CN104288169A - Flavone glycoside compound and preparation method and application thereof - Google Patents
Flavone glycoside compound and preparation method and application thereof Download PDFInfo
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- CN104288169A CN104288169A CN201410454217.XA CN201410454217A CN104288169A CN 104288169 A CN104288169 A CN 104288169A CN 201410454217 A CN201410454217 A CN 201410454217A CN 104288169 A CN104288169 A CN 104288169A
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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
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- 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
Abstract
The invention discloses a flavone glycoside compound and a preparation method and an application thereof. The preparation method comprises the steps: (1) taking a safflower medicinal material, adding water, extracting, and filtering; adding water into the medicinal residue, extracting, and filtering; merging the filtrates, concentrating, cooling, and centrifuging; and injecting the supernatant into a macroporous resin, eluting successively by water and ethanol, concentrating the ethanol eluate, then adding a 95% ethanol, carrying out alcohol precipitation, after alcohol precipitation, separating a supernatant and a residue, carrying out centrifugal filtration on the residue, merging the supernatant and the filtrate, concentrating, drying, and thus obtaining a safflower extract dry powder; and (2) taking the safflower extract dry powder of the step (1), carrying out chromatography separation by a C18 column, carrying out methanol-water gradient elution, collecting one fraction every 100 mL, carrying out separation and purification on the fractions by preparative liquid HPLC, adopting the C18 column, detecting with the wavelength of 254 nm, carrying out acetonitrile-water elution, and thus obtaining the compound. The compound can be used for treatment of cardiovascular and cerebrovascular diseases.
Description
Technical field
The present invention relates to medical art, particularly from Chinese crude drug, extract flavonoid glycoside compound and its production and use
Background technology
Flos Carthami is the dried floral of feverfew Flos Carthami (Carthamus tinctorius L.), is annual herb plant, high 30 ~ 120cm, and stem is upright, leaf alternate, and head inflorescence top is raw, plucks, dry in the shade or dry when summer, flower was red by xanthochromia.Originate in the ground such as Xinjiang, Henan, Zhejiang, Sichuan.
Flos Carthami begins to be loaded in " Kaibao Bencao ".Compendium of Material Medica is recorded, Flos Carthami can " invigorate blood circulation, moisturize, pain relieving, loose swell and ache through ".Its acrid in the mouth temperature, GUIXIN, Liver Channel.There is promoting blood circulation to restore menstrual flow, eliminating stasis to stop pain.For amenorrhea, dysmenorrhea, lochia, lump in the abdomen mass in the abdomen, injury from falling down, skin infection swells and ache.Be used for the treatment of the diseases such as coronary heart disease, myocardial infarction and cerebral thrombosis clinically.Modern pharmacology research shows, the effects such as Flos Carthami is improved the supply of heart and brain blood oxygen, alleviates ischemia injury, anticoagulation, resists myocardial ischemia, anticoagulant, antioxidation, antitumor and antiinflammatory.
From Flos Carthami, be separated the compound obtained comprises flavonoid, alkaloids, lignanoids, organic acid, alkyl diol class and polyacetylene compound etc. at present.Wherein flavone compound is most study in Flos Carthami, topmost chemical composition.Flavone compound usually has antioxidation, antiinflammatory, anticancer, atherosclerosis, antiallergic, mutation and suppresses the multiple physiologically actives such as platelet aggregation.
Cardiovascular and cerebrovascular disease is the general designation of cardiovascular disease and cerebrovascular disease, makes a general reference because the common name of ischemic or hemorrhage occurs for the heart that hyperlipemia, blood are sticky, atherosclerosis, hypertension etc. cause, brain and body tissue.The feature of cardiovascular and cerebrovascular disease is that sickness rate is high, disability rate is high, mortality rate is high, relapse rate is high, complication is many, and the number of cardiovascular and cerebrovascular disease is died from every year up to 1,500 ten thousand people in the whole world, becomes the number one killer threatening human health.The effect of Flos Carthami to cardio-cerebrovascular is approved widely, may with its main active flavone compound, have antioxidation, atherosclerosis and suppress platelet aggregation relevant.
