CN105777845B - The extracting method and purposes of antimicrobial component in a kind of Idesia polycarpa - Google Patents
The extracting method and purposes of antimicrobial component in a kind of Idesia polycarpa Download PDFInfo
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- CN105777845B CN105777845B CN201410787536.2A CN201410787536A CN105777845B CN 105777845 B CN105777845 B CN 105777845B CN 201410787536 A CN201410787536 A CN 201410787536A CN 105777845 B CN105777845 B CN 105777845B
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- ethyl acetate
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- medicinal extract
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 241001299699 Idesia Species 0.000 title claims abstract description 18
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 15
- 239000000284 extract Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 41
- 239000011347 resin Substances 0.000 claims description 27
- 229920005989 resin Polymers 0.000 claims description 27
- 238000010828 elution Methods 0.000 claims description 23
- 239000012046 mixed solvent Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 239000001301 oxygen Substances 0.000 claims description 19
- FSLPMRQHCOLESF-UHFFFAOYSA-N alpha-amyrenol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C)C(C)C5C4=CCC3C21C FSLPMRQHCOLESF-UHFFFAOYSA-N 0.000 claims description 18
- JFSHUTJDVKUMTJ-QHPUVITPSA-N beta-amyrin Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C JFSHUTJDVKUMTJ-QHPUVITPSA-N 0.000 claims description 18
- QQFMRPIKDLHLKB-UHFFFAOYSA-N beta-amyrin Natural products CC1C2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C)CCC1(C)C QQFMRPIKDLHLKB-UHFFFAOYSA-N 0.000 claims description 18
- PDNLMONKODEGSE-UHFFFAOYSA-N beta-amyrin acetate Natural products CC(=O)OC1CCC2(C)C(CCC3(C)C4(C)CCC5(C)CCC(C)(C)CC5C4=CCC23C)C1(C)C PDNLMONKODEGSE-UHFFFAOYSA-N 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- -1 1- hydroxyl -6- oxo -2- cyclohexenyl Chemical group 0.000 claims description 17
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 9
- 235000013399 edible fruits Nutrition 0.000 claims description 8
- 230000007935 neutral effect Effects 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004440 column chromatography Methods 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
- 239000000741 silica gel Substances 0.000 claims description 7
- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- 229960001866 silicon dioxide Drugs 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002250 absorbent Substances 0.000 claims description 6
- 230000002745 absorbent Effects 0.000 claims description 6
- 239000007790 solid phase Substances 0.000 claims description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 5
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 5
- MSQDVGOEBXMPRF-UHFFFAOYSA-N cyclohexane;propan-2-one Chemical compound CC(C)=O.C1CCCCC1 MSQDVGOEBXMPRF-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000000120 microwave digestion Methods 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 229940125810 compound 20 Drugs 0.000 claims description 3
- 239000002032 methanolic fraction Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 2
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 2
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical group CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 11
- 238000011084 recovery Methods 0.000 abstract description 7
- 241000222122 Candida albicans Species 0.000 abstract description 5
- 241000588724 Escherichia coli Species 0.000 abstract description 5
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 5
- 229940095731 candida albicans Drugs 0.000 abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 235000011274 Benincasa cerifera Nutrition 0.000 description 14
- 244000036905 Benincasa cerifera Species 0.000 description 14
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000012459 cleaning agent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 241000894006 Bacteria Species 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- 229930013930 alkaloid Natural products 0.000 description 4
- 150000003797 alkaloid derivatives Chemical class 0.000 description 4
- 239000003899 bactericide agent Substances 0.000 description 4
- 239000000645 desinfectant Substances 0.000 description 4
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 241000219122 Cucurbita Species 0.000 description 3
- 235000009852 Cucurbita pepo Nutrition 0.000 description 3
- 241000167880 Hirundinidae Species 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 230000002421 anti-septic effect Effects 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000469 ethanolic extract Substances 0.000 description 3
- 239000000401 methanolic extract Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000012827 research and development Methods 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 2
