CN105037451B - A kind of method of hyperfiltration treatment flavomycoin zymotic fluid - Google Patents
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid Download PDFInfo
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- CN105037451B CN105037451B CN201510433960.1A CN201510433960A CN105037451B CN 105037451 B CN105037451 B CN 105037451B CN 201510433960 A CN201510433960 A CN 201510433960A CN 105037451 B CN105037451 B CN 105037451B
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Abstract
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid disclosed by the invention, belongs to technical field of biochemical industry, comprises the following steps：1) by flavomycoin zymotic fluid deionized water continuous ultrafiltration 1h, dialyzate is discarded；2) by step 1) ultrafiltration retention flavomycoin zymotic fluid with containing micella conditioning agent the aqueous solution continue ultrafiltration 1h, collect enrichment flavomycoin dialyzate.The ultrafiltration that the present invention is used first passes through the small molecular weight impurity in deionized water removing zymotic fluid, continue ultrafiltration removing big molecular impurity by adding the micella conditioning agent aqueous solution again, xanthomycin A component further is refining to obtain by chromatography to the ultrafiltrate rich in flavomycoin.Compared with the prior art, technique is simple, and operating process is shortened dramatically, low, environmental protection of consuming energy, and is adapted to industrial-scale production.
Description
Technical field
The invention belongs to technical field of biochemical industry, it is related to a kind of method of hyperfiltration treatment flavomycoin zymotic fluid.
Background technology
Flavomycoin, also known as moenomycin (bambermycin) (moenomycin), are a kind of phosphoric acid sugar lipid antibiotic, are spot Bai Shi streptomycetes
Tunning, be the adopted name of some analogues.Flavomycoin acts on stronger, its pharmacological action to gram-positive bacteria
It is the biosynthesis for disturbing peptide glycan, causes bacterial cell to rupture and cause bacterium self-dissolving.For a long time, flavomycoin is mainly made
Used for antibioticses growth improver for livestock and poultry in countries in the world.Chinese patent CN1194984A discloses the new use of flavomycoin
On the way, flavomycoin and its bismuth salt composition can control the infection of helicobacter pylori, treat the various stomach trouble such as gastric ulcer.In order to reduce
Side effects of pharmaceutical drugs, its Pharmaceutical ingredients of human medicine are generally single compound, therefore isolating and purifying for xanthomycin A component is ground
Study carefully value to highlight.
BP GB1068639 and Chinese patent ZL 200510051382.1 by solvent extraction, dialysis, precipitation,
Different groups of the isolation and purification methods such as the decolouring of magnesium silicate column chromatography, gel filtration chromatography, anion-exchange chromatography, reverse-phase chromatography
Close, eliminate other impurity, obtained the mixture of flavomycoin each component.
Relevant single xanthomycin A component to isolate and purify document as described below：
On the basis of United States Patent (USP) US 3660569 is handled before to feed liquid, xanthomycin A is obtained by silica gel normal-phase chromatography
Component.
Sun Cheng boats et al. (phosphoric acid sugar lipid antibiotic moenomycin A separation and identification, Chinese antibiotic magazine,
2003,28(6):325-327,360) first with normal-phase chromatography pre-separation flavomycoin disclosed in United States Patent (USP) US 3660569, then lead to
Analysis level reverse-phase chromatographic column is crossed, xanthomycin A component sterling has been obtained.
Chinese patent ZL 201210029457.6 discloses a kind of method for preparing xanthomycin A component.Pass through C18 solid phases
Extraction → C18 analysis post separation → C18 SPEs are further refined, in order to ensure purity, agents useful for same be chromatographically pure and
Ultra-pure water, finally obtains flaxen Mon A.
The preparation technology of xanthomycin A component its core process disclosed in United States Patent (USP) US 5986089 be macroporous absorption or
→ anion-exchange chromatography → reverse-phase chromatography is combined in ultrafiltration with solvent extraction.
In summary, due to the similarity of structure between flavomycoin each component, in order to obtain single xanthomycin A component,
The chromatographic isolation of above-mentioned patent in different modalities is core.In order to reach the purpose of chromatographic isolation, and also to protect high
Expensive chromatograph packing material, there is multistep pretreating process before chromatographic isolation, and technique redundant and complicated, cost is high.
A series of patents isolated and purified on flavomycoin, such as BP GB have been declared by German Hoechst companies
1068639th, United States Patent (USP) US 3660569, US 3674866 etc. refer to that flavomycoin has the characteristic that can not be dialysed, that is,
Say flavomycoin as a kind of molecular weight 68000-70000 macromolecular compound, it is impossible to through conventional fenestra.And with this characteristic
Based on separation, purifying flavomycoin.There is special advantage as the proposition dialysis of BP GB 1068639 separates flavomycoin, and
The flavomycoin after solvent extraction is continuously dialysed 3 days in embodiment.As the modern industry application of dialysis principle, the U.S. is special
Sharp US 5986089 has also explained in detail the process that ultrafiltration isolates and purifies flavomycoin in embodiment, but is come with the data in embodiment
Analysis, the actual effect of ultrafiltration is inferior to macroporous absorption method.
Later research shows that the molecular weight of flavomycoin each component is far smaller than the understanding of early stage, and real molecular weight is less than
1600.Why flavomycoin can not dialyse and early stage is the unique chemistry knot of flavomycoin to the wrong understanding of its molecular weight
Structure.Flavomycoin is amphoteric compound, and its one end is the extremely strong C25 aliphatic chains of hydrophobicity, and it is extremely strong that the other end contains 5 hydrophilies
Monose, and 3 ionizable acidic sites, therefore its physicochemical properties is similar with ionic surfactant.Water-soluble
Flavomycoin molecule is mutually assembled in liquid, exists in the form of micella, thus shows the feature of macromolecular, such as is difficult to dialyse.
Also this characteristic is based on, BP GB 1068639, United States Patent (USP) US 5986089 separate Huang by way of UF membrane
Mycin, i.e. small molecular weight impurity pass through fenestra, and flavomycoin is trapped in the opposite side of film in the form of macromolecular micella.
The content of the invention
In order to overcome the defect of above-mentioned prior art, it is an object of the invention to provide a kind of fermentation of hyperfiltration treatment flavomycoin
The method of liquid, this method operating process is simple, energy-conserving and environment-protective,
The present invention is to be achieved through the following technical solutions：
The invention discloses a kind of method of hyperfiltration treatment flavomycoin zymotic fluid, comprise the following steps：
1) by flavomycoin zymotic fluid deionized water continuous ultrafiltration 1h, dialyzate is discarded；
2) by step 1) ultrafiltration retention flavomycoin zymotic fluid with containing micella conditioning agent the aqueous solution continue ultrafiltration 1h, receive
The dialyzate of collection enrichment flavomycoin.
Step 2) described in micella conditioning agent be methanol, ethanol, isopropanol, ethylene glycol, formamide or urea.
The material of milipore filter used in ultrafiltration is polyether sulfone, polysulfones, polyacrylonitrile or polyamide.
The molecular cut off of milipore filter used in ultrafiltration is 3000~50000.
In step 1) it is preceding also including being pre-processed to flavomycoin zymotic fluid, concrete operations are：By flavomycoin zymotic fluid in 4
DEG C refrigerated overnight, then centrifuges 10min under conditions of 8000r/min.
In step 2) after also include using the step that is refined of chromatography to the dialyzate for being enriched with flavomycoin.
It is refined to use normal phase chromatography, RP chromatography or ion-exchange chromatography.
The filler of normal-phase chromatography is silica gel, and its particle diameter is 20~150 μm；The skeleton of ion-exchange chromatography filler is poly- methyl
Esters of acrylic acid, its functional group is-CH2-CH2-NH-(C2H5)2, particle diameter is 20~75 μm.
RP chromatography concrete operations are：
The pH value that the dialyzate of flavomycoin will be enriched with is adjusted to 3.0~4.5, and filling is pumped into 50~250cm/hr flow velocity
There is the chromatographic column of reverse-phase chromatography filler, with identical flow velocity, it is A mobile phases to choose 20% methanol solution that pH value is 8.30, with
Pure methanol is B mobile phases, according to 0~40%B mobile phase linear gradient elution 40min, then with 40%B mobile phase Gradient elutions
Desorbed completely to xanthomycin A component, merge high-purity xanthomycin A component, removed and be freeze-dried after solvent, the Huang after being refined
Mycin component A product.
Reverse-phase chromatography filler aperture used isParticle diameter is 20~75 μm；Reverse-phase chromatography filler is silicon
C8, C18 filler that glue is modified, or be the chromatograph packing material of polymer substrate；
Polymer substrate is styrene-divinylbenzene polymer or polymethacrylate polymer.
Compared with prior art, the present invention has following beneficial technique effect：
The method of a kind of hyperfiltration treatment flavomycoin zymotic fluid disclosed by the invention, first by flavomycoin zymotic fluid deionization
Water continuous ultrafiltration, removes the small molecular weight impurity in zymotic fluid, and flavomycoin is trapped in the opposite side of film；Being contained again by addition can
The conditioning agent aqueous solution for adjusting micellar size continues ultrafiltration, and flavomycoin micella is destroyed or micella diminishes so as to pass through film and some
Big molecular impurity envelope is retained, so as to obtain the ultrafiltrate for the enrichment flavomycoin that hyperfiltration treatment is crossed.The ultrafiltration that the present invention is used
Compared with the prior art, technique is simple, and operating process is shortened dramatically for method, and low, environmental protection of consuming energy is adapted to industrially scalable life
Production.
Further, the present invention is refined to the ultrafiltrate for being enriched with flavomycoin using chromatogram is prepared, and obtains xanthomycin A group
Point.
Embodiment
With reference to specific embodiment, the present invention is described in further detail, it is described be explanation of the invention and
It is not to limit.
The technical solution used in the present invention is as follows：
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid, comprises the following steps：
(1) ultrafiltration pre-separation flavomycoin
Flavomycoin ferment filtrate is put in into cold compartment of refrigerator to stay overnight, 10min is centrifuged under the conditions of 8000r/min, precipitation is removed
Thing, obtains flavomycoin centrifuged supernatant；
Ultrafiltration is divided into two steps, and first, flavomycoin centrifuged supernatant deionized water continuous ultrafiltration 1h is removed in filtered fluid
Small molecular weight impurity, flavomycoin is trapped in the opposite side of film；Second, add the aqueous solution containing micellar size conditioning agent and continue super
Filter, flavomycoin micella is destroyed or micella diminishes so as to which through film, some big molecular impurity envelopes are retained.
Described micella conditioning agent includes C1-C3 lower alcohol such as methanol, ethanol and isopropanol, ethylene glycol, amide-type such as
Formamide, urea；
The material of milipore filter used in ultrafiltration is polyether sulfone, polysulfones, polyacrylonitrile, polyamide；
The molecular cut off of milipore filter used in ultrafiltration is 3000-50000；
(2) chromatography is refined
Normal-phase chromatography, reverse-phase chromatography and ion-exchange chromatography can be used.
It is RP chromatography below：
Take and flavomycoin solution is rich in obtained by 160~400mL ultrafiltrations, adjust pH=3.0~4.5, flowed with 50-250cm/hr
Speed is pumped into the chromatographic column (20 × 250mm) for being filled with reverse-phase chromatography filler.Then with same flow velocity, with pH=8.30 20% first
Alcohol is as A mobile phases, and 100% methanol is B mobile phases, and 40min is eluted according to 0-40%B linear gradient modes, then with 40%B etc.
Gradient elution to Mon component As are desorbed completely, merge high-purity Mon A cuts.Solvent is removed through ultrafiltration or revolving, freezing is dry
It is dry to obtain product.
20-75 μm of described reverse-phase chromatography its packing material size, reverse-phase chromatography condiment includes C8 the or C18 fillers that silica gel is modified
And the reverse phase filler of polymer substrate, described polymer substrate includes styrene-divinylbenzene polymer or poly- methyl-prop
Olefin(e) acid esters polymer；
20-150 μm of described normal-phase chromatography its packing material size；
20-75 μm of described ion-exchange chromatography its packing material size, is polymethacrylate skeleton, functional group
For-CH2-CH2-NH-(C2H5)2。
1st, retention of the xanthomycin A under different additive
Flavomycoin zymotic fluid (solid content is 30g/L) is put in into cold compartment of refrigerator (4 DEG C) to stay overnight, under the conditions of 8000r/min
10min is centrifuged, sediment is removed, supernatant is standby.
30mL centrifuged supernatants are respectively taken, methanol, ethanol, isopropanol 5mL, ethylene glycol 1mL, formamide 1mL, urine are added respectively
Plain 1g.Above-mentioned supernatant is super with Minimate Tangential Flow Filtration System (Pall companies of the U.S.)
Filter, milipore filter is molecular cut off 10K poly (ether-sulfone) ultrafiltration membrane, and operating pressure 25psi carries out HPLC detections, knot to concentrate
Fruit is shown in Table 1.
Retention of the xanthomycin A of table 1 under different additive
It can be seen that, after addition methanol, ethanol, isopropanol, ethylene glycol, formamide, urea liquid, there is part xanthomycin A component
Fenestra is can pass through, causes the rejection of its film to decline.Reason be these materials improve flavomycoin critical micelle concentration (CMC,
Critical micelle concentration), make the flavomycoin in centrifuged supernatant be difficult to form micella in aqueous
Or the concentration class of micella declines, so as to improve the ratio that flavomycoin passes through fenestra.
2nd, retention of the xanthomycin A under different formamide additions
1mL, 10mL, 20mL, 30mL, 40mL, 50mL formamide are added in centrifuged supernatant, other conditions such as embodiment 1,
As a result it is as shown in table 2：
Retention of the xanthomycin A of table 2 under different formamide additions
It can be seen that, with the consumption increase of formamide, milipore filter declines to the interception of xanthomycin A component.
Embodiment 1
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid, comprises the following steps：
1) flavomycoin zymotic fluid (solid content is 30g/L) is put in into cold compartment of refrigerator (4 DEG C) to stay overnight, 8000r/min conditions
Lower centrifugation 10min, removes sediment, and supernatant is standby；
2) 400mL supernatant deionized water continuous ultrafiltration 1h are taken, pressure is 25psi；
3) mass fraction for being 9.0 with pH value by ultrafiltrate is that 1% aqueous solution of urea continues ultrafiltration 1.0h, collects 1200mL
Ultrafiltrate；
Polysulphone super-filter membrane is selected in ultrafiltration, and ultrafiltration membrane molecule interception is 10000；
Detect yield and purity.The purity of xanthomycin A component is 51.5%, and yield is 57.4%.
4) dialyzate of the enrichment flavomycoin after 400mL ultrafiltration is taken, pH=3.0 is adjusted, filling is pumped into 50cm/hr flow velocitys
There is the chromatographic column (20 × 250mm) of reverse-phase chromatography filler.Then with same flow velocity, washed with pH=8.30 20% methanol as A
De- liquid, 100% methanol is B eluents, and 40min is eluted according to 0-40%B linear gradient modes, then with 40%B constant gradient modes
It is eluted to Mon component As to desorb completely, merges high-purity Mon A cuts.Solvent is removed through ultrafiltration or revolving, freeze-drying is produced
Product；
Wherein, reverse-phase chromatography filler aperture used isParticle diameter is 50 μm, and reverse-phase chromatography filler is modified for silica gel
C8, it is refined after xanthomycin A compositional purity reach 94%.
Embodiment 2
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid, comprises the following steps：
1) flavomycoin zymotic fluid (solid content is 30g/L) is put in into cold compartment of refrigerator (4 DEG C) to stay overnight, 8000r/min conditions
Lower centrifugation 10min, removes sediment, and supernatant is standby；
2) 400mL supernatant deionized water continuous ultrafiltration 1h are taken, pressure is 25psi, collects filtered fluid；
3) methanol aqueous solution that the volume fraction for being 7.5 with pH value by filtered fluid is 2% continues ultrafiltration 1.0h, collects
1200mL ultrafiltrates；
Polyacrylonitrile ultrafiltration film is selected in ultrafiltration, and ultrafiltration membrane molecule interception is 30000；
Detect yield and purity.The purity of xanthomycin A component is 48.3%, and yield is 59.7%.
4) dialyzate of the enrichment flavomycoin after 400mL ultrafiltration is taken, pH=3.5 is adjusted, dress is pumped into 100cm/hr flow velocitys
It is filled with the chromatographic column (20 × 250mm) of reverse-phase chromatography filler.Then with same flow velocity, A is used as with pH=8.30 20% methanol
Eluent, 100% methanol is B eluents, and 40min is eluted according to 0-40%B linear gradient modes, then with 40%B constant gradient sides
Formula is eluted to Mon component As and desorbed completely, merges high-purity Mon A cuts.Solvent is removed through ultrafiltration or revolving, freeze-drying is obtained
Product.
Wherein, reverse-phase chromatography filler aperture usedParticle diameter is 35 μm, and reverse-phase chromatography filler is styrene-diethyl
The polymer filler of alkene phenyl matter, the xanthomycin A compositional purity after refining reaches 95%.
Embodiment 3
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid, comprises the following steps：
1) flavomycoin zymotic fluid (solid content is 30g/L) is put in into cold compartment of refrigerator (4 DEG C) to stay overnight, 8000r/min conditions
Lower centrifugation 10min, removes sediment, and supernatant is standby；
2) 400mL supernatant deionized water continuous ultrafiltration 1h are taken, pressure is 25psi, collects filtered fluid；
3) volume fraction for being 7.0 with pH value by filtered fluid is that 1.5% glycol water continues ultrafiltration 1.0h, is collected
1200mL ultrafiltrates；
Polyamide milipore filter is selected in ultrafiltration, and ultrafiltration membrane molecule interception is 50000；
Detect yield and purity.The purity of xanthomycin A component is 46.3%, and yield is 60.4%.
4) dialyzate of the enrichment flavomycoin after 400mL ultrafiltration is taken, pH=4.0 is adjusted, dress is pumped into 150cm/hr flow velocitys
It is filled with the chromatographic column (20 × 250mm) of reverse-phase chromatography filler.Then with same flow velocity, A is used as with pH=8.30 20% methanol
Eluent, 100% methanol is B eluents, and 40min is eluted according to 0-40%B linear gradient modes, then with 40%B constant gradient sides
Formula is eluted to Mon component As and desorbed completely, merges high-purity Mon A cuts.Solvent is removed through ultrafiltration or revolving, freeze-drying is obtained
Product.
Wherein, reverse-phase chromatography filler aperture usedParticle diameter is 75 μm, and reverse-phase chromatography filler is polymethyl
The polymer filler of esters of gallic acid matrix, the xanthomycin A compositional purity after refining reaches 93%.
Embodiment 4
A kind of method of hyperfiltration treatment flavomycoin zymotic fluid, comprises the following steps：
1) flavomycoin zymotic fluid (solid content is 30g/L) is put in into cold compartment of refrigerator (4 DEG C) to stay overnight, 8000r/min conditions
Lower centrifugation 10min, removes sediment, and supernatant is standby；
2) 400mL supernatant deionized water continuous ultrafiltration 1h are taken, pressure is 25psi, collects filtered fluid；
3) mass fraction for being 6.0 with pH value by filtered fluid is that 1% formyl amine aqueous solution continues ultrafiltration 1.0h, is collected
1200mL ultrafiltrates；
From poly (ether-sulfone) ultrafiltration membrane, ultrafiltration membrane molecule interception is 3000；
Detect yield and purity.The purity of xanthomycin A component is 52.8%, and yield is 54.6%.
4) dialyzate of the enrichment flavomycoin after 400mL ultrafiltration is taken, pH=4.5 is adjusted, dress is pumped into 250cm/hr flow velocitys
It is filled with the chromatographic column (20 × 250mm) of reverse-phase chromatography filler.Then with same flow velocity, A is used as with pH=8.30 20% methanol
Eluent, 100% methanol is B eluents, and 40min is eluted according to 0-40%B linear gradient modes, then with 40%B constant gradient sides
Formula is eluted to Mon component As and desorbed completely, merges high-purity Mon A cuts.Solvent is removed through ultrafiltration or revolving, freeze-drying is obtained
Product.
Wherein, reverse-phase chromatography filler aperture usedParticle diameter is 20-45 μm, and reverse-phase chromatography filler is modified for silica gel
C18, it is refined after xanthomycin A compositional purity reach 97%.
In summary, it is found through experiments that, the micellar size of flavomycoin, namely the extent of polymerization of flavomycoin in aqueous
It can be adjusted by additive, this allows for ultrafiltration pre-separation flavomycoin and is possibly realized, so that the preparation of xanthomycin A component
Technique is greatly simplified.
Claims (8)
1. a kind of method of hyperfiltration treatment flavomycoin zymotic fluid, it is characterised in that comprise the following steps：
1) by flavomycoin zymotic fluid deionized water continuous ultrafiltration 1h, dialyzate is discarded；
2) by step 1) the flavomycoin zymotic fluid of ultrafiltration retention continues ultrafiltration 1h with the aqueous solution containing micella conditioning agent, collects rich
Collect the dialyzate of flavomycoin；
Described micella conditioning agent is formamide or urea；
The material of milipore filter used in ultrafiltration is polyether sulfone, polysulfones, polyacrylonitrile or polyamide.
2. the method for a kind of hyperfiltration treatment flavomycoin zymotic fluid according to claim 1, it is characterised in that surpass used in ultrafiltration
The molecular cut off of filter membrane is 3000~50000.
3. the method for a kind of hyperfiltration treatment flavomycoin zymotic fluid according to claim 1, it is characterised in that in step 1) before
Also include pre-processing flavomycoin zymotic fluid, concrete operations are：By flavomycoin zymotic fluid in 4 DEG C of refrigerated overnights, Ran Hou
10min is centrifuged under conditions of 8000r/min.
4. the method for a kind of hyperfiltration treatment flavomycoin zymotic fluid according to claim 1, it is characterised in that in step 2) after
Also include the step for using chromatography to be refined the dialyzate for being enriched with flavomycoin.
5. the method for a kind of hyperfiltration treatment flavomycoin zymotic fluid according to claim 4, it is characterised in that refined using just
Phase chromatography, RP chromatography or ion-exchange chromatography.
6. the method for a kind of hyperfiltration treatment flavomycoin zymotic fluid according to claim 5, it is characterised in that normal-phase chromatography
Filler is silica gel, and its particle diameter is 20~150 μm；
The skeleton of ion-exchange chromatography filler is polymethacrylate, and its functional group is-CH2-CH2-NH-(C2H5)2, grain
Footpath is 20~75 μm.
7. a kind of method of hyperfiltration treatment flavomycoin zymotic fluid according to claim 5, it is characterised in that RP chromatography
Concrete operations are：
The pH value for the dialyzate that flavomycoin will be enriched with is adjusted to 3.0~4.5, is pumped into and is filled with instead with 50~250cm/hr flow velocity
The chromatographic column of phase chromatography stuffing, with identical flow velocity, it is A mobile phases to choose 20% methanol solution that pH value is 8.30, with pure first
Alcohol is B mobile phases, according to 0~40%B mobile phase linear gradient elution 40min, then with 40%B mobile phases Gradient elution to Huang
Mycin component A is desorbed completely, merges high-purity xanthomycin A component, is removed and is freeze-dried after solvent, the flavomycoin after being refined
Component A product.
8. the method for a kind of hyperfiltration treatment flavomycoin zymotic fluid according to claim 7, it is characterised in that used is anti-phase
Chromatograph packing material aperture isParticle diameter is 20~75 μm；Reverse-phase chromatography filler is C8, C18 filler that silica gel is modified,
Or be the chromatograph packing material of polymer substrate；
Polymer substrate is styrene-divinylbenzene polymer or polymethacrylate polymer.
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| GB1068639A (en) * | 1964-09-21 | 1967-05-10 | Hoechst Ag | A purified form of the antibiotic moenomycin and a process for its manufacture |
| EP0872556A3 (en) * | 1997-04-17 | 2000-06-14 | Hoechst Aktiengesellschaft | Process for the preparation of moenomycin A |
| CN1290853C (en) * | 2005-03-09 | 2006-12-20 | 中牧实业股份有限公司 | Purifying method for moenomycin |
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