JP3065925B2 - Active oxygen species scavenger and anti-fading agent - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an active oxygen species scavenger effective for eliminating active oxygen species such as superoxide and hydroxyl radicals, as well as seafood, processed fishery products, processed livestock products, vegetables and fruits, etc. The present invention relates to an anti-fading agent which is effective for preventing discoloration (browning).

2. Description of the Related Art Living organisms efficiently obtain the energy necessary for survival by utilizing oxygen. However, in the process of converting oxygen into water in such energy metabolism, reactive oxygen species are generated as an intermediate. In general, as the reactive oxygen species, superoxide released by stimulation of macrophages and the like, hydroxy radical generated by radiation exposure and the like are known. These reactive oxygen species are generated due to external triggers such as excessive radiation or ultraviolet irradiation, intake of chemical substances and tobacco, and internal factors such as ischemia reperfusion, inflammation, stress, and aging. Reactive oxygen species generated in excess in the living body in this way generally have high chemical reactivity and easily react with neighboring components such as lipids, nucleic acids, and proteins in the living body, leading to oxidative reactions leading to various diseases. Cause obstacles.

[0002] Accordingly, active oxygen species eliminating substances having an activity of efficiently eliminating active oxygen species represented by superoxide and hydroxyl radicals are oxidatively degraded in living organisms or in components contained in foods, pharmaceuticals, agricultural chemicals and the like. And is expected to be practically used in the food industry, especially in the fields of processed fishery products, health foods, nutritional foods, as well as pharmaceuticals, agricultural chemicals and cosmetics. For this reason, various active oxygen species eliminating substances are mainly extracted from raw materials derived from natural products, and their applications are being studied. For example, superoxide dismutase (SOD), which is an enzyme protein that scavenges superoxide, has been studied for preparation from cattle and rats, and mannitol, tryptophan, formic acid, etc. have been described as having hydroxyl radical scavenging activity (for example, Yoshihiko Oyanagi, "SOD and Reactive Oxygen Species Preparation Agents-Their Pharmacological Effects and Clinical Applications", pp. 224-228,
Japan Medical Museum, 1989).

However, since SOD is an enzyme protein, it has poor stability against heat, pH, and the like. Further, in the case of oral administration, most of the administered enzyme is digested and excreted, and its execution power is extremely low. At present, there is almost no practical hydroxyl radical scavenger capable of efficiently scavenging a small amount of hydroxy radicals. Therefore, at present, it is difficult to industrially obtain these active oxygen species elimination agents in large quantities and stably.
Also, SOD usually has an erasing effect only on superoxide, and has no effect on hydroxy radicals. Similarly, mannitol has scavenging activity for hydroxyl radicals, but cannot scavenge superoxide. As described above, although stable supply of an active ingredient having an activity of erasing active oxygen species typified by superoxide and hydroxyl radical is desired, there has been almost no practical application to date.

On the other hand, seafood, processed marine products, processed livestock products,
The fading and browning of vegetables and fruits, etc., are contrary to the taste of consumers and reduce the commercial value irrespective of the freshness itself. For example, myoglobin contained in meat such as beef, tuna, and red fish such as bonito, is exposed to light in the air to form a meth in a very short time, and the iron atom in the myoglobin molecule changes from divalent to trivalent. The flesh color changes from bright red to dark brown. A red fish having an astaxanthin pigment on the body surface, such as a sea bream, loses color even during frozen storage due to the action of air, light rays, fatty acid-enzymes, etc., and its palatability is reduced like beef. This phenomenon is simply a change in pigments such as myoglobin and astaxanthin, and proceeds regardless of the freshness of the meat.
In vegetables and fruits, fading or browning occurs due to the action of enzymes contained therein. For example, carotenoid pigments contained in green and yellow vegetables are decomposed by the action of lipoxidase and peroxidase. Fruits, such as apples, bananas and apricots, which have polyphenol oxidases in their tissues, immediately turn brown when peeled and left to stand. Due to browning, palatability is significantly reduced and the commercial value is drastically reduced. In addition, carotenoids in vegetables are easily decomposed by light, heat, and the like, even if the enzyme is inactivated.

Conventionally, water-soluble discoloration inhibitors include reducing substances such as sodium L-ascorbate, gallic acid,
Tea leaf extracts (catechins) have been utilized, and the use of sodium nitrite or the like as a color former has only been attempted to maintain the color of foods and the like. However, when a reducing substance such as L-ascorbic acid is used alone, the substance itself is oxidized in a short period of time, so that the discoloration preventing effect is not very strong. Catechins have bitterness and astringency peculiar to the catechin itself, there is a limit on the amount of use in practical use, and there is a limit in the effect of preventing fading. Sodium sulfite has room for study on its safety.

[0006] Flax seeds are one of the natural products commonly used as food raw materials. Flax seed is a plant that has been cultivated for a long time. Even today, it is cultivated in a wide area of the world except under the equator and in extremely cold regions, and is important not only for oil but also as a fiber crop or a medicinal plant.
Flax seeds are used for food in some Eastern European and Russian regions, but linseed oil with a high linolenic acid content has high drying properties, so paints, printing inks, linoleum,
Linseed oil cake is widely used as a raw material for oil paper and the like, and is also used as feed protein for dairy cows, beef cattle, and sheep. In other words, flax seeds can be said to be plant materials that are relatively stably available and highly safe for the human body.

In recent years, attention has been paid to the physiological action of a lignan compound having two phenol groups as a characteristic substance of flax seeds. Here, the lignan compound is generally defined as a low-molecular-weight oxidative condensate of p-hydroxybenzenepropane units. Flax seeds are lignans Secoisolariciresinol (2,3-bis (3-me
thoxy-4-hydroxybenzyl) butane-1,4-diol, hereinafter SIL
May be abbreviated as aglycone, to which a plurality of sugars such as glucose are bonded.
-glycoside (hereinafter may be abbreviated as SDG) or Secoisolariciresinol mono-glycoside to which the sugar is singly bonded.
(Hereinafter sometimes abbreviated as SMG). S
DG and SMG have their chemical structures converted by the action of intestinal bacteria and the like present in living organisms such as mammals that feed on flax seeds or their defatted lees, and enterodiol and Ente have biological activity.
rolactone. It has been found that these substances have strong anticancer activity against breast cancer and colon cancer. It has been shown that flaxseed contains an extremely large amount of SDG and SMG compared to other edible plants, and it has been reported that it is effective to use this as a precursor of bioactive lignans. (Eg SCCunnane and LU
Thompson, Flaxseed in Human Nutrition, 21
9-236, AOAC press, 1995).