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000008859 change Effects 0.000 description 2
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 2
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 2
- 229940074393 chlorogenic acid Drugs 0.000 description 2
- 235000001368 chlorogenic acid Nutrition 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 2
- 239000002037 dichloromethane fraction Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 239000004519 grease Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- CMWOPTLOKFKJEC-UHFFFAOYSA-N idesolide Natural products O1C(CCC=C2)(O)C2(C(=O)OC)OC21CCC=CC2(O)C(=O)OC CMWOPTLOKFKJEC-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- IJZJQOKHINBQCY-UHFFFAOYSA-N methyl 1-hydroxy-6-oxocyclohex-2-enecarboxylate Natural products COC(=O)C1(O)C=CCCC1=O IJZJQOKHINBQCY-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- UHZLTTPUIQXNPO-UHFFFAOYSA-N 2,6-ditert-butyl-3-methylphenol Chemical class CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C UHZLTTPUIQXNPO-UHFFFAOYSA-N 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 238000009631 Broth culture Methods 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 241000346136 Dracocephalum heterophyllum Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- NEZJDVYDSZTRFS-RMPHRYRLSA-N Phenyl beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=CC=C1 NEZJDVYDSZTRFS-RMPHRYRLSA-N 0.000 description 1
- 241001529246 Platymiscium Species 0.000 description 1
- 241000246044 Sophora flavescens Species 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 235000019772 Sunflower meal Nutrition 0.000 description 1
- 240000001866 Vernicia fordii Species 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
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- 238000004820 blood count Methods 0.000 description 1
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- 239000000496 cardiotonic agent Substances 0.000 description 1
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- 230000002279 cholagogic effect Effects 0.000 description 1
- 229960003405 ciprofloxacin Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 150000004141 diterpene derivatives Chemical class 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
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- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The present invention relates to a kind of extracting method of antimicrobial component in Idesia polycarpa and the purposes of extract.The extracting method of antimicrobial component has very high recovery rate and excellent separating effect in Idesia polycarpa of the present invention, various active compound can be obtained, the reactive compound extracted shows higher antibacterial activity to staphylococcus aureus, Escherichia coli and Candida albicans, is had a good application prospect in antibacterial field.
Description
Technical field
The present invention relates to the extracting method and purposes of antimicrobial component in a kind of Idesia polycarpa, belong to field of plant extraction.
Background technology
Idesia polycarpa, also known as water wax gourd, are the mutation of idesia.Aliphatic acid, phenols, sugar are mainly contained in its fruit
Glucoside, alkaloid, vitamin E etc., and with certain bioactivity, it is widely used in antibacterial, sterilization, anti-oxidant, cardiac stimulant, drop
The fields such as blood pressure.
Major part on the south the great demand applied based on Idesia polycarpa extract product broad spectrum activity, China Huanghe valley
Province is for example：The ground such as Zhejiang, Jiangsu, Anhui, Hubei, Henan, Shandong, Guangdong, Jiangxi, Guizhou, Sichuan, Yunnan, Chongqing, Shaanxi
There is large area manually to plant, research and development of products mechanism and manufacturer also arise at the historic moment.
At present, antibacterial Quality Research is extracted from natural plants has a lot, and the species of these extracts is main by volatilizing
Oil, organic acid, alkaloid, tannin, some lactones etc..
For example, CN1740137A discloses a kind of method of the chlorogenic acid extracting and purifying from sunflower meal, and chlorogenic acid has
Anti-inflammation, cholagogic, the effect stopped blooding and increase white blood cell count.
CN1789395 A are disclosed with antibacterial and/or bactericidal action Tibetan medical dracocephalum heterophyllum benth volatile oil and its prepared
With the application in antibacterial and/or bactericidal action product.
CN101084989 A are disclosed while preparing the preparation side of kuh-seng total flavone extract and total alkaloid extract
Method, kuh-seng total flavone extract and total alkaloid from sophora flavescens ait extract have antibacterial desinsection, antiviral, anti-inflammatory, available for antibacterial and
The fields such as sterilization.
