CN107200761A - Two flavones and its production and use - Google Patents
Two flavones and its production and use Download PDFInfo
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- CN107200761A CN107200761A CN201610148145.5A CN201610148145A CN107200761A CN 107200761 A CN107200761 A CN 107200761A CN 201610148145 A CN201610148145 A CN 201610148145A CN 107200761 A CN107200761 A CN 107200761A
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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
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Two flavones and its production and use.The invention belongs to pharmaceutical technology field, it is related to two flavones that separation is extracted from orchid family Nervilia ford nervilia leaf (Nervilia fordii (Hance) Schltr.), they have identical parent nucleus, and chemical structural formula is as follows.The invention further relates to the effect of the anti-inflammatory activity of the two flavones and its medical usage.Such compound can combine with pharmaceutically acceptable carrier and clinically acceptable formulation is made.Preparation method of the present invention is simple, favorable reproducibility, and DNA purity is high, and there is the compound of acquisition preferable anti-inflammatory activity to act on.
Description
Technical field
It is specifically that active component is extracted from natural products the invention belongs to pharmaceutical technology field.
Background technology
Inflammation medically occupies an important position, and it is the basic pathology process of many diseases.Inflammation institute in disease
Role is considered as to make body be absorbed in too active immune system, such as asthma, allergy and rheumatic arthritis.It is anti-
Scorching medicine is divided into two kinds of steroidal anti-inflammatory medicine and NSAIDs, wherein the mankind to the use of NSAIDs from salicylic
It was found that starting the history for having had more than 100 years.NSAIDs has the anti-inflammatory determined, analgesic effect.In addition, in recent years
People are just gradually recognizing that inflammation and chronic infection are one of different tumorigenic key factors of the mankind.Estimate according to the study, extremely
Rare 15% cancer is formed by chronic inflammation development, and epidemiological study, which has been found that, periodically takes non-steroidal anti-inflammatory
The people of medicine risk reduction more cancered than the people for not taking such medicine.In China, NSAIDs has become clinic
On be only second to the second major class medication of anti-infectious agent.But, the height of the incidence of adverse reaction caused by NSAIDs, equally
It can not be ignored.It has been shown that, in the crowd using NSAIDs, there are about according to existing literature and national authority mechanism monitoring result
There is different degrees of adverse reaction in 20%-25%, is mainly shown as that gastrointestinal reaction, nervous system reaction, hepatic and renal function are anti-
Should and cardiovascular system reaction etc..
Inflammatory cell can produce numerous materials for helping tumour formation, growth and survival, and one of them is nitric oxide
(NO).NO is the gas molecule with bioactivity, is the important regulatory factor of cell-tocell transmission, and has mediated cell to exempt from
The function of epidemic disease and inflammation toxicity.NO excessive generation is closely related with inflammation, at acute inflammation position, and inflammation-causing substance and inflammation are situated between
Matter can induce or increase NO synthesis and release, and NO has cytotoxicity in itself, moreover it is possible to free group reaction generation such as ONOO-
Equimolecular, causes toxicity to increase, so as to promote inflammation part to ooze out and oedema.
The anti-inflammatory of the effect such as " clearing heat and detoxicating ", " dispelling wind and eliminating dampness ", " strengthening the body resistance to consolidate the constitution " and modern medicine in China's traditional Chinese medicine,
Immune idea is closely related, and toxic side effect is small, aboundresources.Therefore by using modern bioactivity screening mould
Type, efficient, toxic side effect low anti-inflammatory active ingredient or lead compound are searched out from Chinese herbal medicine, especially effectively suppresses NO
The flavone compound of release, and then it is the medicine for having prevention and treatment to inflammation to develop.
The content of the invention
It is an object of the invention to provide two extracted from ford nervilia leaf flavones and its production and use.
The technical scheme that the present invention solves above-mentioned technical problem is as follows:
Ford nervilia leaf (Nervilia fordii (Hance) Schltr.) medicinal material that 8kg is dried is separately added into 8L 95% (body
Product ratio, similarly hereinafter) alcohol reflux extract twice, each 2h.Medicinal material residue after alcohol extracting uses 8L distilled water refluxing extraction respectively again
Twice, each 2h.Merge Aqueous extracts twice, be concentrated under reduced pressure, obtain crude extract 1022g.By D101 macroreticular resins on crude extract,
6 flow points are obtained after alcohol-water (0: 100~100: 0) gradient elution, numbering is Fr.1-6;Wherein, the 5th flow point Fr.5 is obtained
To 357g, ODS-C is used186 Arius point are obtained after column chromatography, methanol-water (0: 100~100: 0) gradient elution, numbering is
Fr.51-56;4th Arius point Fr.54 obtains 4.8g, through preparing liquid phase separation, chromatographic condition:Mobile phase is acetonitrile-water (25
: 75), chromatographic column is YMC ODS-A (20 × 250mm, 10 μm), and flow velocity 8.0ml/min, ultraviolet detection wavelength is 265nm, is produced
To two compounds, its structure is determined by MS, NMR etc..
The benefit of the present invention is imitated:
1. there is provided the preparation method that two flavones are obtained from ford nervilia leaf.
2. two flavones that the present invention is obtained are compared with existing clinical synthetic drug, not only with anti-inflammatory activity it is good,
The low advantage of toxic side effect, and from traditional Chinese medicine, it is safe and reliable, with very good prospect in medicine, can make including
But it is not limited to the various formulations such as granule, tablet, injection.
Brief description of the drawings
Fig. 1 is Nervilifordin K's1H-NMR
Fig. 2 is Nervilifordin K's13C-NMR
Fig. 3 is Nervilifordin K HMBC
Fig. 4 is Nervilifordin K HSQC
Fig. 5 is Nervilifordin K high resolution mass spectrum figure
Fig. 6 is Nervilifordin L's1H-NMR
Fig. 7 is Nervilifordin L's13C-NMR
Fig. 8 is Nervilifordin L HMBC
Fig. 9 is Nervilifordin L ESI-MS
Figure 10 is separation process figure
Embodiment
With reference to embodiment, the invention will be further described.
Embodiment 1
Ford nervilia leaf (Nervilia fordii (Hance) Schltr.) medicinal material that 8kg is dried is separately added into 8L 95% (body
Product ratio, similarly hereinafter) alcohol reflux extract twice, each 2h.Medicinal material residue after alcohol extracting uses 8L distilled water refluxing extraction respectively again
Twice, each 2h.Merge Aqueous extracts twice, be concentrated under reduced pressure, obtain crude extract 1022g.By D101 macroreticular resins on crude extract,
6 flow points are obtained after alcohol-water (0: 100~100: 0) gradient elution, numbering is Fr.1-6;Wherein, the 5th flow point Fr.5 is obtained
To 357g, ODS-C is used186 Arius point are obtained after column chromatography, methanol-water (0: 100~100: 0) gradient elution, numbering is
Fr.51-56;4th Arius point Fr.54 obtains 4.8g, through preparing liquid phase separation, chromatographic condition:Mobile phase is acetonitrile-water (25
: 75), chromatographic column is YMC ODS-A (20 × 250mm, 10 μm), and flow velocity 8.0ml/min, ultraviolet detection wavelength is 265nm, i.e.,
Obtain two compounds, by MS, NMR etc. determine its structure, be respectively designated as Nervilifordin K and
Nervilifordin L.Structure is as shown in shown below.
Following table is the NMR signal ownership of two compounds.
The NMR Data of table 1 (600and 150MHz, resp., in DMSO-d6)of Nervilifordin K and
L. δ in ppm, J in Hz.
Pharmacological experiment:
Mtt assay evaluates cytotoxicity, and the drug concentration for choosing no cytotoxicity is studied.Take RAW264.7 mouse macrophages
Cell, by 2 × 105/ ml density is inoculated in 96 porocyte culture plates (100 μ l/ holes).After adherent 24h, 50 μ l are added per hole whole
The LPS (blank control group adds isometric phosphate buffer PBS) that concentration is 1 μ g/ml, in 37 DEG C, 5%CO2It is incubated 2h
Afterwards, experimental group adds the sample solution (blank control group and model group add isometric serum free medium) of various concentrations,
Each concentration, which sets to be incubated in 4 multiple holes, incubator after 24h, draws the μ l of culture supernatant 50 into ELISA Plate, adds in equal volume
(Griess reagent As are 0.1%N- naphthodiamide hydrochlorides, and Griess reagents B is 5% by Griess reagent As and Griess reagents B
H3PO4Containing 1% P-aminobenzene-sulfonamide, with preceding 1: 1 mixing), react at room temperature the light absorption value determined after 10min at 540nm.Ground plug
Meter Song Wei positive control medicines.
It is respectively 0,1,5,10,20,50 μm of ol/l NaNO with concentration2Standard curve is drawn, according to NaNO2Standard curve
Calculate NO in cell culture supernatant2 -Concentration and the inhibiting rate that is discharged to NO, inhibiting rate calculation formula is:
22 flavones of table discharge NO influence to RAW264.7 cells
Conclusion:The toxicity for the mouse macrophage RAW264.7 that 2 compounds are induced LPS is determined using mtt assay, and is surveyed
The fixed influence to RAW264.7 Hemapoiesis NO, as a result finds, in the concentration range being had no significant effect to cell normal proliferative,
The NO releases for the mouse macrophage RAW264.7 that 2 compounds are induced LPS show different degrees of inhibitory activity.Anti-
The application of scorching drug field has preferable prospect.
Claims (6)
1. a kind of flavones, it is characterised in that structural formula is as follows:
2. a kind of flavones, it is characterised in that structural formula is as follows:
3. the preparation method of flavones as claimed in claim 1 or 2, it is characterised in that operation is as follows:Ford nervilia leaf passes through alcohol extracting, water
Carry, macroreticular resin elution, column chromatography, prepare liquid phase separation after, obtain flavones described in claim 1 or 2.
4. the preparation method of flavones as claimed in claim 3, it is characterised in that the macroreticular resin is D101 types, the post layer
Analyse as ODS-C18Post.
5. the preparation method of flavones as claimed in claim 3, it is characterised in that operation is as follows:
95% (volume ratio, similarly hereinafter) alcohol reflux that the ford nervilia leaf medicinal material that 8kg is dried is separately added into 8L is extracted twice, each 2h;
Medicinal material residue after alcohol extracting uses 8L distilled water refluxing extraction twice respectively again, each 2h;Merge Aqueous extracts twice, depressurize dense
Contracting, obtains crude extract 1022g;By D101 macroreticular resins on crude extract, obtained after alcohol-water (0: 100~100: 0) gradient elution
6 flow points, numbering is Fr.1-6;Wherein, the 5th flow point Fr.5 obtains 357g, uses ODS-C18Column chromatography, methanol-water (0: 100
~100: 6 Arius point 0) are obtained after gradient elution, numbering is Fr.51-56;4th Arius point Fr.54 obtains 4.8g, through system
Standby liquid phase separation, chromatographic condition:Mobile phase is acetonitrile-water (25: 75), and chromatographic column is YMC ODS-A (20 × 250mm, 10 μm),
Flow velocity 8.0ml/min, ultraviolet detection wavelength is 265nm, obtains flavones described in claim 1 or 2.
6. the purposes of flavones as claimed in claim 1 or 2, it is characterised in that the flavones is used to prepare anti-inflammatory drug.
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CN201610148145.5A CN107200761A (en) | 2016-03-16 | 2016-03-16 | Two flavones and its production and use |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109082774A (en) * | 2018-09-05 | 2018-12-25 | 华南理工大学 | A kind of anti-oxidant nano-fiber composite film and preparation method and application containing Folium Nerviliae fordii extract |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1872282A (en) * | 2006-01-13 | 2006-12-06 | 广州中医药大学 | Active extractive of Foliumnerviliae, preparation method and application |
CN102183517A (en) * | 2011-03-08 | 2011-09-14 | 广西医科大学 | Method for determining general flavone content |
CN102633784A (en) * | 2012-04-11 | 2012-08-15 | 广西医科大学 | Two new flavone C-glycoside compounds as well as preparation method and application thereof |
CN102887928A (en) * | 2012-03-21 | 2013-01-23 | 广西壮族自治区药用植物园 | Flavonoids from nervilia fordii and preparation method and use thereof |
-
2016
- 2016-03-16 CN CN201610148145.5A patent/CN107200761A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1872282A (en) * | 2006-01-13 | 2006-12-06 | 广州中医药大学 | Active extractive of Foliumnerviliae, preparation method and application |
CN102183517A (en) * | 2011-03-08 | 2011-09-14 | 广西医科大学 | Method for determining general flavone content |
CN102887928A (en) * | 2012-03-21 | 2013-01-23 | 广西壮族自治区药用植物园 | Flavonoids from nervilia fordii and preparation method and use thereof |
CN102633784A (en) * | 2012-04-11 | 2012-08-15 | 广西医科大学 | Two new flavone C-glycoside compounds as well as preparation method and application thereof |
Non-Patent Citations (2)
Title |
---|
LI-WEN TIAN,等: "7-O-Methylkaempferol and -quercetin Glycosides from the Whole Plant of Nervilia fordii", 《JOURNAL OF NATURAL PRODUCTS》 * |
焦杨,等: "青天葵黄酮F的抗炎作用", 《中国医药工业杂志》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109082774A (en) * | 2018-09-05 | 2018-12-25 | 华南理工大学 | A kind of anti-oxidant nano-fiber composite film and preparation method and application containing Folium Nerviliae fordii extract |
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Application publication date: 20170926 |