US20200078383A1 - Use of agarobiose or agarooligosaccharide having anticariogenic activity - Google Patents
Use of agarobiose or agarooligosaccharide having anticariogenic activity Download PDFInfo
- Publication number
- US20200078383A1 US20200078383A1 US16/349,885 US201716349885A US2020078383A1 US 20200078383 A1 US20200078383 A1 US 20200078383A1 US 201716349885 A US201716349885 A US 201716349885A US 2020078383 A1 US2020078383 A1 US 2020078383A1
- Authority
- US
- United States
- Prior art keywords
- agarobiose
- agarooligosaccharides
- oral
- xylitol
- streptococcus mutans
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- JPLATTLXZFUKRQ-UHFFFAOYSA-N Agarobiose Natural products OCC1OC(OC2C(O)COC2C(O)C=O)C(O)C(O)C1O JPLATTLXZFUKRQ-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 230000000170 anti-cariogenic effect Effects 0.000 title abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 35
- 239000000203 mixture Substances 0.000 claims description 38
- 239000008194 pharmaceutical composition Substances 0.000 claims description 33
- 208000025157 Oral disease Diseases 0.000 claims description 28
- 208000030194 mouth disease Diseases 0.000 claims description 28
- 229920000936 Agarose Polymers 0.000 claims description 25
- 235000013305 food Nutrition 0.000 claims description 17
- 208000002925 dental caries Diseases 0.000 claims description 12
- 239000000413 hydrolysate Substances 0.000 claims description 9
- 238000005227 gel permeation chromatography Methods 0.000 claims description 7
- MJQHZNBUODTQTK-WKGBVCLCSA-N (2s,3r,4s,5r,6r)-2-[[(1s,3s,4s,5s,8r)-3-[(2s,3r,4s,5s,6r)-2-[[(1s,3r,4s,5s,8r)-3,4-dihydroxy-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-2,6-dioxabicyclo[3.2.1]octan-8-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5- Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H]2OC[C@@H]1O[C@@H](O[C@@H]1[C@H]([C@H](O[C@H]3[C@H]4OC[C@@H]3O[C@@H](O)[C@H]4O)O[C@H](CO)[C@@H]1O)O)[C@H]2O MJQHZNBUODTQTK-WKGBVCLCSA-N 0.000 claims description 5
- 206010006326 Breath odour Diseases 0.000 claims description 5
- 208000032139 Halitosis Diseases 0.000 claims description 5
- 208000025865 Ulcer Diseases 0.000 claims description 5
- 208000005946 Xerostomia Diseases 0.000 claims description 5
- 206010013781 dry mouth Diseases 0.000 claims description 5
- 208000007565 gingivitis Diseases 0.000 claims description 5
- 201000001245 periodontitis Diseases 0.000 claims description 5
- 231100000397 ulcer Toxicity 0.000 claims description 5
- 241000194019 Streptococcus mutans Species 0.000 abstract description 51
- 239000000811 xylitol Substances 0.000 abstract description 48
- 229960002675 xylitol Drugs 0.000 abstract description 48
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 abstract description 46
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 abstract description 46
- 235000010447 xylitol Nutrition 0.000 abstract description 46
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 abstract description 46
- 230000012010 growth Effects 0.000 abstract description 34
- 238000004519 manufacturing process Methods 0.000 abstract description 18
- JWMBOBQNPBCYER-UHFFFAOYSA-N 4-[(4,8-dihydroxy-2,6-dioxabicyclo[3.2.1]octan-3-yl)oxy]-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound OC1C(CO)OC(O)C(O)C1OC1C(O)C(C2O)OCC2O1 JWMBOBQNPBCYER-UHFFFAOYSA-N 0.000 description 50
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 31
- 239000008103 glucose Substances 0.000 description 31
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 30
- 230000000694 effects Effects 0.000 description 17
- 230000002401 inhibitory effect Effects 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- 239000004310 lactic acid Substances 0.000 description 15
- 235000014655 lactic acid Nutrition 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 238000002835 absorbance Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000013361 beverage Nutrition 0.000 description 7
- 230000007423 decrease Effects 0.000 description 7
- 230000036541 health Effects 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 235000000346 sugar Nutrition 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002016 disaccharides Chemical class 0.000 description 6
- 235000013376 functional food Nutrition 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- -1 lactic acid Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 241000206572 Rhodophyta Species 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 238000007911 parenteral administration Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000606 toothpaste Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 235000003599 food sweetener Nutrition 0.000 description 4
- 239000000668 oral spray Substances 0.000 description 4
- 239000003765 sweetening agent Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000010306 acid treatment Methods 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 235000014633 carbohydrates Nutrition 0.000 description 3
- 230000010261 cell growth Effects 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 235000010980 cellulose Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 239000002324 mouth wash Substances 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 229920001542 oligosaccharide Polymers 0.000 description 3
- 150000002482 oligosaccharides Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000000340 Glucosyltransferases Human genes 0.000 description 2
- 108010055629 Glucosyltransferases Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241001149563 Streptococcus mutans ATCC 25175 Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 244000000010 microbial pathogen Species 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 235000013616 tea Nutrition 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 229940088594 vitamin Drugs 0.000 description 2
- 235000013343 vitamin Nutrition 0.000 description 2
- 239000011782 vitamin Substances 0.000 description 2
- 229930003231 vitamin Natural products 0.000 description 2
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
- XASQSRDYYCWSME-NWCCWNDLSA-N (2S,3R,4S,5R,6R)-4-[[(1S,3S,4S,5S,8R)-8-[(2S,3R,4S,5S,6R)-4-[[(1S,3S,4S,5R,8R)-4,8-dihydroxy-2,6-dioxabicyclo[3.2.1]octan-3-yl]oxy]-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-2,6-dioxabicyclo[3.2.1]octan-3-yl]oxy]-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O[C@@H]2O[C@H]3CO[C@H]([C@@H]3O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O[C@@H]4O[C@H]5CO[C@H]([C@@H]5O)[C@@H]4O)[C@H]3O)[C@@H]2O)[C@@H]1O XASQSRDYYCWSME-NWCCWNDLSA-N 0.000 description 1
- WZYRMLAWNVOIEX-MOJAZDJTSA-N (2s)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyacetaldehyde Chemical compound O=C[C@@H](O)[C@@H]1OC[C@H](O)[C@H]1O WZYRMLAWNVOIEX-MOJAZDJTSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- PKAUICCNAWQPAU-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid;n-methylmethanamine Chemical compound CNC.CC1=CC(Cl)=CC=C1OCC(O)=O PKAUICCNAWQPAU-UHFFFAOYSA-N 0.000 description 1
