CN103044228A - Technology for separating acetophenone from Phellinus - Google Patents
Technology for separating acetophenone from Phellinus Download PDFInfo
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- CN103044228A CN103044228A CN2012105460604A CN201210546060A CN103044228A CN 103044228 A CN103044228 A CN 103044228A CN 2012105460604 A CN2012105460604 A CN 2012105460604A CN 201210546060 A CN201210546060 A CN 201210546060A CN 103044228 A CN103044228 A CN 103044228A
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Abstract
The invention discloses a technology for separating acetophenone from Phellinus (Phellinusigniarius (LexFr) Quel, Phellinuslinteus (BerketCurt) Teng, Phellinus baumii and Phellinushartigii (AlleschetSchnabl) Imaz). The technology comprises the following steps of: firstly, preparing a crude Phellinus extract; secondly, performing normal phase silica gel chromatography, performing gradient elution by using chloroform and methanol, and performing TLC (thin-layer chromatography) detection on eluent; thirdly, performing methanol gel chromatography, and performing TLC detection again; fourthly, performing reverse phase silica gel chromatography; and finally, after the TLC detection, drying a product by distillation under reduced pressure to obtain colorless oil acetophenone.
Description
Technical field
The invention belongs to the biotech medicine product field.
Background technology
Phellinus, 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, always often be full of cracks is without cot; there is trickle fine hair at initial stage, and rear change has the concentric ring rib without hair. and the edge is blunt; dark cinnamon is to light coffee color, and downside is without thalamium. and the bacterial context dark brown is hard; wooden. tube and bacterial context are closely homochromy, multilayer, but level is not obvious; old tube layer is full of white hypha. and the mouth of pipe becomes rusty brown to dark reddish brown, circle, every millimeter 4-5. and 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) a kind of isolation technique of methyl phenyl ketone in.At first prepare the Phellinus crude extract; then carry out the purification on normal-phase silica gel chromatography with chloroform and methyl alcohol gradient elution; use TLC to detect elutriant; then carry out the methanol gel chromatography; again carrying out TLC detects; then use reversed-phase silica gel chromatography, detect through TLC, it is a kind of methyl phenyl ketone that the product evaporated under reduced pressure is both got colorless oil.
Technical scheme of the present invention is as follows:
The Phellinus crude extract is made by following method:
(1) fermentative medium formula in/100 milliliters of grams 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 the cultivation when the pH value drops to 2.5～4, seed in the 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 the 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 alcohol concn reaches 60～90% in the extracting solution;
(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.
Phellinus bacterium crude extract → ethanol precipitation → purification on normal-phase silica gel chromatography → chloroform and methyl alcohol gradient elution → TLC detection → methanol gel chromatography → TLC detection → reversed-phase silica gel chromatography → TLC detection → evaporated under reduced pressure → colorless oil (a kind of methyl phenyl ketone).
Concrete grammar is:
(1) preparation Phellinus bacterium crude extract;
(2) crude extract and the purification on normal-phase silica gel mixing with above-mentioned steps (1) gained stirs, and places the dry also stirring in ventilation installation place;
(3) the silica gel normal phase column chromatography is carried out in the raw material of preparation after the above-mentioned steps (2), use the eluent wash-out 2 to 5 times, obtain elutriant;
(4) with the last elutriant equal-volume silica gel mixed sample in the step (3), carry out silica gel column chromatography, use the eluent wash-out;
(5) elutriant of collection step (4), concentrating under reduced pressure uses dissolve with methanol, carries out the methanol gel column chromatography, uses the eluent wash-out, uses TLC to detect the elutriant of collection, suitably merges elutriant, drying under reduced pressure;
(6) product that step (5) is obtained carries out the normal pressure reversed phase column chromatography, uses the eluent wash-out;
(7) collect the elutriant that step (6) obtains, use TLC to detect each elutriant, appropriateness merges elutriant, and drying under reduced pressure is methyl phenyl ketone.
Significant advantage of the present invention: present method adopts multiple chromatographic technique to combine, can be exquisite clear and definite to structure, and purity is greater than a kind of methyl phenyl ketone of 95%.Mature technical route is clear and definite, and is accurately efficient.
(4) description of drawings
Fig. 1 is 3', the structural formula of 4'-resacetophenone;
Fig. 2 is 3', the one-dimensional nuclear magnetic resonance H spectrum of 4'-resacetophenone.
(5) embodiment
Example 1:
The Phellinus crude extract is made by following method:
(1) fermentative medium formula in/100 milliliters of grams 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 the cultivation when the pH value drops to 3, seed in the 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 the 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 alcohol concn reaches 55% in the extracting solution;
(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.
Above-mentioned Phellinus crude extract is taken by weighing 300g and the stirring of equal-volume 100 order purification on normal-phase silica gel mixings, and then dry and stirring carries out the silica gel normal phase column chromatography as for the ventilation installation place.The chromatography stationary phase is 200-300 order purification on normal-phase silica gel, the high 1m of post, and diameter 20cm, eluent is for being respectively chloroform, chloroform: methyl alcohol=100:1, chloroform: methyl alcohol=500:1, every kind of eluent elution volume of chloroform: methyl alcohol=100:1. is respectively 2,3,3,3 column volumes.And with gained elutriant difference called after Fr-1, Fr-2, Fr-3, Fr-4.With Fr-4 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 order purification on normal-phase silica gel.Eluent is chloroform.Collect above-mentioned elutriant, concentrating under reduced pressure uses dissolve with methanol, the methanol gel column chromatography.Use TLC to detect the elutriant of collecting, merge and collect the elutriant that punctation occurs, evaporated under reduced pressure is used the above-mentioned product of 20% dissolve with methanol, carries out the normal pressure reversed phase column chromatography, and eluent is 20%-100% methyl alcohol.Collect elutriant, use TLC to detect each elutriant, merge and collect the elutriant that punctation occurs.Drying under reduced pressure carries out the 1D-HNMR nuclear magnetic resonance spectroscopy, and frequency is 400MHZ, analytical results is δ 7.43 (d, J=8.6 Hz, 19H), 6.81 (d, J=7.9 Hz, 10H), 2.49 (s, 27H), (2.42 s, 2H). illustrate that it is 3 ', 4 '-resacetophenone.
Example 2:
The Phellinus crude extract is made by following method:
(1) fermentative medium formula in/100 milliliters of grams 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 the cultivation when the pH value drops to 2.5, seed in the 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 the 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 alcohol concn reaches 70% in the extracting solution;
(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.
Take by weighing crude extract 100g and equal-volume 100 order purification on normal-phase silica gel mixings and stir, then dry and stirring carries out the silica gel normal phase column chromatography as for the ventilation installation place.The chromatography stationary phase is 200-300 order purification on normal-phase silica gel, the high 0.5m of post, and diameter 5cm, eluent is for being respectively chloroform: methyl alcohol=100:1, chloroform: methyl alcohol=500:1, every kind of eluent elution volume of chloroform: methyl alcohol=100:1. is respectively 3,3,3 column volumes.And with gained elutriant difference called after Fr-1, Fr-2, Fr-3.With Fr-3 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 chloroform.Collect above-mentioned elutriant, concentrating under reduced pressure uses dissolve with methanol, the methanol gel column chromatography.Use TLC to detect the elutriant of collecting, merge and collect the elutriant that punctation occurs, evaporated under reduced pressure is used the above-mentioned product of 20% dissolve with methanol, carries out the normal pressure reversed phase column chromatography, and eluent is 20%-100% methyl alcohol.Collect elutriant, use TLC to detect each elutriant, merge and collect the elutriant that punctation occurs.Drying under reduced pressure carries out the 1D-HNMR nuclear magnetic resonance spectroscopy, and frequency is 400MHZ, analytical results is δ 7.43 (d, J=8.6 Hz, 19H), 6.81 (d, J=7.9 Hz, 10H), 2.49 (s, 27H), (2.42 s, 2H). illustrate that it is 3 ', 4 '-resacetophenone.
Claims (9)
1. separation of benzene ethyl ketone method from the Phellinus bacterium, its step order is as follows:
(1) preparation Phellinus crude extract;
(2) crude extract and the purification on normal-phase silica gel mixing with above-mentioned steps (1) gained stirs, and places the dry also stirring in ventilation installation place;
(3) the silica gel normal phase column chromatography is carried out in the raw material of preparation after the above-mentioned steps (2), use the eluent wash-out 2 to 5 times, obtain elutriant;
(4) with the last elutriant equal-volume silica gel mixed sample in the step (3), carry out silica gel column chromatography, use the eluent wash-out;
(5) elutriant of collection step (4), concentrating under reduced pressure uses dissolve with methanol, carries out the methanol gel column chromatography, uses the eluent wash-out, uses TLC to detect the elutriant of collection, suitably merges elutriant, drying under reduced pressure;
(6) product that step (5) is obtained carries out the normal pressure reversed phase column chromatography, uses the eluent wash-out;
(7) collect the elutriant that step (6) obtains, use TLC to detect each elutriant, appropriateness merges elutriant, and drying under reduced pressure is methyl phenyl ketone.
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/100 milliliters of grams 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, and 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 the cultivation when the pH value drops to 2.5～4, seed in the 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 the 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 alcohol concn reaches 60～90% in the extracting solution;
(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.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that described alcohol concn is the 65%-95% edible ethanol, used volume is 3-6 times of volume.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that, the silica gel described in the step (2) is 100-200 order purification on normal-phase silica gel.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that, the silica gel described in the step (3) is positive 200-300 order, eluent is chloroform and/or methyl alcohol.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that, the silica gel consumption described in the step (4) is 1-3 times of volume, eluent is chloroform.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that, the gel described in the step (5) is Sephadex LH-20, eluent is methyl alcohol or acetone.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that, the described reverse phase silica gel of step (6) is anti-phase C-8, C-18, eluent is methyl alcohol.
As claimed in claim 1 a kind of from the Phellinus bacterium method of separation of benzene ethanol, it is characterized in that, the TLC detection point is punctation to occur in the step (7), developping agent is chloroform: methyl alcohol=30:1-40:1.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0181105B1 (en) * | 1996-11-25 | 1999-10-01 | 이능희 | Cosmetic composition containing extracts from phellinus sp. |
| KR20030026613A (en) * | 2001-09-26 | 2003-04-03 | 강경선 | Composition for preventing or treating gap junctional intercellular communication and homeostasis-related diseases comprising phellinus linteus extract |
| CN101348803A (en) * | 2008-09-03 | 2009-01-21 | 西南大学 | Artificial nutrient medium for Phellinus linteus fluid culture and method for fermentation of Phellinus linteus polysaccharide |
-
2012
- 2012-12-15 CN CN2012105460604A patent/CN103044228A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0181105B1 (en) * | 1996-11-25 | 1999-10-01 | 이능희 | Cosmetic composition containing extracts from phellinus sp. |
| KR20030026613A (en) * | 2001-09-26 | 2003-04-03 | 강경선 | Composition for preventing or treating gap junctional intercellular communication and homeostasis-related diseases comprising phellinus linteus extract |
| CN101348803A (en) * | 2008-09-03 | 2009-01-21 | 西南大学 | Artificial nutrient medium for Phellinus linteus fluid culture and method for fermentation of Phellinus linteus polysaccharide |
Non-Patent Citations (2)
| Title |
|---|
| 谢丽源等: "桑黄真菌优势菌株筛选研究", 《西南农业学报》, vol. 24, no. 5, 31 December 2011 (2011-12-31), pages 1766 - 1700 * |
| 陈柳萌等: "桑黄菌的研究进展", 《江西农业学报》, vol. 19, no. 5, 31 December 2007 (2007-12-31), pages 88 - 90 * |
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Application publication date: 20130417 |