CN106008627A - Preparation and anti-aging application of polygonum capitatum flavonoid glycoside compounds - Google Patents
Preparation and anti-aging application of polygonum capitatum flavonoid glycoside compounds Download PDFInfo
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- CN106008627A CN106008627A CN201610410464.9A CN201610410464A CN106008627A CN 106008627 A CN106008627 A CN 106008627A CN 201610410464 A CN201610410464 A CN 201610410464A CN 106008627 A CN106008627 A CN 106008627A
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- flavonoid glycoside
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- ethyl acetate
- polygonum capitatum
- methanol
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- 229930182486 flavonoid glycoside Natural products 0.000 title claims abstract description 25
- -1 flavonoid glycoside compounds Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- 230000003712 anti-aging effect Effects 0.000 title claims abstract description 13
- 241000764065 Persicaria capitata Species 0.000 title abstract description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000002904 solvent Substances 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000000746 purification Methods 0.000 claims abstract description 8
- 238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 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 28
- 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 21
- 150000001875 compounds Chemical class 0.000 claims description 15
- 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 14
- 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 14
- 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 claims description 14
- 235000005875 quercetin Nutrition 0.000 claims description 14
- 229960001285 quercetin Drugs 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- 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 claims description 7
- 235000008777 kaempferol Nutrition 0.000 claims description 7
- 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 claims description 7
- 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 claims description 7
- 235000007743 myricetin Nutrition 0.000 claims description 7
- 229940116852 myricetin Drugs 0.000 claims description 7
- 150000008265 rhamnosides Chemical class 0.000 claims description 7
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- 239000007787 solid Substances 0.000 claims description 6
- 150000007955 flavonoid glycosides Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
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- 239000002552 dosage form Substances 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims 1
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- 240000004808 Saccharomyces cerevisiae Species 0.000 abstract description 12
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 abstract description 12
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- 229940079593 drug Drugs 0.000 abstract 1
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- 230000003362 replicative effect Effects 0.000 abstract 1
- 238000000967 suction filtration Methods 0.000 abstract 1
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- 230000032683 aging Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
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- 239000000843 powder Substances 0.000 description 4
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- 238000011160 research Methods 0.000 description 3
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- 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
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- 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
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000219050 Polygonaceae Species 0.000 description 1
- 244000173166 Pyrus ussuriensis Species 0.000 description 1
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- 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
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
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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
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- 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 invention provides a preparation method of polygonum capitatum flavonoid glycoside compounds. The preparation method includes the steps that polygonum capitatum is smashed, methanol extraction is carried out, suction filtration concentration is carried out, ethyl acetate concentration is carried out after water and ethyl acetate solvent distribution, separation is carried out with a silica column, then purification is carried out with an ODS-bonded silica filler open column and HPLC, and the polygonum capitatum flavonoid glycoside compounds are obtained. It is shown through a brewer's yeast K6001 bioactivity system that all the four flavonoid glycoside compounds can significantly prolong the replicative life of yeast. The polygonum capitatum flavonoid glycoside compounds can be applied to preparation of anti-aging drugs or health-care products. The preparation method is simple, and the extracted product is high in purity; polygonum capitatum is a cheap traditional Chinese medicinal material easy to obtain, the pharmaceutical application of polygonum capitatum is increased, and the anti-aging potential of the components of polygonum capitatum is found.
Description
Technical field
The invention belongs to pharmaceutical technology field, be specifically related to the preparation method of Herba Polygoni Capitati flavonoid glycoside reactive compound and in preparation
Application in antiaging agent.
Background technology
Reach 9.01 hundred million according to recent statistics data, 60 years old, the whole world and the above aged in 2015, accounted for the world
The 12% of total population.The world has been enter into aging society, and the disease that the thing followed is relevant to aging becomes the problem day by day highlighted.
Neurodegenerative diseases including Alzheimer is one of global public health difficult problem.Only in China, the elderly
Mouthful already more than 200,000,000, the patient populations of Alzheimer in 2014 more than 6,000,000.At medicine, find anti-
The medicine controlling Senile disease has become as the task of top priority.
Through Aging mechanism is studied for a long period of time, in this area, form multiple causes of senescence, said including programmed aging, somatic cell
Mutation theory, mistake are caused disaster, and free radical is said, neuroendocrine is said, immunosenescence is said, etc..Aging be one sufficiently complex
Process, same class antiaging agent play drug effect mode be also not quite similar.
Polygonaceae plant Herba Polygoni Capitati (Polygonum capitatum) is perennial draft of crawling, and is a kind of medicinal herbs most in use in Miao Ethnomedicine,
There is the highest medical value.As the conventional medical herbs that Guizhou is national, the medical value of Herba Polygoni Capitati has been studied: Herba Polygoni Capitati carries
Take thing and the application in hypoglycemic drug thereof;Herba Polygoni Capitati extract application in whitening articles for use and whitening articles for use;There is antiinflammatory
The Relinqing Granula raw material Herba Polygoni Capitati extract of effect;There is the Relinqing Granula raw material Herba Polygoni Capitati extract of anti-gonococcus effect;
For preventing or treat the polygonum capitatum composition of comedo;For treating or prevent the polygonum capitatum composition of oral disease.
Summary of the invention
It is an object of the invention to provide the preparation method of a kind of Herba Polygoni Capitati flavonoid glycoside reactive compound, obtained by following steps preparation
:
(1) extracting with methanol after Herba Polygoni Capitati is pulverized, sucking filtration concentrates with ethyl acetate and aqueous solvent distribution, ethyl acetate layer after concentrating again,
Obtain ethyl acetate layer study;
(2) by gained ethyl acetate layer study successively through silica gel opening column separate separate with twice ODS opening column, obtain two anti-ageing
Old active component;
(3) two anti-aging active ingredients of gained obtain four flavonoid glycoside reactive compounds after purification through HPLC, are respectively
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 that in step (2), silica gel opening column separates is normal hexane: dichloro=100: 0,90: 10,70: 30,50:
50,30: 70,10: 90,0: 100;Dichloromethane subsequently: ethyl acetate=90: 10,70: 30,50: 50,30:
70,0: 100;It it is finally methanol-eluted fractions.The solvent system that ODS opening column separates for the first time is methanol: water=30: 70,35:
65,40: 60,50: 50,60: 40,70: 30,90: 10,100: 0.The solvent system that ODS opening column separates for the second time
System is respectively as methanol: water=30: 70,50: 50 and 30: 70, and 35: 65,60: 40.
In step (3), the chromatographic condition of HPLC purification is respectively as follows: chromatographic column CAPCELL PAKC18 (10/250mm), stream
Speed 3mL/min, detects wavelength 210nm, mobile phase methanol: water=38: 62 and chromatographic column Develosil C30-UG-5
(10/250mm), Nomura Chemical, flow velocity 3mL/min, detect wavelength 210nm, mobile phase methanol: water=48:
52。
It is a further object to provide the application in preparing antiaging agent or health product of the described flavonoid glycoside compound.
The present invention studies discovery, and the flavonoid glycoside compound that the Herba Polygoni Capitati obtained by the inventive method is originated, can in defying age model
Yeast replicability life-span (see Fig. 1), especially four flavonoid glycoside compounds are extended with notable.Illustrate that it has activity of fighting against senium.
The flavonoid glycoside compound in the Herba Polygoni Capitati source that the present invention provides can prepare pharmaceutically acceptable load according to any conventional process
Body or diluent.Pharmaceutically acceptable carrier described here refers to the pharmaceutical carrier that pharmaceutical field is conventional, such as diluent,
Excipient in this way etc., filler such as starch, sucrose, microcrystalline Cellulose etc.;Binding agent such as starch slurry, hydroxypropylcellulose, gelatin,
Polyethylene Glycol etc.;Wetting agent such as magnesium stearate, micropowder silica gel, polyethylene glycols etc.;Absorption enhancer poly-Pyrusussuriensis fat, lecithin
Deng, surfactant poloxamer, fatty acid Pyrusussuriensis Pyrusussuriensis fat smooth, poly-etc., it can in addition contain add other in compound
Adjuvant such as flavouring agent, sweeting agent etc..
The dosage form being administered can be tablet, pill, powder, dispersible tablet, sachets, elixir, suspensoid, Emulsion, solution
Agent, syrup, aerosol, soft capsule, hard capsule, aseptic parenteral solution, liniment or suppository.Can be made into routine, rapid release, delay
Release or postpone release.
The flavonoid glycoside compound of the present invention can give by all means, including being administered orally, and nasal cavity, muscle, subcutaneous, intravenous etc..
The flavonoid glycoside compound in the Herba Polygoni Capitati source that the present invention provides shows the most anti-ageing in saccharomyces cerevisiae K6001 system
Old activity.Preparation method of the present invention is simple, and the product purity of extraction is high, and Herba Polygoni Capitati is the cheap Chinese medicine that is easy to get, for defying age
The research and development of medicine or health product carry out basic research, will have important practical significance.
Accompanying drawing explanation
Fig. 1 be four flavonoid glycoside compounds in K6001 bioactive systems to yeast replicability life-time dilatation effect;Figure
Middle 1:myricetin 7-O--L-rhamnopyranoside, 2:quercetin 4'-O-α-L-rhamnopyranoside,
3:quercetin 3-O-α-(2 "-galloyl) rhamnoside, 4:kaempferol
3-O- -L-rhamnopyranoside。
Detailed description of the invention
Below by way of prepared by such some particular compound the embodiment of example and the accompanying drawing foregoing again to the present invention make into
The detailed description of one step, but this should not being interpreted as, the scope of the above-mentioned theme of the present invention is only limitted to following example, all based on this
The technology that bright foregoing is realized belongs to the scope of the present invention.
Embodiment 1
The preparation method of four flavonoid glycoside compounds of separation and Extraction from Herba Polygoni Capitati, concretely comprises the following steps:
1) pulverize and extract:
After Herba Polygoni Capitati that 250g is dried is pulverized, with extracting 2 times under 2.5L methanol (technical grade) room temperature, each 1 day, sucking filtration
Concentrate, obtain methanol extract study, by ethyl acetate and water extract and separate, stand, after ethyl acetate layer concentrating under reduced pressure is spin-dried for,
Obtain ethyl acetate layer study 9g.
2) separation and purification:
By ethyl acetate layer study first through silica gel opening column separate (200-300 mesh, following solvent system by volume, normal hexane:
Dichloromethane solvent system is by volume: 100: 0,90: 10,70: 30,50: 50,30: 70,10: 90,0:
100;Dichloromethane subsequently: ethyl acetate solvent system is by volume: 90: 10,70: 30,50: 50,30: 70,0:
100;It is finally methanol);Active sample use ODS opening column again is separated (solvent system is methanol by volume: water=0: 70,
35: 65,40: 60,50: 50,60: 40,70: 30,90: 10,100: 0);Obtain two active component A 1 (975.7
And B1 (267.4mg), mg) then A1 with B1 separates that (solvent system is respectively first by volume respectively by ODS opening column
Alcohol: water is: 30: 70,50: 50 and 30: 70,35: 65,60: 40), obtain higher two active component A 2 (129.4 of purity
And B2 (139.9mg) mg).Take A2 50mg HPLC purification, chromatographic condition: chromatographic column PAKC18(10/250mm), stream
Speed 3ml/min, detects wavelength 210nm, and flowing is mutually for methanol: water=38: 62, obtains compound myricetin
7-O--L-rhamnopyranoside (2.7mg, retention time is 19.5min), quercetin
4'-O-α-L-rhamnopyranoside (35.8mg, retention time is 38.0min);Take B2 20mg HPLC purification,
Chromatographic condition: chromatographic column C30-UG-5 (10/250mm), flow velocity 3ml/min, detect wavelength 210nm, flowing is mutually for methanol:
Water=48: 52, obtain compound quercetin 3-O-α-(2 "-galloyl) rhamnoside (5.3mg, retention time
For 54.8min), kaempferol 3-O--L-rhamnopyranoside (2.5mg, retention time is 60.6min).
Four flavonoid glycoside compound structural formulas are as follows:
Embodiment 2
To embodiment 1 gained compound myricetin 7-O--L-rhamnopyranoside, quercetin
4'-O-α-L-rhamnopyranoside, quercetin 3-O-α-(2 "-galloyl) rhamnoside, and
The physicochemical characteristics of kaempferol 3-O--L-rhamnopyranoside and the Qualitative Identification of chemical constitution:
Compound myricetin 7-O--L-rhamnopyranoside, quercetin
4'-O-α-L-rhamnopyranoside, quercetin 3-O-α-(2 "-galloyl) rhamnoside, and
The structure of kaempferol 3-O--L-rhamnopyranoside determines through 1H NMR, MS and document comparison.
The physicochemical property of compound myricetin 7-O--L-rhamnopyranoside: yellow-brown solid, molecular formula is 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 is
C21H20O11;ESI-TOF-MS:m/z 449.1114 (M+H)+, hydrogen modal data:1HNMR(500MHz,
CD3:=7.33 (d, 1H, J=1.5Hz), OD) 7.30 (dd, 1H, J=8.0,1.5Hz), 6.90 (d, 1H, J=8.0
Hz), 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).
The physicochemical property of compound quercetin 3-O-α-(2 "-galloyl) rhamnoside: yellow solid, molecular 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=3.5,2.0
Hz), 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 is
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, in defying age model discrimination, show activity of fighting against senium, can significantly extend K6001 yeast
The replicability life-span.
The living model being currently used for research on anti-senescence mainly has mouse, nematicide, fruit bat and yeast.The present embodiment selects wine brewing ferment
Female active system as research on anti-senescence, because yeast is single celled eukaryote, life cycle is short, has obtained it complete
Genomic data, is that the most conventional aging model is biological.Simultaneously using resveratrol as positive control, resveratrol is current
Well-known, in several animal models, show the micromolecular compound of anti-aging effects.
Analysis method comprises the following steps:
(1) take out K6001 yeast strain from-30 DEG C of refrigerators, wash three times with PBS, each 5ml, remove glycerol therein.?
Rear addition 1ml PBS, piping and druming so that it is join after suspension 5ml fluid medium (yeast powder of 1%, the peptone of 2%, 3%
Galactose) in.28 DEG C of shakings (160r/min) cultivate 24 hours;
(2) wash three times with 5ml PBS after cultivation terminates, remove fluid medium therein, count with blood counting chamber, calculate ferment
Female concentration;
(3) dehydrated alcohol is used to make solvent, preparation 1 μM respectively, 3 μMs, standby;
(4) add in sterilized culture dish 5ml solid medium (yeast powder of 1%, the peptone of 2%, the glucose of 2%,
The agar powder of 2%), after culture medium solidifying, it is separately added in step (3) sample prepared wherein, adds after solvent volatilization
Enter 4000 yeast, smear uniformly with spreader, 28 DEG C of constant temperature culture 48 hours;
(5) under microscope, every ware counts the daughter cell number that 40 blast cells produce respectively at random, and record, mapping analysis, result
See Fig. 1.
Claims (6)
1. the preparation method of a Herba Polygoni Capitati flavonoid glycoside compound, it is characterised in that realized by following steps:
(1) extracting with methanol after Herba Polygoni Capitati is pulverized, sucking filtration concentrates with ethyl acetate and aqueous solvent distribution, ethyl acetate layer after concentrating again,
Obtain ethyl acetate layer study;
(2) by gained ethyl acetate layer study successively through silica gel opening column separate separate with twice ODS opening column, obtain two anti-ageing
Old active component;
(3) two anti-aging active ingredients of gained obtain four flavonoid glycoside reactive compounds after purification through HPLC, are respectively
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 preparation method of a kind of Herba Polygoni Capitati flavonoid glycoside compound the most according to claim 1, it is characterised in that step (2)
The solvent system that middle silica gel opening column separates is normal hexane: dichloro=100: 0,90: 10,70: 30,50: 50,30:
70,10: 90,0: 100;Dichloromethane subsequently: ethyl acetate=90: 10,70: 30,50: 50,30: 70,0:
100;It it is finally methanol-eluted fractions;The solvent system that ODS opening column separates for the first time is methanol: water=30: 70,35: 65,
40: 60,50: 50,60: 40,70: 30,90: 10,100: 0;The solvent system that ODS opening column separates for the second time divides
Wei be for methanol: water=30: 70,50: 50 and 30: 70,35: 65,60: 40.
The preparation method of a kind of Herba Polygoni Capitati flavonoid glycoside compound the most according to claim 1, it is characterised in that step (3)
The chromatographic condition of middle HPLC purification 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, detect wavelength 210nm, mobile phase methanol: water=48: 52.
The Herba Polygoni Capitati flavonoid glycoside compound that the most according to claim 1, prepared by method is in preparing antiaging agent or health product
Application.
Application the most according to claim 4, it is characterised in that described medicine by flavonoid glycoside compound with pharmaceutically can connect
The carrier being subject to or diluent prepare.
Application the most according to claim 4, it is characterised in that described pharmaceutical dosage form selects solid preparation or liquid preparation.
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CN114689729A (en) * | 2020-12-31 | 2022-07-01 | 鲁南制药集团股份有限公司 | Method for detecting flavonoid glycoside component in Jingfang granules |
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Cited By (3)
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CN114689729A (en) * | 2020-12-31 | 2022-07-01 | 鲁南制药集团股份有限公司 | Method for detecting flavonoid glycoside component in Jingfang granules |
CN114249782A (en) * | 2022-01-05 | 2022-03-29 | 湖南大学 | Prodrug for selectively destroying lysosome of aged cells and preparation method and application thereof |
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 |
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