As described above, the usefulness of SDG and SMG contained in flax seeds as precursors of Enterodiol and Enterolactone has been mainly studied. However, this SDG, SMG and its sugar chain hydrolyzate S
3,4-bis (3-methoxy-4-h
Other physiological functions and their applications by ydroxybenzyl) tetrahydrofran (hereinafter sometimes abbreviated as MHBT) have not been known so far.

[0009]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel active oxygen species scavenger having a remarkable effect of eliminating active oxygen species such as superoxide and hydroxy radical. Another object of the present invention is to provide an anti-fading agent which is excellent in persistence of the anti-fading effect and high in safety.

[0010]

SUMMARY OF THE INVENTION According to the present invention, a specific lignan compound contained in flax seeds has an excellent action of eliminating active oxygen species and is also excellent as an anti-fading agent. For example, it was made based on the knowledge that the above problems could be solved efficiently. That is, the present invention provides an active oxygen species eliminating agent comprising a lignan compound represented by the following general formula (I) as an active ingredient.

[0011]

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(Wherein, R _{1 to} R ₄ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R ₅ and R ₆ are each independently a hydroxyl group or glucose;
One or more sugars selected from the group consisting of galactose and fructose, the sugar chain residue having 1-3 glycosidic bonds, or R ₅ and R ₆ together represent an oxygen atom. The present invention also provides an anti-fading agent comprising a lignan compound represented by the above general formula (I) as an active ingredient.

BEST MODE FOR CARRYING OUT THE INVENTION Among the lignan compounds represented by the general formula (I) used in the present invention, the compounds represented by the following general formula (II) are preferable, and the following structural formulas (II-a) and
Compounds selected from the compounds represented by (II-b), (II-c) and (II-d) are preferred.

[0013]

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(Wherein R ₇ and R ₈ are the same or different and each independently represents a hydroxyl group or one to three or more sugars selected from the group consisting of glucose, galactose and fructose having 1 to 3 glycosides) The sugar chain residue bonded, or R ₇ and R ₈ together represent an oxygen atom)

[0015]

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[0016]

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[0017]

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[0018]

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(In the formula, Glc represents a glucose residue and Gal represents a galactose residue.) The lignan compounds SDG and SM used in the present invention.
G or its sugar chain hydrolyzate, SIL, or its dehydrate, MHBT, can be synthesized by a chemical synthesis method, but can be easily prepared by, for example, the extraction method described below using linseed as a raw material. . Specifically, flax seeds are first crushed by a crusher such as a mixer, a blender, or a homogenizer. The flax seed used here can be used regardless of the production area such as domestic or Canadian, cultivation or oil pressing varieties, and can be used as a raw material regardless of the presence or absence of roasting or non-roasting treatment. Further, linseed crush or oil cake produced during the oil pressing step may be used as a raw material.
The obtained pulverized product may be a defatted product obtained by completely extracting and removing an oil component with a fat-soluble organic solvent such as n-hexane. Next, a lower alcohol capable of extracting SDG or SMG or a hydrate thereof is 1 to 10 times (v / wt) (v: capacity, wt: weight; )), Pulverization and extraction operations are repeated as necessary, and solids are removed by a conventional method such as decantation, centrifugation, or filtration. Removal by heating gives an alcohol extract. The alcohol extract is the SDG of the present invention.
And a mixture containing SMG.

The lower alcohol or a hydrate thereof used herein includes linear or side chain lower alcohols having 1 to 4 carbon atoms, such as methanol, ethanol, n-propanol, isopropanol and n-butanol, if necessary. Mix water and make alcohol concentration 30-100% (v / v)
, Preferably 40-100% (v / v), more preferably 40%
It is preferably adjusted to ~ 90% (v / v), most preferably 50-80% (v / v). At alcohol concentrations below 30% (v / v),
A sticky substance specific to flax seeds may be eluted, making subsequent operations difficult.

Incidentally, in order to remove fat-soluble impurities other than the lignan compound according to the present invention in the alcohol extract, the following solvent extraction treatment can be carried out. That is, water is extracted by adding a water-insoluble organic solvent 2 to 10 times (v / wt) of the alcohol extract, for example, chloroform or n-hexane, and then separating into two phases by centrifugation or the like. The organic phase is removed and the aqueous phase is concentrated to dryness. At this time, the target lignan compound such as SDG or SMG is concentrated on the aqueous phase side. If this is dried under reduced pressure and concentrated, an extract fraction (crude lignan glycoside concentrate) containing a large amount of SDG or SMG according to the present invention can be obtained. Each of the crude lignan glycoside concentrates thus obtained is a mixture of those represented by the structural formula (I), and the main component thereof is SDG represented by the structural formula (II-a) or (II-b) And SMG
It is.

The components of the alcohol extract and the crude lignan glycoside concentrate can be fractionated and purified using an adsorbent such as silica gel or octadecyl silica (ODS), if necessary. That is, for example, OD
After preparing a column packed with S and equilibrating the column with water, the alcohol extract or the crude lignan glycoside concentrate was supplied at a load of 0.1 to 5% (wt / v), and a hydroalcoholic solvent (alcohol) was used. , Methanol, ethanol, n-propanol, isopropanol, n-butanol, etc.) and a predetermined fraction is eluted by a stepwise elution method or a continuous elution method in which the alcohol concentration is gradually increased. The eluted fraction obtained here can be further subjected to high-performance liquid chromatography (HPLC) using the adsorbent, preparative liquid chromatography, or the like, if necessary, to further purify each component to higher purity. . In the present invention, a water-soluble lignan compound such as SDG or SMG is thus obtained,
As the lignan compound, any of the alcohol extract, crude lignan glycoside concentrate or highly purified product can be used, or a mixture thereof can be used.