All swallows etc. (all swallows etc., non-grease chemical composition [J] research and development of natural products of water wax gourd pulp, 2003,
15(1):13-17) finding the medicinal extract after the ethanol extract petroleum ether degreasing of water wax gourd pericarp, (leather is blue to wax bacillus
Family name's positive bacteria) growth there is obvious inhibitory action, and find that its effect experiment to Isolated Toad Heart shows the extraction
Take thing that there is certain cardiotonic, but further activity research is not done to each monomeric compound.Ge Hongguang etc. (Ge Hongguang,
Wu Wan moths, it is old to open natural research [J] Chinese oils, 1998,23 (6) in merit water wax gourd seeds:49-51) use baking oven
When method tests water gourd seed extract antioxidation activity, it is found that it has very strong suppression lard oxidation.They are by water
Gourd seed ethanol extract is with aqueous suspension, respectively with ethyl acetate, extracting n-butyl alcohol, and it is 4 to find n-butyl alcohol extract consumption
×l0-4Its inoxidizability has been better than 2 × l0 of consumption of 2,6- di-tert-butyl methyl phenols (BHT) during %-4%.
Based on its good biological medicine activity, researcher has also carried out the chemical constitution study to the plant.Zhou Yan
Deng (all swallows etc., non-grease chemical composition [J] research and development of natural products of water wax gourd pulp, 2003,15 (1):13-17)
The cis- cyclohexanediols of common compounds 1,2- and adjacent benzene two are also isolated from the n-butyl alcohol extract of water wax gourd pulp ethanol extract
Phenol.(the Kim Seung Hyun etc., Idesolide such as Kim Seung Hyun:A New Spiro Compound from
Idesia polycarpa [J] .Org.Lett., 2005,7 (15):3275-3277) separated from water wax gourd fruit methanolic extract
To baroque alcohols material, and to obtaining the spiro-compound of a monomer in the chloroform portion of the methanolic extract, application
NMR, MS and single crystal X-ray diffraction are identified and are named as idesolide.The, (Kim such as Kim Seung Hyun in 2007
Seung Hyun etc., Inhibitory activity of phenolic glycosidesfrom the fruits of
Idesia polycaroa on lipopolysaccharide-induced nitric oxide production in
BV2microglia[J].Planta Medica,2007,73(2):167-169) and from the second of water wax gourd fruit methanolic extract
Sour second fat, which is partially separated, obtains 1-hydroxy-6-oxocyclohex-2-enecarboxylic acid methyl ester,
The latter is probably the former catabolite.
Although it has been found that idesia platymiscium contains important phenolic glycosides, diterpene isoreactivity composition, Mao Yeshan
Seeds of a tung oil tree fruit early has been used for the rural activities such as desinsection, weeding, but chemical composition and bioactivity report are less.
Thus, for prior art defect, it is contemplated that developing a kind of extraction side of antimicrobial component in Idesia polycarpa
Method, using it is simple, efficiently extracting method extract four compounds, and its structure analyze and confirmed, respectively
β-amyrin, cupreol, 20 carbonic acid, 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] first
Base] phenyl-β-D glucosides.Meanwhile, compound β-amyrin, cupreol, 6- hydroxyls -2- [[[(1- hydroxyl -6- oxos -
2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides are to staphylococcus aureus, Escherichia coli and Candida albicans table
Reveal higher antibacterial activity, will have in fields such as antiseptic, bactericide, disinfectant, cleaning agent, cleaning agent, preservatives should
Use prospect.
The content of the invention
In order to solve drawbacks described above, present inventor has performed concentrating on studies, after a large amount of creative works are paid, so that complete
Into the present invention.
The present invention relates to the extracting method and purposes of antimicrobial component in a kind of Idesia polycarpa, the extracting method is not only simple
It is single, convenient, and recovery rate is higher, while being shown to staphylococcus aureus, Escherichia coli and Candida albicans higher
Antibacterial activity.More particularly it relates to which antimicrobial component is β-amyrin, cupreol and 6- hydroxyls in a kind of water wax gourd
The extracting method of base -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides, and
Their applications in antiseptic, bactericide, disinfectant, cleaning agent, cleaning agent, preservative field.
