CN106117280B - The isolation and purification method of rhodioside - Google Patents
The isolation and purification method of rhodioside Download PDFInfo
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- CN106117280B CN106117280B CN201610487411.7A CN201610487411A CN106117280B CN 106117280 B CN106117280 B CN 106117280B CN 201610487411 A CN201610487411 A CN 201610487411A CN 106117280 B CN106117280 B CN 106117280B
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- 238000000034 method Methods 0.000 title claims abstract description 18
- 238000000746 purification Methods 0.000 title claims abstract description 12
- 238000002955 isolation Methods 0.000 title claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000002904 solvent Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000019441 ethanol Nutrition 0.000 claims abstract description 11
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 10
- 241001165494 Rhodiola Species 0.000 claims abstract description 9
- 239000000287 crude extract Substances 0.000 claims abstract description 8
- 230000002411 adverse Effects 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 11
- 238000000605 extraction Methods 0.000 claims description 11
- 230000005526 G1 to G0 transition Effects 0.000 claims description 8
- 238000010262 high-speed countercurrent chromatography Methods 0.000 claims description 8
- 238000004088 simulation Methods 0.000 claims description 8
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 7
- 238000010828 elution Methods 0.000 claims description 5
- 238000001179 sorption measurement Methods 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003463 adsorbent Substances 0.000 claims description 4
- -1 and eluant Substances 0.000 claims description 4
- 239000003480 eluent Substances 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000000741 silica gel Substances 0.000 claims description 4
- 229910002027 silica gel Inorganic materials 0.000 claims description 4
- 238000013517 stratification Methods 0.000 claims description 4
- 230000006837 decompression Effects 0.000 claims 1
- YCCILVSKPBXVIP-UHFFFAOYSA-N 2-(4-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=C(O)C=C1 YCCILVSKPBXVIP-UHFFFAOYSA-N 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000000926 separation method Methods 0.000 description 3
- DBLDQZASZZMNSL-QMMMGPOBSA-N L-tyrosinol Natural products OC[C@@H](N)CC1=CC=C(O)C=C1 DBLDQZASZZMNSL-QMMMGPOBSA-N 0.000 description 2
- 240000005319 Sedum acre Species 0.000 description 2
- 235000014327 Sedum acre Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000004330 tyrosol Nutrition 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 description 1
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 description 1
- ILRCGYURZSFMEG-UHFFFAOYSA-N Salidroside Natural products OC1C(O)C(O)C(CO)OC1OCCC1=CC=C(O)C=C1 ILRCGYURZSFMEG-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 description 1
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 1
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- ILRCGYURZSFMEG-RQICVUQASA-N salidroside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1OCCC1=CC=C(O)C=C1 ILRCGYURZSFMEG-RQICVUQASA-N 0.000 description 1
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 description 1
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a kind of isolation and purification methods of rhodioside, include the following steps：（1）After rhodiola root drying and crushing, continuous countercurrent extracting tank is added, is extracted with water as solvent, filters, rhodioside crude extract is concentrated under reduced pressure to obtain；（2）It after the crude extract that step (1) obtains is dissolved with ethyl alcohol, is detached by Simulated Moving Bed Chromatography, is enriched with the component containing rhodioside；（3）Purified with high speed adverse current chromatogram, obtains high purity product（99% or more）, while yield is improved, it has a good application prospect.
Description
Technical field
The invention belongs to field of natural product extraction, are related to a kind of isolation and purification method of rhodioside, more particularly to
A kind of method that Simulation moving bed combination high speed adverse current chromatogram isolates and purifies rhodioside.
Background technology
The chemical composition of rhodiola root mainly has flavonoids, tyrosol, rhodioside (Salidroside), sitosterol, organic
Acid, volatile oil, polysaccharide, fat, protein etc..Wherein, rhodioside and its tyrosol are the main effective ingredients of rhodiola root,
The extraction of middle rhodioside and separation method mainly have chromatography, ultrafiltration purification method, alcohol precipitation method of purification, macroreticular resin absorbing method
Deng.Wherein, macroreticular resin absorbing method use is more universal, but only relies on a kind of separation method of macroporous absorbent resin, and what is obtained is red
Red-spotted stonecrop glycoside product purity or relatively low.
Patent CN201410450304.8 discloses a kind of method for extracting rhodioside from rhodiola root, using macropore tree
Fat absorption and purification, purity can reach 98.4%, but yield is relatively low；Patent CN201310463903.9 discloses a kind of from red
The method that rhodioside is extracted in red-spotted stonecrop, using macroporous resin purification and Simulation moving bed purify associated with mode detach it is pure
Change, although the purity of extraction product is higher, operating process is more complex, and yield is relatively low.Patent CN021004897 discloses one
Kind is by the method for the extraction rhodioside of high speed adverse current chromatogram twice, and the purity for extracting product is higher, but yield is relatively low.
In order to overcome the defect of existing method, the application using Simulation moving bed with it is high speed adverse current chromatograph joint used, both ensured
Purity, also improves yield.
Invention content
Present invention aims at providing a kind of isolation and purification method of rhodioside, this method be a kind of extraction efficiency it is high,
Isolate and purify it is with obvious effects and also extraction product purity it is good, high income has a good application prospect.
Purpose of the present invention is to what is be achieved through the following technical solutions：
A kind of isolation and purification method of rhodioside, includes the following steps：
（1）Extraction：After rhodiola root drying and crushing, continuous countercurrent extracting tank is added, is extracted with water as solvent, filters, obtain
Rhodioside extracting solution is obtained, rhodioside crude extract is concentrated under reduced pressure to obtain；
（2）Simulation moving bed purifies：After crude extract in step (1) is dissolved with ethyl alcohol, pass through Simulated Moving Bed Chromatography
Separation is enriched with the component containing rhodioside；Wherein, the adsorbent of Simulated Moving Bed Chromatography filling is silica gel, and eluant, eluent is body
Product ratio 1:13 methanol:Ethyl acetate solution；
（3）High speed adverse current chromatogram purifies：By step（2）It is enriched with the obtained component containing rhodioside to be concentrated to dryness, add
Ethyl alcohol dissolves, and is detached with high-speed countercurrent chromatography, and the component containing rhodioside is collected, and evaporated under reduced pressure obtains rhodiola root
Glycosides sterling.
Further, as a preferred option, in step（2）Simulation moving bed purifying in, adsorption zone flow velocity be 2-
4BV/h, preferably 2BV/h；Elution zone 3~4BV/h of flow velocity, preferably 3BV/h；Switching time is 600~800s, preferably 700s；Temperature
Degree control is at 35 DEG C~45 DEG C；Pressure is controlled in 0.3MPa~0.5MPa.
Further, as a preferred option, step（3）Stationary phase in the high-speed countercurrent chromatography and mobile phase
It is prepared as follows：By stratification after hexamethylene, n-butanol, first alcohol and water mixing, upper layer solvent is collected respectively under
Layer solvent, ultrasonic respectively, using upper layer solvent as stationary phase, lower layer's solvent is mobile phase.
In a preferred embodiment, above-mentioned hexamethylene, n-butanol, methanol, water volume ratio be 1.5-3.5：2.0-3.5：
1.0-2.5：3.0-6.0 more preferably 3.0-3.5：2.5-3.0：1.0-2.0：3.0-4.5 most preferably 3：2.5：1.5：3.5.
Compared with prior art, the present invention advantageous effect is：
1）Using Simulation moving bed with it is high speed adverse current chromatograph joint used, and both ensure that and carried using specific chromatographic solvent system
Take the high-purity of product（99% or more）, also substantially increase recovery rate.
2）The present invention extracts rhodioside using Continuous Countercurrent Extraction method, helps to improve recovery rate.
It is further illustrated the present invention below in conjunction with specific embodiment, but the scope of protection of present invention not office
It is limited to following embodiments.
Specific implementation mode
Embodiment 1
After dry rhodiola root 2kg is crushed, it is added in continuous countercurrent extracting tank, and 10kg water, refluxing extraction is added
3h is filtered, and concentration obtains rhodioside crude extract；It after being dissolved with absolute ethyl alcohol, is detached, is enriched with by Simulated Moving Bed Chromatography
Component containing rhodioside；Wherein, the adsorbent of Simulated Moving Bed Chromatography filling is silica gel, and eluant, eluent is volume ratio 1:13
Methanol:Ethyl acetate solution；Adsorption zone flow velocity is 2BV/h；Elution zone flow velocity 3BV/h；Switching time is 700s；Temperature control exists
40 DEG C or so；Pressure is controlled in 0.4MPa；The component containing rhodioside that enrichment obtains is concentrated to dryness, ethyl alcohol is added to dissolve,
Purified with high-speed countercurrent chromatography, wherein the stationary phase in high-speed countercurrent chromatography and mobile phase are made as follows
It is standby：By hexamethylene：N-butanol：Methanol：Water=3：2.5：1.5：3.5 ratio will be after hexamethylene, n-butanol, first alcohol and water mixing
Stratification collects upper layer solvent and lower layer's solvent, respectively ultrasound respectively, and using upper layer solvent as stationary phase, lower layer's solvent is stream
Dynamic phase, collects the component containing rhodioside, and evaporated under reduced pressure obtains rhodioside sterling 19.63g, HPLC:99.32%；
Embodiment 2
After dry rhodiola root 1kg is crushed, it is added in continuous countercurrent extracting tank, and 5kg water, refluxing extraction is added
3h is filtered, and concentration obtains rhodioside crude extract；It after being dissolved with absolute ethyl alcohol, is detached, is enriched with by Simulated Moving Bed Chromatography
Component containing rhodioside；Wherein, the adsorbent of Simulated Moving Bed Chromatography filling is silica gel, and eluant, eluent is volume ratio 1:13
Methanol:Ethyl acetate solution；Adsorption zone flow velocity is 2BV/h；Elution zone flow velocity 3BV/h；Switching time is 700s；Temperature control exists
40 DEG C or so；Pressure is controlled in 0.4MPa；The component containing rhodioside that enrichment obtains is concentrated to dryness, ethyl alcohol is added to dissolve
Afterwards, purified with high-speed countercurrent chromatography, wherein the stationary phase in high-speed countercurrent chromatography and mobile phase be as follows
It prepares：By hexamethylene：N-butanol：Methanol：Water=3：2.5：1.5：3.5 ratio is by hexamethylene, n-butanol, first alcohol and water mixing
Stratification afterwards collects upper layer solvent and lower layer's solvent, respectively ultrasound respectively, and using upper layer solvent as stationary phase, lower layer's solvent is
Mobile phase, collects the component containing rhodioside, and evaporated under reduced pressure obtains rhodioside sterling 10.42g, HPLC:99.27%；
Although present invention has been a degree of descriptions, it will be apparent that, do not departing from the spirit and scope of the present invention
Under the conditions of, the appropriate variation of each condition can be carried out.It is appreciated that the present invention is not limited to the embodiments, and it is attributed to right
It is required that range comprising the equivalent replacement of each factor.
Claims (2)
1. a kind of isolation and purification method of rhodioside, includes the following steps：
（1）Extraction：After rhodiola root drying and crushing, continuous countercurrent extracting tank is added, is extracted with water as solvent, filter, decompression is dense
Contract to obtain rhodioside crude extract；
（2）Simulation moving bed detaches：After the crude extract that step (1) obtains is dissolved with ethyl alcohol, pass through Simulated Moving Bed Chromatography point
From component of the enrichment containing rhodioside；Wherein, the adsorbent of Simulated Moving Bed Chromatography filling is silica gel, and eluant, eluent is volume
Than 1:13 methanol:Ethyl acetate solution；Adsorption zone flow velocity is 2-4BV/h；Elution zone flow velocity is 3~4BV/h；Switching time is
600~800s；Temperature is controlled at 35 DEG C~45 DEG C；Pressure is controlled in 0.3MPa~0.5MPa；
（3）High speed adverse current chromatogram purifies：By step（2）It is enriched with the obtained component containing rhodioside to be concentrated to dryness, adds ethyl alcohol
Dissolving, is detached with high-speed countercurrent chromatography, collects the component containing rhodioside, and it is pure to obtain rhodioside for evaporated under reduced pressure
Product, wherein the stationary phase and mobile phase of the high-speed countercurrent chromatography are prepared as follows：Hexamethylene by volume:
N-butanol:Methanol:Water=3：2.5：1.5：Stratification after 3.5 mixings is collected upper layer solvent and lower layer's solvent, is surpassed respectively respectively
Sound, using upper layer solvent as stationary phase, lower layer's solvent is mobile phase.
2. isolation and purification method according to claim 1, it is characterised in that：In step（2）Simulation moving bed purifying in,
Adsorption zone flow velocity is 2BV/h；Elution zone flow velocity is 3BV/h；Switching time is 700s.
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| CN1365980A (en) * | 2002-02-06 | 2002-08-28 | 北京天纯维通生物技术有限公司 | Process for preparing high-purity rhodioloside |
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| CN103467540A (en) * | 2013-10-09 | 2013-12-25 | 白心亮 | Method for extracting salidroside from rhodiola |
| CN104173416A (en) * | 2014-09-04 | 2014-12-03 | 南京标科生物科技有限公司 | Method for extracting salidroside from rhodiola rosea |
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| CN1365980A (en) * | 2002-02-06 | 2002-08-28 | 北京天纯维通生物技术有限公司 | Process for preparing high-purity rhodioloside |
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