CN110305094A - Two kinds of flavone compounds and its extraction separation method and purposes in purslane - Google Patents
Two kinds of flavone compounds and its extraction separation method and purposes in purslane Download PDFInfo
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- CN110305094A CN110305094A CN201910640045.8A CN201910640045A CN110305094A CN 110305094 A CN110305094 A CN 110305094A CN 201910640045 A CN201910640045 A CN 201910640045A CN 110305094 A CN110305094 A CN 110305094A
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Abstract
The present invention relates to traditional Chinese medicine extractions, separation field, more particularly to extracting and developing and two kinds of new flavone compounds and its extraction separation method identifying from purslane.Two kinds of new flavone compounds, molecular formula are followed successively by C18H16O5、C18H18O5, name is respectively 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen-4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one.The extraction separation method of above-mentioned noval chemical compound is also provided, is successively isolated and purified and is prepared using compression leg purifying, Sephadex LH-20 and recrystallization in water boiling and extraction, silica gel column chromatography, polyamide column chromatography, ODS.Its structure using HR-ESI-TOF-MS,1H‑NMR、13C-NMR and the method for two-dimensional nuclear magnetic spectrum parsing are accredited as two kinds of neoflavonoids.New flavone compounds have potential anti-inflammatory, antitumor and anti-oxidant isoreactivity, new flavone compounds and its salt or derivative of the present invention can be used as other compound synthesis primers, and the raw material of new drug development and pharmacology activity research, it is used to prepare anti-inflammatory, antitumor and oxidation resistant drug or health care product.
Description
Technical field
The present invention relates to traditional Chinese medicine extraction, separation field, more particularly to extracting and developing and identifies from purslane medicinal material
Flavone compound and its extraction separation method.
Background technique
Purslane (Portulaca oleracea L.) also known as long life dish, horse three-coloured amaranth are portulacaceous plant.Purslane
Drought-enduring waterlogging and fast light shade tolerant, widely distributed, resourceful, the wild plant as dual-purpose of drug and food is concerned.2015 editions
The dry aerial parts that purslane is recorded in the Pharmacopoeia of the People's Republic of China are used as medicine, and have clearing heat and detoxicating, cooling blood and hemostasis, stop dysentery
And other effects, for toxic-heat and blood stasis, carbuncle swells furunculosis, eczema, erysipelas, snakebite and bugbite, hematochezia, hemorrhoid blood, metrostaxis etc..
Purslane modern pharmacology research shows it with anti-inflammatory analgesic, anti-bacteria and anti-virus, lowering blood pressure and blood fat, antioxygen
Change, anticancer, relaxation skeletal muscle and smooth muscle adjust the effects of immune function.Research shows that the numerous chemical components of purslane are it
The pharmacological action of multiplicity provides material base, purslane main chemical compositions include flavonoids, Coumarins, terpene, steroid,
Organic acid, volatile oil, alkaloids, amino acids, various pigments and minerals class etc..Wherein alkaloid is in purslane
A kind of main chemical component, composition of alkaloids reported at present have norepinephrine, dopamine, a small amount of DOPA, gland
Glycosides, uracil, adenine, N, N- dicyclohexylurea (DCU), allantoin, N- be trans--asafoetide acyl group tyrasamine；There are also Cyclic dipeptides alkaloid and
Amide alkaloid: oleracein A-I, K, L, N-S.
Most of chemical component isolated from purslane at present is known, and structure novel is lower, therefore, right
The exploitation and separation of noval chemical compound urgently need in purslane.
Summary of the invention
In view of the above-mentioned problems, the present invention provides the two kinds of neoflavonoids extracted from purslane, it has been investigated that
Two kinds of noval chemical compounds of the invention have anti-inflammatory, antitumor and oxidation resistant effect, while providing a kind of for newization of the invention
Close the extraction separation method easy, quick, environmentally friendly, with high purity of object.
Above-mentioned purpose to realize the present invention, the present invention provide the two kinds of flavone compounds isolated from purslane,
Molecular formula is respectively C18H16O5、C18H18O5, it is respectively designated as 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-
Chromen-4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one, chemical structural formula difference
Are as follows:
Above-mentioned purpose to realize the present invention, the present invention also provides a kind of extraction separation of flavone compound in purslane
Method, specific steps are as follows:
Step 1: taking the dry medicinal material of purslane, adopt and be extracted with water (water consumption be medicinal material 8~16 times) twice, Aqueous extracts filter
It crosses, merging filtrate directly heats concentration, cools to room temperature, it is spare to obtain medical fluid.