Summary of the invention
The present invention extracts and prepares one and have bioactive flavonoid glycoside compound from Chinese medicine safflower, and provides its application in preparation treatment cardiovascular and cerebrovascular diseases medicament.
Specifically, the invention provides a kind of flavonoid glycoside compound, shown in its structural formula as I:
Present invention also offers the preparation method of above-claimed cpd, comprise the steps:
(1) flos carthami adds 10 ~ 15 times amount purified water immersions, and extract 0.5 ~ 1h, filter, filtrate is for subsequent use, medicinal residues add 8 ~ 12 times amount purified water again, decoct extraction 1 ~ 3 time, each 0.5 ~ 1h, filter, merging filtrate, be concentrated into relative density 1.05 ~ 1.10, be cooled to room temperature, centrifugal, supernatant injects in macroporous resin, successively with water, 3 ~ 10% ethanol elutions, collect each eluent respectively, alcohol elution is concentrated into relative density 1.01 ~ 1.05, add 5 ~ 10 times amount 95% ethanol, cold preservation 10 ~ 20 hours, incline and supernatant, residue centrifugal filtration, collect filtrate, merge supernatant and filtrate, reclaim ethanol, obtain concentrated solution, concentrated solution drying obtains Flos Carthami extract xeraphium, for subsequent use:
(2) the Flos Carthami extract xeraphium of step (1) is got through C18 pillar layer separation, adopt methanol-water gradient elution, methanol concentration rises to 80% from 5%, and the flow velocity of eluent is 3 ~ 5ml/min, and every 100mL collects a flow point, collect the methanol-water eluted fraction that concentration is 20 ~ 30%, flow point, through preparation liquid phase HPLC separation and purification, adopts C18 post, with 254nm wavelength detecting, 12% acetonitrile-water eluting, obtains the compounds of this invention.
Preferably, the purified water that flos carthami adds 12 times amount volumes soaks 0.5 ~ 1h, extracts 0.5 ~ 1h after soaking:
Preferably, medicinal residues add 10 times amount volume purified water again, extract 2 times, each 0.5 ~ 1h;
Preferably, macroporous resin can be non-polar macroporous resin or low pole macroporous resin;
Preferably, macroporous resin includes but not limited to D101 macroporous resin, HPD-100 macroporous resin, HPD-300 macroporous resin, X-5 macroporous resin, H103 macroporous resin, AB-8 macroporous resin;
Most preferred, select D101 macroporous resin;
Preferably, in step (1), eluent is followed successively by water, 5% ethanol;
Preferably, 25% methanol-water eluted fraction is collected in step (2).
Inventor has carried out Structural Identification by physicochemical property and the Modern spectroscopy section of learning to do to above-claimed cpd, confirms that this compound is for flavonoid glycoside compound described in claim 1.
Another object of the present invention is to provide the application of this compound in preparation treatment cardiovascular and cerebrovascular disease.
Accompanying drawing explanation
The HR-ESI-Q-TOF-MS of Fig. 1 the compounds of this invention
Fig. 2 the compounds of this invention
1h-NMR composes
Fig. 3 the compounds of this invention
13c-NMR composes
The hsqc spectrum of Fig. 4 the compounds of this invention
The HMBC spectrum of Fig. 5 the compounds of this invention
Detailed description of the invention
In order to make those skilled in the art better understand technical scheme of the present invention, below in conjunction with specific embodiment, the invention will be further elaborated.
The preparation of embodiment 1 the compounds of this invention
(1) flos carthami adds 10 ~ 15 times amount purified water immersions, and extract 0.5 ~ 1h, filter, filtrate is for subsequent use; Medicinal residues add 8 ~ 12 times amount purified water again, decoct extraction 1 ~ 3 time, each 0.5 ~ 1h, filter, merging filtrate, be concentrated into relative density 1.05 ~ 1.10, be cooled to room temperature, centrifugal, supernatant injects in macroporous resin, successively with water, 3 ~ 10% ethanol elutions, collect each eluent respectively, alcohol elution is concentrated into relative density 1.01 ~ 1.05, add 5 ~ 10 times amount 95% ethanol, cold preservation 10 ~ 20 hours, inclines and supernatant, residue centrifugal filtration, merge supernatant and filtrate, reclaim ethanol, concentrated solution drying obtains Flos Carthami extract xeraphium, for subsequent use;
(2) the Flos Carthami extract xeraphium of step (1) is got through C18 pillar layer separation, adopt methanol-water gradient elution, methanol concentration rises to 80% from 5%, and the flow velocity of eluent is 3 ~ 5mL/min, and every 100mL collects a flow point, collect the methanol-water eluted fraction that concentration is 20 ~ 30%, flow point, through preparation liquid phase HPLC separation and purification, adopts C18 post, with 254nm wavelength detecting, 12% acetonitrile-water eluting, obtains the compounds of this invention.
The Structural Identification of embodiment 2 the compounds of this invention
The compounds of this invention is pale yellow powder, the molecular ion peak [M-H] that ESI-MS provides
-be 639, fragment has 463 [M-H-176]
-, 301 [M-H-176-162]
-.HR-ESI-Q-TOF-MS m/z:639.1272 [M-H]
-(calcd 639.1203) (see Fig. 1).
The reaction of hydrochloric acid magnesium powder, Molish reaction and ferric chloride-potassium ferricyanide reaction are all positive, and point out it to be flavonoid glycoside compound.
The compounds of this invention
1h-NMR (400MHz, DMSO-d
6) (see Fig. 2) show δ 8.03 (2H, d, J=8.4Hz, H-2 ', H-6 '), 6.89 (2H, d, J=8.4Hz, H-3 ', H-5 ') be the AA ' BB ' hydrogen signal on flavone B ring; δ 6.96 (1H, s, H-8) is flavone 3 hydrogen signals; δ 5.47 (1H, d, J=7.2Hz, 3-O-Glc-1), 5.23 (1H, d .J=7.2Hz, 7-O-GlcA-1) are two sugared anomeric proton signals; Low field δ 12.39 (1H, s, 5-OH), 10.20 (1H, s, 4 '-OH), 8.63 (1H, s, 6-OH) are 3 hydroxyl signal.
13c-NMR (100MHz, DMSO-d
6) (see Fig. 3) show 27 carbon signals, wherein 15 is the carbon signal of flavone, and all the other 12 is the carbon signal on 2 glucoses, and wherein δ 170.5 is the carbon signal of glucuronic acid, points out this compound to have a glucuronic acid.By hsqc spectrum (see Fig. 4), part carbon signal is belonged to.In HMBC spectrum (see Fig. 5), glucuronic acid anomeric proton δ 5.23 is relevant to δ 151.6 (C-7), do not see δ 5.47 relevant to any carbon, but δ 157.4 (C-2), the typical characteristic that 133.5 (C-3) are 3-O-glycosides, by C ring carbon modal data and 6-hydroxykaempferol-3, the C ring carbon modal data of 6-di-β-D-glucoside-7-β-D-glucuronide is compared, find basically identical, so determine that this compound is 6-hydroxykaempferol-3-β-D-glucoside-7-β-D-glucuronide.Through SciFinder Scholar network retrieval, do not find relevant report.
The compounds of this invention
1h-NMR data are:
1h-NMR (400MHz, DMSO-d
6) δ: 12.39 (1H, s, 5-OH), 8.63 (1H, s, 6-OH), 6.96 (1H, s, H-8), 8.03 (2H, d, J=8.4Hz, H-2 ', H-6 '), 10.20 (1H, s, 4 '-OH), 6.89 (2H, d, J=8.4Hz, H-3 ', H-5 '); 3-O-Glc, 5.47 (1H, d, J=7.2Hz, 1-H), 3.17 (1H, t, J=8.1Hz, 2-H), 3.21 (1H, m, 3-H), 3.07 (1H, m, 4-H), 3.08 (1H, m, 5-H), 3.54 (1H, brd, J=11.7Hz, 6a-H), 3.35 (1H, brd, J=11.7Hz, 6b-H); 7-O-GlcA, 5.23 (1H, d, J=7.2Hz, 1-H), 3.39 (1H, m, 2-H), 3.33 (1H, m, 3-H), 3.42 (1H, m, 4-H), 4.04 (1H, d, J=9.4Hz, 5-H).
The compounds of this invention
13c-NMR data are:
13c-NMR (100MHz, DMSO-d
6) δ: 157.4 (C-2), 133.5 (C-3), 178.3C-4), 146.7 (C-5), 130.7 (C-6), 151.6 (C-7), 93.7 (C-8), 148.7 (C-9), 106.7 (C-10), 121.5 (C-1 '), 131.4 (C-2 ', C-6 '), 115.6 (C-3 ', C-5 '), 160.4 (C-4 '); 3-O-Glc101.1 (C-1), 74.7 (C-2), 76.9 (C-3), 70.4 (C-4), 78.0 (C-5), 61.3 (C-6); 7-O-GlcA, 100.2 (C-1), 73.3 (C-2), 75.7 (C-3), 71.7 (C-4), 75.9 (C-5), 170.5 (C-6).
Embodiment 3 the compounds of this invention is to the Effect study of isoproterenol mice anoxia enduring model
1 material
1.1 laboratory animal SPF level Kunming mouses 60, male and female half and half, body weight (20 ± 2) g, is provided by Zhejiang Province's Experimental Animal Center, the quality certification number: SCXK (Zhejiang) 20130033.
1.2 medicines and reagent hydrochloric acid verapamil sheet, 40mg/ sheet, Shanghai Sine Pharmaceutical Co., Ltd., lot number: 131101 B; Isoprenaline, 1mg/2mL, Shanghai Hefeng Pharmaceutical Co., Ltd., lot number: 130101.
2 experimental techniques
60 mices are divided into 6 groups at random, often organize 10 (male and female half and half).I.e. dosage group, the compounds of this invention high dose group in normal group, model group, verapamil group, the compounds of this invention low dose group, the compounds of this invention.Successive administration 7 days, after last administration after 30min, except normal group, press 10mg/kg dosage lumbar injection isoprenaline for each group, after 15min, each Mus is put into the 250mL wide mouthed bottle containing 20g sodica calx, vaseline seals, observed and recorded mouse diing time.Experimental result is as follows:
Table 1 mice oxygen deficit tolerance experimental result
Compare with normal group,
Δp < 0.05
Δ Δp < 0.01; Compare with model group,
*p < 0.05,
*p < 0.01
Experimental result shows, and compared with normal group, injection isoproterenol obviously can increase myocardial oxygen consumption, reduces mice hypoxia endurance time, shows modeling success (p < 0.01); Compared with model group, positive drug verapamil group effectively can extend the time (p < 0.05) of mice anoxia enduring death, and in the compounds of this invention, high dose administration group all can significant prolongation mouse diing time (p < 0.05).
Embodiment 4 the compounds of this invention causes the Effect study of Rat Experimental myocardial infarction and ischemia model to pituitrin
1 material
1.1 laboratory animal SPF level SD rats 60, male and female half and half, body weight 150 ~ 180g, is provided by Zhejiang Province's Experimental Animal Center, the quality certification number: SCXK (Zhejiang) 20130033.
1.2 medicines and reagent hydrochloric acid verapamil sheet, 40mg/ sheet, Shanghai Sine Pharmaceutical Co., Ltd., lot number: 131101 B; Posterior pituitary injection, 6 units/2mL, Shanghai first biochemical drug company limited, lot number: 130501; SOD, MDA test kit is all purchased from capital English biotechnology research institute, and lot number is respectively: 20130101M, and 20130410; LDH, CK test kit is all purchased from Zhongsheng Beikong Biological Science & Technology Co., Ltd., and lot number is respectively: 20130212, and 20130212.
60 rats are divided into dosage group (20mg/kg), the compounds of this invention high dose group (40mg/kg) in normal group, model group, verapamil group (32.4mg/kg), the compounds of this invention low dose group (10mg/kg), the compounds of this invention by 2 experimental techniques at random, press 10mL/kg gastric infusion every day 1 time, successive administration 7 days, normal group, model group every day are to same volume pure water, 30min after last administration, by rat anesthesia, lie on the back fixing, record standard II lead electrocardiogram.Sublingual vein injection of pituitrin 0.75u/kg after electrocardiogram is stable, inject complete in 10s, record the electrocardiogram of (0s) and the rear 0-15min of injection before injecting respectively, getting T wave-amplitude rising 0.1 or reducing 0.05mv is model success, the change of record T wave-amplitude, the results are shown in Table 2.After injection of pituitrin 40min, abdominal aortic blood immediately, separation of serum, detects SOD, MDA, CK, LDH level in serum, the results are shown in Table 3.
T wave-amplitude change in table 2 Acute Myocardial Ischemia in Rats
Compare with normal group,
Δp < 0.05
Δ Δp < 0.01; Compare with model group,
*p < 0.05,
*p < 0.01
Experimental result shows, compared with normal group, model group T ripple changing value is all apparently higher than normal group, wherein compare with normal group in 30s, 1min, 5min, 10min tetra-points and there is significant difference (p < 0.05), after showing pituitrin injection, rat T wave-amplitude can be made obviously to become large, compared with model group, verapamil group T ripple changing value in each point electrocardiogram all has obvious reduction, wherein compares with model group in 30s, 1min, 5min tri-points and has significant difference (p < 0.05), the low middle high dose of the compounds of this invention all can reduce T ripple amplitude of variation, its Chinese medicine low dose group when 1min amplitude of variation and model group there were significant differences (is respectively p < 0.01, p < 0.05), in the compounds of this invention, dosage group is at 1min, 5min, during 10min, there were significant differences (is respectively p < 0.05 for amplitude of variation and model group, p < 0.01), the compounds of this invention high dose group is at 30s, 1min, 5min, during 10min, there were significant differences (is respectively p < 0.01 for amplitude of variation and model group, p < 0.01, p < 0.05).
Table 3 respectively group rat blood serum SOD, MDA, CK, LDH contents level compares
Compare with normal group,
Δp < 0.05
Δ Δp < 0.01; Compare with model group,
*p < 0.05,
*p < 0.01
Experimental result shows, and compare with normal group, model group MDA, CK, LDH index have significant difference (p < 0.05), and SOD changes trend but zero difference (p > 0.05); Compared with model group, each group equal no difference of science of statistics of SOD (p > 0.05); Verapamil group MDA has significant difference (p < 0.05), the low middle high dose group of the compounds of this invention all significantly can reduce LDH level (p < 0.01), CK level (p < 0.05) in the remarkable elevate plasma of high dose group energy in the compounds of this invention, the compounds of this invention high dose group significantly can reduce blood plasma MDA level (p < 0.01).
Claims (7)
1. a flavonoid glycoside compound, shown in its structural formula as I:
2. prepare a preparation method for compound described in claim 1, it is characterized in that, comprise the following steps:
(1) flos carthami adds 10 ~ 15 times amount purified water immersions, extract 0.5 ~ 1h, filter, filtrate is for subsequent use, medicinal residues add 8 ~ 12 times amount purified water again, decoct extraction 1 ~ 3 time, each 0.5 ~ 1h, filter, merging filtrate, be concentrated into relative density 1.05 ~ 1.10, be cooled to room temperature, centrifugal, supernatant injects in macroporous resin, successively with water, 3 ~ 10% ethanol elutions, collect each eluent respectively, alcohol elution is concentrated into relative density 1.01 ~ 1.05, add 5 ~ 10 times amount 95% ethanol, cold preservation 10 ~ 20 hours, incline and supernatant, residue centrifugal filtration, obtain filtrate, merge supernatant and filtrate, reclaim ethanol, obtain concentrated solution, concentrated solution drying obtains Flos Carthami extract xeraphium, for subsequent use,
(2) Flos Carthami extract xeraphium in step (1) is got through C18 pillar layer separation, adopt methanol-water gradient elution, methanol concentration rises to 80% from 5%, and the flow velocity of eluent is 3 ~ 5mL/min, and every 100mL collects a flow point, collect the methanol-water eluted fraction that concentration is 20% ~ 30%, flow point, through preparation liquid phase HPLC separation and purification, adopts C18 post, with 254nm wavelength detecting, 12% acetonitrile-water eluting, obtains the compounds of this invention.
3. preparation method as claimed in claim 2, is characterized in that, comprise the following steps
(1) flos carthami adds 12 times amount volume purified water immersions, and extract 0.5 ~ 1h, filter, filtrate is for subsequent use, medicinal residues add 10 times amount volume purified water again, decoct extraction 2 times, each 0.5 ~ 1h, filter, merge 3 filtrates, be concentrated into relative density 1.05 ~ 1.10, be cooled to room temperature, centrifugal, supernatant injects in macroporous resin, successively with water, 5% ethanol elution, collect each eluent respectively, alcohol elution is concentrated into relative density 1.01 ~ 1.05, add 8 times amount 95% ethanol again, cold preservation 10 ~ 20 hours, incline and supernatant, residue centrifugal filtration, obtain filtrate, merge supernatant and filtrate, reclaim ethanol, obtain concentrated solution, concentrated solution drying obtains Flos Carthami extract xeraphium, for subsequent use,
(2) the Flos Carthami extract xeraphium of step (1) is got through C18 pillar layer separation, adopt methanol-water gradient elution, methanol concentration rises to 80% from 5%, and the flow velocity of eluent is 3 ~ 5mL/min, and every 100mL collects a flow point, collect the eluted fraction of 25% methanol-water, flow point, through preparation liquid phase HPLC separation and purification, adopts C18 post, with 254nm wavelength detecting, 12% acetonitrile-water eluting, obtains the compounds of this invention.
4. preparation method as claimed in claim 2, it is characterized in that, described in step (1), macroporous resin comprises non-polar macroporous resin and low pole macroporous resin.
5. the application of compound described in claim 1 in preparation treatment cardiovascular and cerebrovascular diseases medicament.
6. a pharmaceutical composition, is characterized in that, comprises compound described in claim 1.
7. be used for the treatment of a pharmaceutical composition for cardiovascular and cerebrovascular disease, it is characterized in that, compound and pharmaceutically acceptable carrier described in the claim 1 containing treatment effective dose.
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Cited By (1)
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| CN104845978A (en) * | 2015-05-19 | 2015-08-19 | 吉林农业大学 | Safflower MYB (v-myb myeloblastosis viral oncogene homolog (avian)) gene and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104845978A (en) * | 2015-05-19 | 2015-08-19 | 吉林农业大学 | Safflower MYB (v-myb myeloblastosis viral oncogene homolog (avian)) gene and application thereof |
| CN104845978B (en) * | 2015-05-19 | 2018-04-03 | 吉林农业大学 | Safflower MYB12 genes and its application |
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