CN106008627B - The preparation and anti-aging purposes of polygonum capitatum flavonoid glycoside compound - Google Patents
The preparation and anti-aging purposes of polygonum capitatum flavonoid glycoside compound Download PDFInfo
- Publication number
- CN106008627B CN106008627B CN201610410464.9A CN201610410464A CN106008627B CN 106008627 B CN106008627 B CN 106008627B CN 201610410464 A CN201610410464 A CN 201610410464A CN 106008627 B CN106008627 B CN 106008627B
- Authority
- CN
- China
- Prior art keywords
- polygonum capitatum
- ethyl acetate
- methanol
- flavonoid glycoside
- post separation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 241000764065 Persicaria capitata Species 0.000 title claims abstract description 23
- 229930182486 flavonoid glycoside Natural products 0.000 title claims abstract description 20
- -1 flavonoid glycoside compound Chemical class 0.000 title claims abstract description 20
- 230000003712 anti-aging effect Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 238000000926 separation method Methods 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 8
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- 230000036541 health Effects 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 22
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 16
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 11
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 11
- 235000005875 quercetin Nutrition 0.000 claims description 11
- 229960001285 quercetin Drugs 0.000 claims description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 7
- 150000008265 rhamnosides Chemical class 0.000 claims description 7
- 238000001514 detection method Methods 0.000 claims description 6
- 150000007955 flavonoid glycosides Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 210000000692 cap cell Anatomy 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- SOSLMHZOJATCCP-AEIZVZFYSA-N afzelin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC1=C(C=2C=CC(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O SOSLMHZOJATCCP-AEIZVZFYSA-N 0.000 claims 1
- SOSLMHZOJATCCP-PADPQNGGSA-N afzelin Natural products O([C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](C)O1)C1=C(c2ccc(O)cc2)Oc2c(c(O)cc(O)c2)C1=O SOSLMHZOJATCCP-PADPQNGGSA-N 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
- HEAQNIWCWRHODF-UHFFFAOYSA-N kaempferol 3-O-alpha-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=C(C=2C=CC=CC=2)OC2=CC(O)=CC(O)=C2C1=O HEAQNIWCWRHODF-UHFFFAOYSA-N 0.000 claims 1
- LPEPTRFUOKMJCH-UHFFFAOYSA-N myricetin 7-O-alpha-L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(=O)C(O)=C(C=3C=C(O)C(O)=C(O)C=3)OC2=C1 LPEPTRFUOKMJCH-UHFFFAOYSA-N 0.000 claims 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 abstract description 14
- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 13
- 239000003814 drug Substances 0.000 abstract description 5
- 238000000605 extraction Methods 0.000 abstract description 3
- 230000000975 bioactive effect Effects 0.000 abstract description 2
- 239000000945 filler Substances 0.000 abstract description 2
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000003808 methanol extraction Methods 0.000 abstract 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000377 silicon dioxide Substances 0.000 abstract 1
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 230000032683 aging Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 description 5
- IKMDFBPHZNJCSN-UHFFFAOYSA-N Myricetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC(O)=C(O)C(O)=C1 IKMDFBPHZNJCSN-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 235000008777 kaempferol Nutrition 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 description 5
- PCOBUQBNVYZTBU-UHFFFAOYSA-N myricetin Natural products OC1=C(O)C(O)=CC(C=2OC3=CC(O)=C(O)C(O)=C3C(=O)C=2)=C1 PCOBUQBNVYZTBU-UHFFFAOYSA-N 0.000 description 5
- 235000007743 myricetin Nutrition 0.000 description 5
- 229940116852 myricetin Drugs 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001425 electrospray ionisation time-of-flight mass spectrometry Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000001888 Peptone Substances 0.000 description 2
- 108010080698 Peptones Proteins 0.000 description 2
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 235000019319 peptone Nutrition 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229940016667 resveratrol Drugs 0.000 description 2