Step 2: upper silicagel column after step 1 Chinese medicine liquid is evaporated is eluted with ethyl acetate, ethyl acetate is recovered under reduced pressure to leaching
Cream obtains ethyl acetate extract.
Step 3: ethyl acetate extract in step 2 is separated through polyamide column, using alcohol-water gradient elution, 50%
Ethanolic moiety upper silicagel column after being evaporated, is successively eluted with ethyl acetate, recycling ethyl acetate to medicinal extract, obtains ethyl acetate extraction
Object.
Step 4: by gains in step 3 pretreated ODS column (Octadecylsilyl, octadecylsilane key again
Close silica filler) chromatography obtains several elution positions, detected, shown through thin-layer chromatography with methanol-water gradient elution
The elution position of each colour developing is concentrated to dryness respectively, it is spare to obtain concentrate by color.
Step 5: by gains in step 4, pretreated sephadex column (Sephadex LH-20) chromatography divides again
From, it is eluted with methanol, obtains several elution positions, detected through thin-layer chromatography, developed the color, merge the elution position of colour developing, it will
Elution position after merging is spare through being concentrated to dryness.
Step 6: step 5 standing being precipitated crystal, repeatedly with methanol is volatilized after methanol cleaning crystal, is carried out through thin-layer chromatography
Detection, colour developing, finally obtain two kinds of neoflavonoids of the present invention.
The preprocessing process of the ODS and sephadex is that methanol impregnated 24 hours, and upper prop is washed till instillation with methanol
Without muddiness in water, then balanced each other with initial flow.
Compared with prior art the beneficial effects of the present invention are: heretofore described purslane neoflavonoid
Separation and pharmacology activity research are not reported by existing paper periodical.The present invention provides two kinds of flavonoids for deriving from purslane
Object and a kind of extraction separation method for noval chemical compound of the present invention are closed, water boiling and extraction, silica gel column chromatography, polyamides are successively used
Compression leg purifying, Sephadex LH-20 and recrystallization are isolated and purified and are prepared in amine column chromatography, ODS, successfully extract separation
Two kinds of new flavone compounds out.This method operating procedure is only six steps, and operating method is easy and quick, extracts separation process
It is mainly eluted using water boiling and extraction and ethyl acetate, process environmental protection, and the compound purity isolated through this method
It is higher to be all larger than 90%.Furthermore research has shown that the above compound has anti-inflammatory, antitumor and antioxidation, therefore the present invention
Noval chemical compound and its salt and derivative can be used as other compound synthesis primers and new drug development and pharmacology activity research
Raw material, also can be used for preparing anti-inflammatory, antitumor and oxidation resistant drug.
Detailed description of the invention
Fig. 1 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
The high resolution mass spectrum figure of 4-one.
Fig. 2 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one of the present invention
High resolution mass spectrum figure.
Fig. 3 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one's1H-NMR spectrogram.
Fig. 4 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one's13C-NMR spectrogram.
Fig. 5 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
Carbon-13 nmr spectra (DEPT) spectrum of 4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one
Figure.
Fig. 6 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
The nuclear magnetic resonance of 4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one1H-1HCOSY spectrogram.
Fig. 7 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
The nuclear magnetic resonance HMBC spectrogram of 4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one.
Fig. 8 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
The nuclear magnetic resonance HSQC spectrogram of 4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one.
Fig. 9 is new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of the present invention
The nuclear magnetic resonance ROESY spectrogram of 4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one.
Specific embodiment
The present invention is described in detail below with reference to specific implementation.
The present invention provides two kinds of noval chemical compounds, and molecular formula is respectively C18H16O5、C18H18O5, it is respectively designated as 3- (2-
hydroxybenzyl)-6,8-dimethoxy-4H-chromen-4-one、3-(2-hydroxybenzyl)-6,8-
Dimethoxychroman-4-one, chemical structural formula are respectively as follows:
Described two noval chemical compounds are respectively designated as 3- (2-hydroxybenzyl) -6,8-dimethoxy- according to structure
4H-chromen-4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one, table 1,2 are respectively two
The nuclear magnetic data of kind chromocor compound:1H-NMR with13C-NMR is in CCl3In D.
Noval chemical compound 3- (the 2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen-4-one's of the present invention of table 1
Nuclear magnetic data
| Serial number | δC | Type | δH(J in Hz) |
| 1 | O | ||
| 2 | 151.11 | CH | 7.87 s |
| 3 | 125.51 | C | |
| 4 | 178.73 | C | |
| 5 | 92.58 | CH | 6.42, d, (2.2) |
| 6 | 164.76 | C | |
| 6-OMe | 55.81 | CH3 | 3.83 s |
| 7 | 96.60 | CH | 6.35, d, (2.2) |
| 8 | 161.31 | C | |
| 8-OMe | 56.61 | CH3 | 3.9, s |
| 9 | 160.65 | C | |
| 10 | 108.89 | C | |
| 11 | 27.48 | CH2 | 3.66 s |
| 1′ | 126.21 | C | |
| 2′ | 155.43 | C | |
| 2′-OH | 8.23 brs | ||
| 3′ | 118.69 | CH | 6.94, q, (8.1,14.1) |
| 4′ | 128.56 | CH | 7.12 m |
| 5′ | 120.31 | CH | 6.82, t, (7.1) |
| 6 | 130.24 | CH | 7.04, dd, (0.9,7.1) |
3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen-4-one: white powder is insoluble in first
Alcohol is soluble in chloroform.Point sample is after silica gel thin-layer plate, and the fragrant grass green test solution spot of phenol is in faint yellow.HRESI (+) TOFMS is provided
M/z:313.1071 [M+H]+Quasi-molecular ion peak, molecular weight 312.0998.In conjunction with1H-NMR,13C-NMR and DEPT number
According to, thus it is speculated that the possible molecular formula of the compound is C18H16O5, degree of unsaturation 11.13C-NMR spectrum and DEPT spectrum 18 carbon of display
Signal, respectively 2 CH3(δ: 55.81,56.61), 1 CH2(δ: 27.48), 7 CH (δ: 92.58,96.60,118.69,
120.31,128.56,130.24,151.11), 8 quaternary carbons (carbonyl carbon, δ: 178.73；The double key carbon of four company O, δ:
155.43,160.65,161.31,164.76；Three double key carbons, δ: 108.89,125.51,126.21).
1H-NMR spectrum 1 active H signal δ 8.23 (1H, brs) of display, shows that there may be a hydroxyl groups；2 first
Base signal is δ 3.83 (3H, s) and δ 3.93 (3H, s)；1 methylene signals, respectively δ 3.66 (2H, s)；7 methine letters
Number be respectively δ 6.35 (1H, d, J=2.2), δ 6.42 (1H, d, J=2.2), δ 6.82 (1H, t, J=7.1), δ 6.94 (1H, q, J
=8.1,14.1), δ 7.04 (1H, dd, J=0.9,7.1), δ 7.12 (1H, m), δ 7.87 (1H, s).According to1H-1H COSY spectrum can
Know, methylene δ 3.66 is coupled with methine δ 7.87；Two methine δ 6.35 and δ 6.42 are coupled；Methine δ 6.82, δ
7.04, δ 7.12, δ 6.94 intercouples, and illustrates the presence for having phenyl ring.Compose relevant peaks according to HMBC and show H-5, H-7 respectively with C-
9, C-10 are coupled, and H-5, H-7 intercouple, and illustrate that C-5 is associated with C-7, and respectively with C-9, C-10 is related by C-5, C-7
Connection；δ in two methoxyl groupsH3.83 δH3.93 are coupled with C-6, C-8 respectively, and C-6 (δ 164.76), C-8 (δ 161.31)
It positioned at low field area, prompts to be connected with O, illustrates that two methoxyl groups are connected with the C-6 on phenyl ring, C-8 respectively；Phase is composed according to ROESY
Guan Feng shows the δ in two methoxyl groupsH3.83 δH3.93 are coupled with H-5, H-7 respectively, illustrate C-6 and C-5, C-8 and C-7
It is associated；H-5 is coupled with C-9, and C-9 (δ 160.65) is located at low field area, prompts C-5 related to C-9, and C-9 is connected with O；
Meanwhile H-5, H-7 are related to C-10, illustrate that C-5, C-7 and C-10 are related；H-2 is coupled with H-11, and H-2, H-11 and C-3
It is coupled, illustrates that C-2, C-11 and C-3 are related, while C-2 (δ 151.11) is located at low field area, prompt to be connected with O, meanwhile, H-2
It is coupled with C-9, illustrates C-2, be connected among C-9 with O；The carbonyl C of H-2, H-5, H-11 and C-4 are coupled, and illustrate C-2, C-
5, C-11 is associated with C-4.H-3 ', H-4 ', H-5 ' and H-6 ' intercouple, wherein H-3 ', H-5 ', H-6 ' and C-1 ' phase coupling
It closes, H-3 ', H-4 ', H-5 ', H-6 ' and C-2 ' is coupled, and prompts the presence for having phenyl ring and C-1 ' and C-2 ' ortho position substitution；Wherein
C-2 ' (δ 155.43) is in low field area, prompts to be connected with O, illustrates that C-2 ' is connected with a hydroxyl group；H-2, H-11 and C-1 ' phase
Coupling, illustrates that C-2, C-11 and C-1 ' are related, and H-11 and C-2 ', C-6 ' are coupled, and illustrates C-11 and C-2 ', C-6 ' is related, H-
6 ' and C-1 ' is coupled, and illustrates that C-6 ' is related to C-1 ', to sum up illustrates that C-11 is connected with C-1 '.According to information above, it may be determined that
This noval chemical compound is above structure.
The nuclear-magnetism of noval chemical compound 3- (the 2-hydroxybenzyl) -6,8-dimethoxychroman-4-one of the present invention of table 2
Data
3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one: white powder is insoluble in methanol, easily
It is dissolved in chloroform.Point sample is after silica gel thin-layer plate, and the fragrant grass green test solution spot of phenol is in faint yellow.HRESI (+) TOFMS provides m/z:
315.1224[M+H]+Quasi-molecular ion peak, molecular weight 314.1154.In conjunction with1H-NMR,13C-NMR and DEPT data,
Speculate that the possible molecular formula of the compound is C18H18O5, degree of unsaturation 10.13C-NMR spectrum and DEPT spectrum show 18 carbon letters
Number, respectively 2 CH3(δ: 55.97,56.33), 2 CH2(δ: 26.85,70.52), 7 CH (δ: 47.80,93.14,
93.40,117.76,120.43,128.62,131.04), 7 quaternary carbons (carbonyl carbon, δ: 194.09；The double bond of four company O
Carbon, δ: 155.12,162.79,165.56,166.70；Two double key carbons, δ: 105.45,125.17).
1H-NMR spectrum 1 active H signal δ 9.65 (1H, brs) of display, shows that there may be a hydroxyl groups；2 first
Base signal, for δ 3.88 (6H, s)；2 methylene signals, respectively δ 2.79 (1H, q, J=6.6,16.7), δ 3.06 (1H, m)；
δ 4.17 (1H, t, J=11.3), δ 4.53 (1H, dd, J=4.9,11.2)；7 methine signals are respectively δ 3.04 (1H, m), δ
6.05 (2H, q, J=2.3,3.7), δ 6.82 (1H, t, J=7.1), δ 6.94 (1H, q, J=8.1,14.1), δ 7.11 (1H, m),
δ 7.12 (1H, m).According to1H-1H COSY spectrum it is found that H δ 4.17 in methylene, δ 4.53, δ 2.79, δ 3.06 respectively with secondary first
Base δ 3.04 is coupled；Two methine δ 6.05 and δ 6.05 are coupled；Methine δ 6.82, δ 6.94, δ 7.11, δ 7.12 are mutual
Coupling, illustrates the presence for having phenyl ring.Relevant peaks, which are composed, according to HMBC shows H-5, H-7 is coupled with C-9, C-10 respectively, and H-5,
H-7 intercouples, and illustrates that C-5 is associated with C-7, and C-5, C-7 are associated with C-9, C-10 respectively；δ in two methoxyl groupsH3.88 (6H, s) and C-6, C-8 are coupled, and C-6 (δ 166.70) and C-8 (δ 162.79) are located at low field area, prompt and O phase
Even, illustrate that two methoxyl groups are connected with the C-6 on phenyl ring, C-8 respectively；Show the δ in two methoxyl groups according to ROESY spectrumH3.88 (6H, s) and H-5, H-7 are coupled, and illustrate that C-6, C-8 and C-5, C-7 are associated；H-5 is coupled with C-9, and C-9 (δ
160.65) it is located at low field area, prompts C-5 related to C-9, and C-9 is connected with O；H-2, H-3, H-11 intercouple, and C-2 (δ
70.52) it is located at low field area, prompts to be connected with O, meanwhile, H-2 is coupled with C-9, illustrates C-2, is connected among C-9 with O；H-2,
The carbonyl C of H-3, H-11 and C-4 are coupled, and illustrate that C-2, C-3, C-11 and C-4 are associated.H-3 ', H-4 ', H-5 ' and H-6 ' phase
Mutual coupling, wherein H-3 ', H-5 ', H-6 ' and C-1 ' are coupled, and H-3 ', H-4 ', H-5 ', H-6 ' and C-2 ' is coupled, and prompt has
The presence of phenyl ring and C-1 ' and C-2 ' ortho position substitution；Wherein C-2 ' (δ 155.12) is in low field area, prompts to be connected with O, illustrates C-
2 ' are connected with a hydroxyl group；H-2, H-3, H-11 and C-1 ' are coupled, and illustrate that C-2, C-3, C-11 and C-1 ' are related, H-11 with
C-2 ', C-6 ' are coupled, and illustrate C-11 and C-2 ', and C-6 ' is related, and H-6 ' and C-1 ' is coupled, illustrate it is related to C-1 ', to sum up
Illustrate that C-11 is connected with C-1 '.According to information above, it may be determined that this noval chemical compound is above structure.
The present invention also provides the extraction separation method of above two chromocor compound, specific steps are as follows:
Step 1: the dry medicinal material 150kg of purslane is weighed, using water refluxing extraction, water consumption (v/v) is 10 times of medicinal material,
Twice, each 2h, heating concentration cools to room temperature, it is spare to obtain medical fluid refluxing extraction.
Step 2: separating after gained medical fluid in step 1 is evaporated through silica gel column chromatography, washed with ethyl acetate (115L) is isocratic
De-, wherein silica gel is 100-200 mesh, and 40 DEG C or less are recovered under reduced pressure ethyl acetate to medicinal extract, obtain ethyl acetate extract.
Step 3: ethyl acetate extract in step 2 is separated through polyamide column, using alcohol-water (0/100,30/70,
50/50,70/30,100/0, v/v) gradient elution, 50% (percentage by volume) ethyl alcohol separate after being evaporated through silica gel column chromatography,
Middle silica gel is 200~300 mesh, successively uses ethyl acetate, acetate-methanol (5/1,2/1,1/2, v/v) gradient elution, there are
It to 19 positions (19 bottles, every bottle of 300mL is obtained), is detected through thin-layer chromatography, develops the color, ethyl acetate is eluted
Merge to position, and more than room temperature, 40 DEG C or less are concentrated to dryness, spare.
Step 4: by gains in step 3 again the separation of pretreated ODS medium pressure column chromatography (Octadecylsilyl, ten
Eight alkyl silane bonded silica gel fillers), wherein filler particle size be 20~40 μm, with methanol-water (60/40,70/30,80/20,
90/10,100/0, v/v) gradient elution (pressurization, make flow velocity 1mL/min, temperature is room temperature), obtains 16 position (i.e. gradients
Elute to obtain 16 bottles, every bottle of 100mL), it is detected, is developed the color through thin-layer chromatography, 3~5 positions of colour developing are retained, 50 DEG C or less
It is concentrated to dryness, it is spare.
Step 5: by pretreated sephadex column chromatography for separation (the Sephadex LH- again of gains in step 4
20) it, is eluted with methanol, obtains 26 elution positions (26 bottles, every bottle of 50mL is obtained), detected through thin-layer chromatography,
Colour developing retains the 13 of colour developing, 14 positions, and 50 DEG C or less are concentrated to dryness, spare, obtains noval chemical compound.
Step 6: gains in step 5 being stood, light yellow crystal to be precipitated is detected through thin-layer chromatography, developed the color, more
It is secondary to use methanol cleaning crystal, be washed till methanol supernatant in methanol is evaporated after colourless, finally obtain two kinds of the present invention it is new yellow
Ketone compound.
The preprocessing process of the ODS and sephadex is that methanol impregnated for 24 hours, and upper prop is balanced each other with initial flow.
The anti-inflammatory effect of new flavone compounds of the present invention is tested.
1 main material
1.1 drugs and reagent: testing two kinds of new flavone compounds used and prepared by the above method, and purity is 90~99%,
Precision weighs, solution needed for being diluted to following each dosage groups with DMSO.DMEM high glucose medium, fetal calf serum (U.S. Hyclone
Company)；Penicillin, streptomysin (Hangzhou Chinese holly company)；LPS (Sigma Co., USA)；IL-6,TNF-α,PGE2ELISA
Kit (Cayman company, the U.S.)；Cell pyrolysis liquid, Griess reagent (green skies Bioisystech Co., Ltd).
1.2 cell strains: RAW264.7 macrophage (U.S.'s ATCC cell bank).
1.3 groupings: being divided into control group, LPS group and experimental group, and each one group.
2 experimental methods
2.1 cell culture: the fetal calf serum of l0%, l% antibiotic (100U/mL penicillin is added in DMEM high glucose medium
With 100 μ g/mL streptomysins), it is placed in 37.5%, CO2It is cultivated in incubator.
2.2MTT colorimetric method for determining cell viability: above-mentioned three groups of difference logarithmic growth phase RAW264.7 macrophage inoculation
In 96 well culture plates, cell density is 1 × 104A/mL, every 100 μ L of hole, 37 DEG C of temperature, 5%CO2Under the conditions of overnight incubation
Afterwards, two kinds of new flavone compounds 3- (2-hydroxybenzyl) -6,8- of the present invention of various concentration are added in experimental group
Dimethoxy-4H-chromen-4-one (1-100 μM) or 3- (2-hydroxybenzyl) -6,8-
Dimethoxychroman-4-one (1-100 μM) is incubated for after 1h and is separately added into final concentration of 1 μ g/mL to LPS group and experimental group
LPS, separately set zeroing group (culture solution of the solvent containing DMSO), every group sets 3 multiple holes, investigates the shadow after drug is added to cell
It rings.After above-mentioned group of cells culture for 24 hours, the addition 5mg/mL MTT20 μ L in each hole cell, 37 DEG C of temperature, 5%CO2Under the conditions of
Continue after being incubated for 4h, terminate culture, inhale and abandon liquid in hole, 100 μ L dimethyl sulfoxides (DMSO) are added in every hole, vibrate 10min, make
Intracellular crystallization is sufficiently dissolved, each hole light absorption value of measurement at microplate reader 570nm wavelength.
2.3 measure the content of NO using Ge Lisi (Griess) method, investigate what new flavone compounds of the present invention induced LPS
The inhibiting effect of the NO yield of mouse macrophage RAW264.7.Containing 10% tire after mouse macrophage RAW264.7 passage
It is cultivated in the sugared cell culture medium DMEM of the height of cow's serum, two kinds of new flavone compounds 3- of the present invention of various concentration are added in experimental group
(2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen-4-one (1-50 μM) or 3- (2-
Hydroxybenzyl) -6,8-dimethoxychroman-4-one (1-50 μM), at 37 DEG C, 5%CO2Under the conditions of be incubated for 1h after
Inflammatory reaction is induced with LPS (final concentration of 1 μ g/mL), collects supernatant afterwards for 24 hours, every group of processing repeats 3 holes.Griess method is surveyed
The content for determining NO in cell supernatant, the RAW264.7 that LPS is induced according to various concentration two kinds of new flavone compounds of the invention
Cell discharges the influence of NO, to reflect NO level.
2.4ELISA method measures inflammatory factor IL-6, TNF-α and inflammatory mediator PGE2: logarithmic growth phase RAW264.7 is huge
Phagocyte is inoculated in 24 well culture plates, and cell density is 1 × 105A/mL, every hole 1mL, 37 DEG C of temperature, 5%CO2Under the conditions of train
It supports overnight, two kinds of new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H- of the invention are added in experimental group
Chromen-4-one (1-50 μM) or 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one (1-50 μ
M), after cultivating 1h, LPS (final concentration of 1 μ g/mL) is added in every hole, is incubated for altogether for 24 hours, every group of processing repeats 3 holes.ELISA method is surveyed
Determine two breeds of horses bitterroot source new flavone compounds treated IL-6, TNF-α and the PGE of RAW264.7 macrophages secrete2's
Content.
3 experimental results
The experimental results showed that proliferation nothing of the two kinds of new flavone compounds of the invention to the LPS macrophage RAW264.7 induced
It influences, it is safe and non-toxic；And excess inflammatory cytokine IL- produced by the macrophage RAW264.7 of LPS induction can be effectively suppressed
6, TNF-α and inflammatory mediator NO, PGE2, and be in concentration dependant.
Comparative survival rate of cells experimental result is as shown in table 3.
Influence of 3 present invention of table to RAW264.7 macrophage relative survival rate
Note:*P < 0.05 is compared with the control group (high concentration group has significant difference)
4 are shown in Table using the content experimental result of Ge Lisi (Griess) method measurement NO.
Influence (mean ± standard deviation, n=3) of 4 present invention of table to the RAW264.7 cell release NO of LPS induction
Note:*P < 0.05 compared with the control group,#P < 0.05 is compared with LPS group.
ELISA method measures inflammatory factor IL-6, TNF-α and inflammatory mediator PGE2The results are shown in Table 5.
IL-6, TNF-α and PGE of 5 present invention of table to the RAW264.7 cell secretion of LPS induction2Influence (the mean of content
± standard deviation, n=3)
Note:*P < 0.05 compared with the control group,#P < 0.05 is compared with LPS group.
The antitumor action of new flavone compounds of the present invention.
1 main material
1.1 drugs and reagent: testing two kinds of new flavone compounds used and prepared by the above method, and purity is 90~99%,
Precision weighs, solution needed for being diluted to following each dosage groups with DMSO.DMEM high glucose medium, fetal calf serum (U.S. Hyclone
Company)；Penicillin, streptomysin (Hangzhou Chinese holly company).
1.2 cell strains: Human colon adenocarcinoma cell line Caco-2, human breast cancer cell line Bcap-37, human gastric cancer cells BGC-823, people's lung
Adenocarcinoma cell SPC-A1, human liver cancer cell BEL-7402, human cervical carcinoma cell Hela-229, ovarian cancer cell Ho-8910, the mankind
Oral cavity epidermoid carcinoma cell KB (Chinese Academy of Sciences's Shanghai cell bank).
1.3 groupings: it is divided into control group, experimental group and zeroing group (culture solution of the solvent containing DMSO).
2 experimental methods
2.1 cell culture: the fetal calf serum of l0%, l% antibiotic (100U/mL penicillin is added in DMEM high glucose medium
With 100 μ g/mL streptomysins), it is placed in 37 DEG C, 5%CO2It is cultivated in incubator.
2.2MTI method detect cell Proliferation: logarithmic growth phase cell inoculation in 96 well culture plates, cell density be 1 ×
104A/mL, every 100 μ L of hole, 37 DEG C of temperature, 5%CO2Under the conditions of after overnight incubation, the present invention of various concentration is added in experimental group
Two kinds of new flavone compounds 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen-4-one or 3- (2-
Hydroxybenzyl) -6,8-dimethoxychroman-4-one, 3 multiple holes are set for every group, dosing is placed on 37 DEG C, 5%CO2
48h is cultivated in incubator.Drug containing culture solution is sucked, (whole quality is dense for the serum-free medium and MTT that addition volume ratio is 4:1
Degree is the total 100mL of 5mg/L), continues to be incubated for 4h, and after carefully sucking supernatant, DMSO150 μ L is added in every hole, is put on oscillator
It shakes so that crystallization is completely dissolved (5min), microplate reader detects absorbance (A) value in each hole under 570nm wavelength.Then, it calculates
The inhibiting rate of each concentration compounds on cell growth, reapplies SPSS software data processing, and inhibiting rate wrirtes music to drug concentration
Line calculates IC50Value.
Inhibiting rate formula: inhibitory rate of cell growth=(1-AMedicine feeding hole/AControl wells) × 100%
3 experimental results
The experimental results showed that two kinds of new flavone compounds of the invention are to Human colon adenocarcinoma cell line Caco-2, human breast cancer cell
MCF-7, human gastric cancer cells BGC-823, human lung adenocarcinoma cell SPC-A1, human liver cancer cell BEL-7402, human cervical carcinoma cell
Hela-229, ovarian cancer cell Ho-8910, the proliferation of Human Oral Cavity epidermoid carcinoma cell KB are inhibited, and with drug
Concentration increases, and inhibiting rate is also significantly raised, that is, is in concentration dependant.Two kinds of new flavone compounds of the invention are thin to above-mentioned eight kinds of tumours
Born of the same parents IC50Value is shown in Table 6.
Inhibiting effect of the two kinds of new flavone compounds of the invention of table 6 to tumour cell
The antioxidation of new flavone compounds of the present invention is tested.
1 main material
1.1 drugs and reagent: testing two kinds of new flavone compounds used and prepared by the above method, and purity is 90~99%,
Precision weighs, the solution needed for methanol dilution to following each dosage groups.DPPH (1,1- diphenyl -2- picryl hydrazine free radical)
(Sigma-Fluka company)；BHA (tert-butyl hydroxyanisole) (Shanghai auspicious sign Science and Technology Ltd.)；Methanol, chromatographically pure (prosperous Thailand
Industrial Co., Ltd).
1.2 groupings: being divided into control group, experimental group and blank group, and each one group.
2 experimental methods
The ability of colorimetric method for determining elimination DPPH free radical: experimental group takes 1mL DPPH solution (126.80 μM) to be added to
In 4mL cuvette, the 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H-chromen- of 1mL various concentration is added
4-one (8.32,16.61,33.31,50.02,66.61 μM) or 3- (2-hydroxybenzyl) -6,8-
Dimethoxychroman-4-one sample solution (8.32,16.61,33.31,50.02,66.61 μM)；Control group takes 1mL first
Alcoholic solution is added in 4mL cuvette, adds the sample solution of 1mL various concentration；Blank group takes 1mL DPPH solution to be added
Into 4mL cuvette, 1mL methanol solution is added.Three groups mix well, and room temperature, which is protected from light, stands 10min, measure under 517nm
Light absorption value operates in the same way after standing 30min.Each sample average measurement is averaged three times, and positive control is difference
The BHA solution of concentration.Sample is calculated according to the following formula to the clearance rate of DPPH free radical, and it is clear to further calculate its free radical
Except rate IC50Value.
DPPH clearance rate (%)=1- (A1- A2)/A0× 100%
Wherein, A0For the absorbance value of blank group；A1For the absorbance value of sample sets；A2For the absorbance value of control group.
