CN106215010B - A kind of extracting method of highland barley polyphenol - Google Patents
A kind of extracting method of highland barley polyphenol Download PDFInfo
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Abstract
A kind of extracting method of highland barley polyphenol, is related to polyphenol extractive technique field, is completed by following steps: highland barley bran → removal lipid → extraction free phenol → release combination phenol → extraction → rotary evaporation → combine phenol extraction object；Therefore the beneficial effects of the present invention are: the present invention extracts the reference state phenolic substances in highland barley using acid system, test parameters is optimized, operating procedure is simplified, has obtained wide variety, rich content, and the highland barley reference state phenolic substances that antioxidant activity is high；The method operating procedure is relatively simple, and required time is short, and some researches show that the plants obtained using acid system and alkali process hydrolysis to combine the type of phenol and content significantly different, and the former total phenol content and oxidation resistance are higher than the latter.
Description
One, technical field
The present invention relates to polyphenol extractive technique fields, more particularly to a kind of extracting method of highland barley polyphenol.
Two, background technique
Polyphenol substance is the compound that the one kind being widely present in nature contains multiple phenolic hydroxyl structures, mainly includes
The substances such as flavonoids, phenolic acid, tannin have very strong inoxidizability and antiradical activities, can hinder oxide destruction lipid
And low-density lipoprotein, inhibit platelet aggregation, reduces the disease incidence of coronary heart disease and cancer, delay the function such as tissue and human senility
Effect, is good antioxidant；Vegetables and fruit are the sources of mankind's polyphenol substance, however it is more studies have shown that
Cereal preparation is also the important sources of phenolic substances.Modern popular disease is studies have shown that edible kernel grains or Related product pair
Reducing the chronic diseases such as cardiovascular and cerebrovascular has good effect, is primarily due to the effect of the polyphenols in kernel grains.
Polyphenol is also the intermediate product of secondary metabolism in cereal body, mainly includes benzoic acid, cinnamic acid, anthocyanidin, quinone, Huang
Ketone, chalcone, flavonols, flavones alkane and amino compound of phenolic acid and its derivative.Also contain tocotrienols, life in cereal
Phenol, ferulic acid etc. are educated, and content is little in vegetables and fruit.Polyphenol substance is generally with free state, the shape of esterification state and reference state
Formula is present in cereal body, and wherein free state and esterification state are referred to as soluble phenols, and reference state is referred to as insoluble phenols, with
The forms such as ester bond, glycosidic bond, ether glycosidic bond are combined with other substances (including protein, monosaccharide, organic acid etc.), more in cereal
The phenol overwhelming majority exists with combining form.These phenolic substancess cannot be extracted by conventional extraction method, be given
Inconvenience is brought in conjunction with the research of phenol, or even is ignored；But these combine phenol that can slowly be digested by gastrointestinal tract up to colon, together
When release a large amount of polyphenol substance；Andreasen etc. confirm small white mouse faecal flora can by cereal chaff skin Ah
Wei's acid releases；Adom etc. reports that the polyphenol substance in cereal has stronger oxidation resistance, and flavones also has potentially
Oxidation resistance and anti-cancer ability.
Highland barley is the staple food crop for the high and cold farming region in Qinghai-Tibet Platean being harvested for one time each year, and Qinghai-Tibet most characteristic
Crops, 80% or so Tibetan (total population about 5,400,000) born of the same parents is using highland barley as staple food.It is green as the big crop in small ancestor's grain
The broad covered area of highland barley, accounts for 60% or more and total output of grain of Qinghai-Tibet cereal crops area by about 380,000 hectares of total sown area
58-60%.Containing there are many phenolic compounds, such as tocol, flavones, anthocyanidin substance in highland barley.And the phenolic material in barley
The content (0.2%-0.4%) of matter is much higher than other cereal.But since the phenolic substances in barley is difficult to separate, grope one
The extracting method of phenolic substances in kind highland barley, forms the functional component of further investigation highland barley, specifies the anti-of highland barley phenolic substances
Oxidation etc. is of great significance.
Currently, the extracting method about cereal phenolic substances is more, but it is only limitted to free state mostly, and phenolic substances is in paddy
There are 3 kinds of free state, soluble reference state and insoluble reference state forms in object, and most of is all reference state；Wherein only swim
Amorph can be extracted by organic solvent, reference state usually with macromolecular substances such as ehter bond and ester bond and plant polyose, protein in conjunction with,
Being cannot be extracted by water or organic solvent；If the extraction for only focusing on free phenol can lose and most make it in conjunction with phenol
Antioxidation declines to a great extent, therefore is of great significance to the extraction of reference state phenolic substances in highland barley.
Mainly have alkaline process in conjunction with the extracting method of phenol at present, mostly use sodium hydroxide solution and acid system mostly use hydrochloric acid,
Sulfuric acid solution, wherein alkaline process is the most commonly used, but the obtained type of lichee combination phenol of Soviet Union and Eastern Europe's dawn discovery acid system and alkali process hydrolysis and
Content is significantly different, and the former total binding phenol content and oxidation resistance are higher than the latter；Arranze etc. is with wheat
Raw material, which extracts, combines phenol also to obtain similar conclusion；Therefore, it is badly in need of combining the Extraction solvent of phenol to be determined highland barley, preparation process
It optimizes and improves, realize that highland barley combines efficiently separating for phenol, be the functional characteristic of thoroughly evaluating difference grain color highland barley polyphenol
And its application lays the foundation.
Three, summary of the invention
In order to overcome the above-mentioned deficiencies of the prior art, the present invention provides a kind of extracting methods of highland barley polyphenol: its by with
Lower step is completed: highland barley bran → removal lipid → extraction free phenol → release combination phenol → extraction → rotary evaporation → combine phenol
Extract；
Remove the processing step of lipid process are as follows: elute spare highland barley bran petroleum ether 3~4 times, after elution
Highland barley bran it is spare；
Extract the processing step of free phenol process are as follows: accurately weigh 10 g of highland barley bran spare after removing lipid, highland barley
The acetone soln that wheat bran and concentration are 80% be mixed and stirred for uniformly, then in 25 DEG C of items according to 1:20~25g/mL ratio
400W ultrasonication 30min is used under part, then is centrifuged, and the revolving speed of centrifuge is 4000r/min, centrifugation time 10min, centrifugation
Supernatant, as free phenol extract are collected after the completion, and residue is extracted twice with same method, merges the supernatant of collection, is passed through
Extract is settled to 100mL with absolute methanol solution to doing by 40~45 DEG C of revolvings, measures total phenol content with Forint phenol method, residual
Slag is spare；
Release combines the processing step of phenol process are as follows: above-mentioned spare residue is added to the first that 17mL concentration is 10~12%
In alcohol sulfuric acid solution, water-bath 1 hour under the conditions of 75 DEG C does not adjust pH, solution for standby；
The processing step of extraction process are as follows: 20mL anhydrous ethyl acetate extraction 5 times is added in above-mentioned stock solution, every time
Obtained extract liquor centrifuge centrifuging and taking supernatant, the revolving speed of centrifuge are 2000-3000r/min, centrifugation time 5-
8min, the supernatant merging that 5 centrifugations are obtained are simultaneously spare；
In conjunction with the processing step of phenol extraction object process are as follows: by above-mentioned spare combined ethyl acetate extraction phase at 40~45 DEG C
Under the conditions of rotary evaporated to dryness, 0.45 μm of organic membrane filter of constant volume solution obtains highland barley by residue methanol constant volume to 10mL
Reference state phenolic substances extracting solution, -20 DEG C are kept in dark place；Total phenol content is measured with Forint phenol method.
The beneficial effects of the present invention are: therefore the present invention proposes the reference state phenolic substances in highland barley using acid system
It takes, optimizes test parameters, simplify operating procedure, obtained the high highland barley of wide variety, rich content, and antioxidant activity
Reference state phenolic substances；The method operating procedure is relatively simple, and required time is short, and some researches show that use acid system and alkaline process water
The plant that solution obtains combines the type of phenol and content significantly different, and the former total phenol content and oxidation resistance are than rear
Person is high.
Four, specific embodiment
Embodiment 1
The extracting method of polyphenol, concrete operations are as follows in black highland barley:
Black highland barley wheat bran 10g is accurately weighed, is the acetone soln that 250mL80% is added in 1:25 ratio according to solid-liquid ratio, through filling
Divide and be uniformly mixed, under the conditions of room temperature (25 DEG C), with 400W ultrasonication 30min, is centrifuged (4000r/min, 10min), collects
Supernatant.Residue is extracted 2 times with same method, merges the supernatant of 3 centrifugations, for 45 DEG C of revolvings to doing, residue is spare.It will extract
Object is settled to 100mL with absolute methanol solution, and the polyphenol content that dissociates after measured, in black highland barley wheat bran is 273.94 mg/100g,
DPPH free radical scavenging ability is 1897.95 μm of ol/100g, and ferrous ion reducing power is 2246.10 μm of ol/100g,
ABTS+ free radical scavenging ability is 5080.98 μm of ol/100g.By above-mentioned residue be added 17mL10%(mass concentration) first
Alcohol sulfuric acid solution, water-bath 1h at 75 DEG C, does not adjust pH.Then 20mL ethyl acetate is added to extract 5 times, centrifugation (3000r/min,
5min), combined ethyl acetate extraction phase.Extract liquor rotary evaporated to dryness under the conditions of 45 DEG C, residue with methanol constant volume extremely
10mL, 0.45 μm of organic membrane filter obtain highland barley reference state phenolic substances extracting solution, and -20 DEG C are kept in dark place.Black highland barley bran after measured
Combination phenol content in skin is 187.74 mg/100g, and DPPH free radical scavenging ability is 6197.30 μm of ol/100g, ferrous
Ion reduction ability is 1288.13 μm of ol/100g, and ABTS+ free radical scavenging ability is 1073.77 μm of ol/100g.Pass through
The free polyphenol content of the highland barley that the present embodiment method is extracted is higher than traditional water extract method by 77.62%, in conjunction with phenol content than traditional
It is high by 47.32% that alkali extracts (sodium hydroxide solution) method.
Embodiment 2
The extracting method of purple highland barley polyphenol, concrete operations are as follows:
Purple highland barley bran 10g is accurately weighed, is the acetone soln that 200mL80% is added in 1:20 ratio according to solid-liquid ratio, through filling
Divide and be uniformly mixed, under the conditions of room temperature (25 DEG C), with 400W ultrasonication 30min, is centrifuged (4000r/min, 10min), collects
Supernatant.Residue is extracted 2 times with same method, merges the supernatant of 3 centrifugations, for 40 DEG C of revolvings to doing, residue is spare.It will extract
Object is settled to 100mL with absolute methanol solution, and the polyphenol content that dissociates after measured, in purple highland barley bran is 235.96 mg/100g,
DPPH free radical scavenging ability is 2284.47 μm of ol/100g, and ferrous ion reducing power is 2041.16 μm of ol/100g,
ABTS+ free radical scavenging ability is 5180.91 μm of ol/100g.By above-mentioned residue be added 17mL12%(mass concentration) first
Alcohol sulfuric acid solution, water-bath 1h at 75 DEG C, does not adjust pH.Then 20mL ethyl acetate is added to extract 5 times, centrifugation (2500r/min,
6min), combined ethyl acetate extraction phase.Extract liquor rotary evaporated to dryness under the conditions of 40 DEG C, residue with methanol constant volume extremely
10mL, 0.45 μm of organic membrane filter obtain highland barley reference state phenolic substances extracting solution, and -20 DEG C are kept in dark place.Purple highland barley bran after measured
Combination phenol content in skin is 172.97 mg/100g, and DPPH free radical scavenging ability is 6142.77 μm of ol/100g, ferrous
Ion reduction ability is 1266.95 μm of ol/100g, and ABTS+ free radical scavenging ability is 1049.48 μm of ol/100g.Pass through
The free polyphenol content of the highland barley that the present embodiment method is extracted is higher than traditional water extract method by 46.77%, in conjunction with phenol content than traditional
It is high by 60.02% that alkali extracts (sodium hydroxide solution) method.
Embodiment 3
The extracting method of blue highland barley polyphenol, concrete operations are as follows:
Blue highland barley bran 10g is accurately weighed, is the acetone soln that 220mL80% is added in 1:22 ratio according to solid-liquid ratio, through filling
Divide and be uniformly mixed, under the conditions of room temperature (25 DEG C), with 100Hz ultrasonication 30min, is centrifuged (4000r/min, 10min), collects
Supernatant.Residue is extracted 2 times with same method, merges the supernatant of 3 centrifugations, for 42 DEG C of revolvings to doing, residue is spare.It will extract
Object is settled to 100mL with absolute methanol solution, and the polyphenol content that dissociates after measured, in blue highland barley bran is 209.09 mg/100g,
DPPH free radical scavenging ability is 1469.50 μm of ol/100g, and ferrous ion reducing power is 1858.78 μm of ol/100g,
ABTS+ free radical scavenging ability is 4068.20 μm of ol/100g.By above-mentioned residue be added 17mL11%(mass concentration) first
Alcohol sulfuric acid solution, water-bath 1h at 75 DEG C, does not adjust pH.Then 20mL ethyl acetate is added to extract 5 times, centrifugation (2000r/min,
8min), combined ethyl acetate extraction phase.Extract liquor rotary evaporated to dryness under the conditions of 42 DEG C, residue with methanol constant volume extremely
10mL, 0.45 μm of organic membrane filter obtain highland barley reference state phenolic substances extracting solution, and -20 DEG C are kept in dark place.Blue highland barley bran after measured
Combination phenol content in skin is 216.41 mg/100g, and DPPH free radical scavenging ability is 6334.14 μm of ol/100g, ferrous
1603.50 μm of ol/100g of ion reduction ability, ABTS+ free radical scavenging ability are 1222.38 μm of ol/100g.Pass through this
The free polyphenol content of the highland barley that embodiment method is extracted is higher than traditional water extract method by 68.71%, in conjunction with phenol content than traditional alkali
(sodium hydroxide solution) method of extraction is high by 49.03%.
Embodiment 4
The extracting method of white highland barley polyphenol, concrete operations are as follows:
White highland barley bran 10g is accurately weighed, is the acetone soln that 200mL80% is added in 1:20 ratio according to solid-liquid ratio, through filling
Divide and be uniformly mixed, under the conditions of room temperature (25 DEG C), with 100Hz ultrasonication 30min, is centrifuged (4000r/min, 10min), collects
Supernatant.Residue is extracted 2 times with same method, merges the supernatant of 3 centrifugations, for 45 DEG C of revolvings to doing, residue is spare.It will extract
Object is settled to 100mL with absolute methanol solution, and the polyphenol content that dissociates after measured, in white highland barley bran is 269.06 mg/100g,
DPPH free radical scavenging ability is 1951.04 μm of ol/100g, and ferrous ion reducing power is 2286.04 μm of ol/100g,
ABTS+ free radical scavenging ability is 4935.80 μm of ol/100g.By above-mentioned residue be added 17mL12%(mass concentration) first
Alcohol sulfuric acid solution, water-bath 1h at 75 DEG C, does not adjust pH.Then 20mL ethyl acetate is added to extract 5 times, centrifugation (2000r/min,
8min), combined ethyl acetate extraction phase.Extract liquor rotary evaporated to dryness under the conditions of 45 DEG C, residue with methanol constant volume extremely
10mL, 0.45 μm of organic membrane filter obtain highland barley reference state phenolic substances extracting solution, and -20 DEG C are kept in dark place.White highland barley bran after measured
Combination phenol content in skin is 233.89 mg/100g, and DPPH free radical scavenging ability is 6547.60 μm of ol/100g, ferrous
Ion reduction ability is 1540.01 μm of ol/100g, and ABTS+ free radical scavenging ability is 1117.71 μm of ol/100g.Pass through
The free polyphenol content of the highland barley that the present embodiment method is extracted is higher than traditional water extract method by 67.98%, in conjunction with phenol content than traditional
It is high by 54.67% that alkali extracts (sodium hydroxide solution) method.
Embodiment 5
A kind of extracting method of highland barley polyphenol: it is completed by following steps: highland barley bran → removal lipid → extraction is free
Phenol → release combination phenol → extraction → rotary evaporation → combine phenol extraction object；
Remove the processing step of lipid process are as follows: elute spare highland barley bran petroleum ether 3 times, the blueness after eluting
Highland barley wheat bran is spare；
Extract the processing step of free phenol process are as follows: accurately weigh 10 g of highland barley bran spare after removing lipid, highland barley
The acetone soln that wheat bran and concentration are 80% be mixed and stirred for uniformly, then under the conditions of 25 DEG C according to 1:20g/mL ratio
It with 100Hz ultrasonication 30min, then is centrifuged, the revolving speed of centrifuge is 4000r/min, and centrifugation time 10min has been centrifuged
At rear collection supernatant, as free phenol extract, residue is extracted twice with same method, merges the supernatant of collection, through 40
Extract is settled to 100mL with absolute methanol solution, measures total phenol content with Forint phenol method, residue is spare to dry by DEG C revolving；
Release combines the processing step of phenol process are as follows: above-mentioned spare residue is added to the methanol sulphur that 17mL concentration is 10%
In acid solution, water-bath 1 hour under the conditions of 75 DEG C does not adjust pH, solution for standby；
The processing step of extraction process are as follows: 20mL anhydrous ethyl acetate extraction 5 times is added in above-mentioned stock solution, every time
The revolving speed of obtained extract liquor centrifuge centrifuging and taking supernatant, centrifuge is 3000r/min, centrifugation time 5min, by 5 times
Obtained supernatant is centrifuged to merge and spare；
In conjunction with the processing step of phenol extraction object process are as follows: by above-mentioned spare combined ethyl acetate extraction phase in 40 DEG C of conditions
0.45 μm of organic membrane filter of constant volume solution is obtained highland barley combination by lower rotary evaporated to dryness, residue methanol constant volume to 10mL
State phenolic substances extracting solution, -20 DEG C are kept in dark place；Total phenol content is measured with Forint phenol method.
Embodiment 6
A kind of extracting method of highland barley polyphenol: it is completed by following steps: highland barley bran → removal lipid → extraction is free
Phenol → release combination phenol → extraction → rotary evaporation → combine phenol extraction object；
Remove the processing step of lipid process are as follows: elute spare highland barley bran petroleum ether 4 times, the blueness after eluting
Highland barley wheat bran is spare；
Extract the processing step of free phenol process are as follows: accurately weigh 10 g of highland barley bran spare after removing lipid, highland barley
The acetone soln that wheat bran and concentration are 80% be mixed and stirred for uniformly, then under the conditions of 25 DEG C according to 1:25g/mL ratio
It with 100Hz ultrasonication 30min, then is centrifuged, the revolving speed of centrifuge is 4000r/min, and centrifugation time 10min has been centrifuged
At rear collection supernatant, as free phenol extract, residue is extracted twice with same method, merges the supernatant of collection, through 45
Extract is settled to 100mL with absolute methanol solution, measures total phenol content with Forint phenol method, residue is spare to dry by DEG C revolving；
Release combines the processing step of phenol process are as follows: above-mentioned spare residue is added to the methanol sulphur that 17mL concentration is 12%
In acid solution, water-bath 1 hour under the conditions of 75 DEG C does not adjust pH, solution for standby；
The processing step of extraction process are as follows: 20mL anhydrous ethyl acetate extraction 5 times is added in above-mentioned stock solution, every time
The revolving speed of obtained extract liquor centrifuge centrifuging and taking supernatant, centrifuge is 2000r/min, centrifugation time 8min, by 5 times
Obtained supernatant is centrifuged to merge and spare；
In conjunction with the processing step of phenol extraction object process are as follows: by above-mentioned spare combined ethyl acetate extraction phase in 45 DEG C of conditions
0.45 μm of organic membrane filter of constant volume solution is obtained highland barley combination by lower rotary evaporated to dryness, residue methanol constant volume to 10mL
State phenolic substances extracting solution, -20 DEG C are kept in dark place；Total phenol content is measured with Forint phenol method.
Claims (1)
1. a kind of extracting method of highland barley polyphenol: it is characterized by: it is completed by following steps: highland barley bran → removal lipid →
Extraction free phenol → release combination phenol → extraction → rotary evaporation → combine phenol extraction object；
Remove the processing step of lipid process are as follows: elute spare highland barley bran petroleum ether 3~4 times, the blueness after eluting
Highland barley wheat bran is spare；
Extract the processing step of free phenol process are as follows: accurately weigh 10 g of highland barley bran spare after removing lipid, highland barley bran
The acetone soln for being 80% with concentration be mixed and stirred for uniformly, then under the conditions of 25 DEG C according to 1:20~25g/mL ratio
It with 400W ultrasonication 30min, then is centrifuged, the revolving speed of centrifuge is 4000r/min, centrifugation time 10min, and centrifugation is completed
After collect supernatant, as free phenol extract, residue is extracted twice with same method, merge the supernatant of collection, through 40~
Extract is settled to 100mL with absolute methanol solution to doing by 45 DEG C of revolvings, measures total phenol content with Forint phenol method, residue is standby
With；
Release combines the processing step of phenol process are as follows: above-mentioned spare residue is added to the methanol sulphur that 17mL concentration is 10~12%
In acid solution, water-bath 1 hour under the conditions of 75 DEG C does not adjust pH, solution for standby；
The processing step of extraction process are as follows: 20mL anhydrous ethyl acetate is added in above-mentioned stock solution and extracts 5 times, obtains every time
Extract liquor centrifuge centrifuging and taking supernatant, the revolving speed of centrifuge is 2000~3000r/min, and centrifugation time is 5~8min,
Obtained supernatant will be centrifuged for 5 times to merge and spare；
In conjunction with the processing step of phenol extraction object process are as follows: by above-mentioned spare combined ethyl acetate extraction phase in 40~45 DEG C of conditions
0.45 μm of organic membrane filter of constant volume solution is obtained highland barley combination by lower rotary evaporated to dryness, residue methanol constant volume to 10mL
State phenolic substances extracting solution, -20 DEG C are kept in dark place；Total phenol content is measured with Forint phenol method.
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| CN105125742A (en) * | 2015-08-25 | 2015-12-09 | 华侨大学 | Method of extracting combination type phenolic compounds from camellia sinensis seed oil |
| CN107242567B (en) * | 2017-06-15 | 2020-07-14 | 西南大学 | Preparation method of morchella nigra dietary polyphenol |
| CN109805406B (en) * | 2019-02-19 | 2022-05-31 | 广东省农业科学院蚕业与农产品加工研究所 | Extraction method for ultrahigh pressure-alkali-acid hydrolysis step-by-step release of rice bran-bound phenol |
| CN111067033A (en) * | 2020-01-06 | 2020-04-28 | 青海大学 | Highland barley food rich in soluble phenols and preparation method thereof |
| CN113244657A (en) * | 2021-06-18 | 2021-08-13 | 四川省农业科学院农产品加工研究所 | Echelon extraction method of functional components of purple highland barley bran |
| CN113730951A (en) * | 2021-08-02 | 2021-12-03 | 江苏大学 | Subcritical water extraction method for improving antioxidant activity of sorghum bran combined-state polyphenol |
| CN116223412A (en) * | 2023-02-13 | 2023-06-06 | 西藏自治区农牧科学院农业研究所 | Method for detecting content of phenols in highland barley |
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| CN101617787A (en) * | 2009-07-27 | 2010-01-06 | 中国科学院西北高原生物研究所 | Process for continuously extracting a plurality of products from highland barley |
| CN104323251A (en) * | 2014-10-31 | 2015-02-04 | 云南农业大学 | Separation method of polyphenolic compounds in highland barley dietary fibers |
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