- 235000021283 resveratrol Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000255581 Drosophila <fruit fly, genus> Species 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- HRAYYNRXNPLKFE-UHFFFAOYSA-N L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1C(O)C(OC2C(C(C)OC(OC=3C=C4C(C(C(OC5C(C(OC6C(C(O)C(O)C(C)O6)O)C(O)C(COC6C(C(O)C(O)C(CO)O6)O)O5)OC(=O)C=CC=5C=CC(O)=CC=5)=C(C=5C=CC(O)=CC=5)O4)=O)=C(O)C=3)C2O)OC(=O)C=CC=2C=CC(O)=CC=2)OC(C)C1O HRAYYNRXNPLKFE-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000219050 Polygonaceae Species 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 206010044565 Tremor Diseases 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000009193 crawling Effects 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000007919 dispersible tablet Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 229940040145 liniment Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 208000030194 mouth disease Diseases 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 230000000955 neuroendocrine Effects 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960000502 poloxamer Drugs 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000000130 stem cell Anatomy 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention provides a kind of preparation method of polygonum capitatum flavonoid glycoside compound, it is crushed by polygonum capitatum, methanol extraction, filter concentration, after water and ethyl acetate solvent distribution, ethyl acetate concentration, first passes through silica gel post separation, obtains using ODS (octadecylsilane chemically bonded silica filler) opening column and HPLC (high performance liquid chromatography) purifying.For the present invention by saccharomyces cerevisiae K6001 bioactive systems, the replicability service life of yeast can significantly be extended by showing this four flavonoid glycoside compounds.Polygonum capitatum flavonoid glycoside compound provided by the invention can be applied in preparing antiaging agent or health care product.Preparation method of the present invention is simple, and the product purity of extraction is high, and polygonum capitatum is the cheap Chinese medicine that is easy to get, and increases the medicinal usage of polygonum capitatum, it was found that anti-aging potentiality possessed by its component.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to the preparation method of polygonum capitatum flavonoid glycoside reactive compound and its
Preparing the application in antiaging agent.
Background technique
According to recent statistics data, the whole world 60 years old and the above aged had reached 9.01 hundred million in 2015, accounted for
The 12% of total world population.The world has entered aging society, and the following disease relevant to aging becomes increasingly prominent
The problem of.Neurodegenerative disease including Alzheimer disease is one of global public health problem.Only in
State, the aged already exceed 200,000,000, and the patient populations of Alzheimer disease are in 2014 more than 6,000,000.It is led in medicine and pharmacology
Domain, the drug for finding prevention and treatment geriatric disease have become the task of top priority.
By studying for a long period of time to Aging mechanism, a variety of causes of senescence have been formed in the art, including programmed aging is said, body
Cell mutation is said, mistake is caused disaster, and free radical is said, neuroendocrine is said, immunosenescence is said, etc..Aging is one very multiple
Miscellaneous process, the mode that same class antiaging agent plays drug effect are also not quite similar.
Polygonaceae plant polygonum capitatum (Polygonum capitatum) is perennial draft of crawling, and is that one of seedling medicine is normal
With medicinal material, there is very high medical value.As the common herbal medicine of Guizhou nationality, the also existing research of the medical value of polygonum capitatum:
Herba Polygoni Capitati extract and its application in hypoglycemic drug；Application and whitening of the Herba Polygoni Capitati extract in whitening articles are used
Product；Relinqing Granula raw material Herba Polygoni Capitati extract with anti-inflammatory effect；Relinqing Granula raw material with anti-gonococcus effect
Herba Polygoni Capitati extract；For preventing or treating the polygonum capitatum composition of whelk；For treating or preventing the headdress flower of mouth disease
Knotweed composition.
Summary of the invention
The object of the present invention is to provide a kind of preparation methods of polygonum capitatum flavonoid glycoside reactive compound, pass through following steps
It prepares:
(1) polygonum capitatum is extracted after crushing with methanol, uses ethyl acetate and aqueous solvent distribution, ethyl acetate again after filtering concentration
Layer concentration, obtains ethyl acetate layer study；
(2) by gained ethyl acetate layer study successively through silica gel opening post separation and twice ODS be open post separation, obtain two
A anti-aging active ingredients；
(3) resulting two anti-aging active ingredients obtain four flavonoid glycoside reactive compounds through HPLC after purification, point
Not Wei myricetin 7-O--L-rhamnopyranoside, quercetin 4'-O- α-L-rhamnopyranoside,
Quercetin 3-O- α-(2 "-galloyl) rhamnoside, and kaempferol 3-O--L-rhamnopyranoside.
The solvent system of silica gel opening post separation is n-hexane: dichloro=100 in step (2): 0,90: 10,70: 30,50:
50,30: 70,10: 90,0: 100；Subsequent methylene chloride: ethyl acetate=90: 10,70: 30,50: 50,30: 70,0: 100；Most
It is eluted afterwards for methanol.The solvent system of first time ODS opening post separation is methanol: water=30: 70,35: 65,40: 60,50: 50,
60: 40,70: 30,90: 10,100: 0.The solvent system of second of ODS opening post separation is methanol: water=30: 70,
50: 50 and 30: 70,35: 65,60: 40.
The chromatographic condition that HPLC is purified in step (3) is respectively as follows: chromatographic column CAPCELL PAKC18 (10/250mm), flow velocity
3mL/min, Detection wavelength 210nm, mobile phase methanol: water=38: 62 and chromatographic column Develosil C30-UG-5 (10/
250mm), Nomura Chemical, flow velocity 3mL/min, Detection wavelength 210nm, mobile phase methanol: water=48: 52.
It is a further object to provide the flavonoid glycoside compounds to prepare antiaging agent or health care product
In application.The research of the invention finds that the flavonoid glycoside compound in the polygonum capitatum source obtained by the method for the invention is anti-ageing
In old model, it can significantly extend the yeast replicability service life (see Fig. 1), especially four flavonoid glycoside compounds.Illustrate its tool
There is activity of fighting against senium.
The flavonoid glycoside compound in polygonum capitatum source provided by the invention can be prepared according to any conventional process pharmaceutically may be used
The carrier or diluent of receiving.Pharmaceutically acceptable carrier described here refers to the pharmaceutical carrier of pharmaceutical field routine, example
Such as diluent, excipient are in this way, filler such as starch, sucrose, microcrystalline cellulose etc.；Adhesive such as starch slurry, hydroxypropyl fiber
Element, gelatin, polyethylene glycol etc.；Wetting agent such as magnesium stearate, superfine silica gel powder, polyethylene glycols etc.；The poly- sorb rouge of sorbefacient,
Lecithin etc., surfactant poloxamer, fatty acid sorbitan, poly- sorb rouge etc., in addition it can add in compound
Enter other adjuvants such as flavouring agent, sweetener etc..
The dosage form of administration can be tablet, pill, pulvis, dispersible tablet, sachets, elixir, suspension, emulsion, solution
Agent, syrup, aerosol, soft capsule, hard capsule, aseptic parenteral solution, liniment or suppository.It can be made into routine, quick-release is sustained or prolongs
Slowbreak is put.
Flavonoid glycoside compound of the invention can be given by all means, including oral, nasal cavity, muscle, subcutaneously, intravenous
Deng.
The flavonoid glycoside compound in polygonum capitatum source provided by the invention is shown significantly in saccharomyces cerevisiae K6001 system
Activity of fighting against senium.Preparation method of the present invention is simple, and the product purity of extraction is high, and polygonum capitatum is the cheap Chinese medicine that is easy to get, and is
The research and development of antiaging agent or health care product carry out basic research, will have important practical significance.
Detailed description of the invention
Fig. 1 is that four flavonoid glycoside compounds make yeast replicability life-time dilatation in K6001 bioactive systems
With；1:myricetin 7-O--L-rhamnopyranoside, 2:quercetin 4'-O- α-L- in figure
Rhamnopyranoside, 3:quercetin 3-O- α-(2 "-galloyl) rhamnoside, 4:kaempferol3-O--
L-rhamnopyranoside。
Specific embodiment
Below by way of to such several particular compound preparating example embodiment and attached drawing again to of the invention above-mentioned
Content is described in further detail, but the range that this should not be interpreted as to the above-mentioned theme of the present invention is only limitted to following examples,
The techniques implemented on the basis of the foregoing are all within the scope of the present invention.
Embodiment 1
The preparation method of four flavonoid glycoside compounds of separation and Extraction, specific steps from polygonum capitatum are as follows:
1) it crushes and extracts:
After 250g dry polygonum capitatum crushes, is extracted 2 times, 1 day every time, filtered dense at room temperature with 2.5L methanol (technical grade)
Contracting, obtains methanol extract study, with ethyl acetate and water extraction and separation, stands, and after ethyl acetate layer reduced pressure is spin-dried for, obtains
To ethyl acetate layer study 9g.
2) it separates and purifies:
By ethyl acetate layer study first through silica gel opening post separation (200-300 mesh, following solvent system by volume, just
Hexane: dichloromethane solvent system is by volume are as follows: 100: 0,90: 10,70: 30,50: 50,30: 70,10: 90,0: 100；With
Methylene chloride afterwards: ethyl acetate solvent system is by volume are as follows: 90: 10,70: 30,50: 50,30: 70,0: 100；It is finally first
Alcohol)；By active sample again with ODS opening post separation (solvent system is methanol by volume: water=0: 70,35: 65,40: 60,
50: 50,60: 40,70: 30,90: 10,100: 0)；Two active component As 1 (975.7mg) and B1 (267.4mg) are obtained, then
A1 and B1 respectively with ODS opening post separation (solvent system by volume be respectively methanol: water are as follows: 30: 70,50: 50 and 30: 70,
35: 65,60: 40), obtaining higher two active component As 2 (129.4mg) of purity and B2 (139.9mg).Take A2 50mg HPLC
Purifying, chromatographic condition: chromatographic column PAKC18(10/250mm), flow velocity 3ml/min, Detection wavelength 210nm, mobile phase are methanol:
Water=38: 62, obtaining compound myricetin7-O--L-rhamnopyranoside, (2.7mg, retention time are
19.5min), quercetin4'-O- α-L-rhamnopyranoside (35.8mg, retention time 38.0min)；Take B2
20mg is purified with HPLC, chromatographic condition: chromatographic column C30-UG-5 (10/250mm), flow velocity 3ml/min, Detection wavelength 210nm, stream
Dynamic is mutually methanol: water=48: 52, obtain compound quercetin 3-O- α-(2 "-galloyl) rhamnoside
(5.3mg, retention time 54.8min), kaempferol 3-O--L-rhamnopyranoside (2.5mg, retention time
For 60.6min).
Four flavonoid glycoside compound structural formulas are as follows:
Embodiment 2
To embodiment 1 gained compound myricetin 7-O--L-rhamnopyranoside, quercetin4'-O-
α-L-rhamnopyranoside, quercetin 3-O- α-(2 "-galloyl) rhamnoside, and kaempferol 3-O-
The physicochemical characteristics of-L-rhamnopyranoside and the Qualitative Identification of chemical structure:
Compound myricetin 7-O--L-rhamnopyranoside, quercetin4'-O- α-L-
Rhamnopyranoside, quercetin 3-O- α-(2 "-galloyl) rhamnoside, and kaempferol 3-O--L-
The structure of rhamnopyranoside is compared through 1H NMR, MS and document and is determined.
The physicochemical property of compound myricetin 7-O--L-rhamnopyranoside: yellow-brown solid, molecular formula
For C21H20O12；ESI-TOF-MS:m/z 465.1027 (M+H)+, hydrogen modal data:1HNMR(500MHz,CD3OD) :=6.95 (s,
2H), 6.37 (d, 1H, J=2.0Hz), 6.20 (d, 1H, J=2.0Hz), 5.31 (d, 1H, J=1.5Hz), 4.22 (dd, 1H, J
=3,1.5Hz), 3.79 (dd, 1H, J=9.0,3.0Hz), 3.52 (m, 1H), 3.32 (m, 1H), 0.96 (d, 3H, J=
6.5Hz)。
The physicochemical property of compound quercetin 4'-O- α-L-rhamnopyranoside: yellow-brown solid, molecular formula
For C21H20O11；ESI-TOF-MS:m/z 449.1114 (M+H)+, hydrogen modal data:1HNMR(500MHz,CD3OD) :=7.33 (d,
1H, J=1.5Hz), 7.30 (dd, 1H, J=8.0,1.5Hz), 6.90 (d, 1H, J=8.0Hz), 6.18 (d, 1H, J=
2.0Hz), 6.35 (d, 1H, J=2.0Hz), 5.34 (s, 1H), 4.21 (s, 1H), 3.39 (m, 1H), 3.73 (dd, 1H, J=
), 9.5,3.0Hz 3.43 (m, 1H), 0.93 (d, 3H, J=6.0Hz).
Compound quercetin 3-O- α-(2 "-galloyl) rhamnoside physicochemical property: yellow solid, molecule
Formula is C28H24O15；ESI-TOF-MS:m/z 601.1179 (M+H)+, hydrogen modal data:1HNMR(500MHz,CD3OD) :=7.36
(d, 1H, J=2.0Hz), 7.34 (dd, 1H, J=8.5,2.0Hz), 7.07 (s, 2H), 6.93 (d, 1H, J=85Hz), 6.18
(d, 1H, J=2.0Hz), 6.36 (d, 1H, J=2.0Hz), 5.63 (dd, 1H, J=3.5,2.0Hz), 5.50 (d, 1H, J=
1.5Hz), 4.01 (m, 1H), 3.47 (m, 2H), 1.03 (d, 3H, J=6.0Hz).
The physicochemical property of compound kaempferol 3-O--L-rhamnopyranoside: yellow-brown solid, molecular formula
For C21H20O10；ESI-TOF-MS:m/z 443.1125 (M+H)+, hydrogen modal data:1HNMR(500MHz,CD3OD) :=7.77 (d,
1H, J=8.5Hz), 6.93 (d, 1H, J=8.5Hz), 6.18 (d, 1H, J=2.0Hz), 6.35 (d, 1H, J=2.0Hz), 5.37
(d, 1H, J=1.5Hz), 4.21 (dd, 1H, J=3.0,1.5Hz), 3.70 (dd, 1H, J=9.0,3.5Hz), 3.33-3.16
(m, 2H), 0.92 (d, 3H, J=5.5Hz).
Embodiment 3
Four flavonoid glycoside compounds show activity of fighting against senium in anti-aging model discrimination, can significantly extend K6001
The replicability service life of yeast.
Biological model currently used for research on anti-senescence mainly has mouse, nematode, drosophila and yeast.The present embodiment selection is made
Active system of the brewer yeast as research on anti-senescence, because yeast is single celled eucaryote, life cycle is short, and it is complete to have obtained its
Whole genomic data is currently used aging model biology.Simultaneously using resveratrol as positive control, resveratrol is
Small molecule compound that is currently known, showing in several animal models anti-aging effects.
Analysis method the following steps are included:
(1) K6001 yeast strain is taken out from -30 DEG C of refrigerators, is washed three times with PBS, each 5ml removes glycerol therein.
Be eventually adding 1ml PBS, blow and beat, make its suspend after be added to 5ml fluid nutrient medium (1% yeast powder, 2% peptone,
3% galactolipin) in.28 DEG C of shakings (160r/min) are cultivated 24 hours；
(2) it is washed three times after cultivating with 5ml PBS, removes fluid nutrient medium therein, counted with blood counting chamber,
Calculate the concentration of yeast；
(3) solvent is made using dehydrated alcohol, respectively prepares 1 μM, 3 μM, it is spare；
(4) in sterilized culture dish be added 5ml solid medium (1% yeast powder, 2% peptone, 2%
Glucose, 2% agar powder), after culture medium solidification after, be separately added into prepared sample in step (3), solvent thereto
After volatilization be added 4000 yeast, with spreader smear uniformly, 28 DEG C constant temperature incubation 48 hours；
(5) every ware counts the daughter cell number that 40 mother cells generate respectively at random under microscope, and records, maps and divide
Analysis, the result is shown in Figure 1.
Claims (1)
1. a kind of preparation method for antiaging agent or the polygonum capitatum flavonoid glycoside compound of health care product, the polygonum capitatum is yellow
Ketone glycosides compound is respectively myricetin 7-O- α-L-rhamnopyranoside, quercetin 4'-O- α-L-
Rhamnopyranoside, quercetin 3-O- α-(2''-galloyl) rhamnoside, and kaempferol 3-O-
α-L-rhamnopyranoside, which is characterized in that realized by following preparation step:
(1) polygonum capitatum is extracted after crushing with methanol, is filtered after being concentrated, then is distributed with ethyl acetate and aqueous solvent, ethyl acetate layer
Concentration, obtains ethyl acetate layer study；
(2) gained ethyl acetate layer study is successively open post separation through silica gel opening post separation and twice ODS, obtain two it is anti-
Aging active component；
(3) resulting two anti-aging active ingredients obtain four flavonoid glycoside reactive compounds through HPLC after purification；
Wherein the solvent system of silica gel opening post separation is n-hexane: methylene chloride=100 in step (2): 0,90: 10,70:
30,50: 50,30: 70,10: 90,0: 100；Subsequent methylene chloride: ethyl acetate=90: 10,70: 30,50: 50,30: 70,
0:100；Finally eluted for methanol；The solvent system of first time ODS opening post separation is methanol: water=30: 70,35: 65,40:
60,50: 50,60: 40,70: 30,90: 10,100: 0；The solvent system of second of ODS opening post separation is methanol: water
=30: 70,50: 50 and 30: 70,35: 65,60: 40；
The chromatographic condition that HPLC is purified in step (3) is respectively as follows: chromatographic column CAPCELL PAKC18,10/250 mm, flow velocity 3
ML/min, 210 nm of Detection wavelength, mobile phase methanol: water=38: 62 and chromatographic column Develosil C30-UG-5,10/250
Mm, Nomura Chemical, 3 mL/min of flow velocity, 210 nm of Detection wavelength, mobile phase methanol: water=48: 52.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610410464.9A CN106008627B (en) | 2016-06-12 | 2016-06-12 | The preparation and anti-aging purposes of polygonum capitatum flavonoid glycoside compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610410464.9A CN106008627B (en) | 2016-06-12 | 2016-06-12 | The preparation and anti-aging purposes of polygonum capitatum flavonoid glycoside compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106008627A CN106008627A (en) | 2016-10-12 |
| CN106008627B true CN106008627B (en) | 2019-02-05 |
Family
ID=57090239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610410464.9A Active CN106008627B (en) | 2016-06-12 | 2016-06-12 | The preparation and anti-aging purposes of polygonum capitatum flavonoid glycoside compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106008627B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114689729B (en) * | 2020-12-31 | 2023-05-12 | 鲁南制药集团股份有限公司 | Detection method of flavonoid glycoside component in Jingfeng particles |
| CN114249782B (en) * | 2022-01-05 | 2023-06-30 | 湖南大学 | Prodrug for selectively destroying lysosomes of senescent cells as well as preparation method and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102653537A (en) * | 2012-05-17 | 2012-09-05 | 中国人民解放军第九七医院 | Method for extracting and preparing high-purity silibinin from polygonum capitatum herb |
-
2016
- 2016-06-12 CN CN201610410464.9A patent/CN106008627B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102653537A (en) * | 2012-05-17 | 2012-09-05 | 中国人民解放军第九七医院 | Method for extracting and preparing high-purity silibinin from polygonum capitatum herb |
Non-Patent Citations (6)
| Title |
|---|
| A flavonol glycoside from Myrsine africana leaves;LAWRENCE O，等;《Phytochemistry》;19961130;第43卷(第5期);1107-1109 |
| Comparative analysis of bioactivities of four Polygonum species.;Wu-Yang Huang，等;《Planta Medica》;20071207;第74卷(第1期);43-49 |
| 头花蓼化学成分研究;赵焕新，等;《天然产物研究与开发》;20110228;第23卷(第2期);262-266 |
| 头花蓼地上部分的化学成分研究;王洪平，等;《中草药》;20130131;第44卷(第1期);第25-26页 2 提取与分离 |
| 头花蓼活性组分化学成分研究;张丽娟，等;《中药材》;20120930;第35卷(第9期);1425-1428 |
| 头花蓼黄酮类化学成分的研究;李勇军，等;《中国药学杂志》;20000531;第35卷(第5期);300-302 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106008627A (en) | 2016-10-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106008627B (en) | The preparation and anti-aging purposes of polygonum capitatum flavonoid glycoside compound | |
| CN105503531A (en) | Extract of fungus culture as well as preparation method and application of extract | |
| CN106749731A (en) | A kind of preparation method and application of small molecule notoginseng polysaccharide extract | |
| CN105859816B (en) | Method, application and the product of Sitosterolum and β daucosterols are extracted in fructus cannabis | |
| CN101712649B (en) | Lotus leaf extract, monomer component and application thereof | |
| CN107556362A (en) | The extracting method of cucurbit alkyl-type triterpenoids and anti-alzheimer's disease medical usage | |
| CN103360456B (en) | Triterpene compound and Synthesis and applications | |
| CN111848565B (en) | Monoterpene bishydroxycoumarin compound, pharmaceutical composition, preparation method and application thereof | |
| CN101454001B (en) | Treatment of erectile dysfunction and libido enhancement | |
| CN109400592A (en) | A kind of preparation method of puerarin extract | |
| CN106046081B (en) | The preparation and application of flavonoid glycoside active component in a kind of polygonum capitatum | |
| CN106236792B (en) | The preparation of Folum Ilicis extract and anti-alzheimer's disease purposes | |
| CN103342730B (en) | Preparation method of extract of traditional Chinese medicine herb of manyflower ticklover and use of the extract in anti-aging | |
| CN105198943A (en) | Acylation flavone glycoside named camellikaempferoside A and preparing method and application thereof | |
| CN106674086B (en) | A kind of piperidones Alkaloid compound and its preparation method and application | |
| CN107365284A (en) | A kind of method that taxol is extracted from Chinese yew | |
| CN106967132B (en) | Reactive compound and its preparation method and application in Shenzhou City's honey peach | |
| CN107686501A (en) | Cucurbit alkyl-type triterpenoids extracting method and its anti-aging medical usage | |
| CN111620888B (en) | Method for preparing ailanthinone by utilizing biological fermentation technology | |
| CN103288914A (en) | Preparation method of traditional Chinese medicine manyflower tickclove herb extract and application in anti-senile dementia medicaments | |
| CN104523777B (en) | One kind smoking the extractive of general flavone of falling ox, its extracting method and purposes | |
| CN112876366B (en) | Broom-like isoesterasum, preparation method and application thereof, and pharmaceutical composition | |
| CN102452916A (en) | New aromatic polyketones, extraction method and application thereof | |
| CN109053836B (en) | Luteolin 7-O-succinyl glucoside and apigenin-7-O-succinyl glucoside and application thereof | |
| JPH05163202A (en) | New polyacetylene compounds and 5-lipoxygenase inhibitor containing polyacetylene compound as active ingredient |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |