CN106928289B - A kind of four glucosides of acylation flavones and its extracting method and application - Google Patents
A kind of four glucosides of acylation flavones and its extracting method and application Download PDFInfo
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- CN106928289B CN106928289B CN201710098381.5A CN201710098381A CN106928289B CN 106928289 B CN106928289 B CN 106928289B CN 201710098381 A CN201710098381 A CN 201710098381A CN 106928289 B CN106928289 B CN 106928289B
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- flavones
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- 229930182478 glucoside Natural products 0.000 title claims abstract description 25
- 229930003944 flavone Natural products 0.000 title claims abstract description 23
- 235000011949 flavones Nutrition 0.000 title claims abstract description 23
- 150000002213 flavones Chemical class 0.000 title claims abstract description 17
- 150000008131 glucosides Chemical class 0.000 title claims abstract description 17
- 230000010933 acylation Effects 0.000 title claims abstract description 14
- 238000005917 acylation reaction Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 56
- 229930182470 glycoside Natural products 0.000 claims abstract description 40
- 150000002338 glycosides Chemical class 0.000 claims abstract description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000000284 extract Substances 0.000 claims abstract description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 12
- 229940079593 drug Drugs 0.000 claims abstract description 10
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 238000004440 column chromatography Methods 0.000 claims abstract description 9
- 235000005911 diet Nutrition 0.000 claims abstract description 9
- 230000037213 diet Effects 0.000 claims abstract description 9
- 229940093499 ethyl acetate Drugs 0.000 claims abstract description 9
- 235000019439 ethyl acetate Nutrition 0.000 claims abstract description 9
- 239000000843 powder Substances 0.000 claims abstract description 8
- 238000002386 leaching Methods 0.000 claims abstract description 7
- 239000002024 ethyl acetate extract Substances 0.000 claims abstract description 6
- 241001122767 Theaceae Species 0.000 claims abstract 12
- 238000010828 elution Methods 0.000 claims description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 35
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 34
- 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 claims description 10
- 238000001641 gel filtration chromatography Methods 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 8
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 238000004090 dissolution Methods 0.000 claims description 3
- 239000002552 dosage form Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims 1
- 239000000741 silica gel Substances 0.000 claims 1
- 229910002027 silica gel Inorganic materials 0.000 claims 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 abstract description 16
- -1 Kaempferol glucosides Chemical class 0.000 abstract description 15
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempherol Natural products C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 abstract description 12
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 abstract description 10
- 235000008777 kaempferol Nutrition 0.000 abstract description 10
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 abstract description 10
- 238000005516 engineering process Methods 0.000 abstract 1
- 235000013616 tea Nutrition 0.000 description 63
- 244000269722 Thea sinensis Species 0.000 description 44
- 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 12
- 210000001789 adipocyte Anatomy 0.000 description 7
- 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 6
- 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 6
- 210000004027 cell Anatomy 0.000 description 6
- 235000005875 quercetin Nutrition 0.000 description 6
- 229960001285 quercetin Drugs 0.000 description 6
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 235000009569 green tea Nutrition 0.000 description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 4
- QZMAEZWZCGBZFK-AOJWCAIYSA-N (2s,3s,4s,5r,6r)-6-[[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2s,3r Chemical compound O([C@H]1[C@H](O)[C@H](O[C@H]([C@@H]1O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@]1(CCC(C[C@H]14)(C)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)C(O)=O)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O QZMAEZWZCGBZFK-AOJWCAIYSA-N 0.000 description 3
- YSCJAYPKBYRXEZ-HZPINHDXSA-N (2s,3s,4s,5r,6r)-6-[[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4-[(2s,3r,4s, Chemical compound O([C@H]1[C@H](O)[C@H](O[C@H]([C@@H]1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H]1CC[C@]2(C)[C@H]3CC=C4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@]1(CCC(C[C@H]14)(C)C)C(=O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)C(O)=O)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O YSCJAYPKBYRXEZ-HZPINHDXSA-N 0.000 description 3
- QZMAEZWZCGBZFK-UHFFFAOYSA-N 28-(beta-D-Glucopyranosyloxy)-28-oxoolean-12-en-3beta-yl 3-O-(beta-D-glucopyranosyl)-beta-D-glucopyranosiduronic acid Natural products C12CC(C)(C)CCC2(C(=O)OC2C(C(O)C(O)C(CO)O2)O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC(C1O)OC(C(O)=O)C(O)C1OC1OC(CO)C(O)C(O)C1O QZMAEZWZCGBZFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- KPJWZUAARPJYSB-UHFFFAOYSA-N glycoside C Natural products CC1(C)OC(=O)C23CCC1C2(O)CCC(C1(CCC24)C)(C)C3CCC1C2(C)CCCC4(C)COC(C(C(O)C1O)OC2C(C(O)C(CO)O2)O)OC1COC1OC(CO)C(O)C(O)C1O KPJWZUAARPJYSB-UHFFFAOYSA-N 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000006372 lipid accumulation Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 102000004877 Insulin Human genes 0.000 description 2
- 108090001061 Insulin Proteins 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NPGIHFRTRXVWOY-UHFFFAOYSA-N Oil red O Chemical compound Cc1ccc(C)c(c1)N=Nc1cc(C)c(cc1C)N=Nc1c(O)ccc2ccccc12 NPGIHFRTRXVWOY-UHFFFAOYSA-N 0.000 description 2
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- 238000004043 dyeing Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 229930182486 flavonoid glycoside Natural products 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 230000002218 hypoglycaemic effect Effects 0.000 description 2
- 229940125396 insulin Drugs 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 1
- 235000006468 Thea sinensis Nutrition 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000020279 black tea Nutrition 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005100 correlation spectroscopy 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
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- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 150000007955 flavonoid glycosides Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000003929 heteronuclear multiple quantum coherence Methods 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
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- 210000004185 liver Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 235000021283 resveratrol Nutrition 0.000 description 1
- 229940016667 resveratrol Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 235000020338 yellow tea Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides it is a kind of separated from tealeaves the entitled tea hill that is prepared how four glucosides of acylation flavones of phenose glycosides C；It is first that Lu`an Guapian.Tea tea or yellow big tea powder is broken when preparation；Then leaching liquor is obtained with the smashed Lu`an Guapian.Tea tea of 70-80% acetone flooding or Huang great Cha, it is extracted again with methylene chloride, ethylacetate step, corresponding extraction position paste extract methylene chloride position, ethyl acetate extract and remaining water position is made by being concentrated under reduced pressure in extracting solution；Water position, which is isolated and purified, using a variety of column chromatography technologies again obtains Kaempferol glucosides C.How four glucosides of acylation flavones of phenose glycosides C can be applied to lipid-lowering diet drug in the entitled tea hill that the present invention is prepared.
Description
Technical field
The invention belongs to technical field of chemistry, and in particular to a kind of entitled tea hill how the acylation flavones tetrose of phenose glycosides C
Glycosides and its extracting method and application.
Background technique
Tea originating from China, is found and is utilized by our ancestors with its medicinal function earliest, existing away from the present
More than 3000 years history, successively experienced from it is medicinal to eat to now popularize the whole world drink differentiation.As the fashionable world
Beverage, tealeaves be not only rely on its unique flavor by consumer's pro-gaze, more crucial factor is by tealeaves institute
The functional component and health-care efficacy contained.As people are to the pay attention to day by day of health, the healthy functions research of tealeaves is also resulted in
The broad interest of researcher.Research shows that tealeaves has anticancer, anti-oxidant, lower blood-fat and reduce weight, hypoglycemic, antiallergy, sterilization, disease-resistant
The effects of poison, protection liver.
Lu`an Guapian.Tea belongs to green tea, originates in the peace of Anhui six, for one of Chinese well-known tea, there is long history inside information
With deep cultural connotation.Most tealeaves is all to be connected to pick with bud-leaf to be process, and Lu`an Guapian.Tea is then with list
Piece leaf is process, while also having both the serious skill of unique drawing in drying process, so that it is different from other green tea, together
When it is also popular among consumers.
Huang great Cha belongs to yellow tea class as its name suggests, and the Huang great Cha in Anhui mainly originates in one band of Huoshan, the spy of Huang great Cha
Selecting is that leaf is big, stalk is long, yellow yellow stuff, has the dense Gao Huoxiang split, is commonly called as a pot cake perfume (or spice).Processing raw material for Huang great Cha be with thick old leaf
Main, bored Huang is its distinctive manufacturing procedure.There is correlative study to show that Huang great Cha has good effect of lowering blood sugar and hypoglycemic in the recent period
Effect is better than green tea and black tea.
The report of chemical fundamentals about Lu`an Guapian.Tea and Huang great Cha bioactivity is fewer, if can be successfully from six peaces
Biologically active flavonoid glycoside biotic component is researched and developed in green tea produced in Anhui Province and Huang great Cha, it will to Western Anhui Lu`an Guapian.Tea
And the development and publicity of Huang great Cha brand provide certain help, while also can make important tribute to agricultural and medicine and other fields
It offers.
Summary of the invention
An object of the present invention is to provide a kind of entitled tea hill for separating and being prepared from Lu`an Guapian.Tea and Huang great Cha
How four glucosides of acylation flavones of phenose glycosides C, this entitled tea hill how four glucosides of acylation flavones of phenose glycosides C have it is as follows
Structure:
The second object of the present invention is to provide a kind of above-mentioned entitled tea hill how the system of acylation four glucosides of flavones of phenose glycosides C
Preparation Method, including following two path:
Path A:
1) raw material crushes:
Dry Lu`an Guapian.Tea made tea or Huang great Cha are taken, is pulverized into powder；
2) it extracts
Leaching liquor is obtained with the smashed Lu`an Guapian.Tea made tea of 70-80% acetone flooding or Huang great Cha, through excessive
Grade extracts and is concentrated under reduced pressure to give last remaining water position paste；
3) it isolates and purifies
By water position paste isolate and purify to obtain tea hill how phenose glycosides C.
Preferably, in the step 2) extraction, it is first big with the smashed Lu`an Guapian.Tea of 70-80% acetone flooding or Huang
Tea obtains leaching liquor, then is extracted with methylene chloride, ethylacetate step, and corresponding extraction position is made by being concentrated under reduced pressure in extracting solution
Paste extract: methylene chloride position, ethyl acetate extract and remaining water position paste.
Preferably, isolating and purifying described in the step 3) is that will successively pass through after the dissolution of water position paste
MCI column chromatography, silica gel column chromatography, Sephadex LH-20 gel filtration chromatography, Toyopearl column chromatographic isolation and purification.
Preferably, the specific steps isolated and purified described in the step 3) are as follows: by water position paste with water-soluble
MCI column is crossed after solution uses MeOH-H2O volume ratio 0: 100 to 100: 0 as gradient elution, collects wherein MeOH-H2O volume ratio
70: 30 to 80: 20 elution fraction；Then by resulting elution component through silica gel column chromatography, with CH2Cl2- MeOH volume ratio 20:
1,15: 1,10: 1,5: 1 to 0: 1 is used as gradient elution, collects wherein CH2Cl2The elution fraction of-MeOH volume ratio 5: 1；Gained is washed
De- component is again through Sephadex LH-20 gel filtration chromatography, and using MeOH as eluent, collection obtains elution fraction；Elution
Component through Toyopearl column chromatography, elution, obtains Kaempferol glucosides C again.
Path B:
1) raw material crushes:
Dry Lu`an Guapian.Tea made tea or Huang great Cha are taken, is pulverized into powder；
2) it extracts
Leaching liquor is obtained with the smashed Lu`an Guapian.Tea made tea of 70-80% acetone flooding or Huang great Cha, through excessive
Grade extracts and is concentrated under reduced pressure to give last remaining n-butanol portion paste；
3) it isolates and purifies
By n-butanol portion paste isolate and purify to obtain tea hill how phenose glycosides C.
Preferably, the path step B 2) extraction in, first use the smashed Lu`an Guapian.Tea of 70-80% acetone flooding
Or Huang great Cha obtains leaching liquor, then is extracted with methylene chloride, ethylacetate step, corresponding extraction is made by being concentrated under reduced pressure in extracting solution
Take position paste extract: methylene chloride position, ethyl acetate extract and remaining water position, water position extracting n-butyl alcohol,
Finally obtain n-butanol portion paste.
Preferably, the path step B 3) described in isolate and purify be by n-butanol portion paste dissolution after according to
It is secondary to isolate and purify to obtain Kaempferol glucosides C through MCI column chromatography, Sephadex LH-20 gel filtration chromatography.
Preferably, the path step B 3) described in the specific steps isolated and purified are as follows:
MCI column chromatography is crossed after n-butanol portion paste is dissolved with water uses MeOH-H2O volume ratio 20: 80 to 100: 0
As gradient elution, the elution fraction of wherein MeOH-H2O volume ratio 70: 30 to 80: 20 is collected；Then by resulting elution group
Part is through Sephadex LH-20 gel filtration chromatography, and using methanol as eluent, collection obtains elution fraction；Elution fraction is again
It chromatographed, eluted, obtain Kaempferol glucosides C.
Preferably, in the two kinds of paths above A, B: in the step 2) extraction, organic solvent, which extracts, uses immersion way
It extracts, i.e., is all equally separately immersed in smashed Lu`an Guapian.Tea or Huang great Cha in organic solvent 70-80 hours；Or by powder
Lu`an Guapian.Tea or Huang great Cha after broken are all equally extracted with organic solvent supersonic oscillations respectively.
The third object of the present invention be by entitled tea hill as described above how the four glucosides application of acylation flavones of phenose glycosides C
Application in terms of lipid-lowering diet drug.
Specifically by tea hill as described above how four glucosides of acylation flavones of phenose glycosides C and pharmaceutically general
A kind of lipid-lowering diet drug is made in auxiliary material, and the pharmaceutical dosage form includes oral type, external application type and injection-type.
Beneficial effects of the present invention are as follows:
1) confirm how acylation four glucosides of flavones of phenose glycosides C is in induction in entitled tea hill of the present invention by test
There is certain inhibition lipid accumulation effect in 3T3-L1 cell, in terms of can be applied to preparation lipid-lowering diet drug.Therefore the present invention
The flavonoid glycoside compound with medicinal actives provided has great importance to agricultural and field of medicaments；
2) more extensive prospect is provided using Lu`an Guapian.Tea and Huang great Cha for effective exploitation simultaneously.
3) preparation method of the present invention is simple, and cost is relatively low.
Detailed description of the invention
Fig. 1 be tea hill how the chemical structural formula of phenose glycosides C.
Fig. 2 is that how phenose glycosides C and the other three flavone glycoside test the inhibition of lipid accumulation in 3T3-L1 cell in tea hill
Schematic diagram, wherein 1 for tea hill how phenose glycosides C, 2 for tea hill how phenose glycosides A, 3 be tea quercetin glycoside C, and 4 be tea quercetin glycoside
A。
Specific embodiment
Embodiment of the present invention is described in detail below in conjunction with embodiment, but those skilled in the art will
Understand, the following example is merely to illustrate the present invention, and should not be taken as limiting the scope of the invention.
One, tea hill how the preparation of phenose glycosides C
Embodiment 1:
From the preparation in Lu`an Guapian.Tea
(1) 9.0 kilograms of dry Lu`an Guapian.Tea made teas are taken, and are pulverized into powder；
(2) 9.0 kilograms of dry Lu`an Guapian.Teas, 29 liter of 80% acetone water room temperature is extracted 72 hours first, is then existed
Ultrasound extraction 2 hours under 70Hz；Obtain 80% acetone water position extracting solution；It is extracted three times by above-mentioned steps, combined extract simultaneously will
Extracting solution is concentrated into paste, obtains 5 liters of extracting solution；
Then 5 liters of methylene chloride of extracting solution are extracted three times, obtains water layer and dichloromethane layer, merge dichloromethane layer simultaneously
Concentration obtains methylene chloride and extracts 400 grams of medicinal extract；
Water layer adds 4 liters of ethyl acetate extractions three times again, obtains water layer and ethyl acetate layer, respectively combined ethyl acetate layer and water
760 grams of ethyl acetate extract medicinal extract are obtained after layer concentration, 630 grams of the position get Shui medicinal extract.
(3) 400 position Ke Shui medicinal extract 500mL hot water dissolvings are taken, then are chromatographed by MCI column, MeOH-H is used2O volume
Than 0: 100 to 100: 0 gradient elution, wherein MeOH-H is collected2The elution fraction of O volume ratio 70: 30 to 80: 20；Then by institute
The elution component obtained is through silica gel column chromatography, with CH2Cl2- MeOH volume ratio 20: 1,15: 1,10: 1,5: 1 to 0: 1 is washed as gradient
It is de-, collect wherein CH2Cl2The elution fraction of-MeOH volume ratio 5: 1；Gained elutes component again through Sephadex LH-20 gel column
Chromatography, using MeOH as eluent, collection obtains seven elution fractions；Component the six channels Toyopearl column chromatography, with methanol
As eluent, collection obtains four elution fractions；Component two be tea hill how phenose glycosides C (kaempferol 3-O- [E-
p-coumaroyl-(1→2)][α-L-arabinopyranosyl-(1→3)][β-D-glucopyranosyl-(1→3)-α-
L-rhamnopyranosyl (1 → 6)]-β-D-glucopyranoside, 12.7 milligrams).The separation process is also assigned to simultaneously
The other three flavone glycoside, respectively tea hill how phenose glycosides A, tea quercetin glycoside A, tea quercetin glycoside C.
Preparation in 2: Cong Huang great tea of embodiment
(1) 10 kilograms of dry Huang great Cha are taken, and are pulverized into powder；
(2) it first uses 30 liter of 80% acetone water room temperature to extract 72 hours 10 kilograms of dry Huang great Cha first, then exists
Ultrasound extraction 2 hours under 70Hz；Obtain 80% acetone water position extracting solution；It is extracted three times by above-mentioned steps, combined extract simultaneously will
Extracting solution is concentrated into paste, obtains 5 liters of extracting solution；
Then 5 liters of methylene chloride of extracting solution liquid are extracted three times, obtains water layer and dichloromethane layer, merge dichloromethane layer
And be concentrated, it obtains methylene chloride and extracts 700 grams of medicinal extract.
Water layer adds 4 liters of ethyl acetate extractions three times again, obtains water layer and ethyl acetate layer, combined ethyl acetate layer obtains acetic acid second
625 grams of esteratic site medicinal extract.
Water layer adds 3L extracting n-butyl alcohol three times, obtains water layer and n-butanol layer, after merging n-butanol layer and water layer concentration respectively
128 grams of n-butanol portion medicinal extract are obtained, 150 grams of the position get Shui medicinal extract.
93.4 grams of n-butanol portion medicinal extract 150mL hot water dissolvings are taken, is chromatographed by MCI column, uses MeOH-H2O volume
It is used as gradient elution than 20: 80 to 100: 0, collects wherein MeOH-H2The elution fraction of O volume ratio 70: 30 to 80: 20；Then
By resulting elution component through Sephadex LH-20 gel filtration chromatography, using methanol as eluent, collection obtains eight
Elution fraction；Component four is through Sephadex LH-20 gel filtration chromatography, and using methanol as eluent, collection obtains three and washes
De- component；Component one is Kaempferol glucosides C (kaempferol 3-O- [E-p-coumaroyl- (1 → 2)] [α-L-
arabinopyranosyl-(1→3)][β-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl(1→
6)]-β-D-glucopyranoside, 6.1 milligrams).
Embodiment 3
Raw material is changed to 9.0 kilograms of dry Huang great Cha, using the method for embodiment 1, tea hill of the present invention is prepared how
4.2 milligrams of phenose glycosides C.
Embodiment 4
Raw material is changed to 10 kilograms of dry Lu`an Guapian.Tea made teas, the present invention is prepared using the method for embodiment 2
Tea hill how 12.5 milligrams of phenose glycosides C.
As can be seen from the above embodiments, from after extracting n-butyl alcohol, later separation purifies to obtain the step of the compound
It is rapid obvious simple.
Comparative example 1
A kind of jasmine tea of purchase in the market, is not extracted of the present invention using the method for embodiment 1 and embodiment 2
Tea hill how phenose glycosides C.
Tea hill of the present invention how phenose glycosides C characteristic it is as follows:
1) methanol and DMSO, are dissolved in, yellow solid,
2)、IR(KBr)vmax(cm-1): 3394,1700,1654,1604,1511,1078；
3), HR-ESI-MS:m/z1033.28429 ([M-H]-, C24H19O9 -Calculated value be 1033.28251)；Core
Resonance spectroscopic data is shown in Table 1.
Table 1: tea hill how phenose glycosides C spectroscopic data of the nuclear magnetic resonance (1H NMR in 600MHz,13C NMR is in 150MHz condition
Lower test, δ unit are ppm, and coupling constant J unit is Hz, and solvent is deuterated DMSO).
The spectroscopic data of the nuclear magnetic resonance of 1. Kaempferol glucosides C of table
All spectral datas pass through1H NMR,13C NMR, ESI-HR-MS and1H-1The two dimensions such as H COSY, HMQC, HMBC
Nuclear magnetic resoance spectrum ownership, it was demonstrated that the structure of gained compound.
Two, how the inhibition 3T3-L1 adipocyte lipid accumulation of phenose glycosides C and the other three flavone glycoside are tested in tea hill
Cell culture: taking 3T3-L1 PECTORAL LIMB SKELETON, with contain 10% fetal calf serum and 1% dual anti-DMEM culture medium, with
Certain condition (37 DEG C of temperature, gas concentration lwevel 5%, humidity 95%) is incubated in carbon dioxide constant incubator.
Cell viability detection: cell viability is measured using thiazole blue laws.Take 3T3-L1 PECTORAL LIMB SKELETON according to 3 × 104A/
ML is inoculated in 96 orifice plates, and culture is separately added into the compound (25,50,100 and 200 μM) of different quality concentration afterwards for 24 hours, continuous to train
The thiazolyl blue culture solution (5mg/ml) of 20 μ l is added after feeding 72h, blots culture solution after cultivating 4h, 150 μ l diformazans are added in every hole
Base sulfoxide, shaking table use microplate reader to measure OD value at 490nm wavelength after vibrating 10min.
The induction differentiation of cell and oil red O stain: 3T3-L1 PECTORAL LIMB SKELETON is inoculated in 24 orifice plates, is cultivated using DMEM
Base (containing 10% fetal calf serum) culture, after cell merges completely, addition insulin differentiating inducer (10 μ g/mL insulin,
0.5mol/L3- isobutyl group 1- methyl yellow Piao purine and 1 μm of ol/L dexamethasone) induction；DMEM culture medium culture 8 is replaced with after 3 days
It.Self-induction starts (0 day), and different quality concentration (25,50,100 μM) compound is added in experimental group, and resveratrol is as positive
Control group (20 μ g/mE).Cell is rinsed with phosphate buffer after 8 days, after being fixed with 10% formalin again with 60% it is different
Propyl alcohol elution is observed fatty deposition in endochylema and is taken pictures using 0.5% oil red O stain.Every hole is added after oil red dyeing
The cell of 400ul isopropanol processing dyeing goes out to detect OD value in microplate reader 510nm.
The experimental results showed that how phenose glycosides C and other three flavone glycosides hardly produce 3T3-L1 fat cell in tea hill
Raw cytotoxicity, while the accumulation of lipid in 3T3-L1 fat cell can be effectively reduced.It is acted on when Kaempferol glucosides C is 50 μM
When 3T3-L1 fat cell, the relative amount of the lipid in 3T3-L1 fat cell is 55.53%；Kaempferol glucosides C is 100 μM
When, the relative amount of the lipid in 3T3-L1 fat cell is reduced to 50% or less.Illustrate tea hill how phenose glycosides C can be effective
Inhibit the accumulation of lipid in 3T3-L1 fat cell, while this inhibitory effect is not that how phenose glycosides C is thin to 3T3-L1 by tea hill
Caused by the cytotoxicity of born of the same parents.
Cytotoxicity of the 2. 4 flavone glycoside monomeric compounds of table to 3T3-L1 cell
1 for tea hill how phenose glycosides C, 2 for tea hill how phenose glycosides A, 3 be tea quercetin glycoside C, and 4 be tea quercetin glycoside A.
Therefore the entitled tea hill of the present invention is in terms of how four glucosides of acylations flavones of phenose glycosides C can apply lipid-lowering diet drug
Preparation.
Specifically by tea hill as above of the invention, how four glucosides of acylation flavones of phenose glycosides C is by medically acceptable
Dosage and pharmaceutically general auxiliary material a kind of lipid-lowering diet drug is made.The pharmaceutical dosage form include oral type, external application type and
Injection-type etc..
The above content describes basic principles and main features of the invention, and the present invention is not limited to the above embodiments,
Without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes and improvements are all
It falls into scope of the claimed invention.
Claims (6)
1. a kind of four glucosides of acylation flavones, it is characterised in that be named as tea hill how phenose glycosides C, have structure as follows:
2. being acylated the preparation method of four glucosides of flavones according to claim 1, it is characterised in that in turn include the following steps:
1) raw material crushes:
Dry Lu`an Guapian.Tea made tea or Huang great Cha are taken, is pulverized into powder；
2) it extracts:
Leaching liquor is obtained with the smashed Lu`an Guapian.Tea made tea of 70-80% acetone flooding or Huang great Cha, then uses dichloromethane
Corresponding extraction position paste extract: methylene chloride portion is made by being concentrated under reduced pressure in alkane, ethylacetate step extraction, extracting solution
Position, ethyl acetate extract and remaining water position paste；
3) it isolates and purifies:
MCI column is crossed after water position paste is dissolved with water uses MeOH-H2O volume ratio 0:100 to 100:0 is used as gradient elution,
Collect wherein MeOH-H2The elution fraction of O volume ratio 70:30 to 80:20；Then by resulting elution component through silica gel column layer
Analysis, with CH2Cl2- MeOH volume ratio 20:1,15:1,10:1,5:1 to 0:1 are used as gradient elution, collect wherein CH2Cl2-MeOH
The elution fraction of volume ratio 5:1；Gained elutes component again through Sephadex LH-20 gel filtration chromatography, using MeOH as eluant, eluent
Elution, collection obtain elution fraction；Elution fraction again through Toyopearl column chromatography, elution, obtain tea hill how phenose glycosides C.
3. being acylated the preparation method of four glucosides of flavones according to claim 1, it is characterised in that in turn include the following steps:
1) raw material crushes:
Dry Lu`an Guapian.Tea made tea or Huang great Cha are taken, is pulverized into powder；
2) it extracts:
Leaching liquor first is obtained with the smashed Lu`an Guapian.Tea made tea of 70-80% acetone flooding or Huang great Cha, then uses dichloromethane
Corresponding extraction position paste extract: methylene chloride portion is made by being concentrated under reduced pressure in alkane, ethylacetate step extraction, extracting solution
Position, ethyl acetate extract and remaining water position, water position extracting n-butyl alcohol finally obtain n-butanol portion paste；
3) it isolates and purifies:
MCI column chromatography will be crossed after the dissolution of n-butanol portion paste uses MeOH-H2O volume ratio 20:80 to 100:0 is used as gradient
Wherein MeOH-H is collected in elution2The elution fraction of O volume ratio 70:30 to 80:20；Then resulting elution component is passed through
Sephadex LH-20 gel filtration chromatography, using methanol as eluent, collection obtains elution fraction；Elution fraction passes through again
Sephadex LH-20 gel filtration chromatography, elution, obtain tea hill how phenose glycosides C.
4. a kind of be acylated application of four glucosides of flavones in terms of preparing lipid-lowering diet drug as described in claim 1.
5. a kind of lipid-lowering diet drug, which is characterized in that the drug by being acylated four glucosides of flavones as described in claim 1
It is made with auxiliary material.
6. lipid-lowering diet drug according to claim 5, which is characterized in that the pharmaceutical dosage form is oral type, external application type
And injection-type.
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| CN101153048A (en) * | 2007-06-28 | 2008-04-02 | 复旦大学 | Tea polyphenol monomer and separation process thereof |
| CN104592330A (en) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative |
| CN105198943A (en) * | 2015-09-24 | 2015-12-30 | 安徽农业大学 | Acylation flavone glycoside named camellikaempferoside A and preparing method and application thereof |
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| CN101153048A (en) * | 2007-06-28 | 2008-04-02 | 复旦大学 | Tea polyphenol monomer and separation process thereof |
| CN104592330A (en) * | 2015-02-03 | 2015-05-06 | 天津科技大学 | Kaempferol derivative separated from Sophora japonica as well as preparation method and application of kaempferol derivative |
| CN105198943A (en) * | 2015-09-24 | 2015-12-30 | 安徽农业大学 | Acylation flavone glycoside named camellikaempferoside A and preparing method and application thereof |
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