CN106518629B - 甘草叶的活性成分及其结构和用途 - Google Patents
甘草叶的活性成分及其结构和用途 Download PDFInfo
- Publication number
- CN106518629B CN106518629B CN201510566007.4A CN201510566007A CN106518629B CN 106518629 B CN106518629 B CN 106518629B CN 201510566007 A CN201510566007 A CN 201510566007A CN 106518629 B CN106518629 B CN 106518629B
- Authority
- CN
- China
- Prior art keywords
- leaves
- glycyrrhiza uralensis
- uralensis fisch
- compound
- dihydro
- 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.)
- Active
Links
- 240000008917 Glycyrrhiza uralensis Species 0.000 title claims abstract description 26
- 235000000554 Glycyrrhiza uralensis Nutrition 0.000 title claims abstract description 26
- 239000000470 constituent Substances 0.000 title abstract description 7
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims abstract description 8
- -1 alkenyl Stilbene Chemical compound 0.000 claims abstract description 8
- 235000021286 stilbenes Nutrition 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 abstract description 13
- 230000000694 effects Effects 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 9
- 229940079593 drug Drugs 0.000 abstract description 8
- 235000013305 food Nutrition 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 4
- 108010056771 Glucosidases Proteins 0.000 abstract description 2
- 102000004366 Glucosidases Human genes 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 17
- 229940125904 compound 1 Drugs 0.000 description 16
- 239000000523 sample Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000004615 ingredient Substances 0.000 description 11
- 238000010828 elution Methods 0.000 description 10
- 108010001394 Disaccharidases Proteins 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 230000003078 antioxidant effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical group CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 6
- 241000202807 Glycyrrhiza Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- WEPBGSIAWZTEJR-UHFFFAOYSA-N 3',4',5,7-tetrahydroxy-3-methoxyflavone Chemical compound O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C(O)=C1 WEPBGSIAWZTEJR-UHFFFAOYSA-N 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- RXHLADDBOLOIJO-UHFFFAOYSA-N quercetin 3-methyl ether Natural products COC1=C(Oc2c(O)cc(O)cc2C1=O)c3ccc(O)c(O)c3 RXHLADDBOLOIJO-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 4
- 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 4
- 102000016679 alpha-Glucosidases Human genes 0.000 description 4
- 108010028144 alpha-Glucosidases Proteins 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 235000011797 eriodictyol Nutrition 0.000 description 4