Next, SIL and MH were obtained from the alcohol extract or crude lignan glycoside concentrate obtained from flax seeds.
A method for preparing BT will be described. The alcohol extract or crude lignan glycoside concentrate contains SDG or SMG.
Is contained in a large amount, so that the SIL or MHBT represented by the structural formula (II-c) or (II-d) can be easily converted from SDG or SMG by hydrolysis using an enzyme or an acidic substance. Obtainable. However, MH
BT is a dehydrate produced secondarily from SIL by an acid hydrolysis reaction, and is a component that cannot be obtained by an enzymatic hydrolysis reaction. The alcohol extract or crude lignan glycoside concentrate is dispersed in water or a suitable buffer, and sugar chain hydrolases such as β-glucosidase and cellulase, α-glucosidase, β-galactosidase, α-galactosidase, amylase, One or more glycosidases such as glucuronidase are added, or these enzyme agents are immobilized on a suitable carrier such as activated carbon or celite, and subjected to continuous use and recovery and reuse at 10 to 60 ° C.
In contact with the enzyme for 1 to 48 hours, the sugar chain of SDG or SMG is cleaved by the action of the enzyme, or the alcohol extract or crude lignan glycoside concentrate to hydrochloric acid, sulfuric acid,
What is necessary is just to heat at 50-200 degreeC in the presence of acids, such as phosphoric acid and an organic acid, for 30 minutes to 5 hours. Since SIL or MHBT produced from SDG or SMG is a lipophilic lignan compound, n-hexane, chloroform and ethyl acetate, which are poorly soluble in water with a low-polarity organic solvent from an enzyme or acid hydrolysis reaction solution, are used. Can be efficiently extracted. The crude lignan concentrate can be obtained by concentrating the extracted organic solvent phase.

If necessary, SIL or MHBT can be fractionated and purified using an adsorbent such as silica gel or octadecyl silica (ODS). That is, each component can be subjected to high-performance liquid chromatography (HPLC), preparative liquid chromatography, or the like to purify each component with even higher purity. In the present invention, the fat-soluble crude lignan concentrate, SIL or MHBT thus obtained can be used as they are or as a mixture.

The active ingredient of the present invention, SDG or S
The method for generating and extracting MG, SIL or MHBT is not limited to the methods described above. Furthermore, the raw materials of the extract containing these active ingredients as main components are not limited to flaxseed or roasted product thereof, crushed product thereof and defatted lees, and natural materials containing SIL which is a kind of the present invention described above. All raw materials such as larch heartwood and parana pine resin can be used (for example, JP-A-7-2571).
No. 9). On the other hand, as a method for synthesizing a glycoside by adding a sugar chain to a compound containing a hydroxyl group, for example, a biochemical method utilizing the action of a glycosyltransferase or a chemical method utilizing a metal catalyst are generally used. ing. Using SDG as a raw material, lignan glycosides in which the sugar species or the number of sugars are arbitrarily changed as required can be synthesized.

That is, for example, when a biochemical method utilizing the action of a glycosyltransferase is used, glycosidases which are enzymes having glycosyltransferase activity, for example, β-glucosidase,
α-glucosidase, β-galactosidase, α-galactosidase, cyclodextrin synthase, β-fructofuranosidase, cellulase, amylase, etc. can be used alone or in combination, and the sugar donor is a monosaccharide such as glucose or galactose. , Cellobiose, disaccharides such as sucrose, oligosaccharides such as raffinose,
Alternatively, polysaccharides and the like can be used. However, when limiting the sugar species constituting the sugar chain of the glycoside, it is necessary to appropriately select the glycosyltransferase and the sugar donor accordingly. These glycosyltransferases and sugar donors are added to the concentrate or purified product containing SIL, and dissolved in a buffer or water.
The reaction is carried out at 6060 ° C. under heating or at room temperature for 1 to 100 hours. Extraction and purification of lignan glycosides from the reaction solution
The above-mentioned partition extraction method, column fractionation and preparative HPLC can be used, and a concentrate and a purified product having the target lignan glycoside can be obtained.

The active oxygen species erasing agent and the anti-fading agent of the present invention may be composed of the above-mentioned lignan compound alone, or may be composed of the above-mentioned lignan compound as an active ingredient, and a composition of these active ingredient and a suitable diluent or carrier. It may be in the form of an object. Examples of such diluents or carriers include
For example, gum arabic, xanthan gum, dextrin,
A solid diluent or carrier such as cyclodextrin, starch, glucose, sucrose, lactose, xylose, galactooligosaccharide, xylo-oligosaccharide; and a liquid diluent or carrier such as water, ethanol, propylene glycol, glycerin, emulsifier, etc. It can be a composition comprising two or more species.

Among the emulsifiers, those suitable as lipophilic emulsifiers include various commercially available glycerin fatty acid esters, propylene glycol fatty acid esters, sorbitan fatty acid esters, sucrose fatty acid esters, polyglycerin fatty acid esters, pentaerythritol fatty acid esters, polyoxyethylene sorbit. Fatty acid esters, polyoxyethylene glycol fatty acid esters, polyoxyethylene alkyl ether, polyoxyethylene phenyl ether, polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, lecithin, and the like. As the hydrophilic emulsifier, various commercially available anionic, nonionic, cationic, and amphoteric emulsifiers can be used.

Examples of the anionic emulsifier include soap N
Carboxylic acid salts such as acylamino acid salts, alkyl ether carboxylic acids, acylated peptides, alkyl sulfonates, alkyl benzene sulfonates, alkyl naphthalene sulfonic acids, and formalin condensates thereof, dialkyl sulfosuccinate salts, α-olefin sulfones Acid salts, sulfonates such as N-acylmethyl taurine, sulfated oils, sulfates such as alkyl sulfates, alkyl ether sulfates, alkyl allyl ether sulfates, alkylamide sulfates, alkyl phosphates, alkyl phosphates Phosphate salts such as ether phosphates and alkyl allyl ether phosphates are exemplified.

Examples of the nonionic emulsifier include polyoxyethylene alkyl ether, polyoxyethylene secondary alcohol ether, polyoxyethylene alkyl phenyl ether, ethylene oxide derivative of alkylphenol formalin condensate, and polyoxyethylene polyoxypropylene block polymer. Such as ether type surfactants, polyoxyethylene glycerin fatty acid esters,
Polyoxyethylene castor oil and hydrogenated castor oil, ether ester surfactants such as polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, polyoxyethylene glycol fatty acid ester, fatty acid monoglyceride, sorbitan fatty acid ester, sucrose fatty acid Examples include ester-type surfactants such as esters and polyglycerin fatty acid esters, and nitrogen-containing surfactants such as fatty acid alkanolamides, polyoxyethylene fatty acid amides, polyoxyethylene alkylamines, and alkylamine oxides. Examples of the cationic emulsifier include an alkylamine salt, a quaternary ammonium salt, a benzalkonium salt, a pyridinium salt, and the like.
For example, carboxybetaine type, aminocarboxylate, imidazolinium betaine, lecithin and the like can be mentioned.

The active oxygen species scavenger of the present invention may be formulated as an oral or parenteral product in the above-mentioned form or further together with auxiliaries and additives, as food or drink, processed fishery products, cosmetics, quasi-drugs, It can be used in the fields of pharmaceuticals, pesticides and the like. In addition, the amount of addition is not uniformly defined depending on the type and form of the target product, but in the case of an alcohol extract, 100 ppm to 100,000 ppm, more preferably 1,000 ppm to
100,000 ppm, in the case of crude lignan glycoside concentrates and crude lignan concentrates from 10 ppm to 50,000 ppm, more preferably
100ppm ~ 10,000ppm, 0.1p for highly purified product
It is preferred that the amount be from pm to 10,000 ppm, more preferably from 1 ppm to 1,000 ppm. On the other hand, the anti-fading agent of the present invention may contain, if desired, a conventionally known anti-fading agent or synergist in addition to the above-mentioned active ingredients. Examples of the lignan compound represented by the above formula, an anti-fading agent that can be blended or used in an oil extract (oil cake, defatted product) or an alcohol extract obtained from flax seeds include ascorbic acid, sodium ascorbate, erythorbic acid, and erythorbic acid. Examples thereof include sodium, gallic acid, propyl gallate, ascorbic acid palmitate, and ascorbic acid stearate, and one or more compounds can be used. Of these, L-
It is preferable to use ascorbic acid or a salt thereof. As a synergist that can be used in combination with oil extract or alcohol extract obtained from flax seeds, sodium polyphosphate,
Potassium polyphosphate, Sodium metaphosphate, Potassium metaphosphate, Citric acid, Trisodium citrate, Potassium citrate, Malic acid, Disodium malate, Potassium malate, Tartaric acid, Disodium tartrate, Potassium tartrate, Fumaric acid , Disodium fumarate, dipotassium fumarate, adipic acid, disodium adipate,
Dipotassium adipic acid, monoglyceride citrate, monoglyceride malate, monoglyceride tartrate, monoglyceride fumarate, monoglyceride adipic acid, tocopherol, and the like can be used, and one or more of them can be used. The concentration of the active ingredient in the composition is not strictly limited, but is usually about 0.1 to about 40% by weight.
Is preferably within the range. Further, the anti-fading agent can be prepared in any dosage form, for example, powder, granule, liquid, emulsion, paste or any other dosage form.

The target which can be prevented from fading using the anti-fading agent of the present invention is, for example, in the case of seafood, the body of red fish such as tuna, salmon, and trout, the surface of red fish such as snappers, and shrimp. Crustaceans such as crabs, octopus, mollusks such as squid, scallops,
In the case of processed fishery products such as shellfish such as abalone and red mussels, fish sausage, kamaboko, bamboo rings, salted fish, dried fish, etc.
In the case of processed livestock products, meat, ham, sausage, etc., vegetables, such as carrots, peppers, lettuce, cabbage, etc., in the case of fruits, apples, grapes, various juices such as oranges, prevention of blackening of bananas, etc. it can. The amount of the anti-fading agent of the present invention added to the above-mentioned fish and shellfish, processed marine products, processed livestock products, vegetables and fruits, when the alcohol extract is used alone, is 10 ppm to 100,000 ppm by direct administration, and preferably 50 ppm to 50 ppm. 50,000ppm, 100ppm ~ by indirect administration such as immersion
It is used as a 200,000 ppm solution, desirably a 500 ppm to 100,000 ppm solution. When the above crude lignan glycoside concentrate or crude lignan concentrate is used alone, it can be administered directly.
1 ppm to 100,000 ppm, preferably 5 ppm to 50,000 ppm, for indirect administration 10 ppm to 200,000 ppm, preferably 50 ppm to 100,0
It is good to be 00 ppm. When a high-purity purified product is similarly used, 0.1 ppm to 100,000 ppm by direct administration, desirably 1 p
It is preferably from pm to 50,000 ppm, from 1 ppm to 200,000 ppm for indirect administration, preferably from 10 ppm to 100,000 ppm. The anti-fading agent of the present invention includes the oil extract obtained from the flax seed or the roasted product thereof, the concentrate and the purified product thereof, and the oily cake of the flax seed or the roasted product in addition to the hydrolyzate thereof. You may add as it is. In the case of using crushed cake alone, it is desirable to add 5 to 10 times the amount of the alcohol extract, and the upper limit is 100,000 ppm. Although a long-lasting anti-fading effect can be obtained with the addition amount of several hundred ppm, there is no bitterness or astringency like catechin, etc., and it is also highly safe as a food material. Absent. If the amount is less than the above-mentioned amount, the effect of preventing discoloration is weak. In the case of an alcohol extract, even if it is added in excess of 200,000 ppm, no viscosity occurs, but no further effect commensurate with the added amount can be expected.

[0033]

According to the present invention, there is provided an active oxygen species scavenger having an activity capable of simultaneously and effectively scavenging superoxide and hydroxyl radicals. Further, the anti-fading agent of the present invention has a far more powerful anti-fading effect as compared with currently used ascorbic acid and the like, and is also excellent in terms of sustained efficacy. Further, it is excellent in that it does not affect the flavor of the added foodstuff in a tasteless and odorless manner. Next, the present invention will be described with reference to examples.

【Example】

Example 1 After crushing 1000 g of Canadian flax seeds in a blender,
A 3-fold amount (v / wt) of n-hexane was added, and the mixture was refluxed at 60 ° C. for 3 hours to perform extraction. 50% of the defatted lees obtained after filtration
g in air and add 3 times (v / wt) alcohol concentration:
80% by weight (hereinafter abbreviated as%) of aqueous methanol was added, and the mixture was refluxed at 60 ° C. for 5 hours and extracted. After cooling, the whole was filtered, and the filtrate was concentrated to dryness to obtain 70 g of a methanol extract.

Example 2 30 g of the methanol extract obtained in Example 1 was
Was used repeatedly as a carrier for partition chromatography. That is, 60 g of YMC-GEL (manufactured by YMC Co.) ODS-A was packed in a glass column having a diameter of 3 cm and a length of 50 cm, and equilibrated by flowing water. This was loaded with a methanol extract at the top of the column. The target substance was eluted by a step elution method in which the methanol concentration was sequentially increased from water. Fractions eluted with 30-70% (v / v) methanol-containing solvent were collected and concentrated under reduced pressure to give
4.5 g of crude lignan glycoside concentrate were obtained. This was repeatedly subjected to preparative HPLC, and purification was performed until SDG and SMG became single. As a result, each purified product of 350 mg of the purified SDG represented by the structural formula (II-a) and 30 mg of the purified SMG represented by the formula (II-b) was obtained. Preparative HPLC was performed under the following conditions. The HPLC system uses a pump (CCPM,
Tosoh Co., Ltd.) column (Soken Kagaku Co., Ltd., Soken
Pak) ODS-W 5μ, 10x250mm), UV absorption detector (Tosoh Corp., UV-8000) connected, elution was performed with water:
Using a linear gradient in which methanol becomes 50:50 to 40:40 after 40 minutes, the flow rate is 5 mL / min, and the detection wavelength is 280 nm.
And In addition, the analysis of the sugar species and the number of sugars was performed as follows (the same applies hereinafter).

