CN105726600A - Method for extracting and purifying flavones and phenolic acids in medicinal material ixeris sonchifolia through metal ion chelation - Google Patents
Method for extracting and purifying flavones and phenolic acids in medicinal material ixeris sonchifolia through metal ion chelation Download PDFInfo
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- CN105726600A CN105726600A CN201610288119.2A CN201610288119A CN105726600A CN 105726600 A CN105726600 A CN 105726600A CN 201610288119 A CN201610288119 A CN 201610288119A CN 105726600 A CN105726600 A CN 105726600A
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- China
- Prior art keywords
- metal ion
- extraction
- chelant
- phenolic acids
- organic solvent
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- 238000000034 method Methods 0.000 title claims abstract description 34
- 229930003944 flavone Natural products 0.000 title claims abstract description 24
- 235000011949 flavones Nutrition 0.000 title claims abstract description 24
- 150000007965 phenolic acids Chemical class 0.000 title claims abstract description 19
- 241001301715 Crepidiastrum sonchifolium Species 0.000 title claims abstract description 17
- 235000009048 phenolic acids Nutrition 0.000 title claims abstract description 16
- 229910021645 metal ion Inorganic materials 0.000 title abstract description 8
- 239000000463 material Substances 0.000 title abstract description 4
- 230000009920 chelation Effects 0.000 title abstract 5
- 150000002213 flavones Chemical class 0.000 title abstract 4
- 238000000605 extraction Methods 0.000 claims abstract description 26
- 239000013522 chelant Substances 0.000 claims abstract description 21
- 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 claims abstract description 20
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- 150000002212 flavone derivatives Chemical class 0.000 claims abstract description 19
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 239000000284 extract Substances 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000000746 purification Methods 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- 159000000003 magnesium salts Chemical class 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 6
- 238000013461 design Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
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- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 2
- 239000000292 calcium oxide Substances 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 239000002537 cosmetic Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 229910052738 indium Inorganic materials 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 claims description 2
- 229910001950 potassium oxide Inorganic materials 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims description 2
- 229910001948 sodium oxide Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- -1 phenolic acid compounds Chemical class 0.000 abstract description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 3
- 238000004090 dissolution Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 238000012545 processing Methods 0.000 abstract description 2
- 238000011084 recovery Methods 0.000 abstract 1
- 235000013824 polyphenols Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 4
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 4
- 229930003935 flavonoid Natural products 0.000 description 4
- 150000002215 flavonoids Chemical class 0.000 description 4
- 235000017173 flavonoids Nutrition 0.000 description 4
- VSUOKLTVXQRUSG-ZFORQUDYSA-N luteolin 7-O-beta-D-glucosiduronic acid Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=C(O)C(O)=CC=3)OC2=C1 VSUOKLTVXQRUSG-ZFORQUDYSA-N 0.000 description 4
- 229910001425 magnesium ion Inorganic materials 0.000 description 4
- YDDGKXBLOXEEMN-UHFFFAOYSA-N Di-E-caffeoyl-meso-tartaric acid Natural products C=1C=C(O)C(O)=CC=1C=CC(=O)OC(C(O)=O)C(C(=O)O)OC(=O)C=CC1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-UHFFFAOYSA-N 0.000 description 3
- YDDGKXBLOXEEMN-IABMMNSOSA-N chicoric acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-IABMMNSOSA-N 0.000 description 3
- 229930016920 cichoric acid Natural products 0.000 description 3
- YDDGKXBLOXEEMN-WOJBJXKFSA-N dicaffeoyl-L-tartaric acid Natural products O([C@@H](C(=O)O)[C@@H](OC(=O)C=CC=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)C=CC1=CC=C(O)C(O)=C1 YDDGKXBLOXEEMN-WOJBJXKFSA-N 0.000 description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- JBFOLLJCGUCDQP-ZFORQUDYSA-N Apigenin 7-glucuronide Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CC(O)=C2C(=O)C=C(C=3C=CC(O)=CC=3)OC2=C1 JBFOLLJCGUCDQP-ZFORQUDYSA-N 0.000 description 2
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- 150000003505 terpenes Chemical class 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical class OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/331—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using water, e.g. cold water, infusion, tea, steam distillation, decoction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
Abstract
The invention belongs to technical the field of medicine and relates to the extraction of flavone and phenolic acid compounds from a medicinal material ixeris sonchifolia through a metal ion chelation process. A method for extracting and purifying flavones and phenolic acids in a medicinal material ixeris sonchifolia through metal ion chelation is characterized by comprising the following steps: (1) extraction; (2) solvent recovery and moisture removal; (3) dissolution in an organic solvent and filtering; (4) metal ion chelation; and (5) filtering and drying to obtain the product. The feature that flavones and phenolic acids often have o-diphenol hydroxyl or adjacent hydroxyl and carbonyl structures and can be chelated with metal ions is conducive to the chelation reaction in a certain alkalinity range, and the chelate can be precipitated in the organic solvent and separated out. The extraction technology of ixeris sonchifolia flavones is simplified, the extraction period is shortened, the technology is simple and easy to understand, and the production cost can be reduced; and moreover, the product has stable quality, loose property and good fluidity and facilitates further preparation processing.
Description
Technical field
The invention belongs to pharmaceutical technology field, relate to using metal ion-chelant method from Herba Ixeritis Sonchifoliae (Herba Ixeritis Sonchifoliae) medical material
Middle extraction flavone and phenolic acid compound.
Background technology
Chinese medicine Herba Ixeritis Sonchifoliae is Compositae gutweed platymiscium Herba Ixeritis Sonchifoliae Ixeris sonchifolia (Bge) Hance
It is dried herb, there is heat-clearing and toxic substances removing, removing heat from blood and promoting blood circulation, effect of evacuation of pus pain relieving.Containing flavonoid, phenolic acids and sesquialter in Herba Ixeritis Sonchifoliae
The effective ingredient such as terpenoid.By the KUDIEZI ZHUSHEYE that modern crafts are refined, it is clinically used for treating coronary heart disease, apoplexy, myocardial infarction
And cerebrovascular disease, research shows, Herba Ixeritis Sonchifoliae flavone and phenolic acids have good protective effect to cardiovascular.In Herba Ixeritis Sonchifoliae
It is the glucosides class as aglycon with luteolin and apigenin that flavone compound mainly has, and mainly has luteolin-7-O-β-D-
Glucuronide (Luteolin-7-O-β-D-glucuronide, LGU), luteolin-7-O-β-D-Glucose glycosides
(Luteolin-7-O-β-D-glucoside), luteolin-7-O-β-D-Glucose-(1 → 2) glucoside (Luteolin-
7-O-β-D-glucosyl-(1 → 2)-β-D-glucoside), api-genin-7-O-β-D-glucoside (Apigenin-7-O-
β-D-glucoside)), apigenin-7-O-β-D-glucuronide (Apigenin-7-O-β-D-glucuronide) etc.,
Wherein LGU content in Ixeris sonchifolia Hance is the highest, and phenolic acids is with caffeic acid derivative as representative, and what content was higher has chicoric acid
(Cichoric acid), single coffee acyl group tartaric acid (Caffeoyltartaric acid) and chlorogenic acid etc.
(Chlorogenic acid).(Wu Jingjing etc., Herba Ixeritis Sonchifoliae chemical composition and the progress of pharmacological action, " the Tianjin traditional Chinese medical science
Medicine ", 04 phase in 2015).The method for extraction and purification of known Herba Ixeritis Sonchifoliae flavone and phenolic acid compound mainly has water or organic molten
(Ma Zhanzhi etc., Lxeris sonchifolia (bunge) hance flavone extract and preparation method and application, China is specially for agent extraction, column chromatography absorb-elute etc.
Profit, CN200810012647.0；Ma Zhanzhi etc., a kind of Herba Ixeritis Sonchifoliae total phenolics and preparation method thereof, Chinese patent, CN
201110001528.7), but there is the problems such as time-consuming, laborious, power consumption, consumption of organic solvent are big in said method.
Summary of the invention
The present invention is directed to existing extraction Herba Ixeritis Sonchifoliae flavone and phenolic acid method exists that complex process, step be many, extracting cycle
Longer deficiency and flavone and the method for phenolic acids during fast and convenient metal ion-chelant extraction purification Ixeris sonchifolia Hance is provided,
Improve the performance of product.
The technical solution of the present invention is: flavone and phenolic acid in a kind of metal ion-chelant extraction purification Ixeris sonchifolia Hance
The method of class, it is characterised in that step is as follows: (1) extracts, (2) recycling design and remove moisture removal, and (3) are dissolved in organic solvent also
Filtering, (4) metal ion-chelant, (5) are filtered, are dried, and to obtain final product.Describe in detail as follows:
Step (1) extract use method and solvent include but not limited to: water extraction, potass extraction, alcohol extraction, alcohol water extraction,
Water extract-alcohol precipitation, alcohol extracting-water precipitating；Or described alcohol is ethanol or methanol.
Step (2) recycling design and go the moisture removal to be: step (1) is extracted gained extracting solution use reclaim under negative pressure organic
Solvent, after organic solvent eliminates, continues to use the method for drying under reduced pressure or spray drying to remove moisture, obtains dry extraction
Thing.
Step (3) is dissolved in organic solvent and filtration is: will be completely dissolved in through the dry extract of step (2) gained
Organic solvent, and filter；The organic solvent used includes but not limited to: methanol, ethanol, ethyl acetate, acetone, butanone,
Ethylene glycol, propylene glycol, glycerol, isopropanol, 1-propanol, n-butyl alcohol, 2-butanol, oxolane, dimethyl sulfoxide, dimethyl methyl
Amide and their mixture；Or preferably methanol, ethanol.
Step (4) metal ion-chelant is: slaine directly or adds after being dissolved in solvent the filtrate of step (3) gained
In, be sufficiently stirred for, and add alkaline reagent regulation pH8-11, stand, to be precipitated completely after, filter；Slaine used includes
Magnesium, zinc, the salt of calcium, preferably magnesium salt, Mg2+Purification be better than Ca2+、Zn2+.Alkaline reagent includes but not limited to: hydrogen-oxygen
Change sodium, potassium hydroxide, calcium oxide, sodium oxide, potassium oxide, ammonia；Or preferably potassium hydroxide, sodium hydroxide.Flavone and phenolic acid
Class is generally of adjacent two phenolic hydroxyl groups, or neighbouring carbonyl, carboxyl, hydroxyl structure, can chelate with metal ion, necessarily
Alkaline range in contribute to this chelatropic reaction, chelate can precipitate in organic solvent, and is separated.
Products obtained therefrom can be directly used for the preparation of non-injection administration, food or the cosmetics such as oral, the external of preparation.
The method have the advantages that: 1, utilize flavone and phenolic acids to be generally of adjacent two phenolic hydroxyl groups, or neighbouring hydroxyl, carbonyl is tied
Structure, can occur the characteristic of chelating with metal ion, contribute to this chelatropic reaction in certain alkaline range, and chelate can be
Organic solvent precipitates, and is separated.2, simplify the extraction process step of Herba Ixeritis Sonchifoliae flavone, shorten extracting cycle,
Technique is simply prone to grasp, it is possible to decrease production cost, products obtained therefrom steady quality, and character is loose, good fluidity, it is easy to further
Preparation processing.
Accompanying drawing explanation
Fig. 1 is content and the rate of transform of LGU and CCA in magnesium salt chelating method extract.
Fig. 2 is content and the rate of transform of LGU and CCA in calcium salt chelating method extract.
Fig. 3 is content and the rate of transform of LGU and CCA in zinc salt chelating method extract.
Fig. 4 is the infared spectrum of Herba Ixeritis Sonchifoliae 50% ethanol extraction.
Fig. 5 is the fourier infrared collection of illustrative plates of the magnesium salt chelate of Herba Ixeritis Sonchifoliae 50% ethanol extract.
In order to further illustrate the essence of the present invention, specific embodiment is as follows.
Detailed description of the invention
Embodiment 1: HPLC-UV method detection luteolin-7-O-β-D-Glucose aldehydic acid glycosides (LGU) and chicoric acid in sample
(CCA).
Employing high performance liquid chromatography detects, and chromatograph and chromatographic condition are as follows: SHIMADZU LC-2010A(enters automatically
Sample device, column oven, quaternary pump, UV detector, Class-VP operating system)；Chromatographic column: Utimate AQ C-18 post
(250mm × 4.6mm, 5 μm, Welch Materrials Inc.)；Flowing phase: A: methanol-oxolane (volume ratio=15:
1)；B: water (1% formic acid), uses gradient elution program, 0-45min:30% A；45-52min:80% A；52-60min:30% A；
Flow velocity is 1mL/min, and column temperature is 40 DEG C, and detection wavelength is 348nm, sample size 10 μ L.
Calculate the foundation of standard curve.
Accurately weigh LGU, CCA standard substance after vacuum drying appropriate, dissolve with chromatograph methanol, obtain the storage of hybrid standard product
Standby liquid, precision draws hybrid standard product storing solution respectively, becomes the hybrid standard product solution of variable concentrations with methanol dilution, presses
2.2.1 liquid-phase condition is analyzed, and measures.With mass concentration ρ (μ g/mL) as abscissa, peak area (A) is that vertical coordinate draws mark
Directrix curve, the regression equation of LGU is: ρ-10569, A=21059, R2=0.9990, show in the range of 2.5-20 μ g/ mL
Linear good.The regression equation of CCA: A=3E+07 ρ-26569.
The mensuration of sample size.Sample about 100.0 mg after precision weighs vacuum drying puts in tool plug conical flask, adds
60 mL methanol and 0.1mL glacial acetic acid ultrasonic dissolution assisting (frequency: 40kHz, power: 70W, time: 15min), transfer solution is extremely
100mL measuring bottle, washs conical flask in three times with 40mL methanol, and shift cleaning mixture to after measuring bottle by methanol constant volume to scale, shake
Even, with aperture 0.45 μm PTFE filter filtering solution, take subsequent filtrate and detect LGU, CCA according to chromatographic condition, and calculate content
And the rate of transform.Computing formula is as follows:
Pi(%)=Wi/ Wmp× 100 (1).
Pmlgu: the weight/mass percentage composition of LGU or CCA in precipitated metal thing；Wi: the matter of LGU or CCA in precipitated metal thing
Amount；Wmp: it is dried the quality of precipitated metal thing.
Ti(%)=Wi/ Wi0 × 100 (2).
Ti: in precipitation process, LGU or CCA is transferred to the percentage rate in precipitate by raw extract；Wi0: raw material carries
Take LGU or CCA mass in thing.
Embodiment 2
Different metal ION Mg2+、Ca2+、Zn2+To flavonoid (with LGU as representative) and the purification of phenolic acids (with CCA as representative)
Technique and result.
Ixeris sonchifolia Hance 1kg, respectively with 15, the alcohol reflux of the 50% of 12 times amount 2 times, each 1h.United extraction
Liquid, decompression recycling ethanol is to without alcohol taste, and gained suspension spray drying method is dried, and collects products obtained therefrom, moistureproof standby.Accurate
Weighing dried Herba Ixeritis Sonchifoliae extract appropriate, being configured to concentration with methanol through supersonic oscillations is 1mg/mL solution, filters standby
With.Take Herba Ixeritis Sonchifoliae filtrate 100ml, be added thereto to 0.1mol/L slaine (MgCl2, CaCl2、ZnCl2) methanol solution fit
Amount, shake well is after 15 minutes, and the NaOH solution of dropping 1mol/L regulates solution ph, and regulation solution ph is 8.0 respectively,
9.0,9.5,10.0,11.0, under the conditions of 4 DEG C, place 4h after being sufficiently stirred for, filter, precipitate and rinse through 10ml methanol, rinse two
Put into (vacuum: 2.67kPa), at room temperature drying under reduced pressure 24h in vacuum drying oven after secondary, obtain precipitated metal thing, weigh.
Gained precipitated metal thing is measured the content of LGU and CCA by embodiment 1, and calculates the rate of transform.
In magnesium salt chelating method gained Herba Ixeritis Sonchifoliae extract, when pH value is 9-9.5, gained LGU Yu CCA and they and
Under the conditions of height, especially pH9, the content of LGU is up to 11.7%(accompanying drawing 1).During with calcium salt for chelating agen, gained in the range of pH8-11
LGU and CCA total amount more stable (accompanying drawing 2).With zinc ion as chelating agen, in the range of pH 8-9.5, gained LGU and CCA contains
Measure higher (accompanying drawing 3).Mg2+Purification be better than Ca2+、Zn2+。
Embodiment 3
Fourier transform infrared spectrometry (FT-IR).
Weigh appropriate drying under reduced pressure sample respectively, tabletting after mixing with dry KBr, with infrared spectrometer (IFS-55,
Bruker company, Germany) measure Fourier infrared spectrum, sweep limits: 4000-400cm-1。
Herba Ixeritis Sonchifoliae ethanol 50% extract, Herba Ixeritis Sonchifoliae extract magnesium ion precipitate (pH9) infared spectrum are as shown in Figure 4,5.
Hydroxyl vibration peak is had to be formed near 3427.1628-1629,1384 cm-1Neighbouring is the asymmetric of carbonyl and symmetrical stretching vibration
Peak, 1264 and 1068 cm-1It is the asymmetric of C-O-C group and symmetrical stretching vibration absworption peak.1115-1121 cm-1It is
C-O absworption peak.The absworption peak scope of MgO is 500-1000 cm-1, peak value is at 860 cm-1.1500cm in Fig. 5-1Neighbouring shakes
Dynamic peak strengthens explanation, and aromatic rings class content of material increased, i.e. flavone and polyphenol content improves.
Embodiment 4
The preparation of Herba Ixeritis Sonchifoliae magnesium salt chelate tablet.
Extract Ixeris sonchifolia Hance by embodiment 2 method, and with magnesium salt as chelating agen, sodium hydroxide regulation pH is 9, and it is heavy to collect
Shallow lake thing, is dried, and pulverized 80 mesh sieves, and after mixing with appropriate lactose, compressing dry granulation is pelletized.Granule and the magnesium stearate of 1%, 1%
Aerosil200# mixing after, tabletting according to known methods.
Embodiment 5
With the Herba Ixeritis Sonchifoliae further refined total flavonoids of magnesium salt chelate and total phenolics.
According to the method for embodiment 2, employing magnesium chloride is chelating agen, and Herba Ixeritis Sonchifoliae extracting concentration is adjusted to 10mg/ml, pH
=9, gained precipitate adds 6 times amount water dissolutioies, and to regulate pH be 3, extracts 5 times with the ethyl acetate of two volumes, merges acetic acid
Ethyl ester extract, recycling design, gained dried object measures LGU and CCA content by embodiment 1 method.Content is respectively 38.9% He
33.8%.What gained refined total flavonoids total phenolics can be used for injection prepares raw material.
Claims (6)
1. flavone and the method for phenolic acids in a metal ion-chelant extraction purification Ixeris sonchifolia Hance, it is characterised in that step is such as
Under: (1) extracts, (2) recycling design and remove moisture removal, and (3) are dissolved in organic solvent and filter, (4) metal ion-chelant, (5)
Filter, be dried, to obtain final product.
2. flavone and the method for phenolic acids in metal ion-chelant extraction purification Ixeris sonchifolia Hance as claimed in claim 1, its
It is characterised by that step (1) extracts the method used and solvent includes but not limited to: water extraction, potass extraction, alcohol extraction, alcohol water
Extraction, water extract-alcohol precipitation, alcohol extracting-water precipitating；Or described alcohol is ethanol or methanol.
3. flavone and the method for phenolic acids in metal ion-chelant extraction purification Ixeris sonchifolia Hance as claimed in claim 1, its
Be characterised by step (2) recycling design and go the moisture removal to be: step (1) is extracted gained extracting solution use reclaim under negative pressure organic
Solvent, after organic solvent eliminates, continues to use the method for drying under reduced pressure or spray drying to remove moisture, obtains dry extraction
Thing.
4. flavone and the method for phenolic acids in metal ion-chelant extraction purification Ixeris sonchifolia Hance as claimed in claim 1, its
It is characterised by that step (3) is dissolved in organic solvent and filtration is: will be completely dissolved in through the dry extract of step (2) gained
Organic solvent, and filter；The organic solvent used includes but not limited to: methanol, ethanol, ethyl acetate, acetone, butanone,
Ethylene glycol, propylene glycol, glycerol, isopropanol, 1-propanol, n-butyl alcohol, 2-butanol, oxolane, dimethyl sulfoxide, dimethyl methyl
Amide and their mixture；Or preferably methanol, ethanol.
5. flavone and the method for phenolic acids in metal ion-chelant extraction purification Ixeris sonchifolia Hance as claimed in claim 1, its
It is characterised by that step (4) metal ion-chelant is: slaine directly or is added after being dissolved in solvent the filtrate of step (3) gained
In, be sufficiently stirred for, and add alkaline reagent regulation pH8-11, stand, to be precipitated completely after, filter；Slaine used includes
Magnesium, zinc, the salt of calcium, preferably magnesium salt；Alkaline reagent includes but not limited to: sodium hydroxide, potassium hydroxide, calcium oxide, sodium oxide,
Potassium oxide, ammonia；Or preferably potassium hydroxide, sodium hydroxide.
6., such as flavone and the method for phenolic acids in claim 1 metal ion-chelant extraction purification Ixeris sonchifolia Hance, its feature exists
Can be directly used for preparing oral, the preparation of external non-injection administration, food or cosmetics in products obtained therefrom.
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Application publication date: 20160706 |