CN1839892B - Preparation method of yeast W.domercqiaeY2A variation waufa glucolipid crude extract with antineoplastic activity - Google Patents
Preparation method of yeast W.domercqiaeY2A variation waufa glucolipid crude extract with antineoplastic activity Download PDFInfo
- Publication number
- CN1839892B CN1839892B CN200610042181A CN200610042181A CN1839892B CN 1839892 B CN1839892 B CN 1839892B CN 200610042181 A CN200610042181 A CN 200610042181A CN 200610042181 A CN200610042181 A CN 200610042181A CN 1839892 B CN1839892 B CN 1839892B
- Authority
- CN
- China
- Prior art keywords
- sophorolipid
- crude extract
- preparation
- wickerhamiella domercqiae
- domercqiae var
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Landscapes
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a process for preparing Wickerhamiella domercqiae var. sophorolipid antineoplastic sophorolipid crude extract, which comprises the following steps: subjecting Wickerhamiella domercqiae var. sophorolipid fermentation liquor to natural sedimentation, acetic acid ethyl ester extraction, filtering, scrubbing, vacuum distilling, drying the gathered substance and preparing alcoholic solution of sophorolipid.
Description
Technical field
The present invention relates to the process for extracting of the outer anti-tumor active substance of yeast mycetocyte, relate in particular to the preparation method of Wickerhamiella domercqiae var. sophorolipid (Wickerhamiella domercqiae var.sophorolipid) anti-tumor activity sophorolipid crude extract.
Background technology
Sophorolipid is a kind of important bio-surfactant, starts from twentieth century five, the sixties for its research, mainly is to obtain through microbial fermentation.Compare with the tensio-active agent of chemosynthesis, have many advantages such as surface property is good, environmental friendliness.
In recent years, for the research of sophorolipid as medicine, particularly antitumor drug aspect some bibliographical informations have been arranged also abroad.People such as Scholz and Mehta. report; Bullion sophorolipid and sophorolipid verivate can suppress the propagation of human leukemic HL60 and people's neck cancer cells; And the anti-tumor activity that has proved sophorolipid is relevant with the ethanoyl of sophorolipid; Remove the ethanoyl of sophorolipid through chemical reaction, find that its anti-tumor activity obviously reduces, but to the not further research of its antitumor mechanism.People such as Isoda report, sophorolipid can cause the cytodifferentiation of HL60 leukemia cell system and the activity of arrestin kinase c.In addition, sophorolipid can be used as the immunomodulator of parkinson's disease, senile dementia, psoriasis, treating AIDS, also can be used as antiviral immunostimulation.
The bacterial strain that is used at present the fermentative prodn sophorolipid in the world is confined to several saccharomycetes of U.S. typical case DSMZ, and China has the product sophorolipid bacterial strain of independent intellectual property right that report was not arranged in 2005 in the past.
According to document and patent retrieval, the research that utilizes microorganisms sophorolipid bio-surfactant to be used to suppress Bel7402 and lung cancer cell line does not appear in the newspapers.Therefore, preparing the Wickerhamiella domercqiae var. sophorolipid sophorolipid crude extract and studying it is the propagation of A549 as antitumor drug inhibition Bel7402 H7402 and lung adenocarcinoma cell, promotes its apoptotic mechanism of action and practical application aspect to have significant values.
Summary of the invention
The problem that the present invention will solve is; To the preparation method of above-mentioned Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract with and the existing deficiency of pharmacological action of the active substance extract of preparation, a kind of preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract is provided.
The plan Brunswick yeast sophorolipid crude extract that utilizes method of the present invention to extract is that A549 handled 24 hours to Bel7402 H7402 and lung adenocarcinoma cell; It is suppressed fully; And normal cell is not had undesirable action, and this method has the advantages that technology is easy, cost is low.
The preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract of the present invention, its preparation form: directly from Wickerhamiella domercqiae var. sophorolipid comprises the fermentation liquid of thalline, isolate the anti-tumor activity sophorolipid crude extract;
The preparation method of above-mentioned Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract is made up of following steps:
(1) natural subsidence: the Wickerhamiella domercqiae var. sophorolipid of the liquid fermenting of learning from else's experience (Wickerhamiella domercqiae var.sophorolipid) CGMCC No.1576 fermentation liquid, left standstill 1～6 hour, natural subsidence is collected the light yellow thick substances in the fermented liquid.With 4000～6000 rev/mins that above-mentioned thick substances is centrifugal afterwards, collect solid-state part;
(2) ethyl acetate extraction: with above-mentioned its volume that in the centrifugal throw out that obtains, adds is 3～10 times ETHYLE ACETATE, under 25～37 ℃, extracts 2～8 hours.
(3) filter: above-mentioned acetic acid ethyl acetate extract under 25～37 ℃, with Whatman No.2 filter paper filtering, is collected filter residue.
(4) washing: filter residue that above-mentioned steps (3) obtains use its volume be 3～10 times ETHYLE ACETATE under 25～37 ℃, wash 2～4 times.
(5) underpressure distillation: collect filter residue after washing finishes, at 50～70 ℃ of temperature, pressure 0.2～0.8Kg/cm
2, vacuum tightness is to carry out underpressure distillation under the condition of 0.02～0.08Mpa, with the ETHYLE ACETATE evaporative removal in the filtrating;
(6) gleanings is dry: with the underpressure distillation residue of above-mentioned collection, at 50～100 ℃, under vacuum tightness 0.02～0.08Mpa condition, vacuum-drying 12～24 hours makes the solid sophorolipid crude extract;
(7) sophorolipid ethanolic soln preparation: it is that 20～100 μ g/mL sophorolipid ethanolic solns are used for external inhibition test that the sophorolipid solid that above-mentioned steps (6) is obtained is made into concentration.
The described Wickerhamiella domercqiae var. sophorolipid fermentation liquid of above-mentioned steps (1) be meant Wickerhamiella domercqiae var. sophorolipid (Wickerhamiella domercqiae var.sophorolipid) through the fermentation obtain comprise thalline fermentation liquid.
Wherein, the described fermentation liquid time of repose of step (1) preferably 4～6 hours, preferably 4000～5000 rev/mins of centrifuge speeds.
Wherein, 4～6 times of the filter residue volume that the described ETHYLE ACETATE add-on of step (2) preferably obtains, the extraction time is preferably 3～4 hours.
Wherein, step (2), (3), preferably 28～32 ℃ of (4) said temperature.
Wherein, 4～6 times of the filter residue volume that the described washing of step (4) preferably obtains with the ETHYLE ACETATE volume, washing times is preferably 2～3 times.
Wherein, the described underpressure distillation condition of step (5) is: preferably 60～70 ℃ of temperature, pressure is 0.5～0.6Kg/cm preferably
2, vacuum tightness is 0.04～0.06Mpa preferably.
Wherein, the vacuum drying condition optimization of the described gleanings of step (6) is: 0.04～0.06Mpa, preferably 50～70 ℃ of temperature, preferably 12～16 hours time.
Wherein, the described sophorolipid ethanolic soln concentration that is used for external inhibition test of step (7) 30～50 μ g/mL preferably.
The bacterial strain Wickerhamiella domercqiae var. sophorolipid Wickerhamiella domercqiae var.sophorolipid that the present invention relates to; Be preserved in China Committee for Culture Collection of Microorganisms common micro-organisms center on December 26th, 2005; Preservation address: No. 13, North No.1 Row, Zhongguancun, Haidian District, Beijing City; Postcode: 100080, its deposit number is CGMCC No.1576.
Adopt the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract of the present invention, have the advantages that technology is easy, output is high, cost is low.This method adopts the fermentation liquid of Wickerhamiella domercqiae var. sophorolipid directly to carry out the sophorolipid active substance and extracts, and fermentation raw material is cheap, has reduced production cost, has improved productive rate.
The sophorolipid crude extract that adopts method of the present invention to extract; Through external inhibition test; The result shows: the sophorolipid of very low dose is that the inhibiting rate of A549 can reach more than 85% in short action time (＜24 hours) to Bel7402 H7402 and lung adenocarcinoma cell; Can suppress the propagation of tumour cell fully in that the concentration of 125 μ g/L is next, and normal cell is not had undesirable action.
The concrete grammar of the sophorolipid antitumor activity in vitro of doing is following:
I, experiment material
1. cell
(1) tumour cell: Bel7402 H7402, attached cell;
Lung adenocarcinoma cell is A549, attached cell;
(2) normal cell: liver cell HL-7702 and Chang liver
2. nutrient solution: RPMI 1640 perfect mediums that contain 10% foetal calf serum
II, experiment condition
Three grades of laboratories of Biosafety
III, experimental procedure
1. the IC50 of above-mentioned two strain tumour cells measures under the sophorolipid effect;
2.CPE method combines mtt assay to confirm the non-toxic concn of medicine pair cell;
3. the maximal non-toxic concentration of medicine is to the evaluation of pesticide effectiveness of above-mentioned two strain tumour cells;
IV, experimental result
1. sophorolipid is 32.05ug/ml to the IC50 of Bel7402 H7402, is that the IC50 of A549 is 20.52ug/ml to lung adenocarcinoma cell.
Medicine get 6 concentration promptly 1000,500,250,125,62.5,30ug/ml, after the degerming of 0.22um membrane filtration, carry out CTA, every concentration is done 4 multiple holes, establishes the cell contrast simultaneously.The result shows that maximal non-toxic concentration is 125ug/ml.
3. get the 125ug/ml soup, do 4 multiple holes, observe restraining effect above-mentioned two strain tumour cells.The normal cell contrast is established in test.The result shows that this concentration medicine has complete restraining effect to above-mentioned two strain tumour cells.
Below in conjunction with embodiment the present invention is further described.
Embodiment
Embodiment 1: the preparation of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract
(1) natural subsidence: the Wickerhamiella domercqiae var. sophorolipid of the liquid fermenting of learning from else's experience (Wickerhamiella domercqiae var.sophorolipid) CGMCC No.1576 fermentation liquid, left standstill 2 hours, natural subsidence is collected the light yellow thick substances in the fermented liquid.With 4000 rev/mins that above-mentioned thick substances is centrifugal afterwards, collect solid-state part;
(2) ethyl acetate extraction: in the centrifugal throw out that obtains, to add volume be the ETHYLE ACETATE of 300mL with above-mentioned, under 25 ℃, extracted 2 hours.
(3) filter: above-mentioned acetic acid ethyl acetate extract under 25 ℃, with Whatman No.2 filter paper filtering, is collected filter residue.
(4) washing: the filter residue that above-mentioned steps (3) obtains use volume as 300mL ETHYLE ACETATE under 25 ℃, wash 2 times.
(5) underpressure distillation: collect filter residue after washing finishes, at 50 ℃ of temperature, pressure 0.2kg/cm
2, vacuum tightness is to carry out underpressure distillation under the condition of 0.02Mpa, with the ETHYLE ACETATE evaporative removal in the filtrating;
(6) gleanings is dry: with the underpressure distillation residue of above-mentioned collection, and at 50 ℃, under the vacuum tightness 0.02Mpa condition, vacuum-drying 12 hours;
(7) sophorolipid ethanolic soln preparation: it is that 20 μ g/mL sophorolipid ethanolic solns are used for external inhibition test that the sophorolipid solid that above-mentioned steps (6) is obtained is made into concentration.
Embodiment 2: the preparation of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract
(1) natural subsidence: the Wickerhamiella domercqiae var. sophorolipid of the liquid fermenting of learning from else's experience (Wickerhamiella domercqiae var.sophorolipid) CGMCC No.1576 fermentation liquid, left standstill 4 hours, natural subsidence is collected the light yellow thick substances in the fermented liquid.With 5000 rev/mins that above-mentioned thick substances is centrifugal afterwards, collect solid-state part;
(2) ethyl acetate extraction: in the centrifugal throw out that obtains, to add volume be the ETHYLE ACETATE of 300mL with above-mentioned, under 30 ℃, extracted 4 hours.
(3) filter: above-mentioned acetic acid ethyl acetate extract under 30 ℃, is used the WhatmanNo.2 filter paper filtering, collect filter residue.
(4) washing: the filter residue that above-mentioned steps (3) obtains use volume as 500mL ETHYLE ACETATE under 30 ℃, wash 3 times.
(5) underpressure distillation: collect filter residue after washing finishes, at 70 ℃ of temperature, pressure 0.4kg/cm
2, vacuum tightness is to carry out underpressure distillation under the condition of 0.04Mpa, with the ETHYLE ACETATE evaporative removal in the filtrating;
(6) gleanings is dry: with the underpressure distillation residue of above-mentioned collection, and at 70 ℃, under the vacuum tightness 0.04Mpa condition, vacuum-drying 16 hours;
(7) sophorolipid ethanolic soln preparation: it is that 50 μ g/mL sophorolipid ethanolic solns are used for external inhibition test that the sophorolipid solid that above-mentioned steps (6) is obtained is made into concentration.
Embodiment 3: the preparation of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract
(1) natural subsidence: the Wickerhamiella domercqiae var. sophorolipid of the liquid fermenting of learning from else's experience (Wickerhamiella domercqiae var.sophorolipid) CGMCC No.1576 fermentation liquid, left standstill 2 hours, natural subsidence is collected the light yellow thick substances in the fermented liquid.With 6000 rev/mins that above-mentioned thick substances is centrifugal afterwards, collect solid-state part;
(2) ethyl acetate extraction: in the centrifugal throw out that obtains, to add volume be the ETHYLE ACETATE of 600mL with above-mentioned, under 37 ℃, extracted 6 hours.
(3) filter: above-mentioned acetic acid ethyl acetate extract under 37 ℃, with Whatman No.2 filter paper filtering, is collected filter residue.
(4) washing: the filter residue that above-mentioned steps (3) obtains use volume as 600mL ETHYLE ACETATE under 37 ℃, wash 3 times.
(5) underpressure distillation: collect filter residue after washing finishes, at 70 ℃ of temperature, pressure 0.8kg/cm
2, vacuum tightness is to carry out underpressure distillation under the condition of 0.08Mpa, with the ETHYLE ACETATE evaporative removal in the filtrating;
(6) gleanings is dry: with the underpressure distillation residue of above-mentioned collection, and at 100 ℃, under the vacuum tightness 0.08Mpa condition, vacuum-drying 24 hours;
(7) sophorolipid ethanolic soln preparation: it is that 100 μ g/mL sophorolipid ethanolic solns are used for external inhibition test that the sophorolipid solid that above-mentioned steps (6) is obtained is made into concentration.、
Embodiment 4:
Adopt the Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract of the method extraction of embodiment 1; With human liver cancer cell H7402 and human lung adenocarcinoma cell, the RPMI1640 perfect medium that contains 10% foetal calf serum is experiment material, measures sophorolipid to two strain tumour cell median lethal concentration (IC
50), the CPE method combines mtt assay to confirm the experimental techniques such as the evaluation of pesticide effectiveness of the maximal non-toxic concentration of the non-toxic concn of medicine pair cell, medicine to human liver cancer cell H7402 and human lung adenocarcinoma cell, carries out the test of sophorolipid antitumor activity in vitro, experimental result is following:
1. sophorolipid is 32.05ug/ml to the IC50 of Bel7402 H7402, is that the IC50 of A549 is 20.52ug/ml to lung adenocarcinoma cell.
Medicine get 6 concentration promptly 1000,500,250,125,62.5,31.25ug/ml carries out CTA, every concentration is done 4 multiple holes, establishes the cell contrast simultaneously.The result shows that maximal non-toxic concentration is 125ug/ml.
3. get the 125ug/ml soup, do 4 multiple holes, observe restraining effect human liver cancer cell H7402 and human lung adenocarcinoma cell.Tumour cell contrast and the contrast of people's normal cell lines of human liver are established in test.The result shows that this concentration medicine has complete restraining effect to two strain tumour cells, does not have undesirable action to normal cell.
Embodiment 5:
1. collecting cell: 5 times the centrifugal 10min of tumour cell 1000r/min that is in logarithmic phase of will going down to posterity, abandon supernatant, be diluted to cell suspension with the RPMI1640 perfect medium, counting, the concentration of H7402 and A549 is respectively 2.5 * 10
5Cells/ml and A549 are 3.5 * 10
5Cells/ml.
2. add sample and cell: in 96 well culture plates, add 50ul sophorolipid ethanolic soln; Under the aseptic condition ethanol is volatilized fully; Add the 100ul cell suspension then; 3 multiple holes of every group of sample, and establish solvent control group (the 50ul absolute ethyl alcohol also volatilizees and cell fully), cell control group (only adding cell) and blank group (only adding substratum, acellular).
3. put 37 ℃, 5%CO
2Cultivate 48h in the incubator.
4. observe with inverted microscope.
The result shows that active with A549 cell proliferation and visible each the phase division of normal H7402 cell is arranged between the cell closely mutually; Form is irregular polygon or circle, and clear-cut is examined rounded or oval; And visible multinuclear and giant nuclear cells, the irregular about 2-4 of kernel.
H7402 cell after the sophorolipid effect, the part cell shrinkage becomes circle, volume-diminished, cell surface projection microsphere, the likeness in form yeast sprouts, and kernel disappears, and it is thus clear that microsphere and fragment are suspended in the nutrient solution.The A549 cell is also observed similar results.
Claims (8)
1. the preparation method of a Wickerhamiella domercqiae var. sophorolipid (Wickerhamiella domercqiae var.sophorolipid) anti-tumor activity sophorolipid crude extract, the preparation form is: directly from the Wickerhamiella domercqiae var. sophorolipid fermentation liquid, isolate the anti-tumor activity sophorolipid crude extract;
The preparation method of above-mentioned Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract is made up of following steps:
(1) natural subsidence: the Wickerhamiella domercqiae var. sophorolipid of the liquid fermenting of learning from else's experience (Wickerhamiella domercqiae var.sophorolipid) CGMCC No.1576 fermentation liquid; Left standstill 1 ~ 6 hour; Natural subsidence is collected the light yellow thick substances in the fermented liquid; With 4000～7000 rev/mins that above-mentioned thick substances is centrifugal afterwards, the collecting precipitation part;
(2) ethyl acetate extraction: with above-mentioned its volume that in the centrifugal throw out that obtains, adds is 3 ~ 10 times ETHYLE ACETATE, under 25 ~ 37 ℃, extracts 2 ~ 8 hours;
(3) filter: above-mentioned acetic acid ethyl acetate extract under 25 ~ 37 ℃, with Whatman No.2 filter paper filtering, is collected filter residue;
(4) washing: filter residue that above-mentioned steps (3) obtains use its volume be 3 ~ 10 times ETHYLE ACETATE under 25 ~ 37 ℃, wash 2 ~ 4 times;
(5) underpressure distillation: collect filter residue after washing finishes, at 50～70 ℃ of temperature, pressure 0.2～0.8Kg/cm
2, vacuum tightness is to carry out underpressure distillation under the condition of 0.02～0.08Mpa, with the ETHYLE ACETATE evaporative removal in the filtrating;
(6) gleanings is dry: with the underpressure distillation residue of above-mentioned collection, at 50～100 ℃, under vacuum tightness 0.02～0.08Mpa condition, vacuum-drying 12～24 hours makes the solid sophorolipid crude extract.
2. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1; It is characterized in that the described Wickerhamiella domercqiae var. sophorolipid fermentation liquid of step (1) is meant the fermentation liquid that comprises thalline that Wickerhamiella domercqiae var. sophorolipid (Wickerhamiella domercqiae var. sophorolipid) obtains through fermentation.
3. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1 is characterized in that, the described fermentation liquid time of repose of step (1) is 4 ~ 6 hours, and centrifuge speed is 4000～5000 rev/mins.
4. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1 is characterized in that, the described ETHYLE ACETATE add-on of step (2) is 4 ~ 6 times of the filter residue volume that obtains, and the extraction time is 3 ~ 4 hours.
5. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1 is characterized in that, step (2), (3), (4) said temperature is 28 ~ 32 ℃.
6. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1 is characterized in that, the described washing of step (4) is 4 ~ 6 times of the filter residue volume that obtains with the ETHYLE ACETATE volume, and washing times is 2 ~ 3 times.
7. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1 is characterized in that, the described underpressure distillation condition of step (5) is: 60～70 ℃ of temperature, pressure 0.5 ~ 0.6Kg/cm
2, vacuum tightness is 0.04～0.06Mpa.
8. the preparation method of Wickerhamiella domercqiae var. sophorolipid anti-tumor activity sophorolipid crude extract as claimed in claim 1; It is characterized in that; The vacuum drying condition of the described gleanings of step (6) is: vacuum tightness 0.04～0.06Mpa, 50～70 ℃ of temperature, 12～16 hours time.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200610042181A CN1839892B (en) | 2006-01-13 | 2006-01-13 | Preparation method of yeast W.domercqiaeY2A variation waufa glucolipid crude extract with antineoplastic activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200610042181A CN1839892B (en) | 2006-01-13 | 2006-01-13 | Preparation method of yeast W.domercqiaeY2A variation waufa glucolipid crude extract with antineoplastic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1839892A CN1839892A (en) | 2006-10-04 |
| CN1839892B true CN1839892B (en) | 2012-09-19 |
Family
ID=37029194
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200610042181A Expired - Fee Related CN1839892B (en) | 2006-01-13 | 2006-01-13 | Preparation method of yeast W.domercqiaeY2A variation waufa glucolipid crude extract with antineoplastic activity |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1839892B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101703514B (en) * | 2009-11-23 | 2011-05-11 | 山东大学 | Application of sophorolipids in preparation of medicament for resisting cervical cancer |
| CN102492753B (en) * | 2011-12-07 | 2013-05-29 | 山东大学 | Method for producing sophorolipid through fermentation of lignocellulose material |
| CN103275140B (en) * | 2013-06-17 | 2016-05-25 | 山东大学 | The two key lactone type sophorolipids of 18 one of carbon diacetyl and application thereof |
| CN103275139B (en) * | 2013-06-17 | 2015-12-23 | 山东大学 | 16 carbon diacetyl one double bond lactone type sophorolipid and application thereof |
| CN103540631B (en) * | 2013-10-22 | 2015-04-22 | 山东大学 | Method for producing sophorolipid through fermentation by taking cottonseed molasses and cottonseed oil as substrates |
| CN105191941B (en) * | 2015-08-26 | 2017-07-21 | 中国农业科学院蔬菜花卉研究所 | Microbicide solution and its application containing sophorolipid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5767255A (en) * | 1995-05-29 | 1998-06-16 | Hoechst Aktiengesellschaft | Glucose- and sophorose-lipids, a process for their preparation and their use |
| CN1232036A (en) * | 1999-02-10 | 1999-10-20 | 中国科学院上海有机化学研究所 | Production of sucrose ester by homogeneous solventless process |
| US6379937B1 (en) * | 2000-12-18 | 2002-04-30 | Council Of Scientific And Industrial Research | Process for the preparation of a mixture of 19 hydroxyelcosatetraenoic acid and 20 hydroxyeicosatetracnoic acid (10 hete and 20 hete) |
-
2006
- 2006-01-13 CN CN200610042181A patent/CN1839892B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5767255A (en) * | 1995-05-29 | 1998-06-16 | Hoechst Aktiengesellschaft | Glucose- and sophorose-lipids, a process for their preparation and their use |
| CN1232036A (en) * | 1999-02-10 | 1999-10-20 | 中国科学院上海有机化学研究所 | Production of sucrose ester by homogeneous solventless process |
| US6379937B1 (en) * | 2000-12-18 | 2002-04-30 | Council Of Scientific And Industrial Research | Process for the preparation of a mixture of 19 hydroxyelcosatetraenoic acid and 20 hydroxyeicosatetracnoic acid (10 hete and 20 hete) |
Non-Patent Citations (1)
| Title |
|---|
| 陈静等.酵母胞外槐糖脂产生条件优化及其抑菌作用.《山东大学学报(理学版)》.2005,第40卷(第3期),116-120. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1839892A (en) | 2006-10-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Kumara et al. | Rohitukine, a chromone alkaloid and a precursor of flavopiridol, is produced by endophytic fungi isolated from Dysoxylum binectariferum Hook. f and Amoora rohituka (Roxb). Wight & Arn | |
| CN1839892B (en) | Preparation method of yeast W.domercqiaeY2A variation waufa glucolipid crude extract with antineoplastic activity | |
| CN114606134B (en) | Sponge coanda fungus and application thereof in preparation of oxaanthraquinone compounds | |
| CN110452247B (en) | Heteroterpene compound and preparation method and application thereof | |
| CN102559828B (en) | Method for preparing astragaloside IV by converting total saponins of astragalus by microorganisms | |
| CN106047713B (en) | The basket bacteria strain Li-93 of one plant of thermophilic pine and its application | |
| CN101492706A (en) | Method for improving cordyceps sinensis bacterium native volume of production with cordyceps militaris link liquid fermentation | |
| CN107189949A (en) | Rhizopus oryzae LJH3 and the application in bioconversion Sophoricoside prepares genistein | |
| CN102329735B (en) | Method for preparing curvularin and indolizidine alkaloid and application | |
| CN104357332A (en) | Aspergillus niger JH-2 and application to biotransformation and synthesis of asiatic acid | |
| CN113248369A (en) | Preparation and application of polyketide compound with anti-new coronavirus activity | |
| CN116836818B (en) | Penicillium strain F8816 and application thereof | |
| CN104876945A (en) | Alkaloid dimer, preparation method thereof and application of alkaloid dimer as antiviral agent | |
| CN102363796A (en) | Method for producing glycyrrhetinic acid through microbial fermentation transformation | |
| CN107099464A (en) | A kind of sclerotium aspergillus and its method for preparing penicillic acid | |
| CN105754875B (en) | One plant of marine fungi Trichoderma harzianum DLEN2008005 and its application | |
| CN105441504B (en) | A kind of preparation method of CYCLIC DIPEPTIDES compounds | |
| CN101603011B (en) | Method for preparing epipodophyllotoxin diglucoside and special strain used thereby | |
| CN106282032B (en) | Penicillium citrinum LB and the application in phillygenol is prepared in bioconversion forsythin | |
| CN116103161A (en) | Plant endophytic fungus for producing eupatorium and application thereof | |
| CN105586372A (en) | Method for producing quercetin by means of microbial fermentation technology | |
| CN102584615A (en) | Alkaloid compound as well as preparation method and application thereof | |
| CN102337308A (en) | Method for converting bergenin into special nitrogenous derivative by using penicillium | |
| CN112961783A (en) | Plant endophytic fungus and application thereof in preparation of spironolactone derivative | |
| CN113502231B (en) | Rhizopus delemar Lut-8-53 and application thereof in preparation of luteolin by biotransformation method |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent for invention or patent application | ||
| CB03 | Change of inventor or designer information |
Inventor after: Song Xin Inventor after: Fan Zongzhong Inventor before: Song Xin Inventor before: Qu Yinbo Inventor before: Chen Jing |
|
| COR | Change of bibliographic data |
Free format text: CORRECT: INVENTOR; FROM: SONG XIN QU YINBO CHEN JING TO: SONG XIN FAN ZONGZHONG |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120919 Termination date: 20150113 |
|
| EXPY | Termination of patent right or utility model |