CN106420871A - Preparation method of Panax notoginseng saponins rich in Fe and Fd and monomers Fe and Fd thereof - Google Patents
Preparation method of Panax notoginseng saponins rich in Fe and Fd and monomers Fe and Fd thereof Download PDFInfo
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- CN106420871A CN106420871A CN201610862430.3A CN201610862430A CN106420871A CN 106420871 A CN106420871 A CN 106420871A CN 201610862430 A CN201610862430 A CN 201610862430A CN 106420871 A CN106420871 A CN 106420871A
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- ginsenoside
- ethanol water
- extracting solution
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000000178 monomer Substances 0.000 title claims abstract description 17
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title abstract 3
- MYBAONSAUGZRAX-UBQYYSLZSA-N Notoginsenoside Fe Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O MYBAONSAUGZRAX-UBQYYSLZSA-N 0.000 claims abstract description 45
- 241000180649 Panax notoginseng Species 0.000 claims abstract description 40
- 235000003143 Panax notoginseng Nutrition 0.000 claims abstract description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 26
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 19
- 229920005989 resin Polymers 0.000 claims abstract description 19
- 238000000605 extraction Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 244000131316 Panax pseudoginseng Species 0.000 claims description 19
- 235000003181 Panax pseudoginseng Nutrition 0.000 claims description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000741 silica gel Substances 0.000 claims description 11
- 229910002027 silica gel Inorganic materials 0.000 claims description 11
- 229960001866 silicon dioxide Drugs 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 239000003463 adsorbent Substances 0.000 claims description 9
- 230000000274 adsorptive effect Effects 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 8
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 claims description 6
- 239000012467 final product Substances 0.000 claims description 6
- 238000007654 immersion Methods 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 16
- 229930182490 saponin Natural products 0.000 abstract description 16
- 235000017709 saponins Nutrition 0.000 abstract description 16
- 150000007949 saponins Chemical class 0.000 abstract description 15
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 238000002791 soaking Methods 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- ZTQSADJAYQOCDD-HUGMCNGHSA-N (2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-[[(3s,5r,8r,9r,10r,12r,13r,14r,17s)-12-hydroxy-4,4,8,10,14-pentamethyl-17-[(2s)-6-methyl-2-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O ZTQSADJAYQOCDD-HUGMCNGHSA-N 0.000 abstract 2
- ZTQSADJAYQOCDD-XTHRNRJFSA-N Gypenoside IX Natural products O([C@](CC/C=C(\C)/C)(C)[C@@H]1[C@H]2[C@H](O)C[C@H]3[C@](C)([C@]2(C)CC1)CC[C@H]1C(C)(C)[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CC[C@]31C)[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@H](O)[C@H](O)[C@H](O)CO2)O1 ZTQSADJAYQOCDD-XTHRNRJFSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- LDCGQTUTAWJKFH-VKXLEPQWSA-N notoginsenoside-Fe Natural products O([C@](C/C=C/C(C)C)(C)[C@@H]1[C@H]2[C@H](O)C[C@H]3[C@](C)([C@]2(C)CC1)CC[C@H]1C(C)(C)[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)CC[C@]31C)[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O2)O1 LDCGQTUTAWJKFH-VKXLEPQWSA-N 0.000 abstract 2
- 229930189092 Notoginsenoside Natural products 0.000 abstract 1
- 239000011148 porous material Substances 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 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 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- PFSIGTQOILYIIU-UHFFFAOYSA-N ginsenoside Rb3 Natural products CC(=CCCC(C)(O)C1CCC2(C)C3CCC4C(C)(C)C(CCC4(C)C3CC(OC5OC(COC6OCC(O)C(O)C6O)C(O)C(O)C5O)C12C)OC7OC(CO)C(O)C(O)C7OC8OC(CO)C(O)C(O)C8O)C PFSIGTQOILYIIU-UHFFFAOYSA-N 0.000 description 10
- 238000001514 detection method Methods 0.000 description 8
- NODILNFGTFIURN-USYOXQFSSA-N ginsenoside Rb3 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1OC[C@@H](O)[C@H](O)[C@H]1O NODILNFGTFIURN-USYOXQFSSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YQKCHRBAJSATCG-UHFFFAOYSA-N UNPD30744 Natural products OC1C(O)C(O)C(C)OC1OCC1C(O)C(O)C(O)C(OC(C)(CCC=C(C)C)C2C3C(C4(CCC5C(C)(C)C(OC6C(C(O)C(O)C(CO)O6)OC6C(C(O)C(O)C(CO)O6)O)CCC5(C)C4CC3O)C)(C)CC2)O1 YQKCHRBAJSATCG-UHFFFAOYSA-N 0.000 description 6