3 experimental results
The experimental results showed that two kinds of flavones noval chemical compounds of the invention all have scavenging effect to DPPH free radical, and with drug
Concentration increases, and clearance rate is also significantly raised.Two kinds of flavones noval chemical compounds of the invention are to DPPH free radical IC50Value is shown in Table 7.
Scavenging effect of the two kinds of new flavone compounds of the invention of table 7 to DPPH free radical
In conclusion the present invention provides two kinds of new flavone compounds and its extraction separation method, successively mentioned using water decoction
Take, in silica gel column chromatography, polyamide column chromatography, silica gel column chromatography, ODS compression leg and recrystallization isolated and purified and prepared, at
Isolated two kinds of noval chemical compounds of function.This method is easy, quick, environmentally friendly, and the compound purity isolated through this method
It is higher.Since gained compound chemical structure is unique, extracted from conventional Chinese medicine purslane, with anti-inflammatory, antitumor
And antioxidation, therefore two kinds of new flavone compounds and its salt and derivative of the invention can be used as in natural products exploitation
Medicine new drug, has broad prospects.
Claims (10)
1. the two kinds of neoflavonoids isolated from purslane medicinal material, which is characterized in that molecular formula is respectively as follows:
C18H16O5、C18H18O5, and 3- (2-hydroxybenzyl) -6,8-dimethoxy-4H- is respectively designated as according to structure
Chromen-4-one, 3- (2-hydroxybenzyl) -6,8-dimethoxychroman-4-one, chemical structural formula difference
It is as follows:
,。
2. the extraction separation method of compound as described in claim 1, which is characterized in that specific steps are as follows:
Step 1: the dry medicinal material of purslane being taken to cool to room temperature using water boiling and extraction, it is spare to obtain medical fluid；
Step 2: upper silicagel column after step 1 Chinese medicine liquid is evaporated is eluted with ethyl acetate, ethyl acetate is recovered under reduced pressure to medicinal extract,
Obtain ethyl acetate extract；
Step 3: ethyl acetate extract in step 2 being separated through polyamide column, using alcohol-water gradient elution, 50% ethyl alcohol portion
Divide upper silicagel column after being evaporated, eluted with ethyl acetate, recycles ethyl acetate to medicinal extract, obtain ethyl acetate extract；
Step 4: by gains in step 3 pretreated ODS column (Octadecylsilyl, octadecylsilane chemically bonded silica
Filler) chromatography obtains several elution positions, detected through thin-layer chromatography with methanol-water gradient elution, develops the color, and it will be each
The elution position of colour developing is concentrated to dryness respectively, and it is spare to obtain concentrate；
Step 5: pretreated sephadex column (Sephadex LH-20) chromatography again of gains in step 4 is used
Methanol elution, obtains several elution positions, is detected through thin-layer chromatography, develops the color, merges the elution position of colour developing, after merging
Elution position through being concentrated to dryness, it is spare；
Step 6: precipitating crystal being stood in step 5, repeatedly with methanol is volatilized after methanol cleaning crystal, examined through thin-layer chromatography
It surveys, colour developing, finally obtains two kinds of neoflavonoids of the present invention.
3. extraction separation method as claimed in claim 2, which is characterized in that in the step 1 water boiling and extraction twice, every time
It decocts 2 hours, water is 8~16 times of medicinal material.
4. extraction separation method as claimed in claim 2, which is characterized in that mobile phase elution program used in the step 2
For isocratic elution.
5. extraction separation method as claimed in claim 2, which is characterized in that use the volume ratio of water and ethyl alcohol in the step 3
For 100/0,70/30,50/50,30/70 and 0/100 gradient elution；Ethyl acetate elution program used is etc. in the step 3
The volume ratio of degree elution, ethyl acetate and methanol is 5/1,2/1 and 1/2 gradient elution；The body of first alcohol and water is used in the step 4
Product is than being 50/50,60/40,70/30 and 80/20 gradient elution.
6. extraction separation method as claimed in claim 2, which is characterized in that ODS used in the step 4 and step 5 with
The preprocessing process of sephadex is that methanol impregnated 24 hours, and upper prop is washed till with methanol and is instilled in water without muddiness, then with first
Begin to flow and balance each other.
7. extraction separation method as claimed in claim 2, which is characterized in that be with methanol elution program in the step 5
Degree elution.
8. compound as described in claim 1 is preparing the purposes in anti-inflammatory drug or health care product.
9. compound as described in claim 1 is preparing the purposes in anti-tumor drug or health care product.
10. compound as described in claim 1 is preparing the purposes in anti-oxidation medicine or health care product.
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