CN107056857A - A kind of new flavone compound and preparation method and application - Google Patents
A kind of new flavone compound and preparation method and application Download PDFInfo
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- CN107056857A CN107056857A CN201710208961.5A CN201710208961A CN107056857A CN 107056857 A CN107056857 A CN 107056857A CN 201710208961 A CN201710208961 A CN 201710208961A CN 107056857 A CN107056857 A CN 107056857A
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- -1 flavone compound Chemical class 0.000 title claims abstract description 19
- 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 title claims abstract description 11
- 229930003944 flavone Natural products 0.000 title claims abstract description 11
- 235000011949 flavones Nutrition 0.000 title claims abstract description 11
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 210000004509 vascular smooth muscle cell Anatomy 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 8
- 230000010100 anticoagulation Effects 0.000 claims abstract description 7
- 230000004663 cell proliferation Effects 0.000 claims abstract description 7
- 230000036541 health Effects 0.000 claims abstract description 7
- 239000002537 cosmetic Substances 0.000 claims abstract description 4
- 235000013305 food Nutrition 0.000 claims abstract description 4
- 239000001054 red pigment Substances 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 108
- 238000010828 elution Methods 0.000 claims description 48
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 239000000047 product Substances 0.000 claims description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
- 229910002027 silica gel Inorganic materials 0.000 claims description 19
- 239000000741 silica gel Substances 0.000 claims description 19
- 229960001866 silicon dioxide Drugs 0.000 claims description 19
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002994 raw material Substances 0.000 claims description 18
- 239000006227 byproduct Substances 0.000 claims description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims description 8
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 6
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 5
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 230000005779 cell damage Effects 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 11
- 238000011017 operating method Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 description 19
- 239000001257 hydrogen Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 10
- 238000002211 ultraviolet spectrum Methods 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 229940126214 compound 3 Drugs 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 5
- 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 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002215 flavonoids Chemical class 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 238000000990 heteronuclear single quantum coherence spectrum Methods 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005100 correlation spectroscopy Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 210000000663 muscle cell Anatomy 0.000 description 3
- 210000002464 muscle smooth vascular Anatomy 0.000 description 3
- 102000005862 Angiotensin II Human genes 0.000 description 2
- 101800000733 Angiotensin-2 Proteins 0.000 description 2
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 2
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 2
- 229950006323 angiotensin ii Drugs 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 235000005513 chalcones Nutrition 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
- 208000006820 Arthralgia Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001148483 Coniogramme Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 241000718073 Meniscium Species 0.000 description 1
- 208000037093 Menstruation Disturbances Diseases 0.000 description 1
- 206010027339 Menstruation irregular Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- ZONYXWQDUYMKFB-UHFFFAOYSA-N SJ000286395 Natural products O1C2=CC=CC=C2C(=O)CC1C1=CC=CC=C1 ZONYXWQDUYMKFB-UHFFFAOYSA-N 0.000 description 1
- 206010046788 Uterine haemorrhage Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 229930003949 flavanone Natural products 0.000 description 1
- 150000002207 flavanone derivatives Chemical class 0.000 description 1
- 235000011981 flavanones Nutrition 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009993 protective function Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000008736 traumatic injury Effects 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
-
- 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
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- 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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention relates to a kind of new flavone compound, the one or more in structure I~V.The compound can be extracted from Rhizoma Polygoni sinensis using easy, easy-operating method and obtained.The compound that the present invention is provided can effectively anticoagulation, resisting vascular smooth muscle cell proliferation or protection cell, available for preparing medicine and health products；Wherein, compound I and II are natural red pigments, can be added in food, medicine, health products and cosmetics, with potential application value.
Description
Technical field
The present invention relates to field of natural product chemistry, and in particular to a kind of new flavone compound and preparation method thereof with
Using.
