KR101816638B1 - Oral composition comprising saponin extracted from the root of Camellia sinensis - Google Patents

Abstract

The present invention relates to an oral composition comprising saponin derived from root of tea, and more particularly to a composition for preventing or treating periodontal disease such as gingivitis or periodontitis by containing triterpenoid saponin extracted from a root of tea, Or an oral composition which is excellent in improving the efficacy.

Description

[0001] The present invention relates to an oral composition comprising saponin derived from root of tea root,

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

More particularly, the present invention relates to a composition for oral care for reducing periodontal disease and having an excellent anti-inflammatory effect by minimizing side effects and containing triterpenoid saponin, preferably triterpenoid saponin extracted from a root of tea, as an active ingredient .

The teeth are minerals made of calcium phosphate. The diseases are mainly tooth decay and periodontal diseases. Dental cavities are the largest part of dental disease from childhood to adult and are increasing in frequency. According to 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 include sodium chloride, allantoin chlorohydroxy aluminum, aminocaproic acid, and tocopherol acetate. However, in recent years, in the field of dentistry and medicine, numerous studies have been conducted to find out and maximize the utility of traditional traditional medicine using natural plants. As the effects on oral cavity have been known, many extracts have been used in oral compositions for improving periodontal disease Has been applied.

Korean Patent Publication No. 2002-0087672 has an excellent effect in removing bad breath due to antibacterial activity and preventing periodontal disease as well as providing a refreshing sensation in mouth gargle because it contains clove extract and has an analgesic effect not possessed by conventional detergents ≪ / RTI >

Korean Patent Publication No. 2002-0066042 relates to a composition for enhancing oral hygiene containing pomegranate extract, wherein the pomegranate extract has excellent antioxidative and antioxidant activity and thus promotes oral hygiene through the antioxidant effect The role is excellent.

Korean Patent Laid-Open Publication No. 2001-0036152 discloses a method for preparing a plant extract powder and an oral composition containing a plant extract powder prepared by the method. The present invention relates to a composition for oral use which is widely known in the arts than artificial antibiotics and fungicides, In particular, it is disclosed that pine needle can be used to provide excellent periodontal disease and tooth decay prevention effect in the oral cavity.

As mentioned above, many plant extracts have been used for the purpose of promoting oral hygiene. However, in most cases, they have a poor antimicrobial effect or they simply have abstract effects such as anti-inflammation, convergence, hemostasis, and promotion of blood circulation It shows only a degree of prevention of periodontal disease occurrence, and it has disadvantages in that it is insufficient in terms of stability, so that it has been difficult to use it as an oral composition.

Accordingly, the inventors of the present invention discovered that saponin extracted from the root portion of tea leaves can be used for the prevention of periodontal disease and inhibition of bad breath by inhibiting inflammation in the oral cavity during the study of various physiological activities of tea. .

Accordingly, the present inventors investigated and analyzed various plant extracts for the prevention and treatment of periodontal disease. As a result, they found that triterpenoid saponins extracted from tea roots had excellent antiinflammatory effect and had no side effects using natural products. Respectively.

Accordingly, an object of the present invention is to provide an oral composition for improving periodontal disease and inhibiting bad breath, which contains triterpenoid saponin extracted from a root of tea as an active ingredient and has excellent anti-inflammatory effect.

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 a root of tea, as an active ingredient.

The composition of the present invention has an anti-inflammatory effect by containing triterpenoid saponin extracted from the root of tea as an active ingredient, thus preventing or treating periodontal disease and suppressing or improving bad breath.

FIG. 1 is a graph showing the tooth surface bacterial film index of a group using a triterpenoid saponin composition derived from a root of a tea plant through comparison with a control group, based on the degree of coloring of teeth of 120 subjects.
FIG. 2 is a graph showing the gingival index of a group using a triterpenoid saponin composition derived from a root of tea from 120 subjects in comparison with a control group. FIG.
FIG. 3 is a graph showing the odor occurrence index of a group of 120 subjects, using a triterpenoid saponin composition derived from a root of tea, in comparison with a control group.

The present invention provides an oral composition comprising tea sap root derived saponin as an active ingredient.

The saponin derived from tea root used as an active ingredient in the present invention preferably contains triterpenoid saponin isolated from the extract of tea root, and the triterpenoid saponin prevents and improves periodontal disease But also has the effect of 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 root, and they are referred to as 'saponin R1 to R10' derived from the root of tea. The saponins R1 to R10 derived from these tea root roots have the following formulas (1) to (10).

The composition of the present invention preferably contains 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 be exhibited. If the content is more than 65% by weight, irritation may be given to the oral mucosa without increasing the content-dependent effect.

The teeth are composed of inorganic calcium phosphate (calcium phosphate), and about 200 ~ 300 kinds of microorganisms are known to reside on the surface of the tooth, between the tooth and gum of the root, and on the surface of the tongue. If the oral hygiene activities are not properly performed, the tooth hard tissues composed of calcium phosphate are damaged by the organic acids produced by the microorganisms of the Streptococcus strains, causing various periodontal diseases such as tooth decay and gingivitis, It produces volatile sulfide compounds, which are substances that cause odors through amino acids derived from deacylation enzymes and amino enzymes. Therefore, it is reported that antibiotics such as penicillin can reduce the periodontal disease caused by the growth of harmful microorganisms, but it is not used in the clinic since antibiotic resistance may occur during long-term use.

Triterpenoid saponins derived from tea root roots are non-antibiotics and have the potential to cause dental caries without side effects. Streptococcus mutans mutans ) and representative periodontal disease-related bacteria, Porphyromonas gingivalis ), as well as inhibiting glucosyltransferase, a key enzyme in the process of causing dental caries in Streptococcus mutans. It was also confirmed that the antimicrobial activity against oral microorganisms reduces the occurrence of halitosis substances.

The composition for oral use of the present invention is not particularly limited in its formulation, and specific examples thereof may include formulations such as toothpaste, mouthwash, mouthwash, and the like.

For example, in the case of dentifrices, it may contain abrasives, wetting agents, foaming agents, binders, sweeteners, pH adjusting agents, preservatives, medicinal active ingredients, flavoring agents, whitening agents, pigments and solvents commonly used in the art.

Examples of the abrasive component include calcium carbonate, precipitated silica, aluminum hydroxide, calcium monohydrogenphosphate and insoluble sodium metaphosphate. These abrasives may be used alone or in admixture of two or more, and may be used in an amount of 1 to 60% by weight, 10 to 50% by weight is used.

Examples of the wetting agent component include glycerin, sorbitol solution, polyethylene glycol and propylene glycol, and they are used alone or in admixture of 20 to 60% by weight.

Examples of the foaming agent include anionic and nonionic surfactants such as sodium lauryl sulfate, sodium lauryl sarcosinate, sucrose fatty acid ester, polyoxyethylene hardened castor oil, and polyoxyethylene polyoxypropylene copolymer, either singly or in combination 0.5 to 5 wt%, preferably 0.5 to 3 wt% is used.

As the binder, 0.1 to 5% by weight, preferably 0.1 to 2% by weight, of sodium carboxymethylcellulose, hydroxymethylcellulose, carrageenan, xanthan gum and sodium alginate are used alone or in admixture of two or more.

As the sweetening agent, it is preferable to use 0.05 to 5% by weight of sodium saccharin, aspartame, stevioside, xylitol and licorice acid, alone or in admixture of two or more.

Examples of the pH adjusting agent include sodium phosphate, disodium phosphate, sodium trisodium phosphate, sodium pyrophosphate, sodium citrate, citric acid and tartaric acid. Examples of the preservative include paraoxybenzoic acid methyl ester, paraoxybenzoic acid ester and sodium benzoate .

Examples of the active ingredient include sodium fluoride, sodium fluorophosphate, tin fluoride, chlorohexidine, allantoin chlorohydroxy aluminate, aminocaproic acid, triclosan chloride, cetylpyridinium chloride, zinc chloride, pyridoxine hydrochloride and tocopheryl acetate. A mixture of two or more of them is used as a flavor enhancer, and an appropriate amount of peppermint oil, spearmint oil, menthol and anethole is mixed and used as a flavor. Titanium oxide is used as a brightener, an edible pigment is used as a pigment, 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 intended to illustrate the present invention, but the scope of the present invention is not limited thereto

[Referential Example 1] Separation of Saponins Derived from Root Roots

The root of the tea was collected in November, 2005 in Nam - ri, Namwon - eup, Seogwipo city, Jeju - do, and the tea tree was selected as Yabukita variety 20 years old.

10 kg of fresh tea 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 gummy brown residue. 100 g of the residue was chromatographed on a C18 silica gel flash column using 10% increments of MeOH in H ₂ O (4 L each) from 0 to 100% as eluent to yield 11 fractions K). The active fractions G (4 g) and H (10 g) were combined and chromatographed again on silica gel color to obtain eight fractions (GH1 to GH8).

GH5 (1.02 g), an enzyme-inhibiting saponin fraction, was purified by C18 HPLC (eluent B; 50 to 60% aqueous MeCN) to give 9 saponins, 1 (108 mg, t _R 19.9 _{bun), 2 (92mg, t R} 20.9 bun), 3 (37mg, tR < / _{RTI >} 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 was obtained 39.4 min), 8 (33mg, t _R 41.9 min), and 9 (56mg, t _R 47.9 min). Samples 4-8 were also obtained on C18 HPLC using Eluent A (40-49% aqueous MeCN) and Eluent D (70-80% aqueous MeOH) using analytical samples 1-3 (49 mg, 32 mg, 12 mg, 16 mg, 71 mg, 20 mg, 12 mg, and 9 mg). The fractions 9, was further purified using eluent C (55 ~ 60% aqueous MeCN) to HPLC, analysis of a sample 9 (26mg, t _R 43.3 min) and 10 (8mg, tR &_lt; / RTI > 62.7 min).

The ten separated triterpenoid saponins are referred to as 'saponin root-derived saponins R1 to R10', respectively, and the results of analysis are as follows.

Saponin derived from root of tea root R1: white solid; Melting point 228 - 229 ° C; [?] ²⁰ _D : -28.83 ( c 0.43, MeOH); IR (neat):? _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 , 2.32 (3H, s, Ac), 2.47 (1H, t, J = 14.2 Hz, H _b -19), 2.77 (1H, dd, J = 14.0, 4.0 Hz, ), 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 - H), 3.42 (1H, t, J = 8.0, Hz, GlcA-H-2), 3.54 (2H, m, GlcA- 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 derived from root of tea root R2: white solid; Melting point 229 - 230 캜; ^{_{[α] 20 D: -37.61 (}} c 0.545, MeOH); IR (neat):? _Max = 3314, 1727, 1444, 1248, 1038 cm ^-1 ; ¹ H-NMR (400 MHz, CD ₃ OD):? = 0.69 (3H, s, H-24), 0.91 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 (3H, s, Ac), 1.91 (3H, d, J = 7.6 Hz, Ang-H-4), 1.93 , 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 - H, 1), 5.18 (1H, d, J = 4.4 Hz, H), 3.63 (1H, m, H-3), 4.50 (2H, d, J = 7.2Hz, GlcA- -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 derived from tea root root R3: white solid; Melting point 233 - 234 ° C; ^{_{[α] 20 D: -28.84 (}} c 0.208, MeOH); IR (neat):? _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 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 derived from root of tea root R4: white solid; Melting point 227 - 228 ° C; ^{_{[α] 20 D: -12.56 (}} c 0.565, MeOH); IR (neat):? _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 , 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 (AngH-5), 1.96 (3H, d, J = 7.2 Hz, Ang-H-4), 2.22 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 derived from root of tea root R5: white solid; Melting point 231 - 232 ℃; ^{_{[α] 20 D: + 4.35}} (c 0.46, MeOH); IR (neat):? _Max = 3395, 1711, 1442, 1256, 1039 cm ^-1 ; ¹ H-NMR (400 MHz, CD ₃ OD):? = 0.85 (3H, s, H-29), 0.88 (3H, t, J = 7.2 Hz, 2MB- H-25), 1.02 (3H, d, J = 6.0 Hz, 2MB-H-5), 1.04 (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 derived from root of tea root R6: white solid; Melting point 229 - 230 캜; [?] ²⁰ _D : -9.56 ( c 0.23, MeOH); IR (neat):? _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 and 2.8 Hz, H-3), 3.97 (1H, d, J = 4.8 Hz, 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 derived from root of tea root R7: white solid; Melting point 223 - 224 ° C; [?] ²⁰ _D : -13.01 ( c 0.315, MeOH); IR (neat):? _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, (3H, s, H-25), 0.99 (3H, d, J = 7.2 Hz, 2MB-H-5), 1.00 , 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 H-5), 1.97 (3H, d, J = 7.2 Hz, Ang-H-4), 2.26 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 derived from tea root root R8: white solid; Melting point 231 - 232 ℃; ^{_{[α] 20 D: -8.62 (}} c 0.105, MeOH); IR (neat):? _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 = (1H, d, J = 10.0 Hz, 1H), 4.53 (1H, d, J = 7.2 Hz, GlcA-H- 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 derived from root of tea root R9: white solid; Melting point 232 - 233 ° C; [?] ²⁰ _D : -24.15 ( c 0.31, MeOH); IR (neat):? _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 , 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- 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 derived from root of tea root R10: white solid; Melting point 232 - 233 ° C; [?] ²⁰ _D : -22.06 ( c 0.29, MeOH); IR (neat):? _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 , 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 to 2 and Comparative Example 1] Preparation of dentifrice composition

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

Ingredients Example 1 Example 2 Comparative Example 1 Function silicate 17 17 17 Sodium fluoride 0.22 0.22 0.22 Sorbitol solution 50 50 50 Sodium carboxymethylcellulose 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 Sodium saccharin 0.2 0.2 0.2 Sodium citrate 0.4 0.4 0.4 Triterpenoid saponin (saponin derived from tea root root R4-8) 3.0 - - Triterpenoid saponin (saponin derived from root of tea root R1-10) - 3.0 - Titanium dioxide 0.3 0.3 0.3 Purified water Balance Balance Balance

[Test Example 1] Comparison test of tooth surface bacterial film index

This study was conducted on 120 subjects who were in the same environment, and all of the subjects performed a first oral examination before the experiment to obtain a base line. A single blind method was applied and all subjects were given the same toothbrushes and toothbrushes of the same size during the period of eliminating the residual effect for 4 weeks before the experiment. The test method was as follows: 10 drops of dyestuff coloring solution was mixed with 20 ml of water, and the mixture was spit out for 1 minute in the mouth. After lightly brushing with water, the coloring state was applied by Quigley & Hein's Turesky modification standard, The results are shown in Table 2 below.

group Subject base line
mean ± SD Two months later
mean ± SD After 5 months
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 precision oral examination after the first two months, Comparative Example 1 showed an increase of 2.6% in the dental bacterial membrane index, whereas Example 1 and Example 2 showed a decrease of 15.6% and 28.9%, respectively. In the result of the second precision oral examination after 5 months, Comparative Example 1 showed a decrease of 2.6%, and Example 1 and Example 2 showed a decrease of the tooth surface bacteria index of 20.8% and 40.8%, respectively (Fig.

From the above results, it was shown that the bacterial membranes were decreased when the levels of both Example 1 and Example 2 were significantly higher than those of Comparative Example 1.

[Test Example 2] Comparison test of gingival index

This study was conducted on 120 subjects who were in the same environment. The baseline was obtained by conducting a first oral examination before the experiment. A single blind method was applied, and all subjects were given the same toothbrush and toothbrush of the same size during the period of eliminating residual effect for 4 weeks before the experiment. The gingiva was divided into two groups: the gingival perforation and the lingual surface, and the average value of the index was calculated. Each gingivitis was graded from 0 to 3 according to the criteria of Loe & Silness, and the gingivitis index of each tooth was obtained. The gingival index of the individual was calculated by the average score. The results are shown in Table 3 below.

group Subject base line
mean ± SD Two months later
mean ± SD After 5 months
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 two months after the first precision oral examination, the gingivitis index of Comparative Example 1 decreased by 8.1%, while that of Example 1 and Example 2 decreased by 33.8% and 20.0%, respectively. In the second precision oral examination after 5 months, Comparative Example 1 showed a decrease of 9%, and Example 1 and Example 2 showed a decrease of 30.8% and 31.7%, respectively (Fig. 2).

From the above results, it was shown that the gingival indexes of Example 1 and Example 2 were significantly lower than those of Comparative Example 1, respectively.

[Test Example 3]

This study was conducted on 120 subjects who were in the same environment. The baseline was obtained by conducting a first oral examination before the experiment. A single blind method was applied, and all subjects were given the same toothbrush and toothbrush of the same size during the period of eliminating residual effect for 4 weeks before the experiment. The measurements were made 3 times at 2-month intervals. The measurement was done for 3 minutes before measurement. After the mouth was closed, the straw was connected to a Halimeter (Model RH-17 (Interscan co, USA) The results are shown in Table 4 below.

group Subject base line
mean ± SD Two months later
mean ± SD After 5 months
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 months after the first oral oral test, the odor concentration index of Comparative Example 1 showed a decrease of 0.8%, and that of Example 1 and Example 2 decreased by 10.7% and 17.7%, respectively. After 5 months, the results of the second precision oral test showed that Comparative Example 1 increased by 1.6% and Example 1 and Example 2 decreased by 14.9% and 25.0%, respectively (Fig. 3).

The results showed that the gingival indexes of Examples 1 and 2 were significantly lower than those of Comparative Example 1, respectively.

As described above, the oral composition according to the present invention has excellent gingivitis and periodontal disease improving effect and bad breath suppressing effect when it is considered that the gingival index is decreased and the effective value of the bad breath index is decreased.

The composition for oral use according to the present invention can be prepared as in the following formulation examples, but is not limited thereto.

[Formulation Example 1] Toothpaste

Saponin R1-10 derived from root of Reference Example 1 was contained in an amount of 1 to 3% by weight of the total composition and the whole amount was adjusted with purified water after adding perfume, sweetener, thickeners, abrasive, .

 [Formulation Example 2] Oral spray agent

10 mg of saponin R1-10 derived from tea root root of Reference Example 1 was added to purified water according to a conventional oral spray preparation method, and 0.75 to 7.5% by weight of a total amount of a taste blocker and / or flavoring agent was added thereto. To prepare an oral spray.

Claims (6)

A composition for preventing and improving periodontal disease, comprising tea root root-derived triterpenoid saponin as an active ingredient,
Wherein the triterpenoid saponin is at least one of saponins represented by the following formulas (1) to (10).
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

The composition for preventing and improving periodontal disease according to claim 1, wherein the content of the triterpenoid saponin is 0.01 to 65% by weight based on the total weight of the composition. The composition for preventing and improving periodontal disease according to claim 1, wherein the composition is formulated as a toothpaste, an oral cleaning agent, or an oral cleaning agent. A composition for suppressing bad breath, comprising tea root root-derived triterpenoid saponin as an active ingredient,
Wherein the triterpenoid saponin is at least one of saponins represented by the following formulas (1) to (10).
[Chemical Formula 1]

(2)

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

5. The composition according to claim 4, wherein the content of the triterpenoid saponin is 0.01 to 65% by weight based on the total weight of the composition. 5. The composition according to claim 4, wherein the composition is formulated into a toothpaste, an oral cleaning agent, or an oral cleaning agent.

Images