CN108003211A - A kind of method of quick separating ganoderic acid in accessory substance from ganoderma lucidum - Google Patents
A kind of method of quick separating ganoderic acid in accessory substance from ganoderma lucidum Download PDFInfo
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- CN108003211A CN108003211A CN201711399923.9A CN201711399923A CN108003211A CN 108003211 A CN108003211 A CN 108003211A CN 201711399923 A CN201711399923 A CN 201711399923A CN 108003211 A CN108003211 A CN 108003211A
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- Prior art keywords
- ganoderma lucidum
- ganoderic acid
- acid
- accessory substance
- ganoderic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
- C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton
Abstract
The method that the present invention discloses quick separating ganoderic acid in a kind of accessory substance from ganoderma lucidum.Method of the present invention from the accessory substance quick separating high level ganoderic acid of Ganodenna Lucidum P.E, pressure prepares ganoderma lucidum acid blend in first Flash, 3 higher degree compounds are prepared through Prep high pressures again, are ganoderic acid A, ganoderic acid B and ganoderic acid C through 3 compounds of Structural Identification2, Quality Identification and monitoring which can be as reference substance for ganoderma lucidum and ganoderma lucidum product.The present invention provides a kind of ganoderma lucidum accessory substance, and fast purifying prepares ganoderic acid, has high commercial value and extensive market prospects.The preparation method has the advantages that efficient, quick, preparation amount is big, can provide scientific basis as Quality Identification of the ganoderic acid reference substance for ganoderma lucidum and products thereof and monitoring, while for the production of high-purity ganoderic acid.
Description
Technical field
The invention belongs to extraction purification technical field, particularly one kind quickly to prepare ganoderic acid side from ganoderma lucidum accessory substance
Method.
Background technology
Ganoderma lucidumGanoderma lucidumIt is a kind of large-scale medicinal fungi,《Chinese Pharmacopoeia》Described in ganoderma lucidum include
Red sesameGanoderma lucidum(Levss. Ex：Fr.) P.Karst. or purple sesameG.sinense. Dry son it is real
Body.Ganoderma lucidum is a kind of Chinese medicine, with a long history in China, first recorded in《Sheng Nong's herbal classic》, have tonifying middle-Jiao and Qi, enriching yin it is strong,
Strengthen the body resistance to consolidate the constitution, promote longevity and other effects.Wherein triterpene and polysaccharide are most important two big active ingredients of ganoderma lucidum.Modern pharmacological research
Show, ganoderma lucidum triterpene compounds have liver protection, antitumor, immunological regulation, suppress angiotensins and anti-oxidant and other effects.
Ganoderic acid is most important active ingredient in ganoderma lucidum triterpene compounds, but since its content is low, and structure phase
Closely, separation and purge process are complicated.At present, ganoderma lucidum triterpene compounds are isolated and purified, is to pass through one or more mostly
Chromatography enriching and purifying repeatedly, the effect of separating-purifying is reached with reference to isolation technics such as liquid phantom preparing chromatogram or crystallizations.According to 2010
Year Che-ng C R etc.（Cheng C R,Yue Q X,Wu Z Y,etal.Cytotoxictriterpenoids from
Ganodermalucidum ［ J ］ .Phytochem Anal, 2010,71: 1579.）Ganoderma lucidum fruitbody, stone are extracted with alcohol reflux
Oily ether, dichloromethane extract to obtain triterpenes crude extract；Again through silica gel and Sephadex LH-20 enriching and purifyings, petroleum ether-chlorine
Imitation-carbinol gradient elution；Gained each group lease making recrystallizes and liquid phase prepares column and is further purified to obtain triterpenes monomer 43.
Li Yingbo in 2013（Li Yingbo are efficiently separated from ganoderma lucidum mycelium on research [D] for preparing antitumor ganodenic acid monomer
Sea:East China University of Science Ph.D. Dissertation, 2013）Prepare using silica gel column chromatography, thin-layer chromatography and partly high-efficient liquid phase color
The separation methods such as spectrum, separate and identify eight ganodenic acid monomers from Ganoderma lucidum mycelium.Zhu Zhong in 2013 is quick etc.（Zhu Zhongmin, Lee
Bright, the such as Zhou Yanfei macroreticular resins chromatography isolates and purifies ganoderic acid [C] Foochow with reference to high speed adverse current chromatogram:Ganoderma lucidum production in 2013
Product research and development scientific seminar, 2013:40-44.）It is pure to employ the separation of macroporous absorbent resin combination high-speed countercurrent chromatography
Change obtains 3 kinds of ganoderic acids.The obtained high-purity ganoderic acid content of column chromatography is seldom, it is difficult to carries out the side such as pharmacology and toxicology
The research in face, therefore, the technology for studying the large capacity fast separating and purifying of ganoderic acid have great importance.
Ganoderic acid component species is various, structure is similar, and extraction and separation process is still unstable, and standard items are difficult to obtain, finally
Cause ganoderic acid component qualitative and quantitative analysis difficult, so ganoderma lucidum and products thereof lacks the quality control of science.
The content of the invention
It is an object of the invention in place of overcome the deficiencies in the prior art, and provide it is a kind of efficiently, quick, preparation amount it is big
A kind of method of quick separating ganoderic acid in accessory substance from ganoderma lucidum.
A kind of method of quick separating ganoderic acid in accessory substance from ganoderma lucidum, with the following method:
（1）Ganoderma lucidum by-product raw material is weighed, adds a certain amount of solvent, solvent or be absolute ethyl alcohol or methanol, ethyl acetate, chlorine
Imitative, methanol-chloroform, ethyl acetate-chloroform, chloroform-methanol-water, ratio 1:5, ultrasonic dissolution, supernatant is taken after solution centrifugation
Liquid crosses 0.45 μm of filter membrane, obtains ganoderma lucidum stoste, is suppressed in spare；
（2）HPLC measure on the standby liquid being collected into is suppressed in Flash, respectively obtains ganoderic acid A, B, C2Mixture, water-bath are steamed
It is dry, prepared for high pressure spare；
（3）Ganoderic acid A, B, C2After mixture is evaporated, proper amount of methanol dissolving is added, crosses film, filtrate prepares into horizontal high voltage and purifies,
Prep high pressures prepare HPLC measure on the liquid being collected into, and respectively obtain ganodenic acid monomer, then are recrystallized, and obtain ganoderic acid
Sterling.
The ganoderma lucidum accessory substance can also directly be cut into slices using ganoderma lucidum, or be replaced with Ganodenna Lucidum P.E, or with ganoderma lucidum product
Generation.
The ganoderma lucidum accessory substance is processed in concentration process selected from ganoderma lucidum, is trapped in the water-insoluble of concentration pot bottom.
The pillar prepared used in liquid phase is reversed-phase column, and the middle standby column of compacting can use Reveleris C18-WP series of columns；It is high
Compacting is standby to prepare column using YMC-Triart series C18（150*20,5 μm）, or Waters preparation chromatographic columns
（SunFireTM Prep C18 OBDTM 19*250mm, 5 μm）
In summary, present invention advantage following compared with prior art：
The present invention selects the ganoderma lucidum accessory substance in extraction workshop, its ganoderic acid A, B and C2Content is up to 15%~20%, is ganodenic acid
Abundant source.Preparative chromatograph is rapidly purified using holography, pressure prepares ganoderma lucidum acid blend in first Flash, then passes through
Prepared by Prep high pressures, recrystallization obtains 3 higher degree compounds, is ganoderic acid A through 3 compounds of Structural Identification, ganoderic acid B
And ganoderic acid C2.The preparation method have the advantages that efficiently, quick, preparation amount is big, ganoderic acid reference substance can be used as ganoderma lucidum and
The Quality Identification of its product and monitoring, while provide scientific basis for the production of high-purity ganoderic acid.
Brief description of the drawings
The efficient liquid phase of ganoderic acid content in Fig. 1 ganoderma lucidum paste accessory substances（HPLC）Chromatogram.
Standby collection of illustrative plates is suppressed in Fig. 2 ganoderma lucidum paste accessory substances Flash.
The HPLC chromatogram for the ganoderma lucidum acid blend 1 being prepared is pressed in Fig. 3.
The HPLC chromatogram for the ganoderma lucidum acid blend 2 being prepared is pressed in Fig. 4.
The HPLC chromatogram for the ganoderma lucidum acid blend 3 being prepared is pressed in Fig. 5.
The Prep high pressures of Fig. 6 ganoderma lucidums acid blend 1 prepare collection of illustrative plates.
The Prep high pressures of Fig. 7 ganoderma lucidums acid blend 2 prepare collection of illustrative plates.
The HPLC chromatogram for the compound 1 that Fig. 8 high pressures are prepared.
The HPLC chromatogram for the compound 2 that Fig. 9 high pressures are prepared.
The HPLC chromatogram for the compound 3 that Figure 10 high pressures are prepared.
Embodiment
The present invention is described in more detail with reference to embodiment.
Embodiment 1
A kind of method of quick separating ganoderic acid in accessory substance from ganoderma lucidum, with the following method:
（1）Glossy ganoderma extract by-product raw material is weighed, adds a certain amount of absolute ethyl alcohol, ratio 1:5, ultrasonic dissolution, solution centrifugation
After take supernatant to cross 0.45 μm of filter membrane, obtain ganoderma lucidum stoste, suppressed in spare；
（2）HPLC measure on the standby liquid being collected into is suppressed in Flash, respectively obtains ganoderic acid A, B, C2Mixture, water-bath are steamed
It is dry, prepared for high pressure spare；
（3）Ganoderic acid A, B, C2After mixture is evaporated, proper amount of methanol dissolving is added, crosses film, filtrate prepares into horizontal high voltage and purifies,
Prep high pressures prepare HPLC measure on the liquid being collected into, and respectively obtain ganodenic acid monomer, then are recrystallized, and obtain ganoderic acid
Sterling.
Illustrated below by taking specific experiment as an example：
（1）Sample pre-treatments take 20g glossy ganoderma extracts accessory substance to grind, and add 100mL absolute ethyl alcohols（Or methanol）, ultrasonic 1h, solution
In 7800 rmin-1, centrifuge 10min.Take supernatant to cross 0.45 μm of filter membrane, obtain sepia accessory substance lysate, it is spare.
（2）Standby chromatographic condition is suppressed in the middle standby ganoderic acid crude extract Flash of compacting：Grace chromatographic columns C18-WP（40g,
20μm）；Gradient elution is carried out by mobile phase of the acetum of acetonitrile -0.05%；Chromatographic condition under Flash patterns：Flow velocity 25mL/
Min, run time 10min, ultraviolet detection wavelength 254nm, sample introduction about 1.2mL；Gradient elution program：The acetic acid of acetonitrile -0.05% is molten
Liquid：0~4min：45% acetonitrile；4~4.01min：45% ~ 55% acetonitrile；4.01~10min, 55% acetonitrile.On the liquid being collected into
HPLC is measured, and respectively obtains ganoderic acid A, B, C2Mixture, water bath method are spare.
（3）High pressure prepares ganoderic acid extract ganoderic acid A, B, C2After mixture is evaporated, proper amount of methanol dissolving is added, crosses 0.45
μm filter membrane, filtrate prepare into horizontal high voltage and purify.Prep high pressures prepare chromatographic condition：Waters prepares chromatographic column（SunFireTM
Prep C18 OBDTM 5μm 19*150mm）；Gradient elution is carried out by mobile phase of the acetum of acetonitrile -0.05%；Prep moulds
Chromatographic condition under formula：Flow velocity 13mL/min, run time 43min, equilibration time 3min, ultraviolet detection wavelength 254nm, sample introduction is about
1mL；Gradient elution program：The acetum of acetonitrile -0.05%：0~29min：30% acetonitrile；29~36min：30%~50% acetonitrile；
36~36.1min, 50%~90% acetonitrile；36.1~43min, 90% acetonitrile.HPLC is measured on the liquid being collected into, and is respectively obtained
Ganoderic acid A, ganoderic acid B and ganoderic acid C2, water bath method.After recrystallization purification, identified through high performance liquid chromatography, ganoderic acid A, spirit
Sesame acid B and ganoderic acid C2Purity is all higher than 98%.
Ganoderic acid A（Ganoderic acid A）It is as follows for white crystal, its chemical structural formula：
Ganoderic acid B（Ganoderic acid B）It is as follows for white crystal, its chemical structural formula：
Ganoderic acid C2（Ganoderic acid C2）It is as follows for white crystal, its chemical structural formula：
Embodiment 2
Ganoderma lucidum accessory substance comes from manufacturing and processing equipment PQ-300 type extractors.Fed intake in the production process of ganoderma lucidum extraction with ganoderma lucidum
250kg is counted, and material-water ratio is 1 first：12, immersion 2 it is small when after, heat 95 DEG C~100 DEG C, keep 2~3 it is small when, squeezed with air,
Pressure 0.06Mpa or with vacuum filtration, pressure is -0.08Mpa, can obtain 2.2~2.5 tons of lucidum extracting liquids, and feed concentration is
0.8；Second of material-water ratio is 1：10, heating is boiled, and when holding 1.5~2 is small, is filtered with same method, can be obtained 2.0~2.2 tons
Lucidum extracting liquid, feed concentration 0.3%；Concentrated after merging secondary filtrate.In concentration process is circulated, steam heater
Bottom formed precipitation leaching paste, yield 2%, containing ganoderic acid 15~20%（With ganoderic acid A+B+C2Meter）, it is ganoderic acid original
The abundant source of material.
The efficient liquid phase of ganoderic acid content in Fig. 1 ganoderma lucidum paste accessory substances（HPLC）Chromatogram, chromatographic condition：Chromatographic column is
XB-C18 columns（150 mm × 4.6 mm, 5 μm, Welch Materials companies of the U.S.）, mobile phase is 0.05% phosphoric acid：Second
Nitrile（65∶35）, 254 nm of Detection wavelength, 35 DEG C of column temperature, sample size 10 μ L, 1 mL/min of volume flow.
Suppress standby collection of illustrative plates in Fig. 2 ganoderma lucidum paste accessory substances Flash, chromatographic condition under Flash patterns：Grace chromatographic columns
C18-WP（40g, 20 μm）；Gradient elution is carried out by mobile phase of the acetum of acetonitrile -0.05%；Chromatostrip under Flash patterns
Part：Flow velocity 25mL/min, run time 10min, ultraviolet detection wavelength 254nm, sample introduction about 1.2mL；Gradient elution program：Second
The acetum of nitrile -0.05%：0~4min：45% acetonitrile；4~4.01min：45% ~ 55% acetonitrile；4.01~10min, 55% acetonitrile.
The HPLC chromatogram for the ganoderma lucidum acid blend 1 being prepared is pressed in Fig. 3.
The HPLC chromatogram for the ganoderma lucidum acid blend 2 being prepared is pressed in Fig. 4.
The HPLC chromatogram for the ganoderma lucidum acid blend 3 being prepared is pressed in Fig. 5.
The Prep high pressures of Fig. 6 ganoderma lucidums acid blend 1 prepare collection of illustrative plates, chromatographic condition under Prep patterns：Flow velocity 13mL/min,
Run time 43min, equilibration time 3min, ultraviolet detection wavelength 254nm, sample introduction about 1mL；Gradient elution program：Acetonitrile-
0.05% acetum：0~29min：30% acetonitrile；29~36min：30%~50% acetonitrile；36~36.1min, 50%~90% second
Nitrile；36.1~43min, 90% acetonitrile.
The not described part of the present embodiment is same as the prior art.
Claims (4)
1. a kind of method of quick separating ganoderic acid in accessory substance from ganoderma lucidum, with the following method,
（1）Ganoderma lucidum by-product raw material is weighed, adds a certain amount of solvent, solvent or is absolute ethyl alcohol or is methanol or is acetic acid second
Ester is chloroform or is methanol-chloroform or is ethyl acetate-chloroform or is chloroform-methanol-water, glossy ganoderma extract accessory substance with
The ratio of each solvent is 1:5, ultrasonic dissolution, takes supernatant to cross 0.45 μm of filter membrane, obtains ganoderma lucidum stoste, suppressed in after solution centrifugation
It is spare；
（2）HPLC measure on the standby liquid being collected into is suppressed in Flash, respectively obtains ganoderic acid A, B, C2Mixture, water-bath are steamed
It is dry, prepared for high pressure spare；
（3）Ganoderic acid A, B, C2After mixture is evaporated, proper amount of methanol dissolving is added, crosses film, filtrate prepares into horizontal high voltage and purifies,
Prep high pressures prepare HPLC measure on the liquid being collected into, and respectively obtain ganodenic acid monomer, then are recrystallized, and obtain ganoderic acid
Sterling.
2. the method for quick separating ganoderic acid in the accessory substance according to claim 1 from ganoderma lucidum：The ganoderma lucidum accessory substance
Or directly to be substituted using ganoderma lucidum section, or with Ganodenna Lucidum P.E, or with ganoderma lucidum product.
3. the method for quick separating ganoderic acid in the accessory substance according to claim 1 from ganoderma lucidum：The ganoderma lucidum accessory substance choosing
Processed from ganoderma lucidum in concentration process, be trapped in the water-insoluble of concentration pot bottom.
4. the method for quick separating ganoderic acid in the accessory substance according to claim 1 from ganoderma lucidum：Prepare the column used in liquid phase
Son is reversed-phase column, and the middle standby column of compacting can use Reveleris C18-WP series of columns；Prepared by high pressure can use YMC-Triart systems
Row C18 prepares column 150*20,5 μm, or Waters prepares chromatographic column SunFireTM Prep C18 OBDTM 19*250mm, 5 μ
M separation ganoderic acids A, B, C, D.
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Cited By (3)
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| CN108267533A (en) * | 2018-04-23 | 2018-07-10 | 福建农大菌草技术开发公司 | A kind of method for building up of ganoderma lucidum molecular weight characteristic collection of illustrative plates and its application |
| CN110590891A (en) * | 2018-06-12 | 2019-12-20 | 谢天杰 | Ganoderic acid |
| CN114231587A (en) * | 2021-11-17 | 2022-03-25 | 遵义医科大学珠海校区 | Biotransformation and extraction method of ganoderic acid LTHA and LTCA |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108267533A (en) * | 2018-04-23 | 2018-07-10 | 福建农大菌草技术开发公司 | A kind of method for building up of ganoderma lucidum molecular weight characteristic collection of illustrative plates and its application |
| CN110590891A (en) * | 2018-06-12 | 2019-12-20 | 谢天杰 | Ganoderic acid |
| CN114231587A (en) * | 2021-11-17 | 2022-03-25 | 遵义医科大学珠海校区 | Biotransformation and extraction method of ganoderic acid LTHA and LTCA |
| CN114231587B (en) * | 2021-11-17 | 2023-08-08 | 遵义医科大学珠海校区 | Bioconversion and extraction method of ganoderic acid LTHA and LTCA |
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Application publication date: 20180508 |