CN104288169B - A kind of flavonoid glycoside compound and its production and use - Google Patents
A kind of flavonoid glycoside compound and its production and use Download PDFInfo
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- CN104288169B CN104288169B CN201410454217.XA CN201410454217A CN104288169B CN 104288169 B CN104288169 B CN 104288169B CN 201410454217 A CN201410454217 A CN 201410454217A CN 104288169 B CN104288169 B CN 104288169B
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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 kind of flavonoid glycoside compound and preparation method and application.Preparation method：(1) flos carthami extracting in water is taken, is filtered；The dregs of a decoction add water extraction, filtering；Merging filtrate, concentrate, cool down, centrifugation；Supernatant injects macroreticular resin, and successively with water, ethanol elution, ethanol eluate adds 95% ethanol to carry out alcohol precipitation again after concentrating, and supernatant and residue are separated after alcohol precipitation, and residue merges supernatant and filtrate, concentration is dry, obtains safflower extract xeraphium through centrifugal filtration；(2) the safflower extract xeraphium of step (1) is taken through C18 pillar layer separations, using methanol-water gradient elution, a flow point is collected per 100mL, flow point isolates and purifies through preparing liquid phase HPLC, using C18 posts, with 254nm wavelength detectings, acetonitrile water elution, the compounds of this invention is obtained.Compound of the present invention can be used for treating cardiovascular and cerebrovascular disease.
Description
Technical field
The present invention relates to pharmaceutical technology field, and flavonoid glycoside compound and its preparation side are extracted more particularly to from Chinese medicine
Method and purposes
Background technology
Safflower dries flower for feverfew safflower (Carthamus tinctorius L.), is annual herb plant,
High 30~120cm, stem is upright, leaf alternate, capitulum basidixed, summer flower by xanthochromia it is red when pluck, dry in the shade or dry.Originate in new
The ground such as boundary, Henan, Zhejiang, Sichuan.
Safflower first recorded in《Kaibao Bencao》.《Compendium of Materia Medica》Record, safflower " can invigorate blood circulation, moisturize, relieve pain, dissipate swelling and pain warp ".
Its acrid flavour temperature, the thoughts of returning home, Liver Channel.With invigorate blood circulation, blood stasis removing analgesic.For Amenorrhea, dysmenorrhoea, lochia, abdominal mass lump in the abdomen, fall and flutter
Damage, sore swell and ache curative.Clinically it is used to treat the diseases such as coronary heart disease, myocardial infarction and cerebral thrombus.Modern pharmacology research shows,
Safflower has improvement heart and brain blood oxygen supply, mitigates ischemia injury, anticoagulation, resist myocardial ischemia, suppress platelet aggregation, antioxygen
Change, antitumor and anti-inflammatory etc. act on.
Compound isolated from safflower includes flavonoids, alkaloids, lignanoids, organic acid, alkane at present
Base glycols and polyacetylene compound etc..Wherein flavone compound is most study in safflower, most important chemical composition.It is yellow
Generally there is ketone compounds anti-oxidant, anti-inflammatory, anticancer, antiatherosclerosis, antiallergy, anti-mutation and suppression blood platelet to coagulate
A variety of physiologically actives such as poly-.
Cardiovascular and cerebrovascular disease is the general designation of angiocardiopathy and cranial vascular disease, refer to due to hyperlipidemia, blood is sticky,
The common name of ischemic or hemorrhagic disease occurs for heart, brain and body tissue caused by atherosclerosis, hypertension etc..
The characteristics of cardiovascular and cerebrovascular disease is that incidence of disease height, disability rate height, death rate height, high recurrence rate, complication are more, and the whole world is died from every year
The number of cardiovascular and cerebrovascular disease is up to 15,000,000 people, turns into the number one killer for threatening human health.Safflower is to cardio-cerebrovascular
Effect widely approved may there is anti-oxidant, anti-artery congee with its main active flavone compound
Sample hardens and suppression platelet aggregation is relevant.
