CN108017554A - A kind of method that ceramide is extracted in the ballstone algae from ocean - Google Patents
A kind of method that ceramide is extracted in the ballstone algae from ocean Download PDFInfo
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- CN108017554A CN108017554A CN201810043725.7A CN201810043725A CN108017554A CN 108017554 A CN108017554 A CN 108017554A CN 201810043725 A CN201810043725 A CN 201810043725A CN 108017554 A CN108017554 A CN 108017554A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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Abstract
The invention discloses one kind from ocean ballstone algae（Emiliania huxleyi）It is middle extraction ceramide method, successively with：Extracted with petroleum ether；Chromatographed with reverse phase silica gel column；Chromatographed with sephadex column Sephadex LH 20；Chromatographed with normal phase silicagel column；With the PTLC methods prepared ceramide is extracted from the ballstone algae of ocean.The present invention has carried out separation, purifying to the ceramide of ocean ballstone algae petroleum ether phase extract first, which is 62.64% to the inhibiting rate of liver cancer cells Hep G2, lays the foundation for follow-up large-scale production ceramide.
Description
Technical field
The present invention relates to ceramide is extracted in the technical field of biological agent, more particularly to a kind of ballstone algae from ocean
Method.
Background technology
Ocean ballstone algae (Coccolithophores) is the miniature phytoplankton of a kind of single-cell sea, is under the jurisdiction of and determines whip algae
Door (Haptophyta=Prymnesiophyta) Haptophyceae (Prymnesiophyceae).In the ballstone algae metabolite of ocean
Rich in various bioactivators, such as docosahexaenoic acid (DHA), polyketides, especially marine microalgae cell
Middle total lipid content reaches as high as the 50% of dry cell weight, and wherein sphingolipid content can reach the 0.914% of dry cell weight, and wherein
99% is ceramide.Ceramide has the biological function such as well antibacterial, anti-inflammatory, antitumor, in food, cosmetics and doctor
Medicine field has broad application prospects.But the current research in relation to ocean ballstone algae ceramide type material sphere is less.
In view of this, the present inventor studies and devises a kind of method that ceramide is extracted in ballstone algae from ocean, this
Thus case produces.
The content of the invention
It is an object of the invention to provide a kind of method that ceramide is extracted in ballstone algae from ocean, it is intended to passes through thin layer
The methods of chromatography, silica gel column chromatography, gel filtration chromatography method, preparative thin layer PTLC, mutually extracts ocean ballstone algae petroleum ether
The ceramide of thing is separated, purified, in order to follow-up large-scale production ceramide.
In order to solve above-mentioned purpose, the technical solution adopted by the present invention is as follows：
In a kind of ballstone algae from ocean extract ceramide method, successively with：Extracted with petroleum ether；With anti-phase silicon
Rubber column gel column is chromatographed；Chromatographed with sephadex column Sephadex LH-20；Chromatographed with normal phase silicagel column；Use PTLC
The method of preparation extracts ceramide from the ballstone algae of ocean.
As the preferred embodiment of embodiment, the method for said extracted ceramide specifically includes following steps：
Step 1: prepare ocean ballstone algae petroleum ether phase extract：Extraction processing is carried out by extractant of petroleum ether, is merged
Extract, is concentrated under reduced pressure to give ocean ballstone algae petroleum ether phase extract；Ballstone algae grows to stationary phase for ocean, harvests, freezing
It is dry to obtain ocean ballstone algae powder, with the alcohol steep of mass fraction 75%, ethanol extract is obtained, adds isometric oil
Ether and water, extract repeatedly, collect petroleum ether phase, merge, are concentrated under reduced pressure into dry, acquisition ocean ballstone algae petroleum ether phase extract；
Step 2: reversed-phase silica gel column chromatography prepares ceramide crude product：The ocean ballstone algae petroleum ether of acquisition is mutually extracted
Thing carries out Image processing with reverse phase silica gel column, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining ceramide crude product；
As the preferred embodiment of embodiment, ballstone algae petroleum ether phase extract suitable pure methanol of analysis in ocean is dissolved
Afterwards, reversed-phase silica gel column chromatography is carried out；It is successively 95 with volume ratio:5；90:10；85:15；80:20；70:30；60:40；50:50；
40:60 ethyl acetate/petroleum ether eluent is eluted, each gradient elution 100mL, flow control 2mL/min, often
10mL collects 1 pipe, and 60 DEG C of vacuum drying, tentatively analyze effluent with TLC, merges the segmentation of ceramide high concentration flow, and decompression is dense
It is reduced to dry, acquisition ceramide crude product；
Step 3: sephadex column Sephadex LH-20 chromatographies prepare fine work of ceramide：By the god of acquisition
Image processing is carried out with sephadex column Sephadex LH-20 through crude amide, is collected, is detected, merges, is concentrated under reduced pressure into
It is dry, obtain fine work of ceramide；
As the preferred embodiment of embodiment, after above-mentioned ceramide crude product is dissolved with proper amount of methanol, upper sephadex
Column Sephadex LH-20, are 1 with volume ratio:1 chloroform：Methanol is eluted, 6-10 seconds/drop of flow control, using automatic
Collector collects each cut, and a pipe is collected per 30min, tentatively analyzes effluent with TLC, merges the cut of 132 to 146 pipes, subtracts
Pressure is concentrated to dryness, and obtains fine work of ceramide；
Step 4: normal-phase silica gel column chromatography prepares the secondary fine work of ceramide：By fine work of ceramide of acquisition with
Normal phase silicagel column carries out Image processing, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining the secondary fine work of ceramide；
Fine work of ceramide is mixed into sample by normal-phase silica gel column chromatography with silica white, silica gel after petroleum ether saturation with filling
Column, is eluted after sample upper prop, 6-10 seconds/drop of flow control with petroleum ether and ethyl acetate, petroleum ether and ethyl acetate
Volume ratio is 1:1, cut is collected, merges 10-16 pipes, is concentrated under reduced pressure into dry, the acquisition secondary fine work of ceramide；
Step 5: PTLC prepares ceramide：The secondary fine work of the ceramide of acquisition is subjected to PTLC, point sample, expansion, are scraped
Plate, sample recycling, is stored in -20 DEG C, obtains ceramide sterling；
The secondary fine work of ceramide is passed through into PTLC, finally obtains ceramide；Using High Performance Thin Layer Chromatography plate, in volume
Than for 19:0.9:It is unfolded in 0.1 chloroform/methanol/acetic acid solvent, is sprayed and developed the color using color developing agent, is scraped with blade middle
Part, merges, is dissolved with methanol, and high speed centrifugation, collects supernatant, and is concentrated under reduced pressure into dry, finally obtains ceramide.
As the preferred embodiment of embodiment, the color developing agent is that alizarin-ethanol that quality volume fraction g/mL is 1% is molten
Liquid.
A kind of application of ceramide in liver cancer suppression medicament is prepared.
Since present system employs above-mentioned technical solution so that this practicality has the advantages that：This hair
Bright the methods of using thin layer chromatography, silica gel column chromatography, gel filtration chromatography method, preparative thin layer first, is to ocean ballstone algae stone
The ceramide of oily ether phase extract has carried out separation, purifying, to lay the foundation for follow-up large-scale production ceramide.
Brief description of the drawings
Fig. 1 is the figure of ceramide TLC of the present invention；
Fig. 2 is the structure chart of ceramide of the present invention；
The nuclear-magnetism spectrum that Fig. 3 is the 1H-NMR of the compounds of this invention ceramide；
Fig. 4 is that the 13C-NMR nuclear-magnetisms of the compounds of this invention ceramide are composed；
Fig. 5 is the high resolution mass spectrum figure of the compounds of this invention ceramide.
Embodiment
The method that ceramide is extracted in a kind of ballstone algae from ocean of embodiment 1
Present invention is disclosed in a kind of ballstone algae from ocean extract ceramide method, successively with：Carried out with petroleum ether
Extraction；Chromatographed with reverse phase silica gel column；Chromatographed with sephadex column Sephadex LH-20；With normal phase silicagel column into
Row chromatography；With the PTLC methods prepared ceramide is extracted from the ballstone algae of ocean.
As the preferred embodiment of embodiment, the method for said extracted ceramide specifically includes following steps：
Step 1: prepare ocean ballstone algae petroleum ether phase extract：Extraction processing is carried out by extractant of petroleum ether, is merged
Extract, is concentrated under reduced pressure to give ocean ballstone algae petroleum ether phase extract；(ballstone algae grows to stationary phase for ocean, harvests, freezing
It is dry to obtain ocean ballstone algae powder 18.6706g, ethanol extract is obtained with 75% alcohol steep, adds isometric oil
Ether and water, extract repeatedly, collect petroleum ether phase, merge, are concentrated under reduced pressure into dry, acquisition ocean ballstone algae petroleum ether phase extract
5.2613g
Step 2: reversed-phase silica gel column chromatography prepares ceramide crude product：The ocean ballstone algae petroleum ether of acquisition is mutually extracted
Thing carries out Image processing with reverse phase silica gel column, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining ceramide crude product；
After the analytically pure methanol that 5.2613g oceans ballstone algae petroleum ether phase extract is tried one's best few with volume is dissolved, into
Row reverse phase silica gel (180g) column chromatography；Successively with 95:5；90:10；85:15；80:20；70:30；60:40；50:50；40:60
(v/v) ethyl acetate/petroleum ether eluent is eluted, each gradient elution 100mL, and flow control is 6-10 seconds/drop, often
10mL collects 1 pipe, and 60 DEG C of vacuum drying, tentatively analyze effluent with TLC, merges the segmentation of ceramide high concentration flow, and decompression is dense
It is reduced to dry, acquisition ceramide crude product；
Step 3: sephadex column Sephadex LH-20 chromatographies prepare fine work of ceramide：By the sea of acquisition
Foreign ballstone algae ceramide crude product carries out Image processing with sephadex column Sephadex LH-20, collects, detect, merge,
It is concentrated under reduced pressure into dry, obtains fine work of ceramide；
After ceramide is dissolved with a small amount of methanol, upper sephadex column Sephadex LH-20, use chloroform:Methanol
(1:1) eluted, 6-10 seconds/drop of flow control, each cut is collected using automatic collector, a pipe is collected per 30min, tentatively
Effluent is analyzed with TLC, merges the cut of 132 to 146 pipes, is concentrated under reduced pressure into dry, acquisition fine work of ceramide；
Step 4: normal-phase silica gel column chromatography prepares the secondary fine work of ceramide：By fine work of ceramide of acquisition with
Normal phase silicagel column carries out Image processing, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining the secondary fine work of ceramide；
Fine work of ceramide is mixed into sample by normal-phase silica gel column chromatography with silica white, silica gel after petroleum ether saturation with filling
Column, is eluted with petroleum ether and ethyl acetate after sample upper prop, collects petroleum ether:Ethyl acetate=1:1 cut, merges
10-16 is managed, and is concentrated under reduced pressure into dry, the acquisition secondary fine work of ceramide；
Step 5: PTLC prepares ceramide：The secondary fine work of the ceramide of acquisition is subjected to PTLC, point sample, expansion, are scraped
Plate, sample recycling, is stored in -20 DEG C, obtains ceramide sterling；
The secondary fine work of ceramide is passed through into PTLC, finally obtains ceramide；Using High Performance Thin Layer Chromatography plate, in chlorine
Imitative/methanol/acetic acid (19:0.9:0.1) it is unfolded in solvent, 1% alizarin, one ethanol carries out spraying colour developing, and the results are shown in Figure 1,
Center section is scraped with blade, merges, is dissolved with methanol, high speed centrifugation, collects supernatant, and is concentrated under reduced pressure into dry, finally obtains
Ceramide.
The structure of the ceramide of above-mentioned acquisition is parsed using magnetic nuclear resonance method, as shown in Figure 2-5, is respectively
The structure chart of ceramide, the nuclear-magnetism spectrum of 1H-NMR, the nuclear-magnetism spectrum of 13C-NMR, high resolution mass spectrum figure.As shown in table 1, it is chemical combination
The spectral data of thing ceramide.
The spectral data of 1 compound ceramide of table
| No | 13C | 1H |
| 1 | 14.1 | 0.92 |
| 2 | 22.7 | 1.39 |
| 3 | 32.2 | 2.11 |
| 4-20 | 29.7 | 1.32 |
| 21 | 36.9 | 2.27 |
| 22 | 173.9 | ‐ |
| 23 | 54.5 | 3.99 3.75 |
| 24 | 62.5 | 3.96 |
| 25 | 74.7 | 4.36 |
| 26 | 128.8 | 5.58 |
| 27 | 134.4 | 5.83 |
| 28 | 32.3 | 2.07 |
| 29-37 | 29.7 | 1.30 |
| 38 | 25.8 | 1.68 |
| 39 | 22.7 | 1.39 |
| 40 | 14.1 | 0.92 |
| 6.26C25-OH |
2 cytotoxic activity of embodiment is tested
A. cell cryopreservation：
Prepare 10%DMSO calf serum frozen stock solutions；Take the logarithm the phase growth LO2, Hep G2 cells, disappeared with trypsase
Change monolayer growth cell；1000rpm centrifuges 5min；Supernatant is removed, adds new frozen stock solution；It is sub-packed in cryopreservation tube, has marked name
Claim, the time；Cryopreservation tube equipped with cell is put into -20 DEG C of refrigerator 2h, is then placed in -70 DEG C of refrigerator overnights, rapid take out is frozen
Pipe is deposited, moves into liquid nitrogen and freezes.
B. cell recovery：
Cell cryopreservation tube is taken out from liquid nitrogen, is thawed rapidly in 37 DEG C of water-baths, controls this process within 1 minute；Inhale
Go out cell suspending liquid into centrifuge tube and add 10 times of culture mediums, gently mix；1000rpm centrifuges 5min；Supernatant is outwelled, weight
Once, blood counting chamber counts for after backwashing, stands the 37 DEG C of cultures of CO2 incubators；Next day replaces culture medium and continues to cultivate.
C.MTT methods detect cell viability：
The selected tumour cell of this experiment is liver cancer cell lines Hep G2 and normal liver cell LO2.Logarithm is digested with pancreatin
The tumour cell in growth period, is counted with blood counting chamber after adding fresh medium, 96 holes is inoculated in after adjusting cell concentration
Plate, is placed in culture 24h in 37 DEG C of CO2 incubators.Ceramide is configured to the liquid that concentration is 20 μ g/mL, each concentration three
A parallel laboratory test, using cis-platinum as positive control.20 μ L MTT solution, 37 DEG C of culture 4h are added in per hole.Supernatant is removed, is added per hole
Enter 150 μ L of DMSO.When 37 DEG C of shaking table cultures 2 are small, optical density (OD490) value is measured at microplate reader 490nm, calculates inhibiting rate.
Inhibiting rate %=(1- experimental groups mean OD value/control group mean OD value) × 100%.
Inhibiting rate of 2 ceramide of table to LO2 (normal) and Hep G2 (liver cancer) cell
As shown in table 2, cytotoxic activity experiment shows that ceramide is stronger to the inhibition of Hep G2 liver cancer cells,
Up to 62.64%.
The above, is only present pre-ferred embodiments, therefore cannot limit the scope implemented of the present invention according to this, i.e., according to
The equivalent changes and modifications that the scope of the claims of the present invention and description are made, all should still belong in the range of the present invention covers.
Claims (7)
1. the method for ceramide is extracted in a kind of ballstone algae from ocean, it is characterised in that：Successively with：Extracted with petroleum ether
Take；Chromatographed with reverse phase silica gel column；Chromatographed with sephadex column Sephadex LH-20；Carried out with normal phase silicagel column
Chromatography；With the PTLC methods prepared ceramide is extracted from the ballstone algae of ocean.
2. the method for ceramide is extracted in a kind of ballstone algae from ocean as claimed in claim 1, it is characterised in that：It is above-mentioned to carry
The method of ceramide is taken to specifically include following steps：
Step 1: prepare ocean ballstone algae petroleum ether phase extract：Extraction processing is carried out by extractant of petroleum ether, merges extraction
Liquid, is concentrated under reduced pressure to give ocean ballstone algae petroleum ether phase extract；Ballstone algae grows to stationary phase for ocean, harvests, freeze-drying
Obtain ocean ballstone algae powder, with the alcohol steep of mass fraction 75%, obtain ethanol extract, add isometric petroleum ether and
Water, extracts repeatedly, collects petroleum ether phase, merges, is concentrated under reduced pressure into dry, acquisition ocean ballstone algae petroleum ether phase extract；
Step 2: reversed-phase silica gel column chromatography prepares ceramide crude product：By the ocean ballstone algae petroleum ether phase extract of acquisition with
Reverse phase silica gel column carries out Image processing, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining ceramide crude product；
Step 3: sephadex column Sephadex LH-20 chromatographies prepare fine work of ceramide：By the neural acyl of acquisition
Amine crude product carries out Image processing with sephadex column Sephadex LH-20, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining
To fine work of ceramide；
Step 4: normal-phase silica gel column chromatography prepares the secondary fine work of ceramide：By fine work of ceramide of acquisition with positive
Silicagel column carries out Image processing, collects, and detects, merges, being concentrated under reduced pressure into dry, obtaining the secondary fine work of ceramide；
Step 5: PTLC prepares ceramide：The secondary fine work of the ceramide of acquisition is subjected to PTLC, point sample, expansion, scraper plate,
Sample recycles, and is stored in -20 DEG C, obtains ceramide sterling.
3. the method for ceramide is extracted in a kind of ballstone algae from ocean as claimed in claim 2, it is characterised in that：The step
In rapid two, by ocean ballstone algae petroleum ether phase extract with after the pure methanol dissolving of suitable analysis, reversed-phase silica gel column chromatography is carried out；
It is successively 95 with volume ratio:5；90:10；85:15；80:20；70:30；60:40；50:50；40:60 ethyl acetate/petroleum ether
Eluent is eluted, each gradient elution 100mL, and flow control 2mL/min, every 10 mL collect 1 pipe, and 60 DEG C of vacuum are done
It is dry, effluent tentatively is analyzed with TLC, merges the segmentation of ceramide high concentration flow, is concentrated under reduced pressure into dry, it is thick to obtain ceramide
Product.
4. the method for ceramide is extracted in a kind of ballstone algae from ocean as claimed in claim 2, it is characterised in that：The step
In rapid three, after above-mentioned ceramide crude product is dissolved with proper amount of methanol, upper sephadex column Sephadex LH-20, use volume
Than for 1:1 chloroform：Methanol is eluted, and 6-10 seconds/drop of flow control, collects each cut, often using automatic collector
30min collects a pipe, tentatively analyzes effluent with TLC, merges the cut of 132 to 146 pipes, is concentrated under reduced pressure into dry, acquisition nerve
Fine work of acid amides.
5. the method for ceramide is extracted in a kind of ballstone algae from ocean as claimed in claim 2, it is characterised in that：The step
In rapid four, fine work of ceramide is mixed into sample by normal-phase silica gel column chromatography with silica white, silica gel after petroleum ether saturation with filling
Column, is eluted after sample upper prop, 6-10 seconds/drop of flow control with petroleum ether and ethyl acetate, petroleum ether and ethyl acetate
Volume ratio is 1:1, cut is collected, merges 10-16 pipes, is concentrated under reduced pressure into dry, the acquisition secondary fine work of ceramide.
6. the method for ceramide is extracted in a kind of ballstone algae from ocean as claimed in claim 2, it is characterised in that：The step
In rapid five, the secondary fine work of ceramide is passed through into PTLC, finally obtains ceramide；Using High Performance Thin Layer Chromatography plate, in volume
Than for 19:0.9:It is unfolded in 0.1 chloroform/methanol/acetic acid solvent, is sprayed and developed the color using color developing agent, is scraped with blade middle
Part, merges, is dissolved with methanol, and high speed centrifugation, collects supernatant, and is concentrated under reduced pressure into dry, finally obtains ceramide.
7. the method for ceramide is extracted in a kind of ballstone algae from ocean as claimed in claim 6, it is characterised in that：It is described aobvious
Toner is alizarin-ethanol solution that quality volume fraction g/mL is 1%.
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| CN110438177A (en) * | 2019-08-12 | 2019-11-12 | 三原利华生物技术有限公司 | A method of ceramide is prepared from apple juicing pomace |
| CN114436884A (en) * | 2020-11-02 | 2022-05-06 | 南京农业大学 | Burdock ceramide compound and preparation method and application thereof |
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| CN114436884A (en) * | 2020-11-02 | 2022-05-06 | 南京农业大学 | Burdock ceramide compound and preparation method and application thereof |
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| CN108017554B (en) | 2020-10-02 |
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