KR102441302B1 - Composition for anti-cancer containing deacetyl torilin as effective component - Google Patents
Composition for anti-cancer containing deacetyl torilin as effective component Download PDFInfo
- Publication number
- KR102441302B1 KR102441302B1 KR1020200017809A KR20200017809A KR102441302B1 KR 102441302 B1 KR102441302 B1 KR 102441302B1 KR 1020200017809 A KR1020200017809 A KR 1020200017809A KR 20200017809 A KR20200017809 A KR 20200017809A KR 102441302 B1 KR102441302 B1 KR 102441302B1
- Authority
- KR
- South Korea
- Prior art keywords
- cancer
- diacetyl
- anticancer
- torillin
- formula
- Prior art date
Links
- 230000001093 anti-cancer Effects 0.000 title claims abstract description 19
- 239000000203 mixture Substances 0.000 title claims description 22
- ZKFDRXXLYBOAKO-UHFFFAOYSA-N Desacetyl-torilin Natural products CC=C(C)/C(=O)OC1CC(C)C2CC(=O)C(=C2CC1C(=C)C)C ZKFDRXXLYBOAKO-UHFFFAOYSA-N 0.000 title 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000004480 active ingredient Substances 0.000 claims abstract description 17
- 230000036541 health Effects 0.000 claims abstract description 14
- 235000013376 functional food Nutrition 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- 206010006187 Breast cancer Diseases 0.000 claims description 6
- 208000026310 Breast neoplasm Diseases 0.000 claims description 6
- 206010009944 Colon cancer Diseases 0.000 claims description 6
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
- 239000000796 flavoring agent Substances 0.000 claims description 6
- 235000013355 food flavoring agent Nutrition 0.000 claims description 6
- 206010017758 gastric cancer Diseases 0.000 claims description 6
- 201000007270 liver cancer Diseases 0.000 claims description 6
- 208000014018 liver neoplasm Diseases 0.000 claims description 6
- 201000005202 lung cancer Diseases 0.000 claims description 6
- 208000020816 lung neoplasm Diseases 0.000 claims description 6
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
- 201000002528 pancreatic cancer Diseases 0.000 claims description 6
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
- 201000011549 stomach cancer Diseases 0.000 claims description 6
- -1 diacetyl torilin Chemical compound 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 239000003755 preservative agent Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229920002230 Pectic acid Polymers 0.000 claims description 2
- 239000000783 alginic acid Substances 0.000 claims description 2
- 235000010443 alginic acid Nutrition 0.000 claims description 2
- 229920000615 alginic acid Polymers 0.000 claims description 2
- 229960001126 alginic acid Drugs 0.000 claims description 2
- 150000004781 alginic acids Chemical class 0.000 claims description 2
- 235000014171 carbonated beverage Nutrition 0.000 claims description 2
- 239000003086 colorant Substances 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 239000003623 enhancer Substances 0.000 claims description 2
- 235000015097 nutrients Nutrition 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 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 claims description 2
- 239000010318 polygalacturonic acid Substances 0.000 claims description 2
- 230000001681 protective effect Effects 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- IQWVFAXBJQKUDH-HJYBKFAWSA-N torilin Natural products O=C(O[C@H]1[C@@H](C(OC(=O)C)(C)C)CC2=C(C)C(=O)C[C@@H]2[C@@H](C)C1)/C(=C/C)/C IQWVFAXBJQKUDH-HJYBKFAWSA-N 0.000 claims description 2
- 235000013343 vitamin Nutrition 0.000 claims description 2
- 229930003231 vitamin Natural products 0.000 claims description 2
- 239000011782 vitamin Substances 0.000 claims description 2
- 229940088594 vitamin Drugs 0.000 claims description 2
- 235000013334 alcoholic beverage Nutrition 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 15
- 201000011510 cancer Diseases 0.000 abstract description 14
- 239000002246 antineoplastic agent Substances 0.000 abstract description 8
- 229940041181 antineoplastic drug Drugs 0.000 abstract description 5
- 230000004083 survival effect Effects 0.000 abstract description 3
- 230000003833 cell viability Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000003814 drug Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000013361 beverage Nutrition 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002044 hexane fraction Substances 0.000 description 3
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 3
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 101710088194 Dehydrogenase Proteins 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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 2
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 229930006000 Sucrose Natural products 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 235000014633 carbohydrates Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 210000004209 hair Anatomy 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000008101 lactose 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
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- HELXLJCILKEWJH-NCGAPWICSA-N rebaudioside A Chemical compound O([C@H]1[C@H](O)[C@@H](CO)O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@]12C(=C)C[C@@]3(C1)CC[C@@H]1[C@@](C)(CCC[C@]1([C@@H]3CC2)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O HELXLJCILKEWJH-NCGAPWICSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- 201000004384 Alopecia Diseases 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