- 230000007760 free radical scavenging Effects 0.000 description 4
- 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 4
- 239000012488 sample solution Substances 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical class C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 3
- 238000007445 Chromatographic isolation Methods 0.000 description 3
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 3
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 description 3
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 229940010454 licorice Drugs 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 238000005457 optimization Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000002137 ultrasound extraction Methods 0.000 description 3
- 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 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XREZFYPTHFWMDM-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-6-(3-methylbut-2-enyl)chromen-4-one Chemical compound O1C2=CC(O)=C(CC=C(C)C)C(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C(O)=C1 XREZFYPTHFWMDM-UHFFFAOYSA-N 0.000 description 2
- KBEFFXBSHFUQLT-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one Chemical compound C1C(=O)C2=C(O)C(CC=C(C)C)=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 KBEFFXBSHFUQLT-UHFFFAOYSA-N 0.000 description 2
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MZSGWZGPESCJAN-MOBFUUNNSA-N Melitric acid A Natural products O([C@@H](C(=O)O)Cc1cc(O)c(O)cc1)C(=O)/C=C/c1cc(O)c(O/C(/C(=O)O)=C/c2cc(O)c(O)cc2)cc1 MZSGWZGPESCJAN-MOBFUUNNSA-N 0.000 description 2
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- TUJPOVKMHCLXEL-UHFFFAOYSA-N eriodictyol Natural products C1C(=O)C2=CC(O)=CC(O)=C2OC1C1=CC=C(O)C(O)=C1 TUJPOVKMHCLXEL-UHFFFAOYSA-N 0.000 description 2
- SBHXYTNGIZCORC-UHFFFAOYSA-N eriodyctiol Natural products O1C2=CC(O)=CC(O)=C2C(=O)CC1C1=CC=C(O)C(O)=C1 SBHXYTNGIZCORC-UHFFFAOYSA-N 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 235000005875 quercetin Nutrition 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- SFQIGPZCFNTPOD-UHFFFAOYSA-N 2-[3,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one Chemical compound OC1=C(O)C(CC=C(C)C)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 SFQIGPZCFNTPOD-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 238000005084 2D-nuclear magnetic resonance Methods 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- 235000007173 Abies balsamea Nutrition 0.000 description 1
- 239000004857 Balsam Substances 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000804384 Cynomorium songaricum Species 0.000 description 1
- OEIJRRGCTVHYTH-UHFFFAOYSA-N Favan-3-ol Chemical compound OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 OEIJRRGCTVHYTH-UHFFFAOYSA-N 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 108010031186 Glycoside Hydrolases Proteins 0.000 description 1
- 102000005744 Glycoside Hydrolases Human genes 0.000 description 1
- 101001091385 Homo sapiens Kallikrein-6 Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000018716 Impatiens biflora Species 0.000 description 1
- 102100034866 Kallikrein-6 Human genes 0.000 description 1
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000233855 Orchidaceae Species 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 244000088401 Pyrus pyrifolia Species 0.000 description 1
- 235000011400 Pyrus pyrifolia Nutrition 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- RDADIXDLZPZREI-WNQIDUERSA-N SC[C@H](N)C(O)=O.OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 Chemical compound SC[C@H](N)C(O)=O.OC1CC2=CC=CC=C2OC1C1=CC=CC=C1 RDADIXDLZPZREI-WNQIDUERSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- DHNRXBZYEKSXIM-UHFFFAOYSA-N chloromethylisothiazolinone Chemical compound CN1SC(Cl)=CC1=O DHNRXBZYEKSXIM-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000000119 electrospray ionisation mass spectrum Methods 0.000 description 1
- SBHXYTNGIZCORC-ZDUSSCGKSA-N eriodictyol Chemical compound C1([C@@H]2CC(=O)C3=C(O)C=C(C=C3O2)O)=CC=C(O)C(O)=C1 SBHXYTNGIZCORC-ZDUSSCGKSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229930182497 flavan-3-ol Natural products 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical compound O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000291 postprandial effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Dermatology (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及甘草叶中抑制α‑葡萄糖苷酶活性组分的制备方法,酚性成分的结构、制备及生物活性,特别是新化合物‒α,α′‑二氢‑3,5,3′,4′‑四羟基‑2,5′‑二异戊烯基茋(α,α′‑dihydro‑3,5,3′,4′‑tetrahydroxy‑2,5′‑diisopentenylstilben)的制备、结构及生物活性,以及它们在药物、(功能)食品、化妆品等方面的应用。
Description
技术领域
本发明属于化学技术领域,涉及甘草叶中酚性成分的结构、制备及生物活性,特别是新化合物α, α′-二氢-3,5,3′,4′-四羟基-2,5′-二异戊烯基茋(α, α′-dihydro-3,5,3′,4′-tetrahydroxy-2,5′-diisopentenylstilben)的制备、结构及生物活性。
背景技术
甘草(中国药典,2010版,第一卷,80-81页)被称为“中药国老”,是中药方剂中最常用的药材,有“十方九草”之称。甘草还是食品工业中广泛应用的天然甜味剂,此外,在烟草及化妆品工业中也有应用(张继, 姚健, 丁兰. 甘草的利用研究进展. 草原与草坪2000,89(2): 12-17)。目前,医药和工业上主要使用甘草的根和根茎,而其地上部分大多被废弃或作为牲畜饲料。为了充分开发利用甘草地上部分,提高甘草资源的利用率,发明人对甘草叶的有效成分进行了研究,从中分离纯化到7种联有异戊烯基的酚类成分,包括1个新化合物(1, 见说明书图1)。碳水化合物在人体内经过小肠α-葡萄糖苷酶等作用水解为葡萄糖吸收入血,α-葡萄糖苷酶抑制剂可以降低II型糖尿病患者餐后血糖水平,使未完全消化的二糖从肠道排出,因此,α-葡萄糖苷酶抑制剂对II型糖尿病和肥胖症患者有益。另外,α-葡萄糖苷酶参与许多病毒外壳关键糖蛋白的加工成熟,其抑制剂可能成为抗病毒药物(MannsMP, Foster GR, Rockstroh JK, Zeuzem S, Zoulim F,Houghton M. The way forwardin HCV treatment−finding the right path. Nat Rev Drug Discov, 2007, 6: 991−1000)。本发明公开甘草抗氧化、抗α-葡萄糖苷酶及抗小肠二糖酶活性组分的制备方法,其主要成分特别是新的二氢茋衍生物(α, α′-二氢-3,5,3′,4′-四羟基-2,5′-二异戊烯基茋,α, α′-dihydro-3,5,3′,4′-tetrahydroxy-2,5′-diisopentenylstilben, 1)的结构、制备方法及抗氧化、抑制α-葡萄糖苷酶和小肠二糖酶活性。
