CN105497622B - A method of extracting Tricin from corn bract - Google Patents
A method of extracting Tricin from corn bract Download PDFInfo
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- CN105497622B CN105497622B CN201510989574.0A CN201510989574A CN105497622B CN 105497622 B CN105497622 B CN 105497622B CN 201510989574 A CN201510989574 A CN 201510989574A CN 105497622 B CN105497622 B CN 105497622B
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- 240000008042 Zea mays Species 0.000 title claims abstract description 115
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 title claims abstract description 114
- 235000002017 Zea mays subsp mays Nutrition 0.000 title claims abstract description 114
- 235000005822 corn Nutrition 0.000 title claims abstract description 114
- HRGUSFBJBOKSML-UHFFFAOYSA-N 3',5'-di-O-methyltricetin Chemical compound COC1=C(O)C(OC)=CC(C=2OC3=CC(O)=CC(O)=C3C(=O)C=2)=C1 HRGUSFBJBOKSML-UHFFFAOYSA-N 0.000 title claims abstract description 69
- IDDMFNIRSJVBHE-UHFFFAOYSA-N Piscigenin Natural products COC1=C(O)C(OC)=CC(C=2C(C3=C(O)C=C(O)C=C3OC=2)=O)=C1 IDDMFNIRSJVBHE-UHFFFAOYSA-N 0.000 title claims abstract description 69
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- BMCJATLPEJCACU-UHFFFAOYSA-N tricin Natural products COc1cc(OC)c(O)c(c1)C2=CC(=O)c3c(O)cc(O)cc3O2 BMCJATLPEJCACU-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 36
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- 238000004440 column chromatography Methods 0.000 claims abstract description 12
- 238000000926 separation method Methods 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 58
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/40—Separation, e.g. from natural material; Purification
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation or decoction
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/39—Complex extraction schemes, e.g. fractionation or repeated extraction steps
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- A—HUMAN NECESSITIES
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/55—Liquid-liquid separation; Phase separation
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Abstract
The method that the invention discloses a kind of to extract Tricin from corn bract takes extraction slag this method comprises: carrying out room temperature extraction to corn bract with water；With volume fraction be 80~90% and the ethanol solution refluxing extraction added with acid medium extracts slag, and gained extracting solution is concentrated under reduced pressure, concentrate is obtained；Concentrate is diluted with water and adjusts pH value to 7.8~8.2, takes supernatant after separation of solid and liquid；Macroporous adsorbent resin column chromatography is carried out to supernatant, obtains the corn bract extract containing Tricin.The impurity such as protein, polysaccharide first can be removed in advance with the extraction of water room temperature between alcohol extracting；Acid medium is added in the ethanol solution for refluxing extraction can effectively improve the extraction efficiency of small polarity Tricin；The pH value of concentrate dilution is adjusted to 7.8~8.2, the impurity such as chlorophyll, protein, polysaccharide in concentrate dilution precipitate rapidly under weakly alkaline environment at this time, greatly shorten the extracting cycle of Tricin.
Description
Technical field
The invention belongs to biomedicine fields, and in particular to a method of Tricin is extracted from corn bract.
Background technique
Tricin (tricin) is also known as tricin, triein.Tricin is yellow needles (Acetic Acid-Water), yellow
Powder (chloroform-methanol), 291-292 DEG C of fusing point.Tricin is present in gramineae plant awns
(MiscanthussinensisAnderss.) stem, Ye Zhong, leguminous plant alfalfa (MedicagosativaL.), composite family
In the plants such as plant.Tricin has relexation to isolated guinea pig intestinal tube, there is slight antioxidation, can prevent adrenaline oxygen
Change, and have slight estrogen-like action, also acts as dyestuff intermediate.But current market sales of Tricin Related product is big
It is mostly to be prepared from alfalfa,
It is mentioned from alfalfa as application publication number discloses one kind for the Chinese invention patent application of CN102911146A
The method for taking Tricin adds 5-8 times to measure the extraction of 60-80% alcohol reflux method includes the following steps: 1) alfalfa crushes
2-3 times, extracting solution is concentrated into no alcohol, is added in polyamide and adsorbs, ethanol solution gradient elution, and thin layer detection is collected high
After the concentration of concentration flow point plus ethyl acetate extraction, recycling ethyl acetate obtain crude product；2) take n-hexane, ethyl acetate, methanol, water mixed
It closes, phase is taken to fill high speed adverse current chromatogram column, rotate host, be pumped into lower phase and do mobile phase, flow phased soln crude product by sampling valve
Sample introduction, UV detector on-line monitoring, collects target component, merges flow point and is dried under reduced pressure to obtain high-purity Tricin.
Deficiency existing for the method for said extracted Tricin is: (1) alfalfa resource is limited, and it is deficient to extract raw material resources
It is weary；(2) extraction process is complicated, and uses the organic solvent compared with multiple types, and not only extraction cost is high, but also used has
Solvent all has biggish irritation and toxicity to operator and environment, and extraction process pole is not environmentally；(3) straight in step 1)
It connects using alcohol extracting, a large amount of biggish impurity of polarity are also extracted while isolating Tricin, so that carrying out finely
Before isolating and purifying, the purity of effective component is low in crude product, not only reduces extraction efficiency, also carefully isolates and purifies band to subsequent fine
Carry out larger inconvenience；(4) product price is high.
To solve the above problems, the Chinese patent literature that Authorization Notice No. is CN102040578B discloses one kind from the leaf of bamboo
The method of middle preparation high-purity Tricin, this method comprises: (a) makes the dry leaf of bamboo with 95% ethyl alcohol in 60 DEG C of refluxing extractions three
It is secondary, combined extracting solution is concentrated into no alcohol taste, then with petroleum ether extraction, water phase is condensed into medicinal extract；(b) make medicinal extract on a small quantity
Upper AB-8 macroporous resin column after the dissolution of 95% ethyl alcohol, is first eluted with pure water, then with 80% ethanol elution, eluent is concentrated and is done
It is dry；(c) methanol hydrochloride solution is added into step (b) desciccate, heating carries out acidolysis processing, with dilute NaOH after being disposed
Solution neutralizes；Wherein, the methanol hydrochloride solution is both methanol and 25% hydrochloric acid with the mixture of volume ratio 4:1, described to add
Heat is flowed back in boiling water bath, and the time of the acidolysis processing is 2 hours, and step (b) desciccate and hydrochloric acid methanol are molten
The ratio of liquid is 50mg:25ml；(d) mix acid hydrolysis solution obtained by step (c) with the C18 filler of sample equivalent weight, sample is mixed in concentration
It is dry, then dry C18 filler is made to mix sample solid loading, it is chromatographed by C18 column on the sample and proportion of filler of 1:10, first with 20%
Methanol aqueous solution elution, then eluted with 60% methanol aqueous solution, collect Tricin fraction, concentration；(e) make dense obtained by step (d)
Contracting object is dissolved with methanol, and by the sample and proportion of filler of 1:10, upper gel splitter makees mobile phase elution with pure methanol, is collected
Tricin fraction is concentrated to dry to get Tricin.
The extracting method is disadvantageous in that: (1) directlying adopt alcohol extracting in step (a), isolating the same of Tricin
The biggish impurity of Shi great Liang polarity is also extracted, so that before finely being isolated and purified (i.e. step (c)), in crude product
The purity of effective component is low (being only about 3%), not only reduces extraction efficiency, also carefully isolates and purifies and brought more very much not to subsequent fine
Just；(2) the biggish organic solvent of the irritations such as petroleum ether is still used in extraction process, and the dosage of ethyl alcohol is also larger.
Corn bract is the outer bract of grass family Zea plant Zea mays (ZeamaysL.), and pharmacological research shows corn bud
Piece water extract has the function of that reduce the blood lipid of artery sclerosis rabbit and defence hardens with treatment Arteries of Rabbits, containing rich in bract
Rich Tricin has anti-oxidant, relaxing smooth muscle, antitumor and plant growth regulation.
China is corn planting big country, and the bract acquired every year has 15,000,000 tons, after annual harvesting corn, there is a large amount of jade
Rice bract is discarded, and is not only the significant wastage of resource, also be polluted environment.The application is intended to provide a kind of from corn bract
The middle technique for extracting Tricin, turns waste into wealth.
Currently, mainly concentrating fuel, feed and handicraft knitting etc. to the report of corn bract both at home and abroad, not yet
The research that Tricin in corn bract is extracted.
Summary of the invention
The method that the present invention provides a kind of to extract Tricin from corn bract, this method solve lucernes in the prior art
The low problem of Mu element extraction efficiency.
A method of extracting Tricin from corn bract, comprising the following steps:
(1) room temperature extraction is carried out to corn bract with water, takes extraction slag；
(2) with volume fraction to extract slag described in 80~90% and the ethanol solution refluxing extraction added with hydrochloric acid, by institute
It obtains extracting solution to be concentrated under reduced pressure, obtains concentrate；
(3) concentrate is diluted with water and adjusts pH value to 7.8~8.2, take supernatant after separation of solid and liquid；
(4) macroporous adsorbent resin column chromatography is carried out to the supernatant, obtains the corn bract extract containing Tricin.
Since the polarity of Tricin is smaller, the present invention is first extracted with water room temperature before alcohol extracting, so can be preparatory
Protein, the biggish impurity of polysaccharide isopolarity are removed, avoids these impurity from dissolving in ethyl alcohol, increase subsequent large pore resin absorption column
Removal of impurities burden, reduce corn bract extract in impurity content.
Meanwhile step (2) adds hydrochloric acid in the ethanol solution for refluxing extraction, hydrochloric acid can effectively improve small polarity lucerne
The extraction efficiency of Mu element.
Also, the pH value of concentrate dilution is adjusted to 7.8~8.2 by step (3), and the leaf in concentrate dilution is green at this time
The impurity such as element, protein, polysaccharide precipitate rapidly under weakly alkaline environment, from without low temperature for a long time stand can room temperature it is dilute
It releases, be immediately disconnected, greatly shorten the extracting cycle of Tricin, also further reduce containing for impurity in corn bract extract
Amount；The content of Tricin is extremely after macroporous adsorbent resin column chromatography further removes impurity, in the corn bract extract of acquisition
Rare 10%.
Preferably, the corn bract is crushed to after granularity is less than 0.5cm and carries out room temperature extraction again in step (1).
Corn bract is suitably refined, the refluxing extraction efficiency for improving ethanol solution is conducive to.
As further preferred, in step (1), the room temperature extraction is to impregnate corn bract in water, corn bract
Mixed proportion with water is 1kg:8~10L, and soaking time is 2~4h；More preferably impregnate 3h.It can be in room temperature extraction process
Appropriate stirring, improves impurity dissolution rate.
Preferably, the hydrochloric acid is as acid medium in step (2).The acidity of hydrochloric acid is stronger, not only to macroporous absorption
Resin column and equipment are lossless (although sulfuric acid, nitric acid etc. are acid also relatively strong, corrosivity is also relatively strong simultaneously, unfavorable to equipment), only
Seldom amount need to be added and be able to achieve corresponding function；And it will not occur when subsequent progress macroporous adsorbent resin column chromatography residual
Stay (weak acid has residual, is unfavorable for large pore resin absorption column cleaning and directly recycles).
If not specified, heretofore described hydrochloric acid refer to commercially available concentrated hydrochloric acid (mass fraction is about 37%, mole
Concentration is 12mol/L).
As further preferred, the additive amount of the hydrochloric acid is the 0.01~0.05% of corn bract quality.Hydrochloric acid adds
If dosage is very few, extraction effect is unobvious；If additive amount is excessive, Tricin decomposition will lead to.
As further preferred, the additive amount of the hydrochloric acid is the 0.03~0.05% of corn bract quality.
In step (2), the number of refluxing extraction is more to can be improved refluxing extraction efficiency, preferably repeats to extract twice,
The w/v of corn bract and ethanol solution is preferred when extracting every time are as follows: 1kg:8~10L, each extraction time are at least 1
Hour.
Preferably, the concentrate is diluted with water to total solid content and accounts for 5~10% in step (3).Suitably
Dilution ratio both avoided supernatant volume it is excessive, increase subsequent progress macroporous adsorbent resin column chromatography when solvent usage amount,
It can guarantee the impurity such as chlorophyll, protein, the polysaccharide in concentrate fully Precipitation under weakly alkaline environment.
Preferably, the macroporous adsorbent resin column chromatography includes: that macropore is added in the supernatant to inhale in step (4)
In attached resin column, being first eluted with water to efflux pH value is 7.0~7.8, then the ethyl alcohol for being successively 15~20% with volume fraction
Solution, the ethanol solution that volume fraction is 70~80% elute, and collected volume score elutes institute for 70~80% ethanol solution
The stripping liquid is concentrated under reduced pressure, is dry, obtaining the corn bract extract containing Tricin by the stripping liquid obtained.
Since supernatant is in alkalescent, the biggish impurity of polarity after upper prop in supernatant can not then be adsorbed on macropore
It adsorbs on resin, the biggish Impurity elution of polarity can be got off by being first eluted with water；When efflux pH value is 7.0~7.8, pole
Property biggish impurity be eluted substantially, therefore continue the ethanol solution for using volume fraction to be 15~20% and elute to remove
Moderately polar impurity, to remove the impurity in corn bract extract as much as possible；Finally with volume fraction be 70~
80% ethanol solution elutes effective component, obtains the corn bract extract containing Tricin.
As further preferred, in step (4), low pole macroporous absorbent resin is loaded in the large pore resin absorption column；
LX11 macroporous absorbent resin can be selected.
As further preferred, in step (4), the drying is vacuum drying or spray drying, dry to the corn
The moisture content of bract extract is no more than 5%.Under the moisture content, microorganism is not easy to breed, corn bract extract
Long shelf-life.
The present invention also provides a kind of corn bract extract, which is prepared by the above method of the present invention
It forms, contains at least 10% Tricin.
Compared with prior art, the invention has the benefit that
(1) present invention before alcohol extracting first with water room temperature extract, can so remove in advance protein, polysaccharide isopolarity compared with
Big impurity avoids these impurity from dissolving in ethyl alcohol, increases the removal of impurities burden of subsequent large pore resin absorption column, reduces corn bract
Impurity content in extract, and the lesser Tricin of polarity can then be stayed in extract and be extracted in slag by ethanol solution；
(2) present invention adds hydrochloric acid in the ethanol solution for refluxing extraction, and hydrochloric acid can effectively improve small polarity clover
The extraction efficiency of element；
(3) pH value of concentrate dilution is adjusted to 7.8~8.2 by the present invention, at this time the chlorophyll in concentrate dilution,
The impurity such as protein, polysaccharide precipitate rapidly under weakly alkaline environment, can room temperature dilution, vertical from standing for a long time without low temperature
It separates, greatly shortens the extracting cycle of Tricin, also further reduce the content of impurity in corn bract extract；
(4) present invention is by weakly alkaline supernatant upper prop, and the biggish impurity of polarity can not be adsorbed on macropore suction in supernatant
On attached resin, therefore first it is eluted with water and the biggish Impurity elution of polarity can be got off；When efflux pH value is 7.0~7.8,
The biggish impurity of polarity is eluted substantially, therefore is continued the ethanol solution for using volume fraction to be 15~20% and eluted to remove
Moderately polar impurity is removed, to remove the impurity in corn bract extract as much as possible；It is finally 70 with volume fraction
~80% ethanol solution elutes, and the content at least 10% of Tricin, is the prior art in the corn bract extract of acquisition
In three times more than；
(5) organic solvent used in extraction process of the invention is only second alcohol and water, while the volume of ethanol solution is divided
Number is lower, and ethanol consumption is not only greatly saved, reduces extraction cost, and water and ethyl alcohol are to operator and environment base
This is non-stimulated, non-toxic, and extraction process is more environmentally friendly；
6) extracting method rational technology of the invention, easy to operate, suitable industrialized production.
Detailed description of the invention
Fig. 1 is that the HPLC of Tricin sterling detects figure；
Fig. 2 is that the HPLC of corn bract extract in embodiment 1 detects figure；
Fig. 3 is that the HPLC of corn bract extract in embodiment 2 detects figure；
Fig. 4 is that the HPLC of corn bract extract in embodiment 3 detects figure；
Fig. 5 is that the HPLC of corn bract extract in embodiment 4 detects figure；
Fig. 6 is that the HPLC of corn bract extract in embodiment 5 detects figure；
Fig. 7 is that the HPLC of corn bract extract in embodiment 6 detects figure；
Fig. 8 is that the HPLC of corn bract extract in comparative example 1 detects figure；
Fig. 9 is that the HPLC of corn bract extract in comparative example 2 detects figure；
Figure 10 is that the HPLC of corn bract extract in comparative example 3 detects figure；
Figure 11 is that the HPLC of corn bract extract in comparative example 4 detects figure；
Figure 12 is that the HPLC of corn bract extract in comparative example 5 detects figure；
Figure 13 is that the HPLC of corn bract extract in comparative example 6 detects figure；
Figure 14 is that the HPLC of corn bract extract in comparative example 7 detects figure；
Figure 15 is that the HPLC of corn bract extract in comparative example 8 detects figure；
Figure 16 is that the HPLC of corn bract extract in comparative example 9 detects figure；
Figure 17 is that the HPLC of corn bract extract in comparative example 10 detects figure.
Specific embodiment
Technical solution of the present invention is described in further detail with reference to the accompanying drawings and detailed description.
Embodiment 1
A kind of method that Tricin is extracted from corn bract of the present embodiment, comprising the following steps:
(1) broken (granularity the is less than 0.5cm) 10kg of dry corn bract is weighed, puts into 200L extractor, water is added
100L impregnates 3h under agitation, discards extracting solution, and it is spare to extract slag；
(2) it is 80% with volume fraction and is added with the ethanol solution refluxing extraction of hydrochloric acid (12mol/L) the extraction slag,
Gained extracting solution is concentrated under reduced pressure, concentrate is obtained；Wherein, the additive amount of hydrochloric acid be the broken quality of corn bract 0.03% (i.e.
0.003kg)；
Specifically: 1. to the ethanol solution 100L that addition volume fraction is 80% in slag is extracted, open stirring；
2. opening jacket steam, when being heated to alcohol reflux, start timing, refluxing extraction 1h；
3. after refluxing extraction, feed liquid is crossed 400 mesh filter bags, and putting into volume fraction again into filter residue is 80%
Ethanol solution 100L repeats refluxing extraction 1h；
4. after repeating refluxing extraction, secondary feed liquid is crossed into 400 mesh filter bags, and by secondary filtrate with 3. in filtrate close
And and suck 100L outer circulation；
5. opening outer circulation vacuum and steam, start to recycle ethyl alcohol, until blowing, weighing must be concentrated after distillate is without alcohol taste
Object；
(3) concentrate being diluted with water to total solid content and accounts for 8%, adding sodium hydroxide adjusts pH value to 8.0, then from
The heart, filtering, take supernatant；
(4) macroporous adsorbent resin column chromatography is carried out to supernatant, specifically:
1. supernatant to be passed through to the LX11 large pore resin absorption column of 25L with the flow velocity of 25L/h；
2. after upper prop, the larger impurity of the non-adsorbable polarity of resin is first gone with the flow velocity elution of 50L/h with 150L pure water,
Until efflux pH value is 7.0~7.8；
3. being easy to elute moderately polar impurity with the flow velocity of 15L/h with the ethyl alcohol that 50L volume fraction is 15% again；
4. finally being easy to desorb with the flow velocity of 10L/h with the ethyl alcohol that 25L volume fraction is 70%, stripping liquid is collected, will be solved
Imbibition is concentrated under reduced pressure to solid content up to 50% or more, and vacuum drying obtains dry extract 78.5g, as containing the jade of Tricin
Rice bract extract.
It is compared with Tricin sterling, HPLC detection, testing conditions is carried out to the corn bract extract are as follows:
Chromatographic column: HypersilODSC18 (4.6 × 250mm, 5 μm)；
Mobile phase: methanol-water (65:35)；
Flow velocity: 1.0ml/min；
Column temperature: 30 DEG C；
Detection wavelength: 349nm.
HPLC testing result such as Fig. 1 of Tricin sterling, the HPLC testing result of the present embodiment corn bract extract is such as
Fig. 2.
It is detected through HPLC it is found that clover cellulose content is 12.3% in the corn bract extract.
Embodiment 2
A kind of method that Tricin is extracted from corn bract of the present embodiment, comprising the following steps:
(1) broken (granularity the is less than 0.5cm) 300kg of dry corn bract is weighed, puts into 3000L extractor, water is added
2400L impregnates 3h under agitation, discards extracting solution, and it is spare to extract slag；
(2) it is 85% with volume fraction and is added with extraction described in the ethanol solution refluxing extraction of hydrochloric acid (12mol/L)
Gained extracting solution is concentrated under reduced pressure, obtains concentrate by slag；Wherein the additive amount of hydrochloric acid be the broken quality of corn bract 0.03% (i.e.
0.09kg)；
Specifically: 1. to the ethanol solution 2400L that addition volume fraction is 85% in slag is extracted, open stirring；
2. opening jacket steam, when being heated to alcohol reflux, start timing, refluxing extraction 1h；
3. after refluxing extraction, feed liquid is crossed 400 mesh filter bags, and putting into volume fraction again into filter residue is 85%
Ethanol solution 2400L repeats refluxing extraction 1h；
4. after repeating refluxing extraction, secondary feed liquid is crossed into 400 mesh filter bags, and by secondary filtrate with 3. in filtrate close
And and suck 1000L outer circulation；
5. opening outer circulation vacuum and steam, start to recycle ethyl alcohol, until blowing, weighing must be concentrated after distillate is without alcohol taste
Object；
(3) concentrate being diluted with water to total solid content and accounts for 10%, adding sodium hydroxide adjusts pH value to 8.1, then
Centrifugation, filtering, take supernatant；
(4) macroporous adsorbent resin column chromatography is carried out to supernatant, specifically:
1. supernatant to be passed through to the LX11 large pore resin absorption column of 1000L with the flow velocity of 1000L/h；
2. after upper prop, first going the non-adsorbable polarity of resin larger miscellaneous with the flow velocity elution of 2000L/h with 2000L pure water
Matter, until efflux pH value is 7.0~7.8；
3. eluting moderately polar impurity with the ethanol solution that 1000L volume fraction is 15% again with the flow velocity of 500L/h；
4. finally being desorbed with the ethanol solution that 1000L volume fraction is 75% with the flow velocity of 500L/h, stripping liquid is collected, it will
Stripping liquid is concentrated under reduced pressure to solid content up to 50% or more, and vacuum drying obtains dry extract 2.3kg, as containing Tricin
Corn bract extract.
(see Fig. 3) is known through HPLC detection (testing conditions are same as Example 1), Tricin in the corn bract extract
Content is 13.3%.
Embodiment 3
A kind of method that Tricin is extracted from corn bract of the present embodiment, comprising the following steps:
(1) broken (granularity the is less than 0.5cm) 200kg of dry corn bract is weighed, puts into 3000L extractor, water is added
2000L impregnates 3h under agitation, discards extracting solution, and it is spare to extract slag；
(2) it is 90% with volume fraction and is added with extraction described in the ethanol solution refluxing extraction of hydrochloric acid (12mol/L)
Gained extracting solution is concentrated under reduced pressure, obtains concentrate by slag；Wherein the additive amount of hydrochloric acid be the broken quality of corn bract 0.03% (i.e.
0.06kg)；
Specifically: above-mentioned ethanol solution 2000L 1. is added into extraction slag, opens stirring；
2. opening jacket steam, when being heated to alcohol reflux, start timing, refluxing extraction 2h；
3. after refluxing extraction, feed liquid is crossed 400 mesh filter bags, and put into above-mentioned ethanol solution again into filter residue
2000L repeats refluxing extraction 1h；
4. after repeating refluxing extraction, secondary feed liquid is crossed into 400 mesh filter bags, and by secondary filtrate with 3. in filtrate close
And and suck 1000L outer circulation；
5. opening outer circulation vacuum and steam, start to recycle ethyl alcohol, until blowing, weighing must be concentrated after distillate is without alcohol taste
Object；
(3) concentrate being diluted with water to total solid content and accounts for 10%, adding sodium hydroxide adjusts pH value to 8.2, then
Centrifugation, filtering, take supernatant；
(4) macroporous adsorbent resin column chromatography is carried out to supernatant, specifically:
1. supernatant to be passed through to the LX11 large pore resin absorption column of 1000L with the flow velocity of 1000L/h；
2. after upper prop, first going the non-adsorbable polarity of resin larger miscellaneous with the flow velocity elution of 2000L/h with 2000L pure water
Matter, until efflux pH value is 7.0~7.8；
3. eluting moderately polar impurity with the ethanol solution that 8000L volume fraction is 15% again with the flow velocity of 500L/h；
4. finally being easy to desorb with the flow velocity of 400L/h with the ethanol solution that 1200L volume fraction is 80%, desorption is collected
Stripping liquid is concentrated under reduced pressure to solid content up to 50% or more liquid, and vacuum drying obtains dry extract 1.5kg, as contains clover
The corn bract extract of element.
(see Fig. 4) is known through HPLC detection (testing conditions are same as Example 1), Tricin in the corn bract extract
Content is 14.6%.
Embodiment 4
Corn bract extract containing Tricin, but ethyl alcohol in step (2) are obtained using method same as Example 3
The additive amount of hydrochloric acid is changed to the 0.01% of the broken quality of corn bract in solution.
(see Fig. 5) is known through HPLC detection (testing conditions are same as Example 1), Tricin in the corn bract extract
Content is 11.6%.
Embodiment 5
Corn bract extract containing Tricin, but ethyl alcohol in step (2) are obtained using method same as Example 3
The additive amount of hydrochloric acid is changed to the 0.05% of the broken quality of corn bract in solution.
(see Fig. 6) is known through HPLC detection (testing conditions are same as Example 1), in corn bract extract obtained
Clover cellulose content is 13.5%.
Embodiment 6
A kind of method that Tricin is extracted from corn bract of the present embodiment, comprising the following steps:
(1) broken (granularity the is less than 0.5cm) 200kg of dry corn bract is weighed, puts into 3000L extractor, water is added
2000L impregnates 3h under agitation, discards extracting solution, and it is spare to extract slag；
(2) it is 90% with volume fraction and is added with extraction described in the ethanol solution refluxing extraction of hydrochloric acid (12mol/L)
Gained extracting solution is concentrated under reduced pressure, obtains concentrate by slag；Wherein the additive amount of hydrochloric acid be the broken quality of corn bract 0.03% (i.e.
0.06kg)；
Specifically: above-mentioned ethanol solution 2000L 1. is added into extraction slag, opens stirring；
2. opening jacket steam, when being heated to alcohol reflux, start timing, refluxing extraction 2h；
3. after refluxing extraction, feed liquid is crossed 400 mesh filter bags, and put into above-mentioned ethanol solution again into filter residue
2000L repeats refluxing extraction 1h；
4. after repeating refluxing extraction, secondary feed liquid is crossed into 400 mesh filter bags, and by secondary filtrate with 3. in filtrate close
And and suck 1000L outer circulation；
5. opening outer circulation vacuum and steam, start to recycle ethyl alcohol, until blowing, weighing must be concentrated after distillate is without alcohol taste
Object；
(3) concentrate being diluted with water to total solid content and accounts for 10%, adding sodium hydroxide adjusts pH value to 7.8, then
Centrifugation, filtering, take supernatant；
(4) macroporous adsorbent resin column chromatography is carried out to supernatant, specifically:
1. supernatant to be passed through to the LX11 large pore resin absorption column of 1000L with the flow velocity of 1000L/h；
2. after upper prop, first going the non-adsorbable polarity of resin larger miscellaneous with the flow velocity elution of 2000L/h with 2000L pure water
Matter, until efflux pH value is 7.0~7.8；
3. eluting moderately polar impurity with the ethanol solution that 8000L volume fraction is 20% again with the flow velocity of 500L/h；
4. finally being easy to desorb with the flow velocity of 400L/h with the ethanol solution that 1200L volume fraction is 80%, desorption is collected
Stripping liquid is concentrated under reduced pressure to solid content up to 50% or more liquid, and vacuum drying obtains dry extract 1.5kg, as contains clover
The corn bract extract of element.
(see Fig. 7) is known through HPLC detection (testing conditions are same as Example 1), in corn bract extract obtained
Clover cellulose content is 13.5%.
Comparative example 1
Corn bract extract containing Tricin, but the ethyl alcohol of step (2) are obtained using method same as Example 3
Hydrochloric acid is not added in solution.
(see Fig. 8) is known through HPLC detection (testing conditions are same as Example 1), in corn bract extract obtained
Clover cellulose content is 8.6%.
Comparative example 2
Corn bract extract containing Tricin, but the ethyl alcohol of step (2) are obtained using method same as Example 3
The additive amount of hydrochloric acid is changed to the 0.07% of the broken quality of corn bract in solution.
(see Fig. 9) is known through HPLC detection (testing conditions are same as Example 1), in corn bract extract obtained
Clover cellulose content is 11.4%.
Clover cellulose content is close with embodiment 4 in the corn bract extract, shows that excessive hydrochloric acid can promote Tricin to drop
Solution improves recovery rate unhelpful.
Comparative example 3
Corn bract extract containing Tricin is obtained using method same as Example 3, but lacks step (1),
It is i.e. directly that corn bract is broken using being 90% with volume fraction and carry out refluxing extraction added with the ethanol solution of hydrochloric acid.
(see Figure 10) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 9.8%.
Comparative example 4
Corn bract extract containing Tricin, but ethyl alcohol in step (2) are obtained using method same as Example 3
The volume fraction of solution is 95%.
(see Figure 11) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 12.1%.
Though clover cellulose content is higher in the corn bract extract, but still with 80% ethanol solution refluxing extraction when is close very
To slightly lower, to save ethanol consumption, do not use volume fraction for 95% ethanol solution.
Comparative example 5 obtains the corn bract extract containing Tricin, but step using method same as Example 3
(3) concentrate dilution pH is adjusted to 6.8 in.
(see Figure 12) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 12.0%.
Though clover cellulose content is higher in the corn bract extract, when pH is 6.8, precipitating is not easy to be precipitated in step (3),
Cause the time being separated by solid-liquid separation longer, extends the production cycle.
Comparative example 6
Corn bract extract containing Tricin is obtained using method same as Example 3, but will be dense in step (3)
Contracting object dilution pH is adjusted to 8.5.
(see Figure 13) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 11.8%.
After pH is improved, recovery rate is not improved and is reduced instead, it may be possible to because Tricin under the stronger environment of alkalinity not
Stablize, is easy to decompose.
Comparative example 7 obtains the corn bract extract containing Tricin, but step using method same as Example 3
(4) -3. in use volume fraction for 25% ethanol solution.
(see Figure 14) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 11.8%.
Comparative example 8
Corn bract extract containing Tricin is obtained using method same as Example 3, but step (4) -3. in
Use volume fraction for 10% ethanol solution.
(see Figure 15) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 11.5%.Show that the eluted fraction of ethanol solution is too low and is unfavorable for effectively removing for middle polarity impurity.
Comparative example 9
Corn bract extract containing Tricin is obtained using method same as Example 3, but step (4) -4. in
Use volume fraction for 65% ethanol solution.
(see Figure 16) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 11.7%.Show the too low desorption for being unfavorable for effective component of the volume fraction of ethanol solution.
Comparative example 10
Corn bract extract containing Tricin is obtained using method same as Example 3, but step (4) -4. in
Use volume fraction for 85% ethanol solution.
(see Figure 17) is known through HPLC detection (testing conditions are same as Example 1), corn bract extract obtained
Middle clover cellulose content is 12.1%.Show the volume fraction of ethanol solution it is excessively high will increase small polar impurity be eluted it is several
Rate.
Claims (2)
1. a kind of method for extracting Tricin from corn bract, which comprises the following steps:
(1) room temperature extraction is carried out to corn bract with water, takes extraction slag；
(2) gained is mentioned to extract slag described in 80~90% and the ethanol solution refluxing extraction added with hydrochloric acid with volume fraction
It takes liquid to be concentrated under reduced pressure, obtains concentrate；
(3) concentrate is diluted with water and adjusts pH value to 7.8~8.2, take supernatant after separation of solid and liquid；
(4) macroporous adsorbent resin column chromatography is carried out to the supernatant, obtains the corn bract extract containing Tricin；
In step (1), the corn bract is crushed to granularity less than carrying out room temperature extraction after 0.5cm again, in step (1), institute
Stating room temperature extraction is to impregnate corn bract in water, and the mixed proportion of corn bract and water is 1kg:8~10L, soaking time
For 2~4h, the additive amount of the hydrochloric acid is the 0.01~0.05% of corn bract quality, and in step (3), the concentrate is added
Water is diluted to total solid content and accounts for 5~10%, in step (4), the macroporous adsorbent resin column chromatography include: will be described on
Clear liquid is added in large pore resin absorption column, and being first eluted with water to efflux pH value is 7.0~7.8, then is successively with volume fraction
15~20% ethanol solution, the ethanol solution that volume fraction is 70~80% elute, and collected volume score is 70~80%
Ethanol solution elutes resulting stripping liquid, which is concentrated under reduced pressure, is dry, obtains the corn bract containing Tricin and extracts
Object, the large pore resin absorption column are LX11 large pore resin absorption column.
2. a kind of corn bract extract, which is characterized in that be prepared by claim 1 the method, contain at least 10%
Tricin.
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| CN104945450A (en) * | 2015-07-17 | 2015-09-30 | 湖南杰萃生物技术有限公司 | Method for extracting stibene glucoside from vines of multiflower knotweeds |
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| CN102241656A (en) * | 2011-05-06 | 2011-11-16 | 南京泽朗农业发展有限公司 | Preparation method of tricin |
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| CN104945450A (en) * | 2015-07-17 | 2015-09-30 | 湖南杰萃生物技术有限公司 | Method for extracting stibene glucoside from vines of multiflower knotweeds |
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