる訳ではなくなる。以上のことから、例えば、水酸化ナトリウム濃度０．５％ｗ／ｖの水酸化ナトリウム溶液を溶媒として用い、［水酸化ナトリウム溶液］：［ルチン］＝５：１（ルチン１部に対してアルカリ溶液５部を意味する。）の割合でルチンを溶かしたものを安定化溶液として用いる。 These stabilizing solutions preferably contain 0.5% w / v to 10% w / v rutin and / or a derivative thereof. When the content of rutin and / or derivative thereof contained in the stabilizing solution is less than 0.5% w / v, it is impossible to obtain the stabilizing effect of L-ascorbic acid with a small amount of addition. In order to obtain the stabilizing effect of ascorbic acid, it is necessary to use a large amount of a stabilizing solution, and dilution of the liquid extract occurs, which is not preferable. On the other hand, even if the content of rutin and / or a derivative thereof in the stabilizing solution exceeds 10% w / v, the stabilizing effect of L-ascorbic acid is considered in consideration of the amount normally contained in the liquid extract from plants. Becomes saturated, and a higher stabilization effect is not obtained. From the above, for example, a sodium hydroxide solution having a sodium hydroxide concentration of 0.5% w / v is used as a solvent, and [sodium hydroxide solution]: [rutin] = 5: 1 (alkaline to 1 part rutin). A solution in which rutin is dissolved at a ratio of 5 parts is used as a stabilizing solution.
　そして、液体抽出物に対して、上記安定化溶液を添加する場合、当該液体抽出物中におけるルチン及び／又はその誘導体の含有量が、濃度０．０１％ｗ／ｖ～１％ｗ／ｖとなる安定化溶液量を添加することが好ましい。安定化溶液を添加後の液体抽出物中におけるルチン及び／又はその誘導体の含有量が０．０１％ｗ／ｖ未満であると、当該液体抽出物の含有する天然Ｌ－アスコルビン酸の酸化抑制効果を十分に得ることが出来ない。一方、液体抽出物におけるルチン及び／又はその誘導体の含有量が１％ｗ／ｖを超えるような量で安定化溶液を添加しても、天然Ｌ－アスコルビン酸の酸化抑制効果が比例して増加するものではなく、酸化抑制効果が飽和するため、添加量として過剰となる。 When the stabilizing solution is added to the liquid extract, the content of rutin and / or its derivative in the liquid extract is a concentration of 0.01% w / v to 1% w / v. It is preferable to add a stabilizing solution amount. When the content of rutin and / or its derivative in the liquid extract after addition of the stabilizing solution is less than 0.01% w / v, the effect of inhibiting the oxidation of natural L-ascorbic acid contained in the liquid extract Can not get enough. On the other hand, even when the stabilizing solution is added in such an amount that the content of rutin and / or its derivative in the liquid extract exceeds 1% w / v, the effect of suppressing the oxidation of natural L-ascorbic acid increases proportionally. However, since the oxidation suppression effect is saturated, the amount added is excessive.
　更に、安定化溶液の添加方法について説明する。安定化溶液は、Ｌ－アスコルビン酸を含有する液体抽出物を得る際の、抽出直後の段階で添加することが好ましい。即ち、Ｌ－アスコルビン酸を含有する野菜や果物を原材料として加工する最初の工程で添加するという意味である。添加方法については特段の限定はなく、必要量を一括添加し撹拌しても、抽出量に併せて漸次適当量を連続的に添加しても構わない。例えば、加工品としてジュースを得る場合は、野菜や果物の果汁を採取する際に、採取量に併せて、安定化溶液の添加量を漸次添加する等である。 Furthermore, a method for adding the stabilizing solution will be described. The stabilizing solution is preferably added at the stage immediately after extraction when obtaining a liquid extract containing L-ascorbic acid. That is, it means that it is added in the first step of processing vegetables and fruits containing L-ascorbic acid as raw materials. There is no particular limitation on the addition method, and the necessary amount may be added all at once and stirred, or an appropriate amount may be gradually added continuously in accordance with the extraction amount. For example, when juice is obtained as a processed product, the addition amount of the stabilizing solution is gradually added in accordance with the collection amount when collecting fruit juice of vegetables and fruits.
　また、前記液体抽出物を得る植物としては、Ｌ－アスコルビン酸の含有量が多いことで知られるカムカム（ＣＡＭＵ　ＣＡＭＵ；学名Ｍｙｒｃｉａｒｉａ　ｄｕｂｉａ）、アセロラ、オレンジ、レモン等が挙げられる。そして、液体抽出物は、植物からの果汁、植物を水あるいは他の溶剤を用いて抽出して得られた液体が挙げられる。また、これらの果汁や液体に、植物の果肉や皮の成分や残渣が含まれていても良い。特に、本発明に係るＬ－アスコルビン酸の安定化方法を、カムカムからの液体抽出物に適用すると、カムカムに高濃度に含有する天然のＬ－アスコルビン酸を安定化させることができる。その結果、カムカムに含有する高濃度の天然のＬ－アスコルビン酸を、効率よく、あらゆる商品に含有させることが可能となる。天然のカムカムは、Ｌ－アスコルビン酸の含有量が非常に高いことが知られており、南米のペルーを中心とする地域が、その原産地となる果実である。現在のところ、カムカムは、ペルー国外での栽培が不可能であるため、ペルー国外に流通しているカムカムは、その抽出物である加工品のみである。しかし、このカムカムの加工品が含有するＬ－アスコルビン酸は、通常の輸送過程、商品加工までの保存期間内に容易に酸化分解することにより、その含有量が経時的に減少する。このため、ペルー国外で流通するカムカムの加工品は、その加工品に含まれるＬ－アスコルビン酸含有量が減少してしまう。そのため、食品や栄養補助食品、化粧品等に効率良く添加するためには、本発明に係るＬ－アスコルビン酸の安定化方法を施した調製液体抽出物として保存、輸送等することが好適なのである。 Examples of plants from which the liquid extract is obtained include camcam (CAMU; scientific name Myrciaria dubia), acerola, orange, lemon and the like, which are known to have a high L-ascorbic acid content. Examples of the liquid extract include fruit juices from plants and liquids obtained by extracting plants with water or other solvents. These fruit juices and liquids may contain plant pulp and skin components and residues. In particular, when the method for stabilizing L-ascorbic acid according to the present invention is applied to a liquid extract from a cam cam, natural L-ascorbic acid contained in the cam cam at a high concentration can be stabilized. As a result, the natural L-ascorbic acid having a high concentration contained in the cam cam can be efficiently contained in any product. Natural camcam is known to have a very high content of L-ascorbic acid, and the region around Peru in South America is the fruit of its origin. At present, cam cams cannot be cultivated outside Peru, so the only cam cams that are distributed outside Peru are only processed products. However, the content of L-ascorbic acid contained in the processed product of the cam cam is reduced with time by being easily oxidized and decomposed within the normal transportation process and storage period until the product processing. For this reason, the processed cam cam product distributed outside Peru has a reduced L-ascorbic acid content in the processed product. Therefore, for efficient addition to foods, dietary supplements, cosmetics, etc., it is preferable to store, transport, etc. as a prepared liquid extract subjected to the method for stabilizing L-ascorbic acid according to the present invention.
本件発明に係る調製液体抽出物の形態：　上述の本件発明に係る調製液体抽出物は、本件発明に係るＬ－アスコルビン酸の安定化方法を用いて得られることを特徴とするものである。調製液体抽出物とは、植物からの果汁、当該果汁を水あるいは他の溶剤と混合したジュース等が挙げられる。 Form of prepared liquid extract according to the present invention: The prepared liquid extract according to the present invention described above is obtained by using the method for stabilizing L-ascorbic acid according to the present invention. Examples of the prepared liquid extract include fruit juices from plants, juices obtained by mixing the fruit juices with water or other solvents, and the like.
本件発明に係る固体状抽出物の形態：　本件発明に係る固体状抽出物は、前記調製液体抽出物を固体状に加工して得られる固体状抽出物である。即ち、当該液体抽出物を本件発明に係るＬ－アスコルビン酸の安定化方法を用いてＬ－アスコルビン酸の安定化処理を施した調製液体抽出物とし、これを固体状に加工して得られたことを特徴とするものである。ここで、固体状に加工するとは、脱水抽出、フリーズドライ加工、スプレードライ加工等である。 Form of solid extract according to the present invention: The solid extract according to the present invention is a solid extract obtained by processing the prepared liquid extract into a solid. That is, the liquid extract was prepared as a prepared liquid extract subjected to L-ascorbic acid stabilization using the L-ascorbic acid stabilization method according to the present invention, and was obtained by processing it into a solid form. It is characterized by this. Here, processing into a solid state includes dehydration extraction, freeze drying processing, spray drying processing, and the like.
本件発明に係る半流動体抽出物の形態：　本件発明に係る半流動体抽出物は、前記液体抽出物を半流動体状に加工して得られる半流動体抽出物である。ここで言う半流動体とは、ジャム、ゼリー、流動性に乏しい固めのペースト等である。この半流動体状抽出物も、本件発明に係るＬ－アスコルビン酸の安定化方法を用いてＬ－アスコルビン酸の安定化処理を施した調製液体抽出物とし、これを半流動体状に加工して得られたことを特徴とするものである。 Form of semi-fluid extract according to the present invention: The semi-fluid extract according to the present invention is a semi-fluid extract obtained by processing the liquid extract into a semi-fluid form. The semi-fluid referred to here is jam, jelly, hard paste with poor fluidity, and the like. This semi-liquid extract is also a prepared liquid extract subjected to L-ascorbic acid stabilization using the L-ascorbic acid stabilization method according to the present invention, and this is processed into a semi-fluid form. It is characterized by being obtained.
　そして、調製液体抽出物は、ルチン及び／又はその誘導体の含有量が濃度０．０１％ｗ／ｖ～１％ｗ／ｖとなるようにすることが好ましい。そして、上記固体状抽出物又は半流動体抽出物の抽出物に安定化溶液を添加する場合にも、最終的な固体状抽出物又は半流動体抽出物の中に、ルチン及び／又はその誘導体が濃度０．０１％ｗ／ｗ～１％ｗ／ｗとなるように調製して添加することが好ましい。最終的な固体状抽出物又は半流動体抽出物の中のルチン濃度が０．０１％ｗ／ｗ未満であると、Ｌ－アスコルビン酸の酸化抑制効果が十分に得られない。一方、当該ルチン及び／又はその誘導体濃度が１％ｗ／ｗを超えても、Ｌ－アスコルビン酸の酸化抑制効果は飽和して、過剰量となるからである。以下、実施例及び比較例を示す。 The prepared liquid extract preferably has a rutin and / or derivative content of 0.01% w / v to 1% w / v. Even when a stabilizing solution is added to the extract of the solid extract or semi-liquid extract, rutin and / or a derivative thereof is included in the final solid extract or semi-fluid extract. Is preferably prepared so as to have a concentration of 0.01% w / w to 1% w / w. When the rutin concentration in the final solid extract or semi-liquid extract is less than 0.01% w / w, the effect of inhibiting the oxidation of L-ascorbic acid cannot be sufficiently obtained. On the other hand, even if the rutin and / or its derivative concentration exceeds 1% w / w, the effect of inhibiting the oxidation of L-ascorbic acid is saturated and becomes excessive. Examples and comparative examples are shown below.
　実施例では、液体抽出物であるカムカムジュースに、以下に示す安定化溶液を用いて、ルチンの添加量が異なる５つの試料Ｍ１～Ｍ５を作成した。 In the examples, five samples M1 to M5 having different rutin addition amounts were prepared using the following stabilizing solution for the camcorder juice, which is a liquid extract.
　まず、カムカムの果実２ｋｇを、３リットルの水とともに４０℃でパーコレーションによって抽出させ、最終的に３リットルのカムカムジュースを得た。これを５００ｍｌずつに分け、試料Ｍ１～Ｍ５に用いる液体抽出物を用意した。 First, 2 kg of cam cam fruit was extracted by percolation with 3 liters of water at 40 ° C. to finally obtain 3 liters of cam cam juice. This was divided into 500 ml portions, and liquid extracts used for samples M1 to M5 were prepared.