Analysis of sugar species 1 mg each of purified SDG or SMG and 0.1 mg of β-glucosidase (derived from almond, manufactured by Sigma) were dissolved in 1 mL of 50 mM acetate buffer (pH 5.0), and the mixture was dissolved at 50 ° C. for 24 hours. Heated. After adding 1 mL of ethyl acetate and shaking extraction, the ethyl acetate phase was removed, and the aqueous phase was subjected to a pretreatment filter for HPLC (pore size 0.2 μm).
m, Mysolidisc W-13-2, manufactured by Tosoh Corporation), and the filtrate was added with 5 mL of acetone and concentrated to dryness under reduced pressure. After adding 0.2 mL of TMS-PZ (manufactured by Tokyo Kasei Kogyo Co., Ltd.) as a trimethylsilylating agent, and allowed to stand at room temperature for 30 minutes, 1 μL thereof was analyzed by gas chromatography under the following conditions. The analysis conditions are as follows. Gas chromatograph, HEWLETT PACKARD 5890; Column, DB-1701 (15m ×
0.25mm, Film Thickness, 1.0μm, J & W SCIE
NTIFIC); injection method, split method (split ratio 1/50); column temperature, 180 ° C; carrier gas, He. Commercially available glucose, galactose and fructose were used as standards, and the sugar species constituting each glycoside were analyzed.

Analysis of sugar number 1 mg of each purified SDG or SMG was dissolved in 1 mL of water,
Some of them were subjected to molecular sieve chromatography to estimate the molecular weight of each. The analysis conditions of molecular sieve chromatography are as follows. Column: TSK-gel G25
00PWXL (manufactured by Tosoh Corporation) × 2, eluent: 50 mM-NaNO ₃
Aqueous solution, flow rate; 0.8 mL / min, detector; refractometer and ultraviolet detector. Cellobiose, raffinose,
Oligosaccharides such as stachyose, cellopentaose, and cellohexaose were similarly analyzed to prepare a standard curve of molecular weight and retention time, and then used to estimate the molecular weight of the lignan glycoside.

Example 3 To 20 g of the methanol extract obtained in Example 1 was added 1 L of a 1N hydrochloric acid solution, and the mixture was refluxed at 100 ° C. for 1 hour. After allowing to cool, 1 L of ethyl acetate was added to perform partition extraction. The ethyl acetate phase was concentrated to dryness to obtain 450 mg of an ethyl acetate extract. This was repeatedly subjected to preparative HPLC, and purification was performed until SIL and MHBT became single. As a result, the structural formula (II
120 mg of the purified SIL represented by -c) and 50 mg of the purified MHBT represented by (II-d) were obtained. Preparative HPLC was performed in the same manner as in Example 2.

Example 4 20 g of the methanol extract obtained in Example 1 and β-glucosidase (derived from almonds, manufactured by Sigma) as a commercially available enzyme preparation, cellulase (derived from Trichoderma viride, Boehringer Mannheim Yamanouchi Co., Ltd.) Made, 1g each
1 L of 50 mM acetate buffer (pH 5.0) was added to
For 24 hours. After allowing to cool, 1 L of ethyl acetate was added to perform partition extraction. The ethyl acetate phase was concentrated to dryness to obtain 500 mg of an ethyl acetate extract. This was repeatedly subjected to preparative HPLC, and purification was performed until the fraction components became single. As a result, the purified SIL 20 represented by the structural formula (II-c)
0 mg was obtained.

Example 5 One unit of commercially available α-galactosidase (manufactured by Seikagaku Corporation) was added to 1 mL of an acetate buffer (pH 5.0) containing 100 mg of purified SDG and 100 mg of galactose.
Allowed to react for hours. After the reaction solution was boiled for 10 minutes to inactivate the enzyme, the reaction solution was repeatedly subjected to partition chromatography using ODS as a carrier as described in Example 2. In addition to SDG as a substrate, at least three new ultraviolet absorbing components A, B and C eluted in fractions having higher polarity than SDG. Each of these components was further purified by preparative HPLC under the conditions described in Example 2, and as a result, each purified product A (about 2 m
g), B (about 5 mg) and C (about 10 mg) were obtained. The purified products of A, B and C were subjected to analysis of aglycone and sugar by acid hydrolysis, analysis of sugar by enzymatic hydrolysis by β-glucosidase and α-galactosidase, and estimation of molecular weight by molecular sieve chromatography. In addition, the analysis conditions of the molecular sieve chromatography were performed as follows. Column: TSK-gelG2500PWXL (manufactured by Tosoh Corporation) ×
2. Eluent: 50 mM-NaNO ₃ aqueous solution, flow rate: 0.8 mL / min, detector: refractometer and ultraviolet detector. As a standard, oligosaccharides such as raffinose and stachyose were similarly analyzed,
A standard curve of molecular weight and retention time was created and estimated. As a result of each analysis, component A has (A-1) a SIL skeleton as aglycone, (A-2) equimolar production of glucose and galactose by acid hydrolysis,
(A-3) that monosaccharide glucose and two components of trisaccharide are produced in equimolar amounts when hydrolyzed with β-glucosidase; (A-4) that only galactose is produced when hydrolyzed with α-galactosidase; (A-5) It was revealed to be a tetraglycoside.

From the above, the component A is represented by the structural formula III-a
It was suggested that this is a novel lignan glycoside represented by Similarly, component B is (B-1) aglycone as SIL
Having a skeleton, (B-2) producing equimolar amounts of glucose and galactose by acid hydrolysis, (B-3)
hydrolyzing with β-glucosidase to produce only disaccharide consisting of glucose and galactose, (B-4)
Hydrolysis with α-galactosidase produces only galactose; (B-5) tetraglycoside. From the above, component B was suggested to be a novel lignan glycoside represented by the structural formula III-b. Component C is (C-
1) having an SIL skeleton as an aglycone, (C-
2) Glucose and galactose by acid hydrolysis:
(C-3) that when hydrolyzed with β-glucosidase, only two components, glucose, which is a monosaccharide, and disaccharide consisting of glucose and galactose are generated, (C-4) α -Only galactose is produced by hydrolysis with galactosidase, (C-5) triglycoside. From the above, the component C is represented by the structural formula III-c
It was suggested that this is a novel lignan glycoside represented by In the formula, Glc represents a glucose residue, and Gal represents a galactose residue.

[0041]

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[0042]

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[0043]

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Example 6 The superoxide scavenging activity was determined according to the method described by Naoshi Kaneda and Nobuo Ueda, "Experimental Method for Lipid Peroxide", pp. 136-154, published by Itoyaku Shuppan Co., Ltd., 1993. Was measured as follows. Sodium hydrogen carbonate buffer (pH 10.2)
50 μL of 1 mg / m LEDTA solution in 1.2 mL, 50 μL of 1.5 mg / mL bovine serum albumin (BSA) solution, 0.6 mg / m
L Nitro blue tetrazolium (NBT) solution 50μL,
A solution containing 50 μL of a 0.5 mg / mL xanthine solution. A predetermined amount of the alcohol extract described in Example 1, the crude lignan glycoside concentrate described in Example 2, SDG or SMG, described in Example 3. After dissolving and mixing SIL, MHBT, each purified product of components A to C described in Example 5, or t-butylhydroxyanisole (BHA) as a commercially available antioxidant, the mixture was allowed to stand at 25 ° C. for 10 minutes. . To this was added 50 μL of an 8 mg / mL xanthine oxidase (derived from buttermilk, manufactured by Wako Pure Chemical Industries, Ltd.), and the mixture was stirred and allowed to stand at 25 ° C. for 20 minutes. After adding 50 μL of 1 mg / mL copper chloride aqueous solution to stop the enzymatic reaction, the absorbance value (A) at 560 nm was measured.
A sample to which only the same amount of buffer was added instead of the sample solution was used as a control solution, and the absorbance was measured in the same manner as a sample blank in which the order of addition of the aqueous copper chloride solution and the sample solution was reversed,
The respective values were B and b. The superoxide erasure rate was calculated from the following equation. Superoxide erasure rate (%) = {1− (A−b) / B} × 100. The erasing activity at which the superoxide erasure rate becomes 50% is 1 unit (1 unit).
unit). As shown in Table 1, the higher the activity value, the stronger the scavenging effect. However, the added alcohol extract and purified product all show a remarkable superoxide scavenging effect. For example, 1 μmol of SIL was purified. With the addition of the substance, the erasing activity was at least twice as high as that when BHA was added. Therefore, the SDG and SM related to the present invention
Extracts, concentrates and purified products containing G, SIL or MHBT as the main components were all found to have strong superoxide scavenging activity.

[0045]

Table 1 Table 1 スー パ ーSample Superoxide scavenging activity (units) alcohol extract 4.5 Crude lignan Glycoside concentrate 15.0 Component A 31.5 Component B 31.0 Component C 30.6 SDG purified 31.0 SMG purified 33.5 SIL purified 32.9 MHBT purified 35.8 BHA 12. 8 Note) In the case of alcohol extract or crude lignan glycoside concentrate, 1 mg is shown in the reaction system, and each purified product and BHA show the activity value when 1 μmol is present.

Example 7 The hydroxy radical scavenging activity was measured as follows.
The reaction system used in this example generates a hydroxy radical by the Fenton reaction, and malondialdehyde (MDA) generated by the reaction between the hydroxy radical and a fatty acid.
Is reacted with thiobarbituric acid to measure the thiobarbituric acid-MDA adduct formed. That is, a predetermined amount of the alcohol extract described in Example 1, the crude lignan glycoside concentrate described in Example 2,
SDG or SMG, SIL or MHB described in Example 3
T, purified components A to C described in Example 5 were combined with linoleic acid (2 mg / mL) and sodium dodecyl sulfate (SDGS).
2 mg / mL) and dissolved in 0.92 mL of 30 mM Trishydroxymethylaminomethane hydrochloride buffer (pH 7.4), and 0.04 mL of a 2.5 mM hydrogen peroxide solution and 0.04 mL of a 2.5 mM iron (II) chloride solution.
L was added and heated to 37 ° C. for 15 hours. The extract, concentrate and purified product containing the active substance shown in the present invention, which was reacted similarly without containing the same, was used as a control. After heating, t-
0.01 mL of an ethanol solution containing 12 mg / mL of butylhydroxyl toluene (BHT) was added. TBA 12mg and SD
Dissolve 16.2 mg of GS in 2.3 mL of distilled water and add 20% (v / v
) 1.5 mL of acetate buffer (pH 4.0) and 0.2 mL of the above reaction solution
Was added and heated at 95 ° C. for 1 hour. After cooling, the absorbance at 532 nm was measured. The absorbance of the control was B and the absorbance of the reaction solution containing each sample was A, and the hydroxyl radical scavenging rate was calculated from the following equation. Hydroxyl radical scavenging rate (%) = {1− (BA) / B} × 100. As shown in Table 2, the higher the scavenging rate, the stronger the scavenging action, but both the added extract and the purified product show a remarkable hydroxy radical scavenging action, for example, 0.
Approximately 70% had been eliminated by the addition of 01 μmol of purified SIL. This effect is far superior to that of α-tocopherol, and the effects of the SDG, SMG, SIL or MH
BT-based extract, concentrate or purified product
It was found to have strong hydroxyl radical scavenging activity.

[0047]

[Table 2] Table 2 ───────────────────────────── Sample Hydroxy radical scavenging rate (%) Alcohol extract 60.5 Crude lignan Glycoside concentrate 90.0 Component A 66.0 Component B 67.7 Component C 68.8 SDG purified 40.2 SMG purified 45.2 SIL purified 68.5 MHBT purified 70.3 α-tocopherol (0.01 μmol) 0.0 α-tocopherol (0.1 μmol) 10.5 Note) In the case of alcohol extract or crude lignan glycoside concentrate, 0.1 mg / mL in the reaction system, 0.01 μM / mL for each purified product, and α-tocopherol when 0.01 μM / mL or 0.1 μM / mL were present. Shows the amount of activity.

