CN104193665A - Separating and purifying method for prodigiosin - Google Patents
Separating and purifying method for prodigiosin Download PDFInfo
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- CN104193665A CN104193665A CN201410387848.4A CN201410387848A CN104193665A CN 104193665 A CN104193665 A CN 104193665A CN 201410387848 A CN201410387848 A CN 201410387848A CN 104193665 A CN104193665 A CN 104193665A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
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Abstract
The invention belongs to the technical field of biochemistry, relates to a method for directly separating and purifying prodigiosin from fermentation liquor, and discloses a separating and purifying method for prodigiosin. The separating and purifying method comprises the following steps: after centrifuging fermentation liquor, carrying out ultrasonic extraction, concentration, ethyl acetate dissolving, silica gel chromatography and concentrating-drying in sequence to obtain refined prodigiosin. The separating and purifying method adopts an ultrasonic wall-breaking technology, has the advantages that the operation is simple and convenient, the efficiency is high, the cost is low and the active ingredients are not broken. The purity of the prodigiosin prepared by the preparation method is not less than 98.5%, and thus, the separating and purifying method is suitable for large-scale production requirements.
Description
Technical field
The invention belongs to technological field of biochemistry, relate to a kind of directly method of separation and purification prodigiosin from fermented liquid.
Background technology
Prodigiosin (prodigiosins, PG) is the natural red colouring matter that a class has multiple pyrrole ring structures, and molecular formula is C
20h
25n
3o (M=323.1968), its structural formula is shown in accompanying drawing 1.
Prodigiosin nineteen twenty-nine found by the research such as Amak, by Harashiniak etc. separate first and Purification out.The early stage research of prodigiosin mainly concentrates on this pigment and has antibacterial, antimycotic, anti-disease disease and other biological activity, the most popular the showing on its immunosuppressive activity and antitumor booster action of research now, this natural cancer therapy drug, oneself more and more receives the vast concern of research circle and needs to be become the candidate drug of anticarcinogen.Also comprised its using value at food and industrial circle about the research of prodigiosin in recent years.
Early stage as far back as 20th century, just there is scientist to describe the whole process of prodigiosin chemosynthesis, but more complicated and difficulty.Have subsequently recent studies on to propose the new scheme of preparing prodigiosin analogue and obtain prodigiosin precursor substance, step is simple, and combined coefficient obviously improves, but cannot obtain natural dodecyl prodigiosin.Utilize chemical synthesis to prepare in a large number prodigiosin and fail to implement always, sight has been turned to microorganism fermentative production by researchist.Prodigiosin can be produced by various bacteria and actinomycetes, comprise streptomyces (Streptomyces), serratia (Serratia) and Rhodopseudomonas (Pseudomonas), wherein about the most study of serratia (Serratia).
Prodigiosin is the integral part of cell walls, in the process of Serratia fermentative production prodigiosin, the prodigiosin major part producing is attached on the interior adventitia of bacterium, only having small part to be unbound state is present in fermented liquid, by adding tensio-active agent prodigiosin can be discharged in solution, thereby increase the ratio of free state prodigiosin, and the integrity of cytolemma is essential for the biosynthesizing of prodigiosin.Based on this, the separation and purification process of prodigiosin is mainly taked centrifuging and taking thalline after fermentation ends, then by the method for acidic methanol extraction, extraction liquid again through silicagel column and oppositely column separating purification obtain prodigiosin sterling.This technology is the main method of current prodigiosin separation and purification, and this technique organic solvent consumption is large, and product yield is low, is difficult to meet the needs of batch production.
In order to overcome above technical barrier, the invention provides a kind of separation purification method of prodigiosin.
Summary of the invention
The object of the invention is to solve prior art defect, a kind of separation purification method of prodigiosin is provided, for large-scale production provides foundation.Compared with prior art, extract yield of the present invention is high, chemical reagent consumption is few, the used time is short and product purity is high.
Technical scheme of the present invention is: a kind of separation purification method of prodigiosin, comprises the following steps:
Step 1, to get prodigiosin fermented liquid centrifugal, collects thalline, dissolves;
Step 2, the solution in step 1 is carried out to ultrasonic extraction, extraction time is 20～30min, and temperature is 25～28 DEG C, and frequency is 30～45kHz, centrifugal, vacuum concentration;
Step 3, gained enriched material is added to acetic acid ethyl dissolution, sealing vibration, centrifugal, collect supernatant liquor;
Step 4, described supernatant liquor is carried out to silica gel column chromatography, collect elution fraction;
Step 5, described elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin.
Preferably, in the separation purification method of described prodigiosin, in described step 4, the moving phase that silica gel column chromatography carries out gradient elution is the mixing solutions of sherwood oil and ethyl acetate, the condition of gradient elution is that initial period sherwood oil and ethyl acetate volume ratio are 60: 1, intermediate stage sherwood oil and ethyl acetate volume ratio are 50: 1 and 20: 1, and terminal stage sherwood oil and ethyl acetate volume ratio are 4: 1, collect the component that terminal stage elutes.
Preferably, in the separation purification method of described prodigiosin, in described step 4, the carrier of described silica gel column chromatography is 200 order silica gel column chromatographies.
Preferably, in the separation purification method of described prodigiosin, in described step 1, prodigiosin fermented liquid is under 10000rpm, to carry out centrifugally at rotating speed, and centrifugation time is 10～15min.
Preferably, in the separation purification method of described prodigiosin, in described step 1, collect after thalline, add thalline described in acetone solution, the volume ratio of described thalline and acetone is 1: 3～1: 2.
Preferably, in the separation purification method of described prodigiosin, in described step 2, ultrasonic extraction liquid is centrifugal 10～15min under 10000rpm at rotating speed.
Preferably, in the separation purification method of described prodigiosin, in described step 3, the volume ratio of ethyl acetate and enriched material is 10: 1～15: 1, after sealing, is at 30 DEG C in temperature, and rotating speed is 200rpm vibration 2～3 days.
Preferably, in the separation purification method of described prodigiosin, in described step 3, be under 10000rpm, to carry out centrifugally by the solution after vibration at rotating speed, centrifugation time is 10min.
Preferably, in the separation purification method of described prodigiosin, in described step 5, the refining prodigiosin purity obtaining is not less than 98.5%.
The invention has the advantages that:
1, based on ultrasonic cavitation effect, be 20～30min in extraction time, temperature is 25～28 DEG C, frequency is under 30～45kHz condition, promotes fermented liquid cell wall breaking, and more prodigiosin is entered in feed liquid;
2, utilize the gradient elution separation method of silica gel column chromatography, the prodigiosin purity of collecting is reached more than 98.5%, and can process in a large number prodigiosin;
3, process operation is easy, efficiency is high, do not destroy effective constituent;
4, organic solvent is recyclable, has saved the consumption of organic solvent.
Brief description of the drawings
Fig. 1 is prodigiosin structural formula;
Fig. 2 is the process flow sheet of refining prodigiosin.
Embodiment
Below in conjunction with accompanying drawing, the present invention is described in further detail, to make those skilled in the art can implement according to this with reference to specification sheets word.
As shown in Figure 2, the separation purification method of prodigiosin of the present invention, comprises the following steps:
Step 1, to get prodigiosin fermented liquid centrifugal, collects thalline, dissolves;
Step 2, the solution in step 1 is carried out to ultrasonic extraction, extraction time is 20～30min, and temperature is 25～28 DEG C, and frequency is 30～45kHz, centrifugal, vacuum concentration;
Step 3, gained enriched material is added to acetic acid ethyl dissolution, sealing vibration, centrifugal, collect supernatant liquor;
Step 4, described supernatant liquor is carried out to silica gel column chromatography, collect elution fraction;
Step 5, described elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin.。
In the separation purification method of described prodigiosin, in described step 4, the moving phase that silica gel column chromatography carries out gradient elution is the mixing solutions of sherwood oil and ethyl acetate, the condition of gradient elution is that initial period sherwood oil and ethyl acetate volume ratio are 60: 1, intermediate stage sherwood oil and ethyl acetate volume ratio are 50: 1 and 20: 1, terminal stage sherwood oil and ethyl acetate volume ratio are 4: 1, collect the component that terminal stage elutes.
In the separation purification method of described prodigiosin, in described step 4, the carrier of described silica gel column chromatography is 200 order silica gel column chromatographies.
In the separation purification method of described prodigiosin, in described step 1, prodigiosin fermented liquid is under 10000rpm, to carry out centrifugally at rotating speed, and centrifugation time is 10～15min.
In the separation purification method of described prodigiosin, in described step 1, collect after thalline, add thalline described in acetone solution, the volume ratio of described thalline and acetone is 1: 3～1: 2.
In the separation purification method of described prodigiosin, in described step 2, ultrasonic extraction liquid is centrifugal 10～15min under 10000rpm at rotating speed.
In the separation purification method of described prodigiosin, in described step 3, the volume ratio of ethyl acetate and enriched material is 10: 1～15: 1, after sealing, is at 30 DEG C in temperature, and rotating speed is 200rpm vibration 2～3 days.
In the separation purification method of described prodigiosin, in described step 3, be under 10000rpm, to carry out centrifugally by the solution after vibration at rotating speed, centrifugation time is 10min.
In the separation purification method of described prodigiosin, in described step 5, the refining prodigiosin purity obtaining is not less than 98.5%.
Above-mentioned all organic solvents used can reclaim by vacuum concentration, recycle.
The present invention has been two groups of simultaneous test A and B simultaneously.
Simultaneous test A
1, get 30L fermented liquid, centrifugal 10min under 10000rpm, collects thalline, adds 60L acetone fully mixed, dissolves.
2, the mixing solutions rotary evaporation in vacuo containing prodigiosin is concentrated.
3, above-mentioned enriched material is added to 15 times of volumes of acetic acid ethyl esters and dissolve, sealing, at 30 DEG C, 200rpm vibration 2 days, centrifugal 10min under 10000rpm, collects supernatant liquor.
4, by 200 order silica gel column chromatographies on gained supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 60: 1,50: 1 intermediate stages and 20: 1, final proportioning is 4: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 4: 1 o'clock.
5, again elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin 340.0g, purity 95.12%.
Simultaneous test B
1, get 30L fermented liquid, centrifugal 10min under 10000rpm, collects thalline, adds 60L acetone fully mixed, dissolves.
2, above-mentioned solution is carried out to ultrasonication, extraction time is 25min, and ultrasonic temperature is 25 DEG C, and ultrasonic frequency is 30kHz, centrifugal 10min under 10000rpm, and rotary evaporation in vacuo is concentrated.
3, above-mentioned enriched material is added to 15 times of volumes of acetic acid ethyl esters and dissolve, sealing, at 30 DEG C, 200rpm vibration 2 days, centrifugal 10min under 10000rpm, collects supernatant liquor.
4, by 200 order silica gel column chromatographies on gained supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 50: 1,20: 1 intermediate stages and 10: 1, final proportioning is 5: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 5: 1 o'clock.
5, again elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin 343.4g, purity 96.09%.
Embodiment 1
1, get 30L fermented liquid, centrifugal 10min under 10000rpm, collects thalline, adds 60L acetone fully mixed, dissolves.
2, above-mentioned solution is carried out to ultrasonication, extraction time is 25min, and ultrasonic temperature is 25 DEG C, and ultrasonic frequency is 30kHz, centrifugal 10min under 10000rpm, and rotary evaporation in vacuo is concentrated.
3, above-mentioned enriched material is added to 15 times of volumes of acetic acid ethyl esters and dissolve, sealing, at 30 DEG C, 200rpm vibration 2 days, centrifugal 10min under 10000rpm, collects supernatant liquor.
4, by 200 order silica gel column chromatographies on gained supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 60: 1,50: 1 intermediate stages and 20: 1, final proportioning is 4: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 4: 1 o'clock.
5, again elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin 352.5g, purity 98.63%.
Embodiment 2
1, get 30L fermented liquid, centrifugal 10min under 10000rpm, collects thalline, adds 60L acetone fully mixed, dissolves.
2, above-mentioned solution is carried out to ultrasonication, extraction time is 25min, and ultrasonic temperature is 25 DEG C, and ultrasonic frequency is 35kHz, centrifugal 10min under 10000rpm, and rotary evaporation in vacuo is concentrated.
3, enriched material is added to 12 times of volumes of acetic acid ethyl esters and dissolves, sealing, at 30 DEG C of temperature, 200rpm vibration 2 days, then under 10000rpm centrifugal 10min, collect supernatant liquor.
4, by 200 order silica gel column chromatographies on gained supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 60: 1,50: 1 intermediate stages and 20: 1, final proportioning is 4: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 4: 1 o'clock.
5, again elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin 359.8g, purity 98.59%.
Embodiment 3
1, get the centrifugal 15min of 30L fermented liquid 10000rpm, collect thalline, add 90L acetone fully mixed, dissolve.
2, above-mentioned solution is carried out to ultrasonication, extraction time is 30min, and ultrasonic temperature is 26 DEG C, and ultrasonic frequency is 40kHz, centrifugal 15min under 10000rpm, and rotary evaporation in vacuo is concentrated.
3, enriched material is added to 10 times of volumes of acetic acid ethyl esters and dissolve, sealing, at 30 DEG C of temperature, 200rpm vibration 3 days, then centrifugal 10min under 10000rpm, collects supernatant liquor.
4, by 200 order silica gel column chromatographies on gained supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 60: 1,50: 1 intermediate stages and 20: 1, final proportioning is 4: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 4: 1 o'clock.
5, elution fraction removes ethyl acetate equal solvent through normal pressure evaporation concentration, and concentrated solution is dried, and obtains refining prodigiosin 370.6g, purity 98.72%.
Embodiment 4
1, get the centrifugal 15min of 30L fermented liquid 10000rpm, collect thalline, add 60L acetone fully mixed, dissolve.
2, above-mentioned solution is carried out to ultrasonication, extraction time is 30min, and ultrasonic temperature is 28 DEG C, and ultrasonic frequency is 30kHz, the centrifugal 15min of 10000rpm, and rotary evaporation in vacuo is concentrated.
3, enriched material is added to 15 times of volumes of acetic acid ethyl esters and dissolve, sealing, at 30 DEG C of temperature, 200rpm vibration 3 days, centrifugal 10min under 10000rpm, collects supernatant liquor.
4, by 200 order silica gel column chromatographies on supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 60: 1,50: 1 intermediate stages and 20: 1, final proportioning is 4: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 4: 1 o'clock.
5, elution fraction removes ethyl acetate equal solvent through normal pressure evaporation concentration, and concentrated solution is dried, and obtains refining prodigiosin 368.2g, purity 98.75%.
Embodiment 5
1, get the centrifugal 15min of 30L fermented liquid 10000rpm, collect thalline, add 90L acetone fully mixed, dissolve.
2, above-mentioned solution is carried out to ultrasonication, extraction time is 30min, and ultrasonic temperature is 28 DEG C, and ultrasonic frequency is 45kHz, the centrifugal 15min of 10000rpm, and rotary evaporation in vacuo is concentrated.
3, enriched material adds 15 times of volumes of acetic acid ethyl esters dissolvings, sealing, and at 30 DEG C of temperature, 200rpm vibration 3 days, then centrifugal 10min under 10000rpm, collects supernatant liquor.
4, by 200 order silica gel column chromatographies on gained supernatant liquor, sherwood oil, ethyl acetate mixed solution carry out gradient elution, control sherwood oil: the initial proportioning of ethyl acetate is 60: 1,50: 1 intermediate stages and 20: 1, final proportioning is 4: 1, and the ratio of collecting sherwood oil and ethyl acetate is the component eluting for 4: 1 o'clock.
5, elution fraction removes ethyl acetate equal solvent through normal pressure evaporation concentration, and concentrated solution is dried, and obtains refining prodigiosin 373.4g, purity 98.66%.
The prodigiosin purity that the present invention obtains reaches more than 98.5%, and the product purity of simultaneous test A is 95.12%, and the product purity of simultaneous test B is 96.09%, is all less than 98.5%.Hence one can see that, and prodigiosin is carried out to ultrasonic extraction, then carries out silica gel column chromatography separating-purifying, and the purity of the prodigiosin obtaining is like this highest.
When ultrasonic extraction, some microbubbles have been dissolved in solvent inside, and these bubbles produce vibration under hyperacoustic effect, in the time that acoustic pressure reaches certain value, bubble is because orientation diffusion increases, form resonator, then closed suddenly, bubble can produce several thousand atmospheric pressure in the time of closure around it, form micro laser wave, it can cause fermented liquid cell wall rupture, and whole rupture process completes in moment, is conducive to the stripping of effective constituent.Ultrasonic wave is in the communication process of solvent, its acoustic energy is constantly absorbed by the particle of solvent, solvent by absorbed energy all or major part be transformed into heat energy, increase the dissolution rate of prodigiosin, the rising of the prodigiosin internal temperature causing due to this absorption acoustic energy is moment, and therefore the biological activity of prodigiosin remains unchanged.
Although embodiment of the present invention are open as above, but it is not restricted to listed utilization in specification sheets and embodiment, for those skilled in the art, can easily realize other amendment, therefore do not deviating under the universal that claim and equivalency range limit, the present invention is not limited to specific details and illustrates here and the example of describing.
Claims (9)
1. a separation purification method for prodigiosin, is characterized in that, comprises the following steps:
Step 1, to get prodigiosin fermented liquid centrifugal, collects thalline, dissolves;
Step 2, the solution in step 1 is carried out to ultrasonic extraction, extraction time is 20～30min, and temperature is 25～28 DEG C, and frequency is 30～45kHz, centrifugal, vacuum concentration;
Step 3, gained enriched material is added to acetic acid ethyl dissolution, sealing vibration, centrifugal, collect supernatant liquor;
Step 4, described supernatant liquor is carried out to silica gel column chromatography, collect elution fraction;
Step 5, described elution fraction is removed to ethyl acetate equal solvent through normal pressure evaporation concentration, concentrated solution is dried, obtain refining prodigiosin.
2. the separation purification method of prodigiosin as claimed in claim 1, it is characterized in that, in described step 4, the moving phase that silica gel column chromatography carries out gradient elution is the mixing solutions of sherwood oil and ethyl acetate, the condition of gradient elution is that initial period sherwood oil and ethyl acetate volume ratio are 60: 1, intermediate stage sherwood oil and ethyl acetate volume ratio are 50: 1 and 20: 1, and terminal stage sherwood oil and ethyl acetate volume ratio are 4: 1, collect the component that terminal stage elutes.
3. the separation purification method of prodigiosin as claimed in claim 2, is characterized in that, in described step 4, the carrier of described silica gel column chromatography is 200 order silica gel column chromatographies.
4. the separation purification method of prodigiosin as claimed in claim 1, is characterized in that, in described step 1, prodigiosin fermented liquid is under 10000rpm, to carry out centrifugally at rotating speed, and centrifugation time is 10～15min.
5. the separation purification method of prodigiosin as claimed in claim 4, is characterized in that, in described step 1, collects after thalline, adds thalline described in acetone solution, and the volume ratio of described thalline and acetone is 1: 3～1: 2.
6. the separation purification method of prodigiosin as claimed in claim 1, is characterized in that, in described step 2, ultrasonic extraction liquid is centrifugal 10～15min under 10000rpm at rotating speed.
7. the separation purification method of prodigiosin as claimed in claim 1, is characterized in that, in described step 3, the volume ratio of ethyl acetate and enriched material is 10: 1～15: 1, after sealing, is at 30 DEG C in temperature, and rotating speed is 200rpm vibration 2～3 days.
8. the separation purification method of prodigiosin as claimed in claim 7, is characterized in that, in described step 3, is under 10000rpm, to carry out centrifugally by the solution after vibration at rotating speed, and centrifugation time is 10min.
9. the separation purification method of prodigiosin as claimed in claim 1, is characterized in that, in described step 5, the refining prodigiosin purity obtaining is not less than 98.5%.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115745863A (en) * | 2022-11-14 | 2023-03-07 | 芝诺(苏州)生物科技有限公司 | Method for extracting prodigiosin from fermentation liquor containing prodigiosin |
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| CN1563400A (en) * | 2004-04-19 | 2005-01-12 | 华东理工大学 | Method for separating and preparing prodigiosin |
| CN1884483A (en) * | 2006-06-20 | 2006-12-27 | 中国科学院南海海洋研究所 | Marine bacteria strain for producing prodigiosin and the method for producing prodigiosin |
| CN102311981A (en) * | 2011-07-19 | 2012-01-11 | 东南大学 | Method for preparing and purifying prodigiosin |
| CN103755619A (en) * | 2014-01-09 | 2014-04-30 | 嘉兴学院 | Extraction and separation method of prodigiosin |
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- 2014-08-08 CN CN201410387848.4A patent/CN104193665B/en active Active
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| US4266028A (en) * | 1979-02-21 | 1981-05-05 | Kirin Beer Kabushiki Kaisha | Process for preparation of prodigiosin |
| CN1563400A (en) * | 2004-04-19 | 2005-01-12 | 华东理工大学 | Method for separating and preparing prodigiosin |
| CN1884483A (en) * | 2006-06-20 | 2006-12-27 | 中国科学院南海海洋研究所 | Marine bacteria strain for producing prodigiosin and the method for producing prodigiosin |
| CN102311981A (en) * | 2011-07-19 | 2012-01-11 | 东南大学 | Method for preparing and purifying prodigiosin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115745863A (en) * | 2022-11-14 | 2023-03-07 | 芝诺(苏州)生物科技有限公司 | Method for extracting prodigiosin from fermentation liquor containing prodigiosin |
| CN115745863B (en) * | 2022-11-14 | 2024-04-19 | 芝诺(苏州)生物科技有限公司 | Method for extracting prodigiosin from fermentation liquor containing prodigiosin |
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