JPH11323326A - Active oxygen eliminating agent, skin protecting agent and discoloration inhibitor - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a highly safe active oxygen eliminating agent, skin protecting agent and discoloration inhibitor. SOLUTION: An active oxygen eliminating agent, skin protecting agent or discoloration inhibitor contains at least one chosen from pedunculagin and tellimagrandin I isolated from trees belonging to the genus Eucalyptus as an effective component. A skin protecting agent or discoloration inhibitor may contain a water-soluble extract of trees belonging to the genus Eucalyptus as an effective component.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an active oxygen scavenger, a skin preservative and a discoloration inhibitor suitable for use in foods and drinks, pharmaceuticals, cosmetics and the like, and more particularly to an active oxygen scavenger for scavenging active oxygen. The present invention relates to a skin preservative agent effective for maintaining skin health and a discoloration preventing agent effective for preventing discoloration of foods and the like.

[0002]

2. Description of the Related Art In recent years, with increasing awareness of health, Oriental medicine utilizing natural healing power has attracted attention. Also food,
As interest in the safety of cosmetics, pharmaceuticals, and the like has increased, a return to safer natural materials has been recognized. In particular, foods and cosmetics closely related to daily life are pursuing a natural orientation. In addition, for active oxygen, which is a cause of various chronic diseases, a natural material is required as a scavenger.

[0003] The active oxygen, in particular superoxide anion (O ₂ ^-) usually occur in vivo, but is erased by various enzymes and antioxidants, including superoxide dismutase (SOD), Aging It is considered that the active oxygen-scavenging substance decreases along with the above, and the living body becomes more susceptible to attack by active oxygen. Therefore, it has been conventionally recommended to take active oxygen scavengers in the form of food or medicine. In addition, it has been pointed out that active oxygen is greatly involved in discoloration, fading, and photodegradation of foods and the like. Among such active oxygen scavengers, SOD-like active materials such as gallic acid, flavonoids, catechins, ascorbic acid and chlorogenic acid have been known as those obtained from natural materials.

[0004] On the other hand, it is well known that tyrosinase is greatly involved in the production of melanin pigments which cause stains and freckles. In addition, tyrosinase inhibitors for preventing the production of melanin pigment have been developed. It has been pointed out that the tyrosinase is also involved in discoloration of foods and the like. Among the tyrosinase inhibitors, arbutin is well known as one obtained from a natural material. The tyrosinase inhibitor is usually used by being blended into a whitening cosmetic or an external preparation.

[0005]

The above compounds are obtained from natural materials and are therefore highly safe. However, they have insufficient active oxygen scavenging activity, tyrosinase inhibitory activity or discoloration preventing activity. Therefore, a more active natural material has conventionally been required. Therefore, an object of the present invention is to provide an active oxygen scavenger, a skin preservative, and a discoloration inhibitor which are excellent in active oxygen scavenging activity, tyrosinase inhibitory activity, discoloration prevention activity, etc. and have high safety and can be obtained from natural materials. It is to be.

[0006]

Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have made intensive studies, and as a result, the genus Eucalyptus (Eu)
The water-soluble extract obtained by extracting water, a hydrophilic organic solvent or a mixed solvent thereof from a tree, especially leaves of the genus calyptus) is said to be excellent in the above-mentioned active oxygen elimination activity, tyrosinase inhibitory activity and discoloration prevention activity. Find the facts,
After further studies, they found a new fact that pedunculagin or tellimagrandin I isolated from the eucalyptus extract greatly contributed to the expression of each of the above activities, and found the present invention. It was completed.

That is, the active oxygen scavenger, skin preservative (tyrosinase inhibitor) and discoloration inhibitor of the present invention are all the above-mentioned pedunclazine and terimagrandin I.
Characterized by containing at least one selected from the group consisting of: The above pedunclazine and terimagrandin I are compounds belonging to tannins, especially hydrolyzable ellagitannins. These compounds have been known for use as antiretroviral agents (JP-A-4-264026). Further, when viewed broadly as a group of tannin compounds, Nf-kB activation inhibitors useful as antiviral agents and immunosuppressants (JP-A-9-591)
No. 51), anti-hepatitis B virus agent (anti-HBV agent)
(Japanese Patent Application Laid-Open No. 4-36239),
A report that it is useful for prevention and treatment of periodontal disease by focusing on its strong hemostatic effect (Japanese Patent Application Laid-Open No. 58-38208) and a report that it is useful for treatment and prevention of skin inflammation (Japanese Patent Application Laid-Open No. 58-38208) 58-38209).

[0008] However, it is not known that the above-mentioned pedunclazine and terimagrandin I in the present invention have excellent active oxygen scavenging activity, tyrosinase inhibitory activity and discoloration preventing activity. In addition, the water-soluble extract extracted from the eucalyptus tree itself has excellent tyrosinase inhibitory activity and discoloration preventing activity.

Accordingly, the present invention also provides a skin preservative and a discoloration inhibitor characterized by containing a water-soluble extract extracted from a eucalyptus tree as an active ingredient. As described above, the above pedunkradin and terimagrandin I can be isolated from an extract of a tree of the genus Eucalyptus, but are isolated not only from the genus Eucalyptus but also from other plants. Or it may be chemically synthesized.

[0010]

BEST MODE FOR CARRYING OUT THE INVENTION The above pedunkradin has the formula (1):

Embedded image It is represented by The above Terima Grandin I is represented by the formula (2):

Embedded image It is represented by

In each formula, the 1-position of the glucose moiety exists as an equilibrium mixture (anomer) of α- and β-forms of glucose because the hydroxyl group is not acylated.
Therefore, in each of the above formulas, the bond of the hydroxyl group at the 1-position of the glucose moiety is represented by a wavy line to indicate that it is an anomer. As is clear from these formulas, pedunclazine represented by the above formula (1) and terimaglandin I represented by the formula (2) are substituted with hexahydroxydiphenoyl at the 2- and 3-position hydroxyl groups of the glucose moiety. Group or galloyl group has an ester bond.

As described above, pedunkradin and terimagrandin I can be obtained from a tree of the genus Eucalyptus, particularly a leaf of eucalyptus, as a raw material, through an extraction treatment, and a separation and purification treatment. Eucalyptus is a plant belonging to the family Myrtaceae and contains eucalyptus oil whose main component is cineole. Eucalyptus which can be used as a raw material in the present invention is not particularly limited. For example, E. glo
bulus, E. rostrata, E. robsta and the like.

The extraction process from eucalyptus is performed as follows. First, crush the raw plant, preferably the leaves,
The active ingredient is extracted using water, a hydrophilic organic solvent or a mixture thereof. As the hydrophilic organic solvent, for example, lower alcohols such as methanol, ethanol and propanol, acetone and the like can be used. As the extraction method,
There is no particular limitation, and room temperature homogenization extraction, reflux extraction and the like can be used. After extraction, the extract obtained is saturated with water.
Further extraction may be carried out with butanol, ethyl acetate or the like, and the obtained extract may be subjected to an extraction treatment with water-containing ethanol or the like. After the extraction, the active ingredient is isolated using adsorption chromatography, partition chromatography, ion exchange chromatography or the like, and further purified according to a conventional method.

However, since pedunclazine and terimagrandin I in the present invention are obtained by the extraction treatment from eucalyptus as described above, there is no problem in safety even if purification is insufficient, but rather unpurified. Even in such cases, a synergistic effect (crude drug effect) with other undetected components can be expected. The active oxygen scavenger of the present invention can be used in addition to ordinary foods and drinks, and can also be used as pharmaceuticals by utilizing its high active oxygen scavenging activity. As a medicament, a solid, semi-solid or liquid form can be used by adding a usual pharmaceutically acceptable carrier thereto.
Specifically, for example, oral administration preparations such as tablets, capsules, pills, granules, powders, emulsions, suspensions, syrups, and pellets, and parenteral administration preparations such as injection solutions, drip solutions, and suppositories Is raised. Furthermore, the active oxygen scavenger of the present invention can also be incorporated into external preparations and cosmetics as described below for the purpose of preventing skin aging and the like.

In the preparation of pharmaceutical preparations, conventionally used auxiliaries such as surfactants, excipients, coloring agents, preservatives, stabilizers, buffers and suspending agents can be used. The dose is usually 0.01 to 100 mg / kg body weight per day as pedunkradin or terimagrandin I,
Preferably, it is 0.5 to 50 mg / kg body weight.

Next, the skin preservative of the present invention will be described. The skin preservative of the present invention contains pedunclazine or terimaglandin I isolated from eucalyptus as an active ingredient as described above, or contains a water-soluble extract of eucalyptus as an active ingredient. When the extract is used, a treatment such as deodorization (excluding cineol odor) and decolorization may be performed within a range that does not affect the activity. Also,
As appropriate, a fractionation treatment or a separation / purification treatment by various types of chromatography or the like may be performed to obtain a more active skin preservative. Since the skin preservative of the present invention functions as an inhibitor of tyrosinase activity involved in the production of melanin pigment on the skin surface, it has a whitening effect. In addition, the water-soluble extract of pedunclazine, terimagrandin I or eucalyptus according to the present invention has high hyaluronidase inhibitory activity in addition to tyrosinase inhibitory activity. Hyaluronidase is a hyaluronic acid hydrolase that is widely distributed in connective tissues such as the surface layer of the dermis in a living body and has a function of keeping the skin moisturized and water-retained, lubricating, and flexible.
Hyaluronic acid is also said to be involved in anti-inflammatory and anti-allergic effects on the skin. Therefore, the skin preservative agent of the present invention, which also has a hyaluronidase inhibitory activity, has an effect of enhancing skin moisturization / water retention, lubricity, and flexibility, in addition to the above-described whitening effect. It is beneficial. Therefore, the skin preservative agent of the present invention is used not only in the form of cosmetics but also as an external preparation, and may be orally administered in the form of tablets, injections and the like, if necessary.

The cosmetics include, for example, lotions, emulsions, lotions, tonics, cosmetic creams, sprays, lipsticks, foundations, shampoos, rinses, bath salts and the like. These cosmetics are produced by mixing the active ingredient or the extract from eucalyptus with a commonly used cosmetic base. External preparations include, for example, ointments, creams, solutions, patches and the like, and can be produced in combination with carriers conventionally used in pharmaceuticals. The content of the active ingredient in these cosmetics and external preparations is 0.1% as pedunkradin or terimagrandin I.
It is good to be 100 mg / g, preferably 1-10 mg / g.

When an extract is used, its content should be 0.1.
It is good to be 5 to 100 mg / g, preferably 1 to 10 mg / g. Next, the anti-tarnish agent of the present invention will be described. In the discoloration inhibitor of the present invention, peduncladin or terimaglandin I extracted from eucalyptus in the same manner as described above may be used as an active ingredient, or an extract of eucalyptus may be used as an active ingredient. When the extract is used, a treatment such as deodorization (excluding cineol odor) and decolorization may be performed within a range that does not affect the activity. Also,
As appropriate, a fractionation treatment, a separation / purification treatment by various types of chromatography and the like may be performed to obtain a more active discoloration inhibitor.

It is believed that active oxygen and tyrosinase are involved as one of the causes of discoloration of foods and the like. Therefore, the discoloration inhibitor of the present invention containing the above-mentioned pedunclazine or terimagrandin I as an active ingredient is not suitable for the above-mentioned discoloration inhibitor. It is presumed to be based on the same function as active oxygen scavenger and skin preservative. The discoloration inhibitor of the present invention is added to food in a solid, semi-solid or liquid form. Solids include powders, granules, pellets, tablets and the like, semi-solids include jellies and syrups, and liquids include emulsions and suspensions. The amount of the discoloration inhibitor of the present invention, as pedunclazine or terimagrandin I, is preferably 0.01 to 50 mg, preferably 0.1 to 10 mg, per 1 g of food. In the case of an extract, the extract is preferably added in an amount of 0.05 to 50 mg, preferably 0.1 to 10 mg, per 1 g of food.

The discoloration inhibitor of the present invention can be added to foods such as processed meat products, processed fish meat, beverages, etc.
Discoloration, fading, light deterioration and the like can be prevented.

[0021]

EXAMPLES Hereinafter, the active oxygen scavenger, skin preservative and discoloration inhibitor of the present invention will be described in detail with reference to Reference Examples, Examples and Test Examples. Reference Example 1 500 g of dried leaves of eucalyptus were refluxed with 3 kg of 40% ethanol for 2 hours, cooled at room temperature, filtered, and the filtrate was refrigerated overnight. Then, the filtrate was further filtered, and the obtained filtrate was used as a eucalyptus extract.

This extract was concentrated under reduced pressure to 300 ml,
Then, the concentrated solution was subjected to ether, ethyl acetate, water saturation n
-Extraction was carried out sequentially with butanol and water. Each obtained extract was concentrated under reduced pressure and freeze-dried to obtain a dry extract. The eucalyptus extract and each dried extract were examined for active oxygen scavenging activity and tyrosinase inhibitory activity. The measuring method is as follows.

(1) Method of measuring active oxygen scavenging activity 20 ml of 0.1 M phosphate buffer (pH 7.5), 5 mM
Diethylenetriaminepentaacetic acid (DETAPAC) 30m
1, 0.75 mM nitro blue tetrazolium (NB
T) 0.2 ml of an aqueous solution of a sample substance adjusted to a predetermined concentration was added to 0.9 ml of a mixed solution composed of 10 ml and 30 ml of 0.3 mM xanthine, mixed well, and stirred at 25 ° C. for 10 minutes. The reaction was started by adding 0.1 ml of 0.08 U / ml xanthine oxidase (XOD) thereto. After the start of the reaction, 25 ° C, 560 nm
Was continuously recorded for about 2 minutes, and the change in absorbance for 1 minute was determined from the linear portion (Oberley, LW and
Spitz, DR, "Methods in Enzymology", 105, 457 (1
984), an improved method of Oberley et al.). On the other hand, separately from this, the uric acid production rate was determined by measuring the absorbance at 295 nm, and the value obtained by correcting the change in absorbance with this value was defined as the active oxygen elimination rate. The activity was measured by changing the concentration of the sample substance stepwise, and the concentration at which the erasure rate was 50% was defined as the 50% effective concentration (EC ₅₀ ). The smaller this value is, the stronger the activity is.

(2) Method for measuring tyrosinase inhibitory activity 0.4 ml of 1/15 M phosphate buffer (pH 6.8),
0.1 ml of a 0.05% L-dopa solution and 0.4 ml of an aqueous solution of a sample substance adjusted to a predetermined concentration are mixed, and then mixed at 25 ° C.
For 5 minutes. 0.1 ml of 300 U / ml tyrosinase was added thereto to start the reaction. 1 from the start of the reaction
The absorbance after minutes and 6 minutes was measured at 475 nm and 25 ° C. Then, the difference in absorbance (A ₁ ) for the difference of 5 minutes was determined. In addition, the absorbance change value (A ₀ ) was obtained in the same manner even when the sample substance was not added, and the tyrosinase inhibition rate was calculated from the following equation. Tyrosinase inhibition rate (%) = [(A ₀ −A ₁ ) /
A ₀ ] × 100 The above activity was measured by gradually changing the concentration of the sample substance,
The concentration at which the inhibition rate shows 50% is the 50% inhibition concentration (IC ₅₀ )
And The smaller this value is, the stronger the activity is.

Table 1 shows the measurement results.

[Table 1]

From Table 1, it is found that the extract of n-butanol has the highest activity, and the eucalyptus extract also has high activity. Reference Example 2 About the extract of n-butanol obtained in Reference Example 1, Diaion HP-20 (diameter 3.3 cm, length 2
Column chromatography was performed using 0 cm (manufactured by Mitsubishi Chemical Corporation), and elution was performed in order of water, 20% ethanol, 40% ethanol, 60% ethanol, and ethanol in order of 1 liter each. The obtained extract was concentrated under reduced pressure and freeze-dried to obtain a dry extract. The active oxygen scavenging activity and the tyrosinase inhibitory activity of each extract were examined in the same manner as in Reference Example 1. Table 2 shows the results.

[0027]

[Table 2] As shown in Table 2, the active oxygen scavenging activity and the tyrosinase inhibitory activity were strong in the 20% ethanol eluted part and the 40% ethanol eluted part.

Example 1 In Reference Examples 1 and 2, the above-mentioned Diaion and Toyopearl HW were extracted from the 20% and 40% ethanol extracts obtained by column chromatography of the ethyl acetate extract and the n-butanol extract.
-40 (fine grade product, diameter 2.2cm, length 20c)
m, eluted with 50% ethanol, manufactured by Tosoh Corporation) and MC
I-gel CHP-20P (diameter 1.1 cm, length 20
The column chromatography was repeated in the order of cm, water, 10% ethanol, 20% ethanol and 30% ethanol, manufactured by Mitsubishi Chemical Corporation, and several types of active substances could be isolated.

As a result of identification tests such as NMR, gallic acid (isolated yield 90 mg) and ellagic acid (isolated yield 86 m
g), pedunclazine (isolated yield 30 mg) and terimagrandin I (isolated yield 261 mg). The results of an identification test of pedunkradin and terimagrandin I by NMR are shown below.

(I) ¹ H-NMR (600 MHz, acetone-d ₆ + D ₂ O, J in Hz) of pedunclazine: α-form β-form glucose H-1 δ5.42 (d, J = 4.2) 5.02 (d , J = 8) [1H in total] H-2 5.04 (dd, J = 4.2, 10) 4.83 (dd, J = 8.96) [1H in total] H-3 5.44 (t, J = 10) 5.21 (dd , J = 9.6, 10.2) [1H in total] H-4 5.05 (t, J = 10) 5.04 (t, J = 10.2) [1H in total] H-5 4.58 (ddd, J = 1.2, 4.18 (ddd , J = 1.8, 7.2, 10.2) 6.6, 10) [1H in total] H-6 3.82 (dd, J = 1.2, 3.76 (dd, J = 1.8, 13.2) [1H in total] 13.2) 5.23 (dd, J = 6.6, 5.26 (dd, J = 7.2, 12.6) [1H in total] 12.6) Hexahydroxydiphenoyl (HHDP) -H 6.66, 6.65 (1H in total) 6.60 (1H) 6.56, 6.51 (1H in total ) 6.33 (1H)

(II) ¹ H-NMR (600 MHz, acetone-d ₆ + D ₂ O, J in Hz) of terimagrandin I: α-form β-form glucose H-1 δ5.552 (d, J = 4.2) 5.07 (d, J = 8) [1H in total] H-2 5.10 (dd, J = 4.2, 10) 5.25 (dd, J = 8.96) [1H in total] H-3 5.59 (t, J = 10) 5.86 (dd, J = 9.6, 10.2) [1H in total] H-4 5.12 (t, J = 10) 5.11 (t, J = 10.2) [1H in total] H-5 4.66 (ddd, J = 1.2, 4.25 (ddd, J = 1.8, 7.2, 10.2) 6.6, 10) [1H in total] H-6 3.84 (dd, J = 1.2, 3.77 (dd, J = 1.8, 13.2) [1H in total] 13.2) 5.26 (dd, J = 6.6, 5.28 (dd, J = 7.2, 12.6) [1H in total] 12.6) Hexahydroxydiphenoyl (HHDP) -H 6.65 (1H) 6.49, 6.46 (1H in total) Galloyl-H 7.05 , 7.06 (2H in total) 6.99, 6.94 (2H in total)

Test Example 1 The compounds isolated in Example 1 were examined for active oxygen elimination activity in the same manner as in Reference Example 1. Also, for comparison,
Quercetin, known as an active oxygen-scavenging active substance,
The activities of catechin, epicatechin and ascorbic acid were similarly examined. Table 3 shows the test results.
Shown in

[0033]

[Table 3] From Table 3, it can be seen that both pedunclazine and terimagrandin I have significant active oxygen scavenging activity as compared to other comparatively active substances and other isolated substances (gallic acid, ellagic acid).

Test Example 2 Each compound isolated in Example 1 was examined for tyrosinase inhibitory activity in the same manner as in Reference Example 1. For comparison, the activity of arbutin, which is known as an inhibitory active substance, was similarly examined. Table 4 shows the test results.

[0035]

[Table 4] From Table 4, it can be seen that both pedunclazine and terimagrandin I have significant active oxygen scavenging activity compared to arbutin and other isolated substances (gallic acid, ellagic acid).

Test Example 3 100% of a 0.5% ethanol solution of the natural pigment shikonin
As a discoloration inhibitor, 0.1 g of a dried product of eucalyptus extract obtained by extracting 40% ethanol of dried eucalyptus leaves, pedunclazine or terimagrandin I obtained in Example 1 was added thereto, and the absorbance at 515 nm was used as an index. The time-dependent change in discoloration was measured, and the discoloration inhibition rate was determined from the following equation. The daily irradiation amount was set at 750 lux.

Discoloration suppression rate (%) = [(zy) / (x−
y)] × 100 x: Absorbance at 515 nm of shikonin before light irradiation y: Absorbance at 515 nm of shikonin after light irradiation in the absence of the test discoloration inhibitor z: Coexistence of the test discoloration inhibitor Absorbance of shikonin at 515 nm after light irradiation in the closed state

The higher the rate of inhibition of discoloration, the stronger the activity. For comparison, the discoloration inhibition rate was similarly determined for gallic acid, chlorogenic acid, and ascorbic acid, which are conventionally known to have a discoloration preventing effect. Table 5 shows the test results.

[0039]

[Table 5] From Table 5, the eucalyptus extract,
It can be seen that pedunkradin and terimagrandin I have high activities, and in particular, eucalyptus extract has a remarkable anti-discoloration effect.

Test Example 4 Safflower yellow was used in place of shikonin, and 400 n
The discoloration inhibition rate was determined in the same manner as in Test Example 3 except that the discoloration inhibition rate was determined from the absorbance at m. Table 6 shows the results.
Shown in

[0041]

[Table 6] From Table 6, it can be seen that, similarly to shikonin, eucalyptus extract, pedunclazine and terimagrandin I have a high activity, and in particular, eucalyptus extract has a remarkable anti-tarnish effect even when safflower yellow is used. Recognize.

Test Example 5 Dry extract of eucalyptus extract obtained in Reference Example 1, Example 1
The hyaluronidase inhibitory activity of peduncladin and terimagrandin I obtained in the above was measured. The test was carried out using bovine testis-derived hyaluronidase (Type IV manufactured by Sigma), mainly measuring the inhibitory effect of the compound 48/80 on the activation stage of the inactive enzyme.
The enzymatic activity is determined by the amount of N produced by the hydrolysis of hyaluronic acid.
-The increase in the reducing power of the tetrasaccharide having acetylhexosamine as the reducing end was measured by colorimetric quantification by the absorbance at 585 nm (Shokugeishin, Vol. 31, pp. 233-237,
1990). First, an appropriate amount of a test sample is dissolved in 100 μl of 0.1 M acetate buffer (pH 4.0), and is taken in a test tube.
0.10 mg of enzyme dissolved in 50 μl of the same buffer (100
NF unit) and incubated at 37 ° C. for 20 minutes. Then, 50 μg of the compound 48/80 dissolved in 100 μl of the same buffer as above was added, and the mixture was further added at 37 ° C. for 20 minutes.
Incubate for minutes.

Further, a 0.1 M acetate buffer (pH 4.
0) 200 μg of microorganism-derived sodium hyaluronate dissolved in 250 μl was added, and the cells were cultured at 37 ° C. for 40 minutes. Then, 100 μl of 0.4N NaOH was added, and after ice-cooling, 100 μl of borate buffer (pH 9.1) was added, and the mixture was boiled for 3 minutes. After ice-cooling, 3 ml of p-dimethylaminobenzaldehyde test solution was added, and 37 ° C. After culturing for 20 minutes, the absorbance at 585 nm was measured. As a control, the above acetate buffer was used in place of the sample solution. Further, as each blank, the above acetate buffer was used in place of the enzyme solution.

The inhibitory activity was represented by a hyaluronidase inhibitory rate determined by the following equation. Hyaluronidase inhibition rate (%) = ｛[(AB) − (C
-D)] / (AB)｝ × 100 A: Absorbance at 585 nm of control solution B: Absorbance at 585 nm of blank of control solution C: Absorbance of 585 nm of sample solution D: 585 nm of blank of sample solution Absorbance at The above activity is measured by changing the concentration of the sample substance step by step,
The concentration at which the inhibition rate was 50% was defined as the 50% inhibition rate (IC ₅₀ ). The smaller the value, the stronger the activity. The test results are shown below.

(Test sample) (IC ₅₀ ) pedunkradin 0.16 mg / ml terimagrandin I 0.10 mg / ml eucalyptus extract 0.54 mg / ml From the above test results, eucalyptus extract, pedunkradin and terimagrandin I Since it has a high hyaluronidase inhibitory activity, it has a moisturizing / water retaining effect, etc., and is useful in maintaining skin health in combination with the tyrosinase inhibitory activity.

[0046]

As described above, the active oxygen scavenger, skin preservative and discoloration inhibitor of the present invention are at least one selected from the group consisting of pedunkradin and terimagrandin I contained in plants such as Eucalyptus. Since the seeds are contained as an active ingredient, they are excellent in safety and also excellent in active oxygen scavenging activity, tyrosinase inhibitory activity, discoloration prevention activity and the like.

The skin preservative and discoloration inhibitor of the present invention containing an extract extracted from a tree of the genus Eucalyptus as an active ingredient are excellent in safety and excellent in tyrosinase inhibitory activity, discoloration inhibitory activity and the like. There is an effect that there is.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 35/78 A61K 35/78 C // C07H 13/08 C07H 13/08 (72) Inventor Hiroyuki Yamashita 1 Itikaichi, Ibaraki-shi, Osaka No. 3-30, Nagaoka Perfume Co., Ltd., Technology Development Laboratory (72) Inventor, Joichi Hayashi 1-3-30, Itikaichi, Ibaraki City, Osaka Prefecture, Nagaoka Perfume Co., Ltd., Technology Development Laboratory

Claims (5)

[Claims] 1. An active oxygen scavenger comprising at least one selected from pedunkradin and terimagrandin I as an active ingredient. 2. A skin preservative comprising at least one selected from pedunkradin and terimagrandin I as an active ingredient. 3. A skin preservative comprising a water-soluble extract extracted from a tree of the genus Eucalyptus as an active ingredient. 4. A discoloration inhibitor comprising at least one selected from pedunkradin and terimagrandin I as an active ingredient. 5. A discoloration inhibitor comprising, as an active ingredient, a water-soluble extract extracted from a eucalyptus tree.