CN108392500A - A method of preparing ganodenic acid - Google Patents
A method of preparing ganodenic acid Download PDFInfo
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- CN108392500A CN108392500A CN201810295221.4A CN201810295221A CN108392500A CN 108392500 A CN108392500 A CN 108392500A CN 201810295221 A CN201810295221 A CN 201810295221A CN 108392500 A CN108392500 A CN 108392500A
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- ganoderma lucidum
- extract
- ganodenic acid
- extraction
- preparing
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/06—Fungi, e.g. yeasts
- A61K36/07—Basidiomycota, e.g. Cryptococcus
- A61K36/074—Ganoderma
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/37—Extraction at elevated pressure or temperature, e.g. pressurized solvent extraction [PSE], supercritical carbon dioxide extraction or subcritical water extraction
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention discloses a kind of methods preparing ganodenic acid, and this method comprises the following steps：Ganoderma lucidum fruitbody is added to 50 100% ethyl alcohol, liquid material mass ratio 30 80:1,55 100 DEG C of Extracting temperature, 13 hours extraction times, extracting solution is concentrated to give ganoderma lucidum alcohol extract；Ganoderma lucidum fruitbody is processed into 10 80 mesh granule sizes, ganoderma lucidum alcohol extract mixing is added, is then placed in postcritical extractor, carries out supercritical CO2Extraction；65 DEG C of extract or less concentrates and drying, obtains Ganodenna Lucidum P.E.The method for preparing ganodenic acid of the present invention, the ganodenic acid extracted, when acting on a concentration of 100ug/mL, the inhibiting rate that the inhibiting rate to human prostate tumour cell LNCaP is 66.76%, 22RV1 is 62.69%.
Description
Technical field
The present invention relates to the field of deep of edible and medicinal fungi, more particularly to a kind of method preparing ganodenic acid.
Technical background
Ganoderma lucidum (Ganoderma lucidum) belongs to list Gammaproteobacteria, and Polyporaceae has tonifying middle-Jiao and Qi, strengthens the body resistance to consolidate the constitution, macrobiosis
Lengthen one's life and other effects, it is a kind of Chinese medicine of preciousness, is known as the reputation of " celestial grass ".Research shows that ganoderma lucidum have anti-aging, adjust it is immune,
Liver protection toxin expelling inhibits tumour, antibacterial, antiviral and other effects.Ganoderma lucidum contains multiple biological activities ingredient, including triterpene, polysaccharide, steroid
Alcohol, alkaloid etc..Ganodenic acid and ganoderma lucidum polysaccharide are the main active materials in ganoderma lucidum.
The method of extraction ganodenic acid mainly has：Organic solvent extraction, ultrasonic extraction and supercritical carbon dioxide
Extraction.Traditional extracting process mainly extracts triterpene using organic solvent from ganoderma lucidum fruitbody, and this method consumption has
Solvent is more, time-consuming；Most supercritical technology is widely used in the extraction of ganoderma lucidum spore oil, and ganoderma lucidum fruitbody
Supercritical extract generally existing extraction efficiency it is low, of high cost and active low the problems such as.It is high therefore, it is necessary to develop a kind of recovery rate
But lucid ganoderma triterpene extraction method at low cost.
Invention content
The purpose of the present invention is to provide a kind of methods preparing ganodenic acid, and this method comprises the following steps：
1. ganoderma lucidum fruitbody to be added to the ethyl alcohol of 50-100%, liquid material mass ratio 30-80:1,55-100 DEG C of Extracting temperature,
Extraction time 1-3 hour, extracting solution are concentrated to give ganoderma lucidum alcohol extract；
2. ganoderma lucidum fruitbody is processed into 10-80 mesh granule sizes, the ganoderma lucidum alcohol extract mixing of step 1. is added, then puts
Enter in postcritical extractor, carries out supercritical CO2Extraction；
3. supercritical extraction process condition is：The ethyl alcohol of 40-70 DEG C of temperature, pressure 20-50Mpa, 50-100% (V/V) is done
For entrainer, dosage 4-10mL/g, time 1-3h；
4. 65 DEG C of extract or less concentrates and drying, Ganodenna Lucidum P.E is obtained.
Wherein step 1. in：
Containing the ethyl alcohol that mass fraction is 2%-20%, the wherein content of ethyl alcohol in the ganoderma lucidum alcohol extract being concentrated to give
It is that ethyl alcohol yield is calculated and obtained when extracting solution concentrates；
Wherein step 2. in：
The mass ratio of the sesame fructification and ganoderma lucidum alcohol extract is 10:1-1:10；
The CO2Purity is 99-100%；
Supercritical extraction process condition is：40-60 DEG C of temperature, pressure 20-35Mpa, 80-100% (V/V) ethyl alcohol is as folder
Band agent, dosage 4-8mL/g, time 1-3h.
This law combines circumfluence distillation and means of supercritical extraction, greatly reduces the consumption of Extraction solvent, reduces extraction
Time improves extraction efficiency, while also protecting the activity of fruiting body extract of Ganoderma Lucidum.
Present invention incorporates two kinds of extractive techniques：It is first carried out using the hot technique of backflow of extensive extraction ganodenic acid preliminary
Then extraction uses the supercritical extraction technique of green high-efficient further to extract.The result shows that：Effective combination of two methods,
Ganodenic acid extraction efficiency is improved, the time of circumfluence distillation is shortened, not only reduces energy consumption, and reduce extract
The component damages of middle thermal sensitivity improve the activity of Ganodenna Lucidum P.E, and the ganodenic acid extracted has hyperplasia of prostate
Very high bioactivity.
The present invention relates to a kind of method of extraction ganodenic acid, the ganodenic acid extracted has prostate related disease
There is good effect.As a concentration of 100ug/mL of ganodenic acid sample effect, the inhibiting rate of prostate tumor cells LNCaP is
The inhibiting rate of 66.76%, 22RV1 are 62.69%, and inhibition is close to 400 μM of positive drug Finasteride.
The ganodenic acid preparation method of the present invention, by traditional ganoderma lucidum alcohol extract and ganoderma lucidum fruitbody mixing, using green
Efficient supercritical technology deep processing produces active components of glossy ganoderma, extraction efficiency can be made to greatly improve, substantially reduce extraction
Cost, activity also have good promotion, can in nutrition and health care and field of medicaments new product and raw material technical support is provided.
Description of the drawings
The ganoderma lucidum extract of Fig. 1 embodiments 1 inhibits LNCaP cells and 22RV1 cell activity to compare
Wherein, the F in abscissa is Finasteride
Specific implementation mode
With reference to example, the present invention will be further described in detail.
Embodiment 1
No. 1 (Academy of Agricultural Sciences, Shanghai City) fructification of Shanghai agriculture ganoderma lucidum (G.lucidum) that the place of production is Longquan, Zhejiang Province is crushed
20 mesh sieve is crossed afterwards, is weighed 1000g and is placed in extractor, 80% ethyl alcohol, liquid material mass ratio 40 is added:1,85 DEG C of Extracting temperature,
Extracting solution filtering and concentrating obtains ganoderma lucidum alcohol extract 88.83g after extraction 3h, is labeled as I, contains 10% ethyl alcohol.
Ganoderma lucidum fruitbody is processed into 60 mesh granule sizes, by the medicinal extract shape ganoderma lucidum alcohol extract I and ganoderma lucidum fruitbody of preparation
With mass ratio for 1:Mixing is added in 1 ratio, then weighs 40g mixtures and is put into postcritical extractor, carries out supercritical CO2
Extraction, extracting factor are：40 DEG C of temperature, pressure 30Mpa, the entrainment of 90% ethyl alcohol, entrainer dosage 6mL/g, time 1h.
After extractions, extract liquor, 65 DEG C of concentrations and drying are collected from separating still discharge port, obtains ganoderma lucidum extract 4.09g,
Extraction yield is 10.2%.According to 2015 pharmacopeia, using oleanolic acid as reference substance, it is 35.91% to measure ganodenic acid content.
The computational methods of ganodenic acid content (2015 pharmacopeia measure ganodenic acid content method)：
1. the preparation of reference substance solution takes oleanolic acid reference substance appropriate, accurately weighed, adds methanol that every 1mL is made and contain
The solution of 0.2mg to get.
2. the preparation precision of standard curve measures reference substance solution 0.1,0.2,0.3,0.4,0.5mL, 15mL tools are set respectively
It fills in test tube, volatilizes, let cool, (precision weighs vanillic aldehyde 0.5g, vinegar on the rocks to the vanillic aldehyde glacial acetic acid solution that precision addition is newly prepared
Acid make to be dissolved into 10mL to get) 0.2mL, perchloric acid 0.8mL, shake up, heated 15 minutes in 70 DEG C of water-baths, set ice water immediately
It is 5 minutes cooling in bath, it takes out, ethyl acetate 4mL is added in precision, shakes up, using corresponding reagent as blank, according to UV-vis spectroscopy
Photometry (general rule 0401) measures absorbance at 546nm wavelength, and mark is drawn by ordinate, a concentration of abscissa of absorbance
Directrix curve.
3. the preparation of test solution takes the ganoderma lucidum extract powder 2g being prepared, accurately weighed, conical flask with cover is set
In, add ethyl alcohol 50mL, be ultrasonically treated (power 140W, frequency 42kHz) 45 minutes, filtration, filtrate is set in 100mL measuring bottles, with suitable
Measure ethyl alcohol, gradation washing nozzle and filter residue in washing lotion and the same measuring bottle of people, add ethyl alcohol to scale, shake up to get.
4. measuring method precision measures test solution 0.2mL, set in 15mL tool plug test tubes, under sighting target directrix curve preparation
Method is operated from " volatilizing " with method, measures absorbance, and oleanolic acid contains from reading test solution on standard curve
Amount, calculate to get.
This product is calculated by dry product, containing triterpene and sterol with oleanolic acid (C30H48O3) meter, 0.50% must not be less than.
Embodiment 2
No. 1 (Academy of Agricultural Sciences, Shanghai City) fructification of Shanghai agriculture ganoderma lucidum (G.lucidum) that the place of production is Longquan, Zhejiang Province is crushed
10 mesh sieve is crossed afterwards, 1000g is weighed and is placed in extractor, 90% ethyl alcohol is added, and liquid material mass ratio is 40:1, Extracting temperature 90
DEG C, filtering and concentrating obtains ganoderma lucidum alcohol extract 81.49g after extracting 2h, is labeled as II, contains 5% ethyl alcohol.
Ganoderma lucidum fruitbody is processed into 80 mesh granule sizes, by the medicinal extract shape ganoderma lucidum alcohol extract II and ganoderma lucidum fruitbody of preparation
It is 1 according to mass ratio:Mixing is added in 1 ratio, then weighs 40g mixtures and is put into postcritical extractor, carries out overcritical
CO2Extraction, extracting factor are：Temperature 50 C, pressure 35Mpa, the entrainment of 90% ethyl alcohol, entrainer dosage 6mL/g, time
1.5h。
After extractions, extract liquor, 65 DEG C of concentrations and drying are collected from separating still discharge port, obtains ganoderma lucidum extract 5.37g,
Extraction yield is 13.4%.According to 2015 pharmacopeia, using oleanolic acid as reference substance, it is 38.43% to measure ganodenic acid content.
Embodiment 3
The inhibiting rate of LNCaP cells detects
It is 5 by cell concentration4The tumour cell LNCaP of a/mL is (purchased from Chinese Academy of Sciences's Shanghai school of life and health sciences cell money
Source center) suspension 180 μ L be added in 96 orifice plates, 20 μ L measuring samples (the ganoderma lucidum extract of embodiment 1, heat are added after 48h
Refluxing extraction, Soxhlet extraction, ultrasonic extraction and cold soaking extract the Ganodenna Lucidum P.E that four kinds of methods are prepared), it is the moon with DMSO
Property control, Finasteride is positive control, and each sample sets 3 repetitions, in 37 DEG C, the CO of 5% concentration2Under the conditions of cultivate 48h
Afterwards, it sucks old culture medium and colourless 1640 culture mediums of 180 μ L (Thermo Fisher Scientific companies of the U.S.), 20 μ L is added
The Alamar Blue reagents (Thermo Fisher Scientific companies of the U.S.) of 0.075mg/mL, with enzyme-linked after changing colour
Immune detector surveys light absorption value under 570 and 600nm, and the influence of sample cell proliferation is calculated with formula.
As a concentration of 100ug/mL of the ganoderma lucidum extract sample effect of embodiment 1, the inhibiting rate of LNCaP cells is
66.76%.
Embodiment 4
The inhibiting rate of 22RV1 cells detects
It is 5 × 10 by cell concentration4A/mL tumour cells 22RV1 (is purchased from Chinese Academy of Sciences's Shanghai school of life and health sciences cell
Resource center) suspension 180 μ L be added in 96 orifice plates, after for 24 hours afterwards the extract samples of 20 μ L embodiments 1 is added, be with DMSO
Negative control, Finasteride are positive control, and each sample sets 3 repetitions, in 37 DEG C, the CO of 5% concentration2Under the conditions of cultivate
After 72h, sucks old culture medium and be added colourless 1640 culture mediums of 180 μ L (Thermo Fsher Scientific companies of the U.S.), 20
The Alamar Blue reagents (Thermo Fisher Scientific companies of the U.S.) of μ L 0.075mg/mL, use enzyme after changing colour
Connection immune detector surveys light absorption value under 570 and 600nm, and the influence of sample cell proliferation is calculated with formula.
As a concentration of 100 μ g/mL of the ganoderma lucidum extract sample effect of embodiment 1, the suppression of prostate tumor cells 22RV1
Rate processed is 62.69%.
Claims (3)
1. a kind of method preparing ganodenic acid, it is characterised in that this method comprises the following steps：
1. ganoderma lucidum fruitbody to be added to the ethyl alcohol of 50-100%, liquid material mass ratio 30-80:1,55-100 DEG C of Extracting temperature, extraction
Time 1-3 hour, extracting solution are concentrated to give ganoderma lucidum alcohol extract；
2. ganoderma lucidum fruitbody is processed into 10-80 mesh granule sizes, the ganoderma lucidum alcohol extract mixing of step 1. is added, is then placed in super
In critical extractor, supercritical CO is carried out2Extraction；
3. supercritical extraction process condition is：40-70 DEG C of temperature, pressure 20-50Mpa, 50-100% (V/V) ethyl alcohol is as entrainment
Agent, dosage 4-10mL/g, time 1-3h；
4. 65 DEG C of extract or less concentrates and drying, Ganodenna Lucidum P.E is obtained.
2. the method according to claim 1 for preparing ganodenic acid, it is characterised in that wherein step 1. in：
Containing the ethyl alcohol that mass fraction is 2%-20% in the ganoderma lucidum alcohol extract being concentrated to give.
3. the method according to claim 1 for preparing ganodenic acid, it is characterised in that wherein step 2. in：
The mass ratio of the ganoderma lucidum fruitbody and ganoderma lucidum alcohol extract is 10:1-1:10；
The CO2Purity is 99-100%；
Supercritical extraction process condition is：40-60 DEG C of temperature, pressure 20-35Mpa, 80-100% (V/V) ethyl alcohol is as entrainment
Agent, dosage 4-8mL/g, time 1-3h.
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| CN201810295221.4A CN108392500B (en) | 2018-03-30 | 2018-03-30 | Method for preparing ganoderma triterpene |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109394799A (en) * | 2018-12-28 | 2019-03-01 | 南京中科药业有限公司 | Natural drug composition of the extract containing ganoderma lucidum and its preparation method and application |
| CN111346118A (en) * | 2020-03-31 | 2020-06-30 | 福建仙芝楼生物科技有限公司 | Method for subcritical water extraction and separation of ganoderma triterpene extract |
| CN111686136A (en) * | 2019-03-15 | 2020-09-22 | 乔璞科技有限公司 | Method for purifying triterpenoids |
| CN113150867A (en) * | 2020-12-01 | 2021-07-23 | 中科健康产业集团股份有限公司 | Preparation method of ganoderma lucidum extract oil rich in ganoderma lucidum triterpenes |
| CN115919908A (en) * | 2022-12-20 | 2023-04-07 | 中科健康产业集团江苏药业有限公司 | Ganoderma spore oil-containing composition for improving tumor inhibition rate and preparation method thereof |
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| CN102293789A (en) * | 2011-09-06 | 2011-12-28 | 上海市农业科学院 | Method for extracting triterpenoids from ganoderma lucidum sporocarp |
| CN105837700A (en) * | 2016-04-12 | 2016-08-10 | 江苏江大源生态生物科技股份有限公司 | A comprehensive extraction, utilization and production method for glossy ganoderma sporocarps and spores |
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| CN102293789A (en) * | 2011-09-06 | 2011-12-28 | 上海市农业科学院 | Method for extracting triterpenoids from ganoderma lucidum sporocarp |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109394799A (en) * | 2018-12-28 | 2019-03-01 | 南京中科药业有限公司 | Natural drug composition of the extract containing ganoderma lucidum and its preparation method and application |
| CN109394799B (en) * | 2018-12-28 | 2021-05-28 | 南京中科药业有限公司 | Natural pharmaceutical composition containing ganoderma lucidum extract and preparation method and application thereof |
| CN111686136A (en) * | 2019-03-15 | 2020-09-22 | 乔璞科技有限公司 | Method for purifying triterpenoids |
| CN111346118A (en) * | 2020-03-31 | 2020-06-30 | 福建仙芝楼生物科技有限公司 | Method for subcritical water extraction and separation of ganoderma triterpene extract |
| CN111346118B (en) * | 2020-03-31 | 2022-07-05 | 福建仙芝楼生物科技有限公司 | Method for subcritical water extraction and separation of ganoderma triterpene extract |
| CN113150867A (en) * | 2020-12-01 | 2021-07-23 | 中科健康产业集团股份有限公司 | Preparation method of ganoderma lucidum extract oil rich in ganoderma lucidum triterpenes |
| CN115919908A (en) * | 2022-12-20 | 2023-04-07 | 中科健康产业集团江苏药业有限公司 | Ganoderma spore oil-containing composition for improving tumor inhibition rate and preparation method thereof |
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