CN107087792A - A kind of polymethoxyflavone and preparation method thereof - Google Patents
A kind of polymethoxyflavone and preparation method thereof Download PDFInfo
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- CN107087792A CN107087792A CN201710282818.0A CN201710282818A CN107087792A CN 107087792 A CN107087792 A CN 107087792A CN 201710282818 A CN201710282818 A CN 201710282818A CN 107087792 A CN107087792 A CN 107087792A
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- polymethoxyflavone
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- alkali
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- extract solution
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- 229930182496 polymethoxyflavone Natural products 0.000 title claims abstract description 141
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 58
- 239000003513 alkali Substances 0.000 claims abstract description 40
- 229930003944 flavone Natural products 0.000 claims abstract description 20
- 235000011949 flavones Nutrition 0.000 claims abstract description 20
- 239000000243 solution Substances 0.000 claims description 49
- 238000000605 extraction Methods 0.000 claims description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 30
- 239000002994 raw material Substances 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 21
- 238000002425 crystallisation Methods 0.000 claims description 17
- 230000008025 crystallization Effects 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 10
- 235000013399 edible fruits Nutrition 0.000 claims description 9
- 150000002213 flavones Chemical class 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000010410 layer Substances 0.000 claims description 4
- 241001093501 Rutaceae Species 0.000 claims description 3
- 230000009471 action Effects 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- ZAIANDVQAMEDFL-UHFFFAOYSA-N 3-methoxy-2-phenylchromen-4-one Chemical compound O1C2=CC=CC=C2C(=O)C(OC)=C1C1=CC=CC=C1 ZAIANDVQAMEDFL-UHFFFAOYSA-N 0.000 claims 2
- YEHDMSUNJUONMW-UHFFFAOYSA-N methoxyflavone Natural products COC1=CC=CC=C1C1=CC(=O)C2=CC=CC=C2O1 YEHDMSUNJUONMW-UHFFFAOYSA-N 0.000 claims 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 235000013305 food Nutrition 0.000 abstract description 11
- 230000036541 health Effects 0.000 abstract description 11
- 239000012535 impurity Substances 0.000 abstract description 11
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract description 9
- 238000011084 recovery Methods 0.000 abstract description 9
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract description 9
- 150000002212 flavone derivatives Chemical class 0.000 abstract description 8
- 238000007670 refining Methods 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 45
- 235000012054 meals Nutrition 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 11
- 201000011510 cancer Diseases 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- -1 chromocor compound Chemical class 0.000 description 5
- 235000020971 citrus fruits Nutrition 0.000 description 5
- 241000207199 Citrus Species 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000033228 biological regulation Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000004064 recycling Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- OBIOZWXPDBWYHB-UHFFFAOYSA-N Nobiletin Natural products C1=CC(OC)=CC=C1C1=C(OC)C(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 OBIOZWXPDBWYHB-UHFFFAOYSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- MRIAQLRQZPPODS-UHFFFAOYSA-N nobiletin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 MRIAQLRQZPPODS-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LKMNXYDUQXAUCZ-UHFFFAOYSA-N sinensetin Chemical compound C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C=C2O1 LKMNXYDUQXAUCZ-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- ULSUXBXHSYSGDT-UHFFFAOYSA-N tangeretin Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 ULSUXBXHSYSGDT-UHFFFAOYSA-N 0.000 description 2
- QEWSAPKRFOFQIU-UHFFFAOYSA-N 5-Hydroxy-6,7,3',4'-tetramethoxyflavone Natural products C1=C(OC)C(OC)=CC=C1C1=CC(=O)C2=C(O)C(OC)=C(OC)C=C2O1 QEWSAPKRFOFQIU-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 235000005976 Citrus sinensis Nutrition 0.000 description 1
- 240000002319 Citrus sinensis Species 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 241000711904 Pneumoviridae Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- IECRXMSGDFIOEY-UHFFFAOYSA-N Tangeretin Natural products COC=1C(OC)=C(OC)C(OC)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C=C1 IECRXMSGDFIOEY-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002790 anti-mutagenic effect Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000000601 blood cell Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 206010020718 hyperplasia Diseases 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 230000000527 lymphocytic effect Effects 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
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
- 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Mycology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
The invention provides a kind of polymethoxyflavone and preparation method thereof, the preparation method of polymethoxyflavone of the present invention, the polymethoxyflavone in polymethoxyflavone extract solution is dissolved using solvent, pass through alkali abstraction impurity removal, it is refining to obtain polymethoxyflavone, with low cost, technique is simple, the cycle is short, recovery rate is high, product purity is high, yield is high, can meet the requirement of food, health products etc., again can high-volume, realize industrialization on a large scale.The content of general flavone is high in polymethoxyflavone product of the present invention, disclosure satisfy that the requirement of food, health products etc..
Description
Technical field
The present invention relates to polymethoxyflavone extraction purification technical field, in particular to a kind of polymethoxyflavone
And preparation method thereof.
Background technology
Polymethoxyflavone is the chromocor compound that a class is existed only in citrus fruit, so far, from citrus
It is middle to separate and identify more than 20 kinds of polymethoxyflavone, mainly including Nobiletin (nobiletin), orange peel element
(Tangeretin), sweet orange flavones (sinensetin) etc., this kind of material contains multiple methoxyl groups, in planar structure, and polarity is small,
Therefore with the bioactivity more stronger than general flavones and pharmacological action, while having advantages below：
1. antimutagenic effect：
This flavonoids protects DNA (DNA) from the damage of ultraviolet by absorbing ultraviolet, and can be clear
Except the free radical around DNA molecular mutagenesis is oxidized to weaken DNA molecular.
2. suppress tumour, cancer cell hyperplasia：
Anti-tumour cell proliferative, such as cancer cell of bone marrow, lymphocytic cancer cell, ovarian cancer cell, prostate gland cancer cell and flat
Cancer cell plays the role of Inhibit proliferaton, when dosage is that 8 μm of ol/L can just kill flat cancer cell.This flavonoids is by changing cancer
The cell membrane and enzyme and signal transduction mechanism of cell disturb its DNA replication dna, and protein is synthesized and worked.
3. suppress the mobility of cancer cell：
The general method with chemotherapy and radiation suppresses growth and the propagation of tumour cell, but to preventing diffusion very little,
And Citrus polymethoxyflavone can suppress cancer cell diffusion, mainly suppress the mobility of cancer cell.
4. antivirus action：
The significant suppression bone marrow poliomyelitis virus of polymethoxyflavone energy, herpes simplex virus bears influenza virus and born of the same parents
The infection and duplication of precursor virus, suppress the propagation of Pneumovirinae.
5. antioxidation：
Citrus polymethoxyflavone can remove free radical in human body, and per-compound suppresses ester matter peroxidating.May be used also
For preventing angiocardiopathy, coronary heart disease is prevented, suppresses platelet aggregation, the permeability and fragility of capillary is reduced.
Clinically there is following purposes：
1. polymethoxyflavone can as Citrus Taxonomy marker；
2. the personation in lemon juice, inferior product can be checked by the composition for analyzing polymethoxyflavone in fruit juice；
3. with the effect for reducing erythrocyte aggregation and reduction blood cell settling rate in human body；
4. it can induce the growth that leucocyte suppresses HL60 leukaemia；
5. the property with dissolved cancer cell, and the blood circulation of patients with coronary artery disease is worked.
In industrialized production, the isolating and purifying of the polymethoxyflavone for being about 50% for product content all need by
Extract, realize the step of resin or column chromatography for separation, ethanol are re-refined, it is complicated that these methods have a separation circuit, step
It is cumbersome, the shortcoming that time-consuming, product content is low, yield is low, it is difficult to realize industrialization.
In view of this, it is special to propose the present invention.
The content of the invention
The first object of the present invention is to provide a kind of preparation method of polymethoxyflavone, and this method is with low cost, work
Skill is simple, the cycle is short, recovery rate is high, product purity is high, yield is high, can meet the requirement of food, health products etc., again can be big
In batches, industrialization is realized on a large scale.
The second object of the present invention is that providing a kind of preparation method for using described polymethoxyflavone prepares
Polymethoxyflavone product, the content of general flavone is high in described polymethoxyflavone product, disclosure satisfy that food, health products
Deng requirement.
In order to realize the above-mentioned purpose of the present invention, spy uses following technical scheme：
A kind of preparation method of polymethoxyflavone, polymethoxyflavone is prepared using the raw material containing polymethoxyflavone
Extract solution, dissolves the polymethoxyflavone in polymethoxyflavone extract solution using stirring solvent, extraction is stirred using alkali,
By the concentration of gained organic layer, refine, obtain polymethoxyflavone.
The preparation method of polymethoxyflavone of the present invention, many methoxies in polymethoxyflavone extract solution are dissolved using solvent
Base flavones, by alkali abstraction impurity removal, is refining to obtain polymethoxyflavone, with low cost, technique is simple, the cycle is short, recovery rate is high,
Product purity is high, yield is high, can meet the requirement of food, health products etc., again can high-volume, realize industry on a large scale
Change.
Alternatively, the solvent includes the one or more in organic solvent, preferably includes in fat-soluble organic solvent
One or more, further preferably including the one or more in petroleum ether, hexamethylene, toluene and ethyl acetate.
Preferably, the boiling range of the petroleum ether is 90-120 DEG C.
Alternatively, it is described use stirring solvent dissolve polymethoxyflavone extract solution in polymethoxyflavone temperature for
More than 0 DEG C, more preferably preferably 0-40 DEG C, normal temperature condition.
Alternatively, during the stirring of the polymethoxyflavone in the use stirring solvent dissolving polymethoxyflavone extract solution
Between be more than 30min, more preferably preferably 30-60min, 45min.
Alternatively, the consumption of the solvent is 0.1-0.4 times of material quality, preferably 0.2-0.4 times of material quality,
More preferably 0.2 times of material quality.
Alternatively, the alkali includes the one or more in alkali metal hydroxide, preferably includes sodium hydroxide, hydroxide
One or both of potassium, further preferably including sodium hydroxide.
Preferably, the alkali includes aqueous slkali.
It is further preferred that the aqueous slkali includes the aqueous solution of alkali.
It is further preferred that in the aqueous slkali alkali mass fraction be 0.5%-3%, preferably 2%-3%, further
Preferably 2%.
It is further preferred that the consumption of the alkali lye is 0.1-0.4 times of material quality, the preferably 0.2- of material quality
0.4 times, more preferably the 0.2 of material quality times.
Alternatively, described to use the mixing time that alkali is stirred extraction for more than 30min, preferably 30-60min enters
One step is preferably 45min.
Alternatively, the extraction time of repose for using alkali to be stirred extraction is more than 30min, preferably 30-
60min, more preferably 45min.
Alternatively, it is described to use alkali to be stirred the temperature of extraction for more than 0 DEG C, preferably 0-40 DEG C, further preferably
For normal temperature condition.
Alternatively, the temperature that gained organic layer is concentrated is 75-85 DEG C, preferably 80-85 DEG C, is more preferably
80℃。
Alternatively, the refined medicinal extract for including gained organic layer being concentrated to give, is dissolved using solvent, stands crystallization.
Preferably, the solvent includes alcoholic solution, preferably includes ethanol solution, is further preferably including volume fraction
More than 95% food-grade ethanol solution.
Preferably, the consumption of the solvent is 0.5-1 times of medicinal extract quality, preferably 0.5-0.8 times, is more preferably
0.5 times.
Preferably, the dissolving includes backflow dissolving, carries out standing crystallization after cooling again.
It is further preferred that the cooling includes natural cooling.
Preferably, the time for standing crystallization is 2-4h, more preferably preferably 3-4h, 3h.
Alternatively, the raw material of the use containing polymethoxyflavone, which prepares polymethoxyflavone extract solution, includes：
Raw material containing polymethoxyflavone is extracted with solvent refluxing, polymethoxyflavone extract solution is obtained.
Preferably, gained polymethoxyflavone extract solution is concentrated.
It is further preferred that the concentration includes being concentrated into gained polymethoxyflavone extract solution into the 1/10- of original volume
1/20, the 1/10-1/15 of original volume is preferably concentrated into, the 1/10 of original volume is further preferably concentrated into.
Preferably, the solvent includes the one or more in alcoholic solvent, preferably includes alcohol solvent.
It is further preferred that the volume fraction of the solvent is 40%-80%, preferably 60%-80%, further preferably
For 60%.
Preferably, the consumption of the solvent is 2-5 times of material quality, more preferably preferably 4-5 times, 5 times.
Preferably, the time that the raw material containing polymethoxyflavone is extracted with solvent refluxing is 1-2h, is preferably
1-1.5h, more preferably 1.5h.
Preferably, it is described that the raw material containing polymethoxyflavone is repeated into refluxing extraction 2-5 times with solvent, preferably extract 3-
5 times, further preferably extract 3 times, merge gained extract solution, obtain polymethoxyflavone extract solution.
Alternatively, stirring extraction gained organic layer be washed to pH for 7-7.5.
Preferably, the washing water consumption is 0.1-0.4 times of material quality, preferably 0.1-0.2 times of material quality,
More preferably 0.1 times.
Preferably, the number of times of the washing is 2-5 times, more preferably preferably 2-3 times, 2 times.
Alternatively, the raw material containing polymethoxyflavone includes rutaceae fruit, preferably includes Ponkan, enters one
Step preferably includes Ponkan young fruit.
Alternatively, polymethoxyflavone is filtered, dried, obtain polymethoxyflavone product.
Preferably, the temperature of the drying is 40-80 DEG C, more preferably preferably 40-60 DEG C, 60 DEG C.
The polymethoxyflavone product prepared using a kind of preparation method of above-mentioned polymethoxyflavone.
The content of general flavone is high in polymethoxyflavone product of the present invention, disclosure satisfy that the requirement of food, health products etc..
Compared with prior art, beneficial effects of the present invention are：
The preparation method of polymethoxyflavone of the present invention, many methoxies in polymethoxyflavone extract solution are dissolved using solvent
Base flavones, by alkali abstraction impurity removal, is refining to obtain polymethoxyflavone, with low cost, technique is simple, the cycle is short, recovery rate is high,
Product purity is high, yield is high, can meet the requirement of food, health products etc., again can high-volume, realize industry on a large scale
Change.The content of general flavone is high in polymethoxyflavone product of the present invention, disclosure satisfy that the requirement of food, health products etc..
Embodiment
Technical scheme is clearly and completely described below in conjunction with embodiment, but ability
Field technique personnel will be understood that following described embodiment is a part of embodiment of the invention, rather than whole embodiments,
The present invention is merely to illustrate, and is not construed as limiting the scope of the present invention.Based on the embodiment in the present invention, the common skill in this area
The every other embodiment that art personnel are obtained under the premise of creative work is not made, belongs to the model that the present invention is protected
Enclose.Unreceipted actual conditions person in embodiment, the condition advised according to normal condition or manufacturer is carried out.Agents useful for same or instrument
Unreceipted production firm person, is the conventional products that can be obtained by commercially available purchase.
The invention provides a kind of preparation method of polymethoxyflavone, prepared using the raw material containing polymethoxyflavone
Polymethoxyflavone extract solution, dissolves the polymethoxyflavone in polymethoxyflavone extract solution, using alkali using stirring solvent
Extraction is stirred, by the concentration of gained organic layer, refines, obtains polymethoxyflavone.
The preparation method of polymethoxyflavone of the present invention, many methoxies in polymethoxyflavone extract solution are dissolved using solvent
Base flavones, by alkali abstraction impurity removal, is refining to obtain polymethoxyflavone, with low cost, technique is simple, the cycle is short, recovery rate is high,
Product purity is high, yield is high, can meet the requirement of food, health products etc., again can high-volume, realize industry on a large scale
Change.
In a kind of preferred embodiment of the present invention, the solvent includes the one or more in organic solvent, excellent
Choosing includes the one or more in fat-soluble organic solvent, further preferably including petroleum ether, hexamethylene, toluene and ethyl acetate
In one or more.
Preferably, the boiling range of the petroleum ether is 90-120 DEG C.
Using specific solvent, the solubility of polymethoxyflavone is favorably improved, extraction efficiency and yield is improved.
In a kind of preferred embodiment of the present invention, the use stirring solvent dissolves polymethoxyflavone extract solution
In polymethoxyflavone temperature be more than 0 DEG C, preferably 0-40 DEG C, more preferably normal temperature condition.
In a kind of preferred embodiment of the present invention, the use stirring solvent dissolves polymethoxyflavone extract solution
In polymethoxyflavone mixing time be more than 30min, more preferably preferably 30-60min, 45min.
Using specified temp and time, the extraction efficiency and yield of polymethoxyflavone are favorably improved.
In a kind of preferred embodiment of the present invention, the consumption of the solvent is 0.1-0.4 times of material quality, excellent
0.2 times of elect material quality as 0.2-0.4 times, more preferably material quality.
Using specific solvent consumption, the extraction efficiency and yield of polymethoxyflavone are favorably improved.
Alkali is that a class has very corrosive alkaline chemical, it means that it can the stickum such as dissolved fat, it is right
There is very high solvability in other materials.Polymethoxyflavone does not dissolve in alkali, and alkali has very strong to the impurity among solution
Removal is acted on, and can be used to purify polymethoxyflavone.
In a kind of preferred embodiment of the present invention, the alkali includes one kind or many in alkali metal hydroxide
Kind, one or both of sodium hydroxide, potassium hydroxide are preferably included, further preferably including sodium hydroxide.
Preferably, the alkali includes aqueous slkali.
It is further preferred that the aqueous slkali includes the aqueous solution of alkali.
It is further preferred that in the aqueous slkali alkali mass fraction be 0.5%-3%, preferably 2%-3%, further
Preferably 2%.
