CN108276466B - A method of preparing gypenoside LVI - Google Patents
A method of preparing gypenoside LVI Download PDFInfo
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- CN108276466B CN108276466B CN201810243250.6A CN201810243250A CN108276466B CN 108276466 B CN108276466 B CN 108276466B CN 201810243250 A CN201810243250 A CN 201810243250A CN 108276466 B CN108276466 B CN 108276466B
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- Prior art keywords
- damulin
- gynostemma
- chitosan
- silica gel
- gypenoside
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- TXEWRVNOAJOINC-UHFFFAOYSA-N ginsenoside Rb2 Natural products CC(=CCCC(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C3CCC4(C)C3C(O)CC5C6(C)CCC(OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(C)(C)C6CCC45C)C TXEWRVNOAJOINC-UHFFFAOYSA-N 0.000 title claims abstract description 28
- NZXNJMVGDPUWMR-UHFFFAOYSA-N gypenoside LVI Natural products CC(=CCCC(C)(OC1OC(COC2OCC(O)C(O)C2O)C(O)C(O)C1O)C3CCC4(C)C5CCC6C(C)(C)C(OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C(O)CC6(C)C5CC(O)C34C)C NZXNJMVGDPUWMR-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 19
- 240000006509 Gynostemma pentaphyllum Species 0.000 claims abstract description 53
- 235000002956 Gynostemma pentaphyllum Nutrition 0.000 claims abstract description 51
- 241000519324 Cardiospermum microcarpum Species 0.000 claims abstract description 15
- 238000000746 purification Methods 0.000 claims abstract description 15
- 238000000605 extraction Methods 0.000 claims abstract description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- 229920001661 Chitosan Polymers 0.000 claims description 21
- 229960000892 attapulgite Drugs 0.000 claims description 18
- 239000004927 clay Substances 0.000 claims description 18
- 229910052625 palygorskite Inorganic materials 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000007864 aqueous solution Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 15
- 239000000741 silica gel Substances 0.000 claims description 15
- 229910002027 silica gel Inorganic materials 0.000 claims description 15
- 229960001866 silicon dioxide Drugs 0.000 claims description 15
- 238000010828 elution Methods 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 11
- 239000000243 solution Substances 0.000 claims description 11
- 239000003480 eluent Substances 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000011068 loading method Methods 0.000 claims description 6
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 238000004108 freeze drying Methods 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 238000012856 packing Methods 0.000 claims description 3
- 239000011148 porous material Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- YHVZKDRAJHNHJX-UDBICBSZSA-N (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(2r,3r,5r,8r,9r,10r,12r,13r,14r,17s)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl)-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxym Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)C[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(=C)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O YHVZKDRAJHNHJX-UDBICBSZSA-N 0.000 abstract description 21
- YHVZKDRAJHNHJX-UHFFFAOYSA-N damulin B Natural products CC(C)=CCCC(=C)C1CCC(C2(CCC3C4(C)C)C)(C)C1C(O)CC2C3(C)CC(O)C4OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O YHVZKDRAJHNHJX-UHFFFAOYSA-N 0.000 abstract description 21
- BMSPHMYCTYOUPF-SNVBIOCGSA-N (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(2r,3r,5r,8r,9r,10r,12r,13r,14r,17s)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2e)-6-methylhepta-2,5-dien-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hyd Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)C[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4C(/C)=C/CC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O BMSPHMYCTYOUPF-SNVBIOCGSA-N 0.000 abstract description 20
- BMSPHMYCTYOUPF-HYIBBFQISA-N damulin A Natural products CC(=CCC=C(C)[C@H]1CC[C@]2(C)[C@@H]1[C@H](O)C[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@H]4CC[C@@]23C)C BMSPHMYCTYOUPF-HYIBBFQISA-N 0.000 abstract description 20
- 241000671596 Gynostemma cardiospermum Species 0.000 abstract description 14
- 239000002994 raw material Substances 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 5
- 239000007791 liquid phase Substances 0.000 description 17
- 238000010898 silica gel chromatography Methods 0.000 description 16
- 238000004587 chromatography analysis Methods 0.000 description 15
- LTJZMSTVPKBWKB-HGZKDYFJSA-N (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(2r,3r,5r,8r,9r,10r,12r,13r,14r,17s)-2,12-dihydroxy-17-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)C[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LTJZMSTVPKBWKB-HGZKDYFJSA-N 0.000 description 14
- 239000012071 phase Substances 0.000 description 12
- 239000012535 impurity Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 229930182490 saponin Natural products 0.000 description 5
- 150000007949 saponins Chemical class 0.000 description 5
- 235000017709 saponins Nutrition 0.000 description 5
- LTJZMSTVPKBWKB-XUYZQZLKSA-N (2s,3r,4s,5s,6r)-2-[(2r,3r,4s,5s,6r)-2-[[(2r,3r,5r,8r,9r,10r,12r,13r,14r,17s)-2,12-dihydroxy-17-[(2r)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)C[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LTJZMSTVPKBWKB-XUYZQZLKSA-N 0.000 description 4
- VENRSYBHHVDBDC-UHFFFAOYSA-N 2-[2-[[2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[6-methyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)OC4C(C(O)C(O)C(CO)O4)O)C(O)CC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O VENRSYBHHVDBDC-UHFFFAOYSA-N 0.000 description 4
- CYPYEPJSRSWKLA-UHFFFAOYSA-N Gypenoside XLVI Natural products CC(=CCCC(C)(OC1OC(CO)C(O)C(O)C1O)C2CCC3(C)C4CCC5C(C)(C)C(OC6OC(CO)C(O)C(O)C6OC7OC(CO)C(O)C(O)C7O)C(O)CC5(C)C4CC(O)C23C)C CYPYEPJSRSWKLA-UHFFFAOYSA-N 0.000 description 4
- LTJZMSTVPKBWKB-UHFFFAOYSA-N gypenoside LI Natural products CC(C)=CCCC(C)(O)C1CCC(C2(CCC3C4(C)C)C)(C)C1C(O)CC2C3(C)CC(O)C4OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O LTJZMSTVPKBWKB-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 210000003323 beak Anatomy 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 241000345998 Calamus manan Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 229930187479 gypenoside Natural products 0.000 description 2
- ZRBFCAALKKNCJG-UHFFFAOYSA-N gypenoside-XVII Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OC(CO)C(O)C(O)C1O ZRBFCAALKKNCJG-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 235000012950 rattan cane Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 206010007247 Carbuncle Diseases 0.000 description 1
- 241001355283 Cayratia Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000005577 Gastroenteritis Diseases 0.000 description 1
- 206010019799 Hepatitis viral Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 244000283207 Indigofera tinctoria Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- 208000004078 Snake Bites Diseases 0.000 description 1
- 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 1
- 208000025865 Ulcer Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- -1 flavone compound Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 235000008216 herbs Nutrition 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Plant Substances (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses a kind of methods for preparing gypenoside LVI, this method is to belong to but the heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv of different subgenus substitutes gynostemma pentaphylla Gynostemma pentaphyllum (Thunb.) Makino as raw material, a large amount of gypenoside LVI can be prepared with extraction separation and purification, XLVI, L, LI, damulin A and damulin B, gypenoside LVI, XLVI, L, LI, the content of damulin A and damulin B in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv leaf is in gynostemma pentaphylla Gynoste respectively 10-50 times of content in mmapentaphyllum (Thunb.) Makino leaf；And heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv is not commercialized, unrestrained field be nobody shows any interest in all over the fields, and cost can be ignored.
Description
Technical field
The invention belongs to biomedicine fields, and in particular to a method of prepare gypenoside LVI.
Background technique
Gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino also known as Herb Gynostemmae Pentaphylli, Radix Rhodiolae, Herba Gynostemmatis
Deng being the herbaceous perennial vine plant of Curcurbitaceae gynostemma pentaphyllum genus, be mainly grown in the area on the south the Qinling Mountains and the Changjiang river in China.
It makees edible wild herbs use first recorded in the herbal for Relief of Famines of the Ming Dynasty, starts for it to be used as medicine with the name of " Japanese Cayratia Herb " in Compendium of Material Medica.
" the strong pharmacy of China ": " tri- two-way of Tong Tiao, clearing heat and detoxicating, cough-relieving apophlegmatic.For chronic bronchitis, virus hepatitis, renal plevis kidney
Inflammation, gastroenteritis, diarrhea, hypertension, arteriosclerosis, hyperlipidemia, ulcerative carbuncle pyogenic infections, snake bite ".Main chemical compositions in gynostemma pentaphylla
For saponin(e and polysaccharide, in addition also contain a small amount of flavone compound, terpene, organic acid, protein, vitamin, fat, fiber
Equal ingredients and zinc, copper, magnesium, iron, manganese, selenium and other trace elements.Gynostemma pentaphylla has antitumor, hypoglycemic, anti-aging, anti-liver fiber
The pharmacological actions such as change, principle active component gypenoside excessive use is also without side-effects, thus in health food and novel
There is huge application prospect on drug research and development, is a kind of new medical and edible dual purpose plant resource.
The saponin constituent contained in gynostemma pentaphylla is numerous, study it is more, active preferably have gypenoside LVI, XLVI, L,
LI, damulin A (DamulinA) and damulin B (Damulin B).Wherein, gypenoside LVI, XLVI content is higher, other
Four kinds are the extremely low rare saponin(e of content (for the converted product of gypenoside LVI, XLVI).
Currently, gypenoside LVI, XLVI are obtained by raw material extraction separation and purification of gynostemma pentaphylla, gypenoside L, LI,
Damulin A and damulin B obtained using the gynostemma pentaphylla that is processed by heating as raw material extraction separation and purification (document:
Determination by UPLC-MS of four dammaranetype saponins from heat-processed
Gynostemma pentaphyllum；Bioscience,Biotechnology,andBiochemistry,2014；Vol.78,
No.2,311-316).Gypenoside LVI, XLVI, L, LI, damulin A and damulin B is prepared as raw material using gynostemma pentaphylla to exist
Two o'clock is insufficient:
First, gynostemma pentaphylla price is relatively high, at high cost.Since State Scientific and Technological Commission in 1986 in Spark Program strand
Indigo plant is classified as the first place of " rare traditional Chinese medicine " leaved for development, and the market price of gynostemma pentaphylla is just obvious to go up.
Second, it is very low not heat gypenoside L, LI, damulin A and damulin B in the gynostemma pentaphylla of processing, separates pure
It is big to change difficulty；Heating processing is bothersome, and gypenoside L, LI, the content of damulin A and damulin B and asynchronous increasing after heating
Add, acid extraction is difficult to control (above-mentioned citation can also embody this phenomenon).
Gynostemma pentaphyllum genus shares 2 subgenus, 13 kind of 2 mutation, and 2 subgenus are gynostemma pentaphylla subgenus, beak fruit rattan subgenus, above-mentioned gynostemma pentaphylla
Gynostemmapentaphyllum (Thunb.) Makino is one of gynostemma pentaphylla subgenus (document: gynostemma plant
Categorizing system and distribution, Acta Phytotaxonomica Sinica, 1995).Research invention, gynostemma plant all contain gynostemma pentaphylla soap substantially
Glycosides, and type is essentially identical, but the content difference of specific gypenoside is larger in the different plants of the category.Originate from Hu Beixi
The heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv in portion, Southern Shaanxi and Sichuan belongs to beak fruit rattan
Subgenus, being mainly characterized by fruit is capsule, and top is cracked along ventral suture when mature, has the 3 pieces of beak styles harbored, other features
It is then almost the same with gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino.Open strand is not yet had been reported that at present
Blue saponin(e LVI, XLVI, L, LI, damulin A, B are in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex
Content in Oliv is significantly higher than gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino.
Summary of the invention
It is an object of that present invention to provide a kind of methods for preparing gypenoside LVI.
Above-mentioned purpose is achieved through the following technical solutions:
Gypenoside LVI, XLVI, L, LI, damulin A and damulin B preparation method include the following steps:
Step S1 collects the leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv, dries in the shade,
With ethanol water heating and refluxing extraction, filtered through gauze, merging filtrate is concentrated into no alcohol taste；
The extracting solution for being concentrated into no alcohol taste is splined on D101 large pore resin absorption column by step S2, and it is 1 that resin path height, which compares:
10, sample resin accounts for resin total amount 1/10 is mixed, wet method dress post mixes resin loading；First with 30% ethyl alcohol of 10BV with 10BV/h's
Flow velocity elution removal of impurities, then eluted with 85% ethyl alcohol of 10BV with the flow velocity of 10BV/h, 3-10BV eluent is collected, no alcohol is concentrated into
Taste obtains total saposins aqueous solution；
Total saposins aqueous solution is adjusted pH value to 6.0, chitosan/attapulgite clay compound, room temperature is added by step S3
Stirring is stood, filtering, collects filtrate, adjusts pH value to neutrality, freeze-drying obtains purification total saposins powder；
Purification total saposins powder is splined on normal phase silicagel column by step S4, and silica gel diameter height compares for 1:10, is mixed sample silica gel and is accounted for silicon
The 1/10 of glue total amount, dry column-packing mix silica gel loading；Successively with two that volume ratio is 20:1:2,10:1:2,5:1:2,2:1:2
Chloromethanes/methanol/acetone mixed solvent elutes 10BV, 6BV, 5BV, 3BV with the flow-rate gradient elution of 12BV/h respectively；
It is dry to collect 20:1:2 methylene chloride/methanol/acetone elution 7-8BV, 9-10BV eluent concentration respectively by step S5
It is dry to obtain damulin B, damulin A；10:1:2 methylene chloride/methanol/acetone elution 3-4BV, 5-6BV eluent is collected respectively
Concentrate drying obtains gypenoside L, gypenoside LI；5:1:2 methylene chloride/methanol/acetone elution 4-5BV is collected to wash
De- liquid is concentrated and dried to obtain gypenoside XLVI；It is dense to collect 2:1:2 methylene chloride/methanol/acetone elution 2-3BV eluent
Contracting is dried to obtain gypenoside LVI.
Preferably, chitosan/attapulgite clay compound is the preparation method comprises the following steps: 1g chitosan is dissolved in 100mL mass fraction
To obtain chitosan sol in 1% aqueous acetic acid, 8g attapulgite clay is added into the colloidal sol, stirring at normal temperature 48h is quiet
Upper solution is poured out after setting 2h, 50 DEG C of residue drying, grinding, drying.
Preferably, step S1 ethanol water concentration expressed in percentage by volume is 75%.
Preferably, the solid-to-liquid ratio that step S1 is extracted is 1:20.
Preferably, 50g chitosan/attapulgite clay compound is added in 1L total saposins aqueous solution in step S3.
Preferably, step S3 is stirred for 24 hours after chitosan/attapulgite clay compound is added, and is filtered after standing 2h.
Preferably, step S3 hydrochloric acid and ammonium hydroxide adjust pH.
The technology of the present invention advantage:
1, the present invention is to belong to but the heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex of different subgenus
Gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino is as raw material for Oliv substitution, can be with extraction separation and purification system
It is standby to obtain a large amount of gypenoside LVI, XLVI, L, LI, damulin A and damulin B, gypenoside LVI, XLVI, L, LI, reach
The content difference of the wooden woods A and damulin B in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv leaf
It is 10-50 times of the content in gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino leaf；And heart seed strand
Blue Gynostemma cardiospermum Cogn.ex Oliv is not commercialized, and unrestrained field be nobody shows any interest in all over the fields, and cost can neglect
Slightly.
2, step S3 of the present invention refines total saposins aqueous solution with chitosan/attapulgite clay compound, effectively
The impurity in total saposins is reduced, subsequent normal phase silica gel column chromatography technique is greatlied simplify, product purity is high.
Detailed description of the invention
Fig. 1 is the efficient liquid phase chromatographic analysis spectrogram of step S2 total saposins aqueous solution；
Fig. 2 is the efficient liquid phase chromatographic analysis spectrogram that step S3 refines total saposins powder；
Fig. 3 is the efficient liquid phase chromatographic analysis spectrogram for the damulin B that silica gel chromatography obtains；
Fig. 4 is the efficient liquid phase chromatographic analysis spectrogram for the damulin A that silica gel chromatography obtains；
Fig. 5 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside L that silica gel chromatography obtains；
Fig. 6 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside LI that silica gel chromatography obtains；
Fig. 7 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside XLVI that silica gel chromatography obtains；
Fig. 8 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside LVI that silica gel chromatography obtains.
Specific embodiment
Essentiality content of the invention is specifically introduced below with reference to embodiment, but it will be appreciated by those skilled in the art that not
Protection scope of the present invention should be confined to these specific embodiments.
One, experimental material
The leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv is collected from Hubei Shiyan City room
County, the leaf of gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino make after drying in the shade collected from Hunan Shaoyang Suining
With.
Chitosan/attapulgite clay compound is the preparation method comprises the following steps: it is 1% that 1g chitosan, which is dissolved in 100mL mass fraction,
Chitosan sol is obtained in aqueous acetic acid, and 8g attapulgite clay, stirring at normal temperature 48h, after standing 2h are added into the colloidal sol
Upper solution is poured out, 50 DEG C of residue drying, grinding, drying.
Different concentration ethanol refers both to the ethanol water of different volumes percentage concentration.
Two, experimental method
1, the preparation of gypenoside LVI, XLVI, L, LI, damulin A and damulin B
Include the following steps:
Step S1 collects the leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv, dries in the shade,
The ethanol water heating and refluxing extraction for being 75% with concentration expressed in percentage by volume, solid-to-liquid ratio 1:20 are extracted 3 times, each 2h, gauze
Filtering, merging filtrate are concentrated into no alcohol taste；
The extracting solution for being concentrated into no alcohol taste is splined on D101 large pore resin absorption column by step S2, and it is 1 that resin path height, which compares:
10, sample resin accounts for resin total amount 1/10 is mixed, wet method dress post mixes resin loading；First with 30% ethyl alcohol of 10BV with 10BV/h's
Flow velocity elution removal of impurities, then eluted with 85% ethyl alcohol of 10BV with the flow velocity of 10BV/h, 3-10BV eluent is collected, no alcohol is concentrated into
Taste obtains total saposins aqueous solution；
It is compound that chitosan/attapulgite clay is added in total saposins aqueous solution salt acid for adjusting pH value to 6.0 by step S3
50g chitosan/attapulgite clay compound is added in object, 1L total saposins aqueous solution, and stirring for 24 hours, is filtered after standing 2h, collects filter
Liquid, ammonium hydroxide adjust pH value to neutrality, and freeze-drying obtains purification total saposins powder；
Purification total saposins powder is splined on normal phase silicagel column by step S4, and silica gel diameter height compares for 1:10, is mixed sample silica gel and is accounted for silicon
The 1/10 of glue total amount, dry column-packing, mix silica gel loading (purification total saposins powder dissolved with methanol after with mix sample silica gel and mix
It is even, dry, purification total saposins powder and the mass ratio 1:1 for mixing sample silica gel)；It is successively 20:1:2,10:1:2,5:1 with volume ratio:
2, methylene chloride/methanol/acetone mixed solvent of 2:1:2 is with the flow-rate gradient elution of 12BV/h, elute respectively 10BV, 6BV,
5BV,3BV；
It is dry to collect 20:1:2 methylene chloride/methanol/acetone elution 7-8BV, 9-10BV eluent concentration respectively by step S5
It is dry to obtain damulin B, damulin A；10:1:2 methylene chloride/methanol/acetone elution 3-4BV, 5-6BV eluent is collected respectively
Concentrate drying obtains gypenoside L, gypenoside LI；5:1:2 methylene chloride/methanol/acetone elution 4-5BV is collected to wash
De- liquid is concentrated and dried to obtain gypenoside XLVI；It is dense to collect 2:1:2 methylene chloride/methanol/acetone elution 2-3BV eluent
Contracting is dried to obtain gypenoside LVI.
2, efficient liquid phase chromatographic analysis condition
Chromatograph: LC-20ADXR high-pressure pump；SPD-M20A diode array ultraviolet-visible detector；CTO-20AC column
Incubator；CBM-20A system controller；SIL-20ACXR autosampler；
Chromatographic column: Agilent ZORBAX Extend-C18 (250mm × 4.6mm, 5 μm)；
Mobile phase A phase: water (contains 5/10000ths tetrahydrofurans)；
Mobile phase B phase: acetonitrile (contains 5/10000ths tetrahydrofurans)；
Elution program: 0-3min, 20%B phase；3-15min, 20% → 40%B phase；15-30min, 40% → 80%B phase；
Flow velocity: 1.0mL/min；
Column temperature: 30 DEG C；
Detection wavelength: 203nm；
Sample volume: 10 μ L.
Three, experimental result
It takes step S2 total saposins aqueous solution to dilute 5 times and is used as high performance liquid chromatography sample introduction solution, step S3 is taken to refine total soap
Glycosides powder uses the mobile phase of initial proportion to be dissolved into the solution of 0.5mg/mL as high performance liquid chromatography sample introduction solution.Fig. 1 is step
The efficient liquid phase chromatographic analysis spectrogram of rapid S2 total saposins aqueous solution, Fig. 2 are the high-efficient liquid phase color that step S3 refines total saposins powder
Spectrum analysis spectrogram.From Fig. 1,2 as it can be seen that total saposins aqueous solution complicated component obtained by step S2, step S3 refine impurity in total saposins
Ingredient greatly reduces, and illustrates that chitosan/attapulgite clay compound can the total soap of effective Adsorption under the conditions of 6.0 pH
Impurity component in glycosides aqueous solution.By removal of impurities, facilitate the technology difficulty for reducing subsequent silica gel column chromatography.
Purification total saposins obtained after step S4, S5 silica gel column chromatography separating purification gypenoside LVI, XLVI, L,
LI, damulin A and damulin B monomer.Fig. 3 is the efficient liquid phase chromatographic analysis spectrum for the damulin B that silica gel chromatography obtains
Figure, Fig. 4 are the efficient liquid phase chromatographic analysis spectrogram for the damulin A that silica gel chromatography obtains, and Fig. 5 is silica gel chromatography
The efficient liquid phase chromatographic analysis spectrogram of obtained gypenoside L, Fig. 6 are the gypenoside LI that silica gel chromatography obtains
Efficient liquid phase chromatographic analysis spectrogram, Fig. 7 is the high performance liquid chromatography of gypenoside XLVI that silica gel chromatography obtains
Analysis of spectra, Fig. 8 are the efficient liquid phase chromatographic analysis spectrogram for the gypenoside LVI that silica gel chromatography obtains.From Fig. 3-8
As it can be seen that gypenoside LVI, XLVI, L, LI, damulin A and damulin B purity are very high, 95% or more.By a silicon
Gypenoside LVI, XLVI, L, LI, damulin A and the damulin B of such high-purity can be prepared in plastic column chromatography, mainly
Have benefited from step S3 chitosan/attapulgite clay compound refining and edulcoration.
The present invention has the advantage that
The present invention is to belong to but the heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex of different subgenus
Gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino is as raw material for Oliv substitution, can be with extraction separation and purification system
It is standby to obtain a large amount of gypenoside LVI, XLVI, L, LI, damulin A and damulin B, gypenoside LVI, XLVI, L, LI, reach
The content difference of the wooden woods A and damulin B in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv leaf
It is 12,11,45,37,42,55 times of the content in gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino leaf
(dried leaf of two kinds of gynostemma pentaphylla, solid ratio 1:40, ultrasonic 40min, filtering, then with height directly operating method: are extracted with methanol
Effect liquid phase chromatogram method analyzes filtrate, according to the peak face of gypenoside LVI, XLVI, L, LI, damulin A and damulin B
Its content ratio in two kinds of filtrates is roughly calculated in product ratio)；And heart seed gynostemma pentaphylla Gynostemma cardiospermum
Cogn.ex Oliv is not commercialized, and unrestrained field be nobody shows any interest in all over the fields, and cost of material can be ignored.
Step S3 of the present invention refines total saposins aqueous solution with chitosan/attapulgite clay compound, effectively drops
Impurity in low total saposins, greatlies simplify subsequent normal phase silica gel column chromatography technique, and product purity is high.
Claims (6)
1. a kind of method for preparing gypenoside LVI, which comprises the steps of:
Step S1 collects heart seed gynostemma pentaphyllaGynostemma cardiospermumCogn. the leaf of ex Oliv, dries in the shade, and uses second
Alcohol solution heating and refluxing extraction, filtered through gauze, merging filtrate are concentrated into no alcohol taste；
The extracting solution for being concentrated into no alcohol taste is splined on D101 large pore resin absorption column by step S2, and resin path height compares for 1:10, is mixed
Sample resin accounts for the 1/10 of resin total amount, and wet method dress post mixes resin loading；First washed with 30% ethyl alcohol of 10BV with the flow velocity of 10BV/h
It removes miscellaneous, then is eluted with 85% ethyl alcohol of 10BV with the flow velocity of 10BV/h, collect 3-10BV eluent, be concentrated into no alcohol taste and obtain
Total saposins aqueous solution；
Total saposins aqueous solution is adjusted pH value to 6.0, chitosan/attapulgite clay compound is added, room temperature stirs by step S3
It mixes, stand, filter, collect filtrate, adjust pH value to neutrality, freeze-drying obtains purification total saposins powder；
Purification total saposins powder is splined on normal phase silicagel column by step S4, and silica gel diameter height compares for 1:10, and mixing sample silica gel, to account for silica gel total
The 1/10 of amount, dry column-packing mixes silica gel loading；It is successively the dichloromethane of 20:1:2,10:1:2,5:1:2,2:1:2 with volume ratio
Alkane/methanol/acetone mixed solvent elutes 10BV, 6BV, 5BV, 3BV with the flow-rate gradient elution of 12BV/h respectively；
Step S5 collects 2:1:2 methylene chloride/methanol/acetone elution 2-3BV eluent and is concentrated and dried to obtain gypenoside
LVI；
Wherein, chitosan/attapulgite clay compound is the preparation method comprises the following steps: it is 1% that 1g chitosan, which is dissolved in 100 mL mass fractions,
Aqueous acetic acid in obtain chitosan sol, into the colloidal sol be added 8g attapulgite clay, stirring at normal temperature 48h, stand 2h
Upper solution is poured out afterwards, 50 DEG C of residue drying, grinding, drying.
2. according to the method described in claim 1, it is characterized by: step S1 ethanol water concentration expressed in percentage by volume is 75%.
3. according to the method described in claim 2, it is characterized by: the solid-to-liquid ratio that step S1 is extracted is 1:20.
4. according to the method described in claim 1, it is characterized by: in step S3 1L total saposins aqueous solution be added 50g chitosan/
Attapulgite clay compound.
5. according to the method described in claim 4, it is characterized by: chitosan/attapulgite clay compound is added in step S3
After stir for 24 hours, stand 2h after filter.
6. according to the method described in claim 1, it is characterized by: step S3 hydrochloric acid and ammonium hydroxide adjust pH.
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| PCT/CN2018/093947 WO2019178980A1 (en) | 2018-03-23 | 2018-07-01 | Method for preparing gynostemma pentaphylla makino saponin lvi, xlvi, l, li, damulin a or damulin b |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN86104409A (en) * | 1986-06-25 | 1988-01-06 | 安康地区科学技术委员会 | The preparation method of total gypenosides |
| KR20030023232A (en) * | 2001-09-12 | 2003-03-19 | 주식회사 뉴젠팜 | Method of extracting saponin from Panax ginseng or Gynostemma pentaphyllum and foods containing the extracted saponin therefrom |
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| CN86104409A (en) * | 1986-06-25 | 1988-01-06 | 安康地区科学技术委员会 | The preparation method of total gypenosides |
| KR20030023232A (en) * | 2001-09-12 | 2003-03-19 | 주식회사 뉴젠팜 | Method of extracting saponin from Panax ginseng or Gynostemma pentaphyllum and foods containing the extracted saponin therefrom |
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