CN103113194A - Technology for separating novel eudesmane sesquiterpenes from Phellinus igniarius - Google Patents
Technology for separating novel eudesmane sesquiterpenes from Phellinus igniarius Download PDFInfo
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- CN103113194A CN103113194A CN2012105460572A CN201210546057A CN103113194A CN 103113194 A CN103113194 A CN 103113194A CN 2012105460572 A CN2012105460572 A CN 2012105460572A CN 201210546057 A CN201210546057 A CN 201210546057A CN 103113194 A CN103113194 A CN 103113194A
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Abstract
The invention discloses a technology for separating novel eudesmane sesquiterpenes from Phellinus igniarius (Phellinus igniarius (L ex Fr) Quel, Phellinus linteus (Berk et Curt) Teng, Phellinus baumii and Phellinus hartigii (Allesch et Schnabl) Imaz). The technology comprises the following steps of preparing a crude extract of Phellinus igniarius, carrying out normal-phase silica gel chromatography, carrying out gradient elution by using chloroform and methanol, carrying out normal-phase silica gel chromatography once again, carrying out chloroform and methanol gel chromatography, carrying out normal-phase silica gel chromatography once again, and evaporating under reduced pressure, thereby obtaining novel eudesmane sesquiterpenes.
Description
Technical field
The invention belongs to the biotech medicine product field.
Background technology
Phellinus, the sporophore stockless, the flat semisphere of cap or the shape of a hoof, 2-12*3-21 centimetre, thick 1.5-10 centimetre, wooden, shallow liver brown to lead or black, often be full of cracks always, without cot, there is trickle fine hair at initial stage, rear change is without hair, the concentric ring rib is arranged. the edge is blunt, dark cinnamon is to light coffee color, downside is without thalamium. the bacterial context dark brown, firmly, wooden. tube and bacterial context are closely homochromy, multilayer, but level is not obvious, old tube layer is full of white hypha. and mouth of pipe rust brown is to dark reddish brown, circular, every millimeter 4-5. spore is subsphaeroidal, smooth, colourless, the 5-6*3-4 micron. the bristle top is sharp-pointed, base portion expands, the 10-25*5-7 micron. mycelia is branch not, without tabula, diameter 3-5 micron.
At present, the purification process of epiphyte product is more, mainly contain precipitation classification, preparation property high performance liquid chromatography, column chromatography, ultrafiltration process, centrifugation chromatography, etc. several method.And wherein use maximum column chromatographies that surely belongs to, and be divided into two classes: the one, only have the gel filtration chromatography of molecular sieve effect, gel commonly used has dextrane gel and sepharose.The 2nd, ion exchange chromatography.But, mainly for separating of polysaccharide, hyaluronic acid etc., the product that obtains after most the separation is mixture.The present invention uses multiple chromatographic technique to combine, and resolution is high, and using this invention can be exquisite to sterling.
Summary of the invention
The invention discloses a kind of Phellinus bacterium (phelliuns igniarius
Phellinus igniarius(L ex Fr) Quel, phellinus linteus
Phellinus linteus(Berk et Curt) Teng, Phellinus baumii, Kazakhstan base of a fruit phellinus
Phellinus hartigii(Allesch et Schnabl) Imaz) in 1, the isolation technique of the eudesmane type sesquiterpene that 2-is new.At first preparing the Phellinus crude extract, is then the purification on normal-phase silica gel chromatography, uses chloroform and methyl alcohol gradient elution; repeat one time the purification on normal-phase silica gel chromatography, then carry out the chloroform methanol gel chromatography, again carry out the purification on normal-phase silica gel chromatography; last evaporated under reduced pressure obtains the new eudesmane type sesquiterpene of 1,2-.
Technical scheme of the present invention is as follows:
The Phellinus crude extract is made by following method:
(1) fermentative medium formula in gram/100 milliliter is:
W-Gum 1-5% glucose 1-5%
Peptone 0.1-0.5% yeast extract paste 0.1-0.5%
Sal epsom 0.1-0.5% potassium primary phosphate 0.01-0.05%
(2) the Phellinus bacterial classification is inoculated into ordinary method in the Erlenmeyer flask that liquid nutrient medium is housed, with 20～35 ℃ of temperature, the shaking flask rotating speed is 80～280r/min, and under pH 3～8 conditions, vibrations were cultivated 7～15 days; In cultivation when the pH value drops to 2.5～4, seed in shaking flask is inoculated in the nutrient solution of 50L fermentor tank, with 20～35 ℃ of temperature, fermentor tank pressure 0.1～0.2 kg/cm, pH 3～8, air flow 0.5～1.1vvm, the condition that stirring velocity is 100～280 rev/mins, cultivated 7～15 days, and can utilize the phellinus igniarius mycelium fermentation liquid to prepare the Phellinus crude extract;
(3) get gained phellinus igniarius mycelium fermentation liquid in step (2), with its concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/2～1/5 of original volume;
(4) be that 60～95% the ethanol fermented liquid after concentrated to above-mentioned steps (3) extracts with volume percent, wherein, the amount that adds ethanol is 2～5 times of concentrated solution volume, can make that in extracting solution, alcohol concn reaches 60～90%;
(5) to step (4) gained extracting solution under 50～70 ℃ of conditions, heated 1～2 hour; Separate with ordinary method, and remove impurity by cascade filtration, separate obtaining ethanol extract; With above-mentioned ethanol extract concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/5～1/10 of original volume;
(6) just the concentrated solution of step (5) gained carries out drying with the method for frozen drying, gets the Phellinus crude extract.
The method of separating eudesmane type sesquiterpene:
Phellinus bacterium crude extract → purification on normal-phase silica gel chromatography → chloroform and methyl alcohol gradient elution → TLC detection → purification on normal-phase silica gel chromatography → chloroform methanol gel chromatography → TLC detection → purification on normal-phase silica gel chromatography → TLC detection → evaporated under reduced pressure → colorless oil (new eudesmane type sesquiterpene).
Concrete grammar is:
(1) preparation Phellinus bacterium crude extract;
(2) throw out and the purification on normal-phase silica gel mixing with step (1) gained stirs, and carries out the silica gel normal phase column chromatography after drying, uses the eluent wash-out 2-5 time, obtains elutriant;
(3) with last elutriant evaporate to dryness in step (2), the equal-volume silica gel mixed sample carries out the purification on normal-phase silica gel chromatography, uses the eluent wash-out;
(4) elutriant in collection step (3), concentrating under reduced pressure, use chloroform: methyl alcohol=1:1 dissolving, carry out the methanol gel column chromatography, use the eluent wash-out, the elutriant that uses the TLC detection to collect suitably merges elutriant, drying under reduced pressure;
(5) product that obtains in step (4) is carried out the purification on normal-phase silica gel chromatography again, use the eluent wash-out;
(6) collect the elutriant that step (5) obtains, use TLC to detect each elutriant, appropriateness merges elutriant, and drying under reduced pressure is 1,2-eudesmane type sesquiterpene.
(4) description of drawings
Fig. 1 is the structural formula of eudesmane type sesquiterpene of the present invention;
Fig. 2 is the one-dimensional nuclear magnetic resonance H spectrum of eudesmane type sesquiterpene.
(5) embodiment
Example 1:
The Phellinus crude extract is made by following method:
(1) fermentative medium formula in gram/100 milliliter is:
W-Gum 1% glucose 1%
Peptone 0.1% yeast extract paste 0.1%
Sal epsom 0.1% potassium primary phosphate 0.01%
(2) the Phellinus bacterial classification is inoculated into ordinary method in the Erlenmeyer flask that liquid nutrient medium is housed, with 25 ℃ of temperature, the shaking flask rotating speed is 110r/min, and under pH 7 conditions, vibrations were cultivated 7 days; In cultivation when the pH value drops to 3, seed in shaking flask is inoculated in the nutrient solution of 50L fermentor tank, with 25 ℃ of temperature, fermentor tank pressure 0.1 kg/cm, pH 3, air flow 0.5-1.1vvm, the condition that stirring velocity is 100 rev/mins, cultivated 7 days, and can utilize the phellinus igniarius mycelium fermentation liquid to prepare the Phellinus crude extract;
(3) get gained phellinus igniarius mycelium fermentation liquid in step (2), with its concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/3 of original volume;
(4) be that 70% the ethanol fermented liquid after concentrated to above-mentioned steps (3) extracts with volume percent, wherein, the amount that adds ethanol is 5 times of concentrated solution volume, can make that in extracting solution, alcohol concn reaches 55%;
(5) to step (4) gained extracting solution under 70 ℃ of conditions, heated 1 hour; Separate with ordinary method, and remove impurity by cascade filtration, separate obtaining ethanol extract; With above-mentioned ethanol extract concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/5 of original volume;
(6) just the concentrated solution of step (5) gained carries out drying with the method for frozen drying, gets the Phellinus crude extract.
With above-mentioned that thing takes 300g and equal-volume 100 order purification on normal-phase silica gel mixings stirrings, carry out the silica gel normal phase column chromatography.The chromatography stationary phase is 200-300 order purification on normal-phase silica gel, the high 1m of post, and diameter 15cm, eluent is for being respectively chloroform, chloroform: methyl alcohol=100:1-200:1,2,3 column volumes of wash-out respectively.And with gained elutriant difference called after Fr-1, Fr-2.With Fr-2 equal-volume silica gel mixed sample, using silica gel is 100 order purification on normal-phase silica gel, and pentaploid amasss silica gel column chromatography, and the silica gel of use is 200-300 order purification on normal-phase silica gel.Eluent is sherwood oil and acetone.The concentrating under reduced pressure elutriant uses methyl alcohol: chloroform=1:1 dissolving, chloroform methanol gel filtration chromatography.Using TLC to detect the elutriant of collecting suitably merges, evaporated under reduced pressure, reuse the purification on normal-phase silica gel chromatography, eluent is chloroform: methyl alcohol=100:1-50:1, collect elutriant, use TLC to detect each elutriant, merge and collect the elutriant that spot occurs, developping agent is sherwood oil: acetone=30:1-35:1.Drying under reduced pressure carries out 1D-
13CNMR nuclear magnetic resonance spectroscopy, frequency are 101 MHz, and δ 80.14,75.46,69.61,54.26,51.95,39.88,39.43,30.86,30.46,30.37,30.22,29.65,25.78,23.77,22.61 14.89,14.51. analytical results is the eudesmane type sesquiterpene that proves as new.
Example 2:
The Phellinus crude extract is made by following method:
(1) fermentative medium formula in gram/100 milliliter is:
W-Gum 3% glucose 2%
Peptone 0.5% yeast extract paste 0.5%
Sal epsom 0.5% potassium primary phosphate 0.05%
(2) the Phellinus bacterial classification is inoculated into ordinary method in the Erlenmeyer flask that liquid nutrient medium is housed, with 30 ℃ of temperature, the shaking flask rotating speed is 180r/min, and under the pH6 condition, vibrations were cultivated 15 days; In cultivation when the pH value drops to 2.5, seed in shaking flask is inoculated in the nutrient solution of 50L fermentor tank, with 30 ℃ of temperature, fermentor tank pressure 0.2 kg/cm, pH 3, air flow 0.5-1.1vvm, the condition that stirring velocity is 180 rev/mins, cultivated 15 days, and can utilize the phellinus igniarius mycelium fermentation liquid to prepare the Phellinus crude extract;
(3) get gained phellinus igniarius mycelium fermentation liquid in step (2), with its concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/5 of original volume;
(4) be that 90% the ethanol fermented liquid after concentrated to above-mentioned steps (3) extracts with volume percent, wherein, the amount that adds ethanol is 4 times of concentrated solution volume, can make that in extracting solution, alcohol concn reaches 70%;
(5) to step (4) gained extracting solution under 55 ℃ of conditions, heated 2.5 hours; Separate with ordinary method, and remove impurity by cascade filtration, separate obtaining ethanol extract; With above-mentioned ethanol extract concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/10 of original volume;
(6) just the concentrated solution of step (5) gained carries out drying with the method for frozen drying, gets the Phellinus crude extract.
Above-mentioned throw out is taken 200g and equal-volume 100 order purification on normal-phase silica gel mixings stirrings, carry out the silica gel normal phase column chromatography.The chromatography stationary phase is 200-300 order purification on normal-phase silica gel, the high 0.8m of post, and diameter 10cm, eluent is for being respectively chloroform, chloroform: methyl alcohol=100:1-200:1,2,3 column volumes of wash-out respectively.And with gained elutriant difference called after Fr-1, Fr-2.With Fr-2 equal-volume silica gel mixed sample, using silica gel is 100 order purification on normal-phase silica gel, and 3-4 times of volume silica gel column chromatography, the silica gel of use are 200-300 order purification on normal-phase silica gel.Eluent is sherwood oil and acetone.The concentrating under reduced pressure elutriant uses methyl alcohol: chloroform=1:1 dissolving, chloroform methanol gel filtration chromatography.Using TLC to detect the elutriant of collecting suitably merges, evaporated under reduced pressure, reuse the purification on normal-phase silica gel chromatography, eluent is chloroform: methyl alcohol=100:1-50:1, collect elutriant, use TLC to detect each elutriant, merge and collect the elutriant that spot occurs, developping agent is sherwood oil: acetone=30:1-35:1.Drying under reduced pressure carries out 1D-
13CNMR nuclear magnetic resonance spectroscopy, frequency are 101 MHz, and δ 80.14,75.46,69.61,54.26,51.95,39.88,39.43,30.86,30.46,30.37,30.22,29.65,25.78,23.77,22.61 14.89,14.51. analytical results is the eudesmane type sesquiterpene that proves as new.
Claims (9)
1. the separation method of new eudesmane type sesquiterpene in the Phellinus bacterium, its step order is as follows:
(1) preparation Phellinus crude extract;
(2) throw out and the purification on normal-phase silica gel mixing with step (1) gained stirs, and carries out the silica gel normal phase column chromatography after drying, uses the eluent wash-out 2-5 time, obtains elutriant;
(3) with last elutriant evaporate to dryness in step (2), the equal-volume silica gel mixed sample carries out the purification on normal-phase silica gel chromatography, uses the eluent wash-out;
(4) elutriant in collection step (3), concentrating under reduced pressure, use chloroform: methyl alcohol=1:1 dissolving, carry out the methanol gel column chromatography, use the eluent wash-out, the elutriant that uses the TLC detection to collect suitably merges elutriant, drying under reduced pressure;
(5) product that obtains in step (4) is carried out the purification on normal-phase silica gel chromatography again, use the eluent wash-out;
(6) collect the elutriant that step (5) obtains, use TLC to detect each elutriant, appropriateness merges elutriant, and drying under reduced pressure is 1,2-eudesmane type sesquiterpene.
As claimed in claim 1 a kind of from the Phellinus bacterium method of Separation of Benzene ethanol, it is characterized in that described Phellinus crude extract, made by following method:
(1) fermentative medium formula in gram/100 milliliter is:
W-Gum 1-5% glucose 1-5%
Peptone 0.1-0.5% yeast extract paste 0.1-0.5%
Sal epsom 0.1-0.5% potassium primary phosphate 0.01-0.05%
(2) fermentation culture method of Phellinus crude extract is as claimed in claim 1, the Phellinus bacterial classification is inoculated into ordinary method in the Erlenmeyer flask that liquid nutrient medium is housed, with 20～35 ℃ of temperature, the shaking flask rotating speed is 80～280r/min, under pH 3～8 conditions, vibrations were cultivated 7～15 days; In cultivation when the pH value drops to 2.5～4, seed in shaking flask is inoculated in the nutrient solution of 50L fermentor tank, with 20～35 ℃ of temperature, fermentor tank pressure 0.1～0.2 kg/cm, pH 3～8, air flow 0.5～1.1vvm, the condition that stirring velocity is 100～280 rev/mins, cultivated 7～15 days, and can utilize the phellinus igniarius mycelium fermentation liquid to prepare the Phellinus crude extract;
(3) get gained phellinus igniarius mycelium fermentation liquid in step (2), with its concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/2～1/5 of original volume;
(4) be that 60～95% the ethanol fermented liquid after concentrated to above-mentioned steps (3) extracts with volume percent, wherein, the amount that adds ethanol is 2～5 times of concentrated solution volume, can make that in extracting solution, alcohol concn reaches 60～90%;
(5) to step (4) gained extracting solution under 50～70 ℃ of conditions, heated 1～2 hour; Separate with ordinary method, and remove impurity by cascade filtration, separate obtaining ethanol extract; With above-mentioned ethanol extract concentrating under reduced pressure in a usual manner, make its volume be concentrated to 1/5～1/10 of original volume;
(6) just the concentrated solution of step (5) gained carries out drying with the method for frozen drying, gets the Phellinus crude extract;
The separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1 is characterized in that described eudesmane type sesquiterpene is 1,2-eudesmane type sesquiterpene.
3. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the sample silica gel of mixing described in step (2) is 100-200 order purification on normal-phase silica gel.
4. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the chromatographic silica gel described in step (2) is positive 200-300 order, and eluent is chloroform and/or methyl alcohol.
5. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the silica gel consumption described in step (3) is equal-volume, and eluent is sherwood oil and acetone.
6. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the gel described in step (4) is Sephadex LH-20, and eluent is chloroform: methyl alcohol=1:1.
7. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the described chromatographic silica gel of step (5) is the 200-300 order.
8. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the described eluent of step (5) is chloroform: methyl alcohol=100:1-50:1.
9. the separation method of new eudesmane type sesquiterpene in Phellinus bacterium as claimed in claim 1, is characterized in that, the described detection point of step (6) is spot to occur, and developping agent is sherwood oil: acetone=30:1-35:1.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111388512A (en) * | 2020-03-24 | 2020-07-10 | 江西康之康中药科技有限公司 | Extraction method of active ingredients of phellinus igniarius and phellinus igniarius traditional Chinese medicine decoction pieces |
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| CN101182550A (en) * | 2007-11-16 | 2008-05-21 | 上海市农业科学院 | Flavonoids from phellinus, method of producing the same and use |
| CN101297821A (en) * | 2007-09-18 | 2008-11-05 | 江苏大学 | Phellinus linteus mycelia active glucoprotein and use thereof and preparation |
| CN101323648A (en) * | 2008-07-29 | 2008-12-17 | 上海璞诚生物科技有限公司 | Extraction method and and purification method of Sanghuang mushroom polysaccharide |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101032532A (en) * | 2007-04-28 | 2007-09-12 | 北京鸿华新康生物技术有限公司 | Medicine composition including active substrates extracted from Sang Huang, the preparing method and the application in the producing of medicine thereof |
| CN101297821A (en) * | 2007-09-18 | 2008-11-05 | 江苏大学 | Phellinus linteus mycelia active glucoprotein and use thereof and preparation |
| CN101182550A (en) * | 2007-11-16 | 2008-05-21 | 上海市农业科学院 | Flavonoids from phellinus, method of producing the same and use |
| CN101323648A (en) * | 2008-07-29 | 2008-12-17 | 上海璞诚生物科技有限公司 | Extraction method and and purification method of Sanghuang mushroom polysaccharide |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111388512A (en) * | 2020-03-24 | 2020-07-10 | 江西康之康中药科技有限公司 | Extraction method of active ingredients of phellinus igniarius and phellinus igniarius traditional Chinese medicine decoction pieces |
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Application publication date: 20130522 |