CN114452293B - Application of vitexin xyloside in reducing uric acid and preparation method thereof - Google Patents
Application of vitexin xyloside in reducing uric acid and preparation method thereof Download PDFInfo
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- CN114452293B CN114452293B CN202210171124.0A CN202210171124A CN114452293B CN 114452293 B CN114452293 B CN 114452293B CN 202210171124 A CN202210171124 A CN 202210171124A CN 114452293 B CN114452293 B CN 114452293B
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- uric acid
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- vitexin
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- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 title claims abstract description 49
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 229940116269 uric acid Drugs 0.000 title claims abstract description 46
- JMFSHKGXVSAJFY-UHFFFAOYSA-N Saponaretin Natural products OCC(O)C1OC(Oc2c(O)cc(O)c3C(=O)C=C(Oc23)c4ccc(O)cc4)C(O)C1O JMFSHKGXVSAJFY-UHFFFAOYSA-N 0.000 title claims abstract description 42
- MOZJVOCOKZLBQB-UHFFFAOYSA-N Vitexin Natural products OCC1OC(Oc2c(O)c(O)cc3C(=O)C=C(Oc23)c4ccc(O)cc4)C(O)C(O)C1O MOZJVOCOKZLBQB-UHFFFAOYSA-N 0.000 title claims abstract description 42
- PZKISQRTNNHUGF-UHFFFAOYSA-N vitexine Natural products OC1C(O)C(O)C(CO)OC1OC1=C(O)C=C(O)C2=C1OC(C=1C=CC(O)=CC=1)=CC2=O PZKISQRTNNHUGF-UHFFFAOYSA-N 0.000 title claims abstract description 42
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 title claims abstract description 41
- SGEWCQFRYRRZDC-VPRICQMDSA-N vitexin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1C1=C(O)C=C(O)C2=C1OC(C=1C=CC(O)=CC=1)=CC2=O SGEWCQFRYRRZDC-VPRICQMDSA-N 0.000 title claims abstract description 38
- 230000001603 reducing effect Effects 0.000 title claims abstract description 17
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 8
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 3
- 238000002386 leaching Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 208000030159 metabolic disease Diseases 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract 1
- 238000010828 elution Methods 0.000 description 11
- 230000002496 gastric effect Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 6
- 239000013641 positive control Substances 0.000 description 6
- -1 vitexin xyloside derivative Chemical class 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 201000001431 Hyperuricemia Diseases 0.000 description 3
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 3
- 238000012449 Kunming mouse Methods 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- QARYADFHOUHDSW-UHFFFAOYSA-M potassium 2H-oxazine-3-carboxylate Chemical compound O1NC(=CC=C1)C(=O)[O-].[K+] QARYADFHOUHDSW-UHFFFAOYSA-M 0.000 description 3
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 210000000683 abdominal cavity Anatomy 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 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 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 241000219317 Amaranthaceae Species 0.000 description 1
- 244000025352 Artocarpus heterophyllus Species 0.000 description 1
- 235000008725 Artocarpus heterophyllus Nutrition 0.000 description 1
- 244000140786 Brassica hirta Species 0.000 description 1
- 235000011371 Brassica hirta Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 244000018436 Coriandrum sativum Species 0.000 description 1
- 235000002787 Coriandrum sativum Nutrition 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241000195950 Equisetum arvense Species 0.000 description 1
- 239000005768 Equisetum arvense L. Substances 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 125000000899 L-alpha-glutamyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 206010046337 Urate nephropathy Diseases 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- BQSJTQLCZDPROO-UHFFFAOYSA-N febuxostat Chemical compound C1=C(C#N)C(OCC(C)C)=CC=C1C1=NC(C)=C(C(O)=O)S1 BQSJTQLCZDPROO-UHFFFAOYSA-N 0.000 description 1
- 229960005101 febuxostat Drugs 0.000 description 1
- 210000002196 fr. b Anatomy 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- COSZWAUYIUYQBS-UHFFFAOYSA-B hexapotassium hexasodium 3-carboxy-3-hydroxypentanedioate 2-hydroxypropane-1,2,3-tricarboxylate hydrate Chemical compound O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[K+].[K+].[K+].[K+].[K+].[K+].OC(=O)CC(O)(C(O)=O)CC(O)=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O COSZWAUYIUYQBS-UHFFFAOYSA-B 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229940098458 powder spray Drugs 0.000 description 1
- DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
- 229960003081 probenecid Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- 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
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses application of vitexin xyloside in reducing uric acid and a preparation method thereof, and belongs to the technical field of pharmaceutical chemistry. In the invention, the vitexin xyloside is obtained by purifying and extracting from the sticky note, has the effect of reducing uric acid, can be applied to preparing medicines for treating metabolic diseases caused by high uric acid, and has good medical value and wide application prospect. In addition, the preparation method of the vitexin xyloside is simple, efficient and easy to operate, and can make up the defect that the vitexin xyloside cannot be industrially produced in the prior art.
Description
Technical Field
The invention belongs to the technical field of pharmaceutical chemistry, and in particular relates to uric acid reducing application of vitexin xyloside and a preparation method thereof.
Background
The distribution of vitexin xyloside (vitexin-2 "-O-xyloside) in plants is not extensive and has only been demonstrated in a few plants such as jackfruit (CN 104974202A), equisetum arvense (Z.Naturasch.36 c,1981: 484-485). At present, vitexin xyloside is difficult to obtain from commercial sources, so research on vitexin xyloside is limited, and corresponding references are fewer.
The structural formula of vitexin xyloside is shown as follows:
The pharmacological activity of vitexin xyloside is only slightly reported in a few documents, for example, in patent CN104958311a, vitexin xyloside has been demonstrated to have hypoglycemic and hypolipidemic effects.
Disclosure of Invention
The invention discovers that vitexin xyloside has the effect of regulating the content of blood uric acid for the first time on the basis of the prior art, and particularly, the vitexin xyloside has the effect of reducing uric acid.
Based on the scientific research results, the invention provides an application of vitexin xyloside, which is used for preparing a medicament for treating metabolic diseases caused by high uric acid. The medicine comprises, but is not limited to, vitexin xyloside as an effective component, or vitexin xyloside derivative as an effective component.
In the invention, the vitexin xyloside derivative refers to a compound which exists naturally or is reasonably transformed from vitexin xyloside artificially and has the same or similar core skeleton with vitexin xyloside, and the uric acid reducing effect is the same or similar to that of vitexin xyloside and even higher than that of vitexin xyloside.
In the present invention, metabolic diseases caused by high uric acid include, but are not limited to, one or more of hyperuricemia, gout, tophus, uric acid stones, uric acid nephropathy.
The invention provides a medicine with uric acid reducing effect, which comprises vitexin xyloside or vitexin xyloside derivatives.
In the invention, the medicament with uric acid reducing effect can also comprise one or more of pharmaceutically acceptable carriers, auxiliary materials and excipients.
In the present invention, the above-mentioned drug having uric acid lowering effect may be in the form of capsule, granule, tablet, pill, spray, suppository, aerosol, powder spray, patch, oral liquid or injection.
The invention also provides a pharmaceutical composition with uric acid reducing effect, which consists of vitexin xyloside or vitexin xyloside derivatives and other uric acid reducing chemical components.
In the present invention, other uric acid lowering chemical ingredients include, but are not limited to, any one or more of the following: allopurines, benzobromocoumarin, febuxostat, probenecid, sodium bicarbonate, and sodium potassium hydrogen citrate.
In the invention, vitexin xyloside is obtained by purifying and extracting from the sticky note. Therefore, the invention also provides a method for preparing vitexin xyloside from the sticky note, which comprises the following steps:
extracting radix Cynanchi Paniculati with 95% ethanol, and concentrating to obtain extract A. Performing MCI column chromatography on the extract A, eluting with water as eluent, and concentrating the eluent to obtain extract B. Decolorizing the extract B by gel column chromatography, removing impurities, and purifying by preparative high pressure liquid chromatography to obtain vitexin xyloside.
In the preparation method of vitexin xyloside, the gel column is selected from Sephadex LH-20 gel column, and the eluent is methanol.
In the preparation method of the vitexin xyloside, the mobile phase of the high-pressure liquid chromatography is acetonitrile, water=5% > 95% -50% > 50%.
The beneficial effects of the invention are as follows:
The invention proves that the vitexin xyloside has the effect of reducing uric acid for the first time. On the basis, the vitexin xyloside can be applied to research and development and preparation of medicines for treating metabolic diseases caused by high uric acid, and has high medical value and broad prospect. In addition, the vitexin xyloside is extracted from the sticky note, and on the basis, the invention also provides a method for efficiently extracting the vitexin xyloside from the sticky note, which is simple, efficient and easy to operate, and can enable the vitexin xyloside to be rapidly and massively prepared more easily than the prior art.
Detailed Description
In the invention, allopurines, potassium oxazinate, hypoxanthine and Tween-80 are purchased from Michelin corporation, male Kunming mice are purchased from Shanghai Baitong Biotechnology Co., ltd, and uric acid test paper and detectors are purchased from Baijie corporation. Other test materials or reagents for the present invention are commercially available unless otherwise indicated.
The terms used in the present invention, as not specifically described, generally have meanings commonly understood by those of ordinary skill in the art. The invention will be described in further detail below in connection with specific embodiments and with reference to the data. The following examples are intended to illustrate the invention and are not intended to limit the scope of the invention in any way.
The Coriandrum sativum is a plant of the genus Beta of the family Chenopodiaceae, is rich in microelements such as reducing bran, collagen, cellulose, vitamin C, potassium, calcium, ferrum, etc., and has effects of removing blood stasis, stopping bleeding, and reducing blood serum lipid. In recent years, in the study of the biological activity of the sticky note, we also found that the sticky note has uric acid lowering effect (CN 107581306A). On the basis, substances with uric acid reducing activity in the sticky note are screened, and the specific steps are as follows:
Concentrated positioning of uric acid-lowering active ingredients
(1) MCI column chromatography segmentation
18Kg of naturally air-dried sticky note is chopped and soaked with 60L of 95% ethanol for 3 times, 7 days each. Concentrating the 3 times extractive solution, and recovering ethanol to obtain 3.2kg extract. Suspending the extract with 2L purified water, performing ultrasonic treatment for 30min, and performing MCI column (CHP 20P,75-150 μm) chromatography treatment: firstly, eluting with 20L of purified water, concentrating the eluent to obtain 580g of extract, and marking the extract as a component A; then eluting with 25L of 50% ethanol, concentrating the eluate to obtain 89g of extract, and marking as component B; then eluting with 25L of 80% ethanol, concentrating the eluate to obtain 810g extract, and marking as component C; finally, elution was performed with 15L of ethyl acetate, and the eluate was concentrated to obtain 1420g of extract, identified as component D.
(2) Molding and uric acid detection
70 Male Kunming mice were aliquoted into normal control, model, positive control, water-eluted (fraction A), 50% ethanol-eluted (fraction B), 80% ethanol-eluted (fraction C), ethyl acetate-eluted (fraction D), 10 each. Except for the normal control group, the mice in other groups are injected into the abdominal cavity by combining 0.3g/kg of potassium oxazinate and 0.3g/kg of hypoxanthine, and are continuously molded for 7 days, and the normal control group is injected with physiological saline with the same volume for 1 time per day. During the molding, the positive control group mice are irrigated with gastric allopurines according to 40mg/kg, the water elution group is irrigated with gastric allopurines according to 400mg/kg, the 50% ethanol elution group is irrigated with gastric allopurines according to 400mg/kg, the 80% ethanol elution group is irrigated with gastric allopurines according to 400mg/kg, the ethyl acetate elution group is irrigated with gastric allopurines according to 400mg/kg, and the normal control group and the model group are irrigated with 1% Tween-80 with the same volume of the administration group for 7 days, and the total gastric lavage is performed for 1 time per day. After the last administration for 1 hour, all mice were bled and tested for uric acid content.
Uric acid detection results are shown in table 1:
TABLE 1 mouse blood uric acid content (. Mu.mol/L)
"#" Indicates a significant difference (p < 0.01) from the normal control group; ". Times" indicates significant differences (p < 0.01) compared to the model group.
As shown in Table 1, the uric acid level of the normal control group was 44.40.+ -. 5.11. Mu. Mol/L, the uric acid level of the model group was 258.02.+ -. 18.63. Mu. Mol/L, and the difference between the two was significant (P < 0.01), indicating that the model formation of the mouse hyperuricemia model was successful. Uric acid values of the 50% ethanol elution group, the 80% ethanol elution group and the ethyl acetate elution group are 278.61 +/-40.07 mu mol/L, 267.80 +/-35.05 mu mol/L and 262.92 +/-26.52 mu mol/L respectively, and are not remarkably different from those of the model group; uric acid values of 148.70+/-23.42 mu mol/L and 87.22 +/-15.18 mu mol/L respectively for the water elution group and the positive control group are obviously significant compared with the model group (P < 0.01). From the above analysis, it was found that both the water elution site and the purine of the sticky note significantly reduced the blood uric acid content of mice with high uric acid, which suggests that uric acid-lowering active ingredients of the sticky note are concentrated at the water elution site (component a).
Separation and purification of uric acid-reducing active ingredient
The thin layer chromatography analysis of the component A shows that the characteristic components of the component A are single, and only one main chromatographic point is found. Treating component A with Sephadex LH-20 gel (methanol as eluent) to remove pigment and small molecule impurities (such as monosaccharide, amino acid, etc.); then purifying by preparative high pressure liquid chromatography, wherein the mobile phase is acetonitrile with water=5%:95% -50%:50%, the preparation time is 90min, the peak time of the compound is 55min, and finally 8.1g of compound 1 is obtained.
The nmr data for compound 1 are as follows:
Compound 1: brown solid ;1H NMR(400MHz,DMSO):δH 13.14(1H,s,OH-5),8.00(2H,d,J＝8.5Hz,H-2'/H-6'),6.90(2H,d,J＝8.5Hz,H-3'/H-5'),6.73(1H,s,H-3),6.19(1H,s,H-6),4.83(1H,d,J＝9.9Hz,H-1"Glu),5.23-4.67(6H,overlapped,Glu/Xyl OH),4.08-3.27(6H,overlapped,Glu H),3.90(1H,d,J＝7.2Hz,H1"'Xyl),3.01-2.31(5H,overlapped,Xyl H);13C NMR(101MHz,DMSO):δ181.8(C-4),163.6(C-2),161.4(C-7),161.2(C-4'),160.6(C-5),156.7(C-9),128.8(C-2'/C-6'),121.5(C-1'),116.0(C-3'/C-5'),105.8(C-1"'),103.8(C-10),103.3(C-8),102.3(C-3),98.5(C-6),81.8(C-2"),80.9(C-5"),78.4(C-3"),75.9(C-3"'),73.7(C-2"'),71.6(C-1"),70.3(C-4"),69.4(C-4"'),65.5(C-5"'),61.1(C-6"). was identified as vitexin xyloside (vitexin-2 "-O-xyloside) and its structural formula is shown below:
Further validation of uric acid lowering Activity of Compound 1
60 Male Kunming mice were aliquoted into normal control, model, positive control, low, medium, high, 10 each. Except for the normal control group, the mice in other groups are injected into the abdominal cavity by combining 0.3g/kg of potassium oxazinate and 0.3g/kg of hypoxanthine, and are continuously molded for 7 days, and the normal control group is injected with physiological saline with the same volume for 1 time per day. While molding, the positive control group mice were perfused with 40mg/kg of gastric allopurines, the low dose group with 20mg/kg of gastric lavage compound 1, the medium dose group with 40mg/kg of gastric lavage compound 1, the high dose group with 80mg/kg of gastric lavage compound 1, and the normal control group and the model group were perfused with 1% Tween-80 in the same volume as the administration group for 7 days, and were perfused with stomach 1 time per day. After the last administration for 1 hour, all mice were bled and tested for uric acid content.
Uric acid detection results are shown in table 2:
TABLE 2 mouse blood uric acid content (. Mu.mol/L)
"#" Indicates a significant difference (p < 0.01) from the normal control group; ". Times" indicates significant differences (p < 0.01) compared to the model group.
As shown in Table 2, the normal uric acid level was 46.06.+ -. 8.48. Mu. Mol/L, the model uric acid level was 252.84.+ -. 18.65. Mu. Mol/L, and the difference between the two was significant (P < 0.01), indicating that the model of mouse hyperuricemia was successfully modeled. The uric acid value of the low dose group is 231.39 +/-18.50 mu mol/L, and the low dose group has no significant difference compared with the model group. Uric acid values of the medium dose group and the high dose group are 181.90 +/-25.53 mu mol/L and 169.30 +/-19.54 mu mol/L respectively, the uric acid value of the positive control group is 93.76+/-15.46 mu mol/L, and three groups are remarkably different from the model group (P < 0.01), which shows that the compound 1 (namely, vitexin xyloside) has uric acid reducing activity and can remarkably reduce the blood uric acid content of high uric acid mice at the medium dose (40 mg/kg) or above.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the invention in any way, and any person skilled in the art may make modifications or alterations to the disclosed technical content to the equivalent embodiments. However, any simple modification, equivalent variation and variation of the above embodiments according to the technical substance of the present invention still fall within the protection scope of the technical solution of the present invention.
Claims (2)
1. Application of vitexin xyloside in preparing medicine with uric acid reducing effect is provided.
2. The use according to claim 1, characterized in that the preparation method of vitexin xyloside is as follows:
Leaching the sticky note with 95% ethanol, and concentrating to obtain extract A; performing MCI column chromatography on the extract A, eluting with water as eluent, and concentrating the eluent into extract B; decolorizing the extract B by gel column chromatography, removing impurities, and purifying by preparative high pressure liquid chromatography to obtain vitexin xyloside;
the gel column is selected from SephadexLH-20 gel column, and the eluent is methanol; the mobile phase of the high-pressure liquid chromatography is acetonitrile, wherein water=5% > 95% -50%.
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| CN104958311A (en) * | 2015-06-10 | 2015-10-07 | 广西中医药大学 | New use of vitexin xyloside |
| CN107581306A (en) * | 2017-08-22 | 2018-01-16 | 深圳市瑞世兴科技有限公司 | It is a kind of that there is hypoglycemic, anti-trioxypurine leaf beet health protection tea and preparation method thereof |
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| CN107581306A (en) * | 2017-08-22 | 2018-01-16 | 深圳市瑞世兴科技有限公司 | It is a kind of that there is hypoglycemic, anti-trioxypurine leaf beet health protection tea and preparation method thereof |
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| Hypouricemia effects of corn silk flavonoids in a mouse model of potassium oxonated-induced hyperuricemia;Liyan Yuan et al;《Journal of Food Biochemistry》(第45期);第1-11页，尤其是第1页摘要 * |
| Liyan Yuan et al.Hypouricemia effects of corn silk flavonoids in a mouse model of potassium oxonated-induced hyperuricemia.《Journal of Food Biochemistry》.2021,(第45期),第1-11页，尤其是第1页摘要. * |
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