Specifically, in a first aspect, the invention provides a kind of extracting method of antimicrobial component in Idesia polycarpa, including
Following steps：
(1) pericarp and seed are isolated from dry Idesia polycarpa fruit, dry powder is obtained after seed is crushed, with acetic acid second
Ester is solvent microwave digestion 3-5 times, and microwave power is 500-1000W, each 10-20 minutes, extraction fluid, concentrated extracting solution
Ethyl acetate extracts medicinal extract, separating obtained filter residue extracts 4 times with mass percent concentration for 70% ethanol again, every time 10
Hour, merge extract solution, be concentrated into no alcohol taste, obtain ethanol and extract medicinal extract；Ethanol is taken to extract medicinal extract, through 100-200 mesh silicagel columns,
Dry method loading, silicagel column is successively eluted with dichloromethane, ethyl acetate and methanol, so as to be classified as 3 parts, respectively
For dichloromethane fractions, ethyl acetate portion and methanol fractions.
(2) ethyl acetate obtained by step (1) is extracted into medicinal extract through solid phase column chromatography, entered with cyclohexane-acetone mixed solvent
Row gradient elution, respectively obtains compound β-amyrin and compound cupreol；
(3) ethanol in above-mentioned steps (1) is extracted to the ethyl acetate portion obtained after the elution of medicinal extract chromatographic column, macropore is crossed and inhales
Attached resin column, carries out gradient elution with petroleum ether-ethyl acetate mixed solvent, respectively obtains the carbonic acid CH of compound 203
(CH2)18COOH and 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucose
Glycosides.
Wherein, β-amyrin, cupreol, 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl]
Oxygen] methyl] phenyl-β-D glucosides structural formula it is as follows：
In the water wax gourd of the present invention in the extracting method of antimicrobial component, the microwave power in the step (1) is 500-
1000W, for example, 500W, 600W, 700W, 800W, 900W or 1000W, more preferably 600-800W, most preferably 700W.
In the water wax gourd of the present invention in the extracting method of antimicrobial component, the concrete operations of the step (2) are as follows：Will step
Suddenly ethyl acetate obtained by (1) extracts medicinal extract through solid phase column chromatography, and gradient elution, gradient are carried out with cyclohexane-acetone mixed solvent
Elution mixed solvent cyclohexane, the volume ratio of acetone are followed successively by 30:1、25:1、20:1、15:1、10:1 and 5:1；Collect both
Volume ratio is 30:1、25:1、20:1 eluted fraction, revolving removes solvent, dries, obtains compound β-amyrin；Collect
Both volume ratios are 15:1、10:1 and 5:1 eluted fraction, revolving removes solvent, dries, obtains compound cupreol.
In the water wax gourd of the present invention in the extracting method of antimicrobial component, the concrete operations of the step (3) are as follows：Will be upper
State ethanol in step (1) and extract the ethyl acetate portion obtained after the elution of medicinal extract chromatographic column, large pore resin absorption column is crossed, with oil
Ether-ethyl acetate mixed solvent carries out gradient elution, gradient elution in the mixed solvent petroleum ether, ethyl acetate volume ratio successively
For 25:1、20:1、15:1、10:1 and 5:1, collect 25:1 and 20:1 eluted fraction, revolving removes solvent, is dried to obtain chemical combination
The carbonic acid CH of thing 203(CH2)18COOH；Collect 15:1、10:1 and 5:1 eluted fraction, revolving removes solvent, is dried to obtain 6-
Hydroxyl -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides.
In the water wax gourd of the present invention in the extracting method of antimicrobial component, the solid phase column in the step (2) is neutral oxygen
Change aluminium post.
Wherein, the granularity of the neutral alumina is 100-500 mesh, most preferably 100-200 mesh.
In the water wax gourd of the present invention in the extracting method of antimicrobial component, the macroporous absorbent resin in the step (3) is
DM301 resins, AB-8 resins, DA201 resins, D101 resins, X-5 resins or DM130 resins.
Wherein, the macroporous absorbent resin is preferably AB-8 resins, DM301 resins, DA201 resins or D101 resins,
Most preferably D101 resins.
Second aspect, the present invention relates to using the above method extract obtain β-amyrin, cupreol or 6- hydroxyls-
2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides.
The third aspect, the purposes of the reactive compound arrived the present invention relates to said extracted.
The inventors discovered that, obtained compound β-amyrin, cupreol, 6- hydroxyls are extracted by the inventive method
Base -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides are to Staphylococcus aureus
Bacterium, Escherichia coli and Candida albicans show higher antibacterial activity, thus may be used on antiseptic, bactericide, disinfectant,
The fields such as cleaning agent, cleaning agent, preservative.
Embodiment
Below by specific embodiment, the present invention is described in detail, but these exemplary embodiments are only used for example
Lift, and not the real protection scope to the present invention constitutes any type of any restriction.
Embodiment 1
(1) pericarp and seed are isolated from dry Idesia polycarpa fruit.Dry powder is obtained after seed is crushed, with acetic acid second
Ester microwave digestion 5 times, microwave power is：700W, 15 minutes every time, concentrated extracting solution obtained ethyl acetate and extracts medicinal extract, separation
The filter residue of gained is extracted 4 times with mass percent concentration for 70% ethanol again, 10 hours every time, is merged extract solution, is concentrated into
Without alcohol taste, obtain ethanol and extract medicinal extract.Ethanol is taken to extract medicinal extract, through the silicagel column that specification is 100-200 mesh particle size ranges, in dry method
Sample, silicagel column is successively with dichloromethane, ethyl acetate and methanol elution gradient.The result detected according to TLC, is classified as 3
Part, respectively dichloromethane fractions, ethyl acetate portion and methanol fractions.
(2) ethyl acetate obtained by step (1) is extracted into medicinal extract through 100-200 mesh neutral alumina progress column chromatography, with ring
Hexane-acetone mixed solvent carries out gradient elution, and gradient elution mixed solvent cyclohexane, the volume ratio of acetone are followed successively by 30:
1、25:1、20:1、15:1、10:1 and 5:1；It is 30 to collect both volume ratios:1、25:1、20:1 eluted fraction, revolving is removed
Solvent, dries, obtains compound β-amyrin；It is 15 to collect both volume ratios:1、10:1 and 5:1 eluted fraction, revolving
Solvent is removed, dries, obtains compound cupreol.
(3) ethanol in above-mentioned steps (1) is extracted to the ethyl acetate portion obtained after the elution of medicinal extract chromatographic column, D101 is crossed big
Macroporous adsorbent resin post, with petroleum ether-ethyl acetate mixed solvent carry out gradient elution, gradient elution in the mixed solvent petroleum ether,
The volume ratio of ethyl acetate is followed successively by 25:1、20:1、15:1、10:1 and 5:1, collect 25:1 and 20:1 eluted fraction, revolving
Solvent is removed, the carbonic acid CH of compound 20 is dried to obtain3(CH2)18COOH；Collect 15:1、10:1 and 5:1 eluted fraction, rotation
Solvent is evaporated off, be dried to obtain 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β -
D glucosides.
Embodiment 2-6
500W, 600W, 800W, 900W, 1000W are replaced with respectively except microwave power will be extracted in the step of embodiment 1 (1)
Outside, embodiment 2-6 is implemented with the same way with embodiment 1 respectively.
Embodiment 7-9
Except by D101 macroporous absorbent resins in the step of embodiment 1 (3) replace with respectively AB-8 resins, DM301 resins,
Outside DA201 resins, embodiment 7-9 is implemented with the same way with embodiment 1.
The characterize data difference for four compounds that above-described embodiment 1-9 is obtained is as follows：
β-amyrin
m.p.：183-185℃.
IR(KBr)cm-1：2919、2872、1463、1034.
EI-MS m/z：426[M]+。
1H-NMR(CDCl3,500MHz)δ：0.78(3H,s)、0.82(3H,s)、0.86(6H,s)、0.93(3H,s)、0.95
(3H, s), 1.04 (3H, s), 1.11 (3H, s), 5.18 (1H, t, J=3.4Hz, H-12), 3.22 (1H, dd, J=4.4,
11.2Hz, H-3 α), wherein 0.78 (3H, s), 0.81 (3H, s), 0.86 (6H, s), 0.92 (3H, s), 0.95 (3H, s), 1.01
(3H, s), 1.10 (3H, s) for 8 angular methyls it is unimodal, be pentacyclic triterpenoid；
13C-NMR(CDCl3)δ：38.6、27.5、79.1、39.6、55.1、18.2、32.5、38.6、47.3、37.1、
23.3、21.6、145.1、39.8、26.1、27.0、32.3、47.3、46.6、31.1、34.6、37.1、28.1、15.4、15.4、
16.6、26.1、38.2、33.1、23.5。
Cupreol
m.p.：135-138℃.
IR spectrum show-OH (3433cm-1) ,-C=C- groups (1630cm-1, it is weak).
EI-MS m/z：414[M]+。
1H-NMR(CDCl3)δ:5.35 (1H, d, J=5.2Hz), 3.50 (1H, m), 1.01 (3H, s), 0.92 (3H, d, J=
6.8Hz), 0.91 (3H, d, J=6.7Hz), 0.84 (3H, t, J=7.3Hz), 0.82 (3H, d, J=7.2Hz), 0.66 (3H,
s)。
13C-NMR(CDCl3)：37.1、31.5、71.6、42.1、140.5、121.5、31.8、32.0、50.1、36.4、
21.0、39.6、42.1、56.6、24.2、28.0、56.0、11.6、19.2、36.0、18.6、34.0、26.0、45.7、29.0、
19.6、19.2、23.0、11.9。
20 carbonic acid
m.p.：47-48℃.
IR：- C=O (1707cm-1), long-chain CH2(2920、2851、1466、730cm-1),
EI-MS m/z：312.2[m]+、284.2、256.2、185.1、171.1、129.0、111.0、97.0、83.0。
1H-NMR(CDCl3)δ：0.75ppm(3H,CH3), there are 17 CH in 1-2ppm2, have 1 CH in 2-3ppm2。
6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides
m.p.：152-153℃.
IR：Glycosyl (3422cm-1Place is wide and blunt peak) ,-C=C- (1636cm-1) ,-C=O (1740cm-1)、-C-O-C-
(1077cm-1、1046cm-1)、CH2(2825cm-1、1474cm-1)。
EI-MS m/z：301.4、162.0、139.9、123.0、121.9.
1H-NMR(CD3OD)δ：7.06 (1H, t, J=7.7Hz), 6.86 (1H, d, J=7.6Hz), 6.81 (1H, dd, J=
7.7Hz), 6.11 (1H, m), 5.78 (1H, dd), 5.53 (1H, d, J=12.2Hz), 5.31 (1H, d, J=12.5Hz), 4.60
(1H, d, J=5.8Hz), 3.84 (1H, m), 3.76 (1H, m), 3.52 (3H, m), 3.42 (1H, m), 2.90 (1H, m), 2.63
(1H,m)、2.52(2H,m)。
13C-NMR(CD3OD)：144.5、131.4、120.9、126.9、118.1、151.3、65.1、107.4、75.2、
77.9、80、78.4、62.4、79.3、129.6、132.8、27.2、36.9、207.6、171.8。
Comparative example 1
Except by " microwave digestion 5 times, microwave power is in embodiment 1：700W, every time 15 minutes " is replaced with " with acetic acid second
Ester is that solvent is extracted 5 times at 40 DEG C, and each 2h " outside, implements this comparative example 1 with the same way with embodiment 1, obtains chemical combination
Thing β-amyrin, cupreol, 20 carbonic acid and 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl]
Oxygen] methyl] phenyl-β-D glucosides.
Comparative example 2-3
Except the mixed solvent cyclohexane-acetone in the step of embodiment 1 (2) is replaced with into cyclohexane-ethyl acetate, ring respectively
Outside hexane-petroleum ether, this comparative example 2-3 is implemented with the same way with embodiment 1, detects and finds by TLC, in step (2)
Middle β-amyrin and cupreol are difficult to separate, and cause its yield very low.
This proves, when changing the acetone of in the mixed solvent, there is significant impact for the separating effect of product.
Comparative example 4-5
Except the macroporous absorbent resin in the step of embodiment 1 (3) is replaced with respectively, " granularity is the silicagel column of 300-400 mesh
Chromatogram " and " granularity is the neutral aluminum oxide column chromatography of 100-200 mesh " outside, this contrast are implemented with the same way with embodiment 1
Example 4-5, and obtain compound 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D
Glucoside.
By the weight divided by the gross weight of raw water gourd seed of each compound extracted in all embodiments and comparative example
Measure and draw recovery rate, compound β-amyrin, cupreol, 20 carbonic acid and 6- hydroxyls -2- [[[(1- hydroxyl -6- oxygen
Generation -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides recovery rate it is as shown in table 1.
Table 1
As can be seen from the above table：
1. when carrying out microwave abstracting, recovery rate will be significantly higher than recovery rate when not carrying out microwave abstracting, and work as microwave
Power has best extraction effect when being 700W.
2. separated in step (3) using specific macroporous absorbent resin, recovery rate will be far above silica gel column chromatography
And neutral aluminum oxide column chromatography, but the extraction effect of D101 resins is better than other resins.
3. when changing the component of elution mixed solvent in step (2), β-amyrin and β-paddy can be significantly affected
The separation of sterol, it is seen that the type selecting of the mixed solvent in the step is very crucial and important.
Performance test and stability test
Compound β-amyrin, β-paddy steroid that the present invention that each embodiment is obtained by following measurings is extracted
The sterilization of alcohol and 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D- glucosides
Performance.
Take reference culture：Staphylococcus aureus (ATCC25923), Escherichia coli (441490) bacterial strain are a little, connect respectively
Plant in nutrient broth medium, 37 DEG C of culture 18h.Each bacterial strain nutrient broth culture for taking 18h to cultivate, is made with nutrient broth
10-3Dilute for testing.Extracting waste beads bacteria strain is a little, is inoculated in improvement Martin's culture medium, 35 DEG C of culture 24h.Take 24h
The Candida albicans culture of culture, with improvement Martin's culture medium 10-3Dilute for testing.Matched somebody with somebody with doubling dilution (test tube method)
Sample preparation product, i.e. test-compound are made into initial concentration for 10mg/ml respectively, take 0.1ml plus 5.9ml nutrient broth dilute filtrations standby
With taking sterilizing test tubes 8 for each test-compound, the 1st pipe adds by reagent dilution 1ml, 2-8 pipe respectively plus 1ml battalion
Meat soup is supported, takes by reagent dilution 1ml to add in the 2nd pipe respectively, takes 1ml to the 3rd to manage after mixing, dilutes successively, the 7th pipe is suctioned out
1ml is discarded, and the 8th pipe is not added with decoction as control.Often pipe adds dilution bacterium solution 0.1ml, 37 DEG C of culture 24h.Take out observation bacterium
Growing state.Such as drug liquid tube muddiness, that is, bacterial growth is represented, for reagent thing without bacteriostasis；Represented if drug liquid tube is limpid thin
Bacteria growing is suppressed, the decoction of the greatest dilution of its energy bacteria growing inhibiting, is the minimal inhibitory concentration of the medicine
(MIC).Take ciprofloxacin hydrocloride tablets (Guangzhou white clouds pharmaceutical Co. Ltd, specification：0.25g/ pieces, are made into 0.05g/m1 solution),
Nysfungin (Zhejiang Zhenyuan Pharmaceutical Co., Ltd, specification：500mg/ pieces, are made into 200mg/ml solution), as stated above, successively
Dilution, culture, makees positive control, as a result see the table below 2.
Table 2
As can be seen from the above table, the present invention is extracted compound β-amyrin, cupreol and 6- hydroxyl -2- [[[(1-
Hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D- glucosides have good bactericidal activity can be used for resist
The fields such as microbial inoculum, bactericide, disinfectant, cleaning agent, cleaning agent, preservative.
It should be appreciated that the application of these embodiments is merely to illustrate the present invention and is not intended to limitation protection model of the invention
Enclose.In addition, it will also be appreciated that after the technology contents of the present invention have been read, those skilled in the art can make each to the present invention
Change, modification and/or variation are planted, all these equivalent form of values equally fall within the guarantor that the application appended claims are limited
Within the scope of shield.
Claims (4)
1. the extracting method of antimicrobial component, comprises the following steps in a kind of Idesia polycarpa：
(1) pericarp and seed are isolated from dry Idesia polycarpa fruit, after seed is crushed dry powder, using ethyl acetate as
Solvent microwave digestion 3-5 times, microwave power is 700W, each 10-20 minutes, and extraction fluid, concentrated extracting solution obtains acetic acid second
Ester extracts medicinal extract, and separating obtained filter residue is extracted 4 times for 70% ethanol with mass percent concentration, 10 hours every time, closed again
And extract solution, no alcohol taste is concentrated into, ethanol is obtained and extracts medicinal extract；Ethanol is taken to extract medicinal extract, through 100-200 mesh silicagel columns, in dry method
Sample, silicagel column is successively eluted with dichloromethane, ethyl acetate and methanol, so as to be classified as 3 parts, respectively dichloro
Methane moiety, ethyl acetate portion and methanol fractions；
(2) ethyl acetate obtained by step (1) is extracted into medicinal extract through solid phase column chromatography, ladder is carried out with cyclohexane-acetone mixed solvent
Degree elution, respectively obtains compound β-amyrin and compound cupreol；
(3) ethanol in above-mentioned steps (1) is extracted to the ethyl acetate portion obtained after the elution of medicinal extract chromatographic column, macroporous absorption tree is crossed
Fat post, carries out gradient elution with petroleum ether-ethyl acetate mixed solvent, respectively obtains the carbonic acid of compound 20 and 6- hydroxyls -2-
[[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl-β-D glucosides；
The concrete operations of the step (2) are as follows：Ethyl acetate obtained by step (1) is extracted into medicinal extract through solid phase column chromatography, with ring
Hexane-acetone mixed solvent carries out gradient elution, and gradient elution mixed solvent cyclohexane, the volume ratio of acetone are followed successively by 30:
1、25:1、20:1、15:1、10:1 and 5:1；It is 30 to collect both volume ratios:1、25:1、20:1 eluted fraction, revolving is removed
Solvent, dries, obtains compound β-amyrin；It is 15 to collect both volume ratios:1、10:1 and 5:1 eluted fraction, revolving
Solvent is removed, dries, obtains compound cupreol；
The concrete operations of the step (3) are as follows：Ethanol in above-mentioned steps (1) is extracted to the second obtained after the elution of medicinal extract chromatographic column
Acetoacetic ester part, crosses large pore resin absorption column, and gradient elution is carried out with petroleum ether-ethyl acetate mixed solvent, and gradient elution is mixed
Bonding solvent petrochina ether, the volume ratio of ethyl acetate are followed successively by 25:1、20:1、15:1、10:1 and 5:1, collect 25:1 and 20:1
Eluted fraction, revolving remove solvent, be dried to obtain the carbonic acid of compound 20；Collect 15:1、10:1 and 5:1 eluted fraction,
Revolving remove solvent, be dried to obtain 6- hydroxyls -2- [[[(1- hydroxyl -6- oxo -2- cyclohexenyl groups) carbonyl] oxygen] methyl] phenyl -
β-D glucosides；
Macroporous absorbent resin in the step (3) is D101 resins.
2. the method as described in claim 1, it is characterised in that：Solid phase column in the step (2) is neutral alumina column.
3. method as claimed in claim 2, it is characterised in that：The granularity of the neutral alumina is 100-500 mesh.
4. method as claimed in claim 3, it is characterised in that：The granularity of the neutral alumina is 100-200 mesh.
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