CN106380501A - Method for extracting stigmasterol from coix stems - Google Patents
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- CN106380501A CN106380501A CN201610646236.1A CN201610646236A CN106380501A CN 106380501 A CN106380501 A CN 106380501A CN 201610646236 A CN201610646236 A CN 201610646236A CN 106380501 A CN106380501 A CN 106380501A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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Abstract
The invention discloses a method for extracting stigmasterol from coix stems. The method comprises the following steps: enzymatic hydrolysis; ultrasonic extraction; saponification; urea column chromatography; crystallization; etc. The method provided by the invention can retain the natural characteristics of stigmasterol and has the advantages of few process steps, mild operation conditions, low solvent toxicity, safe production process and high extraction efficiency; and the extracted stigmasterol has a purity as high as 99%.
Description
Technical field
The present invention relates to the production preparation field of phytosterol is and in particular to extract the side of stigmasterol a kind of stem from Job's tears
Method.
Background technology
Stigmasterol (stigmaster01), C29H450.Molecular weight is 412, also known as beans steroid one 5,22 1 diene, one 3B mono- alcohol or
24R mono- ethyl cholesteric one 5,22 1 diene, one 3 B mono- alcohol, is plant sterols, is widely present in various plants.Stigmasterol
There is multiple pharmacologically active such as significantly anti-oxidant, antitumor, cardiovascular disease resistant, be also the initiation material of synthesis steroid medicine,
All there is application in industries such as medicine, food and chemical industry.In recent years, the development with the discovery of new steroid drugs, producing, production are advised
The expansion of mould, raw material requirement are also gradually increased；On the other hand due to irrational digging, cause shortage of resources, soap in plant
Salidroside content declines, and makes international market supply and demand contradiction, and the stigmasterol how obtaining more higher purity is stigmasterol research
One important directions.
Job's tears (Coix lachryma-jobiL. it is) grass family (Gramineae) Coix, slightly sweet flavor, cold nature,
There is invigorating the spleen, tonifying lung, heat-clearing, dampness removing, have the good reputation of " king of tonic ".At present the chemical composition of Job's tears is ground
Study carefully fewer, and more concentrate on coix seed, the document report of its pharmacology activity research aspect is also few, biological action thing
Matter basis is indefinite, leads to its application clinically to be limited to.Research has shown that Job's tears stem contains steroidal, polysaccharide, flavones, has
Machine acid, the chemical composition such as sheath matter, triterpene, therefore study and how to extract stigmasterol from Job's tears and can more make full use of Job's tears money
Source.
The Chinese patent of Publication No. CN1374319A discloses a kind of side extracting stigmasterol from mixed phytosterin
Method, the method solvent method is enriched with stigmasterol, and master operation includes water-bath dissolving, cooling growing the grain, insulation suction filtration, and its solvent adopts
Normal heptane and dichloroethanes mixed solvent, normal heptane：Dichloroethanes=l 1～2, l 1.5～1.8 is optimal.Wherein mixed plant steroid
Alcohol is l 3～5 with the mass volume ratio (m/V) of solvent, and 1 3.5～4.5 is optimal.Water-bath solution temperature is 70～75 DEG C.Water-bath
It is down to 20～25 DEG C, keep constant temperature growing the grain 12～24 hours.After terminating every time, last extract is pressed same process
Recrystallized next time, repeated 26 times, number of repetition is determined to extract the content of stigmasterol.Filtrate is through K cryogenic treatment, temperature
For -10 DEG C, reclaim steroid alcohol and solvent.The method solvent consumption is big, and production waste material is many, and energy ezpenditure is big, and sterol yield is low.
Content of the invention
In order to solve the above problems, the present invention provides a kind of method extracting stigmasterol stem from Job's tears, the side of the present invention
Method can keep the natural characteristic of product, and processing step is few, and operating condition is gentle, and solvent toxicity is low, production technology safety, extracts
Efficiency high, product purity is up to 99%.
The present invention is achieved through the following technical solutions：
A kind of method extracting stigmasterol stem from Job's tears, comprises the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 1～3 times of meal weight, digests 5～8h at 30～50 DEG C, filters, and is dried, and obtains digesting the heart of a lotus seed
Job's tears stem powder；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added in ultrasonic equipment and carries out ultrasonic wave extraction, mistake
Filter, obtains extract, extract is put in Rotary Evaporators and carries out reduced pressure concentration, obtain extractum A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 10～50wt%, it is sufficiently stirred for, at 40～70 DEG C
Saponification 1～3h, reactant liquor is neutralized with hydrochloric acid to neutrality, then uses saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded, petroleum ether
Carry out reduced pressure concentration with Rotary Evaporators, obtain medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in loaded solvent, is subsequently adding silica gel, so that urea is supported on silica gel, remove negative
Carry solvent, prepared fixing phase；Fixing phase is filled post, then by medicinal extract B upper prop, carries out being eluted to no with eluant, eluent injection chromatographic column
Stigmasterol flows out, and collects eluent, by thin-layer chromatography tracing detection, merges and stigmasterol standard items Rf value identical wash-out
Liquid, is concentrated to give stigmasterol crude product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
Preferably, the weight of the above cellulase and pectase addition is the 0.1～1% of Job's tears stem meal weight, fine
The plain enzyme of dimension and pectase are mixed with arbitrary proportion.
Preferably, the solid-liquid ratio 1 of the above enzymolysis Job's tears stem powder and absolute ethyl alcohol:10～15.
Preferably, the above multi-frequency ultrasonic is extracted as double frequency or Three-frequency ultrasonic extracts, and is carried using dual-frequency ultrasonic wave
When taking, the frequency of two kinds of ultrasonic waves is 20～40kHz and 20～60kHz, and power is 50～200W, 100～500W, extraction time
For 20～40min；When being extracted using Three-frequency ultrasonic, the frequency of three kinds of ultrasonic waves is 20～40kHz, 20～60kHz, 500～
1000kHz, power is 50～200W, 100～500W, 500～2000W, and extraction time is 10～25min.
Preferably, the ethanol solution of the NaOH of the above 10～50wt% and the solid-liquid ratio of extractum A are 3～10:
1.
Preferably, the above loaded solvent is absolute ethyl alcohol or 75～95% ethanol-water solution.
Preferably, the mass ratio of the above urea and silica gel is 1～10:3.
Preferably, the above eluant, eluent is 10 for volume ratio:1～2:1 benzene-ethyl acetate solution.
Compared with prior art, advantages of the present invention and having the beneficial effect that：
1st, the present invention adds pectase and cellulase to be digested in Job's tears stem meal, can destroy the cell of Job's tears stem
Wall, makes stigmasterol be easier to be suggested out, moreover it is possible to remove the water-solubility impurities such as par-tial polysaccharide after filtration, improves stigmasterol
Recovery rate.
2nd, the present invention adopts multi-frequency ultrasonic to extract, and can significantly shorten extraction time, reduces solvent load, improves
Rate, and the extract quality obtaining is good, easily refined.
3rd, the present invention is isolated and purified using urea column chromatography, simple to operate, low cost, and urea chromatographic column can repeat
Using.
4th, the method for the present invention can keep the natural characteristic of product, and processing step is few, and operating condition is gentle, solvent toxicity
Low, production technology safety, extraction efficiency is high, and product purity is up to 99%.
5th, the present invention extracts stigmasterol by the use of agricultural wastes Job's tears stem as raw material, can reduce the row of agricultural wastes
Put, increase the utilization rate of coix plant, improve farmers' income, preserve the ecological environment.
Specific embodiment
Embodiment 1
A kind of method extracting stigmasterol stem from Job's tears, comprises the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 1 times of meal weight, digests 8h at 50 DEG C, filters, and is dried, and obtains digesting Job's tears stem powder；Wherein
The weight that cellulase and pectase add is the 0.1% of Job's tears stem meal weight, and the weight of cellulase and pectase ratio is for 2:
1；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added and in ultrasonic equipment, carries out double ultrasonic wave extractions, enzyme
Solution Job's tears stem powder and the solid-liquid ratio 1 of absolute ethyl alcohol:10, the frequency of two kinds of ultrasonic waves is 20kHz and 40kHz, power is 50W,
100W, extraction time is 20min；Filter, obtain extract, extract is put in Rotary Evaporators and carries out reduced pressure concentration, obtain leaching
Cream A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 10wt%, the ethanol of the NaOH of 10wt% is molten
Liquid is 3 with the solid-liquid ratio of extractum A:1, it is sufficiently stirred for, saponification 1h at 40～50 DEG C, reactant liquor is neutralized with hydrochloric acid to neutrality, so
Use saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded afterwards, petroleum ether carries out reduced pressure concentration with Rotary Evaporators, obtains medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in absolute ethyl alcohol, is subsequently adding silica gel, so that urea is supported on silica gel, urea and
The mass ratio of silica gel is 1:3, remove absolute ethyl alcohol, prepared fixing phase；Fixing phase is filled post, then by medicinal extract B upper prop, uses volume
Than for 10:1 benzene-ethyl acetate solution injection chromatographic column carries out being eluted to no stigmasterol outflow, collects eluent, by thin layer
Chromatography tracing detection, merges and stigmasterol standard items Rf value identical eluent, is concentrated to give stigmasterol crude product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
The stigmasterol sterling that the present embodiment obtains adopts HPLC to detect, purity is 99.0%.
Embodiment 2
A kind of method extracting stigmasterol stem from Job's tears, comprises the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 3 times of meal weight, digests 5h at 30 DEG C, filters, and is dried, and obtains digesting Job's tears stem powder；Wherein
The weight that cellulase and pectase add is the 1% of Job's tears stem meal weight, and the weight of cellulase and pectase ratio is for 2:1；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added in ultrasonic equipment and carry out Three-frequency ultrasonic extraction,
Enzymolysis Job's tears stem powder and the solid-liquid ratio 1 of absolute ethyl alcohol:15, the frequency of three kinds of ultrasonic waves is 40kHz, 60kHz, 1000kHz, power
For 200W, 500W, 2000W, extraction time is 10min；Filter, obtain extract, extract is put in Rotary Evaporators and carries out
Reduced pressure concentration, obtains extractum A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 50wt%, the ethanol of the NaOH of 50wt% is molten
Liquid is 10 with the solid-liquid ratio of extractum A:1, it is sufficiently stirred for, saponification 3h at 50～70 DEG C, reactant liquor is neutralized with hydrochloric acid to neutrality, so
Use saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded afterwards, petroleum ether carries out reduced pressure concentration with Rotary Evaporators, obtains medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in 75% ethanol-water solution, is subsequently adding silica gel, make urea be supported on silica gel
On, the mass ratio of urea and silica gel is 10:3, remove 75% ethanol-water solution, prepared fixing phase；Fixing phase is filled post, then
By medicinal extract B upper prop, it is 2 with volume ratio:1 benzene-ethyl acetate solution injection chromatographic column carries out being eluted to no stigmasterol outflow, receives
Collection eluent, by thin-layer chromatography tracing detection, merges and stigmasterol standard items Rf value identical eluent, is concentrated to give stigmasterol
Crude product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
The stigmasterol sterling that the present embodiment obtains adopts HPLC to detect, purity is 99.2%.
Embodiment 3
A kind of method extracting stigmasterol stem from Job's tears, comprises the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 2 times of meal weight, digests 6h at 40 DEG C, filters, and is dried, and obtains digesting Job's tears stem powder；Wherein
The weight that cellulase and pectase add is the 0.5% of Job's tears stem meal weight, and the weight of cellulase and pectase ratio is for 1:
1；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added in ultrasonic equipment and carry out dual-frequency ultrasonic wave extraction,
Enzymolysis Job's tears stem powder and the solid-liquid ratio 1 of absolute ethyl alcohol:12, the frequency of two kinds of ultrasonic waves is 35kHz and 55kHz, power is 100W,
200W, extraction time is 30min；Filter, obtain extract, extract is put in Rotary Evaporators and carries out reduced pressure concentration, obtain leaching
Cream A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 30wt%, the ethanol of the NaOH of 30wt% is molten
Liquid is 6 with the solid-liquid ratio of extractum A:1, it is sufficiently stirred for, saponification 2h at 50～60 DEG C, reactant liquor is neutralized with hydrochloric acid to neutrality, so
Use saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded afterwards, petroleum ether carries out reduced pressure concentration with Rotary Evaporators, obtains medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in 95% ethanol-water solution, is subsequently adding silica gel, make urea be supported on silica gel
On, the mass ratio of urea and silica gel is 5:3, remove 95% ethanol-water solution, prepared fixing phase；Fixing phase is filled post, then
By medicinal extract B upper prop, it is 5 with volume ratio:1 benzene-ethyl acetate solution injection chromatographic column carries out being eluted to no stigmasterol outflow, receives
Collection eluent, by thin-layer chromatography tracing detection, merges and stigmasterol standard items Rf value identical eluent, is concentrated to give stigmasterol
Crude product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
The stigmasterol sterling that the present embodiment obtains adopts HPLC to detect, purity is 99.1%.
Embodiment 4
A kind of method extracting stigmasterol stem from Job's tears, comprises the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 2 times of meal weight, digests 6h at 50 DEG C, filters, and is dried, and obtains digesting Job's tears stem powder；Wherein
The weight that cellulase and pectase add is the 0.8% of Job's tears stem meal weight, and the weight of cellulase and pectase ratio is for 1:
3；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added in ultrasonic equipment and carry out Three-frequency ultrasonic extraction,
Enzymolysis Job's tears stem powder and the solid-liquid ratio 1 of absolute ethyl alcohol:12, the frequency of three kinds of ultrasonic waves is 20kHz, 40kHz, 500kHz, power
For 50,100W, 500W, extraction time is 25min.Filter, obtain extract, extract is put in Rotary Evaporators and is reduced pressure
Concentrate, obtain extractum A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 20wt%, the ethanol of the NaOH of 20wt% is molten
Liquid is 6 with the solid-liquid ratio of extractum A:1, it is sufficiently stirred for, saponification 1h at 50～60 DEG C, reactant liquor is neutralized with hydrochloric acid to neutrality, so
Use saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded afterwards, petroleum ether carries out reduced pressure concentration with Rotary Evaporators, obtains medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in 80% ethanol-water solution, is subsequently adding silica gel, so that urea is supported on silica gel,
The mass ratio of urea and silica gel is 6:3, remove 80% ethanol-water solution, prepared fixing phase；Fixing phase is filled post, then will soak
Cream B upper prop, is 3 with volume ratio:1 benzene-ethyl acetate solution injection chromatographic column carries out being eluted to no stigmasterol outflow, and collection is washed
De- liquid, by thin-layer chromatography tracing detection, merges and stigmasterol standard items Rf value identical eluent, is concentrated to give stigmasterol thick
Product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
The stigmasterol sterling that the present embodiment obtains adopts HPLC to detect, purity is 99.2%.
Embodiment 5
A kind of method extracting stigmasterol stem from Job's tears, comprises the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 3 times of meal weight, digests 8h at 40 DEG C, filters, and is dried, and obtains digesting Job's tears stem powder；Wherein
The weight that cellulase and pectase add is the 0.6% of Job's tears stem meal weight, and the weight of cellulase and pectase ratio is for 1:
1；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added in ultrasonic equipment and carry out dual-frequency ultrasonic wave extraction,
Enzymolysis Job's tears stem powder and the solid-liquid ratio 1 of absolute ethyl alcohol:12, the frequency of two kinds of ultrasonic waves is 40kHz and 20kHz, power is 200W,
500W, extraction time is 25min；Filter, obtain extract, extract is put in Rotary Evaporators and carries out reduced pressure concentration, obtain leaching
Cream A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 20wt%, the ethanol of the NaOH of 20wt% is molten
Liquid is 8 with the solid-liquid ratio of extractum A:1, it is sufficiently stirred for, saponification 2h at 50～60 DEG C, reactant liquor is neutralized with hydrochloric acid to neutrality, so
Use saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded afterwards, petroleum ether carries out reduced pressure concentration with Rotary Evaporators, obtains medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in absolute ethyl alcohol, is subsequently adding silica gel, so that urea is supported on silica gel, urea and
The mass ratio of silica gel is 5:3, remove absolute ethyl alcohol, prepared fixing phase；Fixing phase is filled post, then by medicinal extract B upper prop, uses volume
Than for 5:1 benzene-ethyl acetate solution injection chromatographic column carries out being eluted to no stigmasterol outflow, collects eluent, by thin layer
Chromatography tracing detection, merges and stigmasterol standard items Rf value identical eluent, is concentrated to give stigmasterol crude product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
The stigmasterol sterling that the present embodiment obtains adopts HPLC to detect, purity is 99.3%.
Claims (8)
1. extract the method for stigmasterol a kind of stem from Job's tears it is characterised in that comprising the following steps：
（1）Enzymolysis：Job's tears stem is put into and in pulverizer, pulverizes to obtain Job's tears stem meal, in Job's tears stem meal add cellulase and
Pectase, is then dissolved in the water of 1～3 times of meal weight, digests 5～8h at 30～50 DEG C, filters, and is dried, and obtains digesting the heart of a lotus seed
Job's tears stem powder；
（2）Ultrasonic wave extraction：Enzymolysis Job's tears stem powder and absolute ethyl alcohol are added in ultrasonic equipment and carries out ultrasonic wave extraction, mistake
Filter, obtains extract, extract is put in Rotary Evaporators and carries out reduced pressure concentration, obtain extractum A；
（3）Saponification：In the ethanol solution of NaOH extractum A being dissolved in 10～50wt%, it is sufficiently stirred for, at 40～70 DEG C
Saponification 1～3h, reactant liquor is neutralized with hydrochloric acid to neutrality, then uses saturated aqueous common salt and petroleum ether extraction, aqueous phase discarded, petroleum ether
Carry out reduced pressure concentration with Rotary Evaporators, obtain medicinal extract B；
（4）Urea column chromatography：Urea is dissolved in loaded solvent, is subsequently adding silica gel, so that urea is supported on silica gel, remove negative
Carry solvent, prepared fixing phase；Fixing phase is filled post, then by medicinal extract B upper prop, carries out being eluted to no with eluant, eluent injection chromatographic column
Stigmasterol flows out, and collects eluent, by thin-layer chromatography tracing detection, merges and stigmasterol standard items Rf value identical wash-out
Liquid, is concentrated to give stigmasterol crude product；
（5）Crystallization：Stigmasterol crude product is dissolved in methyl alcohol, crystallization, filters, obtain stigmasterol sterling.
2. the stem from Job's tears according to claim 1 extract stigmasterol method it is characterised in that described cellulase and
The weight that pectase adds is the 0.1～1% of Job's tears stem meal weight, and cellulase and pectase are mixed with arbitrary proportion.
3. extract the method for stigmasterol the stem from Job's tears according to claim 1 it is characterised in that described enzymolysis Job's tears stem
The solid-liquid ratio 1 of powder and absolute ethyl alcohol:10～15.
4. extract the method for stigmasterol the stem from Job's tears according to claim 1 it is characterised in that described ultrasonic wave extraction
Be that double frequency or Three-frequency ultrasonic extract, when being extracted using dual-frequency ultrasonic wave, the frequency of two kinds of ultrasonic waves for 20～40kHz and 20～
60kHz, power is 50～200W, 100～500W, and extraction time is 20～40min；When being extracted using Three-frequency ultrasonic, three kinds
The frequency of ultrasonic wave be 20～40kHz, 20～60kHz, 500～1000kHz, power be 50～200W, 100～500W, 500～
2000W, extraction time is 10～25min.
5. extract the method for stigmasterol the stem from Job's tears according to claim 1 it is characterised in that described 10～50wt%
The solid-liquid ratio of the ethanol solution of NaOH and extractum A be 3～10:1.
6. extract the method for stigmasterol the stem from Job's tears according to claim 1 it is characterised in that described loaded solvent is
Absolute ethyl alcohol or 75～95% ethanol-water solution.
7. extract the method for stigmasterol the stem from Job's tears according to claim 1 it is characterised in that described urea and silica gel
Mass ratio be 1～10:3.
8. extract the method for stigmasterol the stem from Job's tears according to claim 1 it is characterised in that described eluant, eluent is body
Long-pending ratio is 10:1～2:1 benzene-ethyl acetate solution.
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| CN107383141A (en) * | 2017-08-30 | 2017-11-24 | 右江民族医学院 | The method that the ketone of 24 ethyl cholestane of (20R) 22E, 4,22 diene 3 is extracted in Job's tears cauline leaf |
| CN107513091A (en) * | 2017-08-30 | 2017-12-26 | 右江民族医学院 | There is the compound and its extracting method of antitumor activity in Job's tears cauline leaf |
| CN107625774A (en) * | 2017-08-30 | 2018-01-26 | 右江民族医学院 | Application and its extracting method of the cycloartenol in antineoplastic in Job's tears cauline leaf |
| CN107652349A (en) * | 2017-08-30 | 2018-02-02 | 右江民族医学院 | A kind of method that cycloartenol is isolated and purified in the cauline leaf from Job's tears |
| CN110642962A (en) * | 2019-09-03 | 2020-01-03 | 南昌大学 | Separation and purification method of hybrid bean pectin polysaccharide |
| CN110642962B (en) * | 2019-09-03 | 2022-03-22 | 南昌大学 | Separation and purification method of hybrid bean pectin polysaccharide |
| CN113512084A (en) * | 2021-03-26 | 2021-10-19 | 右江民族医学院 | Method for extracting stigmasterol from coix stems and leaves by combining ultrasonic countercurrent with biological enzyme |
| CN113512084B (en) * | 2021-03-26 | 2023-09-26 | 右江民族医学院 | Method for extracting stigmasterol from coix seed stems and leaves by combining ultrasonic countercurrent with biological enzyme |
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