The content of the invention
A kind of flavonoid glycoside compound with bioactivity is prepared in present invention extraction from Chinese medicine safflower, and is provided
It is preparing the application in treating 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 following steps：
(1) flos carthami adds 10~15 times of amount purified water immersions, extracts 0.5~1h, filters, filtrate is standby；The dregs of a decoction add 8 again
~12 times of amount purified waters, decoct extraction 1~3 time, every time 0.5~1h, filtration, merging filtrate, be concentrated into relative density 1.05~
1.10, room temperature is cooled to, is centrifuged, in supernatant injection macroreticular resin, successively with water, 3~10% ethanol elutions, is collected respectively each
Eluent, alcohol elution are concentrated into relative density 1.01~1.05, add 5~10 times of 95% ethanol of amount, it is small to refrigerate 10~20
When, supernatant is poured out, residue centrifugal filtration, collects filtrate, merges supernatant and filtrate, ethanol is reclaimed, obtains concentrate, concentrate
It is standby through dry safflower extract xeraphium：
(2) the safflower extract xeraphium of step (1) is taken through C18 pillar layer separations, using methanol-water gradient elution, first
Determining alcohol rises to 80% from 5%, and the flow velocity of eluent is 3~5ml/min, and a flow point is collected per 100mL, collects concentration and is
20~30% methanol-water eluted fraction, flow point isolate and purify through preparing liquid phase HPLC, using C18 posts, are examined with 254nm wavelength
Survey, the elution of 12% acetonitrile-water, obtain the compounds of this invention.
Preferably, flos carthami adds the purified water of 12 times of amount volumes to soak 0.5~1h, and 0.5~1h is extracted after immersion：
Preferably, the dregs of a decoction add 10 times of amount volume purified waters again, extract 2 times, 0.5~1h every time；
Preferably, macroreticular resin can be non-polar macroporous resin or low pole macroreticular resin；
Preferably, macroreticular resin includes but is not limited to D101 macroreticular resins, HPD-100 macroreticular resins, HPD-300 macropore trees
Fat, X-5 macroreticular resins, H103 macroreticular resins, AB-8 macroreticular resins；
Most preferably, from D101 macroreticular resins；
Preferably, eluent is followed successively by water, 5% ethanol in step (1)；
Preferably, 25% methanol-water eluted fraction is collected in step (2).
Inventor learns to do section by physicochemical property and Modern spectroscopy and has carried out Structural Identification to above-claimed cpd, it was demonstrated that the change
Compound is flavonoid glycoside compound described in claim 1.
It is another object of the present invention to provide the compound to prepare the application in treating cardiovascular and cerebrovascular disease.
Brief description of the drawings
The HR-ESI-Q-TOF-MS of Fig. 1 the compounds of this invention
Fig. 2 the compounds of this invention1H-NMR is composed
Fig. 3 the compounds of this invention13C-NMR is composed
The hsqc spectrum of Fig. 4 the compounds of this invention
The HMBC spectrums of Fig. 5 the compounds of this invention
Embodiment
In order that those skilled in the art are better understood from technical scheme, with reference to specific embodiment to this
Invention is further elaborated.
The preparation of the compounds of this invention of embodiment 1
(1) flos carthami adds 10~15 times of amount purified water immersions, extracts 0.5~1h, filters, filtrate is standby；The dregs of a decoction add 8 again
~12 times of amount purified waters, decoct extraction 1~3 time, every time 0.5~1h, filtration, merging filtrate, be concentrated into relative density 1.05~
1.10, room temperature is cooled to, is centrifuged, in supernatant injection macroreticular resin, successively with water, 3~10% ethanol elutions, is collected respectively each
Eluent, alcohol elution are concentrated into relative density 1.01~1.05, add 5~10 times of 95% ethanol of amount, it is small to refrigerate 10~20
When, pour out supernatant, residue centrifugal filtration, merge supernatant and filtrate, reclaim ethanol, concentrate is through dry safflower extract
Xeraphium, it is standby；
(2) the safflower extract xeraphium of step (1) is taken through C18 pillar layer separations, using methanol-water gradient elution, first
Determining alcohol rises to 80% from 5%, and the flow velocity of eluent is 3~5mL/min, and a flow point is collected per 100mL, collects concentration and is
20~30% methanol-water eluted fraction, flow point isolate and purify through preparing liquid phase HPLC, using C18 posts, are examined with 254nm wavelength
Survey, the elution of 12% acetonitrile-water, obtain the compounds of this invention.
The Structural Identification of the compounds of this invention of embodiment 2
The compounds of this invention is pale yellow powder, the molecular ion peak [M-H] that ESI-MS is provided-For 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 reactions and ferric trichloride-potassium ferricyanide reaction are positive, and it is flavonoid glycoside to prompt it
Class compound.
The compounds of this invention1H-NMR (400MHz, DMSO-d6) (see Fig. 2) display δ 8.03 (2H, d, J=8.4Hz, H-
2 ', H-6 '), 6.89 (2H, d, J=8.4Hz, H-3 ', H-5 ') are the AA ' BB ' hydrogen signals on flavones B rings；δ 6.96 (1H, s, H-
8) it is 3 hydrogen signals of flavones；δ 5.47 (1H, d, J=7.2Hz, 3-O-Glc-1), 5.23 (1H, d .J=7.2Hz, 7-O-
GlcA-1) it is two sugared anomeric proton signals；Low field δ 12.39 (1H, s, 5-OH), the 10.20 (- OH of 1H, s, 4 '), 8.63
(1H, s, 6-OH) is 3 hydroxyl signals.13C-NMR (100MHz, DMSO-d6) 27 carbon signals are shown (see Fig. 3), wherein 15
For the carbon signal of flavones, remaining 12 are the carbon signal on 2 glucose, and wherein δ 170.5 is the carbon signal of glucuronic acid,
The compound is prompted to have a glucuronic acid.Part carbon signal is belonged to by hsqc spectrum (see Fig. 4).Composed in HMBC
Glucuronic acid anomeric proton δ 5.23 is related to δ 151.6 (C-7) in (see Fig. 5), has not seen that δ 5.47 closes with any carbon phase, but δ
157.4 (C-2), 133.5 (C-3) they are the characteristic feature of 3-O- glycosides, by C ring carbons modal data and 6-hydroxykaempferol-3,
6-di- β-D-glucoside-7- β-D-glucuronide C ring carbon modal datas compare, and discovery is basically identical, so determining
This compound is 6-hydroxykaempferol-3- β-D-glucoside-7- β-D-glucuronide.By SciFinder
Scholar network retrievals, do not find relevant report.
The compounds of this invention1H-NMR data are：1H-NMR (400MHz, DMSO-d6)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 invention13C-NMR data are：13C-NMR (100MHz, DMSO-d6)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).
Effect study of the compounds of this invention of embodiment 3 to isoprel mouse resist oxygen lack model
1 material
1.1 experimental animal SPF levels Kunming mouses 60, male and female half and half, body weight (20 ± 2) g, by Zhejiang Province experimental animal
Center provides, quality certification number：SCXK (Zhejiang) 20130033.
1.2 medicines and reagent hydrochloric acid Verapamil piece, 40mg/ pieces, Shanghai Sine Pharmaceutical Co., Ltd., lot number：131101
B；Isoprenaline hydrochloride, 1mg/2mL, Shanghai Hefeng Pharmaceutical Co., Ltd., lot number：130101.
2 experimental methods
60 mouse are randomly divided into 6 groups, every group 10 (male and female half and half).I.e. normal group, model group, Verapamil group,
The compounds of this invention low dose group, the compounds of this invention middle dose group, the compounds of this invention high dose group.Successive administration 7 days, end
After secondary administration after 30min, in addition to normal group, each group is by 10mg/kg dosage intraperitoneal injection isoprenaline hydrochloride, after 15min
Each mouse is put into the 250mL wide-mouth bottles containing 20g soda limes, vaseline sealing, observes and records mouse diing time.Experiment knot
Fruit is as follows：
The mouse oxygen deficit tolerance experimental result of table 1
Compared with normal group,ΔP ＜ 0.05ΔΔP ＜ 0.01；Compared with model group,*P ＜ 0.05,**P ＜ 0.01
Experimental result is shown, compared with normal group, injection isoprel can substantially increase myocardial oxygen consumption, reduce small
Mouse hypoxia endurance time, show modeling success (p ＜ 0.01)；Compared with model group, positive drug Verapamil group can effectively extend small
The mouse resist oxygen lack dead time (p ＜ 0.05), when high dose administration group can significantly extend dead mouse in the compounds of this invention
Between (p ＜ 0.05).
The compounds of this invention of embodiment 4 causes the Effect study of Rat Experimental myocardial infarction and ischemia model to pituitrin
1 material
1.1 experimental animal SPF level SD rats 60, male and female half and half, 150~180g of body weight, by Zhejiang Province experimental animal
The heart provides, quality certification number：SCXK (Zhejiang) 20130033.
1.2 medicines and reagent hydrochloric acid Verapamil piece, 40mg/ pieces, Shanghai Sine Pharmaceutical Co., Ltd., lot number：131101
B；Posterior pituitary injection, 6 units/2mL, Shanghai the first biochemical drug Co., Ltd, lot number：130501；SOD, MDA kit
It is purchased from and is respectively in capital English biotechnology research institute, lot number：20130101M, 20130410；LDH, CK kit are purchased from
In Zhongsheng Beikong Biological Science ＆ Technology Co., Ltd., lot number is respectively：20130212,20130212.
60 rats are randomly divided into normal group, model group, Verapamil group (32.4mg/kg), the present invention by 2 experimental methods
Compound low dose group (10mg/kg), the compounds of this invention middle dose group (20mg/kg), the compounds of this invention high dose group
(40mg/kg), presses 10mL/kg gastric infusions 1 time daily, and successive administration 7 days, normal group, model group are pure to same volume daily
Water, 30min after last dose, by rat anesthesia, fixation of lying on the back, record standard II lead electrocardiogram.The tongue after electrocardiogram is stable
Inject and finish in lower intravenous injection pituitrin 0.75u/kg, 10s, 0- after recording (0s) before injecting respectively and injecting
15min electrocardiogram, take T wave-amplitudes rise 0.1 or reduce 0.05mv as model success, record the change of T wave-amplitudes, as a result see
Table 2.After injection of pituitrin 40min, abdominal aortic blood, separates serum immediately, detects SOD, MDA, CK, LDH in serum
Level, it the results are shown in Table 3.
T wave-amplitudes change in the Acute Myocardial Ischemia in Rats of table 2
Compared with normal group,ΔP ＜ 0.05ΔΔP ＜ 0.01；Compared with model group,*P ＜ 0.05,**P ＜ 0.01
Experimental result is shown, compared with normal group, model group T ripple changing values obviously higher than normal group, wherein 30s,
Show that pituitrin is injected with significant difference (p ＜ 0.05) compared with normal group in tetra- points of 1min, 5min, 10min
After rat T wave-amplitudes can be made substantially to become big；Compared with model group, Verapamil group T ripples changing value in each point electrocardiogram has
It is obvious to reduce, wherein with significant difference (p ＜ 0.05) compared with model group in tri- points of 30s, 1min, 5min；This hair
The low middle high dose of bright compound can reduce T ripple amplitudes of variation, wherein medicine low dose group amplitude of variation and model in 1min
There were significant differences for group (being respectively p ＜ 0.01, p ＜ 0.05), and the compounds of this invention middle dose group is in 1min, 5min, 10min time-varying
There were significant differences with model group for change amplitude (be respectively p ＜ 0.05, p ＜ 0.01), the compounds of this invention high dose group 30s,
There were significant differences (being respectively p ＜ 0.01, p ＜ 0.01, p ＜ 0.05) for amplitude of variation and model group when 1min, 5min, 10min.
Each group rat blood serum SOD, MDA, CK, LDH contents level of table 3 compares
Compared with normal group,ΔP ＜ 0.05ΔΔP ＜ 0.01；Compared with model group,*P ＜ 0.05,**P ＜ 0.01
Experimental result is shown, compared with normal group, model group MDA, CK, LDH index has significant difference (p ＜ 0.05),
SOD changes trend but indifference (p ＞ 0.05)；Compared with model group, the equal no difference of science of statistics of each group SOD (p ＞ 0.05)；Dimension
La Pa meter groups MDA has significant difference (p ＜ 0.05), and the low middle high dose group of the compounds of this invention can significantly reduce LDH levels
(p ＜ 0.01), high dose group can significantly raise CK levels (p ＜ 0.05), the compounds of this invention in blood plasma in the compounds of this invention
It is horizontal (p ＜ 0.01) that high dose group can significantly reduce blood plasma MDA.
Claims (2)
1. a kind of preparation method of the compound as shown in structural formula I, it is characterised in that comprise the following steps：
(1) flos carthami adds 10~15 times of amount purified water immersions, extracts 0.5~1h, filtration, filtrate is standby, and the dregs of a decoction add 8~12 again
Amount purified water again, extraction 1~3 time is decocted, every time 0.5~1h, filtration, merging filtrate, is concentrated into relative density 1.05~1.10,
Room temperature is cooled to, is centrifuged, in supernatant injection macroreticular resin, successively with water, 3~10% ethanol elutions, collects each elution respectively
Liquid, alcohol elution are concentrated into relative density 1.01~1.05, add 5~10 times of 95% ethanol of amount, refrigerate 10~20 hours, incline
Go out supernatant, residue centrifugal filtration, obtain filtrate, merge supernatant and filtrate, reclaim ethanol, obtain concentrate, concentrate is through drying
Safflower extract xeraphium is obtained, it is standby；
(2) the safflower extract xeraphium in step (1) is taken through C18 pillar layer separations, using methanol-water gradient elution, methanol
Concentration rises to 80% from 5%, and the flow velocity of eluent is 3~5mL/min, and a flow point is collected per 100mL, collects concentration and is
20%~30% methanol-water eluted fraction, flow point isolates and purifies through preparing liquid phase HPLC, using C18 posts, with 254nm wavelength
Detection, 12% acetonitrile-water elution, obtains the compound as shown in structural formula I；
Wherein, macroreticular resin described in step (1) includes non-polar macroporous resin and low pole macroreticular resin.
2. preparation method as claimed in claim 1, it is characterised in that comprise the following steps
(1) flos carthami adds 12 times of amount volume purified water immersions, extracts 0.5~1h, filters, filtrate is standby；The dregs of a decoction add 10 times again
Measure volume purified water, decoct extraction 2 times, every time 0.5~1h, filtration, merge 3 filtrates, be concentrated into relative density 1.05~
1.10, room temperature is cooled to, is centrifuged, in supernatant injection macroreticular resin, successively with water, 5% ethanol elution, collects each elution respectively
Liquid, alcohol elution are concentrated into relative density 1.01~1.05, then add 8 times of 95% ethanol of amount, refrigerate 10~20 hours, pour out
Supernatant, residue centrifugal filtration obtain filtrate, merge supernatant and filtrate, reclaim ethanol, obtain concentrate, and concentrate is through dry
Safflower extract xeraphium, it is standby；
(2) the safflower extract xeraphium of step (1) is taken through C18 pillar layer separations, it is dense using methanol-water gradient elution, methanol
Degree rises to 80% from 5%, and the flow velocity of eluent is 3~5mL/min, one flow point of collection per 100mL, and 25% methanol of collection-
The eluted fraction of water, flow point isolates and purifies through preparing liquid phase HPLC, using C18 posts, with 254nm wavelength detectings, 12% acetonitrile-water
Elution, obtains the compound as shown in structural formula I.
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| CN1403080A (en) * | 2002-10-21 | 2003-03-19 | 中国人民解放军第二军医大学 | Application of kaempferol and its derivative in preparing medicine for cardiac and cerebral vascular diseases |
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| CN101812099B (en) * | 2009-02-24 | 2013-05-01 | 上海医药工业研究院 | Flavonoids compound and synthesis method and application thereof |
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| 凉粉草中抗缺氧化学成分;秦立红等;《沈阳药科大学学报》;20061025(第10期);56-59 * |
| 山奈酚和槲皮素对乳鼠心肌缺氧及过氧化损伤的保护作用;汤喜兰;《中药药理与临床》;20121231;第28卷(第1期);633-636 * |
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