- 241000208173 Apiaceae Species 0.000 description 1
- 108010011485 Aspartame Proteins 0.000 description 1
- ZLDODTPRRLQGHP-LGYCOIBBSA-N C[C@H]1C[C@@H](O)[C@@H](C(C)(C)O)CC2=C(C)C(=O)C[C@H]12 Chemical compound C[C@H]1C[C@@H](O)[C@@H](C(C)(C)O)CC2=C(C)C(=O)C[C@H]12 ZLDODTPRRLQGHP-LGYCOIBBSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 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
- 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
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012434 Dermatitis allergic Diseases 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 239000001512 FEMA 4601 Substances 0.000 description 1
- 208000002633 Febrile Neutropenia Diseases 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
- 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 1
- 239000004378 Glycyrrhizin Substances 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
- 206010028813 Nausea Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- HELXLJCILKEWJH-SEAGSNCFSA-N Rebaudioside A Natural products O=C(O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@]1(C)[C@@H]2[C@](C)([C@H]3[C@@]4(CC(=C)[C@@](O[C@H]5[C@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O6)[C@H](O)[C@@H](CO)O5)(C4)CC3)CC2)CCC1 HELXLJCILKEWJH-SEAGSNCFSA-N 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 244000228451 Stevia rebaudiana Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 240000003803 Torilis japonica Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- IQWVFAXBJQKUDH-TXCQZRSTSA-N [(5s,6r,8s,8ar)-5-(2-acetyloxypropan-2-yl)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1h-azulen-6-yl] (z)-2-methylbut-2-enoate Chemical compound C1[C@H](C(C)(C)OC(C)=O)[C@H](OC(=O)C(\C)=C/C)C[C@H](C)[C@H]2CC(=O)C(C)=C21 IQWVFAXBJQKUDH-TXCQZRSTSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent 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
- 238000003556 assay Methods 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 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 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 235000011869 dried fruits Nutrition 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- HELXLJCILKEWJH-UHFFFAOYSA-N entered according to Sigma 01432 Natural products C1CC2C3(C)CCCC(C)(C(=O)OC4C(C(O)C(O)C(CO)O4)O)C3CCC2(C2)CC(=C)C21OC(C1OC2C(C(O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OC(CO)C(O)C(O)C1O HELXLJCILKEWJH-UHFFFAOYSA-N 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 150000002148 esters Chemical class 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
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N lauric acid triglyceride Natural products CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229960003511 macrogol Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- 230000005787 mitochondrial ATP synthesis coupled electron transport Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940124595 oriental medicine Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 235000019203 rebaudioside A Nutrition 0.000 description 1
- 235000009566 rice Nutrition 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
- 235000002020 sage 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
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- JUJBNYBVVQSIOU-UHFFFAOYSA-M sodium;4-[2-(4-iodophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].C1=CC([N+](=O)[O-])=CC=C1N1[N+](C=2C=CC(I)=CC=2)=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=N1 JUJBNYBVVQSIOU-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000003265 stomatitis Diseases 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 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
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- ZLDODTPRRLQGHP-UHFFFAOYSA-N torilolone Natural products CC1CC(O)C(C(C)(C)O)CC2=C(C)C(=O)CC12 ZLDODTPRRLQGHP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- A23V2200/308—Foods, ingredients or supplements having a functional effect on health having an effect on cancer prevention
-
- 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
- A23V2250/30—Other Organic compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Botany (AREA)
- Engineering & Computer Science (AREA)
- Mycology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Emergency Medicine (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
본 발명은 사상자로부터 분리한 디아세틸 토릴린 및 이를 유효성분으로 포함하는 항암용 약학 조성물에 관한 것으로, 본 발명의 디아세틸 토릴린은 다양한 종류의 암세포 생존율을 감소시키는 효과가 있는 것이다. 따라서 본 발명에 따른 디아세틸 토릴린은 항암용 의약품 또는 건강기능식품 산업에 유용하게 사용될 수 있다.The present invention relates to diacetyl torillin isolated from the dead and to an anticancer pharmaceutical composition comprising the same as an active ingredient, and the diacetyl torillin of the present invention is effective in reducing the survival rate of various types of cancer cells. Therefore, diacetyl torillin according to the present invention can be usefully used in anticancer drugs or health functional food industries.
Description
본 발명은 디아세틸 토릴린을 유효성분으로 포함하는 항암용 조성물에 관한 것이다.The present invention relates to an anticancer composition comprising diacetyl torillin as an active ingredient.