- DCQFFOLNJVGHLW-UHFFFAOYSA-N 4'-Me ether-Punctatin+ Natural products O1C(O)C(O)C2OCC1C2O DCQFFOLNJVGHLW-UHFFFAOYSA-N 0.000 description 1
- 241000606749 Aggregatibacter actinomycetemcomitans Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 208000002064 Dental Plaque Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 102000008100 Human Serum Albumin Human genes 0.000 description 1
- 108091006905 Human Serum Albumin Proteins 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002230 Pectic acid Polymers 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 241000605862 Porphyromonas gingivalis Species 0.000 description 1
- 241001135221 Prevotella intermedia Species 0.000 description 1
- 102000007327 Protamines Human genes 0.000 description 1
- 108010007568 Protamines Proteins 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000605 aspartame Substances 0.000 description 1
- 235000010357 aspartame Nutrition 0.000 description 1
- IAOZJIPTCAWIRG-QWRGUYRKSA-N aspartame Chemical compound OC(=O)C[C@H](N)C(=O)N[C@H](C(=O)OC)CC1=CC=CC=C1 IAOZJIPTCAWIRG-QWRGUYRKSA-N 0.000 description 1
- 229960003438 aspartame Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- FAPWYRCQGJNNSJ-UBKPKTQASA-L calcium D-pantothenic acid Chemical compound [Ca+2].OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O.OCC(C)(C)[C@@H](O)C(=O)NCCC([O-])=O FAPWYRCQGJNNSJ-UBKPKTQASA-L 0.000 description 1
- 229960002079 calcium pantothenate Drugs 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- WZYRMLAWNVOIEX-UHFFFAOYSA-N cinnamtannin B-2 Natural products O=CC(O)C1OCC(O)C1O WZYRMLAWNVOIEX-UHFFFAOYSA-N 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- MVPICKVDHDWCJQ-UHFFFAOYSA-N ethyl 3-pyrrolidin-1-ylpropanoate Chemical compound CCOC(=O)CCN1CCCC1 MVPICKVDHDWCJQ-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 230000002414 glycolytic effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- WRUGWIBCXHJTDG-UHFFFAOYSA-L magnesium sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Mg+2].[O-]S([O-])(=O)=O WRUGWIBCXHJTDG-UHFFFAOYSA-L 0.000 description 1
- 229940061634 magnesium sulfate heptahydrate Drugs 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- CNFDGXZLMLFIJV-UHFFFAOYSA-L manganese(II) chloride tetrahydrate Chemical compound O.O.O.O.[Cl-].[Cl-].[Mn+2] CNFDGXZLMLFIJV-UHFFFAOYSA-L 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- LCLHHZYHLXDRQG-ZNKJPWOQSA-N pectic acid Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)O[C@H](C(O)=O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](OC2[C@@H]([C@@H](O)[C@@H](O)[C@H](O2)C(O)=O)O)[C@@H](C(O)=O)O1 LCLHHZYHLXDRQG-ZNKJPWOQSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 235000013550 pizza Nutrition 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000010318 polygalacturonic acid Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000008057 potassium phosphate buffer Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229950008679 protamine sulfate Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ZUFQODAHGAHPFQ-UHFFFAOYSA-N pyridoxine hydrochloride Chemical compound Cl.CC1=NC=C(CO)C(CO)=C1O ZUFQODAHGAHPFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004172 pyridoxine hydrochloride Drugs 0.000 description 1
- 235000019171 pyridoxine hydrochloride Nutrition 0.000 description 1
- 239000011764 pyridoxine hydrochloride Substances 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 229960002477 riboflavin Drugs 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 229960000344 thiamine hydrochloride Drugs 0.000 description 1
- 235000019190 thiamine hydrochloride Nutrition 0.000 description 1
- 239000011747 thiamine hydrochloride Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- VJDOAZKNBQCAGE-VPENINKCSA-N xylitol 5-phosphate Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)COP(O)(O)=O VJDOAZKNBQCAGE-VPENINKCSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 235000016804 zinc Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/702—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7016—Disaccharides, e.g. lactose, lactulose
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
- A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres
- A23L33/25—Synthetic polymers, e.g. vinylic or acrylic polymers
- A23L33/26—Polyol polyesters, e.g. sucrose polyesters; Synthetic sugar polymers, e.g. polydextrose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/729—Agar; Agarose; Agaropectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
- A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
- A23V2200/312—Foods, ingredients or supplements having a functional effect on health having an effect on dental health
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2250/00—Food ingredients
- A23V2250/50—Polysaccharides, gums
- A23V2250/502—Gums
- A23V2250/5024—Agar
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Mycology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Physiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The present invention relates to a use of an agarobiose or agarooligosaccharides having anticariogenic activity. More specifically, a lower concentration of agarobiose or agarooligosaccharides than the concentration of xylitol suppresses the growth of Streptococcus mutans and suppresses acid production, and thus can be used for anti-cariogenic purposes.
Description
- The present invention relates to a use of agarobiose or agarooligosaccharides having an anticariogenic activity.
- Dental caries is one of the main causes of people visiting dentists and its incidence rate has increased due to the use of sugar as a sweetener in modern society. Streptococcus mutans is a major causative bacterium of dental caries (Loesche W J et al. (1975) Infect Immun. 11(6): 1252-60). Streptococcus mutans, which is a bacterium that resides in the human mouth, breaks sugar down, and secretes a glucosyltransferase (GTF) to form insoluble glucans on the tooth surface. Streptococcus mutans or various other bacteria are attached to the tooth surface to proliferate thereon. Bacteria on the tooth surface cause tooth decay as the enamel of the tooth surface is damaged by an organic acid such as lactic acid, which is a carbohydrate metabolite (Dashper S. G., et al. (1996) Microbiol. 142, 33-29). As representative materials for preventing dental caries by reducing the number of Streptococcus mutans in dental plaque, there are fluoride compounds and xylitol (Trahan L et al (1985) Caries Res. 19: 53-63). Xylitol, which is a 5-carbon alcohol present in nature, has sweetness similar to sugar and a sense of refreshment thereof. Due to these merits, xylitol is currently produced as gum, toothpastes, and the like and widely used, but it is disadvantageous in that the growth of Streptococcus mutans can be suppressed only in the case of including xylitol at a high concentration.
- Currently, research into natural materials having antimicrobial activity against Streptococcus mutans is increasingly conducted and there is a growing interest in natural sugars as an anti-cariogenic sweetener. However, research results on natural sugars which have an anticariogenic effect as much as xylitol are insufficient. When Streptococcus mutans ingests xylitol, xylitol-5-phosphate is formed by a phosphoenolpyruvate-xylitol phosphotransferase system (PEP-xylitol PTS). This inhibits the activity of a glycolytic enzyme and metabolism of xylitol no longer occurs, which is then extracellularly excreted. Through this process, bacterial growth and acid production are inhibited via a futile cycle that does not generate energy and only consumes energy. At this time, the growth of Streptococcus mutans can be inhibited only with xylitol having a concentration of 10 g/L or higher, and studies have also shown that resistant strains, the growth of which is not inhibited by xylitol, are produced when Streptococcus mutans is continuously cultured in a xylitol-containing medium (Trahan L et al (1985) Caries Res. 19: 53-63, Trahan L et al (1987) J Dent Res. 66: 982-988).
- An object of the present invention is to provide an anticariogenic use of agarobiose or agarooligosaccharides.
- To achieve the above technical object, the present invention provides a pharmaceutical composition for preventing or treating an oral disease, which includes one or more selected from the group consisting of agarobiose and agarooligosaccharides.
- The present invention also provides a use of agarobiose or agarooligosaccharides for preparing a pharmaceutical composition for preventing or treating an oral disease.
- The present invention also provides a method of preventing or treating an oral disease which includes administering a pharmaceutical composition for preventing or treating an oral disease to a subject.
- The present invention also provides an oral hygiene composition for preventing or alleviating an oral disease, which includes one or more selected from the group consisting of agarobiose and agarooligosaccharides.
- The present invention also provides a food composition for preventing or alleviating an oral disease, which includes one or more selected from the group consisting of agarobiose and agarooligosaccharides.
- The agarooligosaccharides may be obtained from an acid hydrolysate of agarose. More particularly, the agarooligosaccharides may be obtained by reacting agarose with a 0.1% (w/v) to 5% (w/v) strong acid at 80° C. to 140° C. for 5 minutes to 30 minutes and adding a strong base to the resulting reaction product to be neutralized to a pH of 5 to 6.
- The strong acid may be selected from the group consisting of phosphoric acid, sulfuric acid, hydrochloric acid, and nitric acid.
- The neutralization process may be performed by adding a strong base to the strong acid-treated agarose to adjust a pH thereof to 5 to 6.
- The strong base may be selected from the group consisting of NaOH, KOH, Ca(OH)2, and Ba(OH)2.
- The agarooligosaccharides may be a mixture of agarobiose, agarotetraose, agarohexaose, and agarooctaose.
- The agarobiose may be obtained by separating and purifying an acid hydrolysate of agarose through gel permeation chromatography.
- The agarobiose or agarooligosaccharides may inhibit the growth of Streptococcus mutans, which is an oral bacterium, and the production of acid by carbon source consumption of Streptococcus mutans.
- The oral disease may be any one selected from the group consisting of dental caries, gingivitis, periodontitis, oral mucous ulcers, halitosis, and xerostomia.
- Agarobiose or agarooligosaccharides of the present invention has been verified to inhibit the growth and acid production of Streptococcus mutans, and thus is anticipated to be applied to the development field of oral hygiene products such as toothpastes, mouthwashes, oral sprays, and the like, foods such as gum, candies, and the like, and medicines.
-
FIG. 1 illustrates an effect of a single carbon source on the growth of Streptococcus mutans in a minimal medium (substrate conditions: 10 g/L of glucose; No carbon; 10 g/L of xylitol; 10 g/L of agarobiose; 10 g/L of agarooligosaccharides (a mixture of oligosaccharides having degrees of polymerization of 2, 4, 6, and 8); and 10 g/L of neoagarobiose). -
FIG. 2 illustrates concentration-dependent inhibitory effects of xylitol (A), agarobiose (B), agarooligosaccharides (C), and neoagarobiose (D) on the growth of Streptococcus mutans in a minimal medium containing 10 g/L of glucose. -
FIG. 3 illustrates results of analyzing consumed glucose when each of xylitol (A), agarobiose (B), agarooligosaccharides (C), and neoagarobiose (D) was added to a minimal medium containing 10 g/L of glucose at various concentrations. -
FIG. 4 illustrates results of analyzing produced lactic acid when each of xylitol (A), agarobiose (B), agarooligosaccharides (C), and neoagarobiose (D) was added to a minimal medium containing 10 g/L of glucose at various concentrations. - The inventors of the present invention produced agarooligosaccharides as a mixture of oligosaccharides having degrees of polymerization of 2, 4, 6, and 8 through acid hydrolysis of agarose, and then used the agarooligosaccharides as a carbon source for Streptococcus mutans. In addition, only an agarobiose disaccharide consisting of D-galactose and 3,6-anhydro-L-galactose was separated and purified and used as a carbon source for Streptococcus mutans. The inventors conducted research on an anticariogenic effect of agarobiose by observing whether agarobiose, which was accurately quantified using an agarobiose quantification method using HPLC, inhibited the growth and acid production of Streptococcus mutans. As controls, glucose, xylitol, and neoagarobiose were used as carbon sources to conduct comparative experiments.
- As a result, it was verified that agarobiose and agarooligosaccharides of the present invention, which are capable of inhibiting cell growth, had an anticariogenic effect at a lower concentration than that of xylitol, which is known to be capable of inhibiting the growth of Streptococcus mutans. Red algae-derived agarooligosaccharides and agarobiose were produced through acid treatment and separation and purification processes, and then used as carbon sources to observe effects thereof on the growth of Streptococcus mutans by comparing with an effect of glucose, xylitol, or neoagarobiose as a carbon source on cell growth. In addition, agarobiose, agarooligosaccharides, xylitol, or neoagarobiose was added to a medium containing 10 g/L of glucose at various concentrations to observe the growth and acid production of Streptococcus mutans under mixed carbon source conditions. Through these experiments, it was first verified that purified agarobiose had a high inhibitory effect on the growth of Streptococcus mutans and an effect of inhibiting acid production at a lower concentration than that of commonly known xylitol. It was also verified that agarooligosaccharides had a stronger effect of inhibiting the growth and acid production of Streptococcus mutans than xylitol at a specific concentration or higher.
- Therefore, the present invention provides a pharmaceutical composition for preventing or treating an oral disease, which includes one or more selected from the group consisting of agarobiose and agarooligosaccharides.
- The present invention also provides a use of agarobiose or agarooligosaccharides for preparing a pharmaceutical composition for preventing or treating an oral disease.
- The agarooligosaccharides may be obtained through acid hydrolysis of red algae biomass-derived agarose.
- More particularly, the agarooligosaccharides may be obtained by reacting agarose with a 0.1% (w/v) to 5% (w/v) strong acid at 80° C. to 140° C. for 5 minutes to 30 minutes and adding a strong base to the resulting reaction product to be neutralized to a pH of 5 to 6.
- The concentration of the strong acid may range from 0.1% (w/v) to 5% (w/v), more particularly 0.5% (w/v) to 2% (w/v).
- The acid treatment reaction conditions may be a reaction between a 0.1% (w/v) to 5% (w/v) strong acid and agarose at 80° C. to 140° C. for 5 minutes to 30 minutes, more particularly a reaction between a 0.5% (w/v) to 2% (w/v) strong acid and agarose at 100° C. to 140° C. for 5 minutes to 20 minutes.
- The strong acid may be phosphoric acid, sulfuric acid, hydrochloric acid, nitric acid, or the like. More particularly, the strong acid may be phosphoric acid.
- The amount of the agarose used in strong acid treatment may be in a range of 10% (w/v) to 37% (w/v), particularly 15% (w/v) to 31% (w/v), and more particularly 16.8% (w/v) to 30.7% (w/v), with respect to a dry weight. When the amount of the agarose is within the above range, a liquefaction rate of 90%, 95%, or 98% or higher may be obtained. When the amount of the agarose is outside the above range, a substrate degradation rate may be significantly reduced.
- A strong base is added to the strong acid-treated agarose to be neutralized to a pH of 5 to 6.
- As the strong base, NaOH, KOH, Ca(OH)2, Ba(OH)2, or the like may be used, but the present invention is not limited thereto.
- The agarooligosaccharides, which are obtained through the acid hydrolysis of agarose, may be a mixture of agarobiose, agarotetraose, agarohexaose, and agarooctaose.
- The agarobiose used in the pharmaceutical composition of the present invention may be obtained by separating and purifying an acid hydrolysate of agarose through gel permeation chromatography.
- The gel permeation chromatography may be Bio-gel P2 chromatography.
- The pharmaceutical composition of the present invention may further include a pharmaceutically acceptable carrier.
- The pharmaceutically acceptable carrier includes carriers and vehicles commonly used in the medical field, and examples thereof include, but are not limited to, ion exchange resins, alumina, aluminum stearate, lecithin, serum proteins (e.g., human serum albumin), buffer substances (e.g., phosphates, glycine, sorbic acid, potassium sorbate, and partial glyceride mixtures of saturated vegetable fatty acids), water, salts or electrolytes (e.g., protamine sulfate, disodium hydrogen phosphate, potassium hydrogen phosphate, sodium chloride, and zinc salts), colloidal silica, magnesium trisilicate, polyvinyl pyrrolidone, cellulose-based substrates, polyethylene glycol, sodium carboxymethylcellulose, polyarylate, waxes, polyethylene glycol, and wool fat.
- In addition, the pharmaceutical composition of the present invention may further include, in addition to the above-described ingredients, a lubricant, a wetting agent, an emulsifying agent, a suspending agent, a preservative, or the like.
- In one embodiment, the pharmaceutical composition according to the present invention may be formulated in the form of various preparations suitable for oral administration or parenteral administration.
- Non-limiting examples of the preparations for oral administration include troches, lozenges, tablets, aqueous suspensions, oily suspensions, prepared powders, granules, emulsions, hard capsules, soft capsules, syrups, and elixirs.
- To formulate the pharmaceutical composition of the present invention for oral administration, a binder such as lactose, saccharose, sorbitol, mannitol, starch, amylopectin, cellulose, gelatin, or the like; an excipient such as dicalcium phosphate or the like; a disintegrating agent such as corn starch, sweet potato starch, or the like; a lubricant such as magnesium stearate, calcium stearate, sodium stearyl fumarate, polyethylene glycol wax, or the like; or the like may be used, and a sweetener, a fragrance, syrup, or the like may also be used.
- Furthermore, in the case of capsules, in addition to the above-mentioned substances, liquid carriers such as fatty oils may be further used.
- Non-limiting examples of the preparations for parenteral administration include injections, suppositories, respiratory inhalation powders, aerosols for sprays, oral sprays, oral cleansers, toothpastes, ointments, powder for application, oils, and creams.
- To formulate the pharmaceutical composition of the present invention for parenteral administration, sterilized aqueous solutions, non-aqueous solvents, suspensions, emulsions, freeze-dried preparations, agents for external application, or the like may be used, and as the non-aqueous solvents and the suspensions, propylene glycol, polyethylene glycol, a vegetable oil such as olive oil, an injectable ester such as ethyl oleate, or the like may be used.
- In addition, more particularly, when the pharmaceutical composition of the present invention is formulated as an injection, the composition of the present invention may be mixed in water with a stabilizer or a buffer to be prepared into a solution or a suspension, which is then formulated into a unit dosage form such as an ampoule or a vial. In addition, when the pharmaceutical composition of the present invention is formulated as an aerosol, a propellant or the like may be mixed with an additive to disperse a water-dispersed concentrate or wet powder.
- In addition, when the pharmaceutical composition of the present invention is formulated as an ointment, a cream, or the like, the pharmaceutical composition may be formulated using a carrier such as an animal oil, a vegetable oil, wax, paraffin, starch, tragacanth, cellulose derivatives, polyethylene glycol, silicone, bentonite, silica, talc, zinc oxide, or the like.
- A pharmaceutically effective amount and an effective dose of the pharmaceutical position of the present invention may vary depending on the formulation method, administration method, administration time and/or administration route, or the like, and may vary according to various factors including the type and degree of the reaction to be achieved via administration of the pharmaceutical composition, the type of individual to which the composition is administrated, age, body weight, general health conditions, the symptoms or severity of diseases, gender, diet, excretion, drugs used simultaneously or at different times in the corresponding individual, ingredients of other compositions, and the like and similar factors well known in the medical field. The effective dose may be easily determined and prescribed for desired treatment by those of ordinary skill in the art. The pharmaceutical composition of the present invention may be administered once or several times a day. Thus, the dose is not intended to limit the scope of the present invention in any way.
- The administration route and administration method of the pharmaceutical composition of the present invention may be independent of each other, the administration method is not particularly limited, and the administration route and the administration method may be an arbitrary administration route and administration route as long as they enable the pharmaceutical composition to reach the corresponding site. The pharmaceutical composition may be administered orally or parenterally.
