KR20130035323A - Oral composition comprising saponin extracted from the root of camellia sinensis - Google Patents

Abstract

PURPOSE: An oral composition containing saponin extracted from the root of Camellia sinensis is provided to ensure anticancer effect, to prevent or treat periodontal diseases, and to suppress or treat halitosis. CONSTITUTION: An oral composition contains 0.01-65 wt% of saponin extracted from the root of Camellia sinensis. The saponin is triterpenoid saponin. Triterpenoid saponin prevents and treats periodontal diseases and suppresses halitosis. [Reference numerals] (AA) Oral physiotherapy index; (BB) Baseline; (CC) After 2 months; (DD) After 5 months; (EE) Comparative example 1; (FF) Example 1; (GG) Example 2;

Description

Oral composition comprising saponin extracted from the root of Camellia sinensis}

The present invention relates to an oral composition comprising saponin as an active ingredient.

More specifically, triterpenoid saponins, preferably triterpenoid saponins extracted from the roots of the tea tree as an active ingredient to minimize oral side effects and have excellent anti-inflammatory effect for periodontal disease improvement and oral composition for suppressing bad breath It is about.

Teeth are minerals composed of calcium phosphate, and the disease includes caries and periodontal disease. Among them, tooth decay is the largest part of dental diseases from children to adults, and the frequency of occurrence is increasing. According to the report of the Korean Dental Association, more than 90% of children experience dental caries and more than 80% of adults have periodontal disease.

In general, oral compositions designed to prevent periodontal disease were composed mainly of synthetic raw materials such as sodium chloride, allantoin chlorohydroxy aluminum, aminocaproic acid, tocopherol acetate. In recent years, however, many studies have been conducted to find and maximize the efficacy of folk traditional medicine using natural plants. It is applied.

Korean Laid-Open Patent No. 2002-0087672 contains a clove extract, which not only provides a refreshing feeling in the mouth, but also has an excellent effect in preventing bad breath and periodontal disease due to antibacterial activity, and has an analgesic effect that conventional detergents do not have. It is disclosed that there is.

Korean Laid-Open Patent No. 2002-0066042 relates to a composition for promoting oral hygiene containing a pomegranate extract, and confirmed that pomegranate extract has an excellent effect of inhibiting the generation of free radicals and nitric oxide, thereby promoting oral hygiene through such antioxidant effects. It is disclosed that the role is excellent.

Korean Laid-Open Patent No. 2001-0036152 relates to a method for producing a plant extract powder and a composition for oral cavity containing the plant extract powder prepared by the method, which is a medicinal plant extract that is more widely known in folks than artificial antibiotics and fungicides, In particular, it is disclosed that the use of pine needles can provide excellent periodontal disease and caries prevention effect in the oral cavity.

As described above, many plant extracts have been used in combination for the purpose of promoting oral hygiene, but in most cases, they have poor antimicrobial effects or simply through abstract efficacy such as anti-inflammatory, convergence, hemostasis, and blood circulation. It only shows the degree of preventing the occurrence of periodontal disease, there is a disadvantage in terms of stability was difficult to use as a composition for oral cavity.

Accordingly, the present inventors have completed the present invention by discovering that saponin extracted from the root of the tea tree can be usefully used to improve periodontal disease and inhibit bad breath while conducting various bioactive studies of tea. .

Therefore, the present inventors investigated and analyzed various plant extracts for the prevention and treatment of periodontal disease, and found that the triterpenoid saponin extracted from the root of the tea has excellent anti-inflammatory effect and no side effects using natural products, and completed the present invention. It was.

Accordingly, it is an object of the present invention to provide an oral composition for improving periodontal disease and inhibiting bad breath having an excellent anti-inflammatory effect by containing a triterpenoid saponin extracted from the roots of tea.

In order to achieve the above object, the present invention provides an oral composition for improving periodontal disease and inhibiting bad breath comprising triterpenoid saponin extracted from the root of the tea tree as an active ingredient.

The composition of the present invention has an anti-inflammatory effect by including triterpenoid saponin extracted from the root of the tea tree, and thus can prevent or treat periodontal disease and suppress or improve bad breath.

1 is a graph showing the dental plaque bacterial membrane index of the group using the triterpenoid saponin composition derived from the root of the tea tree through the degree of pigmentation in 120 subjects compared with the control group.
Figure 2 is a graph showing the gingivitis index of the group using the triterpenoid saponin composition derived from the roots of tea in 120 subjects compared to the control.
3 is a graph showing the bad breath occurrence index of the group using the triterpenoid saponin composition derived from the root of the tea tree in 120 subjects compared with the control group.

The present invention provides a composition for oral cavity containing saponin (saponin) derived from the roots of the tea tree.

Tea root-derived saponin used as an active ingredient in the present invention preferably comprises a triterpenoid saponin isolated from the extract of the root of the tea tree as an active ingredient, the triterpenoid saponins only prevent and improve periodontal disease It is effective in suppressing and improving bad breath.

The triterpenoid saponins used in the present invention are ten kinds of saponins isolated from the methanol extract of the tea tree root, and in the present invention, these are referred to as 'tea tree root-derived saponins R1 to R10'. These tea tree root-derived saponins R1 to R10 have the structures of the following Chemical Formulas 1 to 10.

The composition of the present invention preferably comprises the triterpenoid saponin in an amount of 0.01 to 65% by weight based on the total weight of the composition. If the content of the active ingredient is less than 0.01% by weight, the effect is less likely to appear, if the content exceeds 65% by weight can be irritated to the oral mucosa without increasing the effect depending on the content.

The main component of the tooth is calcium phosphate (calcium phosphate), and about 200 to 300 kinds of microorganisms are known to reside on the tooth surface, between teeth and gums of the root, and on the surface of the tongue. If oral hygiene is not performed properly, organic acid produced by Streptococcus microorganisms damages the dental hard tissue composed of calcium phosphate, causing various periodontal diseases such as caries and gingivitis. Deodorization is generated by generating volatile sulfide compounds, which are odor-causing substances, through demineralization enzymes or amino enzymes. Therefore, it has been reported that antibiotics such as penicillin can reduce periodontal disease caused by harmful microbial growth, but antibiotic resistance may occur over a long period of time, so it is not used in clinical practice.

Triterpenoid saponins derived from the roots of the tea tree are non-antibiotic agents that produce dental caries without side effects ( Streptococcus). mutans ) and Porphyromonas , a representative bacterium related to periodontal disease gingivalis ), as well as antimicrobial activity, Streptococcus mutans has been shown to inhibit the glucosyltransferase, a key enzyme in the process of causing dental caries. In addition, the antimicrobial activity against oral microorganisms has been found to reduce the occurrence of bad breath.

The composition for oral cavity of this invention is not specifically limited in the dosage form, For example, it may have formulations, such as a toothpaste, a mouthwash, oral cleansing agent.

For example, toothpaste may contain abrasives, wetting agents, foaming agents, binders, sweeteners, pH adjusting agents, preservatives, active ingredients, flavoring agents, brighteners, pigments, solvents and the like commonly used in the art.

The abrasive components include calcium carbonate, precipitated silica, aluminum hydroxide, calcium monohydrogen phosphate, and insoluble sodium metaphosphate, and these abrasives alone or in combination of two or more thereof, preferably 1 to 60% by weight, based on the total weight of the composition. 10 to 50% by weight is used.

Wetting agent components include glycerin, sorbitol solution, polyethylene glycol, and propylene glycol, and are used alone or in combination of two or more kinds by 20 to 60% by weight.

As the foaming agent, anionic and nonionic surfactants such as sodium lauryl sulfate, sodium lauryl sarcosinate, sucrose fatty acid ester, polyoxyethylene-cured castor oil, and polyoxyethylene polyoxypropylene copolymer may be used alone or in combination of two or more kinds thereof. 0.5 to 5% by weight, preferably 0.5 to 3% by weight is used.

As the binder, 0.1-5% by weight, preferably 0.1-2% by weight of sodium carboxymethyl cellulose, hydroxymethylcellulose, carrageenan, xanthan gum and sodium alginate may be used alone or in combination.

As a sweetening agent, saccharin sodium, aspartame, stevioside, xylitol, and licorice acid may be used alone or in combination of two or more thereof, and 0.05 to 5% by weight may be used.

Examples of pH regulators include sodium phosphate, disodium phosphate, trisodium phosphate, sodium pyrophosphate, sodium citrate, citric acid and tartaric acid, and as antiseptics, paraoxyanthinic acid methyl, paraoxybenzoic acid propyl and sodium benzoate alone or two or more kinds thereof are mixed. Use it.

The active ingredient includes sodium fluoride, sodium monofluorophosphate, tin fluoride, chlorohexidine, allantoin chlorohydroxy aluminate, aminocaproic acid, triclosan, cetylpyridium chloride, zinc chloride, pyridoxine hydrochloride and tocopherol acetate It is used by mixing two or more kinds, and mixed with a proper amount of peppermint oil, spearmint oil, menthol and anetol as a fragrance, titanium oxide as a brightener, food coloring as a pigment, and a solvent of purified water and ethanol. It is prepared according to a conventional toothpaste manufacturing method.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the following examples are only for illustrating the present invention, but the scope of the present invention is not limited thereto.

Reference Example 1 Isolation of Saponin from the Roots of Tea Tree

The roots of the tea tree were collected in November 2005 at Hannam-ri, Namwon-eup, Seogwipo-si, Jeju-do. The tea tree was chosen as a 20 year old Yabukita variety.

10 kg of fresh tea tree roots were cut into small pieces and soaked in 8 L of 80% aqueous MeOH and left at room temperature for 2 days, and this extraction method was repeated twice. The extracts were combined and concentrated in vacuo to give 540 g of a gummy brown residue. 100 g of the residue was separated by chromographie using a 10% increase of MeOH in H ₂ O (4 L each) from 0 to 100% as eluent in a C18 silica gel flash column and eleven fractions (A to K) was obtained. Of these, active fractions G (4 g) and H (10 g) were combined and chromatographed again on silica gel to obtain eight fractions (GH1 to GH8).

The enzyme inhibited saponin fraction GH5 (1.02 g) in the fractions was purified by C18 HPLC (eluent B; 50-60% aqueous MeCN) to give 9 saponins 1 (108 mg, t _R 19.9 min), 2 (92 mg, t _R 20.9 min), 3 (37 mg, t _R 23.3 min), 4 (60 mg, t _R 32.7 min), 5 (161 mg, t _R 35.7 min), 6 (113 mg, t _R 37.8 min), 7 (48 mg, t _R 39.4 min), 8 (33 mg, t _R 41.9 min), and 9 (56 mg, t _R 47.9 min). In addition, Samples 1 to 3 were obtained using Eluent A (40 to 49% aqueous MeCN) on C18 HPLC and Samples 4 to 8 using Eluent D (70 to 80% aqueous MeOH) (49 mg, 32 mg, 12 mg, 16 mg, 71 mg, 20 mg, 12 mg, and 9 mg). Fraction 9 was further purified by eluent C (55-60% aqueous MeCN) by HPLC, assay samples 9 (26 mg, t _R 43.3 min) and 10 (8 mg, t _R 62.7 min).

Ten isolated triterpenoid saponins are referred to as 'tea root-derived saponins R1 to R10', respectively, and specific analysis results are as follows.

Saponin R1 from tea tree root: white solid; Melting point 228-229 ° C .; [α] ²⁰ _D : -28.83 ( c 0.43, MeOH); IR (neat): ν _max = 3406, 1738, 1714, 1447, 1249, 1039 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.69 (3H, s, H-24), 0.87 (3H, t, J = 7.2 Hz, 2MB-H-4), 0.89 (3H, s, H-29), 1.00 (5H, 3H, s, H-25 and 2H, m, H-6), 1.01 (3H, s, H-26), 1.02 (1H, m, H _a -1), 1.03 (3H, d, J = 7.2 Hz, 2MB-H-5), 1.05 (3H, s, H-30), 1.07 (1H, m, H _a -7), 1.26 (1H, t, J = 10.4 Hz , H-5), 1.35 (1H, dd, J = 13.2, 5.2 Hz, H _a -19), 1.38 (1H, m, 2MB-H _a -3), 1.48 (1H, m, H _b -7) , 1.50 (3H, s, H-27), 1.56 (1H, m, 2MB-H _b -3), 1.64 (2H, m, H _b -1, H-9), 1.74 (1H, m, H _a -2), 1.84 (1H, m, H _b -2), 1.91 (3H, s, Ac), 1.96 (3H, s, Ac), 1.98 (2H, m, H-11), 2.23 (1H, m , 2MB-H-2), 2.25 (3H, s, Ac), 2.47 (1H, t, J = 14.2 Hz, H _b -19), 2.77 (1H, dd, J = 14.0, 4.0 Hz, H-18 ), 3.10 (1H, d, J = 11.2 Hz, H _a -28), 3.26 (1H, d, J = 11.2 Hz, H _a -23), 3.36 (1H, d, J = 11.2 Hz, H _b- 28), 3.42 (1H, t J = 8.0, Hz, GlcA-H-2), 3.54 (2H, m, GlcA-H-3 & Ara-H-3), 3.57 (1H, m, GlcA-H- 4), 3.58 (1H, m, Ara-H _a -5), 3.60 (1H, d, J = 11.2 Hz, H _b -23), 3.62 (1H, m, Ara-H-2), 3.63 (1H , m, H-3), 3.80 (1H, m, Ara- H-4), 3.82 (1H, m, GlcA-H-5), 3.90 (1H, m, Ara-H _b -5), 4.51 (2H, d, J = 7.2 Hz, GlcA-H-1, Ara -H-1), 5.16 (1H, d, J = 4.8 Hz, H-15), 5.29 (1H, d, J = 4.8 Hz, H-16), 5.30 (1H, d, J = 10.0 Hz, H -21), 5.52 (1H, d, J = 10.0 Hz, H-22), 5.59 (1H, brs, H-12); HR-TOF-ESI-MS: m / z = 1041.5258 [M + H] ⁺ (calcd. For C ₅₂ H ₈₀ O ₂₁ + H: 1041.5270).

Saponin R2 derived from the tea tree root: white solid; Melting point 229-230 ° C .; [α] ²⁰ _D : -37.61 ( c 0.545, MeOH); IR (neat): ν _max = 3314 ,, 1727, 1444, 1248, 1038 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.69 (3H, s, H-24), 0.91 (3H, s, H-29), 1.00 (3H, s, H-25), 1.01 ( 3H, s, H-26), 1.08 (3H, s, H-30), 1.26 (1H, m, H _a -19), 1.50 (3H, s, H-27), 1.71 (3H, s, Ang -H-5), 1.90 (3H, s, Ac), 1.91 (3H, d, J = 7.6 Hz, Ang-H-4), 1.93 (3H, s, Ac), 2.24 (3H, s, Ac) , 2.50 (1H, t, J = 14.0, H _b -19), 2.78 (1H, dd, J = 14.4, 4.0 Hz, H-18), 3.14 (1H, d, J = 10.8 Hz, H _a -28 ), 3.26 (1H, d, J = 10.8 Hz, H _a -23), 3.39 (1H, d, J = 10.0 Hz, H _b -28), 3.60 (1H, d, J = 10.8 Hz, H _b- 23), 3.63 (1H, m, H-3), 4.50 (2H, d, J = 7.2 Hz, GlcA-H-1, Ara-H-1), 5.18 (1H, d, J = 4.4 Hz, H -15), 5.28 (1H, d, J = 4.0 Hz, H-16), 5.38 (1H, d, J = 10.8 Hz, H-21), 5.60 (1H, brs, H-12), 5.61 (1H , d, J = 10.8 Hz, H-22), 6.08 (1H, q, J = 7.6 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 1039.5142 [M + H] ⁺ (calcd. For C ₅₂ H ₇₈ O ₂₁ + H: 1039.5114).

Saponin R3 from the root of the tea tree: white solid; Melting point 233-234 ° C .; [α] ²⁰ _D : -28.84 ( c 0.208, MeOH); IR (neat): ν _max = 3415, 1726, 1368, 1249, 1023 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.70 (3H, s, H-24), 0.91 (3H, s, H-29), 0.95 (3H, s, H-26), 1.01 ( 3H, s, H-25), 1.08 (3H, s, H-30), 1.35 (3H, s, H-27), 1.50 (1H, m, H _a -15), 1.74 (3H, s, Ang -H-4), 1.80 (1H , m, H b -15), 1.90 (3H, s, Ac), 1.93 (3H, d, J = 7.6 Hz, Ang-H-5), 2.20 (3H, s , Ac), 2.66 (1H, dd, J = 14.4, 4.8 Hz, H-18), 3.10 (1H, d, J = 10.8 Hz, H _a -28), 3.27 (1H, d, J = 10.8 Hz, H _a -23), 3.29 (1H, d, J = 10.8 Hz, H _b -28), 3.60 (1H, d, J = 10.8 Hz, H _b -23), 3.64 (1H, m, H-3) , 4.51 (2H, d, J = 7.2 Hz, GlcA-H-1, Ara-H-1), 5.10 (1H, brs, H-16), 5.46 (1H, brs, H-12), 5.50 (1H , d, J = 10.4 Hz, H-21), 5.58 (1H, d, J = 10.4 Hz, H-22), 6.08 (1H, q, J = 7.6 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 981.5094 [M + H] ⁺ (calcd. For C ₅₀ H ₇₆ O ₁₉ + H: 981.5059).

Saponin R4 derived from the tea tree root: white solid; Melting point 227-228 ° C .; [a] ²⁰ _D : -12.56 ( c 0.565, MeOH); IR (neat): ν _max = 3421, 1718, 1370, 1257, 1041 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.71 (3H, s, H-24), 0.88 (3H, s, H-29), 0.86 (3H, t, J = 8.4 Hz, 2MB- H-4), 0.98 (3H, d, J = 6.8 Hz, 2MB-H-5), 1.00 (3H, s, H-26), 1.02 (3H, s, H-25), 1.07 (3H, s , H-30), 1.38 (3H, s, H-27), 1.40 (1H, m, 2MB-H _a -3), 1.58 (1H, m, 2MB-H _b -3), 1.82 (3H, s , Ang-H-5), 1.96 (3H, d, J = 7.2 Hz, Ang-H-4), 2.22 (1H, m, 2MB-H-2), 2.32 (3H, s, Ac), 2.66 ( 1H, dd, J = 14.0, 4.0 Hz, H-18), 3.12 (1H, d, J = 10.8 Hz, H _a -28), 3.27 (1H, overlapped with solvent, H _a -23), 3.37 (1H , d, J = 10.8 Hz, H _b -28), 3.60 (1H, d, J = 10.4 Hz, H _b -23), 3.64 (1H, m, H-3), 3.99 (1H, d, J = 4.0 Hz, H-15), 4.51 (2H, d, J = 7.2 Hz, GlcA-H-1, Ara-H-1), 5.29 (1H, d, J = 4.0 Hz, H-16), 5.41 ( 1H, d, J = 10.4 Hz, H-21), 5.52 (1H, brs, H-12), 5.54 (1H, d, J = 10.4 Hz, H-22), 6.15 (1H, q, J = 6.8 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 1039.5471 [M + H] ⁺ (calcd. For C ₅₃ H ₈₂ O ₂₀ + H: 1039.5478).

Saponin R5 derived from the tea tree root: white solid; Melting point 231-232 ° C; [α] ²⁰ _D : + 4.35 ( c 0.46, MeOH); IR (neat): ν _max = 3395, 1711, 1442, 1256, 1039 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.85 (3H, s, H-29), 0.88 (3H, t, J = 7.2 Hz, 2MB-H-4), 1.01 (3H, s, H-25), 1.02 (3H, d, J = 6.0 Hz, 2MB-H-5), 1.04 (3H, s, H-26), 1.07 (3H, s, H-30), 1.13 (3H, s , H-24), 1.42 (1H, m, 2MB-H _a -3), 1.44 (3H, s, H-27), 1.60 (1H, m, 2MB-H _b -3), 1.85 (3H, s , Ang-H-5), 1.98 (3H, d, J = 6.8 Hz, Ang-H-4), 2.32 (1H, m, 2MB-H-2), 2.62 (1H, dd, J = 14.0, 4.0 Hz, H-18), 3.00 (1H, d, J = 10.4 Hz, H _a -28), 3.27 (1H, d, J = 10.8 Hz, H _b -28), 3.71 (1H, d, J = 4.0 Hz, H-15), 3.79 (1H, d, J = 4.8 Hz, H-16), 3.89 (1H, m, H-3), 4.32 (1H, d, J = 7.6 Hz, GlcA-H-1 ), 4.50 (1H, d, J = 6.4 Hz, Ara-H-1), 5.47 (1H, brs, H-12), 5.55 (1H, d, J = 10.4 Hz, H-22), 5.86 (1H , d, J = 10.4 Hz, H-21), 6.14 (1H, q, J = 7.2 Hz, Ang-H-3), 9.41 (1H, s, H-23); HR-TOF-ESI-MS: m / z = 995.5282 [M + H] ⁺ (calcd. For C ₅₁ H ₇₈ O ₁₉ + H: 995.5216).

Saponin R6 derived from the root of the tea tree: white solid; Melting point 229-230 ° C .; [α] ²⁰ _D : -9.56 ( c 0.23, MeOH); IR (neat): ν _max = 3424, 1728, 1538, 1456, 1229, 1070 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.86 (3H, t, J = 6.4 Hz, 2MB-H-4), 0.92 (3H, s, H-29), 0.99 (3H, d, J = 7.2 Hz, 2MB-H-5), 1.02 (3H, s, H-25), 1.04 (3H, s, H-26), 1.07 (3H, s, H-30), 1.10 (3H, s , H-24), 1.36 (H, dd, J = 13.6, 4.0 Hz, 2MB-H _a -3), 1.57 (1H, dd, J = 13.6, 7.2 Hz, 2MB-H _b -3), 1.39 ( 3H, s, H-27), 1.84 (3H, s, Ang-H-5), 1.97 (3H, d, J = 7.2 Hz, Ang-H-4), 2.24 (1H, m, 2MB-H- 2), 2.32 (3H, s, Ac), 2.64 (1H, dd, J = 14.4, 4.0 Hz, H-18), 3.12 (1H, d, J = 10.8 Hz, H _a -28), 3.34 (1H , d, J = 10.8 Hz, H _b -28), 3.90 (1H, dd, J = 8.8 & 2.8 Hz, H-3), 3.97 (1H, d, J = 4.8 Hz, H-15), 4.33 ( 1H, d, J = 7.6 Hz, GlcA-H-1), 4.49 (1H, d, J = 6.8 Hz, Ara-H-1), 5.28 (1H, d, J = 4.4 Hz, H-16), 5.41 (1H, d, J = 10.4 Hz, H-21), 5.54 (1H, d, J = 10.4 Hz, H-22), 5.55 (1H, brs, H-12), 6.16 (1H, q, J = 7.2 Hz, Ang-H-3), 9.40 (1H, s, H-23); HR-TOF-ESI-MS: m / z = 1037.5406 [M + H] ⁺ (calcd. For C ₅₃ H ₈₀ O ₂₀ + H: 1037.5321).

Saponin R7 derived from the tea tree root: white solid; Melting point 223-224 ° C; [a] ²⁰ _D : -13.01 ( c 0.315, MeOH); IR (neat): ν _max = 3407, 1714, 1370, 1249, 1039 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.86 (3H, t, J = 7.4 Hz, 2MB-H-4), 0.89 (3H, s, H-29), 0.98 (3H, s, H-25), 0.99 (3H, d, J = 7.2 Hz, 2MB-H-5), 1.00 (3H, s, H-26), 1.07 (3H, s, H-30), 1.16 (3H, s , H-24), 1.37 (3H, s, H-27), 1.38 (1H, m, 2MB-H _a -3), 1.56 (1H, m, 2MB-H _b -3), 1.82 (3H, s , Ang-H-5), 1.97 (3H, d, J = 7.2 Hz, Ang-H-4), 2.26 (1H, m, 2MB-H-2), 2.31 (3H, s, Ac), 2.66 ( 1H, dd, J = 14.8, 4.0 Hz, H-18), 3.12 (1H, d, J = 10.8 Hz, H _a -28), 3.34 (1H, d, J = 10.8 Hz, H _b -28), 3.68 (3H, s, 23-COOC H ₃ ), 3.96 (1H, d, J = 4.8 Hz, H-15), 4.03 (1H, dd, J = 11.6, 4.4 Hz, H-3), 4.30 (1H , d, J = 8.0 Hz, GlcA-H-1), 4.50 (1H, d, J = 6.8 Hz, Ara-H-1), 5.28 (1H, d, J = 4.4 Hz, H-16), 5.41 (1H, d, J = 10.4 Hz, H-21), 5.54 (1H, brs, H-12), 5.54 (1H, d, J = 10.8 Hz, H-22), 6.16 (1H, q, J = 7.0 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 1067.5492 [M + H] ⁺ (calcd for C ₅₄ H ₈₂ O ₂₁ + H: 1067.5427).

Saponin R8 derived from the tea tree root: white solid; Melting point 231-232 ° C; [a] ²⁰ _D : -8.62 ( c 0.105, MeOH); IR (neat): ν _max = 3411, 1722, 1441, 1242, 1073 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.84 (3H, s, H-29), 0.85 (3H, s, H-24), 0.88 (3H, t, J = 7.2 Hz, 2MB- H-4), 0.98 (3H, s, H-25), 1.01 (3H, s, H-26), 1.02 (3H, d, J = 7.2 Hz, 2MB-H-5), 1.05 (3H, s , H-23), 1.07 (3H, s, H-30), 1.41 (3H, s, H-27), 1.42 (1H, m, 2MB-H _a -3), 1.60 (H, m, 2MB- H _b -3), 1.84 (3H, s, Ang-H-5), 1.98 (3H, d, J = 7.2 Hz, Ang-H-5), 2.30 (1H, m, 2MB-H-2), 2.62 (1H, m, H-18), 2.99 (1H, d, J = 10.0 Hz, H _a -28), 3.18 (1H, dd, J = 9.2, 5.2 Hz, H-3), 3.30 (1H, overlapped with solvent, H _b -28), 3.73 (1H, d, J = 4.0 Hz, H-15), 3.80 (1H, d, J = 4.0 Hz, H-16), 4.41 (1H, d, J = 7.2 Hz, GlcA-H-1), 4.53 (1H, d, J = 6.8 Hz, Ara-H-1), 5.47 (1H, brs, H-12), 5.55 (1H, d, J = 10.0 Hz, H-22), 5.86 (1H, d, J = 10.0 Hz, H-21), 6.16 (1H, q, J = 7.2 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 981.5435 [M + H] ⁺ (calcd. For C ₅₁ H ₈₀ O ₁₈ + H: 981.5423).

Saponin R9 derived from the tea tree root: white solid; Melting point 232-233 ° C; [α] ²⁰ _D : -24.15 ( c 0.31, MeOH); IR (neat): ν _max = 3443, 1724, 1459, 1234, 1072 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.71 (3H, s, H-24), 0.84 (3H, t, J = 7.2 Hz, 2MB-H-4), 0.88 (3H, s, H-29), 0.95 (3H, s, H-26), 0.98 (3H, d, J = 6.8 Hz, 2MB-H-5), 1.01 (3H, s, H-25), 1.09 (3H, s , H-30), 1.32 (1H, m, 2MB-H _a -3), 1.37 (3H, s, H-27), 1.44 (1H, m, H _a -15), 1.57 (H, m, 2MB -H _b -3), 1.80 (1H, m, H _b -15), 1.83 (3H, s, Ang-H-5), 1.97 (3H, d, J = 7.2 Hz, Ang-H-4), 2.20 (1H, m, 2MB-H-2), 2.27 (3H, s, Ac), 2.66 (1H, dd, J = 14.0, 3.6 Hz, H-18), 3.08 (1H, d, J = 10.4 Hz , H _a -28), 3.29 (1H, overlapped with solvent, H _a -23), 3.32 (1H, overlapped with solvent, H _b -28), 3.60 (1H, d, J = 10.0 Hz, H _b -23 ), 3.63 (1H, m, H-3), 4.51 (2H, d, J = 7.2 Hz, GlcA-H-1, Ara-H-1), 5.15 (1H, brs, H-16), 5.45 ( 1H, brs, H-12), 5.54 (2H, s, H-21 and H-22), 6.16 (1H, q, J = 7.6 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 1023.5556 [M + H] ⁺ (calcd. For C ₅₃ H ₈₂ O ₁₉ + H: 1023.5529).

Saponin R10 from tea tree root: white solid; Melting point 232-233 ° C; [α] ²⁰ _D : -22.06 ( c 0.29, MeOH); IR (neat): ν _max = 3433, 1720, 1458, 1229, 1072 cm ⁻¹ ; ¹ H-NMR (400 MHz, CD ₃ OD): δ = 0.70 (3H, s, H-24), 0.85 (3H, t, J = 7.6 Hz, 2MB-H-4), 0.89 (3H, s, H-29), 0.95 (3H, s, H-26), 0.98 (3H, d, J = 6.8 Hz, 2MB-H-5), 1.01 (3H, s, H-25), 1.09 (3H, s , H-30), 1.36 (3H, s, H-27), 1.37 (1H, m, 2MB-H _a -3), 1.43 (1H, m, H _a -15), 1.55 (1H, m, 2MB -H _b -3), 1.81 (1H, m, H _b -15), 1.83 (3H, s, Ang-H-5), 1.96 (3H, d, J = 7.2 Hz, Ang-H-4), 2.22 (1H, m, 2MB-H-2), 2.27 (3H, s, Ac), 2.66 (1H, dd, J = 14.0, 4.0 Hz, H-18), 3.08 (1H, d, J = 10.8 Hz , H _a -28), 3.29 (1H, overlapped with solvent, H _a -23), 3.32 (1H, overlapped with solvent, H _b -28), 3.60 (1H, d, J = 10.8 Hz, H _b -23 ), 3.62 (1H, m, H-3), 3.77 (3H, s, GlcA-6-OC H ₃ ), 4.51 (2H, d, J = 7.2 Hz, GlcA-H-1, Ara-H-1 ), 5.16 (1H, brs, H-16), 5.46 (1H, brs, H-12), 5.54 (2H, s, H-21 and H-22), 6.16 (1H, q, J = 7.0 Hz, Ang-H-3); HR-TOF-ESI-MS: m / z = 1037.5684 [M + H] ⁺ (calcd. For C ₅₄ H ₈₄ O ₁₉ + H: 1037.5685).

 Examples 1-2 and Comparative Example 1 Preparation of Toothpaste Composition

Toothpaste compositions (Examples 1 to 2) and conventional toothpaste compositions (Comparative Example 1) of the present invention were prepared using the components shown in Table 1 as main components.

Ingredients Example 1 Example 2 Comparative Example 1 Function 17 17 17 Sodium fluoride 0.22 0.22 0.22 Sorbitol solution 50 50 50 Carboxymethyl Cellulose Sodium 1.0 1.0 1.0 Sodium lauryl sulfate 2.0 2.0 2.0 Methyl paraben 0.2 0.2 0.2 Combination fragrance 1.0 1.0 1.0 Zaccarin Sodium 0.2 0.2 0.2 Sodium citrate 0.4 0.4 0.4 Triterpenoid Saponins (Saponins R4-8 from Tea Root) 3.0 - - Triterpenoid Saponins (Saponins R1-10 from Tea Root) - 3.0 - Titanium dioxide 0.3 0.3 0.3 Purified water Balance Balance Balance

[Test Example 1] Tooth surface bacterial film index comparison test

This study was conducted on 120 subjects who were in the same environment. All the subjects underwent a first-order oral examination before the test to obtain a baseline. A single blind method was applied and all subjects were given the same dentifrice and toothbrush of the same standard during the residual effect removal period of 4 weeks prior to the experiment. A total of three measurements were taken at two-month intervals. The test method was to mix 10 ml of pigmented liquid with 20 ml of water, sprinkle for 1 minute in the mouth, spit it out, lightly brush with water, and apply the Turesky modification criteria of Quigley & Hein. The results are shown in Table 2 below.

group Subject base line
mean ± SD 2 months later
mean ± SD 5 months later
mean ± SD P value
(by ANOVA) Comparative Example 1 33 0.76 ± 0.58 0.78 ± 0.53 0.74 ± 0.50 p> 0.05 Example 1 33 0.77 ± 0.67 0.65 ± 0.31 0.61 ± 0.45 p <0.05 Example 2 33 0.76 ± 0.58 0.54 ± 0.41 0.45 ± 0.42 p <0.05

As a result of the first oral examination after the first two months, Comparative Example 1 showed an increase of 2.6% in the dental bacterial membrane index, but Example 1 and Example 2 showed a decrease of 15.6% and 28.9%, respectively. In the second microscopic oral examination result after 5 months, Comparative Example 1 showed a decrease of 2.6%, and Example 1 and Example 2 showed reductions in the dental plaque index of 20.8% and 40.8%, respectively (FIG. 1).

In the above results, it was shown that Example 1 and Example 2 reduced the bacterial plaque to a significant level compared to Comparative Example 1.

Test Example 2 Gingivitis Index Comparison Test

This study was conducted on 120 subjects who were in the same environment. All the subjects underwent a first oral examination before the test to determine the baseline. A single blind method was applied and all subjects were given the same dentifrice and toothbrush of the same standard during the residual effect removal period of 4 weeks prior to the experiment. A total of three measurements were made at intervals of two months, and the experimental method was calculated by dividing the gingival per tooth into the buccal and lingual surfaces and calculating the average value of the indexes. Each gingivitis was evaluated from 0 to 3 points according to Loe & Silness's grading criteria to calculate the gingivitis index for each tooth, and then the average gingivitis index of the individual was calculated. The results are shown in Table 3 below.

group Subject base line
mean ± SD 2 months later
mean ± SD 5 months later
mean ± SD P value
(by ANOVA) Comparative Example 1 33 0.62 ± 0.48 0.57 ± 0.47 0.57 ± 0.46 p> 0.01 Example 1 33 0.65 ± 0.22 0.43 ± 0.31 0.45 + 0.14 p <0.01 Example 2 33 0.60 ± 0.43 0.48 ± 0.25 0.41 ± 0.30 p <0.01

In the first precision oral examination result after the first two months, the gingivitis index showed a 8.1% decrease in Comparative Example 1, but Example 1 and Example 2 showed a decrease of 33.8% and 20.0%, respectively. 5 months later, the second oral examination result showed a 9% reduction in Comparative Example 1, and Examples 1 and 2 showed a decrease of 30.8% and 31.7%, respectively (FIG. 2).

From the above results, it was shown that Example 1 and Example 2 had decreased gingivitis index to a significant level compared to Comparative Example 1.

Test Example 3 Bad Breath Concentration Index

This study was conducted on 120 subjects who were in the same environment. All the subjects underwent a first oral examination before the test to determine the baseline. A single blind method was applied and all subjects were given the same dentifrice and toothbrush of the same standard during the residual effect removal period of 4 weeks prior to the experiment. A total of three measurements were made at intervals of two months.The measurement method was to shut the mouth for three minutes before measurement, connect the straw to Halimeter (model RH-17 (Interscan co, USA), set zero point to 0 ± 5ppb, and then The measurement was carried out according to the designated method, and the results are shown in Table 4 below.

group Subject base line
mean ± SD 2 months later
mean ± SD 5 months later
mean ± SD P value
(by ANOVA) Comparative Example 1 33 48.61 ± 35.27 48.21 ± 31.31 49.39 ± 38.49 p> 0.05 Example 1 33 47.32 ± 30.28 42.25 ± 35.50 40.25 ± 36.24 p <0.05 Example 2 33 48.98 ± 32.08 40.31 ± 31.24 36.74 ± 32.52 p <0.05

In the first two-month oral examination, the bad breath concentration index of Comparative Example 1 showed a decrease of 0.8%, and Examples 1 and 2 showed a decrease of 10.7% and 17.7%, respectively. After 5 months, the second oral examination showed Comparative Example 1 increased by 1.6%, and Example 1 and Example 2 showed 14.9% and 25.0% decrease, respectively (FIG. 3).

In the results, Example 1 and Example 2 showed a decrease in the gingivitis index to a significant level compared to Comparative Example 1.

As described above, the composition for oral cavity according to the present invention was excellent in reducing periodontal disease and periodontal disease, such as gingivitis and periodontitis when judged by the reduction of the gingivitis index and the effective value of the bad breath concentration index.

The composition for oral cavity according to the present invention may be prepared as in the following formulation example, but is not limited thereto.

Formulation Example 1 Toothpaste

Tea tree root-derived saponin R1-10 of Reference Example 1 is contained in an amount of 1 to 3% by weight of the total composition, and after adding a proper amount of flavoring, sweetening agent, thickener, abrasive and tartar remover, and adjusting the total amount with purified water, toothpaste Was prepared.

 Formulation Example 2 Oral Spray

10 mg of saponin R1-10 derived from the root of Reference Example 1 was added to purified water according to a conventional method for preparing oral spray, and after adding a flavor blocker and / or a flavoring agent at 0.75 to 7.5 wt% of the total composition, the total amount was 300 ml. It was adjusted to prepare an oral spray.

Claims (6)

Oral composition comprising tea tree root-derived saponin. The method of claim 1,
The saponin is a triterpenoid saponin composition for oral cavity. The method of claim 2,
The triterpenoid saponin is oral composition of one or more of the following Formula 1 to 10.
[Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Formula 10]

The method according to any one of claims 1 to 3,
The saponin is included in the composition for oral cavity in an amount of 0.01 to 65% by weight based on the total weight of the composition. A periodontal disease prophylactic or ameliorating agent comprising a composition according to any one of claims 1 to 3. A bad breath inhibitor or improver comprising a composition according to any one of claims 1 to 3.

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