CN108623649A - A method of isolating and purifying notoginsenoside Fc from sanchi leaf total saposins - Google Patents
A method of isolating and purifying notoginsenoside Fc from sanchi leaf total saposins Download PDFInfo
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- CN108623649A CN108623649A CN201810612165.2A CN201810612165A CN108623649A CN 108623649 A CN108623649 A CN 108623649A CN 201810612165 A CN201810612165 A CN 201810612165A CN 108623649 A CN108623649 A CN 108623649A
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- notoginsenoside
- methanol
- volume ratio
- total saposins
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- XBGLCVZQMWKHFC-UBJQIMRZSA-N Notoginsenoside Fc 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]4[C@H](O[C@H]5[C@H](O)[C@H](O)[C@@H](O)CO5)[C@@H](O)[C@H](O)[C@@H](CO)O4)[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 XBGLCVZQMWKHFC-UBJQIMRZSA-N 0.000 title claims abstract description 50
- XBGLCVZQMWKHFC-UHFFFAOYSA-N notoginsenoside fc Chemical compound C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)OC4C(C(O)C(O)C(CO)O4)OC4C(C(O)C(O)CO4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O XBGLCVZQMWKHFC-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 239000009759 San-Chi Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 14
- 238000004440 column chromatography Methods 0.000 claims abstract description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 78
- 239000003480 eluent Substances 0.000 claims description 22
- 238000010829 isocratic elution Methods 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 12
- 229930182490 saponin Natural products 0.000 claims description 11
- 150000007949 saponins Chemical class 0.000 claims description 11
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 10
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 238000002013 hydrophilic interaction chromatography Methods 0.000 claims description 8
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 238000004090 dissolution Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 229930189092 Notoginsenoside Natural products 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000013558 reference substance Substances 0.000 abstract description 2
- 239000012467 final product Substances 0.000 abstract 1
- 238000004305 normal phase HPLC Methods 0.000 abstract 1
- 229920003266 Leaf® Polymers 0.000 description 18
- 235000017709 saponins Nutrition 0.000 description 10
- 241000180649 Panax notoginseng Species 0.000 description 6
- 235000003143 Panax notoginseng Nutrition 0.000 description 6
- 238000000926 separation method Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 241000208343 Panax Species 0.000 description 1
- 244000131316 Panax pseudoginseng Species 0.000 description 1
- 235000003181 Panax pseudoginseng Nutrition 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 231100001028 renal lesion Toxicity 0.000 description 1
- 230000001084 renoprotective effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
Classifications
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention discloses a kind of method that notoginsenoside Fc is isolated and purified in total saposins from sanchi leaf, using sanchi leaf total saposins as raw material, notoginsenoside Fc crude product is prepared by medium pressure column chromatography, then inverted high performance liquid chromatography and normal phase high performance liquid chromatography purify to obtain the final product.98% or more sterling of content can be obtained, reach reference substance rank.
Description
Technical field
The present invention relates to the extraction separation and purification technical fields of effective component of chinese medicine, specifically in sanchi leaf total saposins three
The isolation and purification method of seven saponin(e Fc.
Background technology
It is Radix Notoginseng also known as pseudo-ginseng, invaluable, it is panax araliaceae plantPanax notoginseng (Burk.) F. H.
The dry root and rhizome of Chen.It is distributed mainly on the ground such as Yunnan, Guangxi, Jiangxi, Sichuan.Traditional effect is invigorated blood circulation for hemostasis, is dissipated
Swollen, analgesic of stagnation resolvation etc..Modern study discovery all has various lifes to cardio-cerebrovascular, nervous system, immune system etc.
Reason acts on.Due to the diverse biological activities of Radix Notoginseng, usage amount increases, the supply of Panax notoginseng root be difficult meet it is growing
The market demand.Comprehensive utilization based on Radix Notoginseng resource and Optimum utilization, there is an urgent need to develop new resource and using plant other
Position resource.Compared with the long period needed for root system, the year rate of recovery of leaf may be another source.Radix Notoginseng different parts are not rich in
The saponin(e of same type, the significant difference as sanchi leaf and root are to contain 20 abundant (S)-protopanaxadiol-type saponin(es in leaf.
At present according to the literature, notoginsenoside Fc has apparent inhibition platelet aggregation, improves the works such as myocardial ischemia, myocardial preservation
With can be used for preventing myocardial ischemia, the various thrombotic diseases such as myocardial infarction.Zheng Liyang etc. also confirms that notoginsenoside Fc can reduce
Diabetes B db/db mouse Urine proteins, delay renal lesions to be in progress, and have Renoprotective Effect.By the above results, we can
To find out, currently necessary to the research of saponin(e active ingredient in sanchi leaf, it can not only optimize the utilization of resources, also very well
Medical value.Wherein notoginsenoside Fc is 20 (S)-protopanoxadiol saponins, is main effectively living in sanchi leaf total saposins
Property ingredient.Therefore the active constituent notoginsenoside Fc in extraction purification sanchi leaf total saposins is of great significance.It is up to now
Only, there are no high-content notoginsenoside Fc isolates and purifies patent report.
Invention content
The present invention provides a kind of method that notoginsenoside Fc is isolated and purified in total saposins from sanchi leaf, with sanchi leaf total saposins
It is enriched with the part containing notoginsenoside Fc, the part of enrichment is purified, is finally obtained by column chromatography for separation for raw material
High-purity notoginsenoside Fc, for notoginsenoside Fc comprehensive development and utilization and notoginsenoside Fc it is a large amount of preparation provide it is important according to
According to.
The technical solution adopted by the present invention is as follows：
A method of notoginsenoside Fc being isolated and purified from sanchi leaf total saposins, the specific steps are：
（1）Sanchi leaf total saposins are dissolved in methanol aqueous solution, medium pressure column chromatography are carried out using LK-20 resins, with methanol-water system
Isocratic elution is carried out, eluent is collected, concentration obtains notoginsenoside Fc crude product；
（2）It by notoginsenoside Fc crude product methanol dissolution filter, is prepared with reversed-phased high performace liquid chromatographic, collection contains three
The eluent of seven saponin(e Fc, is dissolved after concentration with methanol, is put to precipitation white crystal；
（3）White crystal chromatography methanol is dissolved, is purified with positive high performance liquid chromatography, collection contains notoginsenoside
The eluent of Fc is to get notoginsenoside Fc after purification.
Step（1）It is middle that sanchi leaf total saposins are dissolved in the methanol aqueous solution that volume ratio is 20-60%；It is 71- with volume ratio
74% methanol-water system carries out isocratic elution, and medium pressure column chromatography flow velocity is 15-30mL/min.
Step（2）Middle reversed-phased high performace liquid chromatographic uses C18 columns, the acetonitrile-water system that volume ratio is 28-31% to carry out
Isocratic elution, flow velocity 15-20mL/min.
Step（3）It is middle forward direction high performance liquid chromatography use HILIC columns, volume ratio be 30-33% acetonitrile-water system into
Row isocratic elution, flow velocity 15-20mL/min.
The advantage of the invention is that：
1, notoginsenoside Fc is prepared using LK-20 resin separation for the first time, can rapidly and efficiently obtains notoginsenoside Fc crude product, simplify behaviour
Make process, and resin can Reusability, it is economic and environment-friendly；
2, standby, easy to operate, the saving time is suppressed in being used in separation process；In middle pressurizing resin column separation process, being not used has
Poison, expensive organic solvent, cost-effective, environmental protection；
3, HILIC chromatographic columns are that the neutral amide bonds of unique structure close phase, and hydrophily protrudes, and avoids pure silicon glue surface silicon
The acidity and inhomogeneity of alcohol radical.Doing mobile phase using high proportion acetonitrile-water can be retained on traditional reverse-phase chromatographic column very
It is difficult to ensure the highly polar compound stayed；
4, the notoginsenoside Fc that purity is up to 98% or more is can get, reaches reference substance rank, and the method for the present invention can be used for largely
The preparation of notoginsenoside Fc.
Specific implementation mode
In order to make those skilled in the art understand the present invention in detail, with reference to specific embodiment to the technical side of the present invention
Case is described further.
In following embodiment, sanchi leaf total saposins are bought from Yunnan Province Yuxi City Weihe Pharmaceutical Co.ltd；The C18 of use
Column（YMC-Pack ODS-A, 250mm × 20mm, 5 μm）For Tokyo YMC Co. products, HILIC chromatographic columns（XAmide,
150mm × 4.6mm, 5 μm）Tech is composed for China（Beijing）Science and Technology Ltd.'s product.
Embodiment 1
The 100g sanchi leafs total saposins methanol aqueous solution that a small amount of volume ratio is 20% is taken to dissolve, filtering.It is carried out with LK-20 resins
Medium pressure column chromatography, the methanol-water system for being 71% with volume ratio carry out isocratic elution, and flow velocity 20mL/min collects eluent,
Concentration, obtains notoginsenoside Fc crude product.By notoginsenoside Fc crude product methanol dissolution filter, the second for being 28% through volume ratio with C18 columns
Nitrile-water system carries out isocratic elution, and flow velocity 18mL/min collects the eluent containing notoginsenoside Fc, and three are detected in 203nm
The peak area of seven saponin(e Fc is 91.7%.It will be dissolved, put to analysis with methanol after the eluent concentration containing notoginsenoside Fc of collection
Go out white crystal, by white crystal with chromatography methanol dissolve, with HILIC chromatographic columns through volume ratio be 30% acetonitrile-water system into
Row isocratic elution, flow velocity 16mL/min collect the eluent containing notoginsenoside Fc to get notoginsenoside Fc after purification,
Detection level is 98.2%, the dry 330mg that weighs to obtain, yield 0.33%.
Embodiment 2
The 100g sanchi leafs total saposins methanol aqueous solution that a small amount of volume ratio is 30% is taken to dissolve, filtering.It is carried out with LK-20 resins
Medium pressure column chromatography, the methanol-water system for being 72% with volume ratio carry out isocratic elution, and flow velocity 15mL/min collects eluent,
Concentration, obtains notoginsenoside Fc crude product.By notoginsenoside Fc crude product methanol dissolution filter, the second for being 29% through volume ratio with C18 columns
Nitrile-water system carries out isocratic elution, and flow velocity 19mL/min collects the eluent containing notoginsenoside Fc, and three are detected in 203nm
The peak area of seven saponin(e Fc is 91.5%.It will be dissolved, put to analysis with methanol after the eluent concentration containing notoginsenoside Fc of collection
Go out white crystal, by white crystal with chromatography methanol dissolve, with HILIC chromatographic columns through volume ratio be 31% acetonitrile-water system into
Row isocratic elution, flow velocity 18mL/min collect the eluent containing notoginsenoside Fc to get notoginsenoside Fc after purification,
Detection level is 98.3%, the dry 320mg that weighs to obtain, yield 0.32%.
Embodiment 3
The 100g sanchi leafs total saposins methanol aqueous solution that a small amount of volume ratio is 45% is taken to dissolve, filtering.It is carried out with LK-20 resins
Medium pressure column chromatography, the methanol-water system for being 73% with volume ratio carry out isocratic elution, and flow velocity 25mL/min collects eluent,
Concentration, obtains notoginsenoside Fc crude product.By notoginsenoside Fc crude product methanol dissolution filter, the second for being 30% through volume ratio with C18 columns
Nitrile-water system carries out isocratic elution, and flow velocity 15mL/min collects the eluent containing notoginsenoside Fc, and three are detected in 203nm
The peak area of seven saponin(e Fc is 91.5%.It will be dissolved, put to analysis with methanol after the eluent concentration containing notoginsenoside Fc of collection
Go out white crystal, by white crystal with chromatography methanol dissolve, with HILIC chromatographic columns through volume ratio be 32% acetonitrile-water system into
Row isocratic elution, flow velocity 15mL/min collect the eluent containing notoginsenoside Fc to get notoginsenoside Fc after purification,
Detection level is 98.3%, the dry 360mg that weighs to obtain, yield 0.36%.
Embodiment 4
The 100g sanchi leafs total saposins methanol aqueous solution that a small amount of volume ratio is 60% is taken to dissolve, filtering.It is carried out with LK-20 resins
Medium pressure column chromatography, the methanol-water system for being 74% with volume ratio carry out isocratic elution, and flow velocity 30mL/min collects eluent,
Concentration, obtains notoginsenoside Fc crude product.By notoginsenoside Fc crude product methanol dissolution filter, the second for being 31% through volume ratio with C18 columns
Nitrile-water system carries out isocratic elution, and flow velocity 16mL/min collects the eluent containing notoginsenoside Fc, and three are detected in 203nm
The peak area of seven saponin(e Fc is 91.4%.It will be dissolved, put to analysis with methanol after the eluent concentration containing notoginsenoside Fc of collection
Go out white crystal, by white crystal with chromatography methanol dissolve, with HILIC chromatographic columns through volume ratio be 33% acetonitrile-water system into
Row isocratic elution, flow velocity 20mL/min collect the eluent containing notoginsenoside Fc to get notoginsenoside Fc after purification,
Detection level is 98.1%, the dry 370mg that weighs to obtain, yield 0.37%.
Claims (6)
1. a kind of method that notoginsenoside Fc is isolated and purified in total saposins from sanchi leaf, the specific steps are：
（1）Sanchi leaf total saposins are dissolved in methanol aqueous solution, medium pressure column chromatography are carried out using LK-20 resins, using methanol-water system
System carries out isocratic elution, collects eluent, and concentration obtains notoginsenoside Fc crude product；
（2）It by notoginsenoside Fc crude product methanol dissolution filter, is prepared with reversed-phased high performace liquid chromatographic, collection contains three
The eluent of seven saponin(e Fc, is dissolved after concentration with methanol, is put to precipitation white crystal；
（3）White crystal chromatography methanol is dissolved, is purified with positive high performance liquid chromatography, collection contains notoginsenoside
The eluent of Fc is to get notoginsenoside Fc after purification.
2. according to the method described in claim 1, it is characterized in that, step（1）It is middle sanchi leaf total saposins are dissolved in volume ratio to be
The methanol aqueous solution of 20-60%.
3. according to the method described in claim 1, it is characterized in that, step（1）The middle methanol-water system for being 71-74% with volume ratio
System carries out isocratic elution.
4. according to the method described in claim 1, it is characterized in that, step（1）Middle medium pressure column chromatography flow velocity is 15-30mL/
min。
5. according to the method described in claim 1, it is characterized in that, step（2）Middle reversed-phased high performace liquid chromatographic uses C18
Column, the acetonitrile-water system that volume ratio is 28-31% carry out isocratic elution, flow velocity 15-20mL/min.
6. according to the method described in claim 1, it is characterized in that, step（3）Middle forward direction high performance liquid chromatography uses HILIC
Column, the acetonitrile-water system that volume ratio is 30-33% carry out isocratic elution, flow velocity 15-20mL/min.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810612165.2A CN108623649B (en) | 2018-06-14 | 2018-06-14 | Method for separating and purifying notoginsenoside Fc from total saponins of panax notoginseng leaves |
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|---|---|---|---|
| CN201810612165.2A CN108623649B (en) | 2018-06-14 | 2018-06-14 | Method for separating and purifying notoginsenoside Fc from total saponins of panax notoginseng leaves |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115006493A (en) * | 2022-06-20 | 2022-09-06 | 昆明理工大学 | Notoginseng saponin composition for preventing and treating diabetes and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1634970A (en) * | 2004-11-18 | 2005-07-06 | 张平 | Process for preparing notoginsen triterpenes |
| CN103724390A (en) * | 2012-10-15 | 2014-04-16 | 中国科学院大连化学物理研究所 | Saponin separation and purification method |
| AU2014100715A4 (en) * | 2014-04-15 | 2014-07-17 | Macau University Of Science And Technology | Method for authenticating panax notoginseng plant material |
-
2018
- 2018-06-14 CN CN201810612165.2A patent/CN108623649B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1634970A (en) * | 2004-11-18 | 2005-07-06 | 张平 | Process for preparing notoginsen triterpenes |
| CN103724390A (en) * | 2012-10-15 | 2014-04-16 | 中国科学院大连化学物理研究所 | Saponin separation and purification method |
| AU2014100715A4 (en) * | 2014-04-15 | 2014-07-17 | Macau University Of Science And Technology | Method for authenticating panax notoginseng plant material |
Non-Patent Citations (3)
| Title |
|---|
| MASAYUKI YOSHIKAWA等: "Structures of New Dammarane-Type Triterpene Saponins from the Flower Buds of Panax notoginseng and Hepatoprotective Effects of Principal Ginseng Saponins", 《J. NAT. PROD.》 * |
| XIN-YI LIU等: "Dammarane-type saponins from the leaves of Panax notoginseng and their neuroprotective effects on damaged SH-SY5Y cells", 《PHYTOCHEMISTRY》 * |
| XIUJIE GUO等: "Purification of saponins from leaves of Panax notoginseng using preparative two-dimensional reversed-phase liquid chromatography/hydrophilic interaction chromatography", 《ANAL BIOANAL CHEM》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115006493A (en) * | 2022-06-20 | 2022-09-06 | 昆明理工大学 | Notoginseng saponin composition for preventing and treating diabetes and preparation method thereof |
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