CN111317136A - Preparation method and application of highland barley product - Google Patents
Preparation method and application of highland barley product Download PDFInfo
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- CN111317136A CN111317136A CN202010187923.8A CN202010187923A CN111317136A CN 111317136 A CN111317136 A CN 111317136A CN 202010187923 A CN202010187923 A CN 202010187923A CN 111317136 A CN111317136 A CN 111317136A
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Images
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
The invention discloses a preparation method of a highland barley product rich in anthocyanin, which comprises the following steps: pulverizing semen Avenae Nudae, adding acid-containing alcohol solution, ultrasonic extracting, filtering the extractive solution with ceramic membrane to remove impurities, and freeze drying the filtrate to obtain semen Avenae Nudae product. The preparation method of the highland barley product has the advantages of short time, high efficiency, good stability and low energy consumption. The highland barley products prepared by the method have the anthocyanin content as high as 50 percent and rich types of anthocyanins, and comprise cyanidin-3-O-glucoside, cyanidin-3-O- (3 '-O-malonyl-glucose), cyanidin-3-O- (6' -O-malonyl-glucose), cyanidin-3-O-bismalonyl-glucose, pelargonidin-3-O-bismalonyl-glucose and paeoniflorin-3-O-bismalonyl-glucose through analysis.
Description
Technical Field
The invention particularly relates to a preparation method and application of a highland barley product.
Background
Highland barley (also called naked barley) is a special type of barley, which has higher nutritional ingredients than rice, wheat and corn and is a crop used for both food, feed, brewing and medicine. In grain crops, highland barley has the characteristics of high protein, high fiber, high vitamin, low fat, low sugar and the like.
Anthocyanins are water-soluble natural pigments widely existing in plants, belong to flavonoid compounds, and mostly exist in the form of glucoside, also called anthocyanin. The highland barley anthocyanin belongs to water-soluble anthocyanin, is safe and nontoxic, has strong effects of eliminating in-vivo free radicals and resisting oxidation, and has the functions of delaying senility, enhancing immunity, tonifying qi and kidney, protecting cardiovascular and the like. Therefore, the highland barley rich in anthocyanin has great development and application prospects.
At present, the research on anthocyanin of highland barley is in a starting stage, the anthocyanin is extracted by hot reflux, the method is long in time and low in efficiency, the anthocyanin is easily lost due to improper temperature control, and the highland barley extraction process usually focuses on the content of the anthocyanin and ignores the variety of the anthocyanin.
Disclosure of Invention
In order to solve the problems, the invention provides a preparation method of a highland barley product rich in anthocyanin, which comprises the following steps:
pulverizing semen Avenae Nudae, adding acid-containing alcohol solution, ultrasonic extracting, filtering the extractive solution with ceramic membrane to remove impurities, and freeze drying the filtrate to obtain semen Avenae Nudae product.
Further, the mass volume ratio of the highland barley to the acid-containing ethanol solution is 1 g: 5-25 ml.
Further, the concentration of the acid in the acid-containing alcohol solution is 5-10% (ml/ml), preferably 5% (ml/ml).
Further, the acid-containing alcohol solution is an acetic acid ethanol solution, a formic acid ethanol solution, an acetic acid methanol solution or a formic acid methanol solution.
Furthermore, the highland barley variety is purple highland barley, black highland barley or blue highland barley.
Furthermore, the ultrasonic extraction is carried out in a dark place, the ultrasonic extraction time is 5-60 min, the power is 500 + 2500w, and the preferable ultrasonic extraction time is 30min and the power is 2000 w.
Further, the aperture of the ceramic membrane is 0.2um or 0.1 um.
Further, the freeze drying parameters are cold trap-50 ℃, temperature 45 ℃ and vacuum degree 20 pa.
The invention also provides a highland barley product prepared by the method, wherein the product contains more than 50% of anthocyanin; the anthocyanidin is cyanidin-3-O-glucoside (cyanidin-3-glucoside), cyanidin-3-O- (3 '-O-malonyl-glucose) (cyanidin 3-O- (3' -O-malonyl-glucoside)), cyanidin-3-O- (6 '-O-malonyl-glucose) (cyanidin 3-O- (6' -O-malonyl-glucose)), cyanidin-3-O-bismalonyl-glucose (cyanidin 3-O-diamonylglucoside), pelargonidin-3-O-bismalonyl-glucose (larpegonitin 3-O-diamonylglucoside), and peonidin-3-O-bismalonyl-glucose (paeonidin 3-O-diamonylglucoside).
Further, the antioxidant index of the product is more than 5000 mu mol TE/g.
The invention finally provides the application of the highland barley product in preparing food, medicine and/or cosmetics with oxidation resistance.
Further, the food is a functional food or a food additive, and the drug is a pharmaceutical intermediate.
The preparation method of the highland barley product rich in anthocyanin has the advantages of short time, high efficiency, good stability and low energy consumption. The highland barley product prepared by the method has the anthocyanin content of more than 50 percent, is rich in anthocyanin species and has remarkable antioxidation, and contains cyanidin-3-O-glucoside (cyanidin-3-glucoside), cyanidin-3-O- (3 '-O-malonyl-glucose) (cyanidin 3-O- (3' -O-malonyl-glucoside)), cyanidin-3-O- (6 '-O-malonyl-glucose) (cyanidin 3-O- (6' -O-malonyl-glucose)), cyanidin-3-O-malonyl-glucose (cyanidin 3-O-malonyl-glucose)), pelargonium-3-O-bispropionyl-glucose (pelargonium 3-O-bispropionic acid)), and cyanidin-3-O- dimalonylglucoside), paeoniflorin-3-O-bismalonyl-glucose (paeonidin 3-O-dimalonylglucoside).
Obviously, many modifications, substitutions, and variations are possible in light of the above teachings of the invention, without departing from the basic technical spirit of the invention, as defined by the following claims.
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Drawings
FIG. 1 liquid chromatogram of highland barley product
FIG. 2 Primary and Secondary mass spectra of anthocyanins (1. cyanidin-3-O-glucoside, 2. cyanidin-3-O- (3 '-O-malonyl-glucose), 3. cyanidin-3-O- (6' -O-malonyl-glucose), 4. cyanidin-3-O-bismalonyl-glucose, 5. pelargonidin-3-O-bismalonyl-glucose, 6. Paeonicin-3-O-bismalonyl-glucose)
FIG. 3 the results for the compounds in the highland barley product are given by the formula (1. cyanidin-3-O-glucoside, 2. cyanidin-3-O- (3 '-O-malonyl-glucose), 3. cyanidin-3-O- (6' -O-malonyl-glucose), 4. cyanidin-3-O-bismalonyl-glucose, 5. pelargonidin-3-O-bismalonyl-glucose, 6. peonidin-3-O-bismalonyl-glucose)
Detailed Description
Example 1 preparation of highland barley product of the invention
Taking 200g of highland barley, adding 2000ml of 5% (ml/ml) acetic acid ethanol solution, carrying out ultrasonic extraction under the condition of keeping out of the sun, extracting for 30min with the ultrasonic power of 2000w, filtering the extracting solution by using a 0.2um ceramic membrane to remove impurities after the ultrasonic extraction is finished, collecting filtrate, carrying out freeze drying on the filtrate under the conditions of a cold trap temperature of-50 ℃, a temperature of 45 ℃ and a vacuum degree of 20pa, and drying to obtain 20g of highland barley product rich in anthocyanin.
Example 2 preparation of highland barley product of the invention
Taking 500g of highland barley, adding 5000ml of 10% (ml/ml) acetic acid methanol solution, carrying out ultrasonic extraction under the condition of keeping out of the sun, extracting for 45min with the ultrasonic power of 1000w, filtering the extracting solution by using a 0.1um ceramic membrane to remove impurities after the ultrasonic extraction is finished, collecting filtrate, carrying out freeze drying on the filtrate under the conditions of a cold trap temperature of-50 ℃, a temperature of 45 ℃ and a vacuum degree of 20pa, and drying to obtain 520g of highland barley product rich in anthocyanin.
Example 3 preparation of highland barley product of the invention
Taking 20kg of highland barley, adding 200L of 5% (ml/ml) formic acid ethanol solution, carrying out ultrasonic extraction under the condition of keeping out of the sun for 60min, wherein the ultrasonic power is 500w, filtering an extracting solution by using a 0.2um ceramic membrane to remove impurities after the ultrasonic extraction is finished, collecting filtrate, carrying out freeze drying on the filtrate under the conditions of a cold trap temperature of-50 ℃, a temperature of 45 ℃ and a vacuum degree of 20pa, and drying to obtain 2020g of highland barley product rich in anthocyanin.
Example 4 preparation of highland barley product of the invention
Taking 200g of highland barley, adding 2000ml of 5% (ml/ml) methanoic acid solution, carrying out ultrasonic extraction under the condition of keeping out of the sun for 30min, wherein the ultrasonic power is 2000w, filtering an extracting solution by using a 0.2um ceramic membrane to remove impurities after the ultrasonic extraction is finished, collecting filtrate, carrying out freeze drying on the filtrate under the conditions of a cold well of-50 ℃, the temperature of 45 ℃ and the vacuum degree of 20pa, and drying to obtain 21g of highland barley product rich in anthocyanin.
The advantageous effects of the present invention are described below by way of test examples.
Test example 1 qualitative and quantitative analysis of anthocyanin in highland barley product of the present invention
1. Instruments and reagents
The instrument comprises the following steps: UPLC-Triple-TOF/MS system: AcquisytTM ultra model high performance liquid chromatograph (Waters, USA), Triple TOF 5600+ time-of-flight mass spectrometer, equipped with electrospray ion source (AB SCIEX, USA); one in ten thousand balance (mettler corporation, usa).
Reagent: chromatographic methanol (Yuwang reagent), mass spectrometric grade acetonitrile (Merck, USA).
2. Method of producing a composite material
1) Preparation of test solution
Taking the highland barley product prepared in the embodiment 1, taking 0.2ml of highland barley product, adding 5% acetic alcohol, carrying out ultrasonic extraction for 20min (keeping out of the sun), and filtering the solution through a filter membrane with the diameter of 0.22 mu m to obtain the highland barley.
2) Preparation of control solutions
Collecting cyanidin-3-O-glucoside 2mg, dissolving with methanol to obtain solution with concentration of 0.2mg/ml, and using as control solution.
3) Liquid phase conditions
Mobile phase: a: 0.1% aqueous formic acid solution B: 0.1% formic acid acetonitrile; flow rate: detection wavelength of 0.8 mL/min: 525 nm; a chromatographic column: ZoRBAX-SB C18(100mm × 4.6.6 mm i.d.,1.8 μm), a sample injection of 2 μ L, a column oven of 30 deg.C, and a gradient elution procedure of 0-10min, 12% B-12% B, 10-25min, and 15% B-25% B.
4) Conditions of Mass Spectrometry
A positive ion scanning mode; scanning range: m/z 100-1500; atomizing Gas (GS)1): 50 psi; atomizing Gas (GS)2): 50 psi; air curtain gas (CUR): 35 psi; ion source Temperature (TEM): 550 ℃; ion source voltage (IS): -4500V; primary scanning: declustering voltage (DP): 100V; focus voltage (CE): 10V; secondary scanning: and (3) acquiring mass spectrum data by using a TOF MS-Product Ion-IDA mode, wherein the CID energy is 20, 40 and 60V, and before sample injection, a CDS (compact disc) pump is used for mass axis correction to ensure that the mass axis error is less than 2 ppm.
3. Results
The liquid chromatogram of the highland barley product is shown in figure 1, and the secondary mass spectrum of each compound is shown in figure 2.
As can be seen from the figure 1, the highland barley product contains 6 components, and mass spectrum fragments of the 6 components are analyzed and identified to obtain: 1) cyanidin-3-O-glucoside (cyanidin-3-glucoside), 2) cyanidin-3-O- (3 '-O-malonyl-glucose) (cyanidin 3-O- (3' -O-malonyl-glucose)), 3) cyanidin-3-O- (6 '-O-malonyl-glucose) (cyanidin 3-O- (6' -O-malonyl-glucose)), 4) cyanidin-3-O-bismalonyl-glucose (cyanidin 3-O-diamonylglucoside), 5) pelargonidin-3-O-bismalonyl-glucose (pelargonidin 3-O-diamonylglucoside), 6) Paeonidin-3-O-bismalonyl-glucose (paeonidin 3-O-dimalonglucoside). The structural formula of the compounds 1-6 is shown in figure 3.
The content of cyanidin-3-O-glucoside in the highland barley product is calculated by an external standard method, the content of other cyanidin is determined by a semi-quantitative method, the content of 6 components of the cyanidin is shown in table 1, and the content sum of the cyanidin in the highland barley product is more than 50% and the variety is rich as shown in table 1.
TABLE 1 results of contents of 6 components of anthocyanins in highland barley products
| Compound (I) | Content (%) |
| cyanidin-3-O-glucoside | 5.5 |
| cyanidin-3-O- (3' -O-malonyl-glucose | 6.3 |
| cyanidin-3-O- (6' -O-malonyl-glucose) | 18.9 |
| cyanidin-3-O-bismalonyl-glucose | 14.3 |
| Geraniol-3-O-bismalonyl-glucose | 6.2 |
| Paeonine-3-O-bis (malonyl) -glucose | 5.4 |
| Total amount of | 56.6 |
Test example 2 antioxidant Properties of highland barley product of the present invention
1. Sample to be tested
Highland barley product prepared as in example 1
2. The detection method comprises the following steps:
superoxide radical (ROO-) is an analogue of hydrogen peroxide radical (HOO-) and results from the replacement of the hydrogen atom in HOO-by an organic group, which is usually produced during oxidation of proteins and lipids, and which is also produced after neutrophils have been activated in inflammatory reactions associated with oxidative stress. ROO-is capable of disrupting cell membrane and protein structures and is therefore a causative agent of many diseases associated with lipid autoxidation and enzyme inactivation. Currently, there are studies showing that ROO-has a large relationship with angiogenesis during tumor growth.
The oxidation resistance test of the invention refers to the test method of Huang D.J., Ou B., Hampsh-Woodril.M., Flanagan.J.A., and primer.R.high-throughput assay of oxidative gene radial interference probability (ORAC) using a multichannel linear amplification system coupled with an amino fluorescent reagent in 96-well format.journal of analytical and chemical chemistry.2002,50:4437-4444, which is based on the principle that ROO-destroys a fluorescent probe to change the fluorescence intensity, and tests the ROO-resistance of the sample to be tested. AAPH is used as a source for generating ROO-, fluorescein is used as a fluorescent probe, and vitamin E water-soluble analogue Trolox is used as a standard reference substance to carry out in-vitro ROO-resistance determination. The larger the area under the curve (AUC) in the "time-fluorescence signal plot", the stronger the ROO-resistance of the test sample. The method is suitable for evaluating the activity of water-soluble substances in plant extract, food, cosmetic, and medicine for resisting peroxide free radical.
3. And (3) detection results:
through detection, the oxidation resistance value of the highland barley product is 5000 mu mole TE/g, and the highland barley product has strong oxidation resistance.
Test example 3 screening by the Process of the present invention
1) Method of producing a composite material
Respectively taking highland barley, adding 5% (ml/ml) acetic acid ethanol solution, extracting by four modes of leaching, microwave extraction, hot reflux extraction and ultrasonic extraction, after extraction is finished, filtering an extracting solution by using a 0.2um ceramic membrane to remove impurities, collecting filtrate, freeze-drying the filtrate under the conditions of a cold trap-50 ℃, a temperature of 45 ℃ and a vacuum degree of 20pa, and drying to obtain the highland barley product. The specific extraction process conditions are shown in table 2.
TABLE 2 extraction Process conditions
2) Results
The anthocyanin content in the highland barley product is determined according to the method of the test example 1, the result is shown in the table 3, and the result can be seen from the table 3: the loss of anthocyanin in the highland barley product obtained by ultrasonic extraction with the power of 2000w is least within 30 min.
TABLE 3 anthocyanin content for different extraction processes
In conclusion, the preparation method of the highland barley product rich in anthocyanin has the advantages of short time, high efficiency, good stability and low energy consumption. The highland barley product prepared by the method has the anthocyanin content of more than 50 percent, is rich in anthocyanin varieties, has obvious antioxidation and has practical application and popularization values.
Claims (10)
1. A preparation method of highland barley products rich in anthocyanin is characterized by comprising the following steps: it comprises the following steps:
pulverizing semen Avenae Nudae, adding acid-containing alcohol solution, ultrasonic extracting, filtering the extractive solution with ceramic membrane to remove impurities, and freeze drying the filtrate to obtain semen Avenae Nudae product.
2. The method of claim 1, wherein: the mass volume ratio of the highland barley to the acid-containing alcoholic solution is 1 g: 5-25 ml.
3. The production method according to claim 1 or 2, characterized in that: the acid-containing alcohol solution is an acetic acid ethanol solution, a formic acid ethanol solution, an acetic acid methanol solution or a formic acid methanol solution, wherein the concentration of the acid is 5-10% (ml/ml), and preferably 5% (ml/ml).
4. The production method according to claim 1 or 2, characterized in that: the highland barley is purple highland barley, black highland barley or blue highland barley.
5. The method of claim 1, wherein: and (3) keeping the ultrasonic extraction away from light, wherein the ultrasonic extraction time is 5-60 min, the power is 500 + 2500w, and the ultrasonic extraction time is preferably 30min and the power is 2000 w.
6. The method of claim 1, wherein: the aperture of the ceramic membrane is 0.2um or 0.1 um; the freeze drying parameters are cold trap-50 ℃, temperature 45 ℃ and vacuum degree 20 pa.
7. The highland barley product prepared by the method of any one of claims 1 to 6, which is characterized in that: the content of anthocyanin in the highland barley product is more than 50 percent; the anthocyanidin is cyanidin-3-O-glucoside (cyanidin-3-glucoside), cyanidin-3-O- (3 '-O-malonyl-glucose) (cyanidin 3-O- (3' -O-malonyl-glucose)), cyanidin-3-O- (6 '-O-malonyl-glucose) (cyanidin 3-O- (6' -O-malonyl-glucose)), cyanidin-3-O-bismalonyl-glucose (cyanidin 3-O-diamonylglucoside), pelargonidin-3-O-bismalonyl-glucose (lapemidin-3-O-diamonylglucoside), and peonidin-3-O-bismalonyl-glucose (lapemidin-3-O-diamonylglucoside).
8. The highland barley product of claim 7, wherein: the oxidation resistance index of the highland barley product is more than 5000 mu mol TE/g.
9. Use of the highland barley product of claim 7 or 8 for the preparation of food, pharmaceutical and/or cosmetic products having antioxidant properties.
10. Use according to claim 9, characterized in that; the food is functional food or food additive, and the medicine is medicinal intermediate.
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| CN112138094A (en) * | 2020-09-09 | 2020-12-29 | 青海大学 | Highland barley and quinoa composition, preparation method and application thereof |
| CN114790460A (en) * | 2021-12-09 | 2022-07-26 | 西藏自治区农牧科学院农业研究所 | Highland barley cyanidin malonyl transferase gene and application thereof |
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| CN103432462A (en) * | 2013-09-05 | 2013-12-11 | 中国人民解放军军事医学科学院野战输血研究所 | Highland barley seed peel flavone, and preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112138094A (en) * | 2020-09-09 | 2020-12-29 | 青海大学 | Highland barley and quinoa composition, preparation method and application thereof |
| CN114790460A (en) * | 2021-12-09 | 2022-07-26 | 西藏自治区农牧科学院农业研究所 | Highland barley cyanidin malonyl transferase gene and application thereof |
| CN114790460B (en) * | 2021-12-09 | 2023-09-15 | 西藏自治区农牧科学院农业研究所 | Highland barley cyanidin malonyl transferase gene and application thereof |
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