수십 년간의 노력에도 암은 아직까지 질병에 의한 현대인의 사망원인 중 1~2위를 차지하고 있다. 이와 같은 암은 정상세포가 발암물질이나 바이러스 등이 원인이 되어 유전 변이를 일으켜 발생하는 것으로, 항암제 개발과 치료는 정상세포에서는 발현되지 않고 암세포에서만 특이적으로 발현되는 유전자나 단백질을 표적으로 개발되어 왔다. 항암제는 단독 또는 방사능 요법 등의 다른 치료법과 병행하여 암을 치료하는 가장 일반적이며 효율적인 치료 방법이다. 이러한 항암제에 의한 암의 치료는 암세포를 사멸시킬 수 있는 능력에 기인하는데, 암세포뿐만 아니라 정상세포도 사멸시켜 빈번하게 탈모, 식욕부진, 오심, 구토, 호흡곤란, 구내염, 호중구 감소성 발열 등의 부작용을 유발한다는 것이다. 환자의 일반적인 건강 상태에 따라 이와 같은 부작용은 항암제 치료를 불가능하게 하거나 적어도 환자에게 극도의 불쾌감과 불편함을 줄 수 있으며, 암 환자의 삶의 질을 심각하게 훼손시킬 수 있다.Despite decades of efforts, cancer still ranks first or second among the causes of death among modern people due to disease. Such cancers are caused by genetic mutations caused by carcinogens or viruses in normal cells. The development and treatment of anticancer drugs target genes or proteins that are not expressed in normal cells but are specifically expressed in cancer cells. come. Anticancer agents are the most common and effective treatment methods for cancer treatment alone or in combination with other therapies such as radiotherapy. The treatment of cancer with these anticancer drugs is due to the ability to kill cancer cells, and it kills not only cancer cells but also normal cells, which frequently causes side effects such as hair loss, anorexia, nausea, vomiting, dyspnea, stomatitis, neutropenic fever, etc. that it causes Depending on the patient's general health, such side effects may make anticancer drug treatment impossible, or at least give the patient extreme discomfort and discomfort, and may seriously impair the quality of life of cancer patients.
한편, 사상자(Torilidis Fructus)는 미나리과(Umbelliferae)의 두해살이풀인 사상자(Torilis japonica (Houtt.) DC.)의 열매로 맵고 쓰며 따뜻한 성질이 있고 독이 없다고 알려져 있다. 우리말로는 '뱀도랏'이라고도 한다. 도랑가 혹은 습지에 주로 자생하는데, 뱀이 사상자 풀 속에 숨어 그 씨는 즐겨 먹기에 사상자라는 이름이 붙였다고 한다. 높이 30~70cm이며 전체에 털이 분포한다. 잎은 2회 깃꼴겹잎이며, 길이 5~10cm로 끝이 뾰족하고 잎자루 끝은 원줄기를 감싼다. 열매는 길이 4~6mm로 볍씨처럼 생겼으며 겉에 가시털이 밀생한다.On the other hand, the sage ( Torilidis Fructus ) is the fruit of the biennial plant of the Umbelliferae ( Torilis japonica (Houtt.) DC. ), which is known to have hot, bitter, warm properties and no poison. In Korean, it is also called 'Bamdorat'. It grows mainly in ditches or wetlands, but it is said that the snake hides in the grass of the casualties and the seeds are often eaten, hence the name “death”. It is 30-70cm high and has hairs all over it. The leaves are pinnate compound leaves twice, with a length of 5-10cm, with a sharp tip, and the tip of the petiole wraps around the main stem. The fruit is 4~6mm long, looks like rice seed, and has dense thorn hairs on the outside.
한방에서는 열매를 말려 만든 생약을 사상자라 부르며, 약리 효과로 항원충작용, 성호르몬 유사작용 등이 있고, 여성 등의 자궁냉증 치료와 인플루엔자 바이러스와 트리코모나스균의 활동을 억제하여 피부소양증에도 효과가 있어 소염제 또는 가려움증을 없애는 연고로 쓰인다. 또한, 사상자는 피부질환에 대해서도 치료효과가 있으므로 피부습진, 알레르기성 피부염에도 사용된다. 사상자의 주요성분은 토릴린(torilin), 토릴로론(torilolone) 등의 세스퀴테르펜(sesquiterpene)계 화합물이 함유되어 있는 것으로 보고되고 있다. In oriental medicine, a herbal medicine made from dried fruits is called saengjae, and its pharmacological effects include antiparasitic action and sex hormone-like action. It is used as an anti-inflammatory or ointment to relieve itching. In addition, the casualty is also used for skin eczema and allergic dermatitis because it has a therapeutic effect on skin diseases. It is reported that the main component of the casualties contains sesquiterpene compounds such as torilin and torilolone.
한편, 한국등록특허 제0159642호에 토릴린을 함유하는 항암제 활성 증강용 조성물이 개시되어 있고, 한국등록특허 제1484709호에 벌사상자 추출물을 유효성분으로 함유하는 면역증강 및 암질환 치료 또는 예방용 조성물이 개시되어 있으며, 한국등록특허 제1485318호에 사상자 추출물을 유효성분으로 함유하는 암 예방 또는 개선용 식품 조성물 및 약학 조성물이 개시되어 있으나, 본 발명의 디아세틸 토릴린을 유효성분으로 포함하는 항암용 조성물에 대해 개시된 바 없다. On the other hand, Korean Patent No. 0159642 discloses a composition for enhancing anticancer drug activity containing torillin, and Korean Patent No. 1484709 discloses a composition for immune enhancement and cancer disease treatment or prevention containing an extract of bee sasanqua extract as an active ingredient. This is disclosed, and Korea Patent No. 1485318 discloses a food composition and pharmaceutical composition for preventing or ameliorating cancer containing an extract of the common death cause as an active ingredient. No composition has been disclosed.
본 발명은 상기와 같은 요구에 의해 도출된 것으로서, 본 발명은 디아세틸 토릴린을 유효성분으로 포함하는 항암용 조성물을 제공하고, 본 발명의 디아세틸 토릴린이 다양한 종류의 암세포 생존율을 감소시키는 것을 확인함으로써, 본 발명을 완성하였다.The present invention has been derived from the above needs, and the present invention provides an anticancer composition comprising diacetyl torylin as an active ingredient, and it is confirmed that diacetyl torylin of the present invention reduces the survival rate of various types of cancer cells Thus, the present invention was completed.
상기 목적을 달성하기 위하여, 본 발명은 화학식 1의 디아세틸 토릴린 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 항암용 약학 조성물을 제공한다.In order to achieve the above object, the present invention provides a pharmaceutical composition for anticancer comprising diacetyl torillin of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
또한, 본 발명은 화학식 1의 디아세틸 토릴린 또는 이의 식품학적으로 허용 가능한 염을 유효성분으로 포함하는 항암용 건강기능식품 조성물을 제공한다.In addition, the present invention provides a health functional food composition for anticancer comprising diacetyl torillin of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
본 발명은 디아세틸 토릴린을 유효성분으로 포함하는 항암용 조성물에 관한 것으로, 본 발명의 디아세틸 토릴린은 다양한 종류의 암세포 생존율을 감소시키는 효과가 있는 것이다.The present invention relates to an anticancer composition comprising diacetyl torillin as an active ingredient, and the diacetyl torillin of the present invention has an effect of reducing the survival rate of various types of cancer cells.
도 1은 디아세틸 토릴린(Tr-10)의 농도별 처리에 따른 폐암 세포주(A549)의 세포 생존율을 나타낸 것이다.
도 2는 디아세틸 토릴린(Tr-10)의 농도별 처리에 따른 위암 세포주(AGS)의 세포 생존율을 나타낸 것이다.
도 3은 디아세틸 토릴린(Tr-10)의 농도별 처리에 따른 유방암 세포주(MDA-MB-231)의 세포 생존율을 나타낸 것이다.
도 4는 디아세틸 토릴린(Tr-10)의 농도별 처리에 따른 간암 세포주(Hep3B)의 세포 생존율을 나타낸 것이다.
도 5는 디아세틸 토릴린(Tr-10)의 농도별 처리에 따른 대장암 세포주(HCT116)의 세포 생존율을 나타낸 것이다.
도 6은 디아세틸 토릴린(Tr-10)의 농도별 처리에 따른 췌장암 세포주(BxPC3)의 세포 생존율을 나타낸 것이다. Figure 1 shows the cell viability of the lung cancer cell line (A549) according to the treatment by concentration of diacetyl torillin (Tr-10).
Figure 2 shows the cell viability of the gastric cancer cell line (AGS) according to the treatment by concentration of diacetyl torillin (Tr-10).
Figure 3 shows the cell viability of the breast cancer cell line (MDA-MB-231) according to the treatment by concentration of diacetyl torillin (Tr-10).
Figure 4 shows the cell viability of the liver cancer cell line (Hep3B) according to the treatment according to the concentration of diacetyl torillin (Tr-10).
Figure 5 shows the cell viability of colorectal cancer cell line (HCT116) according to the treatment by concentration of diacetyl torillin (Tr-10).
Figure 6 shows the cell viability of the pancreatic cancer cell line (BxPC3) according to the treatment by concentration of diacetyl torillin (Tr-10).
본 발명은 화학식 1의 디아세틸 토릴린 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 항암용 약학 조성물에 관한 것이다.The present invention relates to a pharmaceutical composition for anticancer comprising diacetyl torillin of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
상기 화학식 1의 디아세틸 토릴린은 사상자로부터 분리한 것이 바람직하지만 이에 한정하지 않으며, 사상자 이외의 천연물로부터 분리할 수도 있고, 유기합성방법으로 합성할 수도 있다.Diacetyl torillin of Formula 1 is preferably isolated from casualties, but is not limited thereto, and may be isolated from natural products other than casualties or synthesized by organic synthesis.
상기 항암은 폐암, 위암, 간암, 유방암, 대장암 및 췌장암 중에서 선택된 어느 하나의 암에 대한 항암인 것이 바람직하지만 이에 한정하지 않는다.The anticancer agent is preferably an anticancer agent for any one cancer selected from lung cancer, stomach cancer, liver cancer, breast cancer, colorectal cancer and pancreatic cancer, but is not limited thereto.
본 발명의 약학 조성물은 경구 또는 비경구의 여러 가지 제형일 수 있다. 상기 조성물을 제제화할 경우에는 통상적으로 사용하는 담체, 부형제 또는 희석제를 사용하여 조제할 수 있으나 이에 한정하는 것은 아니다.The pharmaceutical composition of the present invention may be in various oral or parenteral formulations. When formulating the composition, it may be prepared using a carrier, excipient or diluent commonly used, but is not limited thereto.
경구투여를 위한 고형 제제에는 정제, 환제, 산제, 과립제, 캡슐제 등이 포함되며, 이러한 고형 제제는 하나 이상의 화합물에 적어도 하나 이상의 부형제 예를 들면, 전분, 탄산칼슘, 수크로오스(sucrose) 또는 락토오스(lactose), 젤라틴 등을 섞어 조제된다. 또한, 단순한 부형제 이외에 스테아린산 마그네슘, 탈크 등과 같은 윤활제들도 사용된다. 경구투여를 위한 액상 제제로는 현탁제, 내용액제, 유제 또는 시럽제 등이 해당되는데, 흔히 사용되는 단순 희석제인 물, 리퀴드 파라핀 이외에 여러 가지 부형제, 예를 들면 습윤제, 감미제, 방향제 또는 보존제 등이 포함될 수 있다. Solid preparations for oral administration include tablets, pills, powders, granules, capsules, etc., and such solid preparations include at least one excipient in one or more compounds, for example, starch, calcium carbonate, sucrose or lactose ( lactose), gelatin, etc. In addition to simple excipients, lubricants such as magnesium stearate and talc are also used. Liquid formulations for oral administration include suspensions, solutions, emulsions, or syrups. In addition to commonly used simple diluents such as water and liquid paraffin, various excipients, for example, wetting agents, sweeteners, fragrances or preservatives may be included. can
비경구 투여를 위한 제제에는 멸균된 수용액, 비수성용제, 현탁용제, 유제, 동결건조제제 또는 좌제 등이 포함된다. 비수성용제 및 현탁용제로는 프로필렌글리콜(propylene glycol), 폴리에틸렌 글리콜, 올리브 오일과 같은 식물성 기름, 에틸올레이트와 같은 주사 가능한 에스테르 등이 사용될 수 있다. 좌제의 기제(base)로는 위텝솔(witepsol), 마크로골, 트윈(tween) 61, 카카오지, 라우린지, 글리세롤, 젤라틴 등이 사용될 수 있다.Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solutions, suspension solutions, emulsions, lyophilized formulations, or suppositories. Non-aqueous solvents and suspensions may include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate. As the base of the suppository, witepsol, macrogol, tween 61, cacao butter, laurin fat, glycerol, gelatin, etc. may be used.
본 발명의 약학 조성물은 경구 또는 비경구로 투여될 수 있으며, 비경구 투여시 피부 외용 또는 복강 내, 직장, 정맥, 근육, 피하, 자궁 내 경막 또는 뇌혈관 내 주사 방식을 선택하는 것이 바람직하지만 이에 제한하지 않는다.The pharmaceutical composition of the present invention may be administered orally or parenterally, and when administered parenterally, it is preferable to select an external skin or intraperitoneal, rectal, intravenous, muscle, subcutaneous, intrauterine dural or intracerebrovascular injection method, but limited thereto. I never do that.
본 발명의 약학 조성물은 약학적으로 유효한 양으로 투여한다. 본 발명에 있어서, 약학적으로 유효한 양은 의학적 치료에 적용 가능한 합리적인 수혜/위험 비율로 질환을 치료하기에 충분한 양을 의미하며, 유효용량 수준은 환자의 질환의 종류, 중증도, 약물의 활성, 약물에 대한 민감도, 투여 시간, 투여 경로 및 배출 비율, 치료기간, 동시 사용되는 약물을 포함한 요소 및 기타 의학 분야에 잘 알려진 요소에 따라 결정될 수 있다. 본 발명의 조성물은 개별 치료제로 투여하거나 다른 치료제와 병용하여 투여될 수 있고 종래의 치료제와는 순차적 또는 동시에 투여될 수 있으며, 단일 또는 다중 투여될 수 있다. 상기한 요소들을 모두 고려하여 부작용 없이 최소한의 양으로 최대 효과를 얻을 수 있는 양을 투여하는 것이 중요하며, 이는 당업자에 의해 용이하게 결정될 수 있다.The pharmaceutical composition of the present invention is administered in a pharmaceutically effective amount. In the present invention, a pharmaceutically effective amount means an amount sufficient to treat a disease at a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level depends on the type, severity, drug activity, and drug of the patient. Sensitivity, administration time, administration route and excretion rate, treatment duration, factors including concurrent drugs, and other factors well known in the medical field may be determined. The composition of the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, may be administered sequentially or simultaneously with conventional therapeutic agents, and may be administered single or multiple. In consideration of all of the above factors, it is important to administer an amount that can obtain the maximum effect with a minimum amount without side effects, which can be easily determined by those skilled in the art.
본 발명의 조성물의 투여량은 환자의 체중, 연령, 성별, 건강상태, 식이, 투여시간, 투여방법, 배설률 및 질환의 중증도에 따라 그 범위가 다양하게 투여될 수 있으나, 투여 경로, 비만의 중증도, 성별, 체중, 연령 등에 따라서 증감될 수 있으므로 상기 투여량이 어떠한 방법으로도 본 발명의 범위를 한정하는 것은 아니다.The dosage of the composition of the present invention may be administered in various ways depending on the patient's weight, age, sex, health status, diet, administration time, administration method, excretion rate, and severity of disease, but administration route, severity of obesity , gender, weight, age, etc. may increase or decrease, so the dosage is not intended to limit the scope of the present invention in any way.
또한, 본 발명은 화학식 1의 디아세틸 토릴린 또는 이의 식품학적으로 허용 가능한 염을 유효성분으로 포함하는 항암용 건강기능식품 조성물에 관한 것이다.In addition, the present invention relates to a health functional food composition for anticancer comprising diacetyl torillin of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
본 발명의 건강기능식품 조성물은 식품에 그대로 첨가하거나 다른 식품 또는 식품 성분과 함께 사용될 수 있고, 통상적인 방법에 따라 적절하게 사용될 수 있다. 유효성분의 혼합량은 그의 사용 목적(예방 또는 개선용)에 따라 적합하게 결정될 수 있다. 일반적으로, 건강기능식품 중에 포함되는 상기 디아세틸 토릴린의 양은 전체 건강기능식품 중량의 0.1~90 중량부로 가할 수 있다. 하지만, 건강 및 위생을 목적으로 하거나, 건강 조절을 목적으로 장기간 섭취하는 경우에는 상기 양은 상기 범위 이하일 수 있으며, 상기 범위 이상의 양으로도 사용될 수도 있다.The health functional food composition of the present invention may be added to food as it is or used together with other food or food ingredients, and may be appropriately used according to a conventional method. The mixing amount of the active ingredient may be suitably determined according to the purpose of its use (for prevention or improvement). In general, the amount of the diacetyl torillin contained in the health functional food may be added in an amount of 0.1 to 90 parts by weight of the total weight of the health functional food. However, in the case of long-term ingestion for health and hygiene purposes or for health control, the amount may be less than or equal to the above range, and an amount greater than or equal to the above range may also be used.
본 발명의 건강기능식품 조성물이 음료로 사용되는 경우, 상기 유효성분인 디아세틸 토릴린을 함유하는 것 외에는 다른 성분에는 특별한 제한이 없으며 통상의 음료와 같이 여러 가지 향미제 또는 천연 탄수화물 등을 추가 성분으로서 함유할 수 있다. 상기 천연 탄수화물의 예는 모노사카라이드, 예를 들어, 포도당, 과당 등; 디사카라이드, 예를 들어 말토스, 슈크로스 등; 및 폴리사카라이드, 예를 들어 덱스트린, 시클로덱스트린 등과 같은 통상적인 당, 및 자일리톨, 소르비톨, 에리트리톨 등의 당알콜이다. 상술한 것 이외의 향미제로서 천연 향미제(타우마틴, 스테비아 추출물(예를 들어 레바우디오시드 A, 글리시르히진 등)) 및 합성 향미제(사카린, 아스파르탐 등)를 유리하게 사용할 수 있다.When the health functional food composition of the present invention is used as a beverage, other ingredients are not particularly limited except for containing the active ingredient, diacetyl torillin, and various flavoring agents or natural carbohydrates are added as an additional ingredient like a conventional beverage. It can be contained as Examples of the natural carbohydrate include monosaccharides such as glucose, fructose and the like; disaccharides such as maltose, sucrose and the like; and polysaccharides such as conventional sugars such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol. As flavoring agents other than those described above, natural flavoring agents (taumatine, stevia extract (eg rebaudioside A, glycyrrhizin, etc.)) and synthetic flavoring agents (saccharin, aspartame, etc.) can be advantageously used. have.
본 발명의 건강기능식품 조성물은 상기 유효성분 이외에 추가로, 영양제, 비타민, 전해질, 풍미제, 착색제, 증진제, 펙트산 및 그의 염, 알긴산 및 그의 염, 유기산, 보호성 콜로이드 증점제, pH 조절제, 안정화제, 방부제, 글리세린, 알코올 및 탄산음료에 사용되는 탄산화제 중에서 선택된 하나 이상을 더 첨가하여 함유할 수 있다. 이외에도 본 발명의 건강기능식품 조성물은 천연 과일 쥬스 및 야채 음료의 제조를 위한 과육을 함유할 수 있다. 상기 과육은 독립적으로 또는 조합하여 사용할 수 있다. 상기 다양한 첨가제의 비율은 중요하진 않지만, 본 발명의 디아세틸 토릴린 100 중량부 당 0.1~20 중량부의 범위에서 선택되는 것이 일반적이다.The health functional food composition of the present invention, in addition to the above active ingredients, nutrients, vitamins, electrolytes, flavoring agents, colorants, enhancers, pectic acid and its salts, alginic acid and its salts, organic acids, protective colloidal thickeners, pH adjusters, stability It may contain one or more selected from the group consisting of a fire agent, a preservative, glycerin, alcohol, and a carbonation agent used in carbonated beverages. In addition, the health functional food composition of the present invention may contain flesh for the production of natural fruit juice and vegetable beverage. The pulp may be used independently or in combination. Although the ratio of the various additives is not critical, it is generally selected in the range of 0.1 to 20 parts by weight per 100 parts by weight of diacetyl torillin of the present invention.
이하, 실시예를 이용하여 본 발명을 더욱 상세하게 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로 본 발명의 범위가 이들에 의해 제한되지 않는다는 것은 당해 기술분야에서 통상의 지식을 가진 자에게 있어 자명한 것이다. Hereinafter, the present invention will be described in more detail using examples. These examples are only for illustrating the present invention in more detail, and it will be apparent to those of ordinary skill in the art that the scope of the present invention is not limited thereto.
실시예 1. 사상자로부터 단일물질 분리 및 정제Example 1. Separation and purification of single substances from casualties
사상자 추출물로부터 유기용매를 이용한 분획을 실시하여 n-hexane 분획물에서 단일 물질을 분리 정제한 후, 분리한 단일물질(화합물)의 구조를 질량분석 및 NMR 분석하여 확인하였다. After fractionation using an organic solvent from the casualty extract was performed to separate and purify a single substance from the n- hexane fraction, the structure of the separated single substance (compound) was confirmed by mass spectrometry and NMR analysis.
n-hexane 분획물을 실리카겔 플래시 칼럼크로마토그래피(Silica gel flash column chromatography), 실리카겔 오픈 칼럼크로마토그래피(Silica gel open column chromatography), Sephadex LH-20 칼럼크로마토그래피(Sephadex LH-20 column chromatography), 역상(ODS) MPLC(medium pressure liquid chromatography) 및 HPLC를 이용하여 디아세틸 토릴린(Tr-10)을 순수하게 분리 정제하였다.The n- hexane fraction was subjected to silica gel flash column chromatography, silica gel open column chromatography, Sephadex LH-20 column chromatography, reversed phase (ODS) ) Diacetyl torillin (Tr-10) was purely separated and purified using MPLC (medium pressure liquid chromatography) and HPLC.
이후, 사상자 추출물의 n-hexane 분획에 순수분리된 화합물에 대하여 질량분석 및 400MHz FT-NMR spectrometer(Varian, USA)을 이용하여 화학식 1의 구조로 되어 있는 디아세틸 토릴린(Tr-10)의 구조를 확인하였다. Thereafter, the structure of diacetyl torillin (Tr-10) having the structure of Formula 1 using mass spectrometry and 400 MHz FT-NMR spectrometer (Varian, USA) for the purely separated compound in the n -hexane fraction of the casualty extract was confirmed.
[화학식 1][Formula 1]
실시예 2. 디아세틸 토릴린 Tr-10의 항암 효과 확인(WST-1 어세이) Example 2. Confirmation of anticancer effect of diacetyl torillin Tr-10 (WST-1 assay)
6종의 암세포주에 대한 디아세틸 토릴린(Tr-10)의 세포독성을 확인하였다. 폐암(A549), 위암(AGS), 간암(Hep3B)), 유방암(MDA-MB-231), 대장암(HCT116) 및 췌장암(BxPC-3) 세포를 96웰 플레이트에 5×103 cells/well의 양으로 분주하고, 디아세틸 토릴린(Tr-10)을 10, 20, 40, 60, 80, 100㎍/㎖의 농도로 각각 24시간 동안 처리하였다. The cytotoxicity of diacetyl torillin (Tr-10) against six cancer cell lines was confirmed. Lung cancer (A549), stomach cancer (AGS), liver cancer (Hep3B)), breast cancer (MDA-MB-231), colorectal cancer (HCT116) and pancreatic cancer (BxPC-3) cells in 96-well plates 5 × 10 3 cells/well was aliquoted in an amount of , and diacetyl torillin (Tr-10) was treated at concentrations of 10, 20, 40, 60, 80, and 100 μg/ml for 24 hours, respectively.
이후, WST(high sensitive Water Soluble Tetrazolium salt)를 이용하여 살아있는 세포의 양을 측정하였다. WST는 살아있는 세포의 탈수소효소(dehydrogenase)와 반응하여 오렌지 색의 수용성 포르마잔(formazan)을 생성하는데, WST와 반응하는 탈수소효소(dehydrogenase)는 대사적으로 왕성한 활동을 하는 세포의 미토콘드리아 전자전달계에 존재하는 효소로 살아있는 세포에만 유효하므로, 포르마잔(formazan)의 생성은 살아있는 세포 수에 비례하는 상관관계를 가지게 된다. 따라서 450nm에서의 흡광도를 측정하여 포르마잔의 생성을 통한 세포생존율을 확인하였다. Then, the amount of live cells was measured using high sensitive water soluble tetrazolium salt (WST). WST reacts with dehydrogenase of living cells to produce orange-colored water-soluble formazan. Dehydrogenase that reacts with WST is present in the mitochondrial electron transport chain of metabolically active cells. Since it is an enzyme that is effective only in living cells, the production of formazan has a correlation proportional to the number of living cells. Therefore, the absorbance at 450 nm was measured to confirm the cell viability through the formation of formazan.
그 결과 도 1 내지 6에 개시한 바와 같이, 본 발명의 디아세틸 토릴린 Tr-10은 폐암, 위암, 간암, 유방암, 대장암 및 췌장암 세포에 대한 세포 생존율이 감소하는 것을 확인함으로써, 폐암, 위암, 간암, 유방암, 대장암 및 췌장암에 대한 항암 활성이 있다는 것을 확인하였다. As a result, as shown in Figures 1 to 6, diacetyl torillin Tr-10 of the present invention by confirming that the cell viability for lung cancer, stomach cancer, liver cancer, breast cancer, colorectal cancer and pancreatic cancer cells decreases, lung cancer, gastric cancer , it was confirmed that there was anticancer activity against liver cancer, breast cancer, colorectal cancer and pancreatic cancer.
Claims (6)
[화학식 1]
A pharmaceutical composition for anticancer comprising a diacetyl torilin of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
[화학식 1]
A health functional food composition for anticancer comprising the diacetyl torillin of Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.
[Formula 1]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200017809A KR102441302B1 (en) | 2020-02-13 | 2020-02-13 | Composition for anti-cancer containing deacetyl torilin as effective component |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020200017809A KR102441302B1 (en) | 2020-02-13 | 2020-02-13 | Composition for anti-cancer containing deacetyl torilin as effective component |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20210103268A KR20210103268A (en) | 2021-08-23 |
KR102441302B1 true KR102441302B1 (en) | 2022-09-07 |
Family
ID=77499477
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020200017809A KR102441302B1 (en) | 2020-02-13 | 2020-02-13 | Composition for anti-cancer containing deacetyl torilin as effective component |
Country Status (1)
Country | Link |
---|---|
KR (1) | KR102441302B1 (en) |
-
2020
- 2020-02-13 KR KR1020200017809A patent/KR102441302B1/en active IP Right Grant
Non-Patent Citations (4)
Title |
---|
Arch Phsarm. Res., 29(2), 131-134, 2006. |
Helvetica Chimica Acta, 93(4), 692-697, 2010. |
Tetrahedron Letters, 37, 4499-4504, 1966. |
Tetrahedron, 25(19), 4751-4765, 1969. |
Also Published As
Publication number | Publication date |
---|---|
KR20210103268A (en) | 2021-08-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR20170109703A (en) | A pharmaceutical composition for preventing or treating cancer comprising fractions of herbal mixture extract | |
KR100527109B1 (en) | Pharmaceutical composition comprising the extract of Allium tuberosum ROTTER for the prevention and treatment of gout. | |
KR102441302B1 (en) | Composition for anti-cancer containing deacetyl torilin as effective component | |
KR102410771B1 (en) | Composition for preventing or treating sarcopenia comprising blueberry extract | |
KR100527105B1 (en) | Pharmaceutical composition comprising the extract of Allium tuberosum ROTTER for the prevention and treatment of gout | |
KR102185919B1 (en) | Composition contaning herbal mixture extract for improving, alleviating or treating side-effect of anticancer drug | |
KR102092729B1 (en) | Pharmaceutical composition for preventing or treating liver damage comprising Curcuma longa extract | |
KR101971986B1 (en) | Composition comprising Silverberry like taxillus extract for preventing or treating cancer | |
KR102487793B1 (en) | New compound isolated from Torilidis Fructus and pharmaceutical composition for anti-cancer containing the same as effective component | |
KR101597187B1 (en) | A composition comprising the extract of Melia azedarach showing anti-cancer activity against stomach tumor | |
KR100417243B1 (en) | Pharmaceutical composition comprising the extract of Phyllostachys nigra var. henonis having anti-inflammatory activity for the prevention and treatment of inflammatory disease | |
KR102302047B1 (en) | Composition for hepatoprotective and ameliorating hangover | |
KR20200089527A (en) | Composition comprising extracts of Acorus gramineus and Dendropanax morbifera for anti-inflammation | |
KR102453634B1 (en) | Composition for the prevention or treatment of inflammatory bowel disease comprising Zizyphus jujuba mill extract | |
KR20150031373A (en) | Phamaceutical and food composition for preventing or treating obesity comprising extract of leaf from Hoppophea rhamnoids as effective component | |
KR102392292B1 (en) | Composition for preventing or treating cachexia and muscle loss comprising pheniflorin | |
KR102647997B1 (en) | Composition for preventing, improving, or treating degenerative arthritis comprising steamed ginger extract or 1-dehydro-6-gingerdione isolated therefrom as an active ingredient | |
KR101712889B1 (en) | Pharmaceutical composition comprising Zingiber mioga extracts or its fractions for prevention and treatment of neurodegenerative disorders as an active ingredient | |
KR20190110204A (en) | Kyung-ok-go having high acceptability and anti-diabetes activity adding the silk of zea mays and pumpkin | |
KR102588240B1 (en) | Composition for Improving, Preventing or Treating Helicobacter pylori Infection | |
KR102430399B1 (en) | A composition for improving, preventing and treating of gastrointestinal disease | |
KR102003354B1 (en) | Composition comprising Spike mulberry mistletoe extract for treating diabetes | |
KR20120073797A (en) | Pharmaceutical composition comprising for preventing and treating an articular rheumatism, extract from the mixture of ponciri fructus, lonicerae flos and angelicae dahuricae radix | |
KR100547558B1 (en) | Composition for the prevention and treatment of hepatitis containing acid garlic extract as an active ingredient | |
WO2013133677A1 (en) | Composition containing reaction mixture of red-ginseng extract and persimmon vinegar for preventing or treating vascular diseases |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant |