CN114957373B - Extraction and separation method and application of 22 (R) -pseudo-ginseng glycoside Ab1 and epimer pseudo-ginseng glycoside Ab1 thereof in black ginseng - Google Patents
Extraction and separation method and application of 22 (R) -pseudo-ginseng glycoside Ab1 and epimer pseudo-ginseng glycoside Ab1 thereof in black ginseng Download PDFInfo
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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- Chemical Kinetics & Catalysis (AREA)
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- Heart & Thoracic Surgery (AREA)
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Abstract
The invention relates to the field of traditional Chinese medicine extraction and separation, in particular to a pair of epimers extracted, separated and identified from black ginseng and an extraction and separation method thereof. The compound is a pair of epimers and has a molecular formula of C 36 H 60 O 9 Designated 22 (R) -pseudo-ginseng glycoside Ab1 and pseudo-ginseng glycoside Ab1, respectively. Also provides an extraction and separation method of the two compounds, which sequentially adopts ethanol reflux extraction, macroporous adsorption resin purification, silica gel column chromatography, ODS medium-pressure column and liquid phase separation. The structure of the compound is determined to be a novel compound by adopting a mass spectrum, a hydrogen spectrum, a carbon spectrum and a two-dimensional nuclear magnetic spectrum and ECD analysis method, and the compound 2 is an epimer thereof. The compound and the composition thereof have a protective effect on myocardial cell hypoxia/reoxygenation reperfusion injury, and can be used for preparing medicaments for myocardial protection.
Description
Technical Field
The invention relates to the field of traditional Chinese medicine extraction and separation, and relates to a pair of epimers extracted, separated and identified from black ginseng medicinal materials and an extraction and separation method thereof, in particular to an extraction and separation method and application of 22 (R) -pseudo-ginseng glycoside Ab1 and epimers pseudo-ginseng glycoside Ab1 from black ginseng.
Background
The black ginseng is Panax ginseng C.A. Mey of AraliaceaePanax ginsengC.A. Mey. Dried root and rhizome are steamed and sun-dried for several times to obtain ginseng product. Black ginseng was produced in korea at the earliest time and was processed for the purpose of production of rare saponins, and contained a relatively high content of primary saponins deglycosylated and dehydrated products such as Rg3, rg5 and Rh2, which are trace secondary saponins. In recent years, development and research of black ginseng are also carried out in China, but the black ginseng is still not carried by the pharmacopoeia of the people's republic of China.
Modern pharmacological studies show that black ginseng has anticancer, heart failure resisting, liver protecting, immunity enhancing, blood sugar reducing, diabetes resisting, antioxidant activity and central nervous system protecting effects. Research shows that various chemical components contained in the black ginseng are closely related to various pharmacological actions, and the main chemical components comprise: ginsenoside and ginseng polysaccharide. The rare ginsenoside is a major active ingredient in the black ginseng, and the reported ginsenoside ingredients comprise ginsenoside Rk1, rk3, rg5, CK, F4, rg6, rh4, rs5 and the like.
Most of the chemical components separated from the black ginseng are known at present, and the structural novelty is low, so that development and separation of the compounds in the black ginseng are needed.
Disclosure of Invention
In order to solve the problems, the invention provides a new compound 22 (R) -Notoginsenoside Ab1 extracted from black ginseng and epimer Notoginsenoside Ab thereof, and researches show that the compound has the function of myocardial protection, and simultaneously provides a simple, rapid, environment-friendly and high-purity extraction and separation method aiming at the compound.
In order to achieve the above purpose, the present invention provides the following technical solutions.
The invention provides a pair of epimer compounds separated from black ginseng, which is characterized in that the compounds are 22 (R) -notoginseng ginsenoside Ab1 and epimer notoginseng ginsenoside Ab1 thereof, and the molecular formulas are C 36 H 60 O 9 The chemical structural formula is shown as follows:
the invention also provides a method for extracting and separating 22 (R) -pseudo-ginseng glycoside Ab1 and epimer pseudo-ginseng glycoside Ab1, which is characterized by comprising the following steps:
step 3, passing the high-concentration ethanol eluate in the step 2 through a silica gel column, performing gradient elution with dichloromethane-methanol, recovering the eluate to obtain extract, detecting by thin layer chromatography, developing, and mixing the volume ratios of 10:1, merging dichloromethane-methanol parts, and concentrating under reduced pressure until the mixture is dried for later use;
and 5, performing HPLC separation on the concentrate obtained in the step 4, and performing isocratic elution by taking methanol-water as a mobile phase to obtain the compound 22 (R) -sanchinoside Ab1 and sanchinoside Ab1.
Further, in the step 1, ethanol is extracted for 1-3 times under reflux, each time of decoction is carried out for 1-3 hours, the ethanol consumption is 8-16 times of that of the medicinal materials, and the ethanol concentration is 40% -100%.
Further, the resin used in the step 2 is D101 macroporous adsorption resin or AB-8 macroporous adsorption resin; the concentration of the low-concentration ethanol is 10% -60%, and the concentration of the high-concentration ethanol is 60% -90%.
Further, the volume ratio of dichloromethane-methanol used in the step 3 is 0:100, 50:1,30: 1,10: 1 and 5:1, a step of; the silica gel mesh number is 100-300.
Further, the pretreatment process of ODS in the step 4 is that methanol is fully soaked for 8-24 hours, and the pretreated ODS is put on a column and balanced by an initial mobile phase.
Further, the volume ratio of methanol to water used in the step 4 is 10:90, 30:70, 50:50, 70:30, 85:15, 90:10 and 100:0; the particle size of the filler is 40-70 mu m.
Further, the methanol elution procedure used in the step 5 is isocratic elution, and the volume ratio of methanol to water used is 40: 60-70: 30, the retention time of the compound is 50-120min.
The invention also provides application of the pair of epimer compounds separated from the black ginseng, which is characterized in that the compounds 22 (R) -pseudo-ginseng glycoside Ab1 and pseudo-ginseng glycoside Ab1 are used for preparing medicaments for protecting cardiac muscles.
The invention also provides a pharmaceutical composition for myocardial protection, which is characterized by comprising any one compound of 22 (R) -pseudo-ginseng glycoside Ab1 and a pharmaceutically acceptable carrier thereof.
Compared with the prior art, the invention has the beneficial effects.
The separation and pharmacological activity research of the new compound 22 (R) -Notoginsenoside Ab1 in the black ginseng are not reported by the prior art, and the Notoginsenoside Ab1 structure is reported, but the separation from the black ginseng is the first time; the invention provides a pair of epimers from black ginseng and an extraction and separation method for the compound, which sequentially adopts ethanol reflux extraction, silica gel column chromatography, ODS medium-pressure column and high performance liquid chromatograph for separation, purification and preparation, and two compounds are successfully extracted and separated.
Drawings
FIG. 1 is a high resolution mass spectrum of compound 22 (R) -Notoginsenoside Ab1 of the present invention.
FIG. 2 shows compound 22 (R) -Notoginsenoside Ab1 of the invention 13 C-NMR chart.
FIG. 3 shows compound 22 (R) -Notoginsenoside Ab1 of the invention 1 H-NMR chart.
FIG. 4 is a HSQC spectrum of Compound 22 (R) -Notoginsenoside Ab1 of the present invention.
FIG. 5 is a HMBC pattern of compound 22 (R) -Notoginsenoside Ab1 of the present invention.
FIG. 6 shows a compound Notoginsenoside Ab1 of the invention 13 C-NMR chart.
FIG. 7 shows CD and ECD spectra of compounds 22 (R) -Notoginsenoside Ab1 and Notoginsenoside Ab1 of the present invention.
Detailed Description
The present invention will be described in detail with reference to specific examples. The following examples will aid in the understanding of the present invention, but are merely illustrative of the invention and the invention is not limited thereto. The methods of operation in the examples are all conventional in the art.
Example 1. The invention provides two compounds 22 (R) -Notoginsenoside Ab1, notoginsenoside Ab1 in black ginseng, the molecular formula is C 36 H 60 O 9 The chemical structural formula is as follows:
the compounds were designated by structure 22 (R) -Notoginsenoside Ab1, notoginsenoside Ab1, and table 1 shows the nuclear magnetic data of the two compounds: 1 H-NMR (600 MHz) 13 C-NMR (150 MHz) at C 5 D 5 N.
Table 1: nuclear magnetic data for inventive compound 22 (R) -Notoginsenoside Ab1 and Notoginsenoside Ab1.
Structural identification and derivation of novel compound 22 (R) -Notoginsenoside Ab1 of the present invention.
22 (R) -Notoginsenoside Ab1: white amorphous powder, easy to dissolve in pyridine and methanol. After spotting on a silica gel thin layer plate, the spots are purple after spraying the vanillin-sulfuric acid color developing agent. HRESI (-) TOFMS gives M/z 671.3930 [ M+Cl ]] - 、1037.8059[2M+Cl] - The molecular weight of the excimer ion peak is 636.8670. Bonding of 1 H-NMR， 13 C-NMR data, it is assumed that the possible molecular formula of the compound is C 36 H 60 O 9 The unsaturation was 7. From the following components 13 C-NMR 1 The H-NMR spectrum shows that the structure contains 36 carbon signals, 4 olefin carbons, delta: 160.54 108.61, 123.15, 132.14;3 olefins hydrogen, δ:5.61 (1H, t, j=6.83 Hz), 5.46 (1H, brs). At the same time 7 methyl hydrogen signals were observedAnd delta: 0.85 (3H, s), 1.05 (3H, s), 1.27 (3H, s), 1.62 (3H, s), 1.65 (3H, s), 1.68 (3H, s), 2.09 (3H, s), corresponding to 7 methyl carbon signals, δ:16.38, 16.73, 17.38, 17.79, 18.13, 25.94, 31.74. Bonding of 13 C-NMR 1 H-NMR spectrum, group 1 carbon signal, δ:106.05, 79.70, 78.19, 75.50, 71.86, 63.11, it is known that the structure contains a glucosyl group, corresponding to a hydrogen signal, δ:5.06 (1H, d, j=7.79 Hz), 4.54 (1H, m), 4.40 (1H, dd, j=10.39, 4.30 Hz), 4.27 (1H, t, j=8.70 Hz), 4.24 (1H, t, j=9.00 Hz), 4.12 (1H, t, j=7.70 Hz), 3.97 (1H, ddd, j=9.07, 5.43, 2.73 Hz), the glucose end group hydrogen being as follows from the coupling constants of the end group hydrogenβConfiguration. Furthermore, the chemical signal of carbon, δ:16.38, 16.73, 17.38, 17.79, 27.98, 31.74, 32.59, 32.72, 34.02, 39.51, 39.74, 40.42, 41.27, 44.13, 45.38, 50.68, 51.63, 57.24, 61.48, 72.48, 78.57, 80.08 demonstrated a structural dammarane-type tetracyclic triterpene parent nuclear carbon signal. Further the structural fragment [ (CH 3) 2C=CH-CH 2-CH (OH) -C (=CH 2) was resolved by HSQC and HMBC spectra]. The final complete molecular structure is composed of dammarane type tetracyclic triterpene mother nucleus, beta-D glucosyl and [ (CH 3) 2C=CH-CH 2-CH (OH) -C (=CH 2) & gt]The composition is formed. The absolute configuration of carbon number 22 was determined by comparing the CD spectra of the compound, which carbon number 22 was in the R configuration, with the ECD of 22 (S) -and 22 (R) -3 beta, 6 alpha, 12 beta-tetrahydroxy-dammar-20 (21), 24-diene-6-O-beta-D-glucopyranoside, the final compound was designated 22 (R) -Notoginsenoside Ab1.
Structural identification of the compound Notoginsenoside Ab of the invention.
Notoginsenoside Ab1: white amorphous powder, easy to dissolve in pyridine and methanol. After spotting on a silica gel thin layer plate, the spots are purple after spraying the vanillin-sulfuric acid color developing agent. From the following components 13 The C-NMR spectrum shows that the structure contains 36 carbon signals, of which 4 olefins are carbon, delta: 122.01, 132.41, 110.67, 159.75 indicate the presence of 2 double bonds in the structure. Delta: 106.05, 79.70, 78.20, 76.52, 71.87, 63.11 indicate the presence of a glucose group in the structure. In addition, 16.38, 16.70, 17.35, 17.79, 27.96, 31.73, 32.26, 32.97, 34.25, 39.47, 39.71, 39.72, 40.40, 41.26, 45.41, 50.65, 51.78, 58.64, 61.43, 72.51, 78.51, 80.03 carbon signals were also observed, passing through the text and textDocument (Li Q, yuan M, li X, et al New dammarane-type triterpenoid saponins from Panax notoginseng saponins [ J)]Journal of Ginseng Research,2020,44 (5): 673-679.) the data were identical and compound 2 was identified as Notoginsenoside Ab1.
From the above information, it can be determined that this compound has the above structure.
The invention also provides an extraction and separation method of the novel compound, which comprises the following specific steps of.
Step 1: weighing 10kg of dry medicinal materials of black ginseng, reflux-extracting with 70% ethanol, wherein the ethanol dosage is 10 times of that of the medicinal materials, reflux-extracting twice, decocting for 2 hours each time, filtering the extracting solution, mixing the filtrates, heating and concentrating to 5L, and cooling to room temperature to obtain medicinal liquid for later use.
Step 2: injecting the concentrated solution in the step 1 into 15L D101 macroporous adsorption resin, eluting with water (50L), 60% ethanol (50L) and 95% ethanol (50L) in sequence, and drying the 95% ethanol eluent.
Step 3: dissolving the 95% ethanol eluate in the step 2 by adding methanol, stirring with 100-200 mesh silica gel, separating by a 200-300 mesh silica gel column, eluting with dichloromethane-methanol gradient (100:0, 50:1, 30:1, 10:1, 5:1), mixing the dichloromethane-methanol (10:1) eluting parts, and concentrating under reduced pressure until dry for use.
And 4, subjecting the product obtained in the step 3 to pretreated ODS column (octocryllyl, octadecylsilane chemically bonded silica filler) chromatography separation, eluting with methanol-water gradient (10:90, 30:70, 70:30 and 100:0) to obtain 4 elution parts, concentrating 70% methanol elution part under reduced pressure until dry, and obtaining concentrate for later use.
The mobile phase was subjected to isocratic elution at a flow rate of 2ml/min and a detection wavelength of 210nm. Finally, the novel compound 22 (R) -Notoginsenoside Ab1 and the epimer Notoginsenoside Ab1 thereof are obtained, and the purity is 93-99% through normalized measurement.
Example 2 myocardial protection by the compounds of the present invention.
1. The main material.
1.1 Medicine and reagent: the new compound used in the experiment is prepared by the method, the purity is 99%, the new compound is precisely weighed, and the new compound is dissolved in DMSO and then diluted to the required concentration by adding culture solution. DMEM medium, fetal bovine serum (Hyclone company, usa); penicillin, streptomycin (Hangzhou holly company), CCK-8 kit (Nanjing built bioengineering).
1.2 Experimental animals: SD rats (SCXK 2020-0001, liaoning Long Biotechnology Co., ltd.) were born for 2 days.
1.3 Grouping: the groups were divided into normal group, model group and low, medium and high dosing group (culture medium containing DMSO vehicle).
2. Experimental methods.
2.1 In vitro isolation and culture of SD rat mammary rat cardiomyocytes.
Collecting SD milk mice within 3 days of new born, picking heart apex, transferring to culture dish containing pre-cooled PBS, and cutting heart into 1mm with ophthalmic forceps 3 Left and right small blocks.
The tissue fragments were digested with pancreatin in a 37 ℃ water bath with shaking, the supernatant carefully aspirated, and transferred to DMEM pre-loaded with 5mL of 10% fbs (this procedure was repeated 5-8 times).
All cell suspensions were combined, sieved through a 200 mesh sieve, centrifuged at 1000rpm for 5min, the supernatant was discarded, resuspended in DMEM containing 10% fbs and differential cultured in petri dishes.
After 1.5h, the upper non-adherent cells were carefully aspirated into another petri dish at 37℃with 5% CO 2 The incubator was cultured until the cell pseudopodia extended, and synchronous pulsation was started, and the next experiment was performed.
And (5) measuring cytotoxic activity.
Treating rat myocardial cells with pancreatin to give a concentration of 1×10 4 cell/well single cell suspensions were seeded in 96-well plates (200 μl) with 3 parallel wells per group.
The stock culture was discarded, and 200. Mu.L of 22 (R) -Notoginsenoside Ab1 and Notoginsenoside Ab1 culture medium each at a concentration of 1. Mu.M, 10. Mu.M, 30. Mu.M was added to each well. After 24 hours of incubation, the wells were aspirated and 200. Mu.L of fresh complete medium containing 5. Mu.L of CCK-8 cell viability assay reagent was added to each well. Cells were incubated in an incubator at 37℃for 4h and absorbance of each well was measured at 450nm using the Elisa kit to determine their cytotoxic activity against both.
2.2 And (5) establishing an in-vitro myocardial cell hypoxia/reoxygenation model.
Cardiomyocytes were incubated at 37℃with 95% N 2 ，5％CO 2 After the culture in the constant temperature incubator, the cell fusion degree>90% of the time was used for experiments, 96-well plates were plated to allow the cells to adhere to the wall and extend out of the pseudopodia.
The DMEM medium containing 10% FBS was discarded, and a sugar-free serum-free medium was added thereto, and 95% N was introduced 2 ，5％CO 2 The experiment was started after pre-saturation.
Replacing culture solution in 96-well plate with sugar-free and serum-free culture medium, placing in anoxia device, and using 95% N 2 ，5％CO 2 After replacing the air in the device for half an hour, sealing the device, and performing anoxic cultivation for 4 hours in an incubator at 37 ℃ to establish an anoxic model.
After the hypoxia was completed, the culture medium was replaced with DMEM medium containing 10% fbs, and cultured in a normal incubator for 4 hours, to obtain a hypoxia/reoxygenation myocardial injury cell model.
2.3 The CCK-8 method detects the protective effect of the compound on myocardial cell hypoxia/reoxygenation reperfusion injury.
Treating rat myocardial cells with pancreatin to give a concentration of 1×10 4 cell/well single cell suspensions were seeded in 96-well plates (200 μl) with 3 parallel wells per group.
The HRI model cardiomyocyte stock was discarded and 200. Mu.L of 22 (R) -Notoginsenoside Ab1 was added per well. After 24 hours of incubation, the wells were aspirated and 200. Mu.L of fresh complete medium containing 5. Mu.L of CCK-8 cell viability assay reagent was added to each well. Cells were incubated in an incubator at 37℃for 4h, and absorbance of each well was measured at 450nm using the Elisa kit to determine their protective effect on HRI model cardiomyocytes.
Relative cell viability = OD value of the above-described drug-loaded cell group/OD value of the normal cell group.
All data were processed with SPSS 20.0 software and expressed as mean±sd values. P values <0.05 were considered statistically significant using a set t-test comparison.
3. Experimental results.
At concentrations of 1. Mu.M, 10. Mu.M, and 30. Mu.M, neither 22 (R) -Notoginsenoside Ab1 nor Notoginsenoside Ab1 showed cytotoxic effects.
The viability of 22 (R) -Notoginsenoside Ab1, notoginsenoside Ab1 against damaged myocardium at concentrations of 1. Mu.M, 10. Mu.M, 30. Mu.M is shown in Table 2.
Table 2 protection of hypoxia/reoxygenation cardiomyocyte injury models by (R) -Notoginsenoside Ab1, notoginsenoside Ab1.
Note that: # P <0.01 compared to the blank; * P <0.05 compared to model group.
Experimental results show that the 22 (R) -Notoginsenoside Ab1 and Notoginsenoside Ab1 with the concentrations have a good protection effect on myocardial cells induced by HRI, and the protection capability on myocardial injury cells is obviously improved along with the increase of the drug concentration. Notoginsenoside Ab1 is more myocardial protective than 22 (R) -Notoginsenoside Ab1.
In summary, the invention provides a method for extracting and separating a novel compound and an epimer thereof, which sequentially adopts ethanol reflux extraction, silica gel column chromatography, ODS medium-pressure column and liquid phase separation to prepare the novel compound and the epimer thereof, and the method is simple, convenient, quick and environment-friendly, and the purity of the compound separated by the method is higher.
Claims (8)
1. A method for extracting and separating a pair of epimeric compounds separated from black ginseng, comprising the steps of:
step 1, drying and crushing black ginseng medicinal materials, adopting ethanol for reflux extraction, filtering an extracting solution, merging filtrate, concentrating under reduced pressure, and cooling to room temperature to obtain a medicinal liquid for later use;
step 2, the concentrated solution in the step 1 is subjected to macroporous adsorption resin, water, low-concentration ethanol and high-concentration ethanol are sequentially used for eluting, high-concentration ethanol eluate is collected, and reduced pressure concentration and drying are carried out;
step 3, passing the high-concentration ethanol eluate in the step 2 through a silica gel column with the volume ratio of 0:100, 50:1,30: 1,10: 1 and 5:1, recovering eluent to extract, detecting by thin layer chromatography, developing, and mixing the volume ratio of 10:1, merging dichloromethane-methanol parts, and concentrating under reduced pressure until the mixture is dried for later use;
step 4, separating the product obtained in the step 3 by pretreated ODS column chromatography, wherein the volume ratio is 10:90, 30:70, 50:50, 70:30, 85:15, 90:10 and 100:0, obtaining a plurality of elution parts, detecting by thin layer chromatography, developing, concentrating the developed elution parts to dryness under reduced pressure to obtain a concentrate for later use;
step 5, performing HPLC separation preparation on the concentrate obtained in the step 4, and performing isocratic elution by taking methanol-water as a mobile phase, wherein the volume ratio of the methanol to the water is 40: 60-70: 30 to obtain a compound 22 (R) -pseudo-ginseng glycoside Ab1 and pseudo-ginseng glycoside Ab1; the compound is 22 (R) -notoginseng ginsenoside Ab1 and epimer notoginseng ginsenoside Ab1, and the molecular formula is C 36 H 60 O 9 The chemical structural formula is shown as follows:
2. the extraction and separation method according to claim 1, wherein in the step 1, ethanol is extracted by reflux for 1-3 times, each time of decoction is carried out for 1-3 hours, the ethanol consumption is 8-16 times of that of the medicinal materials, and the ethanol concentration is 40% -100%.
3. The extraction and separation method according to claim 1, wherein the resin used in the step 2 is D101 macroporous adsorption resin or AB-8 macroporous adsorption resin; the concentration of the low-concentration ethanol is 10% -60%, and the concentration of the high-concentration ethanol is 60% -90%.
4. The extraction and separation method according to claim 1, wherein the silica gel mesh number in the step 3 is 100-300 mesh.
5. The separation method according to claim 1, wherein the pretreatment of ODS in step 4 is carried out by immersing in methanol for 8-24 hours, loading to column, and balancing with initial mobile phase.
6. The extraction and separation method according to claim 1, wherein the filler particle size in the step 4 is 40 to 70. Mu.m.
7. The extraction and separation method according to claim 1, wherein the methanol elution procedure used in the step 5 is isocratic elution, and the retention time of the compound is 50 to 120min.
8. The use of compound 22 (R) -pseudo-ginseng glycoside Ab1 and pseudo-ginseng glycoside Ab1 prepared by the extraction and separation method as defined in claim 2 for preparing a medicament for myocardial protection.
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