CN110002962B - Method for extracting alkyl resorcinol from wheat bran - Google Patents
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
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Abstract
The invention belongs to the field of separation and preparation of natural functional substances, and relates to a method for extracting alkyl resorcinol from wheat bran. The invention selects dry wheat bran as raw material, selects, finishes and grinds the raw material, adds ethyl acetate to carry out ultrasonic extraction, obtains supernatant fluid after centrifugation, and obtains concentrated solution through rotary evaporation. Then, solid phase extraction or silica gel mixing sample is used for silica gel column chromatography for separation and purification, and then eluent is collected for further concentration, so that mixed liquor of different homologues of the alkyl resorcinol is obtained. Through high performance liquid chromatography analysis, different homologues in the alkylresorcinol product have the advantages of good separation degree, high purity and the like. Compared with the existing alkylresorcinol preparation technology, the alkylresorcinol naturally existing in the wheat bran is separated and purified by utilizing silica gel column chromatography, so that the complexity and the risk of chemical synthesis are greatly reduced, and the operability is strong.
Description
Technical Field
The invention relates to a method for extracting alkyl resorcinol from wheat bran, and belongs to the field of separation and purification of natural functional substances.
Background
Alkylresorcinol (C)Alkylresorcinols，ARs) Is 1, 3-resorcinol, an alkyl group containing an odd number of carbon atoms in the 5-position of the phenyl ringThe general term of a substituted derivative belongs to the class of phenolic lipids and has amphiphilicity. The ARs are distributed in the wheat grain cortex and are the main phenolic components in the wheat, and the total content range is 320-1010 mu g/g. ARs consist of several homologues, the alkyl side chains of which contain an odd number of carbon atoms (13-27), named C13: 0-C27: 0, the main components are C19: 0 and C21: 0. ARs are important biomarkers for judging whole wheat flour by the current food industry standard (LS/T3244-2015), and are also one of important components of the whole wheat flour. Research shows that ARs have certain functional characteristics, such as cancer resistance, oxidation resistance, enzyme activity inhibition, wound healing promotion and the like, and have certain improvement effect on various chronic diseases. Therefore, ARs are receiving increasing attention and attention.
China is a world large country for wheat planting and consumption. The wheat bran, as a large byproduct of wheat milling, accounts for about 15% of the quality of wheat grains, and the annual output is up to 3000 ten thousand tons. Because of rich crude fiber content and rough and astringent taste, more than 85 percent of wheat bran is used in feed and fermentation industries, and few bran health-care foods come into the market, so the economic value is low. However, bran contains abundant dietary fibers, proteins, carbohydrates, vitamins, minerals and the like, and also contains a large amount of active natural antioxidant substances, such as: alkyl resorcinol, ferulic acid, phenolic acid and the like, which are byproducts with high nutritional value. The wheat bran has sufficient source and low price, so that the research strength on the wheat bran is increased, the wheat bran is utilized in a high-value mode, the comprehensive utilization rate is improved, and the method has important significance.
In recent research, ARs are used as biomarkers of wheat whole grains, but are still in the first stage in the wheat research of the whole grains in China, and few reports are made about the extraction method of the grain ARs and the preparation technology of the product. The study of ARs has the following problems: first, there is a lack of reasonably specified alkylresorcinol separation techniques, e.g., the ARs homologs heptadecylresorcinol and nonadecylresorcinol differ by only two-CH2Their polarities are close and difficult to separate; secondly, the alkyl resorcinol standard substance is expensive and has long shelf life, so that the research progress of the alkyl resorcinol is easily influenced; third, it was differentiated in the previous studyThe synthesis of the alkyl resorcinol is carried out in advance, but the synthesis process is complex, difficult to control and high in risk, further purification is needed in the later period, and the environment is at risk of secondary pollution. Aiming at the problems, the method for preparing the wheat bran alkylresorcinol standard substance is of great significance for further researching alkylresorcinol and application.
Disclosure of Invention
The invention aims to provide a method for extracting alkyl resorcinol from wheat bran and a product thereof, which can obtain pure products of different homologues of the alkyl resorcinol and can be used for detection, nutritional function activity, application and the like of the alkyl resorcinol.
The invention relates to a method for extracting alkyl resorcinol from wheat bran, which comprises the steps of taking an analytically pure ethyl acetate solution as an extraction solvent, and carrying out ultrasonic extraction on the wheat bran; concentrating the extractive solution with rotary evaporator, and subjecting to optimized silica gel column chromatography to obtain 7 kinds of alkylresorcinol homolog mixtures, including heptadecylresorcinol, nonadecenylresorcinol, nonadecylresorcinol, heneicosenylresorcinol, heneicosanylresorcinol, tricosanylresorcinol, and pentacosylresorcinol; and finally, measuring seven alkylresorcinol homologues by using high performance liquid chromatography. The method is realized by the following technical scheme:
(1) pretreatment of raw materials: removing broken stones, silt and insect particles from wheat harvested in the current year, cleaning and airing to obtain wheat bran, and grinding the wheat bran to 80 meshes by using a grinding machine;
(2) extraction: performing ultrasonic extraction on the wheat bran by using ethyl acetate as an extraction solvent, wherein the extraction time is 30 min and the extraction power is 300W;
(3) centrifuging: centrifuging at 3500 r/min for 10min to obtain sample supernatant;
(4) concentration: collecting supernatant obtained by centrifugation, and concentrating by using a rotary evaporator at the temperature of 45 ℃ to obtain an alkyl resorcinol ethyl acetate extract concentrated solution;
(5) separation and purification: the first method adopts silica gel column chromatography, and comprises activating silica gel powder in a 120 deg.C oven at high temperature for 30 min, and cooling in a drier to room temperature. Weighing the concentrated solution sample in the step (4) and silica gel powder according to the mass ratio of 1:1, pouring the concentrated solution sample into an evaporation dish for sample mixing, then placing the mixture into a 50 ℃ oven for drying, taking out the dried mixture, cooling the dried mixture to room temperature, uniformly stirring the mixture for later use, carrying out dry sample loading on silica gel column chromatography, and selecting eluent to wash the column for elution for separation and purification; and (5) adopting a solid phase extraction column, loading the concentrated solution obtained in the step (4) to the solid phase extraction column, and eluting by using an eluent to wash the column for separation and purification.
(6) And (3) re-concentration: collecting the eluent obtained in the step (5), performing rotary evaporation and concentration, and absorbing the elution concentrated solution;
(7) high performance liquid chromatography analysis: redissolving with 1 mL of methanol solution after nitrogen blowing, and detecting by high performance liquid chromatography after passing through an organic filter membrane of 0.22 mu m.
Preferably, the separation and purification conditions in step (5) are: silica gel column chromatography is adopted, and the mass ratio of the sample mixing mass to the silica gel powder in the silica gel column chromatography is 1: 10. The eluent is petroleum ether-ethyl acetate (v/v, 10: 1-1: 1).
The liquid chromatography conditions in the step (7) are as follows:
(1) mobile phase: phase A0.1% aqueous formic acid; phase B0.1% methanoic acid in methanol, flow rate: 1 mL/min, column temperature: 30 ℃, sample introduction: 10 muL;
(2) the mobile phase elution procedure was: 0min, 15-25% of phase A and 75-85% of phase B; 5min, 15-10% of phase A and 75-90% of phase B; 10min, 5-10% of phase A and 90-95% of phase B; 15min, 0-5% of phase A and 95-100% of phase B; 35min, 15-25% of phase A and 75-85% of phase B;
(3) a detector: the detection wavelength was 280 nm using a DAD detector.
The mixture of 7 alkyl resorcinols homologues extracted by the method is heptadecyl resorcinol, nonadecyl resorcinol, heneicosyl resorcinol, tricosyl resorcinol and pentacosyl resorcinol.
And (3) further carrying out semi-preparative liquid phase treatment on the alkyl resorcinol homolog mixture obtained by the extraction to separate five alkyl resorcinol monomers, namely heptadecyl resorcinol, nonadecyl resorcinol, heneicosyl resorcinol, tricosyl resorcinol and pentacosyl resorcinol.
The semi-preparative liquid chromatography conditions were:
(1) mobile phase: phase A0.1% aqueous formic acid; phase B0.1% methanoic acid in methanol, flow rate: 2 mL/min, column temperature: 30 ℃, sample introduction: 200 muL;
(2) the mobile phase elution procedure was: 0min, 15-25% of phase A and 75-85% of phase B; 5min, 15-10% of phase A and 75-90% of phase B; 10min, 5-10% of phase A and 90-95% of phase B; 15min, 0-5% of phase A and 95-100% of phase B; 35min, 15-25% of phase A and 75-85% of phase B;
(3) a detector: the detection wavelength was 280 nm using a DAD detector.
The invention has the following beneficial effects:
(1) the seven alkylresorcinol homologue mixtures extracted by the method are prepared into five alkylresorcinol monomers by a semi-preparative liquid phase, so that the wheat bran is fully utilized.
(2) According to the method, the silica gel column chromatography is constructed by selecting the customized glass column and the silica gel powder filled column, and the silica gel powder is low in price and high in utilization rate compared with other column fillers.
(3) The method of the invention selects the petroleum ether-ethyl acetate mixed solution as the eluent, and compared with the chloroform-ethyl ether mixed solution, the method has the advantages of lower toxicity and environmental protection.
Drawings
FIG. 1 is a liquid chromatogram of the alkylresorcinol ethyl acetate extract concentrate of example 1;
FIG. 2 is a liquid chromatogram of the product of example 1;
FIG. 3 is a liquid chromatogram of the product of comparative example 1;
FIG. 4 is a liquid chromatogram of the product of example 2;
FIG. 5 is a liquid chromatogram of the product of comparative example 2;
FIG. 6 is a chromatogram of a semi-prepared liquid phase product of example 3.
In the figure: 1-heptadecylresorcinol, 2-nonadecenylresorcinol, 3-nonadecylresorcinol, 4-heneicosenylresorcinol, 5-heneicosanylresorcinol, 6-tricosanylresorcinol, and 7-pentacosylresorcinol.
Detailed Description
The invention is further described below by means of specific examples.
Example 1
(1) Pretreatment of raw materials: removing broken stones, silt and insect particles from wheat harvested in the current year, cleaning and airing to obtain wheat bran, and grinding the wheat bran to 80 meshes by using a grinding machine;
(2) extraction: performing ultrasonic extraction on the wheat bran by using ethyl acetate as an extraction solvent, wherein the extraction time is 30 min and the extraction power is 300W;
(3) centrifuging: centrifuging at 3500 r/min for 10min to obtain sample supernatant;
(4) and (3) concentrating: collecting supernatant obtained by centrifugation, and concentrating by using a rotary evaporator at 45 ℃ to obtain an alkylresorcinol ethyl acetate extract concentrated solution;
(5) separation and purification: silica gel column chromatography is adopted, firstly, 100-200 meshes of silica gel powder is placed in a 120 ℃ oven for high-temperature activation for 30 min, and then the silica gel powder is placed in a dryer for cooling to room temperature. Weighing a concentrated solution sample with the same mass and silica gel powder, pouring the concentrated solution sample and the silica gel powder into an evaporating dish, uniformly stirring, putting the evaporating dish in an oven with the temperature of 50-60 ℃ for overnight drying, taking out, and cooling to room temperature for later use. A500 x 40 mm normal pressure glass chromatographic column is selected, and dry loading is adopted. Pouring the activated silica gel powder into a clean and dry chromatographic column, and slightly shaking the chromatographic column until the surface of the filler is flat, wherein the height of the packed column is 18 cm. Fixing the chromatographic column on an iron support, vertically placing until the plane of the filler does not sink any more, and lightly adding sample-mixing silica gel until the surface is smooth. The upper end of the chromatographic column should be left at a certain height for the accumulation of eluent. Performing gradient elution by using petroleum ether-ethyl acetate (v/v, 10: 1), performing rotary evaporation on each 100 mL of eluent, tracking by using TLC, combining the same components, analyzing by using HPLC, and collecting the eluent;
(6) and (3) re-concentration: collecting eluate, concentrating by rotary evaporation, and absorbing the concentrated eluate;
(7) high performance liquid chromatography analysis: redissolving with 1 mL of methanol solution after nitrogen blowing, and detecting by high performance liquid chromatography after passing through an organic filter membrane of 0.22 mu m.
The content of the alkylresorcinol homologues obtained under the above conditions is determined to be 95.20-97.81 mg/g, and the alkylresorcinol homologues comprises a mixture of 7 homologues, namely heptadecylresorcinol, nonadecylresorcinol, heneicosenylresorcinol, heneicosylresorcinol, tricosylresorcinol and pentacosylresorcinol. Compared with the concentrated solution obtained after the step (4) in the attached figure 1, the content of the alkylresorcinol in the concentrated solution is obviously improved by 39.88-42.17 mg/g.
Comparative example 1
(1) Pretreatment of raw materials: removing broken stones, silt and insect particles from wheat harvested in the current year, cleaning and airing to obtain wheat bran, and grinding the wheat bran to 80 meshes by using a grinding machine;
(2) extraction: performing ultrasonic extraction on the wheat bran by using ethyl acetate as an extraction solvent, wherein the extraction time is 30 min and the extraction power is 300W;
(3) centrifuging: centrifuging at 3500 r/min for 10min to obtain sample supernatant;
(4) concentration: collecting supernatant obtained by centrifugation, and concentrating by using a rotary evaporator at the temperature of 45 ℃ to obtain an alkyl resorcinol ethyl acetate extract concentrated solution;
(5) separation and purification: the same procedure as in example 1 was followed, except that a chloroform-ether elution system (v/v, 9: 1) was used for gradient elution, spin-evaporation was performed per 100 mL of the eluate, TLC was used for follow-up, the same fractions were combined, and the eluate was analyzed and collected by HPLC;
(6) and (3) re-concentration: collecting eluate, concentrating by rotary evaporation, and absorbing eluate concentrate;
(7) high performance liquid chromatography analysis: redissolving with 1 mL methanol solution after nitrogen blowing, and detecting with high performance liquid chromatography after passing through an organic filter membrane of 0.22 mu m.
The content of the alkylresorcinol homologues obtained under the above conditions is 69.28-73.65 mg/g, which is lower than that of the alkylresorcinol in example 1.
Example 2
(1) Pretreatment of raw materials: removing broken stones, silt and insect particles from wheat harvested in the current year, cleaning and airing to obtain wheat bran, and grinding the wheat bran to 80 meshes by using a grinding machine;
(2) extraction: performing ultrasonic extraction on the wheat bran by using ethyl acetate as an extraction solvent, wherein the extraction time is 30 min and the extraction power is 300W;
(3) centrifuging: centrifuging at 3500 r/min for 10min to obtain sample supernatant;
(4) concentration: collecting supernatant obtained by centrifugation, and concentrating by using a rotary evaporator at the temperature of 45 ℃ to obtain an alkyl resorcinol ethyl acetate extract concentrated solution;
(5) separation and purification: selecting a solid phase extraction column, firstly flushing the column with n-pentane to remove impurities and reduce the polarity of the solid phase extraction column, then loading the alkylresorcinol ethyl acetate extract concentrated solution to the solid phase extraction column, and eluting at the flow rate of 0.5 mL/min by using an automatic injector. Performing gradient elution by using petroleum ether-ethyl acetate (v/v, 1: 1), performing rotary evaporation on each 100 mL of eluent, tracking by using TLC, combining the same components, analyzing by using HPLC, and collecting the eluent;
(6) and (3) re-concentration: collecting eluate, concentrating by rotary evaporation, and absorbing the concentrated eluate;
(7) high performance liquid chromatography analysis: redissolving with 1 mL of methanol solution after nitrogen blowing, and detecting by high performance liquid chromatography after passing through an organic filter membrane of 0.22 mu m.
The content of the alkyl resorcinol obtained under the conditions is 76.43-80.26 mg/g, and is obviously improved compared with 39.88-42.17 mg/g of the alkyl resorcinol crude extract in the attached drawing 1.
Comparative example 2
(1) Pretreatment of raw materials: removing broken stones, silt and insect particles from wheat harvested in the current year, cleaning and airing to obtain wheat bran, and grinding the wheat bran to 80 meshes by using a grinding machine;
(2) extraction: performing ultrasonic extraction on the wheat bran by using ethyl acetate as an extraction solvent, wherein the extraction time is 30 min, and the extraction power is 300W;
(3) centrifuging: centrifuging at 3500 r/min for 10min to obtain sample supernatant;
(4) concentration: collecting supernatant obtained by centrifugation, and concentrating by using a rotary evaporator at 45 ℃ to obtain ethyl alkyl-m-phenylacetate extract concentrated solution;
(5) separation and purification: selecting a solid phase extraction column, firstly flushing the column with n-pentane to remove impurities and reduce the polarity of the solid phase extraction column, then loading the alkylresorcinol ethyl acetate extract concentrated solution to the solid phase extraction column, and eluting at the flow rate of 0.5 mL/min by using an automatic injector. Performing gradient elution by using a chloroform-ether elution system (v/v, 9: 1), performing rotary evaporation on each 100 mL of eluent, tracking by using TLC, combining the same components, analyzing by using HPLC and collecting the eluent;
(6) and (3) re-concentration: collecting the eluent, concentrating by rotary evaporation, and absorbing a certain volume of elution concentrated solution;
(7) high performance liquid chromatography analysis: redissolving with 1 mL methanol solution after nitrogen blowing, and detecting with high performance liquid chromatography after passing through an organic filter membrane of 0.22 mu m.
The content of the alkylresorcinol homologues obtained under the above conditions is 53.93-56.83 mg/g, which is lower than that of the alkylresorcinol in example 2.
Example 3
Comparing the separation and purification effects of the alkylresorcinols, the mixture obtained in example 1 has good separation degree and less impurities. The alkylresorcinol monomer was further prepared by semi-preparative liquid phase using the alkylresorcinol homologue mixture obtained in example 1.
The semi-preparative liquid chromatography conditions were:
(1) mobile phase: phase A0.1% aqueous formic acid; phase B0.1% methanoic acid in methanol, flow rate: 2 mL/min, column temperature: 30 ℃, sample introduction: 200 muL;
(2) the mobile phase elution procedure was: 0min, 15-25% of phase A and 75-85% of phase B; 5min, 15-10% of phase A and 75-90% of phase B; 10min, 5-10% of phase A and 90-95% of phase B; 15min, 0-5% of phase A and 95-100% of phase B; 35min, 15-25% of phase A and 75-85% of phase B;
(3) a detector: the detection wavelength was 280 nm using a DAD detector.
Under the above conditions, 5 monomers of alkylresorcinol were obtained, heptadecylresorcinol, nonadecylresorcinol, heneicosylresorcinol, tricosylresorcinol, and pentacosylresorcinol, respectively.
Claims (3)
1. The method for extracting the alkyl resorcinol from the wheat bran is characterized by comprising the following specific steps:
(1) pretreatment of raw materials: removing broken stones, silt and insect particles from wheat harvested in the current year, cleaning and airing to obtain wheat bran, and grinding the wheat bran to 80 meshes by using a grinding machine;
(2) extraction: performing ultrasonic extraction on the wheat bran by using ethyl acetate as an extraction solvent, wherein the extraction time is 30 min and the extraction power is 300W;
(3) centrifuging: centrifuging at 3500 r/min for 10min to obtain sample supernatant;
(4) concentration: collecting supernatant obtained by centrifugation, and concentrating by using a rotary evaporator at the temperature of 45 ℃ to obtain an alkyl resorcinol ethyl acetate extract concentrated solution;
(5) separation and purification: the first method adopts silica gel column chromatography, and comprises activating silica gel powder in a 120 deg.C oven at high temperature for 30 min, and cooling in a drier to room temperature; weighing the concentrated solution sample in the step (4) and silica gel powder in a mass ratio of 1:1, pouring the concentrated solution sample into an evaporation pan for sample mixing, then placing the evaporation pan in an oven for drying at 50-60 ℃, taking out the concentrated solution sample, cooling to room temperature, uniformly stirring the mixture for later use, carrying out dry-method sample loading on silica gel column chromatography, and eluting by using eluent to separate and purify; the second method is to adopt a solid phase extraction column, sample the concentrated solution obtained in the step (4) to the solid phase extraction column, and separate and purify the concentrated solution by washing the column with eluent;
(6) and (3) re-concentration: collecting the eluent obtained in the step (5), performing rotary evaporation and concentration, and absorbing the elution concentrated solution;
(7) high performance liquid chromatography analysis: redissolving with 1 mL methanol solution after nitrogen blowing, and detecting with high performance liquid chromatography after passing through an organic filter membrane of 0.22 mu m.
2. The extraction method according to claim 1, wherein the silica gel column used in the step (5) has a mass ratio of the sample mixing mass to the silica gel powder in the silica gel column chromatography of 1: 10.
3. The extraction method according to claim 1, wherein the eluent is petroleum ether-ethyl acetate, and v/v is 10: 1-1: 1.
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| CN1948248A (en) * | 2006-10-27 | 2007-04-18 | 南京农业大学 | Wheat bran total alkyl phenol extract and its preparation method and application |
| CN102686233A (en) * | 2009-12-30 | 2012-09-19 | 李海寿 | Composition for treating allergic diseases,using wheat bran extract or active ingredient isolated therefrom |
| CN103005282A (en) * | 2013-01-05 | 2013-04-03 | 江苏大学 | Wheat bran extract healthcare food with blood sugar reduction function and preparation method thereof |
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