It is further preferred that the consumption of the alkali lye is 0.1-0.4 times of material quality, the preferably 0.2- of material quality
0.4 times, more preferably the 0.2 of material quality times.
Using special component and the alkali of consumption, the clearance of impurity is favorably improved, gained is further improved Polymethoxylated
The purity of flavones.
In a kind of preferred embodiment of the present invention, it is described use alkali be stirred the mixing time of extraction for
More than 30min, preferably 30-60min, more preferably 45min.
In a kind of preferred embodiment of the present invention, the extraction time of repose for using alkali to be stirred extraction for
More than 30min, preferably 30-60min, more preferably 45min.
Using specific mixing time and time of repose, contribute to the abundant progress of extraction process, improve the clearance of impurity,
Further improve the purity of gained polymethoxyflavone product.
It is described to use alkali to be stirred the temperature of extraction for more than 0 DEG C in a kind of preferred embodiment of the present invention,
Preferably 0-40 DEG C, more preferably normal temperature condition.
The process that the use alkali of the present invention is stirred extraction can be carried out in certain temperature range, also can be in normal temperature condition
Lower to carry out, cost is low, is easy to operation.
Preferably, using alkali be stirred extraction when alkali should be added in solution to be extracted, it is to avoid charging sequence is wrong
Extraction efficiency is influenceed by mistake, further influence polymethoxyflavone product yield.
In a kind of preferred embodiment of the present invention, the temperature that gained organic layer is concentrated is 75-85 DEG C, excellent
Elect 80-85 DEG C, more preferably 80 DEG C as.
Using specified temp, thickening efficiency is favorably improved.
In a kind of preferred embodiment of the present invention, the refined leaching for including gained organic layer being concentrated to give
Cream, is dissolved using solvent, stands crystallization.
Using the method for dissolving crystallization, the purity of gained polymethoxyflavone product can be effectively improved, while reducing production
Product lose.
Preferably, the solvent includes alcoholic solution, preferably includes ethanol solution, is further preferably including volume fraction
More than 95% food-grade ethanol solution.
Use volume fraction for more than 95% food-grade ethanol solution, can meet gained polymethoxyflavone product
The requirement of food, health products quality.
Preferably, the consumption of the solvent is 0.5-1 times of medicinal extract quality, preferably 0.5-0.8 times, is more preferably
0.5 times.
Using special component and the solvent of consumption, the solvent of polymethoxyflavone is helped lend some impetus to, is easy to stand crystallization behaviour
Make, while reducing the loss of product.
Preferably, the dissolving includes backflow dissolving, carries out standing crystallization after cooling again, contributes to polymethoxyflavone
Quick dissolving, and reduce product loss.
It is further preferred that the cooling includes natural cooling.
By the way of natural cooling, help to stand the abundant progress of crystallization, while avoiding fast cooling from causing impurity
Together separate out, improve the purity of gained polymethoxyflavone product.
Preferably, the time for standing crystallization is 2-4h, more preferably preferably 3-4h, 3h.
Using the specific standing crystallization time, help to stand the abundant progress of crystallization, while it is miscellaneous to avoid fast cooling from causing
Matter is together separated out, and improves the purity of gained polymethoxyflavone product.
It is described that many first are prepared using the raw material containing polymethoxyflavone in a kind of preferred embodiment of the present invention
Epoxide flavone extractive includes：
Raw material containing polymethoxyflavone is extracted with solvent refluxing, polymethoxyflavone extract solution is obtained.
By the way of solvent refluxing is extracted, the high efficiency extraction from raw material is contributed to go out polymethoxyflavone.
Preferably, gained polymethoxyflavone extract solution is concentrated, to reduce polymethoxyflavone in subsequent technique
Loss.
It is further preferred that the concentration includes being concentrated into gained polymethoxyflavone extract solution into the 1/10- of original volume
1/20, the 1/10-1/15 of original volume is preferably concentrated into, the 1/10 of original volume is further preferably concentrated into.
Polymethoxyflavone extract solution is concentrated into designated volume, is easy to the progress of subsequent technique, reduces cost, subtract simultaneously
The loss of few polymethoxyflavone.
Preferably, the solvent includes the one or more in alcoholic solvent, preferably includes alcohol solvent.
It is further preferred that the volume fraction of the solvent is 40%-80%, preferably 60%-80%, further preferably
For 60%.
Preferably, the consumption of the solvent is 2-5 times of material quality, more preferably preferably 4-5 times, 5 times.
Using special component and the solvent of consumption, the extraction efficiency to polymethoxyflavone is favorably improved, many first are improved
The yield of epoxide flavones.
Preferably, the time that the raw material containing polymethoxyflavone is extracted with solvent refluxing is 1-2h, is preferably
1-1.5h, more preferably 1.5h.
Using specific reflux extracting time, the extraction efficiency to polymethoxyflavone is favorably improved, is improved Polymethoxylated
The yield of flavones.
Preferably, it is described that the raw material containing polymethoxyflavone is repeated into refluxing extraction 2-5 times with solvent, preferably extract 3-
5 times, further preferably extract 3 times, merge gained extract solution, obtain polymethoxyflavone extract solution.
By the way of refluxing extraction is repeated, the extraction efficiency to polymethoxyflavone is favorably improved, many methoxies are improved
The yield of base flavones.
In a kind of preferred embodiment of the present invention, stirring extraction gained organic layer be washed to pH for 7-
7.5, it is to avoid influence is produced on subsequent technique, reduce impurity.
Preferably, the washing water consumption is 0.1-0.4 times of material quality, preferably 0.1-0.2 times of material quality,
More preferably 0.1 times.
Preferably, the number of times of the washing is 2-5 times, more preferably preferably 2-3 times, 2 times.
Specific times are washed using the water of specific consumption, water washing effect is favorably improved, it is to avoid to being introduced in subsequent technique
Impurity.
In a kind of preferred embodiment of the present invention, the raw material containing polymethoxyflavone is planted including Rutaceae
Thing fruit, preferably includes Ponkan, further preferably includes Ponkan young fruit.
Preferably, the raw material should again be used after drying and crushing.
Preferably, material quality of the present invention refers both to the quality after raw material drying is crushed.
In a kind of preferred embodiment of the present invention, polymethoxyflavone is filtered, dried, Polymethoxylated Huang is obtained
Ketone product.
Preferably, the temperature of the drying is 40-80 DEG C, more preferably preferably 40-60 DEG C, 60 DEG C.
Using specific drying temperature, drying efficiency is favorably improved, while ensureing the product of gained polymethoxyflavone product
Matter.
The polymethoxyflavone product prepared using a kind of preparation method of above-mentioned polymethoxyflavone.
The content of general flavone is high in polymethoxyflavone product of the present invention, disclosure satisfy that the requirement of food, health products etc..
Embodiment 1
A kind of preparation method of polymethoxyflavone, including：
Ponkan young fruit drying to moisture is met to the raw material meal that 2-3mm is ground into after regulation, 1kg coarse powder is weighed in extraction
In tank, the volume fraction for adding 2 times of inventorys of meal quality is 40% ethanol, and return stirring is extracted 2 times, each extraction time
For 1-h, extract solution is merged into recycling design, normal pressure is concentrated into the 1/10 of original volume, obtains concentrate；
The petroleum ether of 0.1 times of meal quality is added into gained concentrate, 30min is stirred at room temperature；
Backward tank in add 0.1 times of meal quality, mass fraction be 0.5% sodium hydrate aqueous solution, stirred at 0 DEG C
Extraction 30min is mixed, 30min layerings are stood, buck layer can be discharged when liquid has obvious layering, add meal quality 0.1
Times aqueous washing tank in liquid make for 2 times its pH value be 7.0-7.5；
Concentration and recovery petroleum ether, obtains medicinal extract at 75 DEG C；
The volume fraction of 0.5 times of medicinal extract quality is added into gained medicinal extract bright to having for 95% food-grade ethanol return stirring
During aobvious particle Precipitation, temperature in tank is naturally cooled to 25-30 DEG C, crystallization 2h is stood, filtering is dried at 40 DEG C,
Crushing obtains polymethoxyflavone product.
Embodiment 2
A kind of preparation method of polymethoxyflavone, including：
Ponkan young fruit drying to moisture is met and is ground into 2-3mm raw material meal after regulation, 10kg coarse powder is weighed in carrying
Take in tank, the volume fraction for adding the inventory of meal quality 4 is 80% ethanol, and return stirring is extracted 5 times, each extraction time
For 2h, extract solution is merged into recycling design, normal pressure is concentrated into the 1/20 of original volume, obtains concentrate；
The toluene of 0.4 times of meal quality is added into gained concentrate, 60min is stirred at room temperature；
Backward tank in add 0.4 times of meal quality, mass fraction be 3% sodium hydrate aqueous solution, stirred at 40 DEG C
Extraction 60min is mixed, 60min layerings are stood, buck layer can be discharged when liquid has obvious layering, add meal quality 0.4
Liquid makes its pH value be 7.0-7.5 5 times in times aqueous washing tank；
Concentration and recovery toluene, obtains medicinal extract at 85 DEG C；
The volume fraction of 1 times of medicinal extract quality is added into gained medicinal extract obvious to having for 95% food-grade ethanol return stirring
Particle Precipitation when, temperature in tank is naturally cooled to 25-30 DEG C, crystallization 4h is stood, filtering is dried, powder at 80 DEG C
It is broken to obtain polymethoxyflavone product.
Embodiment 3
A kind of preparation method of polymethoxyflavone, including：
Ponkan young fruit drying to moisture is met and is ground into 2-3mm raw material meal after regulation, 50kg coarse powder is weighed in carrying
Take in tank, the volume fraction for adding 5 times of inventorys of meal quality is 60% ethanol, and return stirring is extracted 3 times, when extracting every time
Between be 1.5h, extract solution is merged into recycling design, normal pressure is concentrated into the 1/10 of original volume, obtains concentrate；
The ethyl acetate of 0.2 times of meal quality is added into gained concentrate, 45min is stirred at room temperature；
Backward tank in add 0.2 times of meal quality, mass fraction be 2% sodium hydrate aqueous solution, stir at normal temperatures
Extraction 45min is mixed, 45min layerings are stood, buck layer can be discharged when liquid has obvious layering, add meal quality 0.1
Liquid 3 times in aqueous washing tank again, it is 7.0-7.5 to make its pH value；
Concentration and recovery petroleum ether, obtains medicinal extract at 80 DEG C；
The volume fraction of 0.8 times of medicinal extract quality is added into medicinal extract obvious to having for 95% food-grade ethanol return stirring
During particle Precipitation, temperature in tank is naturally cooled to 25-30 DEG C, crystallization 3h is stood, filtering dry, pulverize at 60 DEG C
Obtain polymethoxyflavone product.
Detection calculating (HPLC), acquired results such as table 1 are carried out to polymethoxyflavone product obtained by 1-3 of the embodiment of the present invention
It is shown：
The polymethoxyflavone Product checking data of the present invention of table 1
| Embodiment | General flavone/g | General flavone content | Yield |
| Embodiment 1 | 11.24 | 92.5% | 91.2% |
| Embodiment 2 | 114.86 | 93.2% | 93.1% |
| Embodiment 3 | 571.18 | 93.5% | 93.8% |
It can be seen from Table 1 that, the preparation method of polymethoxyflavone of the present invention is high to the recovery rate of polymethoxyflavone,
Up to more than 90%, the content of general flavone is high in gained polymethoxyflavone product, up to more than 92%, present invention institute much first
Epoxide flavones product is brilliant white or light yellow solid product, and Process planning flow of the invention is simple and easy to apply, without large-scale, expensive
The equipment of weight, it is time-consuming it is short, without by resin and column chromatography complex separations, but utilize product and impurity solubility in alkali lye
Difference separated, be especially suitable for mass producing, be easily achieved industrialization.
Although illustrate and describing the present invention with specific embodiment, but it will be appreciated that various embodiments above is only used
To illustrate technical scheme, rather than its limitations；It will be understood by those within the art that：Without departing substantially from this hair
In the case of bright spirit and scope, the technical scheme described in foregoing embodiments can be modified, or to wherein
Some or all of technical characteristic carries out equivalent substitution；And these modifications or replacement, do not make the essence of appropriate technical solution
Depart from the scope of various embodiments of the present invention technical scheme；It is, therefore, intended that including belonging to the present invention in the following claims
In the range of all these substitutions and modifications.
Claims (10)
1. a kind of preparation method of polymethoxyflavone, it is characterised in that prepared using the raw material containing polymethoxyflavone many
Methoxy flavone extract solution, is dissolved the polymethoxyflavone in polymethoxyflavone extract solution using stirring solvent, is entered using alkali
Row stirring extraction, by the concentration of gained organic layer, refines, obtains polymethoxyflavone.
2. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that the solvent includes
One or more in machine solvent, preferably include the one or more in fat-soluble organic solvent, further preferably including oil
One or more in ether, hexamethylene, toluene and ethyl acetate；
Preferably, the boiling range of the petroleum ether is 90-120 DEG C；
Preferably, the temperature for using the polymethoxyflavone in stirring solvent dissolving polymethoxyflavone extract solution is 0 DEG C
More than, preferably 0-40 DEG C, more preferably normal temperature condition；
Preferably, it is described use stirring solvent dissolve polymethoxyflavone extract solution in polymethoxyflavone mixing time for
More than 30min, preferably 30-60min, more preferably 45min；
Preferably, the consumption of the solvent is 0.1-0.4 times of material quality, preferably 0.2-0.4 times of material quality, enters one
Step is preferably 0.2 times of material quality.
3. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that the alkali includes alkali gold
Belong to the one or more in hydroxide, preferably include one or both of sodium hydroxide, potassium hydroxide, further preferably bag
Include sodium hydroxide；
Preferably, the alkali includes aqueous slkali；
It is further preferred that the aqueous slkali includes the aqueous solution of alkali；
It is further preferred that in the aqueous slkali alkali mass fraction be 0.5%-3%, preferably 2%-3%, further preferably
For 2%；
It is further preferred that the consumption of the alkali lye is 0.1-0.4 times of material quality, the preferably 0.2-0.4 of material quality
Times, more preferably the 0.2 of material quality times；
Preferably, it is described to use the mixing time that alkali is stirred extraction for more than 30min, preferably 30-60min, further
Preferably 45min；
Preferably, the extraction time of repose for using alkali to be stirred extraction is more than 30min, and preferably 30-60min enters
One step is preferably 45min；
Preferably, it is described to use alkali to be stirred the temperature of extraction for more than 0 DEG C, it is preferably 0-40 DEG C, more preferably normal
Warm condition.
4. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that described that gained is organic
The temperature of layer concentration is 75-85 DEG C, more preferably preferably 80-85 DEG C, 80 DEG C.
5. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that described refine includes inciting somebody to action
The medicinal extract that gained organic layer is concentrated to give, is dissolved using solvent, stands crystallization；
Preferably, the solvent include alcoholic solution, preferably include ethanol solution, further preferably include volume fraction be 95% with
On food-grade ethanol solution；
Preferably, the consumption of the solvent is 0.5-1 times of medicinal extract quality, preferably 0.5-0.8 times, more preferably 0.5
Times；
Preferably, the dissolving includes backflow dissolving, carries out standing crystallization after cooling again；
It is further preferred that the cooling includes natural cooling；
Preferably, the time for standing crystallization is 2-4h, more preferably preferably 3-4h, 3h.
6. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that described using containing many
The raw material of methoxy flavone, which prepares polymethoxyflavone extract solution, to be included：
Raw material containing polymethoxyflavone is extracted with solvent refluxing, polymethoxyflavone extract solution is obtained；
Preferably, gained polymethoxyflavone extract solution is concentrated；
It is further preferred that the concentration includes being concentrated into gained polymethoxyflavone extract solution into the 1/10-1/20 of original volume,
It is preferred that being concentrated into the 1/10-1/15 of original volume, the 1/10 of original volume is further preferably concentrated into；
Preferably, the solvent includes the one or more in alcoholic solvent, preferably includes alcohol solvent；
It is further preferred that the volume fraction of the solvent is 40%-80%, preferably 60%-80%, more preferably
60%；
Preferably, the consumption of the solvent is 2-5 times of material quality, more preferably preferably 4-5 times, 5 times；
Preferably, the time that the raw material containing polymethoxyflavone is extracted with solvent refluxing is 1-2h, preferably 1-
1.5h, more preferably 1.5h；
Preferably, it is described that the raw material containing polymethoxyflavone is repeated into refluxing extraction 2-5 times with solvent, preferably extract 3-5 times,
Further preferably extract 3 times, merge gained extract solution, obtain polymethoxyflavone extract solution.
7. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that by stirring extraction gained
Organic layer be washed to pH for 7-7.5；
Preferably, the washing water consumption is 0.1-0.4 times of material quality, preferably 0.1-0.2 times of material quality, enters one
Step is preferably 0.1 times；
Preferably, the number of times of the washing is 2-5 times, more preferably preferably 2-3 times, 2 times.
8. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that described to contain many methoxies
The raw material of base flavones includes rutaceae fruit, preferably includes Ponkan, further preferably includes Ponkan young fruit.
9. the preparation method of a kind of polymethoxyflavone according to claim 1, it is characterised in that by polymethoxyflavone
Filter, dry, obtain polymethoxyflavone product；
Preferably, the temperature of the drying is 40-80 DEG C, more preferably preferably 40-60 DEG C, 60 DEG C.
10. prepared using a kind of preparation method of polymethoxyflavone described in claim 1-9 any claims
Polymethoxyflavone product.
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| CN104902764A (en) * | 2012-10-12 | 2015-09-09 | 国立大学法人琉球大学 | Method for manufacturing substance containing nobiletin and tangeretin derived from citrus fruits, and nobiletin- and tangeretin-containing substance obtained thereby |
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