KR20130109445A - Cosmetic composition of deodorant comprising essential oil from plant and polyphenol compound - Google Patents

Abstract

PURPOSE: A cosmetic composition for removing body odor is provided to suppress tyrosinase activity and melanogenesis using plant-derived essential oil and polyphenol compounds which remove radicals in body with a superior antioxidation activity. CONSTITUTION: A cosmetic composition for removing body odor contains plant-derived essential oil and polyphenol compounds as active ingredients. A plant is selected among peppermint, fragrant plantain, Hosta longipes (Franch. & Sav.) Matsum, Hemerocallis fulva, Convallaria keiskei Miq., and Cornus officinalis. The polyphenol compounds are derived from fragrant plantain and are selected among structural formulas 1-5. The polyphenol compounds suppress oxidation of palmitic acid.

Description

Cosmetic composition for removing body odor including essential oils and polyphenol compounds derived from plants {Cosmetic composition of deodorant comprising essential oil from plant and polyphenol compound}

The present invention relates to a cosmetic composition for removing body odor comprising an essential oil and a polyphenol compound derived from plants.

In general, sebaceous glands in human skin are secreted through the pores to the skin surface to prevent evaporation of moisture and maintain the elasticity of the skin. However, when the discharged sebum is in contact with the air on the surface of the skin, microorganisms on the skin multiply and thereby oxidize the sebum, thereby making the body bad. In particular, in older age, fatty acids in sebum are oxidized to lipid peroxidation, and odor is generated. 2-nonenal, which is a kind of volatile aldehyde produced from 9-hexadecenoic acid, which is increased among sebum in the middle-aged age, is senile odor. Is the main cause of

In order to reduce the odor, the body odor component is removed through a bath or air circulation in the room, a method of masking it through a fragrance and a deodorant, and the body odor component is adsorbed together with its precursor to volatilize the body odor component. The prevention method, the production itself from the precursor of the body odor component by the oxidation reaction or the activity of bacteria, and the like. The masking method using the above-mentioned fragrance and deodorant does not suppress the body odor component itself, and may cause undesirable new odor due to the mixture of the body odor and the fragrance component in question. It is difficult to solve the problem, and microorganism inhibitors, enzyme inhibitors, and sebum that can minimize odors by destroying and removing a certain amount of bacteria on the skin used to suppress the production and volatilization of body odors are prevented from being oxidized in the air. The main chemical components such as antioxidants have a weak deodorant effect, but serious problems such as causing irritation to the skin are emerging, and thus, it is urgent to develop a composition having safety and efficacy.

In addition, body odor includes eccrine sweat (apoccrine sweat), apocrine sweat (sebum), sebum, contaminants, and the like, and has a specificity that its cause and smell are different depending on body parts. In the case of odorants, which are the most troubling of body odor, odorless apocrine sweat is caused by the decomposition of axillary and airborne pathogens. There are many reports of microorganisms related to odor, but it is likely that odor is generated by lipophilic diphtheroid or large colony diphtheroid. In this way, it is decomposed by microorganisms, and volatile odorous substances are generated, including lower fatty acids such as caproic acid, caprylic acid, isovaleric acid, and butric acid. )), Ammonia, amines, indole, mercaptan, hydrogen sulfide, phosphine, steroids, etc., especially isogilic acid in lower fatty acids, and 5 alpha-androst- in steroids 16-en-3alpha-ol (5α-androst-16-en-3α-ol) and 5alpha-androst-16-en-3alpha-one (5α-androst-16-en-3α-one) It is known as the main cause. In addition, it is known that isobaric acid produced by the action of microorganisms in secreted eczema sweat is the main cause of the jizo.

Generally, a deodorant for a human body refers to a product that removes or prevents body odor generated in the human body, such as a bad smell such as an underarm odor (odor), foot odor (foot), sweat odor, , Stick type, powder type, granule type, liquid type and gel type.

These deodorants are classified into the following four principle.

(1) Physical deodorization method: A method of removing odors by ventilation and diffusion or adsorbing odors using a porous material such as activated carbon, zeolite or silica gel.

(2) Sensory deodorization method: A method of blocking odor by aromatic substances (fragrances).

(3) Chemical deodorization method: A method in which a deodorant is chemically reacted with a malodorous component to be odorless by neutralization reaction, addition reaction, condensation reaction and oxidation reaction.

(4) Biological deodorization method: Method of fundamentally preventing the cause of odor occurrence, such as sterilizing bacteria or bacteria causing odor occurrence or preventing corruption.

The physical deodorization method of (1) above is one of the widely used deodorization methods, and is widely used as a residential deodorant other than the human body, but it is ineffective in terms of feeling when used in the human body. The sensory deodorization method of (2) is a method of blocking odor by its own fragrance, but it is not only difficult to keep the balance of scent and odor in harmony, but also because the taste of the deodorant scent varies according to individuals. Not suitable for use In addition, the chemical deodorization method (3) can be effectively used for various odor components, but there is an inconvenience that it is necessary to pay attention to handling according to the used medicament. In addition, the biological deodorization method of (4) has not been able to obtain an expected effect after the odor has been generated. Thus, all of the four deodorization methods can not provide perfect deodorization and have been selected and applied according to the purpose of use.

In order to overcome the limited usability of such deodorants, various studies have been carried out on the main components thereof. For example, plant extracts are applied as deodorants. As a main prior art related thereto, Korean Patent Laid-Open Publication No. 2008-0089893 using an extract of a mixture of grapefruit, green tea and chitosan; Using at least one plant extract selected from the group consisting of non-leaf extracts, Puerariae Radix Extract, Ganoderma Lucidum Extract, Killer Extract, Irish Extract, Ginkgo Biloba Extract, Mulberry Extract, Licorice Extract, Sucrose Extract, 0043302; Korean Patent Laid-Open Publication No. 2005-0104884 using green tea extract and peony root extract; Korean Patent Laid-Open Publication No. 2001-007714 using wood vinegar is known. However, these prior arts have a disadvantage in that their effect is limited and unclear in actual body odor prevention. Therefore, it is urgent to develop a new deodorant component having excellent body odor removal effect and stable in the body and a functional cosmetic using the same.

Accordingly, the inventors of the present invention are to solve the problems of the prior art as described above, and if the body has an excellent deodorizing effect on the body odor, an object thereof is to provide a cosmetic composition having an antioxidant activity and a whitening effect.

It is therefore an object of the present invention to provide a cosmetic composition for body odor removal comprising essential oils and polyphenol compounds derived from plants as an active ingredient.

In order to achieve the above object, the present invention provides a cosmetic composition for body odor removal comprising a plant-derived essential oil and a polyphenol compound as an active ingredient.

In one embodiment of the present invention, the plant may be selected from the group consisting of peppermint, daylily, hibiscus, cone, lily of the valley and cornus.

In one embodiment of the present invention, the polyphenol compound may be any compound of the compound derived from the cornus oil, and represented by the structural formulas of the following <1> to <5>.

&Lt; Formula 1 >

(2)

<Formula 3>

&Lt; Formula 4 >

&Lt; Formula 5 >

In one embodiment of the present invention, the compound may be one having an antioxidant activity of palmitic acid.

In one embodiment of the present invention, the plant-derived essential oil may have DPPH radical scavenging ability, activate antioxidant enzymes SOD and CAT, have a whitening effect, and have no cytotoxicity.

In one embodiment of the present invention, the composition may be formulated as a soap, body wash, hand wash, aerosol, stick, roll-on, pump, sheet, patch, cream, lotion, gel or powder.

The present invention relates to a cosmetic composition for body odor removal comprising a plant-derived essential oil and a polyphenol compound as an active ingredient. Plant-derived essential oils and polyphenol compounds, which are effective ingredients of the body odor removing cosmetic composition according to the present invention, have an activity of removing radicals in the body, and thus have excellent antioxidant activity, and inhibit the production and activity of tyrosinase and melanin. It has a skin whitening effect, does not induce cytotoxicity to skin cell lines and has stability on skin as well as removes odor due to ammonia caused by nonenaldehyde and urination disorders, which in particular causes the elderly smell. Excellent activity as, there is an effect that can be usefully used in the production of functional cosmetics for body odor removal.

The present invention relates to a cosmetic composition for body odor removal comprising a plant-derived essential oil and a polyphenol compound as an active ingredient to deodorize, improve the odor caused by nonenaldehyde and urination disorders that cause the elderly odor.

In the present invention, a plant-derived essential oil was used as a raw material for the preparation of a cosmetic composition excellent in body odor removal effect, the plant can be used a plant selected from the group consisting of peppermint, daylily, hibiscus, cone, lily of the valley and cornus oil have. Particularly in the elderly, because it smells a characteristic of the elderly, itching is caused by the drying of the skin, the cosmetic composition according to the present invention is especially the basic cosmetics for seniors aged 60 years or older (soft cosmetics, skin lotion, nutrition cream, essence, body Lotion, moisture pack).

The essential oil, which is an active ingredient of the cosmetic composition for the purpose of removing body odor according to the present invention, can be extracted using any method known in the art for obtaining essential oils from natural products, for example, steam distillation. , Compression, absorption, solvent extraction, and the like can be used. In one embodiment of the present invention was used to extract essential oils from peppermint, daylily, bevy, cone, lily of the valley and cornus oil using steam distillation.

For the plant-derived essential oil obtained in the present invention, the present inventors first analyzed the antioxidant activity of these essential oil components in order to determine whether the functional cosmetic composition can be prepared using these components, in one embodiment of the present invention According to the results, essential oils extracted from peppermint, daylily, hibiscus, cone, lily of the valley, and cornus all have excellent antioxidant activity.

In addition, as a result of confirming that the essential oil component of the present invention can also be used for whitening through the effect of inhibiting tyrosinase activity on the skin, it was found that it has an activity of effectively inhibiting tyrosinase activity. Melanin production has also been shown to have inhibitory activity.

In addition, a cytotoxicity test was performed on skin cell lines, and no matter how much natural substances are used, it is necessary to investigate the stability of the skin cell line.

Therefore, the present inventors showed that the cytotoxicity test on the skin cells showed little toxicity to the cells. Therefore, it can be seen that it has a relatively high stability to the skin can be used as a cosmetic composition with confidence.

On the other hand, as the body ages, the skin of the human body tends to have a bad smell due to the aging process and the release of many wastes, especially non-aldehydes such as non-aldehydes, to the skin surface. In addition, many elderly people are easily released ammonia due to urination disorder, which also causes odor.

Accordingly, the present inventors have focused on polyphenol compounds as compounds capable of increasing the body odor-reducing effect as well as the essential oils described above for the development of functional cosmetics to reduce the odor causing such discomfort.

Therefore, in the present invention, while studying the polyphenolic compounds derived from plants, in particular peppermint, daylily, hibiscus, cone, lily of the valley and cornus for the manufacture of body odor reducing cosmetic composition that can be used exclusively for the elderly, separation from cornus and It was found that the five compounds identified were excellent in body odor inhibitory effects. The five compounds identified in the present invention are described in detail in Example 6 below.

In addition, the cosmetic composition provided in the present invention may contain a cosmetically or dermatologically acceptable medium or base. These are all formulations suitable for topical application, e.g. emulsions obtained by dispersing the oil phase in solutions, gels, solids, pasty anhydrous products, aqueous phases, emulsions obtained by dispersing the aqueous phase in oil phases, multi emulsions, suspensions, micro emulsions, micro It may be provided in the form of capsules, microgranules or ionic (liposomal) and nonionic vesicle dispersants, or in the form of creams, skins, lotions, powders, ointments, sprays, cleansers or concealed sticks. The composition according to the invention can also be used in the form of a foam, in the form of an aerosol composition further containing a compressed propellant or in the form of a patch. These compositions may be prepared according to conventional methods in the art.

The cosmetic composition may contain other ingredients in addition to the above-mentioned substances, preferably within the range of not impairing the main effect, and may have a synergistic effect on the main effect. Depending on the formulation or purpose of use, those skilled in the art can be appropriately selected and combined without difficulty.

For example, the cosmetic composition may contain a skin absorption promoting substance to increase the effect. In addition, the cosmetic composition of the present invention may include a material selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, sphingolipids and seaweed extract. In addition, the cosmetic composition of the present invention may include other components which are usually formulated into the cosmetic composition as necessary in addition to the essential components, and examples thereof include oil-fat components, humectants, emollients, surfactants, organic and inorganic pigments, Organic powders, ultraviolet absorbers, preservatives, fungicides, antioxidants, plant extracts, pH adjusters, alcohols, pigments, flavorings, blood circulation accelerators, cooling agents, restriction agents, purified water and the like. Other compounding components that can be included in the cosmetic composition of the present invention is not limited thereto, and the compounding amount of the above components is possible within a range that does not impair the object and effect of the present invention.

The formulation of the cosmetic composition is not particularly limited, and the formulation can be appropriately selected according to the purpose. For example, supple lotion, nourishing lotion, essence, nourishing cream, massage cream, pack, gel, makeup base, foundation, powder, lipstick, patch, spray, eye cream, eye essence, cleansing cream, cleansing foam, cleansing water, It may be prepared in one or more formulations selected from the group consisting of cleansers, body lotions, body creams, body oils and body essences, but is not limited thereto.

Hereinafter, the present invention will be described in more detail with reference to Examples. It will be apparent to those skilled in the art that these embodiments are merely illustrative of the present invention and that the scope of the present invention is not limited to these embodiments.

< Example  1>

Plant-derived essential oils

Steam distillation was used as a method of extracting essential oils from plants.The freshly cleaned plants, peppermint, daylily, hibiscus, cone, lily of the valley and cornus oil, were cut to size and put in distilled water in a circular flask with a steam distillation apparatus. Steam distillation for 5 hours. Distilled and collected in the upper layer and floral water in the lower layer containing the water-soluble essential oil components were separated and used in the refrigerator. At this time, 20 mL of essential oil was separated from the peppermint outpost, and the essential oil and daylily were extracted from the flower.

< Example  2>

Antioxidant Activity Measurement

Because plants are stuck, their ability to adapt to external stress is thought to be higher than that of other organisms, and they produce more antioxidants than other organisms. Cells have enzymatic and non-enzymatic defenses to protect their components and maintain redox status. Nonenzymatic defenses in plants include ascorbic acid, glutathione, a-tocoperol, and carotenoids, known as natural antioxidants. Enzymatic defenses include enzymes such as superoxide dismutase, catalase, ascorbate peroxidase, and glutathione reductase. The antioxidant enzyme activity of SOD, APX, and CAT in four species was measured. The results are shown in Table 1 below.

-Preparation of enzyme solution: Mix each biological sample in extraction buffer (50mM phosphate buffer, pH 7.0; 1% Tritox X-100; 1% PVP-40) at a ratio of 1: 4, homogenize, and centrifuge at 12000rpm for 20 minutes. After separation, the supernatant was taken and used for the measurement of sulfate activity. Protein quantitation was measured according to the BCA protein assay method using albumin as a standard.

-Catalase (CAT) activity measurement: Catalase activity was measured by Aebi (1984) method. 10 mM H ₂ O _{2 in} 50 mM potassium phosphate (pH 7.0) And a reaction enzyme solution were added. The absorbance change was observed at 240 nm for 2 minutes, and the amount of enzyme that degrades 1 uM of H ₂ O ₂ was 1 unit for 1 minute.

CAT is an antioxidant enzyme that rapidly processes harmful oxygen in vivo to protect cells and is a representative enzyme that decomposes and eliminates H ₂ O ₂ together with APX. It was the highest with 14.2U / mg protein in the daylily leaves, 13.6U / mg protein in the daylily flowers, 8.9U / mg protein, 8.8U / mg protein in the mint and cone flowers, and 7.8U / mg protein in the cone leaves, respectively. Low content.

-SOD (Superoxide dismutase) activity measurement: SOD activity was measured by applying the method of Beauchamp and Fridovich (1971). A solution containing 50 mM carbonic buffer (pH 10.2), 0.1 mM EDTA, 0.1 mM Xanthine, 0.025 mM nitroblue tetrazolium (NBT), and enzyme solution was reacted at 25 ° C for 10 minutes, followed by Xanthine oxidase (3.310-6 mM). The reaction was measured by. SOD activity was measured for 5 minutes at 550nm for 30 seconds.

SOD activity was the highest as 16.8U / mg protein in daylily flowers, 13.8U / mg protein in mint, 13.2U / mg protein, 12.4U / mg protein in daylily leaves and cone flowers, and 10.9U / in cone leaves, respectively. It was low in mg protein.

< Example  3>

Whitening effect measurement

Furthermore, the inventors performed a tyrosinase inhibitory effect (ie, whitening effect) analysis to confirm the whitening effect of daylily, beetle, cone, lily of the valley lilies, the results are shown in Table 2 below.

Experimental results showed that the extract of R. aeruginosa root, ground and lily of the valley showed relatively good in vitro tyrosinase inhibitory activity, and furthermore, to investigate alternative plants to supplement the in vitro tyrosinase inhibitory activity of Lilium extract, As a result of the analysis of the essential oil separated from the lemon and mint, a significant result was obtained from Gujeolcho, lemon and mint (see Table 3 below).

Sample Concentration (%) Tyrosinase inhibition activity (%) Agastache rugosa flower One 5.1 0.5 4.9 0.1 - Agastache rugosa leaf One 8.0 0.5 5.6 0.1 - Saururus chinensis One 25.7 0.5 14.9 0.1 11.9 Dendranthema zawadskii  there is. latilobum  ( Maxim .) Kitam . One 28.8 0.5 27.5 0.1 11.7 Citrus limon One 23.3 0.5 22.5 0.1 22.0 Isodon inflexus One 31.8 0.5 29.1 0.1 17.0 Vit .C One 62.9 0.5 62.6 0.1 61.0

< Example  4>

Melanin production inhibitory effect

Melanocytes cause skin diseases such as blemishes, freckles and melanoma by external and internal stimuli such as ultraviolet rays. Women are sensitive to these skin changes and interest in skin pigmentation is increasing day by day. Accordingly, research on the development of whitening materials that can function more stably and effectively is being conducted. Therefore, the present inventors investigated whether it affects melanin production in B16F10 melanoma cells using daylily, peppermint, cone and cornus.

① Toxicity test on cells of extract

B16F10 melanoma cell line is added to each well at a concentration of 1 × 10 ⁴ , and then after 1 day, each drug is added to a certain concentration. Each drug was treated and incubated for 4 hours by adding MTT solution (0.5 mg / mL) on day 2. The viable cells reacted with MTT to form purple insoluble formazan precipitate. To dissolve the supernatant, 150 µl of DMSO was dissolved and dissolved, and the absorbance was measured at 540 nm using an ELISA reader.

As a result, the extract concentration of viable cell concentration of 70% or more was 100ug / mL, and the melanin content inhibition ability was analyzed based on this concentration.

② Measurement of melanine production

Melanin is produced by a series of enzymatic reactions in the melanocytes, melanocytes. In this experiment, we determined the concentrations that did not affect the survival of B16F10 cells in the above experiments and examined the effects on melanin production in cornus, daylily, cone and peppermint extracts. Melanin quantification was used by modifying the method of Hosei et al. (Hosoi et al., 1985). B16 melanoma cells, which were melanocytes, were cultured and treated for 24 hours in each well at 1 × 10 ⁴ cells / well in a 24-well plate, followed by incubation for 48 hours. After 48 hours of incubation, each well was washed with PBS and dissolved in 1N NaOH solution with 1% DMSO for 1 hour at 60 ° C. The absorbance was measured at 405 nm using an ELISA reader.

As a result, melanin production was shown to decrease.

< Example  5>

Human keratinocytes ( keratinocyte  : HaCat Cell Effect on cell survival rate

The cell lines used in this experiment were Hacat cells of Skin Keratinocyte and were incubated in 37 ° C after adding 10% (V / V) Fetal Bovine Serum and Antibiotic (Antibicotic antimycotic) to DMEM (Dulbecco's odified Eagle Medium). The cell growth inhibitory activity of the sapphires (flowers, leaves, roots) and extracts of conical plants (outposts, roots) was confirmed by MTT assay. Inoculate 96well at a concentration of 3 × 104 cells / mL and incubate for 24 hours at 37 ° C., 5% CO 2 incubator, and then incubate for 24 hours by treating at a concentration of 25˜800 μg / mL. Thereafter, MTT was treated and cultured for 4 hours so that MTT was reduced by enzymatic action of viable cells. After that, the culture solution was removed, and the forman crystals formed in each well were dissolved by adding DMSO, and the absorbance was measured at 540 nm to determine cell viability. Although the effect of sapphire extract was low, it was found that the extract of Conical (Outpost) inhibited the cell viability of about 30% at the concentration of 800㎍ / mL.

< Example  6>

Antioxidant Active Compound Isolation

Among the five extracts, antioxidant compounds that can inhibit the oxidation of palmitoleic acid, the causative agent of 2-nonenal, were isolated from the extracts of the cornus fruit extract with the highest DPPH radical scavenging ability and SOD and CAT activity. It was.

<6-1> EtOH  Preparation of extracts and Solvent fraction  pharmacy

900 g of cornus fruit pulp was extracted twice with 50% Ethyl Alcohol (2 L) as a solvent, heated at 80 ° C for 3 hours using a Digital Heating Mantle, and the filtrate was concentrated under reduced pressure with a rotary evaporator to obtain a total extract of 307.5 g. . The total extract was suspended in 1.7 L of distilled water, and then fractionated three times by 1.7 L of the same amount of hexane sequentially, depending on the polarity of the solvent. The hexane layer was concentrated under reduced pressure again (Fig. 2). Repeated times to prepare fractions.

<6-2> EtOAc Fraction Silica column chromatography

The extract EtOAc fraction (78.3 g) was subjected to Silica gel column chromatography (30: 1 to 0: 1) using CH ₂ Cl ₂ : MeOH solvent to obtain a total of seven small fractions.

<6-3> Active fraction Sephadex LH -20 column chromatography

Antioxidant activity of the seven fractions isolated from the EtOAc fractions showed that the most active fraction 5 was obtained under the condition of MeOH: Water (1: 9 ~ 1: 0) using Sephadex LH-20 Column chromatography. Ten fractions were obtained from 10% to 100%.

<6-4> Compound of HPLC profile  analysis

Fraction 2, the most active of the seven fractions, was separated by Compound 5 using an HPLC system, RP-C18 (20 × 250 mm, 4 μm MeCN / H ₂ O + 0.1% Formic acid). In fraction 5, Compound 1 was separated by HPLC system from 50% fraction obtained by Sephadex LH-20 column chromatography. Compound 2 and Compound 3 were obtained in 60% and Compound 4 in 70%.

<6-5> HPLC Active substance separation and purification by

-Separation of Compound 1

Sephadex LH-20 column chromatography was performed using MeOH: Water solvent on fraction 5 of the 7 fractions obtained by dividing the EtOAc fraction by silica gel column chromatography. Then, 50% fractions separated from 10 fractions from 10% to 100% were extracted with mobile phase solvent MeCN: Water (33:67) using HPLC to obtain compound 1 (Loganin; 3,4,5-Trihydroxybenzoic acid; loganic acid). The results of analyzing the structure are as follows.

^{In the 1} H-NMR spectrum, the H-3 peak of the specific iridoid skeleton was identified at δ 7.42 (1H, s), and the carboxyl of C-11 was determined through δ 3.70 (3H, s) and δ 52.4 of the ¹³ C-NMR spectrum. It was found that carbon was substituted with a methyl group. Was also found that ¹ H-NMRspectrum at δ 4.67 (1H, d, J = 8.0Hz) C-NMR spectrum of the ¹³ glucose singnal δ 100.8, 79.3, 78.8 , 72.3, glucose glycosides from 63.5 (Fig.9). The above results were identified as Loganin in comparison with the literature values.

C ₁₇ H ₂₆ O ₁₀ , White amorphous powder, mp (° C.) 235-240, [α] D -83 (H 2 O). FABMS m / z 413 [M + Na] IR ν max (KBr, cm¹) 3460, 3300, 1710, 1650, 1430

¹ H-NMR (500 MHz, Acetone-d6): δ 1.12 (3H, d, J = 6.8 Hz, H-10), 1.65 (1H, m, H-6). 1.90 (1H, m, H-8), 2.06 (1H, m, H-6 ax ), 2.25 (1H, m, H-9), 3.15 (1H, m, H-5), 3.20-3.42 (4H , m, H-2, 3, 4, 5), 3.68 (1H, dd, J = 11.0, 5.2 Hz, H-6 a), 3.70 (3H, s, OCH₃), 3.93 (1H, dd, J = 11.0, 5.2 Hz, H-6 b), 4.06 (1H, t, J = 4.8 Hz, H-7, 4.67 (1H, d, J = 8.0 Hz, H-1), 5.30 (1H, d, J = 4.4 Hz, H-1), 7.42 (1H, s, H-3)

¹³ C-NMR (125 MHz, Acetone-d6): δ 170.3 (C-11), 152.9 (C-3), 114.8 (C-4), 100.8 (C-1), 98.5 (C-1), 79.3 ( C-5), 78.8 (C-3), 75.8 (C-7), 75.5 (C-2), 72.3 (C-4), 63.5 (C-6), 52.4 (OCH₃), 47.3 (C-9 ), 41.6 (C-6), 40.7 (C-8), 32.9 (C-5), 14.2 (C-10)

<Structure of Compound 1>

-Separation of Compound 2

The EtOAc fraction was separated by silica gel column chromatography. The fraction 5 of 7 fractions was subjected to Sephadex LH-20 column using MeOH: Water solvent. Thereafter, 10 fractions were obtained from 10% to 100%, and the separated 50% fractions were purified by mobile phase solvent MeCN: Water (35:65) to obtain Compound 2 ((7S) -O-Methylmorroniside). As follows.

In other words, the ¹ H-NMR spectrum and ¹³ C-NMR Spectrum showed similar characteristics to morroniside, and it was confirmed that the methoxyl group of δ 3.59 (3H, s) was substituted for C-7 in the ¹ H-NMR spectrum. Δ 4.65 (1H, d, J in ¹ H-NMR spectrum) = 2.8 Hz H-7), 1.42 (1H, td, J = 12.0, 3.6 Hz, H-6 _ax ), 1.82 (1H, dd, J = 14.0, 4.4 Hz, H-6eq) 7S was confirmed.

C ₁₈ H ₂₈ O ₁₁ , Yellowish oil, mp (° C.) 103-104, FABMS m / z 443 [M + Na] ⁺ ,

IR v _max (KBr, cm ¹ ) 3395, 2939, 1705, 1638, 1077

¹ H- NMR (500 MHz, CD ₃ OD): δ 1.25 (3H, d, J = 6.8 Hz, H-10). 1.42 (1H, td, J = 12.0, 3.6 Hz, H-6 _ax ), 1.72 (1H, m, H-9), 1.82 (1H, dd, J = 14.0, 4.4 Hz, H-6 _eq ), 2.95 (1H, dt, J = 12.4, 4.4 Hz H-5), 3.25 (3H, s, OCH ₃ ), 3.10-3.30 (4H, m, H-2,3, 4, 5), 3.59 (3H, s , OCH ₃ ), 3.79 (1H, m, H-6), 4.19 (1H, m, H-8), 4.65 (1H, d, J = 2.8 Hz, H-7), 4.70 (1H, d, J = 8.0 Hz, H-1), 5.80 (1H, d, J = 9.2 Hz, H-1, d, J = 9.2 Hz, H-1), 7.41 (1H, s, H-3)

¹³ C-NMR (125 MHz, CD ₃ OD): δ 167.3 (C-11), 153.0 (C-3), 110.2 (C-4), 98.7 (C-7), 98,1 (C-1) , 94.2 (C-1), 77.2 (C-5), 76.6 (C-3), 73.7 (C-3), 70.3 (C-4), 64.9 (C-8), 61.4 (C-6), 53.6 (7-OCH ₃ ), 50.3 (11-OCH ₃ ), 39.0 (C-9), 32.4 (C-6), 26.6 (C-5), 18,2 (C-10)

<Structure of Compound 2>

-Separation of Compound 3

The EtOAc fraction was separated by silica gel column chromatography. The fraction 5 of 7 fractions was subjected to Sephadex LH-20 column using MeOH: Water solvent. Then, 10 fractions were obtained from 10% to 100%, and the separated 50% fractions were purified by mobile phase solvent MeCN: Water (35:65) to obtain compound 3 ((7R) -O-Methylmorroniside). Is the same as

In other words, the ¹ H-NMR spectrum and ¹³ C-NMR Spectrum showed similar characteristics to morroniside, and it was confirmed that the methoxyl group of δ 3.59 (3H, s) was substituted for C-7 in the ¹ H-NMR spectrum. Δ 4.65 (1H, d, J in ¹ H-NMR spectrum) = 8.5 Hz H-7), 1.07 (1H, td, J = 13.1 Hz, H-6 _ax ), 1.91 (1H, dd, J = 11.5 Hz, H-6eq) were confirmed to be 7R by comparing with the literature values. (Fig. 13). The above results were identified as (7R) -O-Methylmorroniside in comparison with the literature values.

C ₁₈ H ₂₈ O ₁₁ , Yellowish oil, mp (° C.) 144-145, FABMS m / z 443 [M + Na] ⁺ , 443

IR v _max (KBr, cm ¹ ) 3396, 2923, 1702, 1640, 1407

¹ H- NMR (500 MHz, CD ₃ OD): δ 1.07 (1H, q, J = 13.1 Hz, H-6 _ax ). 1.31 (1H, d, J = 7.0, Hz, H-10), 1.70 (1H, m, H-9), 1.91 (1H, d, J = 11.5, Hz, H-6 _ax ), 2.73 (1H, dt, J = 13.0, 4.0 Hz H-5), 3.10-3.30 (4H, m, H-2,3, 4, 5), 3.40 (3H, s, OCH ₃ ), 3.60 (3H, s, OCH ₃ ), 3.79 (1H, d, J = 11.0 Hz, H-6), 3.86 (1H, d, J = 5.0 Hz, H-8), 4.40 (1H, d, J = 8.5 Hz, H-7), 4.70 (1H, d, J = 8.0 Hz, H-1), 5.70 (1H, d, J = 9.0 Hz, H-1), 7.41 (1H, s, H-3)

¹³ C-NMR (125 MHz, CD ₃ OD): δ 169.4 (C-11), 153.3 (C-3), 111.5 (C-4), 105.5 (C-7), 100.7 (C-1), 96.5 (C-1), 73.9 (C-5), 78.8 (C-3), 75.9 (C-2), 75.0 (C-4), 72.5 (C-8), 63.7 (C-6), 57.7 ( 7-OCH ₃ ), 52.6 (11-OCH ₃ ), 41.0 (C-9), 36.5 (C-6), 32.5 (C-5), 20,5 (C-10)

<Structure of Compound 3>

-Separation of Compound 4

The EtOAc fraction was separated by silica gel column chromatography. The fraction 5 of 7 fractions was subjected to Sephadex LH-20 column using MeOH: Water solvent. Thereafter, 10 fractions were obtained from 10% to 100%, and the separated 50% fractions were purified by mobile phase solvent MeCN: Water (43:57) to obtain compound 4 (Cornuside (7-galloylsecologanol)). Is the same as

That is, the H-3 peak of the specific iridoid skeleton was identified at δ 7.39 (1H, s) in the ¹ H-NMR spectrum, and the anomeric protone of δ 4.62 (1H, d, J = 8.0 Hz, H-1) and ¹³ From the glucose singnal of the C-NMR spectrum, the glucose glycoside was found. In addition, in the ^{1 H-NMR spectrum δ 7.03 (} 2H, s, H-2, 6) of galloyl moeity and δ 1.91 (1H, dq, J = 14.0, 6.5 Hz, H-6a), 2.00 (1H, dq, J = 14.0, 7.0 Hz, H-6b), 4.16 (2H, m, H-7) -O-CH ₂ -CH ₂ -system was confirmed.

C ₂₄ H ₃₀ O ₁₄ White amorphous powder, [a] _D -91 (MeOH), FABMS m / z 565 [M + Na] ⁺ , IR v _max (KBr, cm ^-1 ) 3394, 1693, 1624, 1315, 1240, 1076

¹ H-NMR (500 MHz, CD ₃ OD): δ 1,91 (1H, dq, J = 14.0, 6.5 Hz, H-6a), 2.00 (1H, dq, J = 14.0, 7.0 Hz, H-6b ), 2.58 (1H, dt, J = 8.5, 6.5 Hz, H-9), 2.86 (1H, q, J = 6.5, 4.9 Hz, H-5), 3.10 (1H, dd, J = 9.0, 8.0 Hz , H-2), 3.17 (1H, dd, J = 9.5, 9.0 Hz, H-4), 3.24 (1H, overlapped by the solvent signal, H-5), 3.29 (1H, t, J = 9.0 Hz, H-3), 3.52 (3H, s, CH ₃ ), 3.58 (1H, dd, J = 12.0, 6.0 Hz, H-6, a), 3.81 (1H, dd, J = 12.0, 2.0 Hz H-6b ), 4.16 (2H, m, H-7), 4.62 (1H, d, J = 8.0 Hz, H-1), 5.17 (1H, d, J = 10.5 Hz, H-10), 5.20 (1H, d , J = 17.5 Hz, H-10), 5.48 (1H, d, J = 6.5 Hz, H-1), 5.72 (1H, ddd, J = 17.5, 10.5, 8.5 Hz, H-8), 7.03 (2H , s, H-2, 6), 7.39 (1H, s, H-3)

¹³ C-NMR (125 MHz, CD ₃ OD): δ 31.0 (C-6), 32.4 (C-5), 46.1 (C-9), 52.5 (OCH ₃ ), 63.5 (C-6), 65.1 ( C-7), 72.3 (C-4), 75.4 (C-2), 78.7 (C-3), 79.1 (C-5), 98.4 (C-1), 100.9 (C-1), 110.9 (C -2, 6), 112.2 (C-4), 120.4 (C-10), 112.4 (C-1), 136, 4 (C-8), 140.5 (C-4), 147.2 (C-3, 5 ), 154.5 (C-3), 169.2 (C-7), 170.0 ( C OOCH ₃ )

<Structure of Compound 4>

-Separation of Compound 5

The EtOAc fraction was separated by silica gel column chromatography. The second fraction of the seven fractions was separated by mobile phase solvent MeCN: Water (9:92) using HPLC (Gallic acid (3,4,5-Trihydroxybenzoic acid)). The structural analysis results are as follows.

That is, only a singlet peak was confirmed at δ 7.11 (2H, s, galloyl-H) of the ¹ H-NMR spectrum. Five peaks were observed in the ¹³ C-NMR spectrum, and δ 146.4 (c-3,5) and δ 110.6 (C-2,6) were two-carbon integrals, indicating that they are symmetric aromatic compounds. Confirmed. In the ¹³ C-NMR spectrum, the carboxyl group was identified at δ 168.6 and the presence of three oxygenated aromatic carbons at δ 146.4 (C-3,5) and δ139.2 (C-4).

CHO, White amorphous powder, mp (° C) 258-265, EIMS m / z 170 [M] IR νmax (KBr, cm¹) 3392, 1687, 1616, 1427, 1330

¹ H-NMR (500MHz, CD ₃ OD): δ 7.11 (2H, s, galloyl-H)

¹³ C-NMR (125 MHz, CD ₃ OD): δ 110.6 (C-2, 6), 122.3 (C-1), 139.2 (C-4), 146.4 C-3, 5), 168.6 ( C = O)

<Structure of Compound 5>

< Example  7>

Of antioxidant active compounds DPPH radical Scatters  analysis

The structural analysis of ethyl acetate layer with the highest DPPH scavenging activity among the four solvent extracts of cornus fruits identified a total of five substances. DPPH radical scavenging ability was investigated to compare the antioxidative effects of the identified substances. The results are shown in Table 4 below.

[Table 4]

Assay, gallic acid (15.63 ug / ml), cornuside (33.82 ug / ml), (7R) -O-Methyl morroniside (250 ug / ml), (7S) -O-Methyl morroniside (250 ug / ml), And loganin (308 ug / ml). Gallic acid and cornuside showed the highest activity, and showed significantly higher antioxidant activity compared to the scavenging ability of the synthetic vitamin BHT used as a control.

The cytotoxicity of cisplatin used as an anticancer agent, gallic acid increased SOD-like activity and increased cell viability. In addition, the antioxidant effect was reported to be almost the same as vitamin E, which is consistent with the results of this experiment (Lim 2009).

In order to measure DPPH-radical scavenging activity, samples containing gallic acid at concentrations of 80 uM and 120 uM were found to be 22.2% (p <0.05) when treated with 80 uM gallic acid. The gallic acid treatment resulted in 57.6% (p <0.01). In particular, the activity of gallic acid of 120 uM was reported to be almost similar to 58.8% (p <0.01) of vitaminE activity of 30 uM (Seo et. al ., 2009).

< Example  8>

Caused by antioxidant compounds palmitoleic acid Of oxidative inhibitory activity

In order to analyze the antioxidant effects of cornus fractions and compounds, 0.1% BHT and 0, 10, 30, and 50ul of palmitoleic acid were added and stored at 50 ° C for 7 days, and the peroxide value was measured. Peroxide values of 60, 117, 140 and 187 meq / kg after 1, 3, 5 and 7 days of storage were 9, 23, 30 and 36 meq / kg with 10ul of 0.1% BHT. In the case of 10ul, 11, 33, 36 and 42 meq / kg was added, 8, 22, 27 and 30 meq / kg when 30ul was added, and 6, 20, 22 and 25 meq / kg when 50ul was added.

So far I looked at the center of the preferred embodiment for the present invention. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims. Therefore, the disclosed embodiments should be considered in an illustrative rather than a restrictive sense. The scope of the present invention is defined by the appended claims rather than by the foregoing description, and all differences within the scope of equivalents thereof should be construed as being included in the present invention.

Claims (6)

A cosmetic composition for removing body odor comprising an essential oil and a polyphenol compound derived from plants. The method of claim 1,
The plant is a body composition for removing body odor, characterized in that selected from the group consisting of peppermint, daylily, hibichu, cone, lily of the valley and cornus. The method of claim 1,
The polyphenolic compound is derived from cornus oil, cosmetic composition for body odor removal, characterized in that any one of the compounds represented by the structural formulas of the following <1> to <5>;
&Lt; Formula 1 >

(2)

(3)

&Lt; Formula 4 >

&Lt; Formula 5 >

. The method of claim 3,
The compound is a cosmetic composition for body odor removal characterized in that it has an antioxidant inhibitory activity of palmitic acid. The method of claim 1,
The plant-derived essential oil has a DPPH radical scavenging ability, activates antioxidant enzymes SOD and CAT, has a whitening effect, and has no cytotoxicity. The method of claim 1,
The composition is a body composition, soap, body wash, hand wash, aerosol, stick, roll-on, pump, sheet, patch, cream, lotion, gel or powder, characterized in that the cosmetic composition for removing body odor.