Example 8 Formulation of finely pulverized product Oil cake of flax seeds (water content 8.0% by weight, oil content 0.9% by weight)
Or milling the flax seed roasted flax (water content 7.8% by weight, oil content 2.7% by weight) with a fine pulverizer (Hosokawa Micron Co., Ltd.)
(AP-B), 100% of which passed through a 50-mesh sieve and 60% passed through a 100-mesh sieve to prepare a fine powder anti-fading agent. Example 9 Extract preparation Formulated flaked oil cake of roasted flax seed (water 7.8% by weight, oil content 2.7% by weight) was added with 200mL of 30, 50, and 90% by weight of ethanol, respectively, and extracted at 60 ° C for 5 hours. And filtered. The solvent of this extract was removed under reduced pressure by a rotary evaporator to obtain 2.4, 2.3, and 0.9 g of a solid substance, respectively, to obtain a discoloration inhibitor comprising a water-containing ethanol extract.

Example 10 Concentrate preparation The method described in Example 2 was repeated to obtain the above-mentioned structural formula (II-a)
And S represented by the structural formula (II-b)
About 8.5 g of a crude lignan glycoside concentrate containing MG was obtained, and an anti-fading agent comprising the concentrate was obtained. Example 11 Hydrolyzate preparation To 1 g of an extract preparation (50% ethanol extract) obtained by the method described in Example 9, 1 L of 1N hydrochloric acid was added, and the mixture was hydrolyzed at 100 ° C for 1 hour. After returning this to room temperature, ethyl acetate was added.
Add 1L and mix well. After recovering the ethyl acetate layer and removing the solvent,
There was obtained a category mainly containing a sugar chain hydrolyzate of a lignan glycoside (SMG, SDG, etc.). 20 more salad oil
g was added to dissolve the hydrolyzate to produce an oil-soluble hydrolyzate preparation, a discoloration inhibitor.

Example 12 Mixed composition 1 (powder) 40% of the extract preparation of Example 9 (50% ethanol extract)
An anti-fading agent, which was a powder composition comprising 40% dextrin and 20% citric acid, was prepared. Example 13 Mixed composition 2 (liquid) 30% of the extract formulation of Example 9 (50% ethanol extract)
An anti-fading agent, which is a liquid composition comprising 63% glycerin and 7% citric acid, was prepared.

Example 14 Mixed composition 3 (powder) The extract preparation of Example 9 (50% ethanol extract) 60%
An anti-fading agent as a powder composition comprising 40% sodium L-ascorbate was prepared. Example 15 Mixed composition 4 (oil-soluble) 15 g of the extract preparation of Example 9 (50% ethanol extract),
After 3 g of citric acid was dissolved in 10 g of water while heating, 10 g of tocopherol, 30 g of glycerin fatty acid monoester and 32 g of salad oil were added, and the mixture was stirred with a homomixer for 5 minutes to obtain 100 g of a lipophilic anti-fading agent.

Test Example 1 Test for Preventing Discoloration of Tuna After 100 g of frozen tuna was thawed, the finely pulverized product preparation and extract preparation of the present invention described in Examples 8 and 9 (50% by weight)
Ethanol extract) and 2 L of an aqueous solution containing 1.0% each of sodium L-ascorbate were prepared. Further, 2 L each of an aqueous solution containing 0.1% of the crude lignan glycoside concentrate described in Example 10 and an aqueous solution containing 0.1% of the lignan glycoside hydrolyzate described in Example 11 were prepared. The tuna meat was immersed in each aqueous solution for 1 minute at 0 ° C. (1 kg of tuna can be treated with 2 L of each aqueous solution). Thoroughly wipe off the dipped material,
Stored at 5 ° C. with untreated material. Over time, the effect of preventing fading was compared by a color difference meter and sensory evaluation.
The results are shown in Table-3.

[0053]

Table 3 Effect of preventing fading on tuna Color difference meter (a value) 0hr 12hr 24hr raw material 8.38 7.38 6.34 extract preparation 8.51 8.35 8.07 Roughness lignan glycosides concentrate formulation 8.79 8.47 8.20 finely pulverized product formulation 8.55 8.30 7.91 lignan glycosides hydrolyzate 8.68 8.40 8.21 Ascorbic Sodium acid 8.77 7.62 6.45 Note) The a value indicates the intensity of redness.

As a result of measuring the color difference, as shown in the above table, the samples (4 types) treated with the product of the present invention exhibited a bright red color, whereas the untreated sample and sodium L-ascorbate were added. The sample had turned dark brown. In addition, as a result of the sensory evaluation by 20 panelists, no problems were recognized in the flavor and taste of the tuna treated with the product of the present invention.
From the above results, the effectiveness of the product of the present invention for preventing fading was confirmed. Test Example 2 Test for Preventing Discoloration of Carrots Raw carrots were sliced to a thickness of 0.5 to 3.0 mm, and the extract preparation and the mixed composition as the anti-fading agents according to the present invention described in Examples 9, 12, 13 and 14 were mixed. The mixture was subjected to blanching treatment for 5 minutes in each aqueous solution containing 0.5% of each product and in the aqueous solution containing 0.05% of the lignan glycoside hydrolyzate obtained in Example 11. The control performed the same process using water. Next, the water was cut well and freeze-dried. After drying completely, it was stored at 25 ° C. under fluorescent irradiation (5000 Lux). Ten days after the start of storage, the state of fading was examined.
The results are shown in Table-4 and Table-5.

[0055]

Table 4 Table 4 Anti-fading effect on carrots Test area Carrot surface color control Intense fading and significant whitening. Extract preparation Partly whitish, but retains good color tone. Lignan glycoside Partially whitish, but retains good color. Hydrolyzate Mixed composition 1 Partly whitish, but retains good color. Mixed composition 2 Partly whitish, but retains good color tone. Mixed composition 3 Good color development and maintains vivid orange.

[0056]

[Table 5] Table 5: Anti-fading effect on carrots ───────────────────────────── Test section Color difference meter (a value) 0 Day 10 day control 25.81 2.41 Extracted formulation 25.18 17.33 Hydrolyzate of lignan glycoside 25.43 17.78 Mixed composition 1 25.55 16.77 Mixed composition 2 25.31 13 .51 mixed composition 3 25.22 21.18

As described above, it was clarified that the extract preparation and the mixed composition according to the present invention have an effect of preventing discoloration of carrots. In each case, a synergistic effect with sodium L-ascorbate was observed in the extract preparation, the mixed compositions 1, 2 and 3 described above. Test Example 3 Discoloration Prevention Test for Orange Juice The pulp of Satsuma mandarin was sampled, passed through a juicer, and filtered with filter paper to collect the juice. To this juice, the extract preparation according to the present invention described in Example 9 was added so as to contain 0.5%. Further, the crude lignan glycoside concentrate preparation of the present invention described in Example 10 was added to the juice so as to contain 0.05%. These samples were mixed with the juice without the formulation.
A storage test was performed for 3 days under irradiation of a fluorescent lamp at 10 ° C. and 5000 Lux. As a result, the additive-free juice faded,
The juice to which the product of the present invention was added retained a preferable orange color.