安定化溶液の調製：　まず、水酸化ナトリウムを蒸留水に溶解させた０．５％水酸化ナトリウム溶液を用意した。その０．５％水酸化ナトリウム溶液に、天然ルチン５ｇを添加し、添加後の全液量を１００ｍｌとした。この安定化溶液は、溶液１ｍｌ中に天然ルチンが０．０５ｇ（５０ｍｇ）、つまり、ルチン濃度０．５％ｗ／ｖに調製した。 Preparation of stabilizing solution: First, a 0.5% sodium hydroxide solution in which sodium hydroxide was dissolved in distilled water was prepared. 5 g of natural rutin was added to the 0.5% sodium hydroxide solution, and the total liquid volume after the addition was 100 ml. This stabilizing solution was prepared with 0.05 g (50 mg) of natural rutin in 1 ml of the solution, that is, with a rutin concentration of 0.5% w / v.
調製液体抽出物の作製：　上述のカムカムジュースを５００ｍｌに対し、安定化溶液の添加量を変えて、ルチン含有量の異なる調製液体抽出物を作製した。ここで、安定化溶液の添加方法は、前記液体抽出物に安定化溶液を一括添加する方法を用いた。 Preparation of prepared liquid extract: Preparation liquid extracts having different rutin contents were prepared by changing the addition amount of the stabilizing solution with respect to 500 ml of the above cam cam juice. Here, as a method for adding the stabilizing solution, a method of collectively adding the stabilizing solution to the liquid extract was used.
　試料Ｍ１は、前記液体抽出物（カムカムジュース）５００ｍｌに対し、ルチン濃度０．５％ｗ／ｖの安定化溶液を添加し、ルチン濃度が０．１０ｇ／Ｌ（０．０１０％ｗ／ｖ）となる調製液体抽出物を作製した。同様に、試料Ｍ２はルチン濃度０．２５ｇ／Ｌ（０．０２５％ｗ／ｖ）、試料Ｍ３はルチン濃度０．５ｇ／Ｌ（０．０５％ｗ／ｖ）、試料Ｍ４はルチン濃度０．７５ｇ／Ｌ（０．０７５％ｗ／ｖ）、試料Ｍ５はルチン濃度１ｇ／Ｌ（０．１０％ｗ／ｖ）の調製液体抽出物とした。各資料Ｍ１～Ｍ５はガラスバイアル中に入れ、１０℃に保持した。表１に試料Ｍ１～Ｍ５の調製条件を示す。 For sample M1, a stabilizing solution having a rutin concentration of 0.5% w / v was added to 500 ml of the liquid extract (camcam juice), and the rutin concentration was 0.10 g / L (0.010% w / v). A prepared liquid extract was prepared. Similarly, the sample M2 has a rutin concentration of 0.25 g / L (0.025% w / v), the sample M3 has a rutin concentration of 0.5 g / L (0.05% w / v), and the sample M4 has a rutin concentration of 0.1. 75 g / L (0.075% w / v) and Sample M5 was a prepared liquid extract having a rutin concentration of 1 g / L (0.10% w / v). Each sample M1 to M5 was placed in a glass vial and kept at 10 ° C. Table 1 shows the preparation conditions of samples M1 to M5.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
比較例Comparative example
　比較例は、実施例で用いた液体抽出物に、安定化溶液を添加しない例であり、試料Ｍ６として示す。すなわち、試料Ｍ６は、液体抽出物であるカムカムジュース５００ｍｌそのものを用いた。 The comparative example is an example in which the stabilizing solution is not added to the liquid extract used in the example, and is shown as a sample M6. That is, as the sample M6, 500 ml of camcam juice itself, which is a liquid extract, was used.
Ｌ－アスコルビン酸含有量の評価：　試料Ｍ１～Ｍ６について、Ｌ－アスコルビン酸の濃度を、添加当初（０日目）、７日目、１０日目、１４日目について測定した。結果を表２に示す。 Evaluation of L-ascorbic acid content: For samples M1 to M6, the concentration of L-ascorbic acid was measured at the beginning of addition (day 0), day 7, day 10, and day 14. The results are shown in Table 2.
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　上記実験結果に基づき、０日目に対するＬ－アスコルビン酸濃度の減少率を算出した結果を以下の表３及び図１にグラフで示す。 The results of calculating the decrease rate of the L-ascorbic acid concentration with respect to the 0th day based on the above experimental results are shown in the following Table 3 and FIG.
Figure JPOXMLDOC01-appb-T000004
Figure JPOXMLDOC01-appb-T000004
結果の対比：　表３に示したＬ－アスコルビン酸濃度の減少率を見ると、ルチンを含有する試料Ｍ１～Ｍ５と、安定化溶液を添加しない試料Ｍ６とは、違いが明確に現れた。特に、１４日目の結果を見ると、比較例の試料Ｍ６はＬ－アスコルビン酸濃度の減少率が３２．７４％を示したのに対して、ルチン濃度０．１０ｇ／Ｌの試料Ｍ１は１５．６７％であり、ルチン濃度の１ｇ／Ｌの試料Ｍ５は４．７２％であり、特に、ルチン濃度０．５ｇ／Ｌの試料Ｍ３はＬ－アスコルビン酸濃度の減少率が２．１％であり、最も少ない結果を示した。 Comparison of results: Looking at the decrease rate of the L-ascorbic acid concentration shown in Table 3, the difference clearly appeared between the samples M1 to M5 containing rutin and the sample M6 to which no stabilizing solution was added. In particular, looking at the results on the 14th day, the sample M6 of the comparative example showed a decrease rate of L-ascorbic acid concentration of 32.74%, whereas the sample M1 with the rutin concentration of 0.10 g / L was 15 The sample M5 having a rutin concentration of 1 g / L is 4.72%, and in particular, the sample M3 having a rutin concentration of 0.5 g / L has a decrease rate of L-ascorbic acid concentration of 2.1%. Yes, with the fewest results.
　続いて、試料Ｍ３を用いて、保存環境を変化させた実施例を示す。すなわち、上記実施例の試料Ｍ３と同じ、ルチン濃度０．５ｇ／Ｌのカムカムジュースを用意し、滅菌処理の有無と保存温度を変えた以下の試料Ｍ３１～Ｍ３４を用いて、０日目、７日目、１０日目、１４日目のＬ－アスコルビン酸含有量の変化を測定した。なお、滅菌処理は、８０℃で３０秒間加熱する処理を行った。測定結果を表３に示す。 Subsequently, an example in which the storage environment was changed using the sample M3 will be described. That is, the same as sample M3 in the above example, a camcam juice having a rutin concentration of 0.5 g / L was prepared, and the following samples M31 to M34 with different sterilization treatment and storage temperatures were used, Changes in the L-ascorbic acid content on days 10, 10 and 14 were measured. In addition, the sterilization process performed the process heated at 80 degreeC for 30 second. Table 3 shows the measurement results.
　試料Ｍ３１：滅菌処理し、冷蔵保持
　試料Ｍ３２：滅菌処理し、常温で保持
　試料Ｍ３３：滅菌処理せず、冷蔵保持
　試料Ｍ３４：滅菌処理せず、常温で保持 Sample M31: Sterilized and kept refrigerated Sample M32: Sterilized and kept at room temperature Sample M33: Not sterilized and kept refrigerated Sample M34: Not sterilized and kept at room temperature
Figure JPOXMLDOC01-appb-T000005
Figure JPOXMLDOC01-appb-T000005
　表４から明らかな様に、ルチン濃度０．５ｇ／Ｌのカムカムジュースにおいて、滅菌条件及び温度条件が異なる場合であっても、Ｌ－アスコルビン酸濃度は極めて安定し、変化が無いことが示された。この結果から、保存温度に関わらずＬ－アスコルビン酸濃度の経時変化が極めて少なく、Ｌ－アスコルビン酸を安定化させられることが明らかである。また、滅菌処理を行った試料Ｍ３２及び試料Ｍ３４においても、試料Ｍ３１、試料Ｍ３３と同様の結果となっている。このことから、滅菌処理時の８０℃の加熱によっても、Ｌ－アスコルビン酸が分解されておらず、且つ、その含有量を保つことができることが判明した。以下、Ｌ－アスコルビン酸の含有量の測定方法を説明する。 As is apparent from Table 4, it was shown that the L-ascorbic acid concentration is very stable and unchanged even when the sterilization conditions and temperature conditions are different in the rutin concentration of 0.5 g / L of camcam juice. It was. From this result, it is clear that the L-ascorbic acid concentration hardly changes with time regardless of the storage temperature, and L-ascorbic acid can be stabilized. In addition, the sample M32 and the sample M34 that have been sterilized have the same results as the sample M31 and the sample M33. From this, it was found that L-ascorbic acid was not decomposed even by heating at 80 ° C. during sterilization, and the content could be maintained. Hereinafter, a method for measuring the content of L-ascorbic acid will be described.
Ｌ－アスコルビン酸の含有量の測定方法：　Ｌ－アスコルビン酸の含有量は、酸化還元滴定（Ｒｅｄｏｘ滴定）により測定した。具体的には、Ｌ－アスコルビン酸の試薬を用いて既知の濃度に調整した基準試料と試料Ｍ１～試料Ｍ６とを対象としてヨウ素滴定を実施した。そして、試料Ｍ１～試料Ｍ６が含むＬ－アスコルビン酸量は、基準試料に対して滴下したヨウ素標準溶液量と、試料Ｍ１～試料Ｍ６に対して滴下したヨウ素標準溶液量とを比較して算出した。 Method for measuring content of L-ascorbic acid: The content of L-ascorbic acid was measured by oxidation-reduction titration (Redox titration). Specifically, iodine titration was performed on a reference sample adjusted to a known concentration using an L-ascorbic acid reagent and samples M1 to M6. The amount of L-ascorbic acid contained in samples M1 to M6 was calculated by comparing the amount of iodine standard solution dropped on the reference sample with the amount of iodine standard solution dropped on samples M1 to M6. .
ヨウ素標準溶液の調製：　ヨウ素標準溶液は、ヨウ素濃度を０．１Ｎに設定した。具体的には、ヨウ素（Ｉ）試薬１．４ｇとヨウ化カリウム（ＫＩ）試薬３．６ｇとをビーカー内で１０ｍｌの蒸留水に溶解し、濃塩酸０．１５ｍｌを加えた。その後、この水溶液を１００ｍｌになるよう更に蒸留水を加え、ヨウ素標準溶液を調製した。
指示薬の調製：　濃度５％のデンプン溶液を調製した。
Ｌ－アスコルビン酸基準液の調製：　ＵＳＰ（Ｕｎｉｔｅｄ　Ｓｔａｔｅｓ　Ｐｈａｒｍａｃｏｐｅｉａ）グレードのＬ－アスコルビン酸試薬（純度：９９．６％）５０ｍｇを精密に秤取り、ビーカー内で１０ｍｌの蒸留水に溶解し、更に２Ｎ硫酸２．５ｍｌを加え、Ｌ－アスコルビン酸基準液を調製した。 Preparation of iodine standard solution: The iodine concentration of the iodine standard solution was set to 0.1N. Specifically, 1.4 g of iodine (I) reagent and 3.6 g of potassium iodide (KI) reagent were dissolved in 10 ml of distilled water in a beaker, and 0.15 ml of concentrated hydrochloric acid was added. Thereafter, distilled water was further added to make this aqueous solution 100 ml to prepare an iodine standard solution.
Preparation of indicator: A 5% strength starch solution was prepared.
Preparation of L-ascorbic acid reference solution: USP (United States Pharmacopeia) grade L-ascorbic acid reagent (purity: 99.6%) 50 mg was accurately weighed, dissolved in 10 ml of distilled water in a beaker, and further 2N 2.5 ml of sulfuric acid was added to prepare an L-ascorbic acid standard solution.
Ｌ－アスコルビン酸基準液の滴定：　Ｌ－アスコルビン酸基準液に指示薬０．５ｍｌを添加し、その後、ヨウ素標準溶液を青色が発色するまで滴定し、滴定量を求めた。
試料Ｍ１～試料Ｍ６の滴定：　各試料から５ｍｌを正確に秤取り、ビーカー内で１０ｍｌの蒸留水に溶解し、更に２Ｎ硫酸２．５ｍｌを加え、測定試料とした。この測定試料に指示薬０．５ｍｌを添加した後、ヨウ素標準溶液を青色が発色するまで滴定し、滴定量を求めた。 Titration of L-ascorbic acid reference solution: 0.5 ml of an indicator was added to the L-ascorbic acid reference solution, and then the iodine standard solution was titrated until a blue color developed to obtain a titer.
Titration of samples M1 to M6: 5 ml from each sample was accurately weighed, dissolved in 10 ml of distilled water in a beaker, and further 2.5 ml of 2N sulfuric acid was added to obtain a measurement sample. After adding 0.5 ml of an indicator to this measurement sample, the iodine standard solution was titrated until a blue color developed, and the titration amount was determined.
試料中のＬ－アスコルビン酸濃度：　上述した酸化還元滴定による測定を３回繰り返し、基準試料及び各試料Ｍ１～Ｍ６の滴定量の算術平均を求めた。そして、求められた基準試料の滴定量と各試料Ｍ１～Ｍ６の滴定量を元に、試料中のＬ－アスコルビン酸濃度を算出した。 L-ascorbic acid concentration in the sample: The measurement by the oxidation-reduction titration described above was repeated three times, and the arithmetic average of the titration amounts of the reference sample and each of the samples M1 to M6 was obtained. The L-ascorbic acid concentration in the sample was calculated based on the obtained titer of the reference sample and the titres of the samples M1 to M6.
　本件発明に係るＬ－アスコルビン酸の安定化方法によれば、植物からの液体抽出物に含有するＬ－アスコルビン酸の変性を長時間防ぐことができ、Ｌ－アスコルビン酸の含有量の経時的な減少を抑えることができる。また、熱によるＬ－アスコルビン酸の分解を防ぐので、添加物として使用する場合に加工時にも損失が無く、添加効率を向上させることができる。したがって、Ｌ－アスコルビン酸を含有する液体抽出物を、食品や化粧品等の添加物として添加し加工する場合に、加熱加工時においてもＬ－アスコルビン酸濃度が減少しないので、加工時の制約が無く、また、加工時の量的な損失を抑えて効率的な添加物であると言える。 According to the method for stabilizing L-ascorbic acid according to the present invention, denaturation of L-ascorbic acid contained in a liquid extract from a plant can be prevented for a long time, and the content of L-ascorbic acid over time can be prevented. Reduction can be suppressed. In addition, since the decomposition of L-ascorbic acid due to heat is prevented, there is no loss during processing when used as an additive, and the efficiency of addition can be improved. Therefore, when a liquid extract containing L-ascorbic acid is added and processed as an additive for food or cosmetics, the L-ascorbic acid concentration does not decrease even during heat processing, so there are no restrictions during processing. In addition, it can be said that the additive is efficient by suppressing the quantitative loss during processing.
　特に、カムカム、アセロラ等、Ｌ－アスコルビン酸の含有量が高い植物においては、保存環境の影響を受けにくく、Ｌ－アスコルビン酸濃度を長期間保つことが可能となるので、Ｌ－アスコルビン酸の含有量を損なうことなく輸送可能となり、需要の増大が期待できる。 In particular, plants with a high L-ascorbic acid content, such as camcam and acerola, are less susceptible to the preservation environment and can maintain the L-ascorbic acid concentration for a long period of time. It can be transported without losing volume, and an increase in demand can be expected.

Claims (10)

  1. 果実や野菜を含む全ての植物から得られる液体抽出物が含有するＬ－アスコルビン酸を安定化させる方法であって、
    　当該液体抽出物と、ルチン及び／又はその誘導体を含む安定化溶液とを混合することにより、当該液体抽出物が含有するＬ－アスコルビン酸の酸化分解を抑制した調製液体抽出物とすることを特徴とするＬ－アスコルビン酸の安定化方法。     A method for stabilizing L-ascorbic acid contained in a liquid extract obtained from all plants including fruits and vegetables,
    By mixing the liquid extract with a stabilizing solution containing rutin and / or a derivative thereof, a prepared liquid extract in which oxidative degradation of L-ascorbic acid contained in the liquid extract is suppressed is obtained. A method for stabilizing L-ascorbic acid.
  2. 前記安定化溶液は、ルチン及び／又はその誘導体を０．５％ｗ／ｖ～１０％ｗ／ｖ含有するものを用いる請求項１に記載のＬ－アスコルビン酸の安定化方法。 The method for stabilizing L-ascorbic acid according to claim 1, wherein the stabilizing solution contains rutin and / or a derivative thereof at 0.5% w / v to 10% w / v.
  3. 前記安定化溶液は、アルカリ溶液又はエタノールと、ルチン及び／又はその誘導体とを混合させた混合溶液を用いる請求項１又は請求項２に記載のＬ－アスコルビン酸の安定化方法。 3. The method for stabilizing L-ascorbic acid according to claim 1, wherein the stabilizing solution is an alkaline solution or a mixed solution obtained by mixing ethanol and rutin and / or a derivative thereof.
  4. 前記安定化溶液の構成成分として、アルカリ溶液を用いる場合、アルカリ成分として水酸化カリウム又は水酸化ナトリウムを含有するアルカリ水溶液を用いるものである請求項３に記載のＬ－アスコルビン酸の安定化方法。 4. The method for stabilizing L-ascorbic acid according to claim 3, wherein when an alkaline solution is used as a component of the stabilizing solution, an alkaline aqueous solution containing potassium hydroxide or sodium hydroxide as the alkaline component is used.
  5. 前記アルカリ水溶液は、水酸化カリウム又は水酸化ナトリウムを０．２％ｗ／ｖ～０．８％ｗ／ｖの濃度で含有するものを用いる請求項４に記載のＬ－アスコルビン酸の安定化方法。 5. The method for stabilizing L-ascorbic acid according to claim 4, wherein the aqueous alkaline solution contains potassium hydroxide or sodium hydroxide at a concentration of 0.2% w / v to 0.8% w / v. .
  6. 前記安定化溶液は、ルチンを含有する植物から、水性アルコールによりルチンを抽出して得られる水性アルコール抽出物である請求項１又は請求項２に記載のＬ－アスコルビン酸の安定化方法。 3. The method for stabilizing L-ascorbic acid according to claim 1 or 2, wherein the stabilizing solution is an aqueous alcohol extract obtained by extracting rutin from a plant containing rutin with aqueous alcohol.
  7. 前記調製液体抽出物は、ルチン及び／又はその誘導体が０．０１％ｗ／ｖ～１％ｗ／ｖ濃度となるように含有させたものである請求項１～請求項６のいずれかに記載のＬ－アスコルビン酸の安定化方法。 The prepared liquid extract contains rutin and / or a derivative thereof at a concentration of 0.01% w / v to 1% w / v. Of the method for stabilizing L-ascorbic acid.
  8. 請求項１～請求項７のいずれかに記載のＬ－アスコルビン酸の安定化方法を用いて得られたことを特徴とするＬ－アスコルビン酸の安定化処理を施した調製液体抽出物。 A prepared liquid extract subjected to L-ascorbic acid stabilization treatment, which is obtained by using the method for stabilizing L-ascorbic acid according to any one of claims 1 to 7.
  9. 前記液体抽出物を固体状に加工して得られる固体状抽出物であって、
    　当該液体抽出物を請求項１～請求項７のいずれかに記載のＬ－アスコルビン酸の安定化方法を用いてＬ－アスコルビン酸の安定化処理を施した調製液体抽出物とし、これを固体状に加工して得られたことを特徴とするＬ－アスコルビン酸の安定化処理を施した固体状抽出物。     A solid extract obtained by processing the liquid extract into a solid,
    The liquid extract is a prepared liquid extract that has been subjected to L-ascorbic acid stabilization treatment using the L-ascorbic acid stabilization method according to any one of claims 1 to 7, and this liquid extract is in a solid state. A solid extract subjected to a stabilization treatment of L-ascorbic acid obtained by processing into
  10. 前記液体抽出物を半流動体状に加工して得られる半流動体抽出物であって、
    　当該液体抽出物を請求項１～請求項７のいずれかに記載のＬ－アスコルビン酸の安定化方法を用いてＬ－アスコルビン酸の安定化処理を施した調製液体抽出物とし、これを半流動体状に加工して得られたことを特徴とするＬ－アスコルビン酸の安定化処理を施した半流動体抽出物。     A semi-fluid extract obtained by processing the liquid extract into a semi-fluid,
    The liquid extract is a prepared liquid extract subjected to L-ascorbic acid stabilization using the method for stabilizing L-ascorbic acid according to any one of claims 1 to 7, and this is semi-fluidized. A semi-liquid extract subjected to a stabilization treatment of L-ascorbic acid, which is obtained by processing into a body.
PCT/JP2009/070049 2008-11-28 2009-11-27 Method for stabilizing l-ascorbic acid, liquid extraction preparation, solid extract, and semi-fluid extract WO2010061921A1 (en)

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