- The parenteral administration may be, for example, intravenous administration, intraperitoneal administration, intramuscular administration, transdermal administration, subcutaneous administration, or the like, and the composition may be applied or sprayed on a disease site, or inhaled, but the present invention is not limited thereto.
- The pharmaceutical composition of the present invention may preferably be administered orally or via injection.
- The term “prevention” as used herein means all actions that inhibit or delay the onset of an oral disease via administration of the pharmaceutical composition of the present invention to an individual.
- The term “treatment” as used herein means all actions that alleviate or beneficially change symptoms of an oral disease via administration of the pharmaceutical composition of the present invention to an individual.
- In the present invention, the oral disease is a concept encompassing all diseases occurring in the oral cavity regardless of symptoms thereof, and may include, for example, oral diseases mainly caused by oral pathogenic microorganisms such as Streptococcus mutans, Porphyromonas gingivalis, Prevotella intermedia, Actinobacillus actinomycetemcomitans, and pathogenic microorganisms belonging to the genus Candida such as Candida albicans, and the like, or oral diseases caused by oral immunity degradation. Non-limiting examples of the oral disease include dental caries, gingivitis, periodontitis, oral mucous ulcers, halitosis, and xerostomia.
- The present invention also provides a method of preventing or treating an oral disease which includes administering the pharmaceutical composition for preventing or treating an oral disease to a subject.
- As used herein, the term “subject” includes all animals including mammals including mice, livestock, humans, and the like.
- In the method of preventing or treating an oral disease of the present invention, the description of dosage, administration route, administration method, and the like of the pharmaceutical composition is the same as described above in connection with the pharmaceutical composition of the present invention.
- The present invention also provides an oral hygiene composition for preventing or alleviating an oral disease, which includes one or more selected from the group consisting of agarobiose and agarooligosaccharides.
- In the present invention, the description of the agarobiose or agarooligosaccharides, the oral disease, and the prevention is the same as described above in connection with the pharmaceutical composition of the present invention.
- In the present invention, the oral hygiene composition includes all types and preparations that may be used for hygiene of the oral cavity. Non-limiting examples of the oral hygiene composition may include toothpastes, mouthwashes, oral sprays, oral ointments, and gum.
- The oral hygiene composition of the present invention may be formulated in the form of various preparations suitable for oral administration or parenteral administration to be used, and description related thereto is the same as described above in connection with the pharmaceutical composition of the present invention.
- The term “alleviation” as used herein means all actions that decrease at least the degree of parameters related to conditions being treated, e.g., symptoms.
- The present invention also provides a food composition for preventing or alleviating an oral disease, which includes one or more selected from the group consisting of agarobiose and agarooligosaccharides.
- Here, the description of the agarobiose or agarooligosaccharides, the oral disease, and the prevention, and the alleviation is the same as described above in connection with the pharmaceutical composition of the present invention.
- The food composition of the present invention is not particularly limited, and includes a health functional food composition.
- The term “health functional food” as used herein refers to a food prepared by adding the agarobiose or agarooligosaccharides to food substances such as beverages, teas, condiments, gum, confectionaries, or the like, or a food prepared in the form of capsules, powders, suspensions, or the like, and refers to a food that imparts a specific health effect when ingested.
- When the health functional food composition of the present invention is used as a food additive, the composition may be directly added or may be used in combination with other foods or food ingredients, and may be appropriately used according to a general method.
- The type of the food is not particularly limited, and includes all foods in a general sense. Non-limiting examples of foods to which the material is applicable include meat, sausages, bread, chocolates, candies, snacks, confectionaries, pizza, ramen, other noodles, gum, dairy products including ice creams, various soups, beverages, teas, drinks, alcoholic beverages, and vitamin complexes.
- When the health functional food composition of the present invention is a beverage composition, the beverage composition may include various flavor enhancers, natural carbohydrates, or the like as additional ingredients like general beverages. Non-limiting examples of the natural carbohydrates include monosaccharides such as glucose and fructose; disaccharides such as maltose and sucrose; natural sweeteners such as dextrin and cyclodextrin; and synthetic sweeteners such as saccharin and aspartame. A ratio of the added additional ingredients may be appropriately selected and determined by those of ordinary skill in the art.
- In addition, the health functional food composition of the present invention may include various nutrients, vitamins, electrolytes, a flavoring agent, a colorant, pectic acid and a salt thereof, alginic acid and a salt thereof, organic acids, a protective colloidal thickening agent, a pH adjusting agent, a stabilizer, a preservative, glycerin, alcohols, carbonating agents used in carbonated beverages, or the like. In addition, the health functional food composition of the present invention may include pulp for preparing natural fruit juices, fruit beverages, vegetable beverages, or the like. These ingredients may be used alone or a combination of two or more of these ingredients may be used. A ratio of these additives may also be appropriately selected by those of ordinary skill in the art.
- Hereinafter, the present invention will be described in further detail with reference to the following examples, but these examples are not intended to limit the scope of the present invention.
- Agarose was dissolved in 2% phosphoric acid at a concentration of 30.7% (w/v) and a reaction was allowed to occur therebetween using a microwave digester at 110° C. for 10 minutes, and then the acid-hydrolyzed reaction product was neutralized using 5 M NaOH such that the reaction product had a pH of 5 to 6. The reaction product was lyophilized to obtain powder-type agarooligosaccharides.
- 5% agarose was prepared using 200 mL of a 20 mM Tris-HCl buffer (pH 7.0) and dissolved in an autoclave at 121° C. for 10 minutes, and then 19.7 mg of Aga16B (see Korean Patent Application No. 2016-0006589) was added thereto in order to degrade the agarose, and a reaction was allowed to occur therein at 55° C. and 200 rpm for 12 hours, thereby obtaining neoagarotetraose and neoagarohexaose as reaction products. Each reaction product was allowed to react with 20 mg of Aga50D, which is an exo-type disaccharide-producing enzyme (see Korean Patent Application Publication No. 2010-0040438, published on Apr. 20, 2010) to decompose these reaction products, at 25° C. and 200 rpm, thereby obtaining neoagarobiose as a reaction product.
- To respectively separate and purify only agarobiose and neoagarobiose from the reaction products of Examples 1 and 2, Bio-gel P2 chromatography, which is gel permeation chromatography, was performed. Water was used as a mobile phase and a speed of the mobile phase was 0.1 mL/min. The volume of one fraction was 1 mL, and the sample consisting of a total of 100 fractions was analyzed through TLC, and then among these, only a fraction containing each of agarobiose and neoagarobiose was collected and lyophilized to thereby obtain powder-type agarobiose and powder-type neoagarobiose.
- The agarooligosaccharides obtained according to Example 1 were analyzed by HPLC. The used column was KS-802 (Shodex), and each sample was analyzed at a column temperature of 80° C. and a flow rate of 5 mL/min. The used mobile phase was water.
- As an analysis result, it was confirmed that the agarooligosaccharides of Example 1 mainly consisted of a mixture of oligosaccharides having degrees of polymerization of 2, 4, 6, and 8.
- In addition, the agarobiose and neoagarobiose with high purity, which were produced according to Example 3, were analyzed by HPLC and quantified. The column, column temperature, flow rate, and mobile phase used in the analysis were the same as those used in the analysis of the agarooligosaccharides, i.e., KS-802 (Shodex), 80° C., 0.5 mL/min, and water, respectively.
- A strain used in the present experiment was Streptococcus mutans ATCC 25175. Streptococcus mutans ATCC 25175 was pre-cultured in a brain-heart infusion (BHI) medium for 8 hours, and was washed twice with a 2 mM potassium phosphate buffer, and then main-cultured in a minimal medium prepared with reference to a previously reported document (Fujiwara et al (1978) Arch Oral Biol. 23, 601-602) at 37° C. The minimal medium contains, in a 50 mM Tris-HCl buffer (pH 7.4), 2 g/L of L-glutamic acid, 0.2 g/L of cysteine hydrochloride, 0.9 g/L of L-leucine, 1 g/L of ammonium chloride, 3.5 g/L of potassium hydrogen phosphate, 1.5 g/L of potassium dihydrogen phosphate, 4.2 g/L of sodium hydrogen carbonate, 1.2 g/L of magnesium sulfate heptahydrate, 0.02 g/L of manganese chloride tetrahydrate, 0.02 g/L of iron sulfate heptahydrate, 0.6 g/L of sodium pyruvate, 1 mg/L of riboflavin, 0.5 mg/L of thiamine hydrochloride, 0.1 mg/L of biotin, 1 mg/L of nicotinic acid, 0.1 mg/L of p-aminobenzoic acid, 0.5 mg/L of calcium pantothenate, and 1 mg/L of pyridoxine hydrochloride.
- To verify an effect of inhibiting the growth of Streptococcus mutans under a single carbon source condition, Streptococcus mutans were cultured in a minimal medium containing each of 10 g/L of agarobiose, agarooligosaccharides, glucose, xylitol, and neoagarobiose and a carbon source-free minimal medium. They were main-cultured using the method of Example 5 for 14 hours, and a degree of the cell growth was measured by measuring the absorbance of a culture solution at a wavelength of 600 nm every two hours.
- As a result, the absorbance at 600 nm was measured as 0.927 8 at hours after Streptococcus mutans entered a stationary phase under a glucose condition. However, no growth of Streptococcus mutans was observed under conditions excluding glucose, i.e., in the case of agarobiose, agarooligosaccharides, xylitol, or neoagarobiose. Thus, it was confirmed that agarobiose, agarooligosaccharides, and neoagarobiose are non-fermentable sugars for Streptococcus mutans like xylitol, and had an effect of inhibiting the growth of Streptococcus mutans (see
FIG. 1 ). - Streptococcus mutans was cultured, using the method of Example 5, in 200 μl of a minimal medium containing 10 g/L of glucose and agarobiose, agarooligosaccharides, xylitol, or neoagarobiose at various concentrations in a 96-well plate, and growth inhibitory effects thereof were observed by measuring absorbance at a wavelength of 600 nm over time. The treated concentrations of agarobiose, agarooligosaccharides, xylitol, and neoagarobiose were between 0 g/L and 20 g/L.
- The experimental results showed that there was no significant change in the growth of Streptococcus mutans under a condition of neoagarobiose up to a concentration of 20 g/L. In contrast, in the case of agarobiose, inhibition of the growth of Streptococcus mutans was observed at a concentration of 2.5 g/L to 20 g/L. It was also confirmed that the effect of agarobiose on inhibiting the growth of Streptococcus mutans increased as a concentration thereof became higher. Also, in the case of xylitol, the growth of Streptococcus mutans was inhibited at a concentration of 5 g/L to 20 g/L and the growth inhibitory effect significantly increased as a concentration of xylitol became higher. However, when final absorbance values were compared after 14 hours of culture, a lower absorbance value was obtained at the same concentration under a condition of agarobiose than under a condition of xylitol. Thus, it was confirmed that the effect of agarobiose on inhibiting the growth of Streptococcus mutans was greater than that of xylitol (see
FIG. 2 ). Agarooligosaccharides also inhibited the growth of Streptococcus mutans at a concentration of 5 g/L to 20 g/L. The final absorbance at 5 g/L of agarooligosaccharide was similar to that at 5 g/L of xylitol, but absorbance values at concentrations of 10 g/L and 20 g/L were found to be lower under the agarooligosaccharide condition than under the xylitol condition. From these results, it was confirmed that the effect of agarooligosaccharides on inhibiting the growth of Streptococcus mutans was greater than that of xylitol (seeFIG. 2 ). - To confirm an effect of agarobiose, agarooligosaccharides, xylitol, or neoagarobiose on acid production of Streptococcus mutans, Streptococcus mutans were cultured, using the method of Example 5, in 200 μl of a minimal medium containing 10 g/L of glucose and 0 g/L, 2.5 g/L, 5 g/L, 10 g/L, or 20 g/L of agarobiose, agarooligosaccharides, or neoagarobiose, or 0 g/L, 5 g/L, 10 g/L, or 20 g/L of xylitol in a 96-well plate. After 14 hours, concentrations of extracellular glucose and produced lactic acid were measured by HPLC. A column used for HPLC analysis was Aminex HPX-87H. 0.01 N of sulfuric acid as a mobile phase was flowed at a rate of 0.5 mL/min and 65° C.
- Under a condition of only glucose included as a carbon source, the absorbance value at 600 nm after 14 hours of culture was 0.927. At this time, glucose was consumed at 8.37 g/L, and the concentration of produced lactic acid was measured as 8.13 g/L (see
FIGS. 2, 3 , and 4). - Under a condition of including 2.5 g/L of agarobiose in 10 g/L of glucose, the absorbance value after 14 hours of culture was 0.55, and the concentrations of consumed glucose and produced lactic acid were 6.78 g/L and 5.65 g/L, respectively. These are decreases of 19% and 32%, respectively, compared to the case of not including agarobiose. From these results, it was confirmed that the growth of Streptococcus mutans was inhibited by agarobiose from a concentration of 2.5 g/L. In addition, under a condition of 10 g/L of agarobiose, the amounts of consumed glucose and produced lactic acid were 4.05 g/L and 3.25 g/L, respectively, which correspond to decreases of 51.5% and 60%, respectively, as compared to a condition of 0 g/L of agarobiose. In addition, the amounts of consumed glucose and produced lactic acid under a condition of 20 g/L of agarobiose were reduced 58.76% and 68%, respectively, from which it was confirmed that the degree of acid production of Streptococcus mutans was gradually reduced as the concentration of agarobiose increased (see
FIGS. 2, 3, and 4 ). - The amounts of consumed glucose and produced lactic acid after culturing for 14 hours under a condition of including 2.5 g/L or 5 g/L of agarooligosaccharides in 10 g/L of glucose did not show significant differences compared to an agarooligosaccharides-free condition. However, the amounts of consumed glucose and produced lactic acid under a condition of including 10 g/L of agarooligosaccharides were 5.63 g/L and 5.4 g/L, respectively, which correspond to decreases of 32% and 33.55%, respectively, as compared to an agarooligosaccharides-free condition. It was also confirmed that the amounts of consumed glucose and produced lactic acid under a condition of 20 g/L of agarooligosaccharides were reduced 44% and 47.7%, respectively (see
FIGS. 3 and 4 ). - As a control, xylitol was added to 10 g/L of glucose at various concentrations. The amount of reduced lactic acid under a condition of including 5 g/L of xylitol was 30%, which was lower than that under a condition of 2.5 g/L of agarobiose, i.e., 32%. The absorbance value at 600 nm after culturing for 14 hours under a condition of adding 20 g/L of xylitol was found to be 0.595, which was higher than a condition of the same concentration of agarobiose. In addition, the amounts of consumed glucose and produced lactic acid were reduced 36.41% and 35%, respectively. From these results, it was confirmed that these were lower than those under a condition of the same concentration of agarobiose. When conditions of xylitol and agarooligosaccharides were compared, a decrease in the amount of consumed glucose under a condition of 10 g/L of agarooligosaccharides was 32%, which was higher than that under a condition of the same concentration of xylitol, i.e., 23.98%. At this time, a decrease in the amount of produced lactic acid under a condition of agarooligosaccharides was 33.55%, which was similar to that under a condition of xylitol, i.e., 35%. However, the amounts of consumed glucose and produced lactic acid under a condition of 20 g/L of agarooligosaccharide were reduced 44% and 47.7%, respectively, which correspond to greater decreases than those under a condition of xylitol, i.e., 36.41% and 35% (see
FIGS. 2, 3, and 4 ). - As in the case of agarobiose, neoagarobiose, which is a red algae-derived disaccharide, was added to 10 g/L of glucose at various concentrations and comparison was performed after culturing. As a result, it was confirmed that neoagarobiose did not exhibit significant differences in a final absorbance value, the amount of consumed glucose, and the amount of produced lactic acid up to a concentration of 20 g/L, as compared to the case of 0 g/L (see
FIGS. 3 and 4 ). - From these results, it was confirmed that xylitol known as a sugar that prevents dental caries was unable to inhibit the growth and acid production of Streptococcus mutans as much as agarobiose at the same concentration. It was also confirmed that the degrees of inhibition of the growth and acid production of Streptococcus mutans under a condition of 5 g/L of agarobiose were greater than those under a condition of 10 g/L of xylitol. This indicates that the effect of agarobiose on inhibiting the growth and acid production of Streptococcus mutans is stronger at a lower concentration than that of xylitol. It was also confirmed that the effect of agarooligosaccharides on inhibiting the growth of Streptococcus mutans was similar to or stronger than that of xylitol at the same concentration. In contrast, neoagarobiose, which is a red algae-derived disaccharide like agarobiose, was unable to inhibit the growth and acid production of Streptococcus mutans. This indicates that, among red algae-derived disaccharides, only agarobiose has an effect of inhibiting the growth and acid production of Streptococcus mutans.
- The present invention can be applied to the development field of oral hygiene products such as toothpastes, mouthwashes, oral sprays, and the like, foods such as gum, candies, and the like, and medicines.
Claims (12)
1. A pharmaceutical composition for preventing or treating an oral disease, comprising one or more selected from the group consisting of agarobiose and agarooligosaccharides,
wherein the oral disease is any one selected from the group consisting of dental caries, gingivitis, periodontitis, oral mucous ulcers, halitosis, and xerostomia.
2. The pharmaceutical composition of claim 1 , wherein the agarooligosaccharides are obtained from an acid hydrolysate of agarose.
3. The pharmaceutical composition of claim 1 , wherein the agarooligosaccharides are a mixture of agarobiose, agarotetraose, agarohexaose, and agarooctaose.
4. The pharmaceutical composition of claim 1 , wherein the agarobiose is obtained by separating and purifying an acid hydrolysate of agarose through gel permeation chromatography.
5. An oral hygiene composition for preventing or alleviating an oral disease, comprising one or more selected from the group consisting of agarobiose and agarooligosaccharides,
wherein the oral disease is any one selected from the group consisting of dental caries, gingivitis, periodontitis, oral mucous ulcers, halitosis, and xerostomia.
6. The oral hygiene composition of claim 5 , wherein the agarooligosaccharides are obtained from an acid hydrolysate of agarose.
7. The oral hygiene composition of claim 5 , wherein the agarooligosaccharides are a mixture of agarobiose, agarotetraose, agarohexaose, and agarooctaose.
8. The oral hygiene composition of claim 5 , wherein the agarobiose is obtained by separating and purifying an acid hydrolysate of agarose through gel permeation chromatography.
9. A food composition for preventing or alleviating an oral disease, comprising one or more selected from the group consisting of agarobiose and agarooligosaccharides,
wherein the oral disease is any one selected from the group consisting of dental caries, gingivitis, periodontitis, oral mucous ulcers, halitosis, and xerostomia.
10. The food composition of claim 9 , wherein the agarooligosaccharides are obtained from an acid hydrolysate of agarose.
11. The food composition of claim 9 , wherein the agarooligosaccharides are a mixture of agarobiose, agarotetraose, agarohexaose, and agarooctaose.
12. The food composition of claim 9 , wherein the agarobiose is obtained by separating and purifying an acid hydrolysate of agarose through gel permeation chromatography.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2016-0152163 | 2016-11-15 | ||
KR20160152163 | 2016-11-15 | ||
KR10-2017-0015459 | 2017-02-03 | ||
KR1020170015459A KR101960503B1 (en) | 2016-11-15 | 2017-02-03 | Use of agarobiose or agarooligosaccharides having anticariogenic activity |
PCT/KR2017/012914 WO2018093129A1 (en) | 2016-11-15 | 2017-11-15 | Use of agarobiose or agarooligosaccharide having anticariogenic activity |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2017/012914 A-371-Of-International WO2018093129A1 (en) | 2016-11-15 | 2017-11-15 | Use of agarobiose or agarooligosaccharide having anticariogenic activity |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/985,850 Division US11458152B2 (en) | 2016-11-15 | 2020-08-05 | Use of agarobiose or agarooligosaccharide having anticariogenic activity |
Publications (1)
Publication Number | Publication Date |
---|---|
US20200078383A1 true US20200078383A1 (en) | 2020-03-12 |
Family
ID=62299551
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/349,885 Abandoned US20200078383A1 (en) | 2016-11-15 | 2017-11-15 | Use of agarobiose or agarooligosaccharide having anticariogenic activity |
US16/985,850 Active 2038-03-30 US11458152B2 (en) | 2016-11-15 | 2020-08-05 | Use of agarobiose or agarooligosaccharide having anticariogenic activity |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US16/985,850 Active 2038-03-30 US11458152B2 (en) | 2016-11-15 | 2020-08-05 | Use of agarobiose or agarooligosaccharide having anticariogenic activity |
Country Status (3)
Country | Link |
---|---|
US (2) | US20200078383A1 (en) |
KR (1) | KR101960503B1 (en) |
CN (1) | CN110177540B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4340949A1 (en) | 2021-05-20 | 2024-03-27 | Smile Makers, LLC | Oral hygiene compositions and methods of use |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070202238A1 (en) * | 1999-05-14 | 2007-08-30 | Takara Bio Inc. | Agarobiose-containing composition |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0570252A3 (en) | 1992-05-15 | 1994-02-23 | Ina Food Ind Co Ltd | Low gel strength agar-agar |
US6475990B1 (en) * | 1997-11-11 | 2002-11-05 | Takara Shuzo Co., Ltd. | Drugs, foods or drinks with the use of algae-derived physiologically active substances |
KR20010018802A (en) * | 1999-08-23 | 2001-03-15 | 윤의구 | The manufacturing method of a oligosaccharide |
JP2002029952A (en) * | 2000-05-11 | 2002-01-29 | Takayuki Kodama | Composition for dentifrice |
JP6270113B2 (en) | 2012-11-19 | 2018-01-31 | 児玉 剛之 | Oral composition |
KR20180046021A (en) * | 2016-10-27 | 2018-05-08 | 다인바이오 주식회사 | Composition including neoagarooligosaccharide for preventing, improving or treating inflammatory disease |
-
2017
- 2017-02-03 KR KR1020170015459A patent/KR101960503B1/en active IP Right Grant
- 2017-11-15 US US16/349,885 patent/US20200078383A1/en not_active Abandoned
- 2017-11-15 CN CN201780083294.0A patent/CN110177540B/en active Active
-
2020
- 2020-08-05 US US16/985,850 patent/US11458152B2/en active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070202238A1 (en) * | 1999-05-14 | 2007-08-30 | Takara Bio Inc. | Agarobiose-containing composition |
Also Published As
Publication number | Publication date |
---|---|
CN110177540A (en) | 2019-08-27 |
CN110177540B (en) | 2023-02-17 |
KR101960503B1 (en) | 2019-03-21 |
KR20180055628A (en) | 2018-05-25 |
US11458152B2 (en) | 2022-10-04 |
US20200376012A1 (en) | 2020-12-03 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8496915B2 (en) | Noncarious material and anticarious agent containing rare sugar | |
US7214667B2 (en) | Drugs against articular failure | |
JP2926412B2 (en) | α-Glycosyl-L-ascorbic acid, its production method and use | |
KR0158454B1 (en) | Preparation of alpha glycosyl rutin | |
US11453694B2 (en) | Glycosyl hesperetin and process for producing the same and uses thereof | |
US20100113390A1 (en) | Oligosaccharides derived from fucoidan | |
EP1679071A1 (en) | Collagen productin enhancer and production process and use thereof | |
KR0156539B1 (en) | 4go-alpha-d-glucopyranosyl rutin, and its preparation and uses | |
US11458152B2 (en) | Use of agarobiose or agarooligosaccharide having anticariogenic activity | |
KR101419464B1 (en) | The composition comprising the extract or fraction of Pleurotus eryngii var. ferulae for prevention of anti aging as an active ingredient | |
US10548828B2 (en) | Use of 3,6-anhydro-L-galactose for preventing dental caries | |
KR20200029187A (en) | Composition with antibacterial effect on oral bacteria containing coffee extract, prebiotic, or coffee extract and prebiotic | |
JPS6251584B2 (en) | ||
KR102297957B1 (en) | A composition for improving, preventing and treating of acne and atopic dermatitis comprising black garlic extract | |
WO2018093129A1 (en) | Use of agarobiose or agarooligosaccharide having anticariogenic activity | |
KR101613964B1 (en) | Compositions for prevention or treatment of Helicobacter pylori infection comprising enzyme hydrolysate of glycomacropeptide as active ingredient | |
KR101749687B1 (en) | Antibacterial agent comprising 7,10-epoxy-octadeca-7,9-dienoic acid | |
JP2000297040A (en) | Anticariogenic composition and food and beverage | |
KR20190033441A (en) | Composition with antibacterial effect on oral bacteria containing Rubusoside | |
JPS61181354A (en) | Food and drink | |
Embuscado et al. | Cerestar USA, Inc., Hammond, Indiana | |
KR20160006886A (en) | Compositions for prevention or treatment of Helicobacter pylori infection comprising cytidylic acid, adenylic acid or its salt as active ingredient |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: KOREA UNIVERSITY RESEARCH AND BUSINESS FOUNDATION, KOREA, REPUBLIC OF Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KIM, KYOUNG HEON;YUN, EUN-JU;YU, SORA;AND OTHERS;REEL/FRAME:049183/0790 Effective date: 20190411 |
|
STCB | Information on status: application discontinuation |
Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION |