CN105777699B - A kind of preparation method of non agricultural chemical residuum black rice anthocyanin - Google Patents
A kind of preparation method of non agricultural chemical residuum black rice anthocyanin Download PDFInfo
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- CN105777699B CN105777699B CN201610335330.5A CN201610335330A CN105777699B CN 105777699 B CN105777699 B CN 105777699B CN 201610335330 A CN201610335330 A CN 201610335330A CN 105777699 B CN105777699 B CN 105777699B
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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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
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- Medicines Containing Plant Substances (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
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Abstract
Disclosed by the invention is the process that extraction purification prepares non agricultural chemical residuum anthocyanidin from black rice, and this method comprises the following steps：（1）Black rice extracts：Black rice raw material is taken, first adds raw material weight 5% 9%, the aqueous citric acid solution that mass fraction is 50 60%, it is 1 to be supplemented pure water to solid-liquid ratio:2‑1:3, after extracting 8 10 hours, coarse filtration, centrifugation, centrifugate using aperture as 0.5 micron of ceramic membrane filter, obtain filtrate again respectively；（2）Purifying：Purified using macroporous absorbent resin, eluted using the ethanol water that mass fraction is 40 60%；（3）Extraction：Extract and separate is carried out using the petroleum ether of 12 times of volumes, removes part residues of pesticides；（4）Silica gel column chromatography：Residues of pesticides are further removed through silica gel column chromatography；（5）Dry：Spray-dried that powdered black rice anthocyanin product is made, its anthocyanidin content is more than 30%, and residues of pesticides do not detect；Present invention process is simple, non agricultural chemical residuum, and anthocyanidin content is high, can fully meet the market demand, ensures food security.
Description
Technical field
The preparation side of the black rice anthocyanin of non agricultural chemical residuum is prepared the present invention relates to extraction purification in a kind of raw material from black rice
Method.
Background technology
Black rice（Black rice）, in black or dark brown, belong to glutinous rice class, be to be cultivated by grass rice through long-term
A kind of feature breed of formation, it is nutritious, containing abundant anthocyania pigment, there is strengthen immunity, hypotensive, enhancing to regard
Power, eliminate kopiopia, the multiple efficacies such as anti-oxidant.China is that Rice Cropping big country, especially black rice resource are wider in the world
Wealthy, the black rice anthocyanin application that it is rich in is wider, can be applied in the fields such as ordinary food, health food and medicine, tool
There are good market prospects.But current black rice widely uses the agricultural chemicals such as Isoprothiolane, Triadimenol in planting process.After testing, not
Isoprothiolane content reaches 0.8mg/100kg, agricultural chemicals total content 1.2mg/100kg in black rice before processing.It is single to seem agriculture in terms of numeral
Residual is little, but industrially from black rice during extraction black rice anthocyanin, general raw material is all in terms of ton, therefore, if not in technique
During carry out the residual removal of agriculture, final products Pesticides enrichment amount will greatly exceed national standard（GB 2763-2014）Institute
Defined MRL（0.01mg/kg）.And the presently disclosed extraction process for anthocyanidin in black rice, such as China are specially
Sharp application number 201510297289.2（A kind of technique that anthocyanidin is extracted from black rice）, it is 50 DEG C of water after black rice raw material is crushed
Bath 1:5-15 solid-liquid ratios are extracted, and centrifugation, ultrafiltration membrance filter of the supernatant through 3000Da, efflux is purified through macroreticular resin,
Vacuum freeze drying obtains the black rice anthocyanin of aubergine.Also Chinese Patent Application No. 201410466396.9（High-purity is black
Anthocyanin preparation technology）, it is using black rice as raw material, after extracted, filtering, concentration, is purified using polyamide resin column, winestone
Sour ethanol solution is desorbed, and prepares high-purity black rice anthocyanin, and color value reaches 500.This two technical schemes only stress cyanine
The extraction of element, the residual for whether also having agricultural chemicals in anthocyanidin is extracted without paying close attention to.And Isoprothiolane is black rice intensely processed products
In main residues of pesticides material, in general process is difficult to remove completely.With adding for people's Consciousness of food security
By force, market comes out with greater need for the black rice anthocyanin of non agricultural chemical residuum.Therefore, high-purity high-yield can be kept again without agriculture by working out
The process of medicine residual, is industry technical problem urgently to be resolved hurrily.
The content of the invention
It is an object of the invention to provide a kind of preparation method of the black rice anthocyanin of non agricultural chemical residuum.The letter of this method technique
Single, anthocyanidin content is more than 30%, non agricultural chemical residuum.
Technical solution of the present invention comprises the steps：
（1）Black rice extracts：Black rice raw material is taken, first adds raw material weight 5%-9%, the citric acid that mass fraction is 50-60%
The aqueous solution, it is 1 to be supplemented pure water to solid-liquid ratio:2-1:3, extract 8-10 hours after, respectively coarse filtration, centrifugation, centrifugate again with
Aperture is 0.5 micron of ceramic membrane filter, obtains filtrate；
（2）Purifying：Above-mentioned filtrate is added into macroporous resin column, upper prop flow control is in 0.8-1.2BV/h, then uses matter
Measure the ethanol water that fraction is 40-60% to elute, elution volume 6-8BV, collect eluent, be concentrated into soluble solid
Content Brix 30%-40%；
（3）Extraction：Concentrate is diluted to soluble solid content Brix 10%-20% with pure water, uses concentrated liquid
The petroleum ether extraction of 1-2 times of product 1-2 times, remains of pesticide enter in the petroleum ether extraction liquid of upper strata, and lower floor's solution is concentrated into can
Dissolubility solid content Brix 30-40%；
（4）Silica gel column chromatography：By step（3）Silica gel column chromatography on the concentrate of gained, silica gel dosage are concentrate
0.5-1 times；First eluted with ethyl acetate, the agricultural chemicals for making to remain in concentrate, which is dissolved in ethyl acetate, further to be removed, elution
Volume is 2-3BV；40-60% ethanol elutions are used again, elution volume 2-3BV, collect ethanol eluate；
（5）Dry：By step（4）Resulting ethanol eluate is concentrated under reduced pressure into soluble solid content Brix
50%-60%, ethanol is reclaimed, concentrate is spray-dried to be made powdered black rice anthocyanin, and anthocyanidin content is more than after testing
30%, agricultural chemicals does not detect.
Described aqueous citric acid solution preferred mass fraction is 57%, and it is mainly color protection that it, which is acted on, in case subsequent operation is to black
The destruction of anthocyanin.
Macroreticular resin used is preferably AB-8 type macroreticular resins.
Used silica gel dosage is preferably 0.8 times of concentrate.
Optimal technical scheme of the present invention is as follows：
（1）Black rice extracts：The black rice raw material that is produced from somewhere is taken, after testing wherein Isoprothiolane content 0.8mg/100kg, agriculture
Medicine total content 1.2mg/100kg, first add raw material weight 8.5%, the aqueous citric acid solution that mass fraction is 57%, be supplemented pure
Water to solid-liquid ratio is 1:3, after extraction 10 hours, coarse filtration, centrifugation respectively, centrifugate again with the ceramic membrane filter in 0.5 micron of aperture,
Obtain filtrate；
（2）Purifying：Above-mentioned filtrate is added into AB-8 type macroporous resin columns, upper prop flow control is in 1.0BV/h, then uses
The ethanol water that mass fraction is 60% elutes, and elution volume 7BV, collects eluent, is concentrated into soluble solid content
Brix 35%；
（3）Extraction：Concentrate is diluted to soluble solid content Brix 15% with pure water, uses the volume of concentrate
1.5 times of petroleum ether extraction 2 times, remains of pesticide enter in the petroleum ether extraction liquid of upper strata, and lower floor's solution is concentrated into solubility
Solid content Brix 40%；
（4）Silica gel column chromatography：By step（3）Silica gel column chromatography on the concentrate of gained, silica gel dosage are the 0.8 of concentrate
Times；First eluted with ethyl acetate, the agricultural chemicals for making to remain in concentrate, which is dissolved in ethyl acetate, further to be removed, and elution volume is
2BV；Again with 50% ethanol elution, elution volume 2.5BV, ethanol eluate is collected；
（5）Dry：By step（4）Resulting ethanol eluate is concentrated under reduced pressure into soluble solid content Brix
55%, ethanol is reclaimed, concentrate is spray-dried to be made powdered black rice anthocyanin, and anthocyanidin content is 33.2% after testing, agriculture
Medicine does not detect.
The present invention compared with prior art, has advantages below：
(1) Isoprothiolane belongs to efficient, the less toxic, organosulfureous fungicide of low-residual, sub- penta rings of the entitled sulphur -2- of 1,3- bis- of chemistry
Propylmalonic acid diisopropyl ester, Triadimenol chemistry entitled 1 one（4 monochloro-benzene epoxides）(the 1H-1,2,4 tri- of one 3,3 one dimethyl 1
Azoles-l- bases) -2- butanol.The present invention utilizes the principle of " similar to mix ", and concentrate after purifying resin is extracted using petroleum ether
Take, the agricultural chemicals total content such as Isoprothiolane can be reduced to 0.42mg/kg or following；The extraction process technique is simple, effective to remove
The a large amount of residues of pesticides brought into by black rice raw material.
(2) the chemistry of pesticide compositions such as black rice anthocyanin, Isoprothiolane and Triadimenol and the difference of silica filler affinity are utilized,
Separated using the method for silica gel column chromatography.Because anthocyanidin affinity is stronger, and the agricultural chemicals remained is then washed with ethyl acetate
De- liquid stream goes out, so that the remains of pesticide in feed liquid is further removed.It is demonstrated experimentally that after above-mentioned silica gel post separation, it is residual
Agricultural chemicals is stayed to remove substantially, agricultural chemicals Isoprothiolane content is reduced to below 0.01mg/kg（Less than detection limit）.The present invention is solvent-free residual
Stay, technique is simple, stable, easy industrialization, it is ensured that food security, improves product quality and competitiveness.
Embodiment
Below by way of the specific purification embodiment of three different sources black rice raw materials, the invention will be further described.
Embodiment 1
（1）Black rice extracts：The black rice raw material that is produced from somewhere is taken, after testing wherein Isoprothiolane content 0.8mg/100kg, agriculture
Medicine total content 1.2mg/100kg, first add raw material weight 8.5%, the aqueous citric acid solution that mass fraction is 57%, be supplemented pure
Water to solid-liquid ratio is 1:3, after extraction 10 hours, coarse filtration, centrifugation respectively, centrifugate again with the ceramic membrane filter in 0.5 micron of aperture,
Obtain filtrate；
（2）Purifying：Above-mentioned filtrate is added into AB-8 type macroporous resin columns, upper prop flow control is in 1.0BV/h, then uses
The ethanol water that mass fraction is 60% elutes, and elution volume 7BV, collects eluent, is concentrated into soluble solid content
Brix 35%；
（3）Extraction：Concentrate is diluted to soluble solid content Brix 15% with pure water, uses the volume of concentrate
1.5 times of petroleum ether extraction 2 times, remains of pesticide enter in the petroleum ether extraction liquid of upper strata, and lower floor's solution is concentrated into solubility
Solid content Brix 40%；
（4）Silica gel column chromatography：By step（3）Silica gel column chromatography on the concentrate of gained, silica gel dosage are the 0.8 of concentrate
Times；First eluted with ethyl acetate, the agricultural chemicals for making to remain in concentrate, which is dissolved in ethyl acetate, further to be removed, and elution volume is
2BV；Again with 50% ethanol elution, elution volume 2.5BV, ethanol eluate is collected；
（5）Dry：By step（4）Resulting ethanol eluate is concentrated under reduced pressure into soluble solid content Brix
55%, ethanol is reclaimed, concentrate is spray-dried to be made powdered black rice anthocyanin, and anthocyanidin content is 33.2% after testing, agriculture
Medicine does not detect.
Embodiment 2
（1）Black rice extracts：The black rice raw material that is produced from somewhere is taken, after testing wherein Isoprothiolane content 0.83mg/100kg, agriculture
Medicine total content 1.1mg/100kg, first add raw material weight 8%, the aqueous citric acid solution that mass fraction is 52%, be supplemented pure water
It is 1 to solid-liquid ratio:2.5, after extraction 8 hours, coarse filtration, centrifugation respectively, centrifugate is again using aperture as 0.5 micron of ceramic membrane mistake
Filter, obtains filtrate；
（2）Purifying：Above-mentioned filtrate is added into AB-8 type macroporous resin columns, upper prop flow control is in 1.0BV/h, then uses
The ethanol water that mass fraction is 55% elutes, and elution volume 8BV, collects eluent, is concentrated into soluble solid content
Brix 40%；
（3）Extraction：Concentrate is diluted to soluble solid content Brix 15% with pure water, uses the volume of concentrate
1.2 times of petroleum ether extraction 2 times, remains of pesticide enter in the petroleum ether extraction liquid of upper strata, and lower floor's solution is concentrated into solubility
Solid content Brix 37%；
（4）Silica gel column chromatography：By step（3）Silica gel column chromatography on the concentrate of gained, silica gel dosage are the 0.6 of concentrate
Times；First eluted with ethyl acetate, the agricultural chemicals for making to remain in concentrate, which is dissolved in ethyl acetate, further to be removed, and elution volume is
2.5BV；Again with 45% ethanol elution, elution volume 3BV, ethanol eluate is collected；
（5）Dry：By step（4）Resulting ethanol eluate is concentrated under reduced pressure into soluble solid content Brix
53%, ethanol is reclaimed, concentrate is spray-dried to be made powdered black rice anthocyanin, and anthocyanidin content is 31.8% after testing, agriculture
Medicine does not detect.
Embodiment 3
（1）Black rice extracts：The black rice raw material that is produced from somewhere is taken, after testing wherein Isoprothiolane content 0.75mg/100kg, agriculture
Medicine total content 0.97mg/100kg, first add raw material weight 7%, the aqueous citric acid solution that mass fraction is 55%, be supplemented pure
Water to solid-liquid ratio is 1:2.3, after extraction 9 hours, coarse filtration, centrifugation respectively, centrifugate is again using aperture as 0.5 micron of ceramic membrane mistake
Filter, obtains filtrate；
（2）Purifying：Above-mentioned filtrate is added into AB-8 type macroporous resin columns, upper prop flow control is in 1.2BV/h, then uses
The ethanol water that mass fraction is 52% elutes, and elution volume 6BV, collects eluent, is concentrated into soluble solid content
Brix 35%；
（3）Extraction：Concentrate is diluted to soluble solid content Brix 10% with pure water, uses the volume of concentrate
1.3 times of petroleum ether extraction 1 time, remains of pesticide enter in the petroleum ether extraction liquid of upper strata, and lower floor's solution is concentrated into solubility
Solid content Brix 34%；
（4）Silica gel column chromatography：By step（3）Silica gel column chromatography on the concentrate of gained, silica gel dosage are the 1 of concentrate
Times；First eluted with ethyl acetate, the agricultural chemicals for making to remain in concentrate, which is dissolved in ethyl acetate, further to be removed, and elution volume is
2.5BV；Again with 48% ethanol elution, elution volume 2.5BV, ethanol eluate is collected；
（5）Dry：By step（4）Resulting ethanol eluate is concentrated under reduced pressure into soluble solid content Brix
52%, ethanol is reclaimed, concentrate is spray-dried to be made powdered black rice anthocyanin, and anthocyanidin content is 32.3% after testing, agriculture
Medicine does not detect.
Table 1 is comparative example 1 and each step specific experiment results of embodiment 1-3
It can be seen that from the experimental data of upper table and purified only with macroporous resin adsorption, without petroleum ether extraction and silica gel
Column chromatography steps, it is impossible to reduce or remove the remains of pesticide in feed liquid.And experimental data is shown, embodiment 1 be the present invention most
Good embodiment, residues of pesticides are not detected in resulting black rice anthocyanin, while product purity highest, anthocyanidin content reach
33.2%。
Claims (4)
1. extraction purification prepares the process of non agricultural chemical residuum anthocyanidin from black rice, comprise the following steps：
（1）Black rice extracts：Black rice raw material is taken, it is water-soluble for 50-60% citric acid first to add raw material weight 5%-9%, mass fraction
Liquid, it is 1 to be supplemented pure water to solid-liquid ratio:2-1:3, after extracting 8-10 hours, coarse filtration, centrifugation respectively, centrifugate is again with aperture
For 0.5 micron of ceramic membrane filter, filtrate is obtained；
（2）Purifying：Above-mentioned filtrate is added into macroporous resin column, upper prop flow control divides in 0.8-1.2BV/h, then with quality
Number elutes for 40-60% ethanol water, elution volume 6-8BV, collects eluent, is concentrated into soluble solid content
Brix 30%-40%, obtain concentrate；
（3）Extraction：Gained concentrate is diluted to soluble solid content Brix 10%-20% with pure water, uses concentrated liquid
The petroleum ether extraction of 1-2 times of product 1-2 times, remains of pesticide enter in the petroleum ether extraction liquid of upper strata, and lower floor's solution is concentrated into can
Dissolubility solid content Brix 30-40%, concentrate after must extracting；
（4）Silica gel column chromatography：By step（3）Silica gel column chromatography on concentrate after the extraction of gained, silica gel dosage are concentrate
0.5-1 times；First eluted with ethyl acetate, the agricultural chemicals for making to remain in concentrate, which is dissolved in ethyl acetate, further to be removed, elution
Volume is 2-3BV；40-60% ethanol elutions are used again, elution volume 2-3BV, collect ethanol eluate；
（5）Dry：By step（4）Resulting ethanol eluate is concentrated under reduced pressure into soluble solid content Brix 50%-
60%, ethanol is reclaimed, concentrate is spray-dried to be made powdered black rice anthocyanin, and anthocyanidin content is more than 30% after testing, agriculture
Medicine does not detect.
2. the extraction purification according to claim 1 from black rice prepares the process of non agricultural chemical residuum anthocyanidin, it is special
Sign is：Described aqueous citric acid solution mass fraction is 57%.
3. the extraction purification according to claim 1 from black rice prepares the process of non agricultural chemical residuum anthocyanidin, it is special
Sign is：Macroreticular resin used is AB-8 type macroreticular resins.
4. the extraction purification according to claim 1 from black rice prepares the process of non agricultural chemical residuum anthocyanidin, it is special
Sign is：Step（4）Middle used silica gel dosage is 0.8 times of concentrate.
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| CN108419971A (en) * | 2018-02-02 | 2018-08-21 | 安徽金太阳食品有限公司 | A kind of processing method of rice underflow |
| CN110302559A (en) * | 2019-05-23 | 2019-10-08 | 朱法科 | The remaining minimizing technology of pesticide in Chinese nettle extract |
| CN113262274B (en) * | 2021-05-13 | 2022-05-03 | 华中农业大学 | Black rice extract and preparation method and application thereof |
| CN114230543B (en) * | 2022-01-12 | 2023-12-19 | 万华化学集团股份有限公司 | Method for extracting anthocyanin from Arabidopsis petals |
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| CA2857368C (en) * | 2011-12-16 | 2015-09-08 | Centre De Recherche Industrielle Du Quebec | Method for extracting anthocyanin derivatives from a plant source |
| CN102698466B (en) * | 2012-06-13 | 2015-11-25 | 晨光生物科技集团股份有限公司 | Remove the method for natural extract Pesticide Residues |
| CN104945365A (en) * | 2015-06-03 | 2015-09-30 | 陈玲华 | Technology for extracting anthocyanidin from black rice |
| CN105315253A (en) * | 2015-10-21 | 2016-02-10 | 安徽尚善生物科技股份有限公司 | Method for producing pesticide-residue-free black rice anthocyanidin with black rice bran |
| CN105331142A (en) * | 2015-11-10 | 2016-02-17 | 天津市尖峰天然产物研究开发有限公司 | Method for eliminating pesticide residues in anthocyanin type natural pigment |
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