发明内容
本发明的目的在于开发利用甘草地上部分,提高甘草资源的利用率,并提供对肥胖症和II型糖尿病有益的新型α-葡萄糖苷酶和小肠二糖酶抑制剂,内容包括:将甘草叶用乙醇提取, 提取液过滤浓缩后上DIAION HP20大孔树脂用水-乙醇梯度洗脱,得到甘草叶活性组分;将该活性组分经多种色谱分离纯化的甘草叶成分1-7(图1);
本发明还提供化学结构如图1所示的甘草叶成分1-7:
本发明的另一个方面,提供化合物1的组合物;
本发明还提供含有化合物1的药物制剂;
本发明的又一个方面,提供化合物1用作为抗氧化剂;
本发明的再一个方面,提供化合物1在制备抗氧化剂方面的应用;
另一个方面,本发明提供化合物1及其组合物用作药物;
本发明还提供化合物1或其组合物在抗氧化应激和/或自由基的药物方面的应用;
本发明还提供化合物1或其组合物在预防和/或治疗氧化应激和/或自由基介导的疾病的药物方面的应用;
本发明的再一方面,提供甘草叶活性组分及化合物1或其组合物的制备方法,包括步骤如下:将甘草叶用溶剂(优选95%乙醇)提取,提取液浓缩后上DIAION HP20大孔树脂用水-乙醇梯度洗脱,得到对小肠二糖酶抑制活性的活性组分(优选60%乙醇洗脱部位),该活性组分经分离纯化得甘草叶活性成分;
该甘草叶活性组分及从中分离到的成分有很强的抗氧化活性和较强的抑制α-葡萄糖苷酶和小肠二糖酶活性。该甘草叶活性组分可直接使用,也可将其中分离纯化的活性成分用于抗氧化和/或清除自由基及治疗和/或预防II型糖尿病。
因此,本发明还涉及含有上述甘草叶活性组分或化合物1的组合物,还包含药物、食品或化妆品可接受的载体。所述本发明组合物,可按常规方法,通过将所述甘草叶活性组分或纯成分与药物、食品或化妆品可接受的载体混合来制备。
在本发明甘草叶的活性成分及其结构和用途的一个优选方案中,甘草叶的活性组分及成分的制备方法和结构确定,包括以下步骤:
1)将甘草叶用95%乙醇浸泡后超声提取,提取液浓缩悬浮于水中用DIAION HP20大孔树脂分离,60%乙醇洗脱部分为活性组分;
2)上述活性组分经反相硅胶C18、硅胶、Sephadex-LH20、MCI及制备液相分离纯化得到甘草叶纯成分1-7(图1);
3)化合物2-7通过解析光谱数据及与文献值(Hayashi H, Zhang S-L, NakaizumiT, Shimura K, Yamagauchi M, Inoue K, Sarsenbaev K, Ito M, Honda G. Fieldsurvey of Glycyrrhiza plants in central Asia (2).1) Characterization ofphenolics and their variation in the leaves of Glycyrrhizaplants collected inKazakhstan. Chem Pharm Bull, 2003, 51: 1147−1152)对照确定其结构分别为6-异戊烯基槲皮素-3-甲醚(6-prenylquercetin-3-methyl ether, 2),5′-异戊烯基槲皮素(5′-prenylquercetin, 3),槲皮素-3-甲醚(quercetin-3-methyl ether, 4),6-异戊烯基圣草酚(6-prenyleriodictyol, 5),5′-异戊烯基圣草酚(5′-prenyleriodictyol, 6),8-[(顺)-3-羟甲基-2-丁烯基]-圣草酚{8-[(Z)-3-hydroxymethyl-2-butenyl]-eriodictyol, 7};化合物1的结构经过仔细解析其包括二维核磁共振光谱在内的多种光谱,确定为α, α′-二氢-3,5,3′,4′-四羟基-2,5′-二异戊烯基茋(α, α′-dihydro-3,5,3′,4′-tetrahydroxy-2,5′-diisopentenylstilben)。
本发明的创造性和新发现为:发现了新结构的二氢茋衍生物 α, α′-二氢-3,5,3′,4′-四羟基-2,5′-二异戊烯基茋。得到有望对肥胖及糖尿病患者有益的甘草叶的活性组分,发现其所含的异戊烯基黄酮和异戊烯基茋均有很好的清除DPPH自由基活性,大多数成分还有较好的抑制α-葡萄糖苷酶和小肠二糖酶活性。由于结构中的异戊烯基存在,这些活性成分的极性比相应的非异戊烯基取代黄酮大为减低,可作为低极性食品、化妆品等的抗氧化剂,或作为保健食品或药品用于肥胖或糖尿病。目前,甘草主要使用的是其根和根茎,本发明所述甘草叶的有效成分和部位为充分开发利用甘草资源提供了依据和方法。
具体实施方式
具体实施方式对本发明所涉及甘草叶成分的制备和活性测定法作进一步详细说明。这些实施例仅用来例证本发明,不应将其视为对本发明保护范围的限制。
实施例1:甘草叶的提取及活性组分的制备
将2公斤甘草叶(2013年9月采于内蒙古鄂尔多斯)用95%乙醇(10升)浸泡24小时后超声提取30分钟,过滤,残渣再用95%乙醇6升浸泡12小时后超声提取30分钟。两次提取液合并浓缩得434 g提取物。提取物悬浮于水中上样至DIAION HP20大孔树脂柱(6 ´ 23 cm色谱柱8个),用不同比例的乙醇-水梯度洗脱,60%乙醇洗脱物(118 g)显示最强的抑制小肠二糖酶活性,1 mg/ml时的抑制率为64.2%。
实施例2:甘草叶活性组分中有效成分的分离纯化及结构测定
上述活性部位(大孔树脂60%乙醇洗脱部位)经反相硅胶C18色谱分离,水-甲醇梯度洗脱,50%甲醇洗脱部分经硅胶(石油醚-乙酸乙酯6:4),Sephadex-LH20(55%甲醇)和MCI(75%甲醇)分离纯化得到化合物2(16mg)。反相硅胶C18色谱的40%甲醇洗脱部分上硅胶柱色谱分离,石油醚-乙酸乙酯6:4洗脱部分经Sephadex-LH20及MCI色谱分离得到化合物4(15mg)和7(119mg),石油醚-乙酸乙酯7:3洗脱部分用Sephadex-LH20分离,50-70%甲醇洗脱部分经MCI及制备液相色谱分离纯化得化合物3(34mg)、5(26mg)、6(45mg)及 1(27mg)。通过解析光谱数据及与文献值(Hayashi H,Zhang S-L,Nakaizumi T,Shimura K,YamagauchiM,Inoue K,Sarsenbaev K,Ito M,Honda G.Field survey of Glycyrrhiza plants incentral Asia(2).1)Characterization of phenolics and their variation in theleaves of Glycyrrhiza plants collected in Kazakhstan.Chem Pharm Bull,2003,51:1147-1152)对照确定了化合物2-7的结构分别为6-异戊烯基槲皮素-3-甲醚(2),5′-异戊烯基槲皮素(3),槲皮素-3-甲醚(4),6-异戊烯基圣草酚(5),5′-异戊烯基圣草酚(6),8-[(顺)-3-羟甲基-2-丁烯基]-圣草酚(7)。化合物1为新化合物,通过解析多种光谱数据确定了其结构;
化合物1:类白色粉末,高分辨ESI-MS负离子模式测得准分子离子峰m/z381.2065,为分子式C24H30O4的[M-H]-1峰(计算值:m/z 381.2066)。1H NMR(图2)δ:1.656(3H,s)and1.698(3H,s)and 1.718(3H,s)and 1.724(3H,s)(H-10,10′,11,11′),2.596(2H,m,H-α′),2.651(2H,m,H-α),3.201(2H,d,J=7.0Hz,H-7),3.245(2H,d,J=7.0Hz,H-7′),5.047(1H,t,J=7.0Hz,H-8),5.280(1H,t,J=7.0Hz,H-8′),6.120(1H,d,J=2.5Hz,H-6),6.146(1H,d,J=2.5Hz,H-4),6.351(1H,d,J=2.5Hz,H-6′),6.480(1H,d,J=2.5Hz,H-2′);13CNMR(图3)δ:17.90and 18.21(C-10,10′)、25.31(C-7)、25.98and 26.04(C-11,11′)、29.20(C-7′)、36.99(C-α)、38.57(C-α′)、101.33(C-4)、108.63(C-6)、113.85(C-2′)、119.06(C-2)、121.27(C-6′)、124.35(C-8′)、126.08(C-8)、129.47(C-5′)、130.51(C-9)、132.58(C-9′)、134.54(C-1′)、142.02(C-4′)、143.59(C-1)、145.85(C-3′)、156.59(C-5)、157.10(C-3);1H NMR图谱中δ1.656到1.724的两对甲基单峰分别与两对双键碳有HMBC相关,另有1对亚甲基的质子信号也与这两对双键碳相关,说明结构中有两个异戊烯基。13C NMR数据提示有2个苯环存在,1H NMR光谱中出现两对间位耦合的芳香质子信号,氢谱和碳谱还显示有另外两个亚甲基(CH2-α,α′)的信号,两者均与同样两个芳香碳原子(C-1,1′)有HMBC(图4)相关,另外,还分别与另外两个芳香碳原子有HMBC相关,提示存在1,2-二苯乙烷基本骨架。该骨架与两个异戊烯基和羟基的连接位置通过图5所示的HMBC相关的确定,因此该化合物的结构为α,α′-二氢-3,5,3′,4′-四羟基-2,5′-二异戊烯基茋;
附图说明
图1.甘草叶活性成分1-7的化学结构
图2.化合物1的1HNMR图谱
图3.化合物1的13CNMR图谱
图4.化合物1的HMBC图谱
图5.化合物1的HMBC主要相关。
实施例3:甘草叶提取物及大孔树脂所得组分中化合物1-7的含量
用超高效液相-串联四极杆电喷雾质谱(UPLC-QQQESIMS)测定成分的含量。UPLC-QQQESIMS在安捷伦Agilent 1290 infinity UPLC及 Agilent 6430 triple Quad MS上分析。优化的色谱条件为:ZORBAX Eclipse XDB-C18(2.1×50 mm,1.8 μm)色谱柱, 柱温控制在30ºC,流速设为0.4 mL/min,进样量为1 μL;色谱流动相的A 相为含0.1%甲酸的纯净水,B相为甲醇; 流动相程序:0–4 min, 10-39% B; 4-4.1 min, 39-41% B; 4.1-8 min, 41-45% B; 8-8.1 min, 45-67% B; 8.1-12 min, 61-69% B; 12-12.1 min, 69-100% B;12.1-14 min, 100% B。用质谱多反应监控(MRM)模式定量,优化后的质谱检测条件列于表1;
用上述优化的定量条件对甘草叶提取物及大孔树脂各流份分析结果列于表2。大孔树脂60%洗脱物中这7种成份的含量最高;
实施例4:1,1-二苯基苦基苯肼(DPPH)自由基清除实验
DPPH清除实验参考Ma等的方法 (Ma JN. Wang SL. Zhang K. Wu ZG, HattoriM, Chen G L. Chemical components and antioxidant activity of the peels ofcommercial apple-shaped pear (fruit of pyrus pyrifolia cv. pingguoli). J Food Sci, 2012, 10: 1097−1102)在96孔板上测定。样品孔含10 μl待测样品溶液和190 μlDPPH溶液(0.1 mM),对照孔含10 μl二甲亚砜和190 μl DPPH溶液,颜色对照孔含10 μl样品和190 μl 甲醇。避光室温反应20 min后用酶标仪测定520 nm的吸光度(A),样品对自由基的清除百分率用如下公式计算:
对自由基清除率%=100×[A对照- (A样品–A颜色对照)] /A对照
A对照为对照孔的吸光度, A样品为样品孔的吸光度, A颜色对照为颜色对照孔的吸光度;
结果(表3)显示,化合物1-7均有较强的清除DPPH自由基活性,除化合物2的清除DPPH半数有效浓度为13.9 μg/ml外,另外6个化合物清除DPPH自由基的半数有效浓度均小于6 μg/ml。
表3 甘草叶7种成分对DPPH的清除及对α-葡萄糖苷酶和麦芽糖酶的抑制活性
实施例5:甘草叶成分对α-葡萄糖苷酶和小肠二糖酶抑制活性
参考文献方法(Ma CM, Sato N, Li XY, Nakamura N, Hattori M. Flavan-3-olcontents, anti-oxidative and α-glucosidase inhibitory activities ofCynomorium songaricum. Food Chem, 2010, 118: 116−119) 在96孔板上测定对α-葡萄糖苷酶抑制活性。底物溶液为2 mM的对硝基苯酚α-D-葡萄糖苷的磷酸钾缓冲液溶液(100mM,pH 7.0)。样品孔含10 μl样品和80 μl底物溶液,对照孔用10 μl DMSO代替样品溶液。酶溶液为0.4 U/ml Bacillus Stearothermophilusα-葡萄糖苷酶。每孔加入10 μl酶溶液后在37 ºC下培养20 min。培养前后均用酶标仪测定405 nm的吸光度,通过比较样品孔的吸光度增值(ΔA样品)与对照孔的吸光度增值(ΔA对照)用下述公式计算样品对酶的百分抑制率:
抑制率%=100×[ (ΔA对照-ΔA样品) ⁄ΔA对照]
对小肠二糖酶-麦芽糖酶的抑制活性参考Meng等的方法(Meng HC, Ma CM.Flavan-3-ol-cysteine and acetylcysteine conjugates from edible reagents andthe stems of Cynomorium songaricum as potent antioxidants. Food Chem, 2013,141: 2691−2696.)提取小肠二糖酶,用PH 7的磷酸盐缓冲液将酶提取液稀释10倍后在96孔板上测定活性。每孔加入3 μl样品溶液,20 μl麦芽糖溶液(2 mg/ml)和7 μl二糖酶液。对照孔用3 μl二甲亚砜代替样品溶液,其余同上。混匀37 ºC振摇反应20 min后加入10 μl 二甲亚砜,生成的葡萄糖用南京建成的葡萄糖检测试剂盒测定。对二糖酶的抑制百分率根据520nm处的吸光度(A)按如下公式计算:
抑制率%=100×[ (A对照- A样品) ⁄ A对照]
每个样品测量4个浓度,每个浓度测定3次,从百分抑制率-浓度曲线中求出抑制50%酶活性时的浓度(IC50);
结果(表3)显示,除化合物7以外的6个成分均有较强的抑制α-葡萄糖苷酶活性,以化合物3和1的活性最高。化合物1, 3和7显示了较强的抑制麦芽糖酶活性;
由于上述实例1所述甘草叶活性组分的大多数成分均有清除自由基活性和抑制α-葡萄糖苷酶活性。因此,实例1中大孔树脂柱得到的该活性组分及实例2所得纯成分预期对肥胖和糖尿病患者有益;
本实验得到甘草活性组分的方法简单,制备条件温和,只使用无毒的常规试剂反应得到,适用于大批量生产。
上述仅为本发明较佳的具体实施方法,本发明保护范围不应受此限制,熟悉本领域的技术人员在本发明的技术范围内,以简单变化或替换所得的技术方案均落入本发明的保护范围。
Claims (1)
1.甘草叶活性成分化合物α, α′-二氢-3,5,3′,4′-四羟基-2,5′-二异戊烯基茋(α,α′-dihydro-3,5,3′,4′-tetrahydroxy-2,5′-diisopentenylstilben)。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510566007.4A CN106518629B (zh) | 2015-09-09 | 2015-09-09 | 甘草叶的活性成分及其结构和用途 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510566007.4A CN106518629B (zh) | 2015-09-09 | 2015-09-09 | 甘草叶的活性成分及其结构和用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN106518629A CN106518629A (zh) | 2017-03-22 |
CN106518629B true CN106518629B (zh) | 2019-01-11 |
Family
ID=58345506
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510566007.4A Active CN106518629B (zh) | 2015-09-09 | 2015-09-09 | 甘草叶的活性成分及其结构和用途 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN106518629B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US11479537B2 (en) * | 2017-09-28 | 2022-10-25 | Kinki University | T-type calcium channel inhibitor |
CN110872267B (zh) * | 2018-08-30 | 2022-07-08 | 复旦大学 | 一种从构树中提取的化合物及其在制备蛋白酪氨酸磷酸酶1b抑制剂中的用途 |
CN111521703B (zh) * | 2020-04-25 | 2022-06-17 | 内蒙古大学 | 液-质联用鉴定异戊烯基二氢茋的方法及新化合物的结构和应用 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101694487A (zh) * | 2009-10-13 | 2010-04-14 | 宁夏回族自治区药品检验所 | 甘草中glycyrrhisoflavone的筛选方法﹑提取方法﹑含量测定方法及用途 |
-
2015
- 2015-09-09 CN CN201510566007.4A patent/CN106518629B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101694487A (zh) * | 2009-10-13 | 2010-04-14 | 宁夏回族自治区药品检验所 | 甘草中glycyrrhisoflavone的筛选方法﹑提取方法﹑含量测定方法及用途 |
Also Published As
Publication number | Publication date |
---|---|
CN106518629A (zh) | 2017-03-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Xie et al. | Protective effect of flavonoids from Cyclocarya paliurus leaves against carbon tetrachloride-induced acute liver injury in mice | |
Garg et al. | Chemistry and pharmacology of the citrus bioflavonoid hesperidin | |
EP1800685B1 (en) | Steroidal saponin pharmaceutical composition, its preparation method and use | |
ABD EL-MAWLA et al. | Induction of biologically active flavonoids in cell cultures of Morus nigra and testing their hypoglycemic efficacy | |
Wu et al. | The hepatoprotective activity of kinsenoside from Anoectochilus formosanus | |
Lanzotti | Bioactive saponins from Allium and Aster plants | |
Hao-Cong et al. | Chemical constituents and pharmacologic actions of Cynomorium plants | |
Thabet et al. | Validation of the antihyperglycaemic and hepatoprotective activity of the flavonoid rich fraction of Brachychiton rupestris using in vivo experimental models and molecular modelling | |
Hawas et al. | A new flavonoid C-glycoside from Solanum elaeagnifolium with hepatoprotective and curative activities against paracetamol-induced liver injury in mice | |
Ye et al. | Bioactivity-guided isolation of anti-inflammation flavonoids from the stems of Millettia dielsiana Harms | |
CN106518629B (zh) | 甘草叶的活性成分及其结构和用途 | |
CN102652792A (zh) | 包含大蒜油、大蒜总多糖和大蒜总皂苷的组合物的抗癌用途 | |
Hunyadi et al. | Volatile glycosides from the leaves of Morus alba with a potential contribution to the complex anti-diabetic activity | |
CN103665082B (zh) | 雪胆葫芦烷型四环三萜化合物,含有该化合物的药物组合物及其应用 | |
Atta et al. | New Flavonoid Glycoside and Pharmacological Activities of Pteranthus dichotomus Forssk. | |
CN104370871B (zh) | 从紫红獐牙菜中分离的口山酮类及抑制乙型肝炎病毒的应用 | |
Menković et al. | Bioactive compounds of endemic species Sideritis raeseri subsp raeseri grown in national park Galicica | |
CN108997296B (zh) | 几种异戊烯基二氢茋和异戊烯基黄酮的结构和用途 | |
CN103626824B (zh) | 一种雪胆葫芦烷型四环三萜化合物,含有该化合物的药物组合物及其应用 | |
Salama et al. | A new hepatoprotective flavone glycoside from the flowers of Onopordum alexandrinum growing in Egypt | |
Ayoola et al. | Justifying antidiabetic ethnomedicinal claim of Senecio biafrae through its antihyperglycemic and anti-oxidant activities | |
Baki et al. | quareticctivity of Solidago canadensiscultivated ingypt and etermination of theostioactiveraction | |
KR100592482B1 (ko) | 감초 및 감초추출물 중의 리퀴리티게닌 함량을 증강하는방법과 추출물에서의 활성화합물 정제방법 | |
CN1129572C (zh) | 丹参多酚酸盐混合物及其制备方法和用途 | |
CN109232491A (zh) | 一种华泽兰中苯并呋喃类化合物的制备方法及用途 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |