CN108558809B - Compound Oleracone F in purslane and extraction and separation method thereof - Google Patents
Compound Oleracone F in purslane and extraction and separation method thereof Download PDFInfo
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Abstract
The invention relates to the field of extraction and separation of traditional Chinese medicines, in particular to a novel compound extracted, separated and identified from a purslane medicinal material and an extraction and separation method thereof, and specifically relates to a compound Oleracone F in purslane and an extraction and separation method thereof. The present invention provides novel compounds of the formula C18H16O5And is named as oleracee F. Researches show that the novel compound has anti-inflammatory and antioxidant effects, and provides a simple, convenient, rapid, environment-friendly and high-purity extraction and separation method for the novel compound.
Description
Technical Field
The invention relates to the field of extraction and separation of traditional Chinese medicines, in particular to a novel compound extracted, separated and identified from a purslane medicinal material and an extraction and separation method thereof, and specifically relates to a compound Oleracone F in purslane and an extraction and separation method thereof.
Background
Herba Portulacae (Portulaca oleracea L.), also called herba Portulacae and herba Portulacae, is a plant of Portulacaceae. Purslane has drought and waterlogging resistance, light and yin resistance, wide distribution and rich resources, is taken as a medicinal and edible wild plant, takes dry overground parts of purslane as a medicament in 2015 edition pharmacopoeia of the people's republic of China, has the effects of clearing heat and detoxicating, cooling blood and stopping bleeding, stopping dysentery and the like, and is used for treating heat toxin and bloody dysentery, carbuncle swelling and furuncle, eczema, erysipelas, snake and insect bite, hematochezia, hemorrhoidal bleeding, metrorrhagia and metrostaxis and the like.
Modern pharmacological research of purslane shows that the purslane has the effects of resisting inflammation, relieving pain, resisting bacteria and viruses, reducing blood pressure, reducing blood fat, resisting oxidation and cancers, relaxing skeletal muscles and smooth muscles, regulating immune function and the like. Research shows that numerous chemical components of purslane provide material basis for various pharmacological actions of purslane, and the main chemical components of purslane comprise flavonoids, coumarins, terpenes, steroids, alkaloids, amino acids, various pigments, minerals and the like. Wherein alkaloids are a main chemical component in purslane, and the alkaloid components reported at present comprise norepinephrine, dopamine, a small amount of dopa, adenosine, uracil, adenine, N-dicyclohexylurea, allantoin and N-trans-feruloyltyramine; cyclic dipeptide alkaloids and amide alkaloids are also present: oleracein A-I, K, L, N-S.
Most of the chemical components separated from purslane are known and have low structural novelty, so the development and separation of new compounds in purslane are urgently needed.
Disclosure of Invention
In order to solve the problems, the invention provides a compound Oleracone F in purslane and an extraction and separation method thereof, in particular to a new compound extracted from purslane.
To achieve the above objects, the present invention provides a novel compound of formula C18H16O5And is named as oleracee F. The chemical structural formula is as follows:
in order to achieve the above purpose, the invention also provides a method for extracting and separating compound oleracee F from purslane, which comprises the following specific steps.
And 2, evaporating the liquid medicine obtained in the step 1 to dryness, putting the liquid medicine on a silica gel column, eluting the liquid medicine by using ethyl acetate, and recovering the ethyl acetate under reduced pressure to obtain an extract so as to obtain an ethyl acetate extract.
And 3, separating the ethyl acetate extract obtained in the step 2 by using a polyamide column, performing gradient elution by using ethanol-water, evaporating 50% ethanol to dryness, then putting the ethyl acetate extract on a silica gel column, sequentially performing gradient elution by using ethyl acetate-methanol to obtain a plurality of elution parts, detecting by using a thin-layer chromatography, developing, combining the developed elution parts, and concentrating the combined elution parts under reduced pressure until the combined elution parts are dry for later use.
