JPH08208685A - Hydroxy free radical eliminating activator - Google Patents

Abstract

PURPOSE: To obtain a chemical usable in the field of food, medicine, cosmetic and agriculture, having hydroxy free radical eliminating activity with a very small amount, comprising a glycoside of a lignan such as sesaminol, P-1 or sesamolinol as an active ingredient. CONSTITUTION: A previously sterilized quarts sand is laid on a stainless steel bath, sesame seeds are scattered on the quartz sand, cultured in a constant temperature tank at 40 deg.C for two days while sufficiently spraying distilled water and germinated. A fixed amount of a germinated material in a germinated state of almost the same degree is ground together with hydrous methanol and the filtered filtrate is concentrated to dryness. The extract is washed with n-hexane and ethyl acetate, redissolved in hydrous methanol and purified by high performance liquid chromatography to give a glycoside of one or more lignans such as sesaminol, P-1 or sesamolinol including sesaminol diglycoside of formula II (Glc is glucose reside) and triglycoside. The glycoside is used as an active ingredient to give the objective hydroxyl free radical eliminating agent.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a hydroxy radical scavenging activator containing a lignan glycoside as an active ingredient. More specifically, it relates to a hydroxy radical scavenging activator containing as an active ingredient a lignan glycoside having a specific structure obtained from sesame seeds as a raw material. INDUSTRIAL APPLICABILITY The hydroxy radical scavenging activator of the present invention is widely used in the fields of pharmaceuticals, fields of agrochemicals, fields of cosmetics, etc., as well as foods.

[0002]

BACKGROUND ART Living organisms efficiently obtain energy necessary for survival by utilizing oxygen. However, in such energy metabolism, reactive oxygen species are generated as an intermediate in the process of converting oxygen into water. In general, as reactive oxygen species, superoxide anions released by stimulation of macrophages, hydroxy radicals produced by exposure to radiation, organic radicals produced in chain by peroxidation of lipids, etc. are known. These reactive oxygen species have high chemical reactivity and react with lipids, nucleic acids, proteins, etc., resulting in oxidative damage leading to various diseases. Excessive irradiation of radiation and ultraviolet rays, ingestion of chemical substances and tobacco, etc. are external factors for these. Among these, an important cause of biological damage caused by, for example, irradiation with radiation is a hydroxy radical produced from water molecules in the living body by irradiation with radiation.

This hydroxy radical is one of the most reactive oxygen species among reactive oxygen species, and it immediately undergoes a chemical reaction with lipids, proteins, nucleic acids, sugars, etc. existing in the living body to oxidize, modify or decompose them. And so on. This causes significant damage to genes, biological membranes, tissues, etc.
It is thought to cause various diseases such as carcinogenesis, arteriosclerosis, heart disease, inflammation or cell aging (Halliwell
B. and Gutteridge MC, Biochem. J., Volume 219,
1-14, 1984).

Therefore, a substance having a function of efficiently eliminating such toxic active oxygen species is useful as a protective agent against oxidative deterioration of components contained in the body or foods, pharmaceuticals, agricultural chemicals and the like. It is expected to be used practically in the field of foods, especially in the fields of health foods and nutritional foods, as well as in the fields of medicines / agrochemicals and cosmetics. Incidentally, known antioxidants such as tocopherol and ascorbic acid,
Speaking of hydroxy radical scavenging ability, vitamin E
Some of them have activity, but many are still unknown.

[0005] In recent years, as the toxicity of such reactive oxygen species, especially hydroxy radicals, to living organisms has been revealed, the usefulness of substances having an activity of efficiently scavenging them has been noted, and various substances are mainly natural. It is being investigated as a component derived from a product. Typical examples having hydroxy radical scavenging activity are mannitol, tryptophan,
Formic acid and the like are mentioned, and their hydroxy radical scavenging activity has been investigated (for example, Yoshihiko Oyanagi, "SOD and reactive oxygen species regulator-its pharmacological action and clinical application", No. 2).
24-228 pages, Japanese Medical Center, 1989).

[0006] However, there are still few substances having a hydroxy radical scavenging activity that are extremely minute and practically effective, and it is currently difficult to industrially obtain a large amount of these substances in a stable manner. Thus, despite the desire for stable supply of the active ingredient having the activity of eliminating hydroxy radicals, there have been few examples that have been industrially put into practical use.

By the way, sesame seeds are one of the natural products commonly used as a raw material for foods. Sesame seeds are a type of oil seed that has been used for food since ancient times, and its pharmacological effects have been handed down. Sesame is still cultivated all over the world, including in the tropics, and it is eaten because of its unique flavor of oils and seeds. That is, sesame is a plant material that can be stably obtained in a relatively large amount, and can be said to be a safe raw material for the human body. In addition, lignans are contained in sesame seeds as a characteristic compound, and various physiologically active functions including their antioxidant activity have been studied (for example, Mitsuo Namiki, Sadasaku Kobayashi, “Sesame Seeds”). Science ", Asakura Shoten, 1989).

In sesame seeds, lignans having an excellent antioxidant activity, namely sesaminol: tetrahydro-
1- [6-hydroxy-3,4- (methylenedioxy)
Phenyl] -4- [3,4- (methylenedioxy) phenyl] -1H, 3H-furo [3,4-C] furan, P-
1: Tetrahydro-1- (3-methoxy-4-hydroxyphenyl) -4- [3,4- (methylenedioxy) phenyl] -1H, 3H-furo [3,4-C] furan, sesamolinol: tetrahydro- 1- (3-methoxy-4
-Hydroxyphenoxy) -4- [3,4- (methylenedioxy) phenyl] -1H, 3H-furo [3,4-
C] Furan, pinoresinol: tetrahydro-1,4-
Di (3-methoxy-4-hydroxyphenyl) -1H,
Phenolic lignans such as 3H-furo [3,4-C] furan are included, and most of them are found to exist as saccharide compounds (lignan glycosides) in sesame seeds or defatted meal thereof. (Biosci. Biotech. Biochem.,
56, 2087-2088, 1992).

Further, it is known that a pinoresinol glycoside is obtained from a crushed product of sesame seeds, and that the glycoside has an antioxidant effect on the oxidation of lipid (Japanese Patent Laid-Open No. 6-162).
No. 82). However, this publication does not mention lignan glycosides other than pinoresinol glycosides. On the other hand, when sesame seeds are germinated, it is reported that phenolic antioxidant substances other than tocopherol and sesamol are produced in the germinated products (Journal of Japan Food Industry Society, Vol. 32, 407-). 412, 1985
Year). It is also known to extract antioxidants or antioxidants using cultured cells derived from adult sesame seeds (Agricultural Chemical Society of Japan 1991 Annual Meeting, 236, 1991). , Tokuhei 4-214
75, JP-A-5-124949). However, the substances disclosed therein are different from the above-mentioned phenolic lignans.

[0010]

Therefore, the present invention is
It is an object of the present invention to provide a novel hydroxy radical scavenging activator, particularly a hydroxy radical scavenging activator that utilizes components in sesame seeds.

[0011]

Means for Solving the Problems As a result of intensive studies to achieve the above-mentioned object, the present inventors have found that a specific lignan glycoside has an activity capable of effectively eliminating hydroxy radicals, and The invention was completed.

That is, the gist of the present invention is sesaminol,
1 selected from the group consisting of P-1 and sesamolinol
Glycoside of seed lignan (hereinafter referred to as lignan glycoside)
Is a hydroxy radical scavenging activator containing as an active ingredient.

The lignan glycoside according to the present invention comprises one lignan moiety selected from the group consisting of sesaminol, P-1 and sesamolinol represented by the above chemical name, and glucose, galactose or fructose at its hydroxyl group. It is composed of a sugar moiety in which 1 to 3 sugar residues are linked. The lignan glycoside targeted by the present invention is preferably a water-soluble glucosidolignan whose sugar residue is a diglucoside residue and / or a triglucoside residue, and more preferably at least the following structural formula (I
-A) containing sesaminol diglucoside and / or sesaminol triglucoside represented by structural formula (Ib).

[0014]

Embedded image (In formula (Ia), Glc represents a glucose residue.)

[0015]

[Chemical 4] (In formula (Ib), Glc represents a glucose residue.)

The lignan glycoside according to the present invention can be produced by a chemical synthesis method, using sesame seeds or a crushed product thereof or a defatted meal thereof as a raw material,
Alternatively, the inventors of the present application filed a prior patent application (Japanese Patent Application No.
No. 16079), for example, it is convenient to prepare a germinated product of sesame seeds by the method described below. The extract component obtained by such a method and the purified product thereof can be used as a hydroxy radical scavenging activator.

First, as long as sesame seeds have not been subjected to high temperature treatment such as culturing, they are types such as white sesame, black sesame, etc., domestic, Chinese, Indian, African, etc., for cultivation or for oil extraction. It can be used regardless of. This is uniformly dispersed in a suitable medium that can contain water or water, for example, agar, quartz sand, sea sand, absorbent cotton, sand, soil or the like, preferably a sterilized medium, at 10 to 50 ° C., preferably 30 to 40. Culturing is performed at 5 ° C. for 5 to 100 hours, preferably 24 to 72 hours, while supplementing water with time. The culture may be performed under illumination or under dark conditions. By such a treatment, a large amount of the lignan glycoside according to the present invention can be produced and accumulated in a humidified product or a germinated product of sesame seeds.

After separating the sesame seeds swollen or germinated with water from the medium, the sesame seeds are put into a grinder such as a food mixer, a blender or a homogenizer and pulverized. The obtained pulverized product is n
-A defatted lees obtained by extracting and removing oil with a fat-soluble organic solvent such as hexane may be used. Next, the lower alcohol capable of extracting the lignan glycoside or its hydrous substance is 1 to 10 times (v / wt) (where v: volume, wt: weight) with respect to the pulverized product or its defatted meal. The same shall apply hereinafter)
If necessary, pulverization and extraction operations are repeated to remove solids by a conventional method such as decantation, centrifugation, filtration, etc., and then water and alcohol are removed by heating or non-heating at normal pressure or reduced pressure, and water content is included. A lower alcohol extract is obtained. The extract contains the lignan glycoside,
In addition, it is a mixture containing various sugar chain compounds.

Here, as the hydrous lower alcohol,
A straight-chain or side-chain lower alcohol having 1 to 4 carbon atoms,
For example, methanol, ethanol, n-propanol, isopropanol, n-butanol and the like are mixed with water to give an alcohol concentration of 30 to 100% (v / v), preferably 5
0 to 100% (v / v), more preferably 50 to 80%
(V / v), most preferably 70-80% (v / v). If the alcohol concentration is less than 30% (v / v), a large amount of the water-soluble polysaccharide containing no lignan glycoside according to the present invention is extracted, which is not preferable.

In order to remove impurities other than the lignan glycoside according to the present invention (fat-soluble substances and water-soluble substances compared to the lignan glycoside according to the present invention) in the hydrous lower alcohol extract. It is desirable to perform the following processing. That is, first, to remove fat-soluble impurities,
2 to 10 times (v / w) for hydrous lower alcohol extract
The water-insoluble organic solvent of t) such as ethyl acetate or n-hexane and water are added for extraction, and the mixture is separated into two phases by centrifugation or the like. The organic solvent phase is removed and the aqueous phase is concentrated to dryness. At this time, the target lignan glycoside is concentrated on the aqueous phase side.

Next, in order to remove water-soluble impurities, a small amount, preferably 1 to 5 times (v / wt) of hydrous alcohol (alcohol concentration 30 to 100% (v / wt) is added to this extract.
v)), and this is added dropwise to a relatively large amount, preferably 10 to 200 times (v / wt) of alcohol that is gently stirred. After standing, the precipitate is removed by centrifugation or fractional filtration, and the mixture is concentrated to dryness to obtain a crude lignan glycoside. If necessary, these operations are repeated. The alcohol used for such treatment may be the same as the lower alcohols used when extracting the crushed sesame seeds.

The crude lignan glycosides thus obtained are those in which saccharides such as glucose and galactose are bound to hydroxyl groups of lignans such as P-1, sesamolinol and pinoresinol, in addition to the main component of sesaminol. It is a mixture of di- and / or triglucoside lignans having 2-3 molecules of glucose bonded as a main component. This is a water-soluble substance that is soluble in n-butanol, ethanol, methanol, water and the like.

The hydrous lower alcohol extract and the crude lignan glycoside are fractionated into individual lignan glycoside components by using an adsorbent such as silica gel or octadecyl silica (ODS), if necessary. It can be purified. That is, for example, a column packed with ODS is prepared, equilibrated with water, and then the hydrous lower alcohol extract or crude lignan glycoside is added at a loading rate of 0.1 to 5%.
(Wt / v) and hydrous alcoholic solvent (methanol, ethanol, n-propanol, isopropanol, n-butanol, etc. as alcohol) is used to elute a predetermined fraction by a stepwise elution method in which the alcohol concentration is sequentially increased. . The elution fraction obtained here may be further subjected to high performance liquid chromatography (HPLC) using the adsorbent, preparative liquid chromatography or the like to purify each component to a higher purity, if necessary. it can.

The structure of the lignan glycoside is such that each component purified to a single substance with high purity is acid-hydrolyzed to be divided into a lignan (aglycone part) and a sugar part, which are respectively trimethylsilylated and subjected to gas chromatography. Offering,
Alternatively, it can be confirmed by analysis by nuclear magnetic resonance spectroscopy or mass spectroscopy.

Next, a method for measuring the scavenging activity of active oxygen species will be described below. Hydroxy radical scavenging activity is performed by an electron spin resonance (ESR) device using a spin trap method (eg, Gow-Chin Yen Yen) using 5,5′-dimethyl-1-pyrroline-N-oxide (hereinafter abbreviated as DMPO).
and Pin-Der Cuh, J. Agric. Food Chem., Volume 42,
Pp. 629-632, 1994). That is, in the presence of a ferrous sulfate solution, hydrogen peroxide produces a hydroxy radical and a hydroxy anion by the Fenton reaction. Of these, hydroxy radicals are supplemented by the coexisting DMPO to obtain a DMPO-OH adduct. This adduct is relatively stable and exhibits the characteristic quartet in the ESR spectrum. At this time, when a substance having an activity of eliminating hydroxy radicals coexists in the reaction solution, the ESR spectrum of the DMPO-OH adduct decreases. The hydroxy radical scavenging activity of the sample can be measured from the amount of decrease in the integrated value of this spectrum.

As substances having an activity of eliminating hydroxy radicals, mannitol, tryptophan, formic acid and the like are mentioned in the above-mentioned document ("SOD and reactive oxygen species regulator-its pharmacological action and clinical application"). The activity is being investigated, and the activity is 1 in mannitol.
It was measured at each abundance of 0 μmol / mL, 20 μmol / mL for tryptophan and 100 μmol / mL for formic acid. On the other hand, the test amount of the lignan glycoside according to the present invention is measured at 1 μmol / mL or less, and sufficient hydroxy radical scavenging activity is recognized even at such a minute concentration. Therefore, the lignan glycoside according to the present invention has extremely high activity as an active ingredient of a hydroxy radical scavenging activator.

The hydroxy radical scavenging activator of the present invention is a glycoside of one lignan selected from the group consisting of sesaminol, P-1 and sesamolinol, especially diglucosidolignans and / or triglucosidolignans, especially the above structures. Use as an active ingredient any of the lignan glycosides containing at least one of the sesaminol diglucoside represented by the formula (Ia) and the sesaminol triglucoside represented by the structural formula (Ib). You can These may be chemically synthesized, but they are obtained by removing impurities (fat-soluble substances and water-soluble substances) from the hydrous lower alcohol extract obtained from the humidified or germinated sesame seeds described above. It is desirable to use crude lignan glycosides and high-purity lignan glycosides obtained by fractionating these with column chromatography or HPLC.

[0028]

EXAMPLES The present invention will be specifically described below with reference to Examples and Reference Examples. Reference Example 1 Pre-sterilized quartz sand is spread on a 300 cm ² stainless steel vat, 10 g of Chinese sesame seeds are sprinkled on the vat, and it is cultured for 2 days in a constant temperature bath at 40 ° C. while sufficiently spraying distilled water. , Sprouted. The germination rate was 89%. A certain amount of germinated material having a similar germination state was pulverized with 100 mL of water-containing methanol (80% (v / v)) using a blender.
The residue was filtered and the filtrate was concentrated to dryness to obtain a hydrous methanol extract. Then, the extract was washed twice with n-hexane and ethyl acetate to obtain a crude lignan glycoside. This crude lignan glycoside was added to 100 mL of hydrous methanol (80%
(V / v)), and subjected to high performance liquid chromatography (HPLC) to analyze the composition.

The HPLC conditions were as follows: a pump (CCPM, manufactured by Tosoh Corporation) and a column (Soken Pak ODS-W 5μ, 10 mm).
φ × 250 mm), UV absorption detector (UV-8000,
(Manufactured by Tosoh Corporation) is connected, and elution is performed with water: methanol 9
60 minutes after starting from 0:10 (v: v), 10: 9
Use a linear gradient of 0 (v: v) and set the flow rate to 1
mL / min, the detection wavelength was 288 nm.

As a result of HPLC analysis, in the crude lignan glycoside, sesaminol diglucoside and sesaminol triglucoside were the main components, and sesaminol monoglucoside, sesaminol monogalactoside, P-1 diglucoside, sesaminolinol monoglucoside were used. , Sesamolinol diglucoside, pinoresinol diglucoside and pinoresinol triglucoside components are contained, and sesaminol triglucoside is 35% of these components,
Sesaminol diglucoside accounted for 45%.

Each component of the lignan glycoside was isolated and analyzed by the method described below. That is, 1 g of crude lignan glycoside was subjected to reverse phase partition column chromatography (YMC-GEL ODS-A 60 200/6.
0 (manufactured by Yamamura Chemical Co., Ltd.) 60 g was suspended in 20% (v / v) water-containing methanol and packed in a glassy column), and the methanol concentration was changed from 80:20 (v: v) of water: methanol to 500 ml every 500 ml. 40:60 in steps of% (v / v)
Using hydrous methanol up to (v: v), flow rate:
Elution was performed at 0.8 mL / min. Of the eluted fractions containing 100 mL of water-containing methanol, the fractions containing the components corresponding to the components detected by the HPLC analysis were concentrated to dryness to obtain a lignan glycoside fraction. Further, each of the fractions was repeatedly subjected to preparative HPLC and purified until each lignan glycoside component became single.

The purified product of each lignan glycoside fraction was
Hydrolyze with hydrochloric acid for 30 minutes at 100 ℃,
It was extracted with ethyl acetate. The ethyl acetate layer obtained here was used as a lignan (aglycone part) analysis sample, and the aqueous layer was used as a sugar part analysis sample. The ethyl acetate layer was concentrated to dryness at 40 ° C. or lower, and then TMS-PZ (manufactured by Tokyo Chemical Industry Co., Ltd.) was added to form trimethylsilyl, which was subjected to gas chromatography (GLC) for quantitative analysis (external standard: sesamin).

The GLC conditions are as follows. GLC device: Hewlett-Packard 5890, column: DB-1
7HT (15m x 0.319mm, film thickness: 0.
15 μm, manufactured by J & W SCIENTIFIC), injection method: split method (split ratio 1/10), column temperature: 270 ° C., carrier gas: He.

The aqueous layer was used as a pretreatment filter for HPLC (pore size: 0.2 μm, Mysholydisc W-13-).
(2, manufactured by Tosoh Corporation), 5 ml of acetone was added to the filtrate, and the mixture was concentrated to dryness under reduced pressure, and then TMS-PZ (manufactured by Tokyo Chemical Industry Co., Ltd.) was added for trimethylsilylation, which was subjected to GLC for quantitative analysis. (External standard: glucose, galactose, fructose).

The GLC condition is column: DB-1701.
(15m x 0.25mm, film thickness: 1.0μm,
J & W SCIENTIFIC), injection method: split method (split ratio 1/50), column temperature: 180
The same as in the case of the lignan (aglycone part) analysis except that the temperature is set to ° C.

Example 1 The scavenging activity of lignan glycoside components against hydroxy radicals was measured. That is, electron spin resonance (ESR)
The hydroxy radical scavenging activity was measured by a spin trap method using DMPO using an apparatus. 75 μL of 0.1 mM ferrous sulfate solution containing 0.55 mM diethylenetriamine N, N, N ′, N ″, N ″ pentaacetic acid, 75 μL of 1 mM hydrogen peroxide solution, 20 μL of 8.8 mM DMPO solution and the following lignan glycoside A reaction solution was prepared by mixing 50 μL of the aqueous solution. The purified product obtained in Reference Example 1 (for example, sesaminol triglucoside) has a concentration of 0 to 1.0 μmol / mL in the reaction solution.
Of the DMPO-OH adduct was measured by an ESR apparatus. The ESR measurement conditions are the ESR device (JES-RE manufactured by JEOL Ltd.).
1X), magnetic field: 334.5 ± 5 mT, output: 8 mV,
Modulation: 100kHz, measured at room temperature, response time: 0.1s
And manganese ion (Mn ²⁺ ) in magnesium oxide
Was used as the standard substance. The ESR spectra of the scavenging activity of hydroxy radicals by sesaminol triglucoside are shown in FIGS. 1 (A) to 1 (D). Compared with the ESR spectrum in which sesaminol triglucoside was not added (FIG. 1 (A)), the spectrum clearly decreased as the concentration of sesaminol triglucoside added increased (FIG. 1 (B), FIG. 1).
(C) and FIG. 1 (D)). From this, it became clear that sesaminol triglucoside has an activity of eliminating hydroxy radicals.

Example 2 In the method described in Example 1, the types of lignan glycoside components added to the reaction solution for measuring hydroxy radicals (purification of each of the sesaminol diglucoside and the sesamolinol diglycoside obtained in Reference Example 1) Substance) and the concentration, ESR spectra were measured, and the relationship between the integrated value and the added concentration was determined for each glycoside component. As a result, as shown in FIG. 2, sesaminol diglucoside, sesamolinol diglucoside and sesaminol triglucoside (Example 1).
Each of the lignan glycoside components of
A strong activity of scavenging hydroxy radicals was observed at an addition amount in the concentration range of ˜1.0 μmol / mL.

Example 3 Hydroxyl radical scavenging activity was measured by the same method as in Example 1, using the hydrous methanol extract, crude lignan glycoside and column fraction obtained in Reference Example 1 as samples. As a result, the addition concentration of each sample showing the activity of eliminating 50% of the strength of hydroxy radicals in the case of no addition was: 3
0 μmol / mL ,: 2 μmol / mL and: 0.08 μ
It was mol / mL. From this, it was revealed that the lignan glycoside according to the present invention has a sufficient hydroxy radical scavenging ability not only in the purified product of each component but also in the mixture.

[0039]

According to the present invention, sesaminol, P-1
Alternatively, it is possible to provide a hydroxy radical scavenging activator containing a lignan glycoside selected from sesamolinol as an active ingredient. The lignan glycoside is easily obtained from a germinated sesame seed. Further, the hydroxy radical scavenging activator of the present invention has a strong trace amount of hydroxy radical scavenging ability, and is expected to be applicable to products in the fields of food, cosmetics, pharmaceuticals, agricultural chemicals and the like.

[Brief description of drawings]

FIG. 1 is an electron spin resonance spectrum of a 5,5′-dimethyl-1-pyrroline-N-oxide-OH adduct, showing changes in hydroxy radical scavenging activity depending on the amount of lignan glycoside component (sesaminol triglucoside) added. FIG. The addition concentration of sesaminol triglucoside is as shown in FIG. 1 (A): no addition, FIG. 1 (B): 0.05 μmol.
/ ML, FIG. 1 (C): 0.10 μmol / mL, FIG. 1 (D):
It is 0.25 μmol / mL. Mn ²⁺ indicates a manganese ion (standard substance) in magnesium oxide.

FIG. 2: Integrated value of electron spin resonance spectrum intensity of 5,5′-dimethyl-1-pyrroline-N-oxide-OH adduct and lignan glycoside component (sesaminol diglucoside, sesamolinol diglucoside and sesaminol). It is a figure which shows the relationship with the addition concentration of (triglucoside).

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display area A61K 35/78 ADU // C07G 3/00

Claims (4)

[Claims] 1. A hydroxy radical scavenging activator containing as an active ingredient a glycoside of lignan selected from the group consisting of sesaminol, P-1 and sesamolinol (hereinafter referred to as lignan glycoside). 2. The hydroxy radical scavenging activator according to claim 1, wherein the lignan glycoside is a water-soluble glucosidolignan having a diglucoside residue and / or a triglucoside residue as a sugar residue. 3. A lignan glycoside having at least sesaminol diglucoside represented by the following structural formula (Ia) and / or sesaminol triglucoside represented by the following structural formula (Ib): (In the formula (Ia), Glc represents a glucose residue.) (In formula (Ib), Glc represents a glucose residue.)
The hydroxyl radical scavenging activator according to claim 1 or 2, which comprises: 4. The lignan glycoside is a component obtained by extracting a humified product of sesame seeds, a crushed product of germinating seeds, or a defatted meal thereof with a lower alcohol containing water. Hydroxyl radical scavenging activator.