- CNHRRMQBWQJRPN-UHFFFAOYSA-N chikusetsusaponin LM5 Natural products C1CC(C2(CC(O)C3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)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)C1O CNHRRMQBWQJRPN-UHFFFAOYSA-N 0.000 description 6
- 230000006837 decompression Effects 0.000 description 6
- 238000011010 flushing procedure Methods 0.000 description 6
- JDCPEKQWFDWQLI-LUQKBWBOSA-N ginsenoside Rc Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O JDCPEKQWFDWQLI-LUQKBWBOSA-N 0.000 description 6
- UVBLDLGZDSGCSN-UHFFFAOYSA-N ginsenoside-Rb3 Natural products C1=CC2C3(C)CCC(O)C(C)(C)C3CCC2(C)C2(C)CCC34CCC(C)C(C)C4C21OC3=O UVBLDLGZDSGCSN-UHFFFAOYSA-N 0.000 description 6
- SPFXZQZPHXUJSR-UHFFFAOYSA-N ginsenoside-Rc Natural products CC(=CCCC(C)(OC1OC(CO)C(O)C(O)C1OC2OC(CO)C(O)C2O)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 SPFXZQZPHXUJSR-UHFFFAOYSA-N 0.000 description 6
- 238000010829 isocratic elution Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- NODILNFGTFIURN-GZPRDHCNSA-N ginsenoside Rb2 Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O)O[C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)O[C@@H]1OC[C@H](O)[C@H](O)[C@H]1O NODILNFGTFIURN-GZPRDHCNSA-N 0.000 description 4
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 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)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 241001037751 Fusarium oxysporum f. sp. vanillae Species 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229930182494 ginsenoside Natural products 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- OORMXZNMRWBSTK-LGFJJATJSA-N dammarane Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@H]([C@H](C)CCCC(C)C)[C@H]4CC[C@@H]3[C@]21C OORMXZNMRWBSTK-LGFJJATJSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000002137 ultrasound extraction Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000208343 Panax Species 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940089161 ginsenoside Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- SYXUBXTYGFJFEH-UHFFFAOYSA-N oat triterpenoid saponin Chemical compound CNC1=CC=CC=C1C(=O)OC1C(C=O)(C)CC2C3(C(O3)CC3C4(CCC5C(C)(CO)C(OC6C(C(O)C(OC7C(C(O)C(O)C(CO)O7)O)CO6)OC6C(C(O)C(O)C(CO)O6)O)CCC53C)C)C4(C)CC(O)C2(C)C1 SYXUBXTYGFJFEH-UHFFFAOYSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Substances OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- -1 saponins compound Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/25—Araliaceae (Ginseng family), e.g. ivy, aralia, schefflera or tetrapanax
- A61K36/258—Panax (ginseng)
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Alternative & Traditional Medicine (AREA)
- Epidemiology (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Botany (AREA)
- Animal Behavior & Ethology (AREA)
- Biotechnology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Steroid Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention provides a preparation method of panax notoginseng saponins rich in Fe and Fd and monomers Fe and Fd thereof. The preparation method comprises the following steps of: (1) putting a panax notoginseng medicinal material in warm water, soaking the panax notoginseng for 10-200 minutes, and then adding an ethanol water solution or water for extraction to obtain an extracting solution, wherein the panax notoginseng medicinal material comprises panax notoginseng leaves and/or panax notoginseng flowers; and (2) enabling the extracting solution to pass a large pore resin absorption column, and eluting by using the ethanol water solution to obtain the panax notoginseng saponins rich in rare notoginsenoside Fe and Fd. The preparation method has the beneficial effects that the content of rare notoginsenoside Fe and Fd in the total saponins can be greatly increased, and meanwhile, the monomers Fe and Fd of the notoginsenoside can be obtained by a simple separation and purification method.
Description
Technical field
The invention belongs to natural drug preparing technical field, and in particular to a kind of Radix Notoginseng total arasaponinss rich in Fe, Fd and its
The preparation method of monomer Fe and Fd.
Background technology
Radix Notoginseng is the dry root of panax araliaceae plant [Panax notoginseng (Burk.) F.H.Chen], is China
Rare Chinese medicine, its principle active component is that saponins compound, Radix Notoginseng is many to be used as medicine with root or rhizome.Research finds that Folium Notoginseng has
Calm the nerves, blood pressure lowering, analgesia, antiinflammatory the effects such as, but its utilization rate only has 5%, and most of available resources is dropped.Folium Notoginseng and
Contain a large amount of dammarane type protopanaxadiol-type ginsenosides in flower of Radix Notoginseng, with ginsenoside Rb3、Rb2It is main component with Rc,
And the content of N-Fe Ginsenoside Mb and Fd is extremely low, therefore its pharmacological action report is also little.In order to develop further Folium Notoginseng/flower and
How rare ginsenoside, obtain the Radix Notoginseng total arasaponinss rich in N-Fe Ginsenoside Mb and Fd and quickly prepare arasaponin in a large number
Fe and Fd chemical monomer is current problem demanding prompt solution.
Content of the invention
In view of this, it is an object of the invention to provide a kind of Radix Notoginseng total arasaponinss rich in Fe, Fd and monomer Fe and Fd
Preparation method.The preparation method of the present invention can greatly improve the content of rare N-Fe Ginsenoside Mb and Fd in total saponins, while
N-Fe Ginsenoside Mb and the Fd monomer of high-load can be obtained by simple isolation and purification method.
To achieve these goals, the present invention provides a kind of Radix Notoginseng total arasaponinss rich in Fe, Fd and monomer Fe and Fd
Preparation method, comprises the steps：
(1) pseudo-ginseng is added in warm water and 10～200min is soaked, be subsequently adding ethanol water or water is extracted,
Extracting solution is obtained, wherein, the pseudo-ginseng includes Folium Notoginseng and/or flower of Radix Notoginseng；
(2) by macroporous adsorptive resins on extracting solution, use ethanol water eluting, obtain final product rich in rare N-Fe Ginsenoside Mb and
The Radix Notoginseng total arasaponinss of Fd.
Wherein, in step (1), the preferred powder pseudo-ginseng of the pseudo-ginseng, i.e., pseudo-ginseng powder, more preferably advises
Lattice are the pseudo-ginseng powder of 20～60 mesh.
Preferably 10～80 DEG C of the temperature of the warm water, more preferably 40～70 DEG C.
The time of the immersion preferably 30～90min.
During immersion, the pseudo-ginseng is preferably 1 with the mass volume ratio of warm water:1～1:10, herein, described quality
Volume ratio is the implication of this area routine, and its unit can be kg/L or g/mL, for example, 1kg pseudo-ginseng is soaked in 1L
The mass volume ratio of warm water is 1:1.
In step (1), the concentration of the ethanol water is that this area is conventional described, and its concentration can be 0～100%
(v/v) any, preferably 70～90%, the pseudo-ginseng is preferably 1 with the mass volume ratio of the ethanol water:1～1:
100, more preferably 1:20～1:25, herein, described mass volume ratio is the implication of this area routine, and its unit can be kg/L
Or g/mL, for example, the mass volume ratio that 1kg pseudo-ginseng is extracted with 1L ethanol water is 1:1.
In step (1), the operation for being extracted as this area routine, preferably seepage pressure effects, circumfluence distillation and ultrasound is carried
Any one in taking；The time of the extraction preferably 1～6h, more preferably 90～150min.
In step (2), before by macroporous adsorptive resins on extracting solution, further preferably the extracting solution is carried out reducing pressure dense
Contracting, afterwards by macroporous adsorptive resins on the extracting solution after concentration；If adding ethanol water in step (1) to be carried
Take, then after extracting solution described in preferred pair is evaporated to no alcohol taste, afterwards by macroporous absorption tree on the extracting solution after concentration
Fat post.
In step (2), the macroporous adsorbent resin preferred X-5, AB-8, DM-301, NK-2, NKA-2, NK-9, D-101 and
Any one in WLD.
In step (2), the use ethanol water eluting can be this area routine, it is preferable that be first with 0～20% (v/
V) ethanol water washing, discards washing liquid, then with 40～100% (v/v) ethanol water eluting, collects eluent.
In step (2), it is preferable that before with ethanol water eluting, it is colourless first to wash with water to effluent.
Preferably, in order to be obtained rare N-Fe Ginsenoside Mb and the Fd monomer of high-load, the total soap of the Radix Notoginseng rich in Fe, Fd
The preparation method of glycosides and monomer Fe and Fd also comprises the steps：
(3) Radix Notoginseng total arasaponinss rich in rare N-Fe Ginsenoside Mb and Fd of step (2) gained are adsorbed on silicagel column, point
Eluting is not carried out with chloroform-methanol and acetate-methanol, and Fractional Collections merges the stream part of N-Fe Ginsenoside Mb and Fd, reduces pressure back
Solvent is received to dry, that is, obtain the monomer of N-Fe Ginsenoside Mb and Fd.
Wherein, in the chloroform-methanol, preferably chloroform is 20 with the volume ratio of methanol:1～1:1；The ethyl acetate-
In methanol, ethyl acetate is 10 with the volume ratio of methanol:1～1:1.
In the present invention, above-mentioned optimum condition on the basis of common sense in the field is met can combination in any, obtain final product the present invention each
Preferred embodiments.
Raw material or reagent used by the present invention is in addition to special instruction, all commercially available.
The present invention achieves following beneficial effects：
Total saponins high income in the product for being obtained using the preparation method of the present invention, total saponin content is up to 84% (Rhizoma et radix valerianae
Aldehyde-perchloric acid UV method), the main composition containing N-Fe Ginsenoside Mb and Fd etc., and the enrichment degree and content of N-Fe Ginsenoside Mb and Fd is relatively
Height, wherein N-Fe Ginsenoside Mb content are up to 5.1% (HPLC method), and arasaponin Fd content is up to 8.8% (HPLC method), separated
The N-Fe Ginsenoside Mb for obtaining and Fd monomer purity are all more than 90%, it can be seen that the process efficiency of the present invention is high, time-consuming less, low
Cost, high efficiency, beneficial to industrialization high quality of production.
Description of the drawings
Fig. 1 is Folium Notoginseng methanolic extract (A) and water decoction (B) HPLC chromatogram, wherein 1-3 be Ginsenoside Rc,
Rb2And Rb3, 4-5 is N-Fe Ginsenoside Mb and Fd；
Fig. 2A and Fig. 2 B is impact result figure of the water soaking temperature to transformation efficiency；
Fig. 3 A and Fig. 3 B are impact result figure of the water-soaking time to transformation efficiency；
Fig. 4 is the concentrated solution (A) for processing without macroporous adsorbent resin in the embodiment of the present invention 1, and prepared is rich in
The HPLC figure of the Folium Notoginseng total arasaponins composition product (B) of rare N-Fe Ginsenoside Mb and Fd, wherein 1-3 is Ginsenoside Rc, Rb2
And Rb3, 4-5 is N-Fe Ginsenoside Mb and Fd；
Fig. 5 is isolated N-Fe Ginsenoside Mb (A) in the embodiment of the present invention 1 and arasaponin Fd (B) monomer HPLC color
Spectrogram.
Specific embodiment
For making the object, technical solutions and advantages of the present invention become more apparent, below in conjunction with specific embodiment, and reference
Accompanying drawing, the present invention is described in further detail.
In view of contain a large amount of dammarane type protopanaxadiol-type ginsenosides in Folium Notoginseng and flower of Radix Notoginseng, with ginsenoside
Rc、Rb2And Rb3For main component, and the content of N-Fe Ginsenoside Mb and Fd is extremely low, and therefore its pharmacological action report is also little.In order to
Strengthen the research for rare N-Fe Ginsenoside Mb and Fd, be necessary to improve first the content of rare N-Fe Ginsenoside Mb and Fd right in fact
Which is separated and is enriched with.Applicant is surprisingly had found during substantial amounts of Experimental Research, if carrying out alcohol to pseudo-ginseng
The immersion of certain time before carrying (or not extracted with alcohol), is first carried out with warm water to pseudo-ginseng, then contribute to Radix Notoginseng soap
The generation conversion of glycosides Fe and Fd, improves the content of rare N-Fe Ginsenoside Mb and Fd.Further, if pseudo-ginseng is crushed to one
Determine the powder of mesh number, and optimize temperature and the soak time of warm water, then Fe and Fd generates the efficiency of conversion and can improve further.
Applicant is obtained finally the experiment condition of the present invention, as a result shows through substantial amounts of explorative experiment and through experimental verification repeatedly,
Under the experiment parameter scope of the present invention, preferable effect can be all obtained.
Applicant is had found in early-stage Study, in Folium Notoginseng methanol or ethanol extraction, the content of N-Fe Ginsenoside Mb and Fd
Extremely low, in water decoction, the content of N-Fe Ginsenoside Mb and Fd increases, and Ginsenoside Rc and Rb3Content is correspondingly reduced,
As a result as shown in Figure 1.Further investigation revealed that, in the case of pure water, Ginsenoside Rc and Rb3In the presence of certain enzyme
Can hydrolysis be.Applicant has found, the efficiency of this conversion is with temperature through further research
Degree have larger dependency, through repeatedly experimental verification find 50 DEG C when transformation efficiency highest, and with temperature continue raise,
Then conversion ratio starts slowly to decline, and as a result asks for an interview Fig. 2A and Fig. 2 B.Meanwhile, applicant is also investigated to soak time, excellent
Soak time is changed, as a result as shown in Figure 3 A and Figure 3 B.
Embodiment 1
20g Folium Notoginseng is ground into 40 mesh powder, plus the water of 80mL is infiltrated 0.5 hour at 50 DEG C, is subsequently adding 400mL
70% alcohol reflux 60 minutes, collect extracting solution, filter, filtering residue is reclaimed, and continuously adds 70% alcohol reflux of 400mL
Extracting 60 minutes, united extraction liquid, relative density is evaporated to for 1.11；By D-101 type macroporous adsorbent resin on concentrated solution
Post, wherein macroporous adsorbent resin are 2 with the volume ratio of concentrated solution：1, post footpath is 1 with pillar height ratio:15, first wash with water to effluent
For colourless, then 20% alcohol flushing with 15 times of column volumes, flushing liquor is discarded, finally whole with ethanol that volume fraction is 60%
Eluting, collects eluent, and recycling design is to the dry Folium Notoginseng total arasaponins compositionss for obtaining final product rich in rare N-Fe Ginsenoside Mb and Fd
2.5g, checks through vanilla root rot UV method, and total saponins purity is 84%.Check through HPLC method, wherein N-Fe Ginsenoside Mb content
5.1%, arasaponin Fd content is 8.8%.In the present embodiment, without the concentrated solution (A) that macroporous adsorbent resin is processed, and pass through
Macroporous adsorbent resin processes the obtained HPLC rich in rare N-Fe Ginsenoside Mb and the Folium Notoginseng total arasaponins composition product (B) of Fd
Chromatogram is as shown in figure 4, wherein 1-3 is Ginsenoside Rc, Rb2And Rb3, 4-5 is N-Fe Ginsenoside Mb and Fd.
Obtained total saponins are adsorbed on the silica gel of 2 times amount, evaporate into dry, standby；Dress post, by 10 times amount of total saponins
Column chromatography silica gel, uses chloroform wet method dress post, uses eluent repeatedly, so that silica gel is fully sunk closely；Loading and eluting, by sample
Product are slowly added in chromatographic column, with chloroform-methanol (volume ratio 5:1) isocratic elution, Fractional Collections, it is 4 times per stream part collecting amount
Column volume, merges the stream part containing N-Fe Ginsenoside Mb and Fd after thin layer chromatography detection, and decompression and solvent recovery is to dry, then uses silica gel
Column chromatography, with acetate-methanol (volume ratio 5:1) isocratic elution, Fractional Collections, is 3 times of column volumes per stream part collecting amount,
Merge N-Fe Ginsenoside Mb and Fd stream part respectively after thin layer chromatography detection, decompression and solvent recovery obtains N-Fe Ginsenoside Mb to dry
54.6mg and Fd 56.7mg.HPLC detection purity is respectively 90.6% and 90.8%, isolated N-Fe Ginsenoside Mb (A) and three
The HPLC chromatogram of seven saponin Fd (B) monomers is as shown in Figure 5.
Embodiment 2
10g notogenseng pollen is broken into 50 mesh powder, plus 100mL water is infiltrated 1.5 hours at 40 DEG C, is subsequently adding 150mL
90% ethanol ultrasonic extraction 60 minutes, collects extracting solution, filters, and is evaporated to relative density for 1.15；By X-5 on concentrated solution
Type macroporous adsorptive resins, wherein macroporous adsorbent resin are 1.5 with the volume ratio of concentrated solution：1, post footpath is 1 with pillar height ratio:10,
It is colourless first to wash with water to effluent, then 20% alcohol flushing with 10 times of column volumes, discards flushing liquor, finally uses volume fraction
The whole eluting of ethanol for 70%, collect eluent, and recycling design is to the dry Radix Notoginseng for obtaining final product rich in rare N-Fe Ginsenoside Mb and Fd
Flower total saponine 2.02g, checks through vanilla root rot UV method, and total saponins purity is 64.7%.Check through HPLC method, wherein three
It is 7.16% that seven saponin Fe contents are 4.23%, arasaponin Fd content.
Obtained total saponins are adsorbed on the silica gel of 3 times amount, evaporate into dry, standby；Dress post, by 5 times amount of total saponins
Column chromatography silica gel, uses chloroform wet method dress post, uses eluent repeatedly, so that silica gel is fully sunk closely；Loading and eluting, by sample
Product are slowly added in chromatographic column, with chloroform-methanol (volume ratio 20:1) isocratic elution, Fractional Collections, it is 4 times per stream part collecting amount
Column volume, merges the stream part containing N-Fe Ginsenoside Mb and Fd after thin layer chromatography detection, and decompression and solvent recovery is to dry, then uses silica gel
Column chromatography, with acetate-methanol (volume ratio 3:1) isocratic elution, Fractional Collections, is 3 times of column volumes per stream part collecting amount,
Merge N-Fe Ginsenoside Mb and Fd stream part respectively after detecting through thin layer chromatography, decompression and solvent recovery to obtain N-Fe Ginsenoside Mb to dry
21.0mg and Fd 23.4mg.HPLC detection purity is respectively 82.1% and 73.5%.
Embodiment 3
15g Folium Notoginseng is ground into 60 mesh powder, plus 90mL water is infiltrated 0.5 hour at 70 DEG C, is subsequently adding 150mL
80% ethanol ultrasonic extraction 30 minutes, collects extracting solution, filters, and filtering residue is reclaimed, and is evaporated to relative density for 1.08；Will be dense
DM-301 type macroporous adsorptive resins on contracting liquid, wherein macroporous adsorbent resin are 1 with the volume ratio of concentrated solution：2, post footpath and pillar height
Than for 1:12, it is colourless first to wash with water to effluent, then 10% alcohol flushing with 10 times of column volumes, discards flushing liquor, finally
With the whole eluting of ethanol that volume fraction is 80%, eluent is collected, recycling design is obtained final product rich in rare N-Fe Ginsenoside Mb to dry
With the Folium Notoginseng total arasaponins 3.10g of Fd, check through vanilla root rot UV method, total saponins purity is 41.0%.Examine through HPLC method
Look into, wherein N-Fe Ginsenoside Mb content 4.24%, arasaponin Fd content 8.24%.
Obtained total saponins are adsorbed on the silica gel of 5 times amount, evaporate into dry, standby；Dress post, by 15 times amount of total saponins
Column chromatography silica gel, uses chloroform wet method dress post, uses eluent repeatedly, so that silica gel is fully sunk closely；Loading and eluting, by sample
Product are slowly added in chromatographic column, with chloroform-methanol (volume ratio 15:1) isocratic elution, Fractional Collections, it is 4 times per stream part collecting amount
Column volume, merges the stream part containing N-Fe Ginsenoside Mb and Fd after thin layer chromatography detection, and decompression and solvent recovery is to dry, then uses silica gel
Column chromatography, with acetate-methanol (volume ratio 10:1) isocratic elution, Fractional Collections, is 3 times of cylinders per stream part collecting amount
Product, merges arasaponin Fd and Fe stream part after thin layer chromatography detection respectively, and decompression and solvent recovery obtains N-Fe Ginsenoside Mb to dry
18.3mg and Fd 20.1mg.HPLC detection purity is respectively 81.3% and 70.6%.
When above-described embodiment only lists the condition that part is applied to technical solution of the present invention, the such as temperature of warm water, immersion
Between etc., in fact, in the range of claims of the present invention protection, can all obtain preferable effect, that is, compare existing
Technology increases substantially the content of Fe and Fd in Radix Notoginseng total arasaponinss, and here is not thin one by one to lift.
Particular embodiments described above, has been carried out to the purpose of the present invention, technical scheme and beneficial effect further in detail
Describe in detail bright, it should be understood that the foregoing is only the specific embodiment of the present invention, be not limited to the present invention, all
Within the spirit and principles in the present invention, any modification, equivalent substitution and improvement that is done etc., should be included in the protection of the present invention
Within the scope of.
Claims (10)
1. the preparation method of a kind of Radix Notoginseng total arasaponinss rich in Fe, Fd and monomer Fe and Fd, it is characterised in that walk including following
Suddenly：
(1) pseudo-ginseng is added in warm water and 10～200min is soaked, be subsequently adding ethanol water or water is extracted, obtain
Extracting solution, wherein, the pseudo-ginseng includes Folium Notoginseng and/or flower of Radix Notoginseng；
(2) by macroporous adsorptive resins on extracting solution, ethanol water eluting is used, obtains final product rich in rare N-Fe Ginsenoside Mb and Fd
Radix Notoginseng total arasaponinss.
2. preparation method according to claim 1, it is characterised in that in step (1), the pseudo-ginseng be
Powder, more preferably specification are the pseudo-ginseng powder of 20～60 mesh.
3. preparation method according to claim 1, it is characterised in that in step (1),
The temperature of the warm water is 10～80 DEG C, more preferably 40～70 DEG C；
The time of the immersion preferably 30～90min；
During immersion, the pseudo-ginseng is 1 with the mass volume ratio of warm water:1～1:10.
4. preparation method according to claim 1, it is characterised in that in step (1),
The concentration of the ethanol water is 70～90%, and the pseudo-ginseng with the mass volume ratio of the ethanol water is
1:1～1:100, more preferably 1:20～1:25.
5. preparation method according to claim 1, it is characterised in that in step (1),
Any one being extracted as in seepage pressure effects, circumfluence distillation and supersound extraction；
The time of the extraction preferably 1～6h, more preferably 90～150min.
6. preparation method according to claim 1, it is characterised in that in step (2),
Before by macroporous adsorptive resins on extracting solution, also concentrating under reduced pressure is carried out to the extracting solution, afterwards by after concentration
Macroporous adsorptive resins on extracting solution；
If ethanol water is added in step (1) to be extracted, no alcohol taste is evaporated to the extracting solution
Afterwards, afterwards by macroporous adsorptive resins on the extracting solution after concentration.
7. preparation method according to claim 1, it is characterised in that in step (2), the macroporous adsorbent resin is X-5,
Any one in AB-8, DM-301, NK-2, NKA-2, NK-9, D-101 and WLD.
8. preparation method according to claim 1, it is characterised in that in step (2),
The ethanol water eluting is first to be washed with 0～20% (v/v) ethanol water, discards washing liquid, then with 40～
100% (v/v) ethanol water eluting, collects eluent；
Preferably, before with ethanol water eluting, it is colourless first to wash with water to effluent.
9. preparation method according to claim 1, it is characterised in that also comprise the steps：
(3) Radix Notoginseng total arasaponinss rich in rare N-Fe Ginsenoside Mb and Fd of step (2) gained are adsorbed on silicagel column, use respectively
Chloroform-methanol and acetate-methanol carry out eluting, and Fractional Collections merges the stream part of N-Fe Ginsenoside Mb and Fd, and recovered under reduced pressure is molten
Agent obtains the monomer of N-Fe Ginsenoside Mb and Fd to dry.
10. preparation method according to claim 9, it is characterised in that in step (3),
In the chloroform-methanol, chloroform is 20 with the volume ratio of methanol:1～1:1；
In the acetate-methanol, ethyl acetate is 10 with the volume ratio of methanol:1～1:1.
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| CN115669673A (en) * | 2022-08-18 | 2023-02-03 | 澳门大学 | Application of notoginsenoside Fe and/or notoginsenoside Fd in preparation of plant source bactericide and prevention and treatment of agricultural fungal diseases |
| CN115669673B (en) * | 2022-08-18 | 2024-06-21 | 澳门大学 | Application of notoginsenoside Fe and/or notoginsenoside Fd in preparing plant source bactericide and preventing and treating agricultural fungal diseases |
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