CN111675684A - Method for extracting procyanidine from mulberry fruits - Google Patents
Method for extracting procyanidine from mulberry fruits Download PDFInfo
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- CN111675684A CN111675684A CN202010605855.2A CN202010605855A CN111675684A CN 111675684 A CN111675684 A CN 111675684A CN 202010605855 A CN202010605855 A CN 202010605855A CN 111675684 A CN111675684 A CN 111675684A
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- China
- Prior art keywords
- procyanidine
- procyanidin
- mulberry
- extracting
- crude
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- 235000008708 Morus alba Nutrition 0.000 title claims abstract description 63
- 240000000249 Morus alba Species 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 title claims abstract description 38
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- 239000011550 stock solution Substances 0.000 claims abstract description 22
- 241000218231 Moraceae Species 0.000 claims abstract description 12
- 239000000287 crude extract Substances 0.000 claims abstract description 12
- 238000000746 purification Methods 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- CWEZAWNPTYBADX-UHFFFAOYSA-N Procyanidin Natural products OC1C(OC2C(O)C(Oc3c2c(O)cc(O)c3C4C(O)C(Oc5cc(O)cc(O)c45)c6ccc(O)c(O)c6)c7ccc(O)c(O)c7)c8c(O)cc(O)cc8OC1c9ccc(O)c(O)c9 CWEZAWNPTYBADX-UHFFFAOYSA-N 0.000 claims description 46
- 229920002414 procyanidin Polymers 0.000 claims description 46
- XFZJEEAOWLFHDH-UHFFFAOYSA-N (2R,2'R,3R,3'R,4R)-3,3',4',5,7-Pentahydroxyflavan(48)-3,3',4',5,7-pentahydroxyflavan Natural products C=12OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C(O)C=C(O)C=1C(C1=C(O)C=C(O)C=C1O1)C(O)C1C1=CC=C(O)C(O)=C1 XFZJEEAOWLFHDH-UHFFFAOYSA-N 0.000 claims description 45
- MOJZMWJRUKIQGL-FWCKPOPSSA-N Procyanidin C2 Natural products O[C@@H]1[C@@H](c2cc(O)c(O)cc2)Oc2c([C@H]3[C@H](O)[C@@H](c4cc(O)c(O)cc4)Oc4c3c(O)cc(O)c4)c(O)cc(O)c2[C@@H]1c1c(O)cc(O)c2c1O[C@@H]([C@H](O)C2)c1cc(O)c(O)cc1 MOJZMWJRUKIQGL-FWCKPOPSSA-N 0.000 claims description 39
- HGVVOUNEGQIPMS-UHFFFAOYSA-N procyanidin Chemical compound O1C2=CC(O)=CC(O)=C2C(O)C(O)C1(C=1C=C(O)C(O)=CC=1)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C(O)=C1 HGVVOUNEGQIPMS-UHFFFAOYSA-N 0.000 claims description 39
- 239000000463 material Substances 0.000 claims description 22
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- 239000000243 solution Substances 0.000 claims description 18
- 239000012621 metal-organic framework Substances 0.000 claims description 17
- 239000002244 precipitate Substances 0.000 claims description 17
- 239000013179 MIL-101(Fe) Substances 0.000 claims description 16
- 238000003756 stirring Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
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- 238000011160 research Methods 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- 229920002350 Procyanidin B2 Polymers 0.000 description 6
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- 239000013177 MIL-101 Substances 0.000 description 5
- 235000013305 food Nutrition 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930003268 Vitamin C Natural products 0.000 description 3
- LMSNZLCSZWZZGU-UHFFFAOYSA-N butan-1-ol;hydrochloride Chemical compound Cl.CCCCO LMSNZLCSZWZZGU-UHFFFAOYSA-N 0.000 description 3
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- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 description 2
- 235000012734 epicatechin Nutrition 0.000 description 2
- 229940074391 gallic acid Drugs 0.000 description 2
- 235000004515 gallic acid Nutrition 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
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- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 1
- JPFCOVZKLAXXOE-XBNSMERZSA-N (3r)-2-(3,5-dihydroxy-4-methoxyphenyl)-8-[(2r,3r,4r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2h-chromen-4-yl]-3,4-dihydro-2h-chromene-3,5,7-triol Chemical compound C1=C(O)C(OC)=C(O)C=C1C1[C@H](O)CC(C(O)=CC(O)=C2[C@H]3C4=C(O)C=C(O)C=C4O[C@@H]([C@@H]3O)C=3C=CC(O)=CC=3)=C2O1 JPFCOVZKLAXXOE-XBNSMERZSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 241000218213 Morus <angiosperm> Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229920001991 Proanthocyanidin Polymers 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 240000008866 Ziziphus nummularia Species 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 235000010208 anthocyanin Nutrition 0.000 description 1
- 239000004410 anthocyanin Substances 0.000 description 1
- 229930002877 anthocyanin Natural products 0.000 description 1
- 150000004636 anthocyanins Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 229950001002 cianidanol Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 239000013110 organic ligand Substances 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
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Classifications
-
- 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
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0096—Purification; Precipitation; Filtration
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
-
- 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
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- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Botany (AREA)