And 4, carrying out chromatographic separation on the product obtained in the step 3 by using a pretreated ODS (octadecylsilane chemically bonded silica) column, carrying out gradient elution by using methanol-water to obtain a plurality of elution parts, detecting by using a thin-layer chromatography, developing, and concentrating each developed elution part under reduced pressure until the elution part is dried to obtain a concentrate for later use.
And 5, separating and preparing the new compound obtained in the step 4 by HPLC (high performance liquid chromatography), and carrying out isocratic elution by using methanol-0.1% formic acid as a mobile phase to finally obtain a compound, namely, oleracene F.
The pretreatment process of the ODS comprises the steps of soaking in methanol for 24 hours, loading on a column, washing with methanol until no turbidity exists in dropping water, and balancing with an initial mobile phase.
Compared with the prior art, the invention has the beneficial effects.
The separation and pharmacological activity research of the novel purslane compound is not reported in the journal of the prior paper; the invention provides a new compound from purslane and an extraction and separation method for the new compound, wherein the new compound is successfully extracted and separated by adopting alcohol extraction, silica gel column chromatography, polyamide column, ODS medium-pressure column and HPLC (high performance liquid chromatography). Therefore, the novel compound and the salt and the derivative thereof can be used as a lead for synthesizing other compounds, as well as raw materials for developing new medicines and researching pharmacological activity, and can also be used for preparing anti-inflammatory and antioxidant medicines.
Drawings
FIG. 1 is a UV spectrum of the novel compound, oleracene F.
FIG. 2 is an infrared spectrum of the novel compound, oleracene F.
FIG. 3 is a high resolution mass spectrum of the novel compound, oleracene F.
FIG. 4 Oleacone F, a novel compound of the present invention1H-NMR spectrum chart.
FIG. 5 novel Compound oleracene F of the invention13C-NMR spectrum chart.
FIG. 6 is a nuclear magnetic resonance carbon spectrum (DEPT) spectrum of the novel compound oleracene F of the present invention.
FIG. 7 nuclear magnetic resonance of novel Compound oleracene F of the present invention1H-1HCOSY spectrum.
FIG. 8 shows a nuclear magnetic resonance HMBC spectrum of the novel compound, oleracene F.
FIG. 9 shows the NMR HSQC spectrum of the novel compound oleracene F of the present invention.
Detailed Description
The present invention will be further described with reference to the following specific examples.
Example 1.
The present invention provides novel compounds of formula C18H16O5Designated as oleracene F, has the chemical structural formula:
the new compound is named oleracene F according to the structure, and table 1 is the nuclear magnetic data of the new compound:1H-NMR of13C-NMR in DMSO.
Table 1: nuclear magnetic data of the novel compound, oleracene F.
Structural characterization see FIGS. 1-9.
Oleracone F: yellow powder, readily soluble in methanol, slightly soluble in chloroform. After the sample is applied to the silica gel thin layer plate, the spot of the ferric trichloride test solution is sprayed to be cyan. UV (MeOH) lambdamax:281,255,205nm。IR vmax2919,2850,1647,1600,1456,1378,1294,1209,1169,1081,834,756cm-1. HRESI (+) TOFMS gave M/z 313.1066[ M + H]+Has an excimer ion peak of 312.3210 molecular weight. Bonding of1H-NMR，13C-NMR and DEPT data, presuming that the possible molecular formula of the compound is C18H16O5The unsaturation degree was 11.13The C-NMR spectrum and DEPT spectrum showed 18 carbon signals, respectively 2 CH3(delta: 56.0; 55.9), 1 CH2(delta: 25.1), 7 CH (delta: 92.9; 96.0; 115.2; 118.8; 127.2; 130.0; 151.1), 8 quaternary carbons (one carbonyl carbon, delta: 174.9; four double-bonded carbons to O, delta: 163.5; 160.4; 159.5; 155.1; three double-bonded carbons, delta: 125.3; 123.4; 108.3).
1The H-NMR spectrum showed a reactive H signal delta 9.49(1H, bs), indicating the possible presence of a hydroxyl group. 2 methyl signals, δ 3.84(3H, s), δ 3.80(3H, s); 1 methylene signal, δ 3.51(2H, s); the 7 methine signals are δ 6.47(1H, d, J ═ 2.4), δ 6.60(1H, d, J ═ 2.3), δ 6.68(1H, brtd, J ═ 7.4,1.1), δ 6.78(1H, dd, J ═ 8.1,1.1), δ 7.00(1H, brtd, J ═ 7.6,1.6), δ 7.06(1H, dd, J ═ 7.5,1.6), δ 7.81(1H, s). According to an H-H COSY spectrum, H delta 3.51 in methylene is coupled with methine delta 7.86; two methines δ 6.47 and δ 6.60 are coupled; methine groups δ 6.68, δ 6.78, δ 7.00, δ 7.03 are coupled to each other, indicating the presence of a benzene ring. The correlation peaks according to the HMBC spectrum show that H-6 and H-8 are respectively coupled with C-7 and C-10, and H-6 and H-8 are coupled with each other, which shows that the correlation is related with C-7 and C-10; h delta 3.84 in the methoxy group is coupled with C-7, and C-7 (delta 163.5) is positioned in a low field region, which indicates that the methoxy group is connected with O, and indicates that the methoxy group is connected with C-7 on a benzene ring; h delta 3.80 in methoxy is coupled with C-5, and C-5 (delta 160.4) positionIn the low field region, the connection with O is prompted, which shows that the methoxyl is connected with C-5 on the benzene ring; h-8 is coupled with C-9, H-6 is coupled with C-5, and C-9 (delta 157.73) is positioned in a low field region and prompts connection with O; h-2, H-11 are coupled to each other, and H-2, H-11 are coupled to C-3, indicating that C-3 is involved; c-2 (delta 151.1) is located in a low field region, prompting connection with O, and meanwhile, H-2 is coupled with C-9, which shows that C-2 is connected with O in the middle of C-9; h-2, H-11 are coupled with C-4 carbonyl C, which indicates that C-4 is related. H-3 ', H-4 ', H-5 ' and H-6 ' are coupled with each other, wherein H-3 ', H-5 ' and C-1 ' are coupled, H-3 ', H-4 ', H-6 ' and C-2 ' are coupled, indicating the existence of benzene ring and the ortho-position substitution of C-1 ' and C-2 '; wherein C-2 '(delta 155.1) is in the low field region, indicating that it is linked to O, indicating that C-2' is linked to a hydroxyl group; h-11 is coupled to C-1 ', C-2 ', C-6 ', indicating a relationship with C-1 ', C-2 ', C-6 ', and summarizing that C-11 is coupled to C-1 '. From the above information, the novel compounds can be identified as having the above structure.
The method for extracting and separating the new compound comprises the following specific steps.
Step 1: weighing 80kg of dry herba Portulacae, reflux-extracting with 50% ethanol dosage (v/v) 10 times of the medicinal materials twice (2 hr each time), recovering ethanol under reduced pressure, and cooling to room temperature to obtain medicinal liquid.
Step 2: evaporating the liquid medicine obtained in the step 1 to dryness, performing chromatographic separation by using a silica gel column, isocratically eluting by using ethyl acetate (120L), wherein the silica gel is 100-200 meshes, and recovering the ethyl acetate to obtain an extract under reduced pressure below 40 ℃ to obtain an ethyl acetate extract.
And step 3: separating the ethyl acetate extract obtained in the step 2 by using a polyamide column, performing gradient elution by using ethanol-water (0/100, 30/70, 50/50, 70/30, 100/0, v/v), evaporating 50% ethanol, performing chromatographic separation by using a silica gel column, wherein the silica gel is 200-300 meshes, performing gradient elution by using ethyl acetate-methanol (5:1, 2:1, 1:2, v: v) in sequence to obtain 15 parts (15 bottles are obtained in total, each bottle is 400mL), detecting by using a thin-layer chromatography, developing, combining the developed 1-3 elution parts, and concentrating the combined 1-3 parts at the temperature of below 40 ℃ under reduced pressure until the parts are dry for later use.
And 4, step 4: and (3) performing pretreated ODS (octadecylsilane chemically bonded silica) medium-pressure column chromatography separation on the product obtained in the step (3), wherein the granularity of the filler is 20-40 mu m, performing gradient elution (pressurizing to ensure that the flow rate is 1mL/min and the temperature is room temperature) by using methanol-water (84/16, 93/7, 97/3, 100/0, v/v) to obtain 10 parts (namely performing gradient elution to obtain 10 bottles with 200mL in each bottle), detecting by using thin-layer chromatography, developing, reserving the developed 1-5 parts, and concentrating under reduced pressure below 50 ℃ until the parts are dry for later use to obtain a new compound. The pretreatment process of the ODS comprises the steps of soaking in methanol for 24 hours, loading on a column, washing with methanol until no turbidity exists in dropping water, and balancing with an initial mobile phase.
And 5: the new compound obtained in step 4 was prepared by HPLC separation with methanol: 0.1% formic acid (50: 50, v/v) is used as a mobile phase, the detection wavelength is 210nm and 280nm, the new compound is obtained by separation and preparation, and the purity measured by a normalization method is 90-99%.
The novel compounds of the present invention have anti-inflammatory properties.
1. The main material.
1.1, drugs and reagents: the new compound used in the experiment is prepared by the method, the purity of the new compound is 90-99%, the new compound is precisely weighed and diluted by DMSO to be a solution required by each dosage group. DMEM high-glucose medium, fetal bovine serum (Hyclone, usa); penicillin, streptomycin (Hangzhou Sijiqing Co.); LPS (Sigma, usa); IL-6, TNF-alpha, PGE2ELISA kit of (A) (Cayman, USA); cell lysate, Griess reagent (bi yun tian biotechnology limited).
1.2 cell lines: RAW264.7 macrophages (us ATCC cell bank).
1.3 grouping: the test group was divided into a control group, an LPS group and an experimental group.
2 experimental methods.
2.1 cell culture, DMEM high-sugar medium, with addition of l 0% fetal bovine serum, l% antibiotics (100U/mL penicillin and 100. mu.g/mL streptomycin), 37.5% CO2Culturing in an incubator.
2.2MTT colorimetric method for determining cell viability, and respectively inoculating RAW264.7 macrophage in logarithmic growth phase into 96-wellCell density in the plates was 1X 104one/mL, 100. mu.L per well, temperature 37 ℃, 5% CO2After overnight culture under the condition, the experimental group is added with the novel compound oleracene F (1-50 mu M) of the invention with different concentrations, LPS with the final concentration of 1 mu g/mL is respectively added into the LPS group and the experimental group after 1h incubation, a zero-adjusting group (culture solution containing DMSO solvent) is additionally arranged, each group is provided with 3 multiple holes, and the influence on cells after adding the medicament is examined. After culturing the above groups of cells for 24 hours, 5mg/mL MTT 20. mu.L was added to each well of cells at 37 ℃ with 5% CO2After incubation for 4h, terminating the culture, absorbing the liquid in the wells, adding 100 μ L of dimethyl sulfoxide (DMSO) into each well, oscillating for 10min to dissolve the intracellular crystal, and measuring the light absorption value of each well at 570nm wavelength of an enzyme-labeling instrument.
2.3 measurement of NO content by Griess method, the inhibitory effect of the novel compound of the present invention on the NO production of LPS-induced mouse macrophage RAW264.7 was examined. Mouse macrophage RAW264.7 passage, culturing in high glucose cell culture medium DMEM containing 10% fetal calf serum, adding the new compound of the present invention oleocone F (1-20 μ M) with different concentrations into experimental group, and culturing at 37 deg.C and 5% CO2After incubation for 1h under conditions, inflammatory responses were induced with LPS (final concentration 1. mu.g/mL), and after 24h supernatants were collected and 3 wells were repeated for each group. The Griess method measures the content of NO in cell supernatant, and the influence of the novel compound on the NO release of LPS-induced RAW264.7 cells is reflected according to different concentrations so as to reflect the NO level.
2.4 measurement of inflammatory factors IL-6, TNF-alpha and inflammatory mediators PGE by ELISA2: RAW264.7 macrophages in logarithmic growth phase were seeded in 24-well culture plates at a cell density of 1X 105one/mL, 1mL per well, temperature 37 ℃, 5% CO2After incubation overnight under these conditions, the experimental groups were incubated with the novel compound oleacone F (1-20. mu.M) for 1h, LPS (final concentration of 1. mu.g/mL) was added to each well, and incubation was carried out for 24h, with 3-well replicates for each group of treatments. ELISA method for measuring IL-6, TNF-alpha and PGE secreted by RAW264.7 macrophage after treatment of purslane-derived novel compound2The content of (a).
3, experimental results.
The experimental results show that the invention is specially combinedThe compound has no influence on proliferation of macrophage RAW264.7 induced by LPS, and is safe and nontoxic; and can effectively inhibit excessive inflammatory cytokines IL-6, TNF-alpha and inflammatory mediators NO and PGE generated by macrophage RAW264.7 induced by LPS2And is concentration dependent.
The results of the cell relative survival experiments are shown in table 2.
Table 2: effect of the invention on relative survival of RAW264.7 macrophages.
Note:*P<0.05 compared with the control group (significant difference in the high concentration group),
the results of the experiments for determining the NO content by the Griess method are shown in Table 3.
Table 3: the effect of the present invention on LPS-induced NO release from RAW264.7 cells (mean ± sd, n ═ 3).
Note:*P<0.05 compared with the control group,#P<0.05 compared to the LPS group.
ELISA method for measuring inflammatory factors IL-6, TNF-alpha and inflammatory mediator PGE2The results are shown in Table 4.
Table 4: the invention relates to IL-6, TNF-alpha and PGE secreted by RAW264.7 cells induced by LPS2Influence of the content (mean ± sd, n ═ 3).
Note:*P<0.05 compared with the control group,#P<0.05 compared to the LPS group.
The novel compounds of the present invention have antioxidant activity.
1 main material.
1.1 drugs and reagents: the new compound used in the experiment is prepared by the method, the purity is 90-99%, the new compound is precisely weighed and diluted by methanol to the solution required by each dosage group. DPPH (1, 1-diphenyl-2-picrylhydrazyl radical) (Sigma-Fluka corporation); BHA (t-butyl hydroxyanisole) (shanghai auspicious science ltd); methanol, pure chromatography (Changtaixing, Inc.).
1.2 grouping: control, experimental, blank.
2. Experimental methods.
The ability to eliminate DPPH free radicals was determined colorimetrically, and 1mL of DPPH solution (126.80. mu.M) was added to a 4mL cuvette and 1mL of sample solutions of different concentrations (8.01, 16.02, 32.04, 48.06, 64.08. mu.M) were added to the sample set; adding 1mL of methanol solution into a 4mL cuvette in the control group, and then adding 1mL of sample solutions with different concentrations; the blank was prepared by adding 1mL of DPPH solution to a 4mL cuvette and then adding 1mL of methanol solution. Mixing the three groups, standing at room temperature in dark for 5min, and measuring light absorption value at 517 nm. Three average determinations were made for each sample, and the positive controls were BHA solutions of different concentrations. The DPPH free radical clearance rate of the sample is calculated according to the following formula, and the free radical clearance rate IC is further calculated50The value is obtained.
DPPH clearance (%) < 1- (A)1－A2)/A0X 100%, wherein A0Absorbance values for the blank set;
A1is the absorbance value of the sample set; a. the2Absorbance values for the control group.
3. And (5) experimental results.
The experimental result shows that the novel compound has the effect of removing DPPH free radicals, and the removal rate is obviously increased along with the increase of the concentration of the medicament. Novel compounds of the invention are directed to DPPH free radical IC50The values are shown in Table 5.
Table 5 DPPH radical scavenging action of the novel compounds of the invention.
| Group of | IC50(μM) |
| BHA | 56.96 |
| Oleracone F | 17.78 |
In conclusion, the invention provides the special compound and the extraction and separation method thereof, the new compound is successfully separated and obtained by sequentially adopting 50% ethanol reflux extraction, silica gel column chromatography, polyamide column chromatography and ODS medium-pressure column separation and purification, the method is simple, convenient, rapid and environment-friendly, the purity of the compound separated by the method is higher, and the obtained compound has unique chemical structure, is extracted from the common traditional Chinese medicine purslane and has anti-inflammatory and anti-oxidation effects, so the special compound and the salt and the derivative thereof can be used as natural products to develop new traditional Chinese medicines, and have wide prospects.
Claims (1)
1. The extraction and separation method of the compound Oleracone F in the purslane is characterized in that the chemical structural formula of the compound is shown in the specification
The method for extracting and separating the compound Oleracone F in the purslane comprises the following specific steps:
step 1: weighing 80kg of dry purslane medicinal material, performing reflux extraction by adopting 50% ethanol, performing reflux extraction twice with the dosage v/v of the 50% ethanol being 10 times of that of the medicinal material, performing 2 hours each time, recovering ethanol under reduced pressure, and cooling to room temperature to obtain liquid medicine for later use;
step 2: evaporating the liquid medicine obtained in the step 1 to dryness, performing chromatographic separation by using a silica gel column, and performing isocratic elution by using ethyl acetate of 120L, wherein the silica gel is 100-200 meshes, and recovering the ethyl acetate to obtain an extract under reduced pressure below 40 ℃ to obtain an ethyl acetate extract;
and step 3: separating the ethyl acetate extract obtained in the step 2 by using a polyamide column, and performing gradient elution by using ethanol-water, wherein the eluent ratio is 0/100, 30/70, 50/50, 70/30, 100/0 and v/v; evaporating 50% ethanol to dryness, and separating by silica gel column chromatography, wherein the silica gel is 200-300 meshes, and sequentially performing gradient elution by using ethyl acetate-methanol, and the eluent ratio is 5:1, 2:1, 1:2, v: v; detecting by thin layer chromatography, developing, mixing the developed eluate parts, and concentrating the combined eluate parts at 40 deg.C under reduced pressure to dry;
and 4, step 4: separating the product obtained in the step 3 by pretreated ODS medium-pressure column chromatography, wherein the filler particle size is 20-40 μm, and performing gradient elution by using methanol-water, wherein the eluent ratio is 84/16, 93/7, 97/3, 100/0 and v/v; detecting by thin layer chromatography, developing color, retaining the developed part, and concentrating under reduced pressure below 50 deg.C to dry to obtain new compound; the ODS pretreatment process comprises the steps of soaking in methanol for 24 hours, loading on a column, washing with methanol until no turbidity exists in dropping water, and balancing with an initial mobile phase;
and 5: the new compound obtained in step 4 was prepared by HPLC separation with methanol: 0.1% formic acid 50: 50, v/v is taken as a mobile phase, the detection wavelength is 210nm and 280nm, the compound Oleracone F is obtained by separation, and the purity measured by a normalization method is 90-99%.
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| CN110294733B (en) * | 2019-04-03 | 2021-09-07 | 辽宁中医药大学 | Peroxide bond-containing compound Oleracone I in purslane, and extraction separation method and application thereof |
| CN109824685B (en) * | 2019-04-03 | 2021-03-23 | 辽宁中医药大学 | Compound oleracene G in purslane, extraction and separation method and application thereof |
| CN110194755B (en) * | 2019-04-03 | 2022-05-13 | 辽宁中医药大学 | Compound Oleracone H in purslane, extraction and separation method and application thereof |
| CN110305094B (en) * | 2019-07-16 | 2022-06-17 | 辽宁中医药大学 | Two flavonoid compounds in purslane and extraction and separation method and application thereof |
| CN111217773B (en) * | 2020-03-12 | 2022-05-13 | 辽宁中医药大学 | Furan ring compound in purslane and extraction and separation method and application thereof |
| CN115385884B (en) * | 2022-08-23 | 2023-04-25 | 辽宁中医药大学 | Extraction and separation method of neochronol in purslane and application thereof |
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