Background technology
Rhizoma Polygoni sinensis, pin crescent fern [Abacopteris penangiana (Hook.) are draped over one's shoulders from Thelypteridaceae Meniscium
Ching.] the rhizome of plant, also known as chicken blood lotus, japanese coniogramme rhizome or herb etc.；It is the conventional Chinese medicine among the people of North Western Hunan Tujia；Adjusted with promoting blood circulation
Through, blood stasis removing analgesic, the effects such as dehumidifying；Cure mainly irregular menstruation, uterine bleeding, traumatic injury, arthralgia pain due to rheumatism, the illness such as oedema.
At present, not yet have to extract from Rhizoma Polygoni sinensis and obtain protecting with anticoagulation, resisting vascular smooth muscle cell proliferation or cell
The report of the noval chemical compound of protective function.
The content of the invention
It is an object of the invention to overcome the defect of prior art, a kind of new flavonoid is extracted from Rhizoma Polygoni sinensis
Thing, the compound can effectively anticoagulation, resisting vascular smooth muscle cell proliferation or protection cell, and compound I therein and
II can be used as natural red pigments, with potential application value.
Specifically, one or more of the compound of the present invention in structure I~V：
Invention further provides the preparation method of described compound, comprise the following steps：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is that mobile phase is eluted with acetate-methanol, obtains extract；
(3) extract is separated, purified, produced.
Specifically, the compound I, which can be prepared as follows, forms：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 10~1 with volume ratio：1 acetate-methanol is eluted, and is obtained
Extract；
(3) it is 5~3 by the extract volume ratio：1 methylene chloride-methanol elution, by products therefrom volume ratio
For 1：5~1：1 petroleum ether-methylene chloride-methanol elution, then products therefrom is splined on Sephadex LH-20 post volumes
Than 1:1 chloroform-methanol elution, produces compound I；
Or：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 10~1 with volume ratio：1 acetate-methanol is eluted, and is obtained
Extract；
(3) it is 8~2 by the extract volume ratio：1 methylene chloride-methanol elution, by products therefrom volume ratio
For 5~1：1 chloroform-methanol elution, by products therefrom volume ratio 8~5：1 methylene chloride-methanol elution, then by gained
Product is prepared HPLC by half and eluted using 55% acetonitrile-water as mobile phase, produces compound I.
Specifically, the compound II, which can be prepared as follows, forms：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 10~1 with volume ratio：1 acetate-methanol is eluted, and is obtained
Extract；
(3) it is 5~3 by the extract volume ratio：1 methylene chloride-methanol elution, by products therefrom volume ratio
For 3~0：1 methylene chloride-methanol elution, then products therefrom is splined on Sephadex LH-20 posts volume ratio 1:1 chlorine
Imitation-carbinol is eluted, and produces compound II.
Specifically, the compound III, which can be prepared as follows, forms：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted,
Obtain extract；
(3) it is 8~3 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio be 1~
0：1 chloroform-methanol elution, products therefrom is splined on Sephadex LH-20 posts volume ratio 1:1 chloroform-methanol elution,
Produce compound III.
Specifically, the compound IV, which can be prepared as follows, forms：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted,
Obtain extract；
(3) it is 10~5 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio is 10
~8：1 chloroform-methanol elution, products therefrom volume ratio is 20~10：1 methylene chloride-methanol elution, produces compound
IV；
Or be：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted,
Obtain extract；
(3) it is 3~0 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio be 3~
0：1 chloroform-methanol elution, is 5~3 by products therefrom volume ratio：1 chloroform-methanol elution, then by products therefrom body
Product is than being 5：1 chloroform-methanol elution, produces compound IV.
Specifically, the compound V, which can be prepared as follows, forms：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted,
Obtain extract；
(3) it is 20~10 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio is 20
~10：1 chloroform-methanol elution, products therefrom volume ratio is 20~10：1 chloroform-methanol elution, produces compound V；
Or be：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, takes ethyl acetate layer,
After concentration, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted,
Obtain extract；
(3) it is 3~0 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio be 3~
0：1 chloroform-methanol elution, is 3~1 by products therefrom volume ratio：1 chloroform-methanol elution, then by products therefrom body
Product is than being 5~1：1 chloroform-methanol elution, produces compound V.
Unless particular determination, the stationary phase used during elution of the present invention is silicagel column.
The present invention further protects the compound preparing anticoagulation, resisting vascular smooth muscle cell proliferation and/or cell
Protect the application in medicine and health products；The cytoprotection is preferably to suppress hydrogen peroxide to cause cellular damage.
The present invention protects the compound I and compound II in food, medicine, health products and cosmetics are prepared simultaneously
Using.Specifically, compound I and/or compound II as natural red additive can be added to food, medicine, health care
In product and cosmetics.
The new flavone compound of the present invention is extracted from Rhizoma Polygoni sinensis using easy method and obtained.The compound can
With effective anticoagulation, resisting vascular smooth muscle cell proliferation or protection cell, and compound I and II therein is natural red color
Element, with potential application value.
Brief description of the drawings
Fig. 1~Fig. 8 is respectively the UV spectrums of compound 1, IR is composed, MS is composed,13C-NMR spectrums,1H-NMR spectrums, hsqc spectrum, HMBC spectrums
And1H-1H COSY are composed；
Fig. 9~Figure 16 is respectively the UV spectrums of compound 2, IR is composed, MS is composed,13C-NMR spectrums,1H-NMR spectrums, hsqc spectrum, HMBC
Spectrum and1H-1H COSY are composed；
Figure 17~Figure 24 is respectively the UV spectrums of compound 3, IR is composed, MS is composed,13C-NMR spectrums,1H-NMR spectrums, hsqc spectrum, HMBC
Spectrum and1H-1H COSY are composed；
Figure 25~Figure 32 is respectively the UV spectrums of compound 4, IR is composed, MS is composed,13C-NMR spectrums,1H-NMR spectrums, hsqc spectrum, HMBC
Spectrum and1H-1H COSY are composed；
Figure 33~Figure 40 is respectively the UV spectrums of compound 4, IR is composed, MS is composed,13C-NMR spectrums,1H-NMR spectrums, hsqc spectrum, HMBC
Spectrum and1H-1H COSY are composed；
Figure 41 is the vascular smooth muscle muscle cell multiplication influence schematic diagram that compound 3 is induced Angiotensin II；Its
In, * P<0.05 is compared with normal group,#P<0.05,##P<0.01 is compared with model group；
Figure 42 is protective effect schematic diagram of the compound 3 to the PC12 cells of hydrogen peroxide-induced；*P<0.05,#P<
0.05,##P<0.01 is compared with model group.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
Embodiment 1
A kind of flavone compound is present embodiments provided, concrete structure is as follows：
The sign collection of illustrative plates of the compound is as shown in Fig. 1~Fig. 8；Specifying information is as follows：
Red powder,(c 0.50,MeOH)；
HRESI-MS is provided [M+H]+m/z 459.1661(Calcd for C24H27O9, 459.1655), it may be determined that should
Compound molecule formula is C24H26O9, degree of unsaturation is 12；
UV spectrums, which are shown at 347nm, 524nm, absorption maximum；
IR spectrum displays：Hydroxyl (3413cm-1), carbonyl (1601cm-1) and phenyl ring (1641,1498cm-1)；
13C-NMR spectrums show 24 carbon signals：I.e. one group flavonoid structure, a glucose, a methoxyl group and two first
The signal of base；From1Understood in H-NMR spectrums, six fragrant hydrogen：δH8.64 (1H, dd, 7.6Hz), 7.89 (2H, dd, 8.9Hz),
7.10 (2H, dd, 8.9Hz), 6.81 (1H, dd, 7.6Hz)；One sugared anomeric proton：δH5.42 (d, 7.6Hz), a first
Epoxide：δH3.75 (3H, s), two methyl：δH2.78 (3H, s), 2.38 (3H s), is shown in Table 1；
1H-1In H COSY spectrums, H-3 is related to H-4, H-2'(6') to H-3'(5') it is related, it was confirmed that one-dimensional hydrogen spectrum is even
Close the correlation of signal；
In HMBC spectrums, 4 '-OCH3(δH3.75, s) with C-4 ' (δC162.3) it is related, illustrate that methoxyl group is connected in C-4 ' positions
On；H-2 ' or 6 ' (δH7.89, dd, 8.9Hz) and C-2 (δC158.2), C-3 ' or C-5 ' (δC114.8), C-4 ' (δC
162.3) it is related；H-3 ' or 5 ' (δH7.10, dd, 8.9Hz) and C-1 ' (δC124.1), C-4 ' (δC162.3) it is related；Illustrate B
Ring is the phenyl ring for 4 ' position methoxy substitutions being connected on C-2 positions.H-1″(δH5.42, d, 7.6Hz) and C-5 (δC151.4) phase
Close, illustrate that sugar is connected on C-5 positions；6-CH3(δH2.78, s) with C-5 (δC 151.4)、C-6(δC 128.3)、C-7(δC
183.2) it is related；8-CH3(δH2.38, s) with C-7 (δC 183.2)、C-8(δC 109.2)、C-9(δC153.9) it is, related, say
Bright A rings 6,8 be methyl substitution, 7 are carbonyls.H-3(δH6.82, d, 7.6Hz) and C-2 (δC 158.2)、C-10(δC
118.4)、C-1′(δC124.1) it is related, H-4 (δH8.65, d, 7.6Hz) and C-2 (δC 158.2)、C-5(δC 151.4)、C-
9(δC153.9) it is related, illustrate on C rings 3 and 4 it is unsubstituted.
In summary, identify the compound for 6,8-dimethyl-5-hydroxy-2- (4'-methoxy-phenyl)-
Benzopyran-5-O- β-D-glucopyranoside, i.e. 6,8- dimethyl -5- hydroxyls -2- (4 '-methoxyl group phenyl ring)-benzo
Pyrans -5-O- β-D-Glucose.
Embodiment 2
A kind of flavone compound is present embodiments provided, concrete structure is as follows：
The sign collection of illustrative plates of the compound is as shown in Fig. 9~Figure 16；Specifying information is as follows：
Red powder,(c 1.38, MeOH), HRESIMS is provided [M+H]+m/z 501.1817(Calcd for
C26H29O10, 501.1761), it may be determined that molecular formula is C26H28O10, degree of unsaturation is 13.UV spectrums, which are shown at 512nm, to be had most
It is big to absorb.IR spectrum displays：Hydroxyl (3364cm-1), carbonyl (1729cm-1) and phenyl ring (1647,1601,1499cm-1)。
Comparative compound 1,13In C-NMR spectrums, many δC170.4 (carbonyls) and δC20.4 (methyl).In HMBC spectrums
In, H-6 " (δH4.26, dd) with carbonyl (δC170.4) it is related, illustrate that carbonyl is connected in C-6 " on position；6″-CH3(δH1.89, s)
With carbonyl (δC171.2) it is related, illustrate that methyl is connected on carbonyl position.
In summary, identify the compound for 6,8-dimethyl-5-hydroxy-2- (4'-ethoxy-phenyl)-
Benzopyran-5-O- β-D-6-acety-glucopyranoside, i.e. 6,8- dimethyl -5- hydroxyl -2- (4 '-methoxybenzenes
Ring)-chromene -5-O- β-D-6- acetyl group glucose.
Embodiment 3
A kind of flavone compound is present embodiments provided, concrete structure is as follows：
The sign collection of illustrative plates of the compound is as shown in figure Figure 17~Figure 24；Specifying information is as follows：
White powder,(c 1.75, MeOH), HRESIMS is provided [M+H]+m/z 479.1916(Calcd
for C24H31O10, 479.1917), it may be determined that molecular formula is C24H30O10, degree of unsaturation is 10.UV spectrums are shown at 273nm
There is absorption maximum.IR spectrum displays：Hydroxyl (3400cm-1) and phenyl ring (1604,1569,1460cm-1)。
13The signal of C-NMR spectrum 24 carbon signals of display, i.e., one group flavonoid structure, a glucose and a methoxyl group.
From1Knowable to H-NMR spectrums, aromatic rings hydrogen signal：δH8.06 (d, 8.9Hz, H-2 ' and H-6 '), 6.96 (d, 8.9Hz, H-3 ' and H-
5 ') one group of AX system, is constituted.δH3.34 (dd, H- α), δH3.20 (m, H- α), δH3.06 (2H, dd, H- β), two groups of composition-
CH2- fragment.One sugared end group hydrogen signal：δH4.66 (d, 7.6Hz, H-1 ").One methoxyl group signal：δH 3.85(s,4′-
OCH3).Two methyl signals：δH 2.08(s,5-CH3) and δH 2.18(s,3-CH3).1H-1In H COSY spectrums, H- α and H- β
There are correlation, H-2 ' (δH8.06) with H-3 ' (δH6.96) there is correlation, it was confirmed that one-dimensional hydrogen composes the correlation of coupled signal.
Sugar terminal hydrogen the H-1 " (δ in HMBC spectrumsH4.66) with C-2 (δC151.0) it is related, illustrate that sugar is connected in C-2；δH
2.18 (s, 3-CH3) related to C-3, C-2 etc., illustrate that methyl is connected on 3；δH2.08 (s, 5-CH3) with the phase such as C-5, C-6
Close, illustrate that methyl is connected on 5.H- α (dd, δH3.34；M, δH3.20) it is related to carbonyl carbon, β-C, C-1；H- β (dd, δH
3.06) related to carbonyl carbon, α-C, C-1, C-2, information above illustrates the position of the hydrogen on chalcone parent nucleus.
In summary parse, compound identification is α, β-dihydro-2,4,6-trihydroxy-4 '-methoxy-3,5-
Dimethyl-dihydrochalcone-2-O- β-D-glucopyranoside, i.e., 2,4,6- -4 '-methoxyl group -3 of trihydroxy,
5- dimethyl dihydrochalcones.
Embodiment 4
A kind of flavone compound is present embodiments provided, concrete structure is as follows：
The sign collection of illustrative plates of the compound is as shown in Figure 25~Figure 32；Specifying information is as follows：
Yellow powder,(c 1.63, MeOH), HRESIMS provides [M-Na+H2O]+m/z 485.1043
(Calcd for C22H22O11Na, 485.1060), it may be determined that molecular formula is C22H24O12, degree of unsaturation is 11.UV spectrum displays
There is absorption maximum at 336nm, 414nm.IR spectrum displays：Hydroxyl (3354cm-1) and phenyl ring (1600,1505,1453cm-1)。
13The signal of C-NMR spectrum 22 carbon signals of display, i.e., one group flavonoid structure, a glucose and a methoxyl group
。1The fragrant hydrogen signal δ of H-NMR spectrum displaysH8.38 (d, 2.8Hz, H-6), 7.21 (d, 8.7,2.8Hz, H-4), 7.18 (d,
8.7Hz, H=3), constitute one group of ABX system.Another aromatic rings hydrogen signal δH6.85 (d, 1.7Hz, H-3 '), 6.17 (d,
1.7Hz, H-5 '), constitute one group of AB system.Sugared end group hydrogen signal δH5.85 (d, 7.5Hz, H-1 ").One methoxyl group signal δH
3.74 (s, 4 '-OCH3).1H-1In H COSY spectrums, H-6 has related to H-4, and H-5' has related to H-3', it was confirmed that one-dimensional hydrogen
Compose the correlation of coupled signal.
Sugar terminal hydrogen the H-1 " (δ in HMBC spectrumsH5.85) with C-2 ' (δC157.5) it is related, illustrate that sugar is connected in C-2 ' positions；
H-3′(δH5.85) it is related to C-1 ', C-4 ', C-5 ' etc., H-5 ' (δH5.85) it is related to C-1 ', C-3 ', C-6 ' etc.；H-3(δH
7.18) it is related to C-1, H-4 (δH7.21) it is related to C-5, H-6 (δH8.38) it is related to β-C, C-3, C-4；H-β(δH 8.07)
It is related to carbonyl, α-C, C-2, C-6.Information above illustrates the position of the hydrogen on chalcone parent nucleus.
In summary parse, compound identification is α, 2,5,2 ', 6 '-pentahydroxy-4 '-methoxy-
Chalcone-2 '-O- β-D-glucopyranoside, i.e. α, 2,5,2 ', 6 '-penta hydroxy group -4 '-methoxyl group-chalcone -2 '-O-
β-D-Glucose.
Embodiment 5
A kind of flavone compound is present embodiments provided, is, concrete structure is as follows：
The sign collection of illustrative plates of the compound is as shown in Figure 33~Figure 40；Specifying information is as follows：
Yellow powder,(c 33.63, MeOH), HRESIMS provides the (Calcd of [M+H] m/z 465.1399
for C22H25O11, 465.1397), it may be determined that molecular formula is C22H24O11, degree of unsaturation is 11.UV spectrums are shown at 281nm
There is absorption maximum.IR spectrum displays：Hydroxyl (3333cm-1) and phenyl ring (1649,1607,1505cm-1)。
13C-NMR spectrums show the signal of 22 carbon signals, i.e. flavonoid structure, a glucose and a methoxyl group.1H-
The fragrant hydrogen signal δ of H NMR spectroscopy displayH7.65 (d, 2.4Hz, H-6'), 7.12 (d, 8.7,2.4Hz, H-4'), 7.11 (d, 8.7Hz,
H=3'), one group of ABX system is constituted.Another aromatic rings hydrogen signal δH7.06 (d, 2.4Hz, H-6), 6.39 (d, 2.4Hz, H-
8) one group of AB system, is constituted.Sugared end group hydrogen signal δH5.38 (d, J=7.4Hz, H-1 ").One methoxyl group signal δH 3.68
(s, 7-OCH3).In COSY spectrums, H-6 (δH7.06) with H-8 (δH6.39) there are correlation, H-6'(δH7.65) with H-4'(δH
7.12) there is correlation, it was confirmed that one-dimensional hydrogen composes the correlation of coupled signal.In addition, H-2 (δH6.21) with H-3 (δH3.22) related.
Sugar terminal hydrogen the H-1 " (δ in HMBC spectrumsH5.38) with C-5 (δC161.3) it is related, illustrate that sugar is connected in C-5；H-6
(δH7.06) it is related to C-5, C-7, C-8, C-10 etc., H-8 (δH6.39) it is related to C-6, C-9, C-10 etc.；H-6′(δH
7.65) related to C-2, C-2 ', C-4 ', C-5 ', H-3 ' is " related to C-1 ', C-2 ', C-5；H-2(δH6.21) with C-6 ' phases
Close, H-3 (δH3.22) it is related to C-2, C-4；Information above illustrates the position of the hydrogen on flavanone parent nucleus.
In summary parse, compound identification is 5,2 ', 5 '-trihydroxy-7-methoxy-flavonones-5-O-
β-D-glucopyranoside, i.e., 5,2 ', 5 '-trihydroxy -7- methoxyl groups-flavanone -5-O- β-D-Glucose.
Experimental example 1：External anticoagulation experiment
The present invention is studied the Anticoagulant Activities in vitro of compound 1~5.Result of study is shown：Compound 1~5 is equal
PT the and TT times can be extended, the influence to APTT is not obvious；In the range of sample concentration 0.1g/ml~0.5g/ml, exist certain
Measure dependence；And under sample concentration 0.5g/ml, anticoagulant effect is most notable.
Experimental example 2：The vascular smooth muscle muscle cell multiplication shadow that MTT test method(s)s detection compound is induced Angiotensin II
Ring
Cell line：Vascular smooth muscle cells (VSMCs)
Experimental result：MTT experiment has been carried out to compound 3, has as a result shown that compound 3 is dense in 10 μm of ol/l and 30 μm of ol/l
When spending, the activity with good suppression vascular smooth muscle muscle cell multiplication, as a result as shown in figure 41.
Experimental example 3：Protective effect of the MTT test method(s)s detection compound to the PC12 cells of hydrogen peroxide-induced
Cell line：PC12 cells
Experimental result：MTT experiment has been carried out to compound 3, has as a result shown that compound 3 is thin to the PC12 of hydrogen peroxide-induced
Born of the same parents have preferable protective effect, as a result as shown in figure 42.
From result above, there is resisting vascular smooth muscle cell proliferation activity to compound 3 and hydrogen peroxide is caused to damage
The PC12 cells of wound have protective effect.
The present invention is detected that above-claimed cpd is respectively provided with and the class of compound 3 to the activity of compound 1,2,4,5 simultaneously
As activity.
Although above having made to retouch in detail to the present invention with general explanation, embodiment and experiment
State, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, are belonged to claimed
Scope.
Claims (9)
1. a kind of new flavone compound, it is characterised in that the one or more in structure I~V, wherein, compound
I, compound II are natural red pigments：
2. the preparation method of compound described in claim 1, it is characterised in that comprise the following steps：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is that mobile phase is washed with petroleum ether-ethyl acetate or acetate-methanol
It is de-, obtain extract；
(3) extract is separated, purified, produced.
3. method according to claim 2, it is characterised in that methods described is specially：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 10~1 with volume ratio：1 acetate-methanol is eluted, and must be extracted
Thing；
(3) it is 5~3 by the extract volume ratio：1 methylene chloride-methanol elution, is 1 by products therefrom volume ratio：
5~1：1 petroleum ether-methylene chloride-methanol elution, then products therefrom is splined on Sephadex LH-20 posts volume ratio 1:
1 chloroform-methanol elution, produces compound I；
Or be：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 10~1 with volume ratio：1 acetate-methanol is eluted, and must be extracted
Thing；
(3) it is 8~2 by the extract volume ratio：1 methylene chloride-methanol elution, is 5 by products therefrom volume ratio
~1：1 chloroform-methanol elution, by products therefrom volume ratio 8~5：1 methylene chloride-methanol elution, then by products therefrom
HPLC is prepared by half to be eluted as mobile phase using 55% acetonitrile-water, produces compound I.
4. method according to claim 2, it is characterised in that methods described is specially：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 10~1 with volume ratio：1 acetate-methanol is eluted, and must be extracted
Thing；
(3) it is 5~3 by the extract volume ratio：1 methylene chloride-methanol elution, is 3 by products therefrom volume ratio
~0：1 methylene chloride-methanol elution, then products therefrom is splined on Sephadex LH-20 posts volume ratio 1:1 chloroform-
Methanol is eluted, and produces compound II.
5. method according to claim 2, it is characterised in that methods described is specially：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted, and must be carried
Take thing；
(3) it is 8~3 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio is 1~0：1
Chloroform-methanol is eluted, and products therefrom is splined on Sephadex LH-20 posts volume ratio 1:1 chloroform-methanol elution, producing
Compound III.
6. method according to claim 2, it is characterised in that methods described is specially：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted, and must be carried
Take thing；
(3) it is 10~5 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio is 10~8：1
Chloroform-methanol elution, products therefrom volume ratio be 20~10：1 methylene chloride-methanol elution, produces compound IV；
Or be：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted, and must be carried
Take thing；
(3) it is 3~0 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio is 3~0：1
Chloroform-methanol is eluted, and is 5~3 by products therefrom volume ratio：1 chloroform-methanol elution, then by products therefrom volume ratio
For 5：1 chloroform-methanol elution, produces compound IV.
7. method according to claim 2, it is characterised in that methods described is specially：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted, and must be carried
Take thing；
(3) it is 20~10 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio be 20~
10：1 chloroform-methanol elution, products therefrom volume ratio is 20~10：1 chloroform-methanol elution, produces compound V；
Or be：
(1) Rhizoma Polygoni sinensis raw material is taken, is extracted with ethanol, gained extract solution is extracted with ethyl acetate, ethyl acetate layer is taken, concentrated
Afterwards, medicinal extract is obtained；
(2) medicinal extract is splined on silicagel column, is 100~20 with volume ratio：1 acetate-methanol is eluted, and must be carried
Take thing；
(3) it is 3~0 by the extract volume ratio：1 chloroform-methanol elution, products therefrom volume ratio is 3~0：1
Chloroform-methanol is eluted, and is 3~1 by products therefrom volume ratio：1 chloroform-methanol elution, then by products therefrom volume ratio
For 5~1：1 chloroform-methanol elution, produces compound V.
8. compound described in claim 1 prepare anticoagulation, resisting vascular smooth muscle cell proliferation and/or cell-protecting medicines and
Application in health products；Preferably, the cytoprotection causes cellular damage to suppress hydrogen peroxide.
9. the application of compound I and compound II in food, medicine, health products and cosmetics are prepared described in claim 1, its
It is characterised by, compound I and/or compound II is added as natural red additive.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102058627A (en) * | 2010-12-20 | 2011-05-18 | 华中科技大学 | Abacopteris penangiama total flavonoid and preparation, assay method and application thereof |
| CN103006633A (en) * | 2012-11-27 | 2013-04-03 | 广东省中医院 | Application of hydroxysafflor yellow A in preparation of medicament for resisting Alzheimer disease |
| CN103494800A (en) * | 2013-10-18 | 2014-01-08 | 武汉大学 | Application of procyanidine B2 in preparation of drugs for preventing oxidative damage and inhibiting cell apoptosis |
| CN104173390A (en) * | 2013-05-22 | 2014-12-03 | 香港浸会大学 | Use of a flavanol glycoside for suppressing activation of stellate cells |
-
2017
- 2017-03-31 CN CN201710208961.5A patent/CN107056857B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102058627A (en) * | 2010-12-20 | 2011-05-18 | 华中科技大学 | Abacopteris penangiama total flavonoid and preparation, assay method and application thereof |
| CN103006633A (en) * | 2012-11-27 | 2013-04-03 | 广东省中医院 | Application of hydroxysafflor yellow A in preparation of medicament for resisting Alzheimer disease |
| CN104173390A (en) * | 2013-05-22 | 2014-12-03 | 香港浸会大学 | Use of a flavanol glycoside for suppressing activation of stellate cells |
| CN103494800A (en) * | 2013-10-18 | 2014-01-08 | 武汉大学 | Application of procyanidine B2 in preparation of drugs for preventing oxidative damage and inhibiting cell apoptosis |
Non-Patent Citations (7)
| Title |
|---|
| （加）JIM SMITH 等主编: "《食品添加剂实用手册》", 30 November 2004, 中国农业出版社 * |
| HAN WEI等: "Total flavan glycoside from Abacopteris penangiana rhizomes and its acid hydrolysate: Characterisation and anti-benign prostatic hyperplasia potential", 《FOOD CHEMISTRY》 * |
| M. BIJAK ET AL.: "Thrombin inhibitory activity of some polyphenolic compounds", 《MED CHEM RES》 * |
| PHI-HUNG NGUYEN ET AL.: "Antithrombotic and antidiabetic flavonoid glycosides from the grains of Sorghum bicolor (L.) Moench var. hwanggeumchal", 《ARCH. PHARM. RES.》 * |
| ZHEN FANA ET AL.: "New Flavanol Glucosides from Abacopteris aspera (Presl) Ching", 《HELVETICA CHIMICA ACTA》 * |
| ZHONGXIANG ZHAO ET AL.: "Flavan-4-ol Glycosides from the Rhizomes of Abacopteris penangiana", 《J. NAT. PROD.》 * |
| ZHONGXIANG ZHAO ET AL.: "Two New Flavonoids from the Rhizomes of Abacopteris penangiana", 《HELVETICA CHIMICA ACTA》 * |
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