CN101830892B - Method for separating glycoside chemical components from tibetan capillaris - Google Patents
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- 239000000126 substance Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 21
- 229930182470 glycoside Natural products 0.000 title claims abstract description 20
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 20
- 239000000284 extract Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011347 resin Substances 0.000 claims abstract description 7
- 229920005989 resin Polymers 0.000 claims abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 83
- 235000019441 ethanol Nutrition 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 238000000605 extraction Methods 0.000 claims description 19
- 239000012074 organic phase Substances 0.000 claims description 17
- 239000007864 aqueous solution Substances 0.000 claims description 16
- AEDDIBAIWPIIBD-ZJKJAXBQSA-N mangiferin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(OC=2C(=CC(O)=C(O)C=2)C2=O)C2=C1O AEDDIBAIWPIIBD-ZJKJAXBQSA-N 0.000 claims description 16
- 239000012452 mother liquor Substances 0.000 claims description 16
- 244000144992 flock Species 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- YWQSXCGKJDUYTL-UHFFFAOYSA-N Mangiferin Natural products CC(CCC=C(C)C)C1CC(C)C2C3CCC4C(C)(C)CCCC45CC35CCC12C YWQSXCGKJDUYTL-UHFFFAOYSA-N 0.000 claims description 8
- 229940043357 mangiferin Drugs 0.000 claims description 8
- HEYZWPRKKUGDCR-QBXMEVCASA-N Swertiamarin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](C=C)[C@]2(O)CCOC(=O)C2=CO1 HEYZWPRKKUGDCR-QBXMEVCASA-N 0.000 claims description 6
- HEYZWPRKKUGDCR-WRMJXEAJSA-N Swertiamarin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@H]1[C@@H](C=C)[C@@]2(O)C(C(=O)OCC2)=CO1 HEYZWPRKKUGDCR-WRMJXEAJSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- DUAGQYUORDTXOR-GPQRQXLASA-N Gentiopicrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](C=C)C2=CCOC(=O)C2=CO1 DUAGQYUORDTXOR-GPQRQXLASA-N 0.000 claims description 5
- DUAGQYUORDTXOR-WULZUDSJSA-N Gentiopicrin Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@H]1[C@@H](C=C)C=2C(C(=O)OCC=2)=CO1 DUAGQYUORDTXOR-WULZUDSJSA-N 0.000 claims description 5
- 229960001701 chloroform Drugs 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 3
- 229960002246 beta-d-glucopyranose Drugs 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 2
- 238000011026 diafiltration Methods 0.000 claims description 2
- 239000012259 ether extract Substances 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 239000003814 drug Substances 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract description 5
- 238000004440 column chromatography Methods 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 238000011160 research Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 9
- 239000000470 constituent Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 229930003944 flavone Natural products 0.000 description 4
- 150000002213 flavones Chemical class 0.000 description 4
- 235000011949 flavones Nutrition 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000005325 percolation Methods 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 2
- VSJGJMKGNMDJCI-ZASXJUAOSA-N Sweroside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](C=C)[C@H](CCOC2=O)C2=CO1 VSJGJMKGNMDJCI-ZASXJUAOSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- VSJGJMKGNMDJCI-QXSNVGMTSA-N sweroside Natural products OC[C@H]1O[C@H](O[C@@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)[C@H](O)[C@@H](O)[C@@H]1O VSJGJMKGNMDJCI-QXSNVGMTSA-N 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- AEDDIBAIWPIIBD-LCQCTIQXSA-N OC[C@H]([C@@H]([C@@H](C1O)O)O)OC1c(c(O)c(c(Oc(c1c2)cc(O)c2O)c2)C1=O)c2O Chemical compound OC[C@H]([C@@H]([C@@H](C1O)O)O)OC1c(c(O)c(c(Oc(c1c2)cc(O)c2O)c2)C1=O)c2O AEDDIBAIWPIIBD-LCQCTIQXSA-N 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- XMHIUKTWLZUKEX-UHFFFAOYSA-N hexacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O XMHIUKTWLZUKEX-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a method for separating glycoside chemical components from tibetan capillaries, comprising three steps of extracting water solution of an tibetan capillaries extract, extracting and crudely separating according to the polarity gradient and separating and purifying by column chromatography. The invention has important significance on the study of the pharmacological effects of the tibetan capillaries and the research and the production of medicines thereof. By using the method, chemical components are separated into component groups with larger polarity difference, macroporous resin of the glycoside chemical components is separated and the cost is lower in comparison with the column chromatography separation for an extract at the later stage.
Description
Technical field
The present invention relates to a kind of extracting method of ZANGYINCHEN composition, more specifically relate to a kind of method of separating glycoside chemical components from tibetan capillaris.
Technical background
ZANGYINCHEN is one of traditional herbal medicine of commonly using of the ground Tibetan medicines such as Tibet, Qinghai, Sichuan, Yunnan and Gansu, is used for very early liver and gall diseases, especially enjoys great prestige China and foreign countries with treatment Acute Hepatic Yan Di and Huang Di, two legendary rulers of remote antiquity's subcutaneous ulcer.And it is comparatively backward for the research of chemical composition in ZANGYINCHEN.
(patent No.: 92108809.4) disclose a kind of production method of extraction process, equipment and ZANGYINCHEN tablet of ZANGYINCHEN effective constituent, be raw material with the ZANGYINCHEN grass to Chinese invention patent, and ethanol is extraction agent.Abstraction process production feature is that extract powder is 45～90% continuously, and auxiliary material is 10～55% ZANGYINCHEN tablet; Chinese invention patent (patent No.: 200710061832.4) disclose a kind of by extraction, removal of impurities, concentrated, initial gross separation, fractionation by adsorption, concentrated, dry, pulverize, the further extracting method of the ZANGYINCHEN effective constituent that is prepared from of the technique such as refining, adopt and extract aqueous solvent, extraction using alcohol, the ethanol recoverable, free from environmental pollution; Ultrasonic assisted extraction can shorten extraction time, improves extraction efficiency, reduces energy consumption; Adopt the processing such as centrifugal, macroporous resin adsorption can keep effective constituent, remove to greatest extent impurity, Chinese medicine is made essence, done carefully, reduce taking dose, can be processed into easily multiple formulation; Chinese invention patent (the patent No.: 200710163097.8) disclose a kind of ZANGYINCHEN extract, comprise swertiamarin, gentiopicrin, sweroside, Mangiferin, Lutonaretin, the mass ratio of described five kinds of compositions is (0.04～0.71): (20～40): (1～15): (1.6～26): (0.01～0.16); (application number: 200910078578.8) disclose a kind of ZANGYINCHEN extract, wherein contained at least total flavones, take this ZANGYINCHEN extract gross weight as 100%, this total flavones accounts for 20～75% of this ZANGYINCHEN extract to Chinese invention patent application.But above-mentioned ZANGYINCHEN extracting method only relates to the extraction of ZANGYINCHEN medicinal extract.And for the extracting method of chemical composition in ZANGYINCHEN, report is arranged seldom.(patent No.: 92108809.4) disclose a kind of production method of extraction process, equipment and ZANGYINCHEN tablet of ZANGYINCHEN effective constituent, be raw material with the ZANGYINCHEN grass to Chinese invention patent, and ethanol is extraction agent.Abstraction process production feature is that extract powder is 45～90% continuously, and auxiliary material is 10～55% ZANGYINCHEN tablet; Chinese invention patent (patent No.: 200710061832.4) disclose a kind of by extraction, removal of impurities, concentrated, initial gross separation, fractionation by adsorption, concentrated, dry, pulverize, the further extracting method of the ZANGYINCHEN effective constituent that is prepared from of the technique such as refining, adopt and extract aqueous solvent, extraction using alcohol, the ethanol recoverable, free from environmental pollution; Ultrasonic assisted extraction can shorten extraction time, improves extraction efficiency, reduces energy consumption; Adopt the processing such as centrifugal, macroporous resin adsorption can keep effective constituent, remove to greatest extent impurity, Chinese medicine is made essence, done carefully, reduce taking dose, can be processed into easily multiple formulation; Chinese invention patent (the patent No.: 200710163097.8) disclose a kind of ZANGYINCHEN extract, comprise swertiamarin, gentiopicrin, sweroside, Mangiferin, Lutonaretin, the mass ratio of described five kinds of compositions is (0.04～0.71): (20～40): (1～15): (1.6～26): (0.01～0.16); (application number: 200910078578.8) disclose a kind of ZANGYINCHEN extract, wherein contained at least total flavones, take this ZANGYINCHEN extract gross weight as 100%, this total flavones accounts for 20～75% of this ZANGYINCHEN extract to Chinese invention patent application.But above-mentioned ZANGYINCHEN extracting method only relates to the extraction of ZANGYINCHEN medicinal extract.
Summary of the invention
In order to address the above problem, the invention provides a kind of method of separating glycoside chemical components from tibetan capillaris, comprise the following steps:
1) obtain the ZANGYINCHEN extract aqueous solution;
2) one or more organic solvents in employing trichloromethane, tetrachloromethane, methylene dichloride, ether or ethyl acetate extract the ZANGYINCHEN extract aqueous solution and obtain mother liquor I and organic phase I, adopt propyl carbinol that mother liquor I is extracted and obtain mother liquor II and organic phase II, reclaim under reduced pressure organic phase I obtains into grouping I and becomes grouping II with organic phase II.
3) adopting temperature is that 15～85 ℃ of ethanol or dissolve with methanol become grouping II, cooling, separates out faint yellow flocks, filters flocks and obtains faint yellow mother liquor, adopts the faint yellow flocks of ethyl alcohol recrystallization to obtain Mangiferin;
4) faint yellow mother liquor is reclaimed ethanol to dried, the water dissolved residue, with aqueous solution loading D101 macroporous resin, the ethanol of water and concentration 〉=5% or methyl alcohol gradient elution obtain respectively each glycoside chemical components;
5) concentrated every section elutriant, obtain each glycoside chemical components.
Described step 3) the Mangiferin structural formula that obtains is as follows:
The glycoside chemical components that step 5 obtains comprises:
Gentiopicrin: structural formula is as follows:
Swertiamarin: structural formula is as follows:
8-O-[β-D-xylopyranose-(1-6)-β-D-Glucopyranose]-1,7-dihydroxyl-3-methoxyl group
Ketone, its structural formula is as follows:
The described extraction ZANGYINCHEN extract aqueous solution is: use respectively the same medicinal material of diafiltration of 90% ethanol, 60% ethanol, 30% second alcohol and water, merge above-mentioned percolate, be recycled to without alcohol residue, obtain the ZANGYINCHEN extract aqueous solution.
Useful technique effect of the present invention is: the present invention isolates the sterling of glycoside chemical components in ZANGYINCHEN, has great importance for the pharmacological action of investigating ZANGYINCHEN and the research and development production of medicine.Chemical composition is separated into the grouping of the larger one-tenth of several polarity differences, glycoside chemical components is carried out column chromatography for separation, shorter as the column chromatography for separation upper prop time in later stage on the medicinal extract extract, cost is lower.
Embodiment
Embodiment 1
Take 20kg ZANGYINCHEN medicinal material, oven dry is pulverized, and infiltrates with 90% ethanol and swells, and is filled in the diacolation bucket of diameter 20cm; Soak after 6 hours, with the speed of per minute 1～2mL, the beginning diacolation receives 3 times of volumes, obtains 90% ethanol percolation liquid; Add 60% ethanol in the diacolation bucket, soak after 6 hours, with the speed of per minute 1～2mL, the beginning diacolation receives 3 times of volumes, obtains 60% ethanol percolation liquid; Add 30% ethanol in the diacolation bucket, soak after 6 hours, with the speed of per minute 1～2mL, the beginning diacolation receives 3 times of volumes, obtains 30% ethanol percolation liquid; Add water in the diacolation bucket, soak after 6 hours, with the speed of per minute 1～2mL, the beginning diacolation receives 3 times of volumes, obtains the water percolate.
Respectively above-mentioned ethanol percolation liquid and water percolate reclaim under reduced pressure to nothing alcohol are distinguished the flavor of, merge, obtain the ZANGYINCHEN extract aqueous solution.
Adopt a kind of in trichloromethane, methylene dichloride that the ZANGYINCHEN extract aqueous solution is extracted with organic phase: the volume ratio of the ZANGYINCHEN extract aqueous solution=1: 3 adds organic phase, the extraction ZANGYINCHEN extract aqueous solution, viscosity and water with the ZANGYINCHEN extract aqueous solution are close to the investigation standard, determine concrete extraction times, obtain mother liquor I and organic phase I; Adopting chloroform in room temperature during higher than 25 ℃ is organic phase, and adopting methylene dichloride in room temperature during lower than 25 ℃ is organic phase.
Adopt propyl carbinol that the mother liquor I is extracted, with organic phase: the ratio of mother liquor I=1: 3 adds organic phase, and the extracting mother liquid I take the rate of transform of swertiamarin 〉=95% as the investigation standard, but must extract more than 3 times, determines concrete extraction times; Obtain mother liquor II and organic phase II.
Reclaim under reduced pressure organic phase II obtains into the grouping II respectively.
Adopting temperature is that 15～85 ℃ of ethanol or dissolve with methanol become the grouping II, cooling, separates out faint yellow flocks, filters flocks and obtains faint yellow mother liquor, and the faint yellow flocks of ethyl alcohol recrystallization obtains Mangiferin;
Faint yellow mother liquor is reclaimed ethanol to dried, the water dissolved residue, with aqueous solution loading D101 macroporous resin column (10*80cm), the ethanol of water and concentration 〉=5% or methyl alcohol gradient elution obtain respectively each glycoside chemical components;
Concentrated every section elutriant obtains each glycoside chemical components.
Embodiment 2
Take west, 20kg river Herba Swertiae bimaculatae medicinal material, extracting method is identical with embodiment 1.
The glycoside singulation that obtains from the D101 macroporous resin column is separated studies and is divided into a following 1-3 glycoside chemical components:
1, gentiopicrin: structural formula is as follows:
mp.191.9℃～193.8℃；UVλ
MeOHnm?212.2、243.9、276.9；
1H-NMR(400MHz，DMSO-d
6)δ：7.40(1H，d，J＝1Hz，3-H)，5.70(1H，m，6-H)，5.57(1H，d，J＝3Hz，1-H)，5.62(1H，m，8-H)，5.19(2H，m，9-H)；
13C-NMR(400MHz，DMSO-d
6)δ：96.5(C-1)，148.3(C-3)，103.3(C-4)，125.0(C-5)，116.0(C-6)，69.9(C-7)，133.9(C-8)，44.4(C-9)，117.7(C-10)，162.7(C-11)，98.8(C-1`)，72.7(C-2)，76.5(C-3`)，69.1(C-4`)，77.2(C-5`)，61.0(C-6`)。
2, swertiamarin: structural formula is as follows:
UVλ
MeOHnm?247.5；IRv
KBrcm
-13390.2，1694.1，1618.4；
1H-NMR(400MHz，DMSO-d
6)δ：7.55(1H，s，3-H)；
(5.62 1H, d, 1-H); (5.26 2H, t, 8-H); (4.46 d, J=8Hz, 1-H); (2.84 1H, t, 9-H); (1.69 2H, m, 6-H); 5.26 and 5.41 (1H, t, 10-H)
13C-NMR (100MHz, DMSO-d
6) δ: 96.39 (C1), 151.85 (C3), 108.06 (C4), 62.42 (C5), 31.99 (C6), 64.03 (C7), 132.78 (C8), 49.82 (C9), 120.28 (C10), 164.32 (C11), 98.20 (C1 '), 72.80 (C2 '), 76.00 (C3 '), 69.90 (C4 '), 77.35 (C5 '), 60.83 (C6 ').
3,8-O-[β-D-xylopyranose-(1-6)-β-D-Glucopyranose]-1,7-dihydroxyl-3-methoxyl group san ketone, molecular formula is C16H14O6, its structural formula is as follows:
FAB-MSm/z：[M+H]
+553。UVλ
max cH3OHnm：234.9，260.9，328.6。IRv
KBrcm
-1?3419.6、2976.0、2925.8、1662.5、1637.5、1606.6、1504.4、1463.9、1296.1、1276.8、1238.2、、1155.3、1130.2、1080.1、1047.3、983.6、812.0、586.3、536.1；13C-NMR(100MHz，DMSO-d
6)δ：184.1(C-9)，167.1(C-3)，161.6(C-1)，157.5(C-4a)，150.2(C-8)，150.0(C-4b)，139.0(C-7)，126.3(C-6)，107.4(C-8a)，105.8(C-5)，101.7(C-8b)，97.3(C-2)，92.9(C-4)，56.2(3-OCH3)。Glu：δ：99.9(C-1″)，69.3(C-2″)，70.3(C-3″)，71.8(C-4″)，68.3(C-5″)，17.7(C-6″)。Xyl：δ：100.3(C-1′)，76.9(C-2′)，76.3(C-3′)，70.3(C-4′)，65.5(C-5′)。
1H-NMR (400MHz, DMSO-d
6) δ: 11.84,11.75 (each 1H, s, 1,7-OH), 7.54 (1H, d, J=9.2Hz, 6-H), 6.96 (1H, d, J=9.2Hz, 5-H), 6.62 (1H, d, J=2.4Hz, 2-H), 6.40 (1H, d, J=2.0Hz, 4-H), 3.88 (3H, s, 3-OMe).Glu：：5.07(1H，d，J＝7.6Hz，1″-H)，1.07(3H，d，J＝7.6Hz，6″-H)。Xyl：5.15(1H，s，1′-H)。3.11～3.91(9H，m)；
4, Mangiferin: structural formula is as follows:
Mp.268.5-271.8 ℃ of carbonization; UV λ
MeOHNm 213.8,257.4,319.0,363.1; IRv
KRrcm
-13367.5,3215.1,3203.5,1649.0,1622.0,1595.0,1521.7,1492.8,1463.9,1296.1,1255.6,1199.6,1095.5,1076.2,1051.1,1031.8,827.4,588.2,520.7; EI-MS 425,404,385,368,350,329,330,274,273,256,245,219,203,200,185,153,123,100,95,83,69,55;
1H-NMR (400MHz, DMSO-d
6) δ: 6.35 (1H, s, 4-H), 6.89 (1H, S, 6-H), 7.44 (1H, s, H-8), 4.91 (1H, d, J=10Hz, 1-H).
Extract the chemical composition that obtains as follows from become the grouping I:
NSC 4205: C
16H
14O
6Structural formula is as follows:
mp.88.1-89.4℃；IRv/cm
-1：2954，1705，1473，1298，729。1H-NMR(400MHz，CDCl
3)δ：2.35?(2H，t，J＝7.2Hz)，1.62(2H，m)，1.25(44H，brs)，0.88(3H，t，J＝6.4Hz)，13C-NMR(400MHz，CDCl
3)δ：181.8(C-1)，33.4(C-2)，31.9(C-3)，29.7～29.1(C-4～C-23)，24.7(C-24)，22.7(C-25)，14.1(C-26)。
Claims (2)
1. the method for a separating glycoside chemical components from tibetan capillaris is characterized in that: comprise the following steps:
1) adopt the diacolation method to obtain the ZANGYINCHEN extract aqueous solution;
2) one or more in employing trichloromethane, tetrachloromethane, methylene dichloride, ether or ethyl acetate extract the ZANGYINCHEN extract aqueous solution and obtain mother liquor I and organic phase I, adopt propyl carbinol that the mother liquor I is extracted and obtain mother liquor II and organic phase II, reclaim under reduced pressure organic phase I obtains into the grouping I and becomes grouping II with organic phase II;
3) adopting temperature is that 15～85 ℃ of ethanol or dissolve with methanol become grouping II, cooling, separates out faint yellow flocks, filters flocks and obtains faint yellow mother liquor, adopts the faint yellow flocks of ethyl alcohol recrystallization to obtain Mangiferin;
4) faint yellow mother liquor is reclaimed ethanol to doing, the water dissolved residue is with aqueous solution loading D
101Macroporous resin, ethanol or the methyl alcohol gradient elution of water and Nong Du＞=5% obtain respectively each glycoside chemical components;
5) concentrated every section elutriant, obtain each glycoside chemical components;
The Mangiferin structural formula that described step 3) obtains is as follows:
The glycoside chemical components that step 5 obtains comprises:
Gentiopicrin: structural formula is as follows:
Swertiamarin: structural formula is as follows:
8-O-[β-D-xylopyranose-(1-6)-β-D-Glucopyranose]-1,7-dihydroxyl-3-methoxyl group
Ketone, its structural formula is as follows:
2. the method for separating glycoside chemical components from tibetan capillaris according to claim 1, it is characterized in that: the described extraction ZANGYINCHEN extract aqueous solution is: the same medicinal material of diafiltration of using respectively 90% ethanol, 60% ethanol, 30% second alcohol and water, merge above-mentioned percolate, be recycled to without alcohol residue, obtain the ZANGYINCHEN extract aqueous solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010176093 CN101830892B (en) | 2010-05-19 | 2010-05-19 | Method for separating glycoside chemical components from tibetan capillaris |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010176093 CN101830892B (en) | 2010-05-19 | 2010-05-19 | Method for separating glycoside chemical components from tibetan capillaris |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101830892A CN101830892A (en) | 2010-09-15 |
| CN101830892B true CN101830892B (en) | 2013-05-15 |
Family
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| CN103845354A (en) * | 2012-11-30 | 2014-06-11 | 哈尔滨誉衡药业股份有限公司 | Pharmaceutical composition containing gentiopicroside and its preparation and use |
| CN103408602B (en) * | 2013-07-22 | 2016-01-20 | 中国科学院西北高原生物研究所 | A kind of method being separated preparation four kinds of glycoside chemical reference substances from ZANGYINCHEN |
| CN103408615B (en) * | 2013-07-22 | 2016-04-20 | 中国科学院西北高原生物研究所 | The preparation method of Herba Swertiae bimaculatae alcohol glycosides chemical reference substance in ZANGYINCHEN medicinal material |
| CN106543193B (en) * | 2016-11-14 | 2018-10-16 | 江西科技师范大学 | 3- (- 4 picoline of 3- acetyl group)-(Z) -5- ethylidene -8- hydroxyls -3,4,5,6- tetra- hydrogen-based -1H- pyrans simultaneously [3,4, c]-pyridine -1- ketone and preparation method thereof |
| CN112851727B (en) * | 2021-02-08 | 2022-10-21 | 西藏天虹科技股份有限责任公司 | Method for extracting swertiamarin |
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| CN1730027A (en) * | 2004-08-06 | 2006-02-08 | 青海普兰特药业有限公司 | Method for preparing anti-hepatitis active part from swertia main pharmaceutical plant |
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| 马丽娜，等.《大孔树脂分离纯化川西獐牙菜中环烯醚萜苷类和酮类成分的工艺研究》.《中草药》.2010,第41卷(第2期),227-231. * |
| 黄一平,等.《藏药印度獐牙菜提取工艺研究》.《中成药》.2008,第30卷(第2期),190-192. * |
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