Test Example 4 Test for preventing fading of beef Frozen beef was sliced and then thawed in a refrigerator. Example 8
And 2.5% of any of the pulverized product preparation and extract preparation (50% ethanol extract) according to the present invention described in 9 and 9
Each 0 ° C. aqueous solution was prepared and sprayed at 5 mL per 100 g of sliced beef. We wipe off moisture well,
Stored at 5 ° C. for 5 days. As a result, the non-added beef turned dark brown, while the beef to which the product of the present invention was added maintained a preferable meat color. Test Example 5 Test for preventing fading of minced fresh tuna meat for leeks After thawing frozen tuna crust and crushing it with a food cutter, 8% salad oil was added to the tuna meat and mixed well, and used for leeks. Minced fresh tuna meat (hereinafter simply referred to as "Negi-toro") was prepared. A sample obtained by adding 0.1 g of either the hydrolyzate preparation and the mixed composition 4 or sodium L-ascorbate according to the present invention described in Examples 11 and 15 to 100 g of Negitro, and a sample having no anti-fading agent. Prepare three types of leek, 8 ° C, 3
A storage test was performed for one day. The color difference was measured over time to check the fading, and the sensory evaluation was performed. Table 6 shows the results.
Shown in

[0059]

[Table 6] Table 6: Effect of preventing fading on Negitro Color difference meter (a value) 0 day 1 day 3 days Untreated 10.01 7.61 4.76 Hydrolyzate preparation 9.97 9.28 7.99 Mixed composition 4 9.88 9.30 8.11 Sodium ascorbate 10.11 8.86 4.18

From the above results, it was found that Negitro containing the product of the present invention had a good color tone, and the product of the present invention had a good effect of preventing fading. In addition, as a result of performing a sensory evaluation by the method described in Test Example 1, no problem was found in the flavor and taste of Negitro to which the product of the present invention was added. From the above results, the effectiveness of the flax seed extract of the present invention for preventing fading was confirmed.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI A61K 31/09 A61K 31/09 31/341 31/341 31/7028 31/7028 35/78 35/78 C A61P 39/06 A61P 39/06 (72) Inventor Hiroaki Tsuji 325-27-9-mori, Isogo-ku, Yokohama-shi, Kanagawa Prefecture (72) Inventor Shinichiro Miura 1-101 Nakamaru, Kanagawa-ku, Yokohama-shi, Kanagawa Prefecture (72) Inventor Tetsuo Unaii Tokyo 5-13-7 Nishikamata, Ota-ku, Tokyo (58) Field surveyed (Int.Cl. ⁷ , DB name) A61K 31/05 A23B 7/14 A23L 3/349 A23L 3/3544 A23L 3/3562 A61K 31/09 A61K 31/341 A61K 31/7028 A61K 35/78 A61P 39/06 CA (STN) EMBASE (STN) MEDLINE (STN)

Claims (13)

(57) [Claims] 1. An active oxygen species scavenger comprising a lignan compound represented by the following general formula (I) as an active ingredient. Embedded image (Wherein, R _{1 to} R ₄ are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and R ₅ and R ₆ are each independently selected from a hydroxyl group or a group consisting of glucose, galactose and fructose. The sugar chain residue in which one or two or more sugars are glycosidically bonded, or R ₅ and R ₆ together represent an oxygen atom.) 2. The active oxygen species scavenger according to claim 1, wherein the lignan compound is represented by the following general formula (II). Embedded image (Wherein R ₇ and R ₈ are the same or different and are each independently a hydroxyl group or 1 selected from the group consisting of glucose, galactose and fructose
The sugar chain residue in which one or two or more sugars are glycosidically linked, or R ₇ and R ₈ together represent an oxygen atom) 3. The lignan compound represented by the following structural formula (II-a):
The active oxygen species scavenger according to claim 1 or 2, which is at least one selected from compounds represented by (II-b), (II-c) and (II-d). Embedded image Embedded image Embedded image Embedded image (In the formula, Glc represents a glucose residue, and Gal represents a galactose residue.) 4. The lignan compound according to any one of claims 1 to 3, wherein the lignan compound is a component obtained by extracting a crushed product of linseed or a roasted product thereof or defatted lees with a lower alcohol or a hydrated lower alcohol. Reactive oxygen species scavenger. 5. A lignan compound which is obtained by extracting crushed or defatted lees of flaxseed or its roast with a lower alcohol or a hydrated lower alcohol, and subjecting the extract to acid hydrolysis.
The active oxygen species scavenger according to any one of claims 1 to 3, which is a component obtained by concentrating an extract of the hydrolyzate with a water-insoluble organic solvent. 6. The active oxygen species scavenger according to claim 1, wherein the reactive oxygen species is a superoxide and / or a hydroxyl radical. 7. An anti-fading agent comprising the lignan compound represented by the general formula (I) according to claim 1 as an active ingredient. 8. The anti-fading agent according to claim 7, comprising the lignan compound represented by the general formula (II) according to claim 2 as an active ingredient. 9. The structural formula according to claim 3, wherein the lignan compound is a lignan compound.
9. The anti-fading agent according to claim 7, which is at least one selected from compounds represented by (II-a), (II-b), (II-c) and (II-d). 10. The lignan compound according to any one of claims 7 to 9, wherein the lignan compound is a component obtained by extracting crushed or defatted flaxseed or roasted sesame seed with a lower alcohol or a hydrated lower alcohol. Anti-fading agent. 11. A lignan compound, which is obtained by extracting a crushed product or defatted cake of flaxseed or a roasted product thereof with a lower alcohol or a hydrated lower alcohol, and hydrolyzing the extract with an acid. The anti-fading agent according to any one of claims 7 to 9, which is a component obtained by concentrating the extract with a solvent. 12. The anti-fading agent according to any one of claims 7 to 9, wherein a crushed flaxseed or roasted product thereof or defatted lees is used as the lignan compound. 13. The anti-fading agent according to claim 7, further comprising L-ascorbic acid or a salt thereof.