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- Saccharide Compounds (AREA)
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Abstract
The invention provides a method for extracting procyanidine from mulberry fruits, which relates to the technical field of natural product extraction and comprises the following steps: (1) mulberry pretreatment, (2) procyanidine crude extract preparation, (3) sample stock solution preparation and (4) purification; the invention provides the method for extracting the procyanidine from the mulberries, the procyanidine is extracted through the steps of mulberry pretreatment, procyanidine crude extract preparation, sample stock solution preparation, purification and the like, the method has the advantages of simple process, easiness in operation, good extraction effect and the like, and the extracted procyanidine from the mulberries has various active effects of free radical removal, oxidation resistance and the like.
Description
[ technical field ] A method for producing a semiconductor device
The invention relates to the technical field of natural product extraction, and particularly relates to a method for extracting procyanidine from mulberry fruits.
[ background of the invention ]
Procyanidins (PCs), which are natural polyphenolic compounds, are also called condensed tannins, and are a mixture of oligomers and polymers formed by polymerization of monomers such as catechin (C), Epicatechin (EC), and Gallic Acid (GA). Researches show that the procyanidine has strong capacity of eliminating free radicals, is an internationally recognized natural antioxidant, and has potential market prospects due to the characteristics of strong antioxidant capacity, low toxicity, easy solubility in polar solvents and the like. However, the poor stability of procyanidins leads to low bioavailability, and therefore, the research of new technologies to improve the stability is an urgent problem to be solved.
Mulberry is fruit of Moraceae, Morus, perennial mulberry, also known as Mulberry and Mulberry jujube. According to literature reports, the mulberry not only has the physiological activity functions of resisting oxidation and cancer, preventing cardiovascular diseases and the like, but also has the effects of nourishing yin, improving eyesight, treating insomnia, preventing and treating constipation and the like, and is listed as a medicine-food homologous object in China. Researches show that the mulberry extract is purple black powder mainly prepared from mature mulberry fruits through extraction and purification by a proper organic solvent, and in recent years, researches on the mulberry fruit extract mainly comprise researches on the extraction purity and the oxidation resistance of anthocyanin. The extraction and purification of procyanidine from mulberry fruits and related researches are not reported.
[ summary of the invention ]
In view of the above, the present invention aims to provide a method for extracting a crude procyanidin extract from a mulberry fruit by using an ethanol aqueous solution, and a method for obtaining a high-purity procyanidin by sequentially concentrating the ethanol aqueous solution of the procyanidin, and then sequentially using distilled water to dissolve, and enriching, separating and purifying Metal-Organic Frameworks (MOFs) material MIL-101 (Fe).
In order to solve the technical problems, the invention adopts the following technical scheme:
a method for extracting procyanidine from mulberry fruits comprises the following steps:
(1) pretreatment of mulberries: collecting fresh mulberry fruits, cleaning, draining, mashing by a tissue mashing machine, and stirring uniformly to obtain mulberry raw pulp for later use;
(2) preparing a procyanidine crude extract: weighing 5.0g of mulberry raw pulp in a triangular flask according to a material-liquid ratio of 1 g: adding 20-24mL of ethanol solution, performing ultrasonic extraction at 45-55 deg.C for 25-35min, filtering, collecting filtrate, extracting the residue for 3 times, and mixing the filtrates to obtain procyanidin crude extract;
(3) preparing a sample stock solution: removing ethanol from the crude procyanidine extract obtained in the step (2) by rotary evaporation, transferring the crude procyanidine extract into a 100ml volumetric flask, fixing the volume to a scale by using distilled water, and shaking up to obtain a sample stock solution for later use;
(4) and (3) purification: a. weighing 20mg of MIL-101(Fe) material into a 25ml centrifuge tube, adding 20ml of sample stock solution, then carrying out ultrasonic treatment for 3-8min, sealing a centrifuge tube orifice, carrying out oscillation adsorption at room temperature until procyanidine is fully enriched on the surface of the MIL-101(Fe) material to form a PC-MOFs complex, and removing supernatant after centrifugal treatment to obtain procyanidine-enriched precipitate on the surface of the MIL-101(Fe) material; b. washing the precipitate with distilled water, drying the precipitate, adding 20ml ethanol solution, oscillating at room temperature for 10-14h to allow the PC-MOFs complex to resolve procyanidin, centrifuging, and collecting supernatant to obtain purified Mori fructus procyanidin.
In the invention, the mass concentration of the ethanol solution in the step (2) and the step (4) is 75-85%.
In the invention, further, the material-liquid ratio of the primary mulberry pulp to the ethanol solution in the step (2) is 1 g: 22 mL.
In the invention, further, the centrifugation treatment in the step (4) is centrifugation for 3-8min under the condition of rotating speed of 3800-.
In the invention, further, the drying of the precipitate in the step (4) is carried out for 5-8h in a vacuum drying oven with the temperature of 45-50 ℃.
In the invention, further, in the process of preparing the crude procyanidin extract in the step (2), the extraction condition is that ultrasonic extraction is carried out for 30min at the temperature of 50 ℃.
The procyanidine extracted from the mulberry is a polyphenol substance, not only is a natural antioxidant, but also can be used as a natural coloring agent, can be used as an auxiliary material added into food, can be added into food production, can enrich the food taste, and has nutritional value and functional effect.
The application also provides application of the mulberry procyanidin, which comprises the application of the mulberry procyanidin serving as an antioxidant added into edible oil.
The specific adding method comprises the following steps: a. mixing oleic acid polyglycerol monoester with ethanol in a ratio of 4: 1, stirring and mixing uniformly at the temperature of 20-40 ℃, dropwise adding the mulberry procyanidin according to the volume ratio of 1-5%, stirring and adding until a uniform and stable solution is formed, dispersing the obtained solution for 3-5 minutes at 20,000rpm, and standing for 1 hour to obtain an emulsion for later use; b. adjusting the temperature of the edible oil to 25-35 ℃, stirring for 25 minutes at 1,000rpm, slowly adding the emulsion into the edible oil according to the proportion that the mass fraction of the edible oil is 8%, and stirring while adding until the oil is clear and not turbid.
Metal-Organic Frameworks (MOFs) are a unique new class of Organic-inorganic hybrid porous materials. The MIL-101 series are compounds with three-dimensional pore channel structures, which are synthesized by taking trivalent transition metals and terephthalic acid as organic ligands through a hydrothermal method, and compared with common MOFs materials, the MIL-101 has larger specific surface area and larger pore capacity, and has better hydrothermal stability.
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
1. the invention provides a method for extracting procyanidine from mulberries, which comprises the steps of preprocessing mulberries, preparing a procyanidine crude extract, preparing a sample stock solution, purifying and the like, combines reasonable extraction conditions with a purification method, has the advantages of simple process, easiness in operation, high extraction purity and the like, has various active effects of removing free radicals, resisting oxidation and the like, and can improve technical support for application of procyanidine extracts in the fields of foods, medicines and the like. For example, the procyanidin obtained by the application is applied to edible oil, so that the natural plant antioxidant is used for replacing an oil-soluble chemical synthetic antioxidant in the processing of the edible oil, unsafe factors such as potential toxicity and carcinogenic effect of the synthetic antioxidant are overcome, and the application prospect in the market is wide.
2. The method is used for purifying the procyanidine which is extracted roughly, the characteristics of pi coordination and hydrogen bonding of an MIL-101 material are utilized, the MIL-101 material can play the pi coordination and hydrogen bonding of metal active sites of the MIL-101 material to improve the adsorption effect of an adsorbent on a target compound, and PC (procyanidine) is enriched in an MOFs material to form a PC-MOFs complex through a physical adsorption principle so as to achieve the purpose of enrichment and purification, a new research idea is provided for solving the stability problem of the procyanidine, and the procyanidine obtained by purification through the method is high in bioactive component enrichment rate and good in stability.
[ detailed description ] embodiments
The following examples may help one skilled in the art to more fully understand the present invention, but are not intended to limit the invention in any way.
Example 1
The embodiment provides a method for extracting procyanidine from mulberry, which specifically comprises the following steps:
a method for extracting procyanidine from mulberry fruits comprises the following steps:
(1) pretreatment of mulberries: collecting fresh mulberry fruits, cleaning, draining, mashing by a tissue mashing machine, and stirring uniformly to obtain mulberry raw pulp for later use;
(2) preparing a procyanidine crude extract: weighing 5.0g of mulberry raw pulp in a triangular flask according to a material-liquid ratio of 1 g: adding 20mL of ethanol solution with the mass concentration of 75%, performing ultrasonic extraction at 45 deg.C for 25min, filtering, collecting filtrate, extracting the residue for 3 times, and mixing the filtrates to obtain procyanidin crude extract;
(3) preparing a sample stock solution: removing ethanol from the crude procyanidine extract obtained in the step (2) by rotary evaporation, transferring the crude procyanidine extract into a 100ml volumetric flask, fixing the volume to a scale by using distilled water, and shaking up to obtain a sample stock solution for later use;
(4) and (3) purification: a. weighing 20mg of MIL-101(Fe) material into a 25ml centrifuge tube, adding 20ml of sample stock solution, then carrying out ultrasonic treatment for 3-8min, sealing a centrifuge tube orifice, carrying out oscillation adsorption at room temperature until procyanidine is fully enriched on the surface of the MIL-101(Fe) material to form a PC-MOFs complex, and removing supernatant after centrifugal treatment to obtain procyanidine-enriched precipitate on the surface of the MIL-101(Fe) material; b. washing the precipitate with distilled water, drying the precipitate in a vacuum drying oven at 45 deg.C for 5h, adding 20ml of 75% ethanol solution, oscillating at room temperature for 10h to allow the PC-MOFs complex to separate out procyanidin, centrifuging, and collecting supernatant to obtain purified procyanidin; the centrifugation treatment is carried out for 3min under the condition that the rotating speed is 3800 r/min. In the embodiment, the content of procyanidine in procyanidine is determined by adopting an n-butanol-hydrochloric acid color development method. Based on procyanidin B2 as control, procyanidin B2 equivalent accounts for 91.9%.
Example 2
The embodiment provides a method for extracting procyanidine from mulberry, which specifically comprises the following steps:
a method for extracting procyanidine from mulberry fruits comprises the following steps:
(1) pretreatment of mulberries: collecting fresh mulberry fruits, cleaning, draining, mashing by a tissue mashing machine, and stirring uniformly to obtain mulberry raw pulp for later use;
(2) preparing a procyanidine crude extract: weighing 5.0g of mulberry raw pulp in a triangular flask according to a material-liquid ratio of 1 g: adding an ethanol solution with the mass concentration of 80% into 22mL, performing ultrasonic extraction at 50 ℃ for 30min, filtering, collecting filtrate, repeatedly extracting the filter residue for 3 times according to the method, and combining the filtrates to obtain crude procyanidin extract for later use;
(3) preparing a sample stock solution: removing ethanol from the crude procyanidine extract obtained in the step (2) by rotary evaporation, transferring the crude procyanidine extract into a 100ml volumetric flask, fixing the volume to a scale by using distilled water, and shaking up to obtain a sample stock solution for later use;
(4) and (3) purification: a. weighing 20mg of MIL-101(Fe) material into a 25ml centrifuge tube, adding 20ml of sample stock solution, then carrying out ultrasonic treatment for 5min, sealing a centrifuge tube orifice, carrying out oscillation adsorption at room temperature until procyanidine is fully enriched on the surface of the MIL-101(Fe) material to form a PC-MOFs complex, and removing supernatant after centrifugal treatment to obtain procyanidine-enriched precipitate on the surface of the MIL-101(Fe) material; b. washing the precipitate with distilled water, drying the precipitate in a vacuum drying oven at 47 deg.C for 7h, adding 20ml of 80% ethanol solution, oscillating at room temperature for 12h to allow the PC-MOFs complex to separate out procyanidin, centrifuging, and collecting supernatant to obtain purified procyanidin; the centrifugation treatment is carried out for 6min under the condition that the rotating speed is 4000 r/min. In the embodiment, the content of procyanidine in procyanidine is determined by adopting an n-butanol-hydrochloric acid color development method. Based on procyanidin B2 as control, procyanidin B2 equivalent amount is 93.5%.
Example 3
The embodiment provides a method for extracting procyanidine from mulberry, which specifically comprises the following steps:
a method for extracting procyanidine from mulberry fruits comprises the following steps:
(1) pretreatment of mulberries: collecting fresh mulberry fruits, cleaning, draining, mashing by a tissue mashing machine, and stirring uniformly to obtain mulberry raw pulp for later use;
(2) preparing a procyanidine crude extract: weighing 5.0g of mulberry raw pulp in a triangular flask according to a material-liquid ratio of 1 g: adding ethanol solution with mass concentration of 85% into 24mL, performing ultrasonic extraction at 55 deg.C for 35min, filtering, collecting filtrate, extracting the residue for 3 times, and mixing the filtrates to obtain procyanidin crude extract;
(3) preparing a sample stock solution: removing ethanol from the crude procyanidine extract obtained in the step (2) by rotary evaporation, transferring the crude procyanidine extract into a 100ml volumetric flask, fixing the volume to a scale by using distilled water, and shaking up to obtain a sample stock solution for later use;
(4) and (3) purification: a. weighing 20mg of MIL-101(Fe) material into a 25ml centrifuge tube, adding 20ml of sample stock solution, then carrying out ultrasonic treatment for 8min, sealing a centrifuge tube orifice, carrying out oscillation adsorption at room temperature until procyanidine is fully enriched on the surface of the MIL-101(Fe) material to form a PC-MOFs complex, and removing supernatant after centrifugal treatment to obtain procyanidine-enriched precipitate on the surface of the MIL-101(Fe) material; b. washing the precipitate with distilled water, drying the precipitate in a vacuum drying oven at 50 deg.C for 8h, adding 20ml of 85% ethanol solution, oscillating at room temperature for 14h to allow PC-MOFs complex to separate procyanidin, centrifuging, and collecting supernatant to obtain purified procyanidin; the centrifugation treatment is carried out for 8min at the rotating speed of 4200 r/min. In the embodiment, the content of procyanidine in procyanidine is determined by adopting an n-butanol-hydrochloric acid color development method. Based on procyanidin B2 as control, procyanidin B2 equivalent accounts for 92.7%.
Comparative example 1
Unlike example 2, the method does not include step (4), the sample stock solution obtained in step (3) is the final product procyanidin, and the rest steps are the same. The content of procyanidin obtained was 54.7%.
Comparative example 2
Different from the embodiment 2, the step (4) is to purify the sample stock solution obtained in the step (3) by high-speed countercurrent chromatography, separate the sample stock solution by using a mixed solution of ethyl acetate, n-butanol, ethanol and water according to a volume ratio of 40:5:20:50 as a high-speed countercurrent separation system, collect effluent liquid, concentrate the effluent liquid, freeze-dry the effluent liquid until the water content is 15%, and obtain procyanidine, and the rest steps are the same. The obtained procyanidin content is 84.52%.
Comparative example 3
Different from the example 2, the step (4) is that the sample stock solution obtained in the step (3) is injected into a chromatographic column filled with the strong base anion exchange resin D201 at the flow rate of 1ml/min, then ethanol with the mass percent concentration of 50% is introduced for elution, effluent liquid is collected at the bottom of the column, and the rest steps are the same. The content of procyanidin obtained was 79.35%.
Comparative example 4
Unlike example 2, the extraction conditions in step (2) were: ultrasonic extracting at 35 deg.C for 45min, and filtering to obtain proanthocyanidin content of 86.98%.
Comparative example 5
Determination of the ability of procyanidins of Mulberry to scavenge free radicals
The 1, 1-diphenyl-2-trinitrophenylhydrazine method (DPPH method) is used. The radical scavenging ability of the procyanidin extracts obtained in examples 1-3 with vitamin C as a positive control is shown in table 1.
TABLE 1 evaluation table of radical scavenging ability of procyanidin extract
| Sample (I) | Example 1 | Example 2 | Example 3 | Vitamin C |
| Scavenging free radical IC50(μ g/mL) | 2.48 | 2.63 | 2.59 | 2.51 |
Therefore, the procyanidin obtained by the invention has the effect on scavenging free radicals equivalent to or better than that of vitamin C.
Comparative example 6
Determining antioxidant capacity of procyanidins from mulberries of the application
In order to illustrate the oxidation effect of the sunflower seed oil in edible oil, the applicant selects the sunflower seed oil and carries out comparison tests on the following groups:
a first group: an edible oil obtained by: a. mixing oleic acid polyglycerol monoester with ethanol in a ratio of 4: 1, stirring and mixing uniformly at the temperature of 30 ℃, dropwise adding the mulberry procyanidin according to the volume ratio of 3%, stirring and adding until a uniform and stable solution is formed, dispersing the obtained solution for 4 minutes at the speed of 20,000rpm, and standing for 1 hour to obtain an emulsion for later use; b. adjusting the temperature of the ChaiDou sunflower seed oil to 30 ℃, stirring for 25 minutes at 1,000rpm, slowly adding the emulsion into ChaiDou sunflower seed oil according to the proportion that the mass fraction of the edible oil is 8%, and stirring while adding until the oil is clear and not turbid;
second group: adding the emulsion into the sunflower seed oil according to the proportion that the edible oil accounts for 3 percent by mass, wherein the other modes are the same as the first group;
third group: adding the emulsion into the sunflower seed oil according to the proportion that the edible oil accounts for 12 percent by mass, wherein the other modes are the same as the first group;
and a fourth group: butylated Hydroxyanisole (BHA) is used as antioxidant and added into Dolichi seed oil.
Several groups of sunflower seed oil are placed in a water-proof constant temperature incubator at 60 ℃, the stirring is carried out once every day at regular time, the position of a sample in the constant temperature incubator is exchanged, and the sample is taken once to determine the peroxide value. The peroxide number was determined according to GB/T5009.37-2003.
The recorded data are shown in table 2:
TABLE 2 comparison of peroxide values for sunflower seed oil
As can be seen from table 3, when the procyanidin obtained by the present application is applied to edible oil, the natural plant antioxidant is used to replace the oil-soluble chemical synthetic antioxidant in the processing of edible oil, and the comparison experiment shows that the antioxidant effect of the first group and the third group is almost the same, but the dosage of the third group is more than that of the first group, and no better antioxidant performance is shown, so the cost is high, and the optimal addition amount of the procyanidin after being made into the emulsifier is 8%.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (7)
1. A method for extracting procyanidine from mulberry fruits is characterized by comprising the following steps:
(1) pretreatment of mulberries: collecting fresh mulberry fruits, cleaning, draining, mashing by a tissue mashing machine, and stirring uniformly to obtain mulberry raw pulp for later use;
(2) preparing a procyanidine crude extract: weighing 5.0g of mulberry raw pulp in a triangular flask according to a material-liquid ratio of 1 g: adding 20-24mL of ethanol solution, performing ultrasonic extraction at 45-55 deg.C for 25-35min, filtering, collecting filtrate, extracting the residue for 3 times, and mixing the filtrates to obtain procyanidin crude extract;
(3) preparing a sample stock solution: removing ethanol from the crude procyanidine extract obtained in the step (2) by rotary evaporation, transferring the crude procyanidine extract into a 100ml volumetric flask, fixing the volume to a scale by using distilled water, and shaking up to obtain a sample stock solution for later use;
(4) and (3) purification: a. weighing 20mg of MIL-101(Fe) material into a 25ml centrifuge tube, adding 20ml of sample stock solution, then carrying out ultrasonic treatment for 3-8min, sealing a centrifuge tube orifice, carrying out oscillation adsorption at room temperature until procyanidine is fully enriched on the surface of the MIL-101(Fe) material to form a PC-MOFs complex, and removing supernatant after centrifugal treatment to obtain procyanidine-enriched precipitate on the surface of the MIL-101(Fe) material; b. washing the precipitate with distilled water, drying the precipitate, adding 20ml ethanol solution, oscillating at room temperature for 10-14h to allow the PC-MOFs complex to resolve procyanidin, centrifuging, and collecting supernatant to obtain purified Mori fructus procyanidin.
2. The method for extracting procyanidin from mulberry fruit as claimed in claim 1, wherein the ethanol solution in the steps (2) and (4) has a mass concentration of 75-85%.
3. The method for extracting procyanidin from mulberry fruit as claimed in claim 1, wherein the ratio of raw juice of mulberry to ethanol solution in step (2) is 1 g: 22 mL.
4. The method for extracting procyanidin from mulberry fruit as claimed in claim 1, wherein the centrifugation treatment in the step (4) is centrifugation for 3-8min at 3800 and 4200 r/min.
5. The method for extracting procyanidin from mulberry fruit as claimed in claim 1, wherein the drying of the precipitate in the step (4) is performed for 5-8h in a vacuum drying oven at a temperature of 45-50 ℃.
6. The method for extracting procyanidin from mulberry fruit as claimed in claim 1, wherein the step (2) is carried out under the ultrasonic extraction condition at 50 ℃ for 30min in the process of preparing the crude procyanidin extract.
7. Procyanidins extracted by the method for extracting procyanidins from mulberries obtained in